And while I was preparing this presentation, I realized something uncomfortable: I’m really good at using these frameworks to avoid bad outcomes in my creative business. But historically I’ve been pretty terrible at using them to pursue opportunities.

Let me show you what I mean.

The Decision I Got Right

A few years ago, I faced a choice that trips up a lot of creatives: how to sell my work.

The prevailing wisdom was clear—build your own website, sell direct, own the customer relationship. Don’t send people to print-on-demand platforms where they’ll get bombarded with your competitors. Keep them on your site. Make more profit per item.

It’s not wrong advice. The logic is sound. So I followed it.

I set up my own website. Connected it to Printful. Listed my favorite designs. Shared it with friends and family. Got a few sales.

Then the emails started.

“Hey, my order hasn’t arrived yet—do you know what’s up?”

These were people I knew and loved, asking perfectly reasonable questions. And I found myself frustrated. Not at them—at the situation. If I was finding it this annoying when it was just my mom asking about her order, what would happen when I had dozens of customers I didn’t know?

The breaking point was clear: I didn’t want that part of the business. I wanted to make the art. That was it.

Here’s where my ops brain kicked in. The standard creative business advice was asking me to take on a specific risk: that customer service and fulfillment logistics would consume the limited time I had available for creative work.

Let me be clear about my constraints: I run a full-time consulting business. K Bedford Consulting pays my bills. My creative work—Nomadic Raconteur—fills my soul. I have maybe 5-10 hours a week for art-related activities. If I spent those hours answering shipping questions and managing print vendor relationships, when would I actually illustrate?

So I did what I do in my ops consulting work: I stopped treating it like a moral decision and started treating it like a comparison. For each option, what’s the likelihood something will go wrong, and how big of a problem will that actually be?

Option 1: Sell through my own website with Printful

• Problem: Customer service issues pulling me away from billable work and art creation

• Likelihood: High (it was already happening with just friends and family)

• Impact: High (time is my scarcest resource; every hour on customer service is an hour not consulting or creating)

Option 2: Sell through Redbubble/TeePublic

• Problem: Lower revenue per item and less control

• Likelihood: Guaranteed (this is just how these platforms work)

• Impact: Low (losing $5 per item matters way less than losing 5 hours per week)

When you lay it out like that, the choice of which risk to avoid becomes obvious. High likelihood + high impact beats guaranteed + low impact every time.

So I moved everything to print-on-demand platforms and stopped second-guessing it. The platforms handle returns, reprints, shipping complaints, all of it. I protect the time I need to actually create.

This is threat management. I identified what could sink my creative practice and I actively worked to prevent it. Gold stars for me.

You Can’t Stop the Waves

There’s a quote from Jon Kabat-Zinn that’s become the centerpiece of my Bureau presentation: “You can’t stop the waves, but you can learn to surf.”

In both agency operations and creative businesses, some challenges are inevitable. You can’t prevent them from happening—client budgets shift, technology disrupts pricing models, customer service demands pile up. What you can do is get better at recognizing them early and making strategic choices about how to respond.

That’s what I did with print-on-demand. I saw the customer service demand coming, assessed the impact, and made a strategic move to transfer that risk before it consumed me. I thought I had this figured out, until building my presentation forced me to confront what I wasn’t doing.

The Decision I Keep Avoiding

I’m excellent at identifying threats. I see what could capsize my creative practice and I navigate around it or hand it off to someone else. I protect my creative time ferociously. I’ve eliminated everything in my art business that doesn’t directly serve the actual making of the work.

But opportunities? I haven’t exactly been great at capitalizing on those.

Right now, the biggest opportunity in my creative business is licensing deals. Redbubble and TeePublic are great for proving there’s demand, but I’m never going to sell the volume through those platforms that I could through licensing arrangements. This is the obvious lever to pull. The highest impact move available to me.

So why haven’t I pursued it? Great question. I couldn’t actually answer this question, so I made myself do a risk assessment of this opportunity. Let me run you through it.

Pursuing licensing deals:

• What could go wrong: Time investment in both research and outreach, facing rejection

• Likelihood: High (this will definitely require effort and I’ll definitely hear “no” more than “yes”)

• Impact: High (this is the path to my actual goal—passive income in retirement doing something I love)

NOT pursuing licensing deals:

• What could go wrong: Stay at current revenue ceiling, miss the window while designs are trending, never build the retirement income stream I want

• Likelihood: Guaranteed (if I don’t pursue it, it definitely won’t happen)

• Impact: High (means my “retirement dream” stays a dream)

When I lay THAT out, the choice should be just as obvious as the print-on-demand decision.

Except I keep not doing it.

My instinct is to say I don’t have time. But the real truth? I haven’t prioritized it because it requires putting myself out there for rejection. Creating a portfolio specifically for licensing. Building a targeted outreach list. Probably setting up some kind of automation to make that outreach faster while maintaining personalization.

All of that feels hard. So I’ve been protecting my time (threat management: excellent) while simultaneously avoiding the one thing that could actually get me where I want to go (opportunity management: terrible).

What I Realized While Teaching Others

By preparing to teach other people about risk management, I started seeing my own blind spots.

I’ve always known that I tend to do a really good job mitigating threats but a pretty poor job pursuing opportunities. But working on this presentation made me confront it directly. I was literally creating slides about how to exploit opportunities and enhance the likelihood of good things happening, while completely ignoring that exact advice in my own business.

There’s a saying that ‘teaching is the highest form of understanding’—and I can confirm that’s true, even when what you learn is uncomfortable.

The framework I use for agencies works the exact same way for creative businesses:

For threats, you can:

• Avoid them (change your approach so the risk can’t happen)

• Mitigate them (reduce the chance or impact)

• Transfer them (shift the risk to someone else—like I did with print-on-demand)

• Accept them (consciously decide it’s not worth managing)

For opportunities, you can:

• Exploit them (make sure the good thing happens—get it in writing, lock it down)

• Enhance them (increase the odds by investing time or resources)

• Share them (partner with others to expand bandwidth)

• Accept them (be aware but choose not to pursue right now)

I’m excellent at the first list. I can navigate threats all day long.

But I’ve been treating opportunities like threats—something to avoid rather than something to actively pursue.

Both Sides of the Equation

Most creative business advice optimizes for revenue. But after straddling both worlds—running an ops consulting business and building a creative one—I think that’s wrong. You need to optimize for sustainability first, opportunity second.

Figure out what part of your creative business fills your cup and protect that time ferociously. Everything else—marketing, fulfillment, customer service, administrative overhead—needs to be minimized to a manageable amount of work.

But once you’ve protected that core creative time, you can’t just hide there. You have to actively pursue the opportunities that will actually move your business forward. That means doing the scary thing, the thing that risks rejection, the thing that requires sustained effort without guaranteed payoff.

You cannot avoid risk. Not really. You can only make conscious choices about which risks you’re willing to take and which ones you need to actively manage—both the threats and the opportunities.

Right now, I need to stop only managing threats and start enhancing opportunities. Which means building that licensing portfolio, creating that outreach list, and accepting that I’ll probably hear “no” forty-nine times before I hear “yes” once.

What I really want is to make art because I love it and create a passive revenue stream that helps fuel my retirement. That’s the dream. That’s what I’m working toward. And it’s a dream I could actually realize if I quit slacking and make shit happen.

So here’s what I’m doing: I’m committing to creating a licensing-focused portfolio by the end of February. Building my outreach list by mid-March. Making my first pitch by April.

I’m telling you this because accountability helps, and because I think a lot of creatives are probably better at threat management than opportunity pursuit. We’re good at protecting our time and avoiding burnout. We’re not as good at the proactive, rejection-risking, big-swing-taking moves that actually transform the business.

Maybe that’s just me. But I don’t think so.

What About You?

What are you avoiding in your creative business right now? What’s the opportunity you keep not pursuing? Hit reply and tell me—I’ll read it, and maybe we can hold each other accountable.

If this resonated with you, hit that little heart button—it actually matters a lot more than you’d think. The algorithm gods are fickle, and apparently they want to know if this is worth showing to other humans. And if you’re feeling generous? Share it with someone who’d actually enjoy it. That’s how we keep weird, honest content floating around instead of just the usual noise ✌️

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I know, I know. It sounds like such a basic question. The kind of thing you assume you’ll just know when the time comes. But here I am, cursor hovering over the upload button on Redbubble for the hundredth time, staring at a layer in Procreate labeled “signature,” trying to decide if I should keep it or delete it.

And every single time, I delete it. Because it feels safer.

But lately? That safe choice is starting to feel wrong.

Here’s What’s Happening

I create a piece of artwork. I add my tag—not a traditional signature, but a symbol based on my initials and signature (I’ll show you in a second). Then I sit there wondering: Does this belong here? Will it look weird on a t-shirt? Should I only use it for prints? What if someone thinks it’s just part of the design and not actually my mark?

So I remove it. Upload the clean version. Move on to the next piece.

Then I look around my office at the artwork I’ve printed for myself—pieces I’m genuinely proud of—and I feel this pang of regret. They don’t have my mark on them. If someone saw these on my wall, they wouldn’t know I made them. And that bothers me more than I thought it would.

The Tag Situation

Here’s what I’m working with instead of a traditional signature:

It starts with my initials, my signature flows into it, then spirals into this mark that looks a bit like a heart with a line underneath. I think it’s cool. I think it’s memorable. But I honestly don’t know if using a tag instead of a readable signature is shooting myself in the foot.

Here’s the thing: I like my tag. But is there a downside I’m not seeing? Does it confuse people? Does it look like it’s just part of the design rather than a signature?

The Preposterous Questions That Keep Me Up at Night

Every time I’m about to upload something, I’m running through this mental checklist:

For wall art/prints: I’m looking at the piece in my office that does have my tag (bottom right corner, small but noticeable), and it looks great. I’m proud to have my mark on it. But then I look at the others without it, and I wish I’d added it. They feel incomplete now, like I didn’t fully claim them.

For products (t-shirts, mugs, phone cases): This is where I really spiral. That same design that looks perfect on canvas? It can also go on a t-shirt where it might look like a weird smudge or misprint. Do I need separate versions? Is that what everyone else does, or am I overthinking this?

Some print on demand sites let you upload different images for different products. So maybe the answer is: clean version for small-format items, signed version for anything art-print-adjacent? But I genuinely don’t know if that’s standard practice or if I’m just making things unnecessarily complicated.

What This Indecision Is Actually Costing Me

Two things are eating at me:

First, the mental energy of re-deciding this every single time I upload something. It’s exhausting. I just want a system—a clear “this is when I sign it, this is when I don’t”—so I can move on with my life.

Second, and maybe more importantly: my work is out there in the world essentially anonymous. If someone sees one of my designs and loves it, they might not be able to find me. That’s a missed opportunity I can’t afford to keep creating.

I’ve Taken So Many Art Business Courses...

...and not one of them has covered this. They talk about pricing strategies, marketing funnels, social media presence, building an email list. All important stuff! But nobody has a module on “where does your signature actually go and when do you use it?”

It feels like such a newbie question that I’ve been almost embarrassed to ask. But you know what? I’m asking anyway. Because I can’t be the only one who’s stood in front of their own artwork, feeling torn about whether to claim it or keep it clean.

Here Are My Actual Questions for You

I need help. Real, practical, been-there-done-that advice from people who’ve figured this out. Specifically:

About signing in general: What’s your rule of thumb for when something deserves your signature?

About my tag specifically: When you look at my tag, does it read as “this is the artist’s mark” or does it look like it’s just part of the design?

About different formats: At what size does a signature stop being recognizable and start being visual clutter?

About your mistakes: What do you wish someone had told you about this when you were starting out?

About purchasing art: Does the presence of a signature or tag make you not want to buy a design on a shirt, mug etc.?

The Bottom Line

Right now, I’m defaulting to “no signature because it feels safer,” but I’m increasingly second-guessing that choice. I want to claim my work. I’m proud of what I create. But I also don’t want my signature to be the reason someone scrolls past my design or decides not to buy it.

Future me—six months from now, a year from now—probably has this figured out. Future me probably has a system and isn’t agonizing over every upload. And I think Future me would say: “The tag is part of your brand, use it. But don’t shoot yourself in the foot by making designs nobody wants to buy.”

I just need to figure out how to get from here to there.

So... Help?

I’m serious. I’m a sponge. I want all the opinions, all the approaches, all the hard-won wisdom you’ve got.

I promise I’m listening. And if nobody responds, I’ll just be over here still floundering, staring at that signature layer, trying to decide if today’s the day I finally commit.

Don’t let me flounder alone.

It reminded me of Tina Fey’s famous advice: “Say yes. You’ll figure it out afterwards.”

So I started down the rabbit hole of this “just say yes” philosophy, and I stumbled into something much more intriguing. Most successful people follow a predictable pattern: say yes early to build skills, then say no more often to maintain focus. But there’s a whole category of wildly successful people who never stopped saying yes. And their approach to building careers is fascinatingly different.

The Never-Stop-Saying-Yes Pattern

Take Nishant’s journey: PhD in neuroscience → political cartoonist → stand-up comedian → novelist → urban sketching as stress relief → The Sneaky Artist. He didn’t just try many things—he was genuinely good at each one.

Or Tina Fey: her “say yes” advice comes directly from improv training at Second City, but look at her range: first female SNL head writer → Weekend Update anchor → 30 Rock creator and star → Mean Girls screenwriter → Broadway musical adapter → Golden Globes host → Netflix series creator. She’s simultaneously a writer, performer, producer, and business builder.

Then there’s Ryan Reynolds: actor → producer → marketing agency founder → telecom company owner → gin brand builder → soccer team owner → Formula 1 investor. He doesn’t just lend his name to these ventures—he becomes the creative heartbeat of each business.

Richard Branson represents the ultimate example: 400+ companies across airlines, space tourism, music, trains, mobile services, banking, health clubs, cruise lines, hotels... the list is endless.

The Multi-Passionate Mind

What strikes me about these people isn’t just their diversity of interests—it’s their ability to see connections between seemingly disparate fields and transfer insights from one arena to another.

Reynolds uses his entertainment industry storytelling skills to revolutionize how brands market themselves. Fey applies improv principles to business and life philosophy. Branson treats every industry entry as a creative challenge to disrupt “fat and complacent” dominant players.

They don’t just accumulate random experiences—they synthesize them. Each new venture builds on and strengthens the others, creating what you might call a “diversification advantage.”

The Cognitive Architecture Behind It

Here’s where the research gets really interesting. When I dug into what makes some people thrive as multi-passionate entrepreneurs, I found fascinating patterns in how certain minds work.

Some of the most successful multi-passionate entrepreneurs—including Richard Branson, Bill Gates, and the founders of IKEA, JetBlue, and Kinko’s—have been open about having ADHD. This isn’t coincidental. Research shows that adults with ADHD are 300% more likely to start their own business.

The traits often associated with ADHD—divergent thinking, pattern recognition, hyperfocus on interests, comfort with risk, and ability to make unexpected connections—are exactly the cognitive tools that fuel multi-passionate success.

But you don’t need an ADHD diagnosis to recognize these thinking patterns. The key insight is that some minds are simply wired for exploration, connection-making, and synthesis rather than narrow specialization.

The System Problem

Here’s the tragic part: our education and workplace systems are optimized for linear, sequential thinking. Schools reward sitting still and focusing on one thing at a time. Traditional career advice pushes specialization and “finding your niche.”

But innovation often comes from the intersections—from people who can see patterns across fields and apply insights from one domain to solve problems in another. The same mind that struggles with traditional structure might be exactly what’s needed to build something entirely new.

Many multi-passionate entrepreneurs don’t choose entrepreneurship—they escape into it. They leave environments where their curiosity was seen as distraction, their energy as hyperactivity, and their wide-ranging interests as lack of focus.

The Reframe That Changes Everything

What if we stopped seeing multi-passionate minds as “unfocused” and started seeing them as “cognitively diverse”? What if a person’s inability to pick a lane is seen as the superpower that it is - the ability to synthesize disparate concepts?

The most groundbreaking innovations often come from unexpected combinations. The iPhone merged a phone, music player, and computer. Airbnb combined hospitality with peer-to-peer sharing. Netflix fused entertainment with data science.

These breakthroughs require minds that can see across boundaries, not just within them.

What This Means for All of Us

You don’t need to be diagnosed with anything to benefit from this insight. If you’ve ever felt like you don’t fit the traditional mold—if you’re energized by variety, if you see connections others miss, if you get bored by routine—maybe the problem isn’t you.

Maybe your brain was never meant to sit quietly in someone else’s system. Maybe you’re here to build your own.

The next time someone tells you to “focus” or “pick one thing,” remember that some of the most successful people in the world became successful precisely because they refused to do either. Their secret wasn’t learning to say no—it was getting really good at saying yes in ways that built upon each other.

In a world that’s increasingly complex and interconnected, we might need more multi-passionate minds, not fewer.

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Hi 👋 I’m Katie and I have A LOT of different interests. I also enjoy connecting the dots between seemingly disparate topics.

Ready to tumble down more rabbit holes with me? 🐇

Like Alice choosing to follow the white rabbit or Neo taking the red pill, there’s something magical about choosing curiosity over comfort. Each week, I explore the unexpected connections that shape our world, from multi-passionate entrepreneurs to sneaky artists, from improv rules to business empires.

These explorations don’t just satisfy curiosity—they expand how we think about success, creativity, and what’s possible when we follow where wonder leads.

Hit subscribe and let’s see what curious corners of the world we discover together. After all, the best adventures start with a simple decision to follow where wonder leads.

Kindergarten faces smiled back at me, announcing ambitions to drive ice cream trucks and be Hans from Frozen (yes, the villain). The years flipped by: police officer, engineer, YouTuber, nail salon owner, singer/fashion designer, judge, lawyer, interior designer. Dreams ping-ponging like creative brainstorming sessions.

But this time, something deeper hit me. These weren’t just evolving aspirations—these were faces I barely recognized. Somewhere in that scroll from five-year-old to sixteen-year-old, I realized I was looking at young adults I could actually envision as grown-ups.

And that’s when it struck me: those little kids are gone. Not grown up—gone. They evolved into a distinctly different versions of themselves.

The Weight of Escaped Time

People say “time flies” like it’s a cheerful thing. “Time flies when you’re having fun!” But there’s another kind of time flying—the kind where you realize that time isn’t just moving, it’s escaping. Taking irreplaceable moments with it.

The five-year-old who wanted to drive an ice cream truck? She’s gone forever. The version of my kid who believed becoming a Disney villain was a viable career path? That person doesn’t exist anymore, except in a photo and in the corner of my heart that aches a little when I remember.

This isn’t unique to parenting. It’s that universal pang you feel looking at any old photo—a friend who’s moved away, a grandparent who’s passed, a version of yourself you barely recognize. The realization that whatever made that specific moment special can never be recreated because it’s lost to time.

For me the best way to confront my feelings is to get it out of my head and onto the canvas.

When Sadness Shapes Design

The image came to me immediately: a clock dissolving into birds, time literally taking flight and escaping. Not the happy, carefree flight of celebration, but something more melancholy—fragments of moments spreading their wings and disappearing into the distance.

I knew this needed to be stark. The emotional weight called for a silhouette design, something that matched the gravity of what I was feeling. No cheerful colors, no decorative flourishes—just the essential truth of time escaping rendered in simple, powerful shapes.

The clock and crows came together easily, birds getting smaller as they receded, carrying away pieces of time I could never get back.

Then came the words, and that’s where everything got complicated.

When Personal Stakes Meet Creative Struggle

“Time flies” should be simple to letter, right? It wasn’t.

I started with cursive—something that felt nostalgic, matching the bittersweet mood. But no matter how many times I redrew those flowing letters, they felt wrong. Awkward. Like they were fighting the illustration instead of supporting it.

I tried block letters. Then cursive for the first letters only. Each attempt felt further from what this piece needed to say.

Maybe it was because this illustration mattered so much. When you’re creating something therapeutic, something that’s helping you process a real emotion, the creative stakes feel higher. Every element has to earn its place.

After multiple failed attempts, I did the smartest thing possible: walked away. Knowing I’d return tomorrow with a fresh perspective.

The Breakthrough

When I came back, I abandoned everything I’d tried and experimented with a completely new lettering style. Drew the letters in black, added white details, and thought, “Better.”

Then a random idea: what if instead of adding white details, I used an eraser to create transparency? Let the background show through the letters themselves?

That was the moment everything clicked.

The funny thing? This new typography didn’t match the Roman numerals on the clock at all. Logically, I should have chosen lettering that echoed that classical feel. But sometimes logic isn’t the point. It looked right, it felt right, and in a piece about accepting that time escapes despite our best efforts to control it, maybe it was perfect that the letters refused to follow rules too.

Beauty in the Fleeting

Working on this illustration reminded me that some of our most meaningful creative work emerges from processing difficult emotions. The sadness of realizing those little kids are gone forever needed somewhere to go, and art became that container.

But here’s what surprised me: the creative process itself became a counterpoint to the melancholy. While the subject matter was about time escaping, the actual making became about time well spent. Experimenting with new techniques, playing with transparency effects, discovering approaches I’d never tried before.

It’s a reminder that moments are fleeting—including creative moments. That afternoon spent struggling with typography, that breakthrough with the eraser technique, that satisfaction of finally seeing the piece come together—all of it will become memory too.

Maybe that’s the real lesson. Yes, time flies away from us, carrying irreplaceable moments into the past. Yes, it’s heartbreaking to realize that the people we love are constantly changing, that versions of them disappear even as new versions emerge.

But it’s also beautiful. Beautiful because it reminds us that our current reality—whatever we’ve come to accept as normal—is temporary and precious. Beautiful because it pushes us to pay attention, to be present, to appreciate what we have while we have it.

The clock dissolves into birds not just as a symbol of loss, but as a reminder: this moment, right now, is flying too. The question is whether we’re awake enough to notice its wings.

Have you ever looked at an old photo and felt that pang of “that moment is gone forever”? What was it that made that particular slice of time feel so precious and irreplaceable? I’d love to hear about your own encounters with beautiful, escaped time.

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Every time drops a new video, I get excited because I know I'm about to be educated in a topic that I not only know nothing about, but also I've never even really thought about before. If you don't know Ken, you should check out his Substack because it's fascinating. He's a clothing designer and owns a fashion brand, Front of Office. But his content is always about the R&D of garments—often focusing on the culture behind design and manufacturing methods.

His latest video is about who benefits from organic cotton products and why we should all care. In the video he talks about how because of the size and demographic of his followers, he is able to influence change within his industry.

And that got me thinking about how some brands have found success at selling an ethos rather than a product. In other words, they earn money by selling a certain product or service, but they attract and retain clients because of their purpose. What they're known for is influencing culture, politics, or discourse in a seemingly unrelated but tangential sphere. In Ken's case, the ethics and economics of the fashion industry.

And that got me thinking about a brand that I have long been fascinated by—Red Bull. Why am I fascinated? Because I find their business model to be so unorthodox that it's actually genius.

Now, I'm old enough to remember when Red Bull was just an energy drink. I spent many nights in the discotheques of Europe slamming Jagerbombs while dancing the night away—it still makes me shudder when I think about the inevitable extreme heart palpitations afterwards. Yes, I was young and stupid.

Then at some point Red Bull realized that their "gives you wiiings" slogan was closely aligned with the ethos of extreme sports, despite the fact that their actual customer base were just regular people who wanted a caffeine fix—particularly students and gamers.

Despite the obvious inconsistency between ethos and lived experience of the consumer, Red Bull managed to become synonymous with extreme sports. And then esports became a thing and all of a sudden this brand who had long been an event and athlete sponsor could sponsor the types of events (gaming) and people (gamers) that have always been their core demographic. You might think what a lucky coincidence—but in actuality this luck was very much manufactured. They had been sponsoring extreme sports events for decades, building this playbook of creating experiences and cultural influence. When esports exploded in the 2000s and 2010s, they simply applied their existing strategy to events and athletes that actually aligned with their real customers.

So the question is: how did they do it?

How Red Bull Built a Business Model Out of Thin Air (and Caffeine)

Most brands market their products. Red Bull markets a worldview. That's why their business model looks confusing at first glance: they don't just sell energy drinks, they sell adrenaline, performance, and belonging.

Here are the pillars that make them so unique:

They created a category, not just a drink. When Red Bull launched in Austria in the late '80s, "energy drinks" didn't really exist in Western markets. Instead of fighting Coke and Pepsi head-on, they invented a new lane—one where they could charge a premium for an 8oz can.

They invest in culture, not ads. Rather than pouring money into TV commercials, Red Bull poured money into events, teams, and athletes. Flugtag (flying contraptions), Rampage (mountain biking), and cliff diving weren't just stunts—they were brand experiences. Eventually they owned entire sports teams and stadiums, making Red Bull the culture, not just the sponsor. Many of these events are free—I've been to several in my hometown of Vancouver, Canada. And all of them had a few things in common: they were fun, they were memorable, they invoked a sense of community, they did NOT feel salesy—although free Red Bull drinks were readily available.

They built a media empire to tell their own story. Red Bull Media House produces films, documentaries, and streaming content that rivals traditional networks. Felix Baumgartner's space jump wasn't a commercial—it was an event that millions chose to watch. That kind of marketing can't be skipped or blocked.

They aligned with their real demographic. The irony is that extreme athletes aren't the ones buying most of the drinks. It's students, professionals, gamers, and club-goers. By sponsoring esports and gaming events, Red Bull didn't "get lucky." They recognized that their lifestyle message ("gives you wiiings") aligned perfectly with the situations where their gaming customers already lived: late nights, high stress, peak performance. They didn't invent esports, but they were one of the first major global brands to treat it seriously—and that played a big role in esports becoming a billion-dollar industry today.

They made marketing the product. Red Bull doesn't make money from sports or esports. They make money selling cans. But the halo effect of owning culture keeps people buying. Their "ads" are so good, they don't feel like ads at all—they feel like the culture you want to belong to.

👉 The result? Over 12 billion cans sold in 2024 and a company that turned an unremarkable sugary drink into a global cultural movement.

In short, they are marketing geniuses.

What struck me most about diving into Red Bull's strategy is how much it mirrors what Ken Sakata is doing on a smaller scale - both brands have figured out that the real magic happens when you give away valuable content that's separate from your product but aligned with your values.

Where This Rabbit Hole Led Me

Red Bull and Ken are both successfully using different flavors of the same, rare, marketing playbook - proving that it can work for smaller brands and huge global corporations alike. I think there's an opportunity here to learn from this way of getting your brand noticed while staying true to your ethos: give away something valuable for free and build culture alongside customers.

In some ways, I think I’m drawn to both of these brands because in addition to providing something of value for free, they are also asking us to see the world a little differently. In a world that has become very divisive where everyone's media sphere is an echo chamber, I think we could all benefit from seeing our world through new lenses.

As someone who owns two distinctly different businesses (business strategy consulting and illustration), this gets me thinking about my own marketing strategy. How can I leverage my ethos to build community? What can I learn from the Ken Sakatas and Red Bulls of the world?

Hi 👋 I'm Katie and I have A LOT of different interests. I also enjoy connecting the dots between seemingly disparate topics.

Ready to tumble down more rabbit holes with me? 🐇

Like Alice chasing the White Rabbit or Neo following his curiosity into uncharted territory, subscribing means you're choosing to see how deep these weekly explorations can go. Each rabbit hole I share might just expand your mind in ways you didn't expect—connecting dots between art and psychology, design and neuroscience, or whatever fascinating tangent catches my attention next.

Hit subscribe and let's see what curious corners of the world we discover together. After all, the best adventures start with a simple decision to follow where wonder leads.

Picture this: It’s early October and I'm sitting at my desk, staring at a content calendar, trying to figure out how to make my astronaut cat illustration fit into spooky season.

My art? Bold colors, nerdy space themes, terrible puns, and Pacific Northwest landscapes. Halloween content? Orange and black witches and pumpkins.

The disconnect was laughable, but there I was, spending an hour trying to force my work into arbitrary seasonal boxes because that's what all the creative business advice told me to do.

Here's the kicker: I run a successful strategy and operations consulting firm. I help other businesses streamline their processes, eliminate inefficiencies, and focus on what actually moves the needle. But somehow, when it came to my own illustration business, I'd thrown all of that expertise out the window.

I was treating my creative work like it existed in some magical realm where normal business logic didn't apply.

The Day I Became My Own Client

The breakthrough came when I realized I was feeling completely scattered—exactly like the business owners who come to me for help. So I did what I always do: I stepped back and treated this like any other consulting project.

I sat down and asked myself the same questions I'd ask a client: What's not working? Where are you wasting time? What systems and structures do we need to put in place?

The answers were embarrassing. I was approaching my illustration business like it was fundamentally different from any other business, despite having years of experience helping companies solve these exact problems.

Once I started applying the same frameworks I use with consulting clients, everything changed.

How Business Strategy Transformed My Creative Process

Project Management Became Personal Workflow Management Instead of scrambling to create content on the fly, I mapped out my entire creative pipeline. When do I need to start a new design to have it ready for social media? How can I batch similar tasks together? I built workflows that connect seamlessly—from sketch to finished piece to marketing content—just like I do for client projects.

Operational Reporting Became Creative Business Intelligence I started tracking my own patterns the way I analyze team capacity for clients. Which illustrations get engagement versus which ones flop? Where are the bottlenecks in my process? What's actually profitable versus what just feels productive?

The data revealed something surprising: my quick "throwaway" sketches often performed better than pieces I'd labored over for hours.

Change Management Became Strategic Pivoting When I need to adapt my style or approach new markets, I treat it like organizational change management—for a team of one. The same frameworks that help clients navigate transitions work perfectly for creative evolution.

Automation Became My Secret Weapon Every efficiency tool I recommend to consulting clients became crucial for my art business too. AI for audience research and product descriptions, scheduling tools for social media, automated workflows for repetitive tasks. Anything that could be systemized got systemized.

The Content Calendar Disaster

But the biggest transformation came when I tackled the social media nightmare.

I was spending countless hours a month trying to create content calendars around holidays and trending topics. Halloween posts, Valentine's Day themes, Christmas graphics—none of which had anything to do with my actual work. It was absurd.

I was posting things I wasn't proud of, engaging with content that felt forced, and constantly scrambling for ideas that fit someone else's calendar instead of my own creative vision.

The Property Owner Mindset

Everything shifted when I heard on a podcast talking about what he'd do differently if he started his creative business over. He described how much time he'd wasted building audiences on social media—people he didn't really know, couldn't contact directly, and could lose instantly if algorithms changed.

His analogy hit perfectly: it's like renting from a landlord and investing in renovations, only to lose everything when rent gets too expensive. Versus buying your own property and building something that actually belongs to you.

"Build on your own property," he said.

That's when I made the strategic pivot to Substack as my primary content channel. But here's where the business thinking really paid off—I didn't just randomly start writing. I reverse-engineered the entire approach.

Who's my target audience? People who might license my work, buy prints, or other artists building community. What do they actually want to read? What would provide genuine value rather than just promotional noise?

The Beautiful Simplicity of Systems

Now I write one substantial Substack post weekly. Then I take the same image I'm sharing there and create a social media post that goes live shortly after the newsletter. Everything is scheduled in advance. The only additional social posts I do are when I release a new design—which happens regardless of what day it is or what holiday is coming up.

No more scrambling for holiday content that has nothing to do with my actual work.

The irony is perfect: by treating my creative endeavor like a business, I freed up exponentially more time for actual creation.

What Success Actually Looks Like

Here's what most of us miss when we're starting businesses: we get so caught up in following everyone else's playbook that we forget to define what success actually means for us.

You don't need to post daily if weekly works better. You don't need to offer 47 different product variations if three bestsellers generate most of your revenue. You don't need to say yes to every client inquiry if half of them aren't a good fit anyway. You don't need to hire a team if you're happier and more profitable working solo. You don't need to expand into every possible market if your current niche is thriving.

The beautiful thing about running your own business is that you get to decide what "enough" looks like. You just need to figure out your actual goals, then reverse-engineer the most efficient path to get there.

For me, that meant recognizing that my consulting skills weren't separate from my creative work—they were exactly what my creative work needed to thrive.

The Confession

Here's what I'm slightly nervous to admit: I would genuinely love to quit almost all social media. Instagram, Facebook, Twitter—I'd delete them tomorrow if I could.

I dislike social platforms way more than the average person, and as a business owner, they still feel necessary. But honestly? I'm not sure if that's actually true or if I've just convinced myself it is.

The obvious experiment would be to stop posting entirely and see what happens. I'm not quite ready for that leap, but only because the current system is so low-maintenance. Since everything flows from Substack now, social media has become a 10-minute afterthought rather than a constant source of stress.

Maybe that's the real lesson: you don't have to love every aspect of running a business, but you can definitely make the parts you dislike as painless as possible.

Your turn: What's one administrative task in your work that you could automate or streamline this week to buy yourself more time to focus on the part of the work that you genuinely enjoy?

Leave a comment and let me know—I'd love to hear about your own experiments with working smarter, not harder.

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This week's rabbit hole 🐇 🕳️

I stumbled upon this post by & I was really drawn to the final image of the concentric rings that morph into a curve. Because we all know how much I love a good pattern.

That visual pull sent me down a rabbit hole searching for more concentric pattern art, which is how I discovered an artist on Instagram, Jeff Tansey (who uses the handle plotbotstudio). And I became totally captivated by his mesmerizing videos of textured acrylic patterns being painted. I love the way he blends precision with artistry.

Turns out watching this sort of art in action is highly meditative. It was the most serene 2 minutes of my day.

This got me thinking about the little zen garden that I keep in my office & how I find it calming to use the various rakes and stamps to create symmetrical patterns in the sand.

Which got me wondering why these sorts of concentric designs make me feel calm. It's not just that I find them aesthetically pleasing, they actually have an impact on my nervous system.

So I did a bit of research and quickly discovered there is a whole field of study around pattern psychology. Apparently humans are genetically hardwired to find symmetry pleasing & reassuring particularly when curving shapes and a neutral color palette are involved - which explains why I was so drawn to that illustration by PosterLad because it checks all those boxes.

I also learned that interestingly, too much symmetry can actually cause feelings of boredom or disengagement. This is why there is a core tenet in Japanese aesthetic principles called fukinsei (不均整), which requires the use of asymmetry or irregularity in order to create balance in a composition. In short symmetry with a hint of irregularity will invoke a sense of calm, but not boredom. The opposite is also true - using vivid colors in combination with bold angular shapes can invoke a feeling of being energized.

If you want to dive deeper, I've shared a few resources that I find interesting below 👇

https://europeblog.milliken.com/can-patterns-influence-our-emotions

https://science.howstuffworks.com/why-do-get-so-much-pleasure-from-symmetry.htm#google_vignette

https://www.presentationzen.com/presentationzen/2009/09/exposing-ourselves-to-traditional-japanese-aesthetic-ideas-notions-that-may-seem-quite-foreign-to-most-of-us-is-a-goo.html

As someone who loves illustrating patterns, this has given me a lot to think about. I'm looking forward to incorporating these ideas into my pattern illustration practice.

Hi 👋I'm Katie and I have A LOT of different interests. One of my favorite hobbies is connecting the dots between seemingly disparate topics.

I'm testing out this new "rabbit hole" format, and your feedback will help me decide whether to keep going with it. If you found yourself getting pulled into this exploration of patterns and psychology—or if you just enjoyed the ride—give this post a like or let me know in the comments. I have no shortage of curiosity adventures to share, but I want to make sure they're resonating before I commit to making it a regular thing.

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Now, before you grab your pitchforks—I'm not throwing shade at other artists. Art is wildly subjective, and there's no such thing as creating something that everyone will love. But after nearly two decades of calling Vancouver home, I kept finding myself walking by souvenir shops thinking, "I love this city, but I wouldn't wear any of this."

So I decided to create the local pride gear that I actually wanted to wear. Namely a big bold typography print worthy of the back of a hoodie.

The Library That Changed Everything

But here's where this story gets interesting. Before I even touched that design, I did something that felt like overkill at the time: I created a letter library.

After taking a lettering course a few months back, I went through the entire alphabet and drew 9 versions of every single letter. That's 234 individual letters, each with its own personality. Blocky ones, cursive ones, angular ones—the whole range.

At the time, it felt like homework. Maybe even a little excessive.

But when I finally sat down to create my graffiti-style Vancouver typography…pure magic. Instead of staring at a blank page wondering how to make a "V" that felt cool and gritty, I had this whole buffet of options. I could flip through my library and think, "Oh, I want the V to look like this and the O to look like that."

What could have been hours of creative paralysis became a fun puzzle of mixing and matching.

When Everything Goes Wrong (Twice)

Of course, nothing creative ever goes smoothly.

First disaster: I got to the very end of the design—feeling proud and accomplished—only to realize I'd built the entire thing on a 3000x3000 pixel canvas instead of the 7500x7500 I needed. Basically, I'd created something that would look great on a postage stamp but terrible on a hoodie.

I had to start from scratch, and embarrassingly this is not the first time I’ve made this mistake.

Second disaster: Even after rebuilding it perfectly, I discovered the design looked amazing on every color except black. Half the letters just disappeared into the background. Cue more trial and error, adding white outlines, testing on different colors until I found a solution that actually made it look as good, if not better on dark backgrounds.

Here's what I learned during those frustrating moments of rebuilding and problem-solving: having that letter library didn't just save me time—it saved my sanity. I wasn't starting with a blank page and a panic attack. I was working with familiar building blocks.

The Shortcut That Isn't Really a Shortcut

The funny thing about calling my letter library a "shortcut" is that it wasn't actually faster upfront. Those 234 letters took well over a month to create. But every design since then? So much easier.

I've applied the same white outline technique to other pieces now, including a Vancouver skyline design that ran into similar background issues. Because I'd already solved that problem once, I knew exactly how to handle it.

And I've learned something about my own style preferences too—turns out I gravitate heavily toward those blocky letters rather than the cursive ones. Good to know for future library expansion.

Building Your Creative Infrastructure

The bigger lesson here isn't really about letters or even design. It's about building systems that make your future self's life easier.

That letter library? It's my creative infrastructure. Instead of reinventing the wheel every time I need to hand-letter something, I've got a foundation to build from. It's like having a well-stocked kitchen versus trying to cook a meal when your pantry is empty.

And I use the same approach to building repeatable, reusable systems in my consulting work too. Whenever I’m creating a deliverable that I haven’t built before I always add a step at the end to reverse engineer it to create a generic template that I can repurpose in the future. If it’s complicated, I’ll sometimes make a loom video walking through all the steps required to create a quality final product - which I of course link to in the template. This saves so much time and mental load the next time I have to create something similar. I always say it’s a gift for tomorrow Katie.

Sure, building these systems takes time upfront. But the payoff isn't just efficiency—it's confidence. When you know you have tools and solutions ready to go, you're more willing to take creative risks and push through the inevitable frustrations.

The Vancouver design that was supposed to be "just for the back of a hoodie" ended up teaching me more about my process, my preferences, and my problem-solving abilities than I expected. And it all started with doing what felt like unnecessary homework.

Now I've got a brand spank’n new design that actually makes me proud to rep my city—bold, gritty, and cool enough that I'd genuinely choose to wear it. Plus a creative system that's already paying dividends on every project since.

Sometimes the best shortcuts are the ones that don't look like shortcuts at all.

I'd love to hear about the systems and shortcuts you've built that ended up saving your butt later.

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I fall firmly in the "love them" camp. And I think the reason why has less to do with the jokes themselves and more to do with a sweaty, terrifying, and completely invigorating theater I spent most of my weeks in as a teenager.

I used to do improv. Before every show, my whole team would pile into my parents' house for pizza, and then we'd head to the theater. Without fail, the pre-show nerves would hit me, and I'd get sick. We quickly learned this was actually a good thing. On the nights I got sick, we crushed it. The one night I felt totally calm? We bombed. Hard. My team's ridiculous conclusion was that my throwing up was basically a requirement for a good show.

What I realize now is that the nerves came from a place of respect—for the audience, for my team, and for the creative energy in the room. Once the stage lights came up and the house lights went down, that terror always melted into something magical. The key to improv isn't just about being funny; it's about mental agility. It's about taking whatever gets thrown at you—"You're a pirate at a dental convention!"—and instantly finding the unexpected angle that makes it work. Improv trains your brain to spot connections that aren't obvious, to see potential where others see randomness. You learn to flip ordinary situations into something surprising.

So what does any of this have to do with the illustrated puns I create as an artist? Everything.

The same mental muscle that makes improv work is the one that makes a pun land. The magic, in both cases, comes from seeing a familiar thing in a completely new light. A good improv scene takes an audience suggestion and spins it in a direction nobody—not even the person who yelled it from the crowd—could have predicted. A good pun does the exact same thing with language. It takes a phrase you've heard a thousand times and suddenly twists it into something unexpected—like noticing that two crows fall short of being a murder, which makes them an "Attempted Murder.”

This is what I think the people who hate puns are missing. The beauty isn't necessarily the groan-worthy joke itself. It's the intelligence behind it. It's the flash of wit required to see a hidden connection that's been sitting in plain sight all along. A few years ago, when I was really sick, a friend sent me "Have a Little Pun" by Frida Clements. Page after page, it gave me much-needed belly laughs. Even if you don't find the joke funny, you have to admire the brain behind the wordplay.

As a Vancouver-based artist, most of my work celebrates the Pacific Northwest—the mountains, the rain, the wildlife that makes this place feel like home. But I also can't resist creating pun illustrations, even though they always feel slightly disconnected from my more "serious" regional pieces. There's this nagging voice that whispers maybe puns are too unserious, too silly for someone trying to establish themselves as a real artist.

But I've discovered ways to bridge that gap. My "Attempted Murder" features the crows that are everywhere in Vancouver. That otter taking a coffee break? Otters are as Pacific Northwest as it gets. These puns aren't separate from my sense of place—they're another way of celebrating it.

Still, I'll be honest: nobody's buying my pun art. My Vancouver landscapes get attention, but the wordplay pieces? They sit quietly in my online shop, admired mainly by me. I've printed so many of them that they cover the walls of my house, my shower curtain, everywhere I look. I love seeing them there, but I'm definitely still searching for my audience.

And that brings me to the bigger struggle that I think many creative people face. We put pressure on ourselves to be "serious" in order to be taken seriously. We second-guess the parts of our work that feel too playful, too niche, too weird. Getting noticed as an independent artist online is incredibly difficult without a big marketing budget, and it's tempting to stick only with what seems to have broader appeal.

But I keep coming back to those improv lessons about the appeal of surprising your audience by taking the art in an unexpected direction. What if the answer isn't to abandon the things that make us unique, but to trust them more?

I believe there are people out there who will appreciate pun art—fellow nerds who see the intelligence in wordplay and smile at weird pickle-themed art. I just need to trust that if I keep putting my ideas out there, sharing them far and wide, eventually my work will find the right people. After all, every time I look at my portfolio, I'm reminded that at least one person in the world thinks this stuff is brilliant.

Ultimately, life is too short to pretend to be something you're not. There is no such thing as art that's universally admired, so I might as well create things that I genuinely love. In short, I’m just gonna let my weird light shine bright, so the other weirdos know where to find me.

The great pun debate: where do you stand? Are you a lover or a hater? Tell me why in the comments!

Not in a morbid way—more like a clarity exercise. If my entire life had to be boiled down to a single sentence carved in stone, what would I want it to say? After a lot of consideration, I've landed on this: "Now that bitch knew how to live!"

(And yes, I plan to be cremated, so the whole tombstone thing is theoretical. But the sentiment stands.)

What does that sentence mean to me? Well if folks are saying that about me after I’m gone, it means that I never settled for living the life that others expected me to live. I wasn’t afraid to try new things, or go after goals that mattered to me. And the bitch part? That just means that I didn’t take shit from anyone along the way.

So what sparked this meditation on mortality and meaning? Well, I'm a few years shy of 50, which means I've had a front-row seat to watch my parents' entire generation navigate retirement. And what I've observed has fundamentally changed how I think about building a life worth living.

The Golden Years Fallacy

The conventional wisdom goes something like this: Work really, really hard so you can save for retirement. Sacrifice your best years building a nest egg so that in your golden years, you can finally ride off into the sunset and do all the things you've been dreaming about.

It sounds reasonable. Responsible, even.

But I’ve watched too many people cross that finish line only to find the dream was a mirage. They discovered that those grand travel plans are harder to swing on a fixed income without company benefits. The hobbies they fantasized about for years—hiking, kayaking, exploring new cities—are a lot easier on the body at 45 than at 75. And most painfully, I've seen health issues appear unexpectedly, changing everything in an instant.

The reality for many is that retirement looks a lot like their pre-retirement life, just with less income and more doctor's appointments. It’s not the adventure they were promised. And it’s definitely not the life I want for myself.

My Philosophical Guides

This realization sent me searching for a different way to think. I’ve always loved philosophy, and a book that genuinely changed my life is Alan Watts’ The Wisdom of Insecurity. The core message: if you spend your life perpetually thinking about the past or building for the future, you're always missing the only thing that’s real—right now.

But my other great philosophical guide is a little less traditional: Ferris Bueller

I know that sounds ridiculous, but hear me out. That movie was supposedly made for teenagers, yet it always felt to me like the story of someone going through a midlife crisis, just told through the voice of a 17-year-old. "Life moves pretty fast. If you don't stop and look around once in a while, you could miss it." That's not typical teenager wisdom—that's something you usually don't grasp until much later in life.

Now Ferris is definitely a flawed character - he’s cocky, selfish and unperturbed by consequences - but I suppose, what teenager isn’t. But what I love about him is the way he makes the most of his unearned confidence and his ability to live in the moment. He knows exactly what the consequences are if he gets caught, but while every other high school student is just trying to get through the school year, he's focused on the present reality that his childhood is about to end, his best friend is going to move away, and he willing to take risks in order to hold on to this moment as long as possible.

The most famous scene in the movie is when he charms his way onto a parade float and sings to a very enthusiastic crowd. It’s memorable because it’s audacious. He didn’t have the credentials to be up there, but he did it anyway and he was celebrated for it. Audiences love that scene because deep down we all want the courage to truly live in the present tense.

So I started asking myself: what would it look like to live with that kind of present-tense courage, minus the teenage recklessness?

The Real Cost of Waiting

We're constantly told that the biggest risk to our future selves is not saving enough money for retirement. But I think we've got it backwards. The real risk isn't running out of money—it's running out of time, energy, and health. You can always find ways to make more money if you need to, but when your time is up, it's up. That's what the conventional "work now, live later" model actually costs us: the irreplaceable present moment, and the physical and mental capacity to fully live in it.

But there’s another hidden cost to putting everything off. The idea of "someday" keeps our dreams vague and fuzzy. It’s easy to say, “I’ll travel when I retire.” It’s much harder to answer the real questions: Where do I want to live? What activities do I want to do? Who do I want to spend time with?

Getting crystal clear on these questions has been a game-changer for me. It’s transformed my hazy fantasy into a concrete goal I can start moving toward now, instead of treating "someday" like a magical date when life begins.

My Experiment in Present-Tense Living

So, what does this look like in practice? I still run my business strategy consulting firm, but I’ve started building a creative business on the side, licensing my illustrations. I don't expect it to replace my consulting income, but it's work I love, and the goal is to create a stream of revenue that can fund more of our "someday" adventures while I gradually scale back my other work.

And my husband and I are done waiting. Our kids are teenagers now, old enough to be left on their own for a bit. I’ve always dreamed of visiting Singapore, so we booked a week-long trip for this fall.

It’s a small step, but it feels like we’re reclaiming control, pulling a piece of our future into the present.

Let's Talk About the Money

I know what some of you are thinking: "That's irresponsible. What about security? You should be maxing out your retirement savings. You can't count on art to pay the bills."

Believe me, my husband and I have had this conversation. We've always been frugal. We live in a modest house and drive our cars until they give out. But at a certain point, you have to ask yourself: how much is enough? Once you have a solid foundation, does it make sense to keep hoarding resources for a future that’s not guaranteed, at the expense of the life you have today?

This shift might mean we downsize our home earlier than planned or make other trade-offs down the line. But those are trade-offs we're willing to make to build a life we love.

The Agency Most People Don't Realize They Have

I recognize that even having conversations about these kinds of choices comes from a place of privilege. Not everyone has the luxury of choice I'm describing. But I also think most people have more agency than they give themselves credit for.

The point isn't that my way is the right way. It’s about consciously designing your own life. It starts with asking what you truly want and then looking honestly at the trade-offs you’re willing to make to get there. It’s about giving yourself permission to question the timeline and assumptions you’ve been handed.

As one of my other favorite philosophers, Henry David Thoreau, said “ Go confidently in the direction of your dreams. Live the life you've imagined”

A Different Kind of Finish Line

So at age 47, I’m taking day trips by ferry to nearby islands for lunch, and I’m spending a little less time behind my keyboard and a little more catching up with friends.

And in a few years, when my kids are in college, I’ll travel more while continuing to consult and illustrate. So that by the time my body forces me to slow down, I'll be ready and happy to do so—because I'll have been living intentionally all along.

Alan Watts and Ferris Bueller were right. The only moment we’re truly guaranteed is this one.

So, how are you going to spend it?

I was a student on a work term, the most junior person by a long shot, working as a field service technician for a company that made high-tech lasers. These weren't sci-fi lasers; they were incredibly precise machines used to drill circuit boards for cell phones. And a critical unit had been down for days.

The client was furious despite our best attempts to fix the issue. By this point, all of our senior technicians—some with PhDs in electronics—had tried and failed to fix it. We had even flown an expert in from another country. But the machine remained stubbornly broken. The mood was tense.

In the small break room, the technicians debated the problem. I listened quietly and then asked, "Should I take a look at it?"

A few people chuckled. The message was clear: If we can't fix it, what makes you think you can?

"Well, nobody's had any success," I countered. "So why not have a new set of eyes on it?"

They shrugged. What was there to lose?

Twenty minutes later, I walked back into the breakroom. "It's up and running," I said.

Silence. Then disbelief mixed with outrage. "No way! There's no way you fixed it."

We all walked back to the machine, and there it was, humming along perfectly. They were stunned. And frankly, so was I, but for a completely different reason. The solution was surprisingly simple, so I couldn't figure out why it had stumped our best and brightest. I had simply followed the standard procedure for tuning the laser, which involves looking for visual cues—certain lines on a piece of paper—and then fine-tuning with a power meter.

As it turns out, the rule, drilled into every experienced technician, was that it was impossible for the laser's strongest point to be located on one of those visual lines. Their training had taught them to completely avoid those areas.

However, I wasn't aware of that rule. So, I wasn't trained to believe it was impossible.

I just tuned the laser to wherever the power meter gave me the strongest reading. When the highest reading happened to fall directly on one of those "impossible" lines, I didn't second-guess it. I just went with it. And it worked.

That lesson has stuck with me throughout my entire career: the fact that I did not firmly believe in a set of rules meant that I wasn't afraid to play outside of them. My inexperience gave me a freedom the experts didn't even know they were missing.

This brings me to my art.

I'm a self-taught artist, which is a nice way of saying I'm still very new to this. I'm building the plane while flying it—juggling a full-time job while taking online courses and slowly finding my way. And if I'm being honest, it can be nerve-wracking to admit how new I am. It opens the door to the question: Well, then, why should anyone buy your art?

My answer is the same now as it was as a student technician. My value isn't in being the most experienced person in the room; it's in not being afraid to try the "impossible" things.

For a long time, I struggled with traditional art techniques. When I took courses, my work would end up looking exactly like my instructor's. I was learning skills, but it didn't feel like me. The hidden cost of following the conventional path was my own authenticity.

So I started experimenting. The engineering side of my brain loves creating repeatable patterns. So, instead of using traditional brushstrokes for shading and detail, I started using patterns: tiny half-moons, cross-hatches, and diamond shapes. It's less realistic looking, but it feels authentically mine.

My lack of formal training allowed me to invent a system that made sense to me, without anyone telling me it was the "wrong" way to do it.

Of course, breaking the rules comes with its own set of challenges. I've discovered that patterns with very thin lines, like cross-hatching, look great on a canvas but tend to fade on a t-shirt after a few dozen washes. So after a bit of trial and error, I've learned to adjust the thickness of my lines.

But working through the challenges is well worth it, because the upside to creating my own approach is immense. What I thought would be a static set of patterns has become a living part of my creative process. Each new piece of art inspires me to design new patterns. My "unconventional" method has become a source of endless ideas.

The ultimate payoff for breaking the rules is a creative process that generates its own energy, freeing you from the need for outside approval. My goal is to hold onto that feeling I had in front of the broken machine—the freedom to find a solution where others are paralyzed by the rules.

That's the gift of the beginner. While a lack of expertise may hold you back in some areas, in others, it gives you a perspective that the experts may not even realize they're missing. And if you can learn to leverage that, it can become your superpower.

Now, I'd love to hear from you.

If you're an expert in your field, what's one "unbreakable rule" you secretly suspect might be holding you (or your industry) back?

Let me know in the comments below.

Amid that blissful slowness, I found myself thinking about what it means to build a simple life. I pulled out my e-reader, opened one of my all-time favorite books—Jerome K. Jerome’s Three Men in a Boat—called the kids over, and read them one of my favorite chapters.

If you’re not familiar with this book, it's a hilarious story about a calamitous boating trip. It was written over a hundred years ago, but it absolutely holds up. While the book is good for a laugh, underneath the humor is a profound theme about what it means to build a happy life. For years, I’ve been attached to a particular passage from that book that focuses on the idea that we have a lot of choice when it comes to what we decide to carry through life. Jerome writes about the wisdom of letting your "boat of life" be light, loaded only with the essentials for happiness. He gives you a recipe for a good life, and it starts with tossing the unnecessary lumber overboard.

I’ve loved one particular quote for years, and sitting on that beach I realized that I desperately wanted to illustrate it. So once I returned home and finished my self-imposed technology break I did just that.

What I love about this piece isn't just the quote, but what it represents for my own journey. I was shocked to discover that I was able to create this illustration in a single night. A year ago, that would have been unthinkable. A piece like this would have taken me three weeks of agonizing work. I would have endlessly adjusted the colors, fussed over the font, and still not felt satisfied. I struggled for a long time to create things that felt truly and uniquely mine. But suddenly, I felt a sense of confidence and ease that was new.

Upon further reflection, I realized that I’d been throwing some of my own lumber overboard. Being self-taught, I had a tendency to overthink everything, to overcomplicate my work with a nagging perfectionism. That was my lumber—ruminating over minuscule details instead of trusting the overall feel of a piece.

The only way to get rid of that weight was to do the work. Turns out that the "magic" of being good at something isn't magic at all; it's the discipline of showing up. Over the past year, I took courses, practiced almost every day, and started working smarter by building systems, like creating reusable stamps for elements I use often. All that consistent effort was the act of tossing the lumber overboard, piece by piece.

Having thrown all that old, heavy struggle overboard, I was free to focus on the joy of creation. And it really was a joy, I had so much fun creating this illustration and I am so stinking proud of the end result.

There’s a blank wall in my office that has been begging for a new piece of art, and this is what’s going to go there. It will be a reminder that to build a good life—and a joyful creative practice—you only need to focus on what’s essential.

I’d love to hear from you in the comments. This piece was inspired by a quote from a favorite book. What's a book, movie, or song quote that has stuck with you and influenced how you think or create?

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This idea really resonated with me, especially since I'm actively looking for ways to engage with shops, galleries, and the local artist community. The idea of a zine is also very nostalgic for me. Growing up in the 90s, zines were all the rage. My friends and I created a few, but the real joy was finding zines created by others. Some were anonymous, others weren’t, but it was always thrilling to find a new issue lying around at school or a local shop. There was a real sense of community and intimacy in reading a zine you knew was printed at home with virtually zero budget but a whole lot of love. This whole project has felt like a tribute to a younger me, and I’m loving it.

Finding the Rhythm

I decided to create the zines by repurposing my existing Substack articles so I wouldn't have to start from scratch. The first major hurdle was taking a long-form article and condensing it into a much more digestible format. The second challenge was making sure there was enough space for art. A wall of text can be boring, and I wanted to break it up with my designs.

The moment it all clicked was when I created a basic layout and printed it on a single sheet of 8.5x11 paper. I folded it into the correct shape and suddenly, I could see what my idea would look like in the real world. It was a tangible, exciting moment that made me think, "Okay, this could actually be cool."

Working Through the Kinks

Not every idea worked perfectly the first time. My initial instinct was to use my logo as the main image on the cover page. However, after printing a second version, I quickly realized all the zines would look exactly the same. The whole purpose of creating them is to catch someone's eye and get them to pick it up, and a stack of identical covers wasn't going to do that.

So, the logo got moved to the bottom of the cover page, and each new volume will have a unique, eye-catching image that corresponds to the story inside. This small but crucial change reinforced a big lesson for me: to connect with people, the art needs to be visually compelling first. The story comes once they've decided to open it.

I also discovered a quick YouTube tutorial that showed me a much better way to fold the zines. My first attempts were like an accordion, but now they fold like a real magazine.

A Layout with a Purpose

With those minor issues sorted, I ended up with a product that actually looks pretty great. I know I'm a data point of one, but I would 100% pick one of these up if I saw it lying around.

But zine had to serve a purpose beyond just looking good, so I structured the layout with a few things in mind. The front cover has a captivating image and title, and the next five pages tell the story, interspersed with my doodles and drawings. Then there's a page that talks about me as an artist so readers can make a connection with me as a human being. Finally, the back page is a way for them to connect with me. It includes a QR code that links to my Linktree along with a brief description of what they'll find there - namely my website, online shops, and social media.

Once I was happy with the layout, I created two volumes based on Substack posts that I think would resonate with my local audience. I'm focusing on stories that might appeal to shops and galleries, as well as individuals who might want to buy my designs online.

What’s Next?

Now that I have a couple of volumes created, the next step is to put them out into the world. The easy thing would be to simply leave them around town, but the real plan is a bit more intentional.

I'm writing a letter to local shops, cafes, and restaurants that I know already support local artists. The ask is that they agree to keep a stack of zines in a location where customers congregate (like the host stand at a restaurant or the order pick-up area in a coffee shop). I'll provide a stand and a stack of zines, with a promise to refill them whenever they want more. In return, they'll have my goodwill, gratitude, and all the shout-outs on social media and by word of mouth.

Will this work? I'm not sure, but it's a fun experiment - and there’s nothing I love more than a new challenge.

The Main Takeaway

With all the noise online, bringing your art to people where they already are can be a fun and effective way to get noticed. I'm excited to see how this experiment turns out.

What's an unconventional way you get your work in front of people?

I was three-quarters of the way through my university degree and decided to take a year off to work and travel. My journey led me to a backpacker's hostel in Australia, where money was tight and my world was a mix of new faces and shared spaces. One of those faces belonged to a woman who started & ended her day in a cloud of smoke and didn’t stop talking in-between. She was a generation older than me and definitely lived life to the fullest. I enjoyed listening to her stories because she was an absolute vibe.

While we were there, a huge concert was happening, with Ben Harper headlining. My dorm-mate decided she was going, period. It didn't matter that she didn't have a ticket. It didn't even matter that she didn't have money for a ticket. In her mind, it was already happening.

The next day, she told me the story. She went to the concert venue and hopped the fence. Within minutes, she was tracked down by security and promptly escorted out. Undeterred, she walked to a different section of the fence and hopped it again. Again, security found her. Again, she was kicked out. This went on several times—a relentless cycle of intrusion and expulsion.

And then, something shifted. After being caught for the umpteenth time, the security guards just gave up. They were so exhausted by her sheer, stubborn persistence that they decided they just didn't care anymore. They let her in.

Her moral of the story, delivered with the knowing grin of someone who has gotten away with a lot in their life, has stuck with me for years: "Persistence beats resistance."

It's amazing how often I think about that woman, someone I only knew for two nights, and yet her mantra has become a cornerstone of my own business philosophy. Her approach cuts directly through one of the biggest traps we fall into: waiting for the perfect plan. We convince ourselves we need every step mapped out before we can begin, but the perfect plan is a myth. It’s a comfortable form of resistance that keeps us from the messy, unpredictable, and necessary work of actually starting.

My dorm-mate didn’t have a detailed strategy; she had a goal and was prepared to persevere through the inevitable obstacles that stood in her way. She understood that the journey begins not when the plan is perfect, but simply when you decide to start.

With a couple more decades under my belt I know now that every successful endeavor can be attributed partially to luck. But the most successful people I know have a habit of making their own luck through sheer persistence. They start where they are, and they just keep going until eventually, it pays off.

Now I’d love to hear from you.

When did you learn a valuable lesson from an unlikely source & what was it

This is the story of my "Smart Ass" illustration.

Last summer, my daughter and I were in Santorini, Greece. If you've ever been, you know that donkeys are everywhere—live ones trotting by, statues on corners, and pictures in every shop. It was in one of these little shops that my daughter, after an inordinate amount of time sifting through a basket of plush toys, found the one.

It was a ridiculous-looking donkey. One of its eyeballs had been glued on upside down, giving it a permanently bewildered expression. She fell in love, bought it with her own money, and it became her most prized possession of the trip.

In my post a few weeks back I talked about how I kept an illustrated journal during this trip, and the funny little donkey with the crazy eyes made its way into the journal. It's a good thing it did.

A few days later, on the frantic trip to the airport, the donkey was lost.

The tears were immediate and epic. The loss of this tiny memento was a genuine heartbreak. What followed was a whole saga: I called the hotel that booked our taxi. They called the taxi driver. Miraculously, the donkey was in the car! But he couldn't get back to the airport in time before our flight. We even debated having this silly €8 toy shipped to us in Canada for €40—a price my daughter was willing to pay out of her own savings, she was that devastated.

In the end, we had to leave it behind. A genuinely sad and frustrating end to an otherwise awesome vacation.

But because I had that drawing in my journal, we still had a perfect memory of what he looked like.

Separate from all this, a completely different idea had been rattling around in my head. As a former engineer, I'm a sucker for anything related to science and technology—I love finding smart people and learning from them, which naturally extends to a love for "nerd humor."

Now, before we go any further, you should also know that I am an exceptionally sarcastic person, so I am no stranger to being called a smart ass. Frankly, I've always found it to be a bit of a compliment. A smart ass is typically a quick thinker who points out the seemingly obvious thing that others missed. And besides, I’d much rather be a smart ass than a dumb ass!

This got me thinking: what if I created a literal interpretation of the phrase—not a sassy person, but a genuinely intelligent animal. A smart ass.

And I knew just the ass for the job. I would take my illustration of the lost donkey, this source of so much heartbreak, and upcycle the memory. I would turn it into art.

Looking at the finished piece now, it represents something I truly believe: life is a mosaic of good and bad moments, and the way we remember things has as much to do with our attitude as the event itself.

We could have chosen to let the lost donkey be a sad memory. Instead, we turned it into this. We took the heartbreak and the stress and the tears, and we made something joyful. And now, when we think of that donkey with the crazy eyes, we don't feel sad. We just smile.

I'd love to hear from you in the comments:

Tell me about a memory that always makes you smile, but has a surprisingly dramatic story attached to it.

But what if that’s only half the story? The full saying, often lost to time, is actually: “A jack of all trades is a master of none, but oftentimes better than a master of one.”

That second half changes everything. It reframes a supposed weakness as a strategic advantage. And in my experience, it’s the secret to building a creative life and business that doesn't just survive, but thrives.

From the time we're young, we're fed a specific narrative about success. It’s the 10,000-hour rule. It's the pressure to pick a hobby, narrow it down, get the grades, go to the right university, and land the job you’ll have for the rest of your life. It’s a straight line.

But my path has been anything but a straight line. Looking back, I’ve realized my professional life works in cycles. You could call it a seven-year itch.

I started out obsessed with flight. I had my glider pilot’s license at 16 and my private pilot’s license at 17. That led me to aerospace engineering, where I worked on the Canadarm for the Space Shuttle and even did a stint at NASA. After about seven years, the industry slowed, and I felt the itch. I did a complete pivot, taking my technical skills into the world of interactive design for museums and cultural institutions. I was a project manager, blending technology and art to build incredible exhibits.

A few years later, I moved from managing projects to managing the business itself, getting deep into streamlining process and operations. And then, right on schedule, the seven-year itch struck again. I left to start my own operations consulting company, which I’ve been running for seven years now.

And here I am, feeling that familiar pull. Alongside my consulting work, I’ve launched a new creative business, finally giving my love for illustration the space it deserves.

But a path like this comes with a nagging question: How do all these different pieces fit together? It’s one thing to live it, but another to explain how rocket science and museum exhibits all add up to a single creative identity. I was wrestling with that feeling of being a collection of disconnected stories when I stumbled upon a post from cartoonist sharing a drawing by . The illustration showed an old-school projector. In the wide funnel at the top, all of life’s inputs were being poured in—books, songs, movies, photos, experiences. All of it was churned through the machine of experience and skill to produce a single, focused beam called “YOUR ART.”

That drawing hit me hard. Society often makes you feel like you need to narrow that funnel, to pick one lane and stay in it. But I realized that my strength, my inspiration, and my art come from having the biggest funnel possible. All those seemingly disconnected worlds are the inputs that make my output unique.

And my funnel isn't just filled by my resume. It’s packed with hobbies and obsessions, too. I’ve had my ‘learn the ukulele’ phase, my ‘sew all my own clothes’ phase, and my phase of being absolutely determined to perfect the world's best butter tart. (My husband’s colleagues were grateful beneficiaries of the many batches I deemed not quite good enough.) I love to travel, ski, paddle board, read, write, and I even took up sailing for a few years. These aren't distractions; they are just more inputs for the funnel.

The common thread through all of these pursuits—from rocket science to baking—wasn't a specific skill. It was a mindset. A willingness to try, not despite the fact that it’s difficult, but because of it. I get a thrill from the challenge of learning new things - I always say that my hobby is simply finding new hobbies. And because of that, I have never been afraid to suck at something. I fully accept that when I try something new, I will be a beginner - and probably a shockingly untalented one at that. This refusal to be deterred by the messy learning process is, I believe, the single biggest difference between dreaming and doing.

An Unconventional Superpower

So how does this "master of none" approach actually help you run a business?

First, you’re not just selling a skill; you’re selling your story. When I talk to new clients, I'm selling them on my unique blend of experiences—everything in my funnel. They know they’re getting someone who can think creatively and figure shit out when obstacles arise, because my entire career is proof of that. You are the sum of all your character traits plus your skills and life experiences. That’s what you’re selling: a unique perspective that allows you to do the job in a way only you can.

Second, In a world where most people fear change, those who embrace the unknown tend to thrive. The pace of change these days is terrifyingly fast, so being comfortable with being a beginner is a superpower. New tech, new platforms, new skills—no problem! These don’t feel like threats, they just feel like more interesting inputs for your funnel.

Putting Your Superpower to Work

Multi-hyphenate, Poly-math, Jack-of-all-trades, Generalist - whatever you call it, it's good for business. If you want to run your own business, you are signing up to be the CEO, the marketer, the bookkeeper, and the creative director - of course all of this is in addition to being the creator of whatever good or service you’re selling. Make no mistake about it, you have to be willing to become passably good at a wide variety of things to run a viable business. Give yourself the grace to be clumsy and make mistakes. Know that you’re not going to get it right the first time, and that’s the entire point.

Of course, this doesn't mean you have to do everything alone. A smart generalist also knows when to call in a specialist—like a lawyer to review a contract or an accountant to handle complex finances. But the foundational willingness to learn and try is non-negotiable.

So my real advice is this: Go suck at something. Seriously. The goals you're dreaming about are waiting on the other side of that initial, awkward, messy phase of being a beginner. Don't let the fear of not being good enough stop you from becoming great.

I'd love to hear from you in the comments:

What's one new skill you've been hesitant to try because of the fear of being a beginner? I'd love to hear what you're excited (or nervous) to learn next.

How do they decide? How do they take letters of different shapes and sizes and fit them together in a way that looks so... cohesive? The thought process was an enigma to me, a skill set I filed away under "unsolved mysteries" and "not for me."

But my love for typography designs never faded. So, I finally decided it was time to stop admiring from a distance and start learning. I enrolled in a Skillshare course by Vinitha Mammen called "Hand Lettering Practice: 3 Easy Steps to Explore New Typography Styles," hoping it could demystify the magic.

The "Aha!" Moment That Changed Everything

The course lived up to its name. The instructor did a phenomenal job of breaking down a seemingly complex process into the promised 3 easy steps: first proportions, then shapes, then details.

But the real, game-changing unlock for me was learning that nearly every letter can be structured within a simple 5x3 grid. This grid can be stretched or squashed, but as long as that core proportion remains, you can create an endless variety of legible letters that will fit together. It was the logic I had been missing. Suddenly, the magic had a system.

An Experiment in Chaos

Armed with this new framework, I gave myself a challenge. I decided to create a nine letter piece and I set one major rule: every single letter had to be different. A different proportion, a different shape, and a different design detail.

My goal was to explore, but my expectation was unadulterated chaos. I fully expected the final piece to be a hot mess of conflicting styles. With no cohesion between any two letters, how could it possibly look good? I leaned into the glorious chaos.

To my surprise, something kind of cool-looking emerged. Through all the intentional chaos, a strange sense of harmony appeared. It’s not a polished portfolio piece, but it’s proof of a process that works.

The Glorious, Messy, Truth

Of course, the process wasn’t without its struggles. Just ask the letter "E."

I initially styled it as a loose scribble, which I liked on its own. But as I started adding solid outlines and 3D effects to the other letters, the lonely scribble just looked off. I tried adding a solid color behind it, but I couldn't get the colors to work. I tried making the letter solid with the scribble on the inside, and that didn't work either.

In the end, I abandoned the scribble idea altogether, made the "E" a solid letter like the others, and added a new pattern. It was a moment of friction and failure, and if you watch the time-lapse video, you’ll see I spent more time struggling with that one letter than any other.

The Freedom of Being a Beginner

This project taught me a huge lesson: it's foolish to look at another artist's work and assume you could never master the skills to create something similar. My first real attempt at typography is a thousand times better than I ever imagined it could be, and full credit goes to the instructor, Vinitha Mammen. She made the topic incredibly accessible, and she's also an amazing artist in her own right—I highly recommend you check out her work on Instagram.

The creative journey is so much more fun when you're not afraid to step outside of your comfort zone. There is a real freedom in allowing yourself to be a beginner—no expectations of creating something great, just a belief that if you follow the process, the skills will come, and great art will eventually follow.

Now it's your turn!

When was the last time you truly embraced being a beginner? I'd love to hear about a course, teacher, or "aha!" moment that helped you unlock something new.

Every evening, we’d sit down together. While my daughter wrote in her journal, I would open Procreate on my iPad. My goal was to create one drawing a day, illustrating the funny or memorable moments and overlaying them on top of photos I’d taken. As I drew and she wrote, we’d talk about the day—the highlights, the lowlights, and the little things we didn’t want to forget.

What started as a simple daily entry—a trident drawn over a photo of the Temple of Poseidon—slowly evolved. The pages became more elaborate as they filled with the texture of our journey.

For example, my entry from Delphi shows just how layered these pages became. I can still feel the sweltering heat as we climbed what seemed like a bazillion stairs to a church with a stunning view, so an illustration of stairs features prominently in that day's entry. Similarly I captured the word "debacle" —an inside joke from a hilarious word game that had our entire tour group laughing for the rest of the trip. It also features a little "submarine," a memory from a local Mastica tasting I did. These are the details a camera roll would miss, the tiny threads that held the day together.

Then, much later in Oia, another collection of moments demanded to be drawn. There was the saga of the forgotten hat, where I gave mine to my daughter and ended up buying a replacement that has since become my absolute favorite. There was the funny-looking donkey toy with crazy eyes that she adored instantly and has since become the inspiration for another illustration. And it was here, amongst the whitewashed buildings of Santorini, that one of our favorite moments from the whole trip happened.

It all came from a simple, misread sign. We were hot, tired, and probably a little delirious when I pointed to a sign above a bowl of water on the street and said, "That's funny... 'Water for Satyrs'. I love how they are really leaning into the Greek Mythology here" After a trip steeped in Greek mythology, it almost made sense. My daughter gave me a quizzical look, so I looked closer and saw the faded words, clearly meant for the stray cats that roam the island on hot summer days: 'Water for Strays.' We stood there on the street and just howled with laughter. It was such a small, silly thing, but it was our thing. In that moment of shared joy, I realized that the real trip wasn't just seeing the beautiful views; it was this.

This illustrated journal brings back stronger memories than any photo album because it holds the feelings of these moments. Without the drawing of the word "debacle," I’d remember we played a game, but I wouldn’t remember why we laughed so hard. Without the scribble of a hat, I’d forget the lesson I learned in that moment: not to sweat the small stuff. The frustration over her forgotten hat wasn't worth it, especially when it ultimately led to a now cherished object.

This project taught me to lean into the mundane. Creativity is sparked in the small moments that happen between the big life events. On other vacations since, I’ve only taken photos, and looking back, I feel a sense of loss for the small moments I didn't capture. The daily practice of creating that journal made me happy not just in the moment, but looking back on it, too.

And the funny thing about looking back is realizing how my perspective on the work itself has shifted. When I was making these little drawings each day, they didn't feel special. They were just scribbles on photos. But looking back now, this collection of 21 illustrated days feels like one of the most important pieces I've ever created. It’s a snapshot of a truly wonderful experience, held together by all the beautifully insignificant moments that made it whole. It’s a powerful reminder that the big, impressive creative idea isn't always the one that ends up being the most captivating.

It's a lesson I carry with me into my work and life now: Stop waiting for the next big, important moment to come along and start trying to see what's amazing about the current one.

Community Discussion

Now, I'd love to hear from you.

When have you started a creative project that felt insignificant at the time, only to realize its importance later on?

Leave a comment below and share your story.

In reality, I don’t actually believe in instant success. I believe most people we think of as an overnight sensation are just people who worked really hard for many years, often on a disparate set of skills that finally came together at the right moment.

As a business strategy consultant, I’ve worked with many different businesses. And what I’ve learned is that any successful enterprise requires the presence of two powerful, and sometimes opposing forces: creativity and logic. The creative side is the idea - it’s what the business sells. The idea is often a hybrid version of a bunch of experiences, skills and interests of the business founder. The logic side is how to turn the idea into something that you can actually make a living from. This applies equally to a small solo-owned creative business and a Fortune 500 company.

Starting and running my creative business is a constant dance between creativity and logic, and the inspiration for this illustration.

As I sat down to draw I wanted to capture how I was feeling in that moment: happy to be creating, but knowing the logical side of my brain was telling me I had other work to do. I love puns, I love nerds and I love animals, especially those from my home in British Columbia. And thus a nerdy otter bemoaning the fact that he “otter” get back to work was born.

This feeling the otter represents, the tension between creative joy and professional duty, is at the heart of my entire process. To manage it, I've had to be intentional about how I structure my work.

The creative part of my business — coming up with ideas and illustrating is the part that sets my soul on fire. I like to think of this like dessert. Delicious, but not allowed until I’ve eaten my veggies.

The veggies are the business side. It’s setting goals, handling the finances, and putting together a schedule. In other words, knowing what to do with my illustrations once they are complete. I have a whole process: schedule a social post, upload the design to my website along with my Redbubble and TeePublic shops, and document everything in my master tracker—the title, the description, the color palette, where it’s been posted. This information is then logically repurposed for marketing so I never have to start from scratch.

Because I want to maximize the time I have for creating, I have well documented processes in place to streamline as much of this as possible. It also makes it easier to delegate tasks to others - something I’ve yet to do, but once this business is thriving, I will absolutely delegate as much as humanly possible. That’s CEO 101 right there.

And why shouldn’t I dream of becoming big enough that I need to hire someone? My Big Hairy Audacious Goal (my BHAG, as they say) is to be so wildly successful as a commercial artist that I can live and work from anywhere—a winter skiing, a spring by the beach, and a summer in my hometown. How wonderful would it be to create art everyday and be inspired by new places, sights & sounds all while having an assistant (or team) to keep the business running?

If I have any hope of achieving that goal, I’m going to need to set many smaller goals along the way.

And the best place to start is one small goal that is achievable but a bit of a stretch - meaning that I’m going to need to really work at it. My one achievable goal for this year is to get my art featured in a specific local store that I love—a place whose vibe perfectly matches my own. To get there, I created a work-back plan. By the end of the year, I want to have a contract with them to feature one of my designs in their store. That means two months before that, I need to be in conversation with them. And one month before that, they need to know who I am, so I’m not just a cold approach. So I’ll continue creating art that fits their brand, research their online presence, and create content designed to catch their attention. This step-by-step process blends the fun of creative work and structured planning to create a roadmap that I can really believe in.

Ultimately the work is driven by creativity, but logic builds the path to get that art out into the world. Creativity and logic need to work in harmony, because they are equally necessary for success.

In other words, if you want to turn your creative practice into a successful business: Plan the work and then work the plan. Because any goal or ambition you have that doesn't have goals with milestones and actionable tasks assigned to it is just a pipe dream.

So let's turn our wishes into plans together. I'd love to hear from you in the comments:

What's your "Big Hairy Audacious Goal?" And what's one small, logical step you could take this week to move toward it?

So much of the advice for artists and designers today revolves around one thing: trends. We’re told to check Pinterest for what’s hot, to know the popular color palettes, to research what themes people are buying right now. I’ve heard this rule over and over, and I’ve even tried to follow it. But every time I’ve tried to create something just because I thought it would be popular, it has fallen flat. Maybe it looks fine, but it’s missing a spark. It just doesn’t feel like me.

So I decided to break the rule. My strategy is simple: I create things that I want to see in the world. I design for an audience of one. Because let’s face it, if you're not willing to proudly display your artwork on a wall, it's unlikely that anyone else will love it enough to buy it either.

My philosophy has become a bit like that line from Field of Dreams: "If you build it, they will come." To me, that means creating from the heart to make something so authentic it can’t be replicated. I truly believe that it doesn't matter how weird or niche your interests are; there are other people out there who are exactly your kind of weird. So I create for myself, building things that bring me joy and trusting that my people will find me.

And I’ll let you in on a secret: there is no greater feeling than making a sale to a complete stranger. I’m talking about someone you've never marketed to, who just stumbles upon your work and buys it simply because they love it. And on that note, I’d like to take this opportunity to give a huge shout-out to my unknown fan in Spain who recently bought a pair of socks featuring my ukulele pattern from my Redbubble shop. I see you & I appreciate you.

Now, I don't want to give you the wrong impression. As incredible as it is to find someone who loves your art enough to buy it, the reality is that designing for an 'audience of one' isn't exactly a shortcut to commercial success. To be perfectly honest, I am not (yet) wildly successful by any traditional metrics. In fact, my number one customer is, without a doubt, me.

And you know what? I absolutely LOVE every single purchase I’ve made. My home is filled with my art, and it brings me joy every single day. I have a shower curtain featuring my East Van Cross & Crows, an apron with my whimsical astronauts, and art on my walls that makes me smile.

The biggest lesson this journey has taught me is that the true reward is separate from the income. The joy, for me, comes from the doing—the meditative process of getting into a flow state where all that matters is the art taking shape under my hands. On days that I dedicate time to art, my mood is better, my stress is lower, and my happiness is greater.

I am still actively working toward building a business where my creative endeavors provide the bulk of my income, but the fact that it hasn't happened yet doesn't deter me. The joy is in the making. I'm going to keep creating for an audience of one, and trust that one day, if I let my weird light shine bright enough, the other weirdos will know where to find me.

If you’re starting your creative business or just feeling stuck my advice is this: Find artists that you admire. Look at what they post and listen to what they have to say about their process. And then, decide what parts of that advice make sense for you and what parts you want to discard because they just don't fit with your version of success.

You don’t need to follow every trend, or anyone else’s path.

Now I'd love to hear from you.

Who is an artist you admire, and what's one piece of their advice you’ve chosen to either follow or ignore?