4 gentle experiments for creative entrepreneurs

How your business overwhelm might have roots in a classroom

That feeling when something wants to come out but you can't find the words, when you're so close but so stuck - it started way before you opened your business and I want us to gently unpack it together.

You care deeply about building a business that reflects your values - one that rejects the extractive, oppressive practices often promoted in entrepreneurship. You've been working to create something different, something that actually fits who you are and how you work best.

And you've achieved so much already. You've built systems, served clients, created your own unique methodologies. You show up day after day, pushing against the current of "how business should be done."

Yet there might be something underneath the overwhelm you feel - something that started long before you opened you began to assemble your tech stack.

Both my maternal grandmother and great-grandmother went to Thomas Indian School, a boarding school run by the state Board of Charities, designed to "Kill the Indian, save the man." My paternal grandmother was schooled during the Welsh Not movement, a punitive approach to prevent the use of the Welsh language in schools. These aren't easy words to write, but when I talk about decolonizing traditional education, this is exactly what I'm referring to.

The same educational system that was weaponized against my ancestors continues to shape how we think we "should" learn, how we "should" organize information, how we "should" show up in our work. Even if you don't share these specific histories, you've likely felt the weight of educational approaches that insisted there was one right way to learn, one right way to think, one right way to be productive.

Since I've been teaching about decolonizing knowledge and education, people have shared all kinds of stories about their time in school - stories that run the gamut in terms of identities and backgrounds. You don't have to have a marginalized identity to have experienced educational trauma. And it's entirely possible that what happened in those classrooms is still affecting how you show up in your business today.

If you find yourself constantly overwhelmed by systems and tech, frustrated by how little time you have to actually learn new things properly, or blaming yourself for "lacking something" that's holding you back - it might be time for a gentle inquiry into what's really going on beneath the surface.

Time to run a gentle diagnostic

Here's what I've noticed after years of working with creative entrepreneurs coaches, and consultants: that overwhelming feeling when you try to learn new tech? That frustration when you can't find time to set up systems properly? That self-blame for "lacking something"?

It's not about time. It's not about your capability. It might actually be about an outdated learning blueprint that got hardwired into you decades ago - one that insists learning happens in rigid, prescribed ways that simply don't match your natural instincts.

When my son was in high school, he was in an acapella group that practiced 3 days a week - an hour away, in a whole other county from where we lived. So 3 times a week, I had a couple of undistracted hours when I'd sit in the car doing things I normally had a hard time making time for - reading, listening to podcasts, calling my sister. With no way of multi-taking with laundry, cooking, dishes etc, these activities allowed for depth, for full immersion. Being completely absorbed in a book or howling with laughter on the phone was deeply fulfilling. This memory drives a question I’m often asking in my work as a Notion teacher looking at learning through the lens of decolonization: Why is it so hard to experience that same deep engagement in our work?

The answer might lie in how school taught us to fragment everything - separate subjects, separate teachers, separate ways of being. These silos were never about helping us learn better. They were about control and obedience and hopefully you know by now that I’m not here to be running my business without questioning the so called norms.

Let's troubleshoot this together with some questions that might feel uncomfortably familiar:

The lingering "not quite traumatic but still there" stuff: What low-grade negative experiences from school led to behaviours that still annoy you in your work today?

For example: Charlie's high-school algebra class had 45+ students crammed into a room meant for 25. The teacher raced through equations while Charlie sat in the back, hand half-raised but never called on. They'd stay after class for help only to be told "office hours are Tuesdays" - when Charlie had hockey practice. They scraped by with C's, convinced they were "bad at math." Today, Charlie runs a successful consulting business but still freezes when faced with spreadsheets or pricing calculations. They'll spend hours avoiding their QuickBooks and when they finally have to learn a new platform or system, that same half-raised hand feeling returns. They know they can’t figure it out on their own but feel guilty, as if they might put somebody out by asking for help.

The moments that still sting: What specific incident from school do you still remember that directly connects to something you consistently struggle with?

For example: Frieda was 11, standing at the board solving a geography question about state capitals. She said "Springfield" instead of "Salem" and her teacher laughed - actually laughed - before saying "Well, that's creative, but completely wrong. Anyone else want to try?" The whole class giggled. Frieda can still feel the chalk dust on her fingers, the heat in her cheeks. Now, 30 years later, she's a brilliant brand strategist who knows her stuff inside and out. But she'll rewrite client emails seven times, google basic facts she's known for years "just to be sure," and add "I think" or "maybe" to statements she's 100% certain about. She questions everything, even when she's alone at her desk at 2am with no one watching.

The relationship that undermined everything: Was there a teacher or adult who consistently made learning harder for you?

For example: Elsie's high school choir director ran rehearsals like military drills. No questions allowed. No suggestions taken. Students stood in assigned spots, sang only their designated parts, never permitted to offer input. He'd cut people off mid-sentence with "That's not your decision to make." Creative ideas were met with "Just follow the sheet music." Elsie loved music but felt suffocated in that room. Now, as a website designer, she has this uncanny radar - she immediately notices when clients interrupt their team members mid-sentence, when they dismiss ideas without consideration. The moment she spots these patterns, something shifts. She stops suggesting creative alternatives, keeps her mockups safe and conventional, bills her hours and moves on. She's still professional, still delivers good work, but that spark of going above and beyond? It quietly switches off, leaving her uninspired by the work she delivered.

The pattern that never stopped: What kept happening throughout your education that made you struggle despite being genuinely smart?

For example: Shawna was labeled "disruptive" in first grade for finishing her work early and helping classmates. By third grade, it was detention for doodling. Middle school brought suspensions for "talking back" when she asked why they had to do things a certain way. Teachers said she was "bright but difficult," "has potential but needs discipline," "would excel if she could just follow directions." She understood complex concepts that stumped others, devoured books above her grade level, but couldn't sit still for 45 minutes straight. Now, as a freelance art teacher in her 40s, she's brilliant at what she does - her students adore her unconventional methods. But when it comes to running her business, every system feels like a straightjacket. Notion templates feel rigid, scheduled tasks feel like detention, even Trello boards make her feel trapped. Her ideas are too wild, too interconnected, too alive to fit in anyone else's boxes.

Four micro-moves to escape the classroom in your head

These aren't overhauls or massive commitments. They're small, playful experiments designed to interrupt those old educational patterns and help you reconnect with how you actually learn and work best. Choose one that feels both slightly scary and oddly exciting.

Experiment #1: The Learning Conditions Map (low-stakes discovery) Figure out what conditions you need to learn something new.

This might be the best gift you can give yourself - permission to learn your way. Start paying attention: Do you absorb information better through videos or conversation? Do you need silence or background noise? Does your ideal learning environment change based on your mood, the weather, your stress level?

This week, before you try to learn anything (even how to use a new app feature), ask yourself: "What do I need right now to make this easier?" Then give yourself that thing, even if it feels "inefficient" or "silly." Track what works. You're building a map of your actual learning style, not the one school said you should have.

Experiment #2: The Indisputable Knowing List (medium-stakes validation) Make a list of things you indisputably know about your work based on years of experience.

Dig deep into the complex, nuanced things that consistently work for the people you serve. Turn these into principles or guidelines you can reference when self-doubt creeps in. This isn't about ego - it's about acknowledging the expertise that lives in your bones, the knowledge that no amount of educational trauma can shake.

Keep this list where you can see it. Add to it weekly. When you catch yourself adding "I think" or "maybe" to something you know for certain, check your list. You know more than school ever gave you credit for.

Experiment #3: The After Action Review (medium-stakes pattern tracking) After each client engagement, document not just what worked but how you showed up.

Were you proud of how you led those strategy calls? Did you shrink when you should have stood firm? This isn't about shame - shame has no place here. This is about noticing the moments when old school patterns resurface. When do you make yourself small? When do you ask permission for your own expertise?

Write it down. Notice patterns. Sometimes just seeing it on paper is enough to start changing it.

Experiment #4: The Friction Flip (high-impact pattern interruption) Focus on your biggest friction point and change it completely.

If mornings feel like detention, work at night. If sitting at a desk feels like being trapped, stand at your kitchen counter or sprawl on the floor. If typing feels constraining, voice record everything. Need giant post-its on every wall? Do it. Need to walk while you think? Build it into your pricing.

This week, pick your most frustrating business task and do it completely differently. Not better, not more efficiently - just different. You're not looking for the "right" way; you're proving to yourself that there are infinite ways and you get to choose.

Track what surprises you.

Notice resistance, excitement, unexpected ease. Even loose internal tracking counts as data. You're not trying to optimize anything - you're just remembering what it feels like to learn and work in ways that actually fit your brain.

The other side of educational trauma

If you keep cycling through different platforms and systems, always looking for the "perfect" solution that doesn't require you to actually learn anything new, here's where you're headed: Your business information stays scattered across dozens of tools, creating the exact overwhelm you were trying to solve. Meanwhile, that same classroom voice in your head keeps telling you that you're "bad at tech" or "not organized enough" or "lacking discipline."

But here's what I want you to know: You're not broken and you're not too old or too anything to learn new things. The traditional ways we're taught to approach tech - through tutorials that assume we all learn the same way - simply don't work for many of us.

Once you understand how your brain actually learns and start working with it instead of against it, everything changes. You stop feeling like you're "bad at tech" and start feeling curious about what's possible. You build systems that actually support how you work rather than forcing you to contort yourself into someone else's productivity fantasy.

Learning Notion (or any platform) becomes less about learning all the features and more about understanding yourself. And that understanding? It transforms not just your tech skills, but how you approach challenges in every area of your business and life.

So here's my invitation: Choose one of the micro-moves above and try it this week. Just one. Pick the one that made you feel both nervous and intrigued - that's usually the one your brain needs most.

And to make this a little more fun, I’ve made a free Notion worksheet so you can pick your experiment and go through the exercises on your timeline, at your own pace.

Track what surprises you. Notice what feels different. And if you want to go deeper into building systems that actually match how your brain works, I'm running Digital Gardening: the Curiosity Comeback again in February. It's where we take everything you're discovering about how you learn and turn it into sustainable, liberating systems for your business. Learn more and join the waitlist today.

Your brain is already perfectly designed for learning. You just need to work with it instead of against it.