Why Creative Freedom Isn’t Free (And the Emotional Costs Aren't Taught in Any Course)
Box Cutter Co. Free Issue No. 89
You’re not behind. You’re just refusing to fake it.
Have you seen this type of social media post lately? 👇
“I’ve been posting every day for two months and I’m just not seeing results…”
I’ve come across several recently, especially on LinkedIn (and not just from beginners).
Some folks will say “this is a ‘mindset’ thing…”
And they’re not entirely wrong.
Yes—clarity, persistence, and perspective matter. But what they’re missing isn’t minor—it’s at the core of creative work and building a creative enterprise. The struggle isn’t just mental. It’s also emotional.
You’re not just reframing beliefs. You’re confronting discomfort.
You’re managing ambiguity. You’re doing real creative work—in public—even when no one claps, likes, or comments. It’s full of uncertainty. Not-knowing.
This isn’t a ‘personal branding’ or niche-down or content calendar problem.
It’s a wanting-to-be-seen problem.
And the cost of navigating this isn’t paid in effort alone. For example, the incessant “just be consistent” advice plastered across social media ad nauseam.
The price is also in emotional energy—the kind no content strategy accounts for.
“But what’s the difference between mental and emotional?” some will ask, “Aren’t they the same thing?”
No, here are a few differences:
Mental = thoughts, mindset, self-talk, decisions, strategy.
Emotional = feelings, fear, shame, grief, uncertainty, exposure.
Someone might know comparison is toxic. But still feel gutted by it when they see someone having more ‘success’ than them.
They might decide to keep showing up, but still carry dread when the silence returns, continues, and even prevails.
That’s the emotional labour of building something creative, authentic, maybe even soul-aligned, maybe more on the non-obvious side of things.
And I’m speculating there's no course coming to help you with it. (Drop in the comments if you have come across one)
At the Same Time…
I’m watching some other shifts in creator circles: more seasoned creators—people like
, , and — are rethinking where and how they show up in their creative enterprises(including all three showing up here on Substack in recent months).
Jay, for example, recently shared how becoming a new parent is reshaping his priorities and focus. For instance, less social media, more intention, and focus on other areas of what he’s built.
This isn’t retreat — It’s recalibration.
And often underneath these shifts?
A shared experience most gurus, advice posts, and digital courses gloss over:
Creative freedom comes at a price (paid in emotional labour).
What Most Courses and Creator Gurus Gloss Over
Most digital courses and guru playbooks cover the visible, strategy parts of building a digital presence and creative enterprise:
How to grow your email list
How to build a content system
How to monetize your skill stack
How to optimize your personal brand (a bullshit notion)
For beginners, this can be useful stuff.
, for example, has a practical free course on being a one-person business. But here’s what the vast majority of courses leave out:What happens emotionally when no one responds
What to do with comparison bias, ambiguity, and doubt
How to keep showing up when it feels like nothing is working
How to manage the friction between revenues and authentic alignment
These are all components of emotional labour — and ‘mindset coaches’ probably won’t be able to address.
Building a creative enterprise… Every day, you create from the inside out. You’re doing work no content calendar captures, no Notion template optimizes, no AI prompt productizes.
You’re not just making decisions. You’re often unmaking identities.
You’re metabolizing fear.
You’re writing without applause.
You’re coaxing yourself through the silences.
You’re asking if what you’re building is something you can live within.
It’s not “impostor syndrome” (a bullshit term, as well).
You’re not lying.
You’re not deceiving anyone.
You’re not performing a false identity.
(All key components of defining the term “impostor”)
You’re showing up—uncertain but honest.
That’s not imposture.
That’s volition.
It’s holding the mirror long enough to feel what it shows you, not just what you see in a quick reflection.
👉 What do I know about this? 👇
I Didn’t Just Quit a Job — I Dismantled an Identity
I left a decade+ career in 2022.
Cold turkey.
But I didn’t just leave a job—a 10+ year career in education and healthcare leadership—I left a version of myself that knew how to play the game:
How to chase recognition (instead of alignment).
How to be productive in toxic systems built for burnout.
How to be agreeable in meetings where silence is safer than truth.
That version of me was good at surviving, but not at living with soul-alignment. And when I walked away, that identity didn’t just disappear. He lingered. Sometimes Loudly — especially when things got quiet.
The doubts would creep in.
Were the doubters right?
Did I make the right decision?
How will I continue to generate revenue to pay the mortgage and bills?
(And so on, and so on…)
Moving from permission-based systems to permission-less ones…
These are the parts no course prepares you for. Leaving the old story is easy to post about. But living without it?
👉 That’s part of the emotional labour.
For example:
Choosing clarity over agreement — labour.
Showing up before you’re fully ready — labour.
Listening to what your soul may be asking — labour.
Offering something real to an Internet optimized for speed — labour.
Putting boundaries on your time, your attention, your body — labour.
And the most challenging part?
👉 You still have to do the work (anyway).
Even when no one claps.
Even when your voice shakes.
Even when the metrics are flat (or falling).
As a mid-aged fellow, early in his fifth decade, with three kids, a mortgage, debts, and so on… societal and cultural norms did not support my decision to walk away from stability, security, and good benefits.
(One family member didn’t talk to my wife Lisa and I for almost two years — they thought we were endangering our family). 🤷♂️
This is also labour.
The Labour You Probably Didn’t Expect (But Can’t Avoid)
This is some of the emotional labour I’ve navigated in establishing creative businesses:
Turning questions over one more time.
Not for content, but because your direction, your voice, and your value are still taking shape. And clarity doesn’t arrive on a schedule. (It may never come)
Refusing to package your identity into a “personal brand.”
Because you’re not a product — You’re a person. And sometimes the parts you’re not sure how to market are the most worth keeping. (Personal branding is a ridiculous, bullshit term)
Protecting your clarity instead of selling your personality.
Because chasing visibility without inner alignment is a trap, and attention without integrity is a tax.
Holding the tension between revenues and real alignment.
You could make more. Faster. But not without fracturing something inside you. And you’re probably not here to repeat the systems you left behind (I know I’m definitely not)
Showing up again, (and again, and again) even when it doesn’t feel good or certain.
Because volitional work rarely does. But that doesn’t mean you’re doing it wrong.
It means you’re doing it for real.
There are easier ways to make money.
Faster ways to get attention.
But if you’re building a creative enterprise from the inside out (not outside-in)… What you’re also building is the capacity to feel without fleeing.
You can outsource admin.
You can automate scheduling.
You can template a content strategy.
But in this work, in creative work, emotional labour is non-transferable. It’s yours. And it will shape you. Not by simply pushing through (often my go to strategy), but by witnessing.
By identifying. By navigating. By staying awake to it.
The discomfort of progressing with meaning (to you) is better than the comfort of meaningless motion (like chasing applause and likes).
You don’t move forward by feeling ready. You feel ready by moving forward.
Fast is easy. Real is hard. Worth is rare.
The work that pleases algorithms isn’t the work that builds a creative life with personal meaning and intention. And the creative work that builds a life rarely pleases the ever-changing algorithms.
You can scroll. You can post. You can perform. But can you stand what you’re building 6 months from now, 12 months, 18 months, and so on?
Not everything that performs is real and genuine. And not everything that’s real and genuine performs.
By doing the more soul-aligned work, which can mean almost daily friction of building with integrity, which will rub up against hustle-bro strategies and comparison bias.
Call it a contract.
The one you didn’t know you signed. The one that costs more than you expected. Yet gives you back more than you thought possible.
Not freedom. Not fame. But something rarer:
👉 Congruence.
And the creative business that can be built on that?
Isn’t just a product. Isn’t a brand. It’s a creative life.
A living in the making—(instead of the commonly phrased opposite).
This is Part 1 of a longer series on emotional labour in creative work.
Watch for the next issue.
P.S. Box Cutter Co. is growing.
We now have a dedicated LinkedIn page
After two and a half years, we’re approaching 200 issues on this site (this is #193). Paying subscribers can access the full archive.
What started as a weekly dispatch about building creative enterprises from scratch is becoming more:
a business,
a philosophy, and
a practical approach to building from the inside → out.
More courses, tools, and deeper resources are on their way: for creative folks, professionals, and organizations building something real (without faking it and falling into hustle-hype).
And, for those navigating the more non-obvious realms. The long-term sustainable builds.
Thank you to those who have recently become paid subscribers.
If you’re not already, consider becoming a paid subscriber. It’s only $ 5 per month (or $50 per year). This helps fuel more of this kind of clarity-driven, soul-aligned writing, supports, and tools.
Watch for more paid-subscriber issues on their way, with more practical tips and tools.
Based on what I’ve learned in building creative enterprises, which now generate revenues well beyond what I walked away from in salary in the corporate public sector, just over 3 years ago.
"You don’t move forward by feeling ready. You feel ready by moving forward."
This is your permission slip to yourself. Stamp it as often as you like. No need to wait for outside approval.
You are your own creative destiny. Run with it.