Ep: 19 The Hidden Burnout of “Freedom-Based” Businesses
“I built the business to have freedom and then felt guilty every time I took it.”
Emylee
You know that thing we all say we want?
More freedom, more space, more ease.
But here’s the truth I had to face — even when I built the team, hit the revenue goals, and designed the dream schedule, I was still burnt out. I was still anxious about time.
And I didn’t know how to actually exist inside the freedom I had worked so hard to create.
This episode is me pulling back the curtain on what happens after you get what you say you want. I talk about my own patterns with work, money, and self-worth, and how productization has given me the systems to create space… but not the tools to emotionally exist inside it.
If you’ve ever hit a goal and still felt that weird, restless “is this it?” energy — this one’s for you.
What You’ll Hear in This Episode
My honest reflection on what happens when you finally reach your version of “freedom”
How I accidentally started a second business (because I can’t not make everything a project)
Why the real work isn’t building the system — it’s learning how to exist in it
What burnout looks like even when you “have it all”
The unsexy truth about capacity, control, and self-worth in entrepreneurship
My commitment to making 2026 the year of shadow work and actually enjoying my downtime
When You Get What You Wanted… Then What?
Let’s be real — most of us are chasing a version of business that gives us more capacity.
We want time back. We want ease. We want space.
And yet, when I built a team of six full-time employees, delegated everything, and technically had everything I said I wanted… I still felt resentful, overworked, and unfulfilled.
That’s when I realized: freedom without emotional regulation just feels like guilt.
Every hour “off” still came with mental math — how will I make this up? Am I falling behind?
Even when I started making art again, my default mode was to monetize it. (Yes, I accidentally started a clay jewelry business. Classic me.)
I couldn’t stop turning every creative spark into a business plan.
It wasn’t until years later — after leaving a job, rebuilding my business, and rebuilding myself — that I started to ask the real question:
What do I do with the space I worked so hard to earn?
The Productized Freedom Paradox
I teach productization because it works.
It’s the system that lets your business deliver without you being glued to your laptop.
But the system can’t make you feel at ease.
That part’s inner work.
And honestly? I’m still figuring it out.
Because even now, with the systems humming and the client roster full, I catch myself filling space with new problems to solve — new offers, new content, new “goals.”
It’s like my brain doesn’t know how to rest unless it’s producing something.
And that’s the paradox of productized freedom:
You can build the structure that gives you time back, but you still have to teach yourself how to be in it.
Blurring the Lines Between Work and Worth
Reading Never Not Working by Melissa Clark cracked something open for me.
It helped me see how deeply my self-worth is tied to my output.
If I’m not “doing,” my brain tells me I’m falling behind.
That’s the piece I’m working on now — learning to merge the productive version of me with the version that rests, the version that has limits, the version that’s still me even when she’s slow.
Because those aren’t two people.
They’re both me.
And if I can’t love the slower one, I’ll never fully enjoy the business I built for her.
Chapters
00:02 – Why I wanted to talk about freedom, burnout, and time
02:30 – How burnout looked even when I “had it all”
04:45 – The hobby that accidentally became a business
07:10 – The season where work stopped being fun
09:00 – Rebuilding from scratch and redefining “fun”
12:00 – Freedom guilt and the illusion of balance
17:30 – Why productization is still part of my healing
21:30 – Learning to merge the versions of myself
26:00 – What happens when we create new problems after solving old ones
29:45 – The question I still don’t have an answer to
Resources & Mentions
Never Not Working by Melissa Clark
Interested in Being on the Show or Working with Emylee?
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