Why Working Solo Can Make You Overthink (and What Actually Helps)
By Shannon Kate Murray, Founder & Editor of High Flying DesignWhen you work for yourself, overthinking comes with the territory.
There’s no manager telling you you’re doing a good job. No colleague saying, “This looks fab.” No clear feedback loop. Most days, it’s just you, your ideas, and silence.
That silence can be unsettling. And if you’re not careful, your brain fills it with doubt.
You start questioning decisions you would never second-guess in a team. You wonder if your services are right, if your messaging needs tweaking again, if you should be doing more. You convince yourself the problem is clarity, when often it’s confidence.
I’ve been there.
Why solo founders doubt themselves more
When you work alone, your brain is doing everything at once.
You’re the strategist, the decision-maker, the marketer, and the person holding the long-term vision. Without external feedback, nothing ever feels fully “finished”.
So your mind keeps circling.
Silence starts to feel like something’s wrong. A quiet inbox becomes proof you’re off track. Instead of trusting what you’ve already built, you start changing things that don’t actually need changing.
More services. More tweaks. More thinking.
Not because the business needs it - but because uncertainty feels uncomfortable.
When “perfecting” becomes a problem
There’s a fine line between improving and overthinking.
At some point, refining your services or messaging stops being strategic and starts becoming avoidance. It feels productive, but it keeps you stuck.
Often, the issue isn’t that your offer is wrong. It’s that it hasn’t been visible long enough.
Most businesses don’t need constant adjustment. They need consistency, repetition, and time. Overthinking interrupts that.
What helped quiet my own overthinking
I didn’t change everything. I simplified.
I simplified my systems
I’ve learned that when my work is organised, my brain is quieter.
For me, that means:
Not everything needs to be digital. Not everything needs a complex system. When things have a place, your mind can rest.
I reduced distractions
I realised how much noise I was carrying without noticing.
As a test, I put my phone into black-and-white mode for a week. I checked it less. I compared less. My head felt calmer.
I didn’t need more willpower - I needed fewer triggers.
I made life bigger than work again
For a while, my entire life revolved around my businesses. That quietly increased the pressure I put on myself.
Now, I make space for things that have nothing to do with work. Reading fiction (currently reading Lucy Jane Wood’s Rewitched). Rewatching old shows (currently watching Pretty Little Liars - it’s on BBC iPlayer). Going for long walks. Doing less, on purpose.
When life expands, work stops carrying everything.
I controlled what I could
One small but powerful change was wearing noise-cancelling headphones while I work.
I hadn’t realised how overstimulating my environment was until I removed the noise. It was one variable I could control - and it made a noticeable difference.
What changed
I stopped constantly questioning my direction. I stopped assuming silence meant something was wrong. I stopped changing things that were already working.
Not because doubt disappeared, but because my brain had fewer reasons to spiral.
Overthinking wasn’t the problem. Too much noise was.
If this sounds familiar
If you’re working solo and:
doubting yourself more than you expected
constantly tweaking instead of trusting
feeling mentally busy even on “lighter” days
You’re not failing. You’re missing feedback.
Simplify what you can. Reduce the noise. Stick with what already works for longer than feels comfortable.
Clarity doesn’t always come from doing more.
Often, it comes from doing less and giving things time to settle.
