The stability vs freedom paradigm

Jenni Gritters
5 min readDec 1, 2023

Lola had two asks for our business coaching work together: Over the course of 12 sessions, she wanted to find more stability in her business. But she also wanted to maintain the freedom she already had.

She noticed that whenever she tried to add stability to her workload, she started to freak out. What if putting clients into a less chaotic workflow meant that she had less freedom? She loved being able to surf whenever she wanted. She loved being able to take a week off without anyone noticing. She ran her own business because of the freedom and she didn’t want to be accountable to anyone else. But the chaos was also starting to wear on her.

The word stable can be defined in a few different ways. At a basic level, something that’s stable is not likely to overturn. If something is stable, it’s fixed — often to the ground or the wall next to it. But stability is also defined as sanity and sensibility. And it something is stable, it means that it’s not deteriorating.

Often, people come to my coaching room worried that stability and freedom are polar opposites. Like Lola, most of us get into self-employment because we want to control our time. We want to have the freedom to do what we want when we want it.

But placing freedom and stability at opposite ends of the spectrum is what we call in the coaching world a…

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Jenni Gritters

I’m a writer and business coach for freelance creatives based in Central Oregon. I write about the psychology of small business ownership.