When what you crave is also your burden

She posted about her mid-morning hike on a Wednesday, and I thought, “I want that”. Here was this accomplished entrepreneur running a business that helps thousands of people, and she had the freedom and flexibility to go for a hike in the middle of the week.

Meanwhile, I was scrolling Instagram over lunch in an interior office with no windows. She was up in the sky and I couldn’t even see the sky.

I was envious.

She was good at her job, making an impact, and she had control over her schedule. The hiking part? I could take it or leave it.

I didn’t know it at the time, but this was just one of the many signs I would follow to eventually leave my full-time job working at a university a couple of years later.

But today, having been my own boss for over half a decade, I see things in a different light. And, if I could transport back in time and talk to the “lunch-break-scrolling-with-envy” version of me, I would share a few words of caution.

What you crave is not what you need

I have always craved freedom and flexibility, and I’ve always resisted circumstances where I feel trapped, constrained, or confined. The idea of being locked into a repetitive structure? No, thank you.

In the years leading up to leaving my full-time job, the pull of being self-employed was getting stronger and stronger. I was lucky to work in an incredible environment filled with people I genuinely liked and doing work that had meaning, but I knew I wasn’t spending enough time in my zone of genius. Any time I had the chance to run a live workshop, I felt alive and inspired.

I wanted more of that.

So my logical conclusion? Be my own boss to spend more time doing what I love AND have ultimate freedom over how I spend my time. Right?!

[cue record scratch]

Turns out I was wrong on multiple levels (and I clearly hadn’t yet read The E-Myth Revisited by Michael E. Gerber).

Aside from my naive visions how I would spend my days, my bigger blindspot was not recognizing what I craved was the opposite of what I needed.

Freedom vs focus

Recently I asked my spouse if he would ever describe me as flaky (as I was writing a piece about my dreaded F-word). Once he realized the question was not, in fact, a trap, he answered honestly: “No, I would not describe you as flaky. In the early years of your business, I would say you were unfocused.”

With no boss to report to, I had total freedom. I could decide what to work on, when to work on it, and how I want to work on it. No one to answer to. I made the rules.

I can still remember the glee I felt the first time I worked from a coffee shop (on a Wednesday, no less). Here I was living this entrepreneur life I’d been envying from afar. I felt untethered in the best way.

This was what I wanted, and yet…

Those first couple of years, I felt adrift, rudderless, and unfocused. Turns out, when you pair a multi-passionate person with undiagnosed ADHD with a complete lack of structure and zero deadlines, it’s a recipe for disaster.

Making the shift

Although it took longer than I’d like to admit, I eventually accepted the truth. I needed real structure and deadlines. Once I started to follow a regular work-week schedule as if I were employed by someone else, things started shifting.

The more I embraced constraints, the more focused I became.

I also started to see the Instagram inspirational entrepreneur content for what it was… marketing. Accounts who benefit from viewers seeing this idealized version of the self-employed lifestyle. People promoting the freedom and flexibility of ‘being your own boss’ because they earn a living from people who desire what they’re selling.

In reality, the experience of being self-employed depends a lot on how an individual is wired. If someone is highly self-directed and tends to follow through consistently on what they say they will do, their experience is likely quite different from mine. I’m someone who responds better to external expectations and deadlines, and I need to use strategies and interventions to create the structure that supports my ability to focus.

Oh, and in case I appear as if I’ve got it all figured out, I can assure you that’s not the case. But I’ve come a really long way from where I started, and that only happened when I admitted that what I craved was not what I needed.

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