27. Learning to Be the Boss of Me

I left my last job (part time)  in 2025 thinking I was ready. I’d been running my own business for eight years… so really, how hard could it be?

As it turns out, the hardest part wasn’t building the business at all. It was unwinding decades of invisible rules around time, creativity, and safety. Rules I didn’t even realize were still running the show. I’ve learned freedom is exciting… but  also deeply uncomfortable.

This post is an honest look at what my transition into full-time entrepreneurship has actually been like: the creativity that’s finally resurfacing, the (sometimes unsettling) freedom of having no one else to point at, and what it really means to learn how to be the boss of me.

The Habits I Didn’t Know Were Compromises

I’d been employed in some form since I was 21. I’m turning 50 this year, which means I’ve spent nearly three decades organizing my life around someone else’s schedule. Over time, those constraints stopped feeling like constraints and started feeling like normal, responsible adulthood.

Take my Pilates routine, for example. For years, I went to a 6am class so I could get home, shower, and make it to the office on time. It wasn’t my favorite class or my favorite teacher, but it fit the schedule, which made it feel like the right choice. I told myself I liked early mornings but in hindsight, it was mostly logistics.

When that constraint disappeared, I expected to feel instantly free. Instead, I felt oddly overwhelmed. Suddenly I could go at any time, choose any class, and follow teachers I actually liked. It took me two to three months to figure out when and how I genuinely wanted to work out, which felt a little ridiculous.

But that was my first clue that many of my habits had been shaped by compromise rather than choice. Without someone else structuring my time, I was left with a question I hadn’t had to answer in years: who am I when I get to decide?

The Creativity That Was Waiting

What I did not expect was how much creativity I had been trading for a paycheck.

As an employee, I always worked inside someone else’s vision and strategy. I knew which ideas would be welcomed and which ones would be politely ignored. I understood what was politically palatable, what was worth pushing for, and what would die in a meeting.

So I edited myself. Not dramatically, and not consciously. I simply learned not to get too attached to ideas I couldn’t fully execute or that no one had asked for. 

Once I stepped away and had some distance, the ideas showed up. (A lot of them.) It turns out they had been there all along, just waiting for permission I didn’t realize I needed to give myself.

For anyone worried they will “run out of ideas” once they leave employment, I can confidently say that lack of creativity is not the problem. Suppression is.

The Cheetah in the Cage

In Untamed, Glennon Doyle describes visiting a zoo with her family and watching a cheetah, built to run but pacing inside a cage. The door might even be open, but the cheetah stays put because the cage feels familiar.

While journaling at the end of the year, I realized how much that metaphor applied to me. The door had been open for a long time, but I stayed inside because employment felt safer. Someone else was responsible for the paycheck. My job was to show up, do good work, and stay within the lines.

We tell ourselves this story that employment equals security, even though we all know that companies shut down, budgets change, and roles disappear. What I had really forgotten was how much responsibility comes with freedom.

When you are employed, there are built-in explanations. The schedule, the priorities, the boss. When those disappear, there is no one else to point at.

That is both liberating and deeply uncomfortable to process.

Learning to Be Free Takes Time

One of the clearest signs that I was still mid-transition showed up in my office. For months, it remained a strange mix of things from my old employer and things from my business. I worked there every day, but it still felt temporary, like I hadn’t fully moved in yet.

Only later did I feel ready to clear everything out and set the space up the way I actually wanted it.

That pattern showed up everywhere. What I am learning is this:

• It takes time to get comfortable being fully responsible for your results
  
  
• You cannot flip a switch from employee to entrepreneur mindset
  
  
• Freedom starts internally, not when circumstances change
  
  

For years, I made professional development plans based on what my employer wanted me to focus on. Now I’m planning around what I want to learn and what will best serve my clients. While that sounds like a small shift, it’s actually a very significant one.

What I Can See Now

Without the constraints of my employee mindset running in the background, I can finally see that I’m able to build a business that looks very different from what I thought was possible before.

There were limits I didn’t even know were there.

This is me heading into 2026, learning how to be the boss of me and letting go of old assumptions. I’m building something I could never have imagined six months ago.

If you are in this transition too, or even just thinking about it, know that feeling disoriented is normal. 

I'll keep you posted as I continue unwinding old patterns and building new ones. Because if there's one thing I've learned, it's that sharing the messy middle makes all of us feel less alone.

Listen to the full episode for more on what this transition has really been like and if any of this resonates, I’d love to hear from you at [email protected]. I'm right in the thick of it with you, figuring out what it means to truly work for myself after decades of working for someone else.