What Happens When High Performers Go It Alone
Navigating the uncertain waters of entrepreneurship after leaving the corporate world.
I recently had a conversation with someone I used to work with. She is highly skilled and incredibly smart. Six months ago, she left corporate and started her own consultancy. She has been putting in the work. She has made calls, sent emails, and worked her network. But she’s frustrated with where she is.
As I listened to her, I saw myself six months ago. I remember looking in the mirror and thinking, Where the hell am I? What the hell did I do? How did I get here?
I spent roughly 25 years working inside organizations. For most of that time, I was a high performer. I knew how to walk into a mess and figure out what was wrong. Give me a problem, and I will keep working at it until I understand what needs to happen next. I knew how to work. I knew I was good at it.
When I went independent, I assumed those skills would translate. I didn’t realize how much of my success had happened inside a structure that was always there.
I had worked from home since 2016, so I thought I knew how to manage my own time. I quickly learned that working remotely and working for yourself are not the same thing. When you work remotely, you’re still inside someone else’s structure. You know when to log on. Your calendar tells you where to be. You know what needs to get done.
I didn’t realize how much I depended on that structure until it was gone.
When I went independent, I recreated what I knew. I tried to fit entrepreneurship into a nine-to-five because I had spent most of my adult life working that way. Even this summer, I took a 35-hour-a-week contract. I thought it would give me stability without taking away my freedom.
It didn’t.
Before long, my calendar wasn’t mine. Everything I wanted to build had to fit around someone else’s schedule. I had gone independent and somehow recreated employment.
The part that gets interesting is what happened next. I didn’t question whether the way I was working made sense. I questioned myself.
When you’ve spent years being good at what you do, suddenly not knowing what to do can mess with you. I hadn’t lost my experience. I hadn’t suddenly forgotten how to solve problems. But the environment where I had been successful was gone.
Corporate gives you more direction than you realize while you’re in it. Someone decides what needs your attention. You know what is expected of you. There is usually some way to tell how you’re doing.
When you leave, a lot of that disappears. Nobody tells you what a productive Tuesday looks like anymore. When you’re used to performing at a high level, that lack of direction can start to feel like failure.
My response was to do more.
I tried LinkedIn. I contacted agencies and did outreach. I bought lead-generation software and set up a CRM. I built a website and created different offerings. I kept looking for the thing that would finally start working.
For months, I felt like I was running on a hamster wheel. I was busy, but I couldn’t tell if any of it was getting me anywhere.
Because I’m used to solving problems, I treated this like another one. If something didn’t work, I tried something else. Eventually, I stopped questioning the approach and started questioning myself.
Maybe I shouldn’t have left. Maybe I wasn’t cut out for this. Maybe I had completely screwed up my career.
It can make you batshit.
Things started to change when I stopped forcing the business into what I thought it was supposed to be. I stripped down my website and redirected it toward my writing. I stopped worrying about what a consultancy was supposed to look like. I started paying attention to what was actually happening.
One of the first things that caught my attention was a TikTok post that was basically a fart of a thought. I was making fun of corporate life and Netflix. There was no big strategy behind it.
It got around 160,000 views.
I didn’t think I had suddenly figured everything out. Something I said had connected with people. That was enough for me to pay attention.
It was a small, faint signal.
So I kept writing.
I had already been writing on LinkedIn. I started publishing on Substack and Medium, too. I wrote about corporate life and the things I actually cared about. I kept coming back to operating models and transformation. AI became part of what I was exploring. Eventually, I found myself working inside AI environments.
None of that was part of my original plan.
The business I thought I was building ten months ago is not exactly what I’m building today. I don’t know what it will look like five years from now.
I’m becoming okay with that.
My partner once gave me a ship metaphor that helped me make sense of what was happening. Imagine you’re the captain of a ship and you can’t see land for miles. Your first reaction might be that you’re lost.
But not seeing land doesn’t mean you’re lost.
You still have information. You use what you have to figure out where you are. Then you decide where to move next.
For most of my career, an organization helped provide that direction. Once I was outside of that system, I had to get comfortable making those decisions myself.
I also had to change the way I thought about decisions.
For a while, I would look backward and try to figure out which decision I got wrong. I don’t do that anymore. A decision doesn’t always have to be good or bad. Sometimes it’s just an if-then statement.
If I do this, something happens.
Now I know something I didn’t know before. I make the next decision from there.
The 35-hour contract taught me that I don’t want to recreate another nine-to-five. The outreach that went nowhere told me something, too. Writing gave me different information. The work I’m doing now is giving me even more.
I couldn’t have known any of that before I tried it.
That’s what I recognized while talking to my former colleague. I knew what it was like to look at everything you’ve done and wonder why you aren’t further along. I knew how easy it was to go back through every decision and look for the one you got wrong.
But I could also see something she wasn’t giving herself enough credit for. Six months earlier, she had started a business. She had moved halfway across the world. Her life had changed dramatically in a short amount of time.
She was still figuring out what came next.
So am I.
There was a time when that answer would have bothered me. I wanted to know where I was going. I wanted to know that whatever I was doing would work.
I don’t need that certainty in the same way anymore. If I look back on the next five years, I want to be able to say that I moved through them with grace, patience, and intention. I’m not rushing through this one. I don’t need to know exactly where I’m going yet. I’m trying to sit in the journey, even when it’s uncomfortable, instead of constantly trying to figure out how to get through it faster.
That is very different from what I would have done 10 or 20 years ago. When you’ve spent most of your career being the person who figures things out, not knowing what comes next is uncomfortable. In corporate, there is almost always something next. Another project comes along. Your role changes. Something needs to be fixed. There is always something telling you where to put your attention.
When you leave, that goes away. Sometimes I have to choose what comes next without knowing where it will take me. Other times, I have to leave things alone long enough to see what happens. I’m still learning how to do both.
I haven’t figured all of this out, and I don’t think I need to. I’m learning what it means to be a high performer when there is no company telling me what performance is supposed to look like.
For now, I’m getting more comfortable with the open water. I may not be able to see land yet, but that doesn’t mean I’m lost.
