A few days ago, I had a conversation with someone I used to work with. She’s smart, experienced and very good at what she does. About six months ago, she left corporate, moved to Europe and started her own consultancy. She’s been making calls, sending emails and working her network, but she’s frustrated because things aren’t moving as quickly as she expected.
As I listened to her, I kept thinking about where I was six months ago. I remember looking at myself and thinking, where the hell am I? What the hell did I do? How did I get here? I knew exactly what she was feeling because I had spent months asking myself the same questions.
I spent roughly 25 years working inside organizations, and I was good at what I did. 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 trusted myself in those situations because I had spent years doing that kind of work.
Then I went out on my own, and that confidence didn’t translate the way I expected it to.
I had worked from home since 2016, so I thought I knew how to manage myself. I had a routine and knew how to get things done without someone physically standing over me. What I didn’t understand was that working from home had never meant working without structure. I was still operating inside somebody else’s system.
When you work remotely, you still know when to log on. Meetings show up on your calendar. There are deadlines and priorities. Someone else has already decided that certain things need your attention. Even when the company is a complete shitshow, there is still a structure around you.
When you work for yourself, a lot of that disappears. Nobody cares what you do on Tuesday morning. At first, that sounds like freedom. Then Tuesday morning comes, and you have to decide what actually deserves your time.
I did what made sense to me. 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. This summer, I even took a 35-hour-a-week contract because I thought it would give me some stability while I built everything else. Before long, I was building my life around somebody else’s calendar again. I had left corporate because I wanted more control over my time, and somehow I had recreated the exact thing I didn’t want.
The problem was that I didn’t immediately question the way I was working. I questioned myself.
That’s where this got difficult for me. I had spent years being the person who could figure things out, so I felt like I should be able to figure this out too. I hadn’t lost my experience or suddenly forgotten how to solve problems. I was still the same person. But I was working without many of the things I had always used to tell me whether I was doing well.
So I did more.
I tried LinkedIn. I contacted agencies and did outreach. I bought lead generation software and set up a CRM. I built a website, changed the website and created different offerings. I kept trying things because I assumed eventually I would find the thing that worked.
For months, I felt like I was running on a hamster wheel. I was busy, but I couldn’t tell whether any of that work was getting me anywhere. Eventually, the questions stopped being about what I was doing and became questions about me. 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. There is something incredibly frustrating about knowing you are capable while having no idea whether anything you’re doing is actually working.
Things started to change when I stopped trying to force 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 so much about what a consultancy was supposed to look like and started paying attention to what was actually happening.
One of the first things that got 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, and it got around 160,000 views. I didn’t suddenly think I had figured out my business because a TikTok did well. I just paid attention to the fact that something I said connected with people.
It was a small, faint signal, and I followed it.
I started writing more seriously. I had already been writing on LinkedIn, but 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. I started writing more about AI, and eventually I found myself working inside AI environments.
That wasn’t the plan I had when I started.
The business I thought I was going to build ten months ago isn’t exactly what I’m building now. Some of the things I was convinced would work went nowhere. Other things I barely thought about opened doors. I couldn’t have predicted any of that because I didn’t have the information yet. I had to move to find out.
Danny gave me a ship metaphor during all of this that has stayed with me. If you’re the captain of a ship and you can’t see land for miles, it’s easy to assume you’re lost. But not being able to see land doesn’t actually tell you that. You still have information available to you. You use what you have, figure out where you are and decide where to move next.
For most of my career, an organization helped give me those coordinates. I didn’t realize how much I relied on them until they were gone. Once I was on my own, I had to learn how to make decisions without having someone else’s structure constantly telling me whether I was headed in the right direction.
I also had to change the way I looked at my decisions. I used to look backward and try to figure out which one I had gotten wrong. Now I look at them more like if-then statements. If I do something, something else happens. Whatever happens gives me information, and I use that information to make the next decision.
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 continues to give me information. None of those things needs to become a judgment about whether I’m successful or whether leaving corporate was the right decision.
That’s what I kept thinking about while talking to my former colleague. She was telling me everything that wasn’t working, but I was looking at someone who had left a job she couldn’t take anymore, moved halfway across the world and started a business six months ago. Of course she doesn’t know exactly where it’s going yet. How the hell could she?
What struck me afterward was how long it had taken me to extend that same grace to myself. I spent so much of the beginning trying to get somewhere. I wanted the business to work, and I wanted to know what I was building. More than anything, I wanted some kind of proof that I hadn’t made a giant mistake.
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 or 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.