I kept fixing it. It kept breaking.

Twenty-five years ago this month, I was unceremoniously dumped out of the corporate world. 

While I had job offers, I knew some of what didn’t work in that last job would still be there in these new ones, so I decided to try something else. I chose to bet on myself. 

The early days of entrepreneurship (by which I mean the first four or five years) were a continual lesson in both humility and grit. There is so much to learn, much of which I experienced as failure. At some point, I had picked up some skills and recovered from so many failures that I couldn’t bring myself to quit (notice the sunk cost fallacy there), even as I longed for a way out!

So I was as surprised as the next person when it started to work.

I learned to sell more consistently. I found help, both administrative and in serving clients. I had the confidence to raise my prices so I could afford better people who could do things I couldn’t do, and we could provide more valuable service to clients. 

Before long, the business was actually something that, from the outside at least, looked successful. I was making good money, I had a reasonable pipeline, and a team I was proud of. 

But inwardly, the stress was still building.

I thought about the business about 90% of my waking hours. I never felt “done,” or like I had done “enough.” The idea of growing beyond the success I had achieved both animated me and terrified me. I was reaching my physical and mental limits. I always felt like, no matter what I achieved, I was teetering on the edge of disaster. 

I wanted to quit, to find a way out, but deep down I knew this was my path — lifting leaders beyond their limits was something I was put here to do. 

I started asking different questions.

What is enough? What is mine to do? How can I shift my relationship with work so it doesn’t own me?

These questions led me to a different way of relating to my business and my life. And I see the same shift happen with the C-suite leaders I coach — people who, by every external measure, are succeeding, but who are white-knuckling it through every week.

If this is my life’s work, it can’t consume my life. It needs to enhance it. How can I hold my work differently so I get more life out of it? How can I be done at the end of the day and then let go of the work until the next day (or week)? 

Why can’t the work and I be in a better relationship? How can that relationship become easy and light?

If I have a fixed number of hours in the day, how do I use them well instead of always wishing for more? Instead of trying to speed things up, what if I slowed down?

This is a long way of saying that over the first 10 to 15 years, I made changes to help me survive in a system that wasn’t working for me. They bought me time. 

But when I got near the end of my rope, I resorted to the big guns and started changing my relationship to the situation. That’s when I saw real progress. 

Are there problems you’ve been improving around the edges but that stubbornly keep coming back? Things that might derail you from your most important work? Hit reply, and we can look for a different way to relate to the problem that might make all the difference.