Looking Back

I've been thinking about success lately. Namely, where I thought I'd be versus where I actually am.

I spent years chasing things. I’ve built businesses, advised businesses, and written a lot about technology, AI, data and leadership. I spent time overseas in mountains and deserts doing things that I never thought I’d do.

This is work I'm proud of. But when I look at where others ended up in those same years it's hard not to feel like I missed something. I see a lot of success stories and a lot of exits, business scale, and recognition.

I put in the effort. That was never the problem. The problem often was aiming in the wrong direction. Projects that made sense at the time but ended up leading nowhere. I had ideas that I believed in that the market didn't want. I also had ideas that the market did want. But, when i look back I tend to notice only the hours that I poured into things that simply didn't work out for me and the successes for others.

You see someone else's success and start doing the math. They started when you did, had similar resources, and faced similar challenges. But their path looks cleaner, more logical, and more successful.

But what you see is generally a lie, or at least not all of the truth. What you don’t see is all the things that didn't work for them either. The pivots they now call "strategic decisions." The luck that showed up when they needed it and the timing they can't replicate.

You're comparing your entire messy reality to their edited highlight reel. And so am I.

When I look at my past, I can see waste or I can see education. I can see failure or I can see learning. The facts don't change, but the story I tell myself about those facts is what i’ve realized can change.

A lot of people I know are exhausted from managing the gap between how they look and how they feel. They've gotten good at projecting confidence while privately wondering if they're doing enough, being enough, achieving enough.

That gap costs energy, clarity and the ability to make good decisions because you're too busy managing your narrative.

I realized this all recently and now i’m trying to make peace with how things actually went instead of wishing they’d have gone differently.

I’m not resigning myself to the present and I’m not lowering my standards or pretending I don't care about outcomes. I am recognizing that effort doesn't always produce the results you planned for and that working hard in the wrong direction still taught me something, even if it wasn't what I intended.

The people I respect most in this world don't have the cleanest resumes or the most impressive exits or the most money. They are the people that have done work that mattered to them, even when it was hard, even when it didn't pay off how they hoped, and even when it required starting over.

They stopped ‘performing confidence’ and started building it through honest work that sometimes succeeded and sometimes didn't.

I realized that my path (and yours) doesn't have to look like anyone else's to be worth walking.

That's what I'm working on. Peace with the path I actually took instead of the one I thought I should have taken.

Want more like this? I write about leadership, AI strategy, and finding clarity in a noisy world. Subscribe to my newsletter or connect with me on LinkedIn.