How Comfortable Are You With Being Uncomfortable?

Starting my own business required a mental shift I wasn't fully prepared for, even after two decades in the workforce.

For most of those twenty years, I held roles at startups and mid-market tech companies, working my way up to the senior rungs of middle management. I was a skilled leader of teams. I had a good salary, good benefits, and a level of stability that comes with being a few rungs up a corporate ladder.

But if I'm honest, I wasn't doing a ton of the actual work anymore. It was mostly meetings: reviewing other people's work, making decisions about other people's work, talking about work that other people were doing.

Now I do all of it myself. Sales is on me. Marketing is on me. Client work, operations, finance, all of it, on me. It's a completely different motion, and most days, I genuinely love it.

But here's what still gets me sometimes: wondering whether this is what I'll be doing five or ten years from now.

There's a sense of "long-term-ness" that comes with having a career path inside a company or an industry, a ladder you climb, even across different employers. A sense of security, however false it might actually be in practice.

Doing my own thing means giving that up. It means sitting with questions I never used to ask myself as an employee: What if this doesn't work? What if it does, and I'm not ready for what that brings? What if I get tired of it? Would I even be employable again if I needed to be? Could I go back to a more traditional path if I wanted to, and would I want to?

I never asked myself any of those questions when I had a steady paycheck and a title. As an entrepreneur, they show up more often than I'd like to admit, and a lot of the work is just telling those thoughts to quiet down so I can get back to the actual work.

What it really comes down to is this: entrepreneurship means putting faith in yourself when there's no external structure backing that faith up. It means pursuing something because it matters to you, not because someone else built the path for you. It means being all-in even when you're scared, maybe especially when you're scared.

If you're sitting on the edge of making a similar leap, I won't pretend the uncertainty goes away once you jump. It doesn't. But the alternative, staying comfortable in something that no longer fits, has its own quiet cost too. At some point, the discomfort of staying still becomes louder than the discomfort of moving.

Originally posted on Linkedin. Join the conversation here.

Hi5,

LD 🌶️