Carving My Own Path

Get passive income, they said. It will be fun, they said.

I was miserable.

It just took sobbing uncontrollably on a zoom call with one of my investors to realize it. Not my best look. 

I had a successful business with the financial freedom to meet friends for coffee in the middle of the day, visit Florida a few times a year, and occasionally play Pickleball with my husband in the afternoons. I was living the new American dream, a page ripped straight out of 4-Hour Work Week. 

Why was I miserable? 

It wasn’t like I hadn’t considered my career choices. It was the main thing I had considered my entire adult life. I strategically veered off the traditional path. I spent years chasing my entrepreneurial dreams to avoid this very feeling – miserable. 

So, how did I get here?

I was a product of startup culture. Instead of blindly following the traditional path, I blindly followed the path of other tech founders; raising a lot of money and hustling for a place among the competition. I learned how to play every entrepreneurial role - trying each one on like a new outfit. I hustled with the best of them, outrunning my thoughts until I was soul-crushed and burnt out.

Then when my husband suggested an alternative option to the stereotypical startup life, one of freedom and flexibility, I changed outfits again. I set up operating systems, hired people, and made it so I wasn’t putting every waking hour into the business. I even hired a coach to hold me accountable to this new way of life. I thought I had nailed it. Successful satisfaction was just around the corner… until it wasn’t. 

I begged my coach to tell me what exactly to do with my free time. Though I hated the constant striving of startup hustle, I also hated feeling disconnected from a business on autopilot. 

Cladwell had always lived at the intersection of a tech and lifestyle business. The call with my investor gave me the pause I needed to realize I have always defaulted to hustling down a predefined path instead of trusting my gut long enough to carve out my own.  

The writer in me wants to tell you this ‘aha’ moment instantly led me to a new success. But the truth is, I’m learning and exploring what it looks like to unlearn the “shoulds” of even those closest to me. 

I’m navigating the unfamiliar territory of trusting my intuition. But I can already feel the energy, and creativity it brings. I’m leaning into the pull toward a career and a life that looks like who I was made to be.

Carving my own path, step by step.