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Am I Crazy?

I (32M) am in a bit of a crossroads and would love to hear from the entrepreneurial minds here. I currently work in cybersecurity, earning around $250K—a number I never thought I’d hit when I first started out. I worked insanely hard to get here, and I am so, so grateful for the opportunities I’ve had. But here’s the thing: I kinda want to switch it up.

Before I got into cybersecurity, I was actually a journeyman plumber. I loved working with my hands, solving problems, and getting out in the field. But the union system felt like a bottleneck, and I saw no real path up. So, 10 years ago, I pivoted into cybersecurity (perfect timing, by the way), and it’s been a fantastic career.

Along the way, I dabbled in business: Consulted on the side ($62K Y1 → $88K Y2 → $97K Y3). Flipped homes with my wife (first in 2017, second in 2019, then we built our current house). Got my MBA (because that’s what you do).

Now, I’m thinking of making a big leap—starting my own general contracting company and building a home. (We were the general contractor of our 2019 build) • We already own two lots (bought in 2019). • I want to invest $300K–$400K into a build and create something beautiful and functional. • My wife and I are homesteading nerds, so we’d design it as a homestead-ready home—fruit trees, goat pen, duck pond, the works. The dream is to build not just houses, but lifestyles.

I know how to build businesses and lead people, and I still love the trades. Plus, let’s be honest: when my 5-year-old grows up, the trades are probably going to be one of the most secure career paths.

I tolerate my current job, but I don’t feel like I’m that great at cybersecurity. I’m great at hustling, facilitating, and making things happen, but I don’t live and breathe cyber like some of my peers. I plan to keep working remotely for the next year, stacking cash and preparing. Eventually, RTO (return to office) will come, and that might be my moment to jump.

We have a 6-month emergency fund, so while this is a calculated risk, it’s still a risk.

So… am I dumb?

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Am I Crazy?

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