How I Became the Black Sheep Without Trying To

10d • 📝

I was working for a non-profit Christian organization in a full-time position that I had pursued for 8 years.

On paper, it sounded meaningful. Stable. Faith-centered. Respectable.

But inside? I was suffocating.

Every time I tried to expand my role, bring new ideas to the table, or do anything creative, I was throttled by management. They didn’t want growth. They didn’t want innovation. They didn’t want me—they wanted the reports done on time every month and nothing more. At least that's how I felt.

My creative side was starving.

To make it more complicated, my wife and I lived on property owned by the organization. That meant work didn’t end at 5 pm. There was an unspoken level of control over our personal lives, too. What we did, what we pursued, what was “appropriate.”

The pay was low. The ceiling was fixed. And the entrepreneurial drive in me had nowhere to go.

So I tried starting side hustles.

Every time I did, management found a way to shut it down.

Not because it conflicted with my work.

Not because it was unethical.

But because it didn’t fit the box.

Over time, I became depressed.

And that scared me—because I’d been there before earlier in my life (suicidal ideation, etc.), and I knew I couldn’t go back to that mental state.

I committed myself that I would stay three years and finish well.

I kept that commitment.

I did the job with integrity until the very end.

And then… we were gone.

My wife and I packed up everything we owned and started what turned into a year-long road trip, circling the entire country. No master plan. Just space to breathe, think, pray, and listen.

It was during that year—away from pressure, expectations, and noise—that something clicked.

I didn’t just want to be an entrepreneur.

I realized I was called to it.

Seven years ago, I started my first successful business. I had no idea how much fun it would be. Yes—it’s been harder. Yes—there have been massive ups and downs. But I wouldn’t change that decision for anything.

I’ve started other businesses since then. Most failed. One more succeeded—that my wife now runs, and it’s been a huge blessing to our family.

Right now, I’m in another hard season.

I’m feeling called to make a major pivot in my first business.

I’m praying.

Seeking counsel.

Working long hours.

Testing systems.

Rebuilding structures.

Taking risks.

So, this post is not a victory lap. I don’t have it all figured out.

I’m still on the journey.

My faith has been central through all of it, and that's the most important part.

I’m married to an incredible wife who trusts me. I have two beautiful kids who intensify life in the best way. I’m deeply thankful.

And still… this path has been lonely.

That’s why I resonate with the idea of being the “black sheep.”

I'm fortunate to have joined a Bible study with a group of men—many of them entrepreneurs— about 6 years ago, and that consistent weekly brotherhood has been life-giving in ways I didn’t realize I needed.

I’m excited to experience more of that kind of community here, encouraging one another.

So I’ll ask you directly:

👉 Have you ever been in a role or season that looked “right” on the outside but was draining you on the inside?

👉 Where are you currently feeling tension in your life?

👉 What kind of brotherhood do you actually need right now?

You don’t need to over share.

You don’t need to impress anyone.

Just be honest. I'd like to get to know you more.

Glad we’re walking this road together.

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