Back to “Reality”

Ope, there goes gravity. Or am I defying gravity?

I think it’s about time we wrap up this little adventure. Not the adventure inherent in life, of course, but my sabbatical. I ventured into the AT mainly because I wasn’t ready to go back to work, but as I neared Katahdin, I realized I was tired. Physically, of course, but also mentally and emotionally. After over two and a half years wandering far from home, I started to crave stability again.

I will always love adventure, and I hope I get to go on many more in my lifetime. However, I also recognize that life appreciates equilibrium, and, as an extension of life, I was beginning to feel misaligned once again.

I left my career and my home because I had spent so much of my early adulthood on the grind, yearning for the standard societal definition of success. I went on sabbatical because I needed some balance in my life. I had been lucky enough to recognize that I needed a pause, to take a big deep breath and reassess who I wanted to be and how I wanted to live.

That breath had taken me to India and all over Asia and Europe. It had taken me to deep and fulfilling moments with my family, and now on this journey in the wilderness. But now I could feel the pull calling me back home.

However, before we moved back into our house, Toriya wanted to take one more visit to her parents in Japan. We figured since we were making the long flight to Asia, we might as well make the most of it, so we added one final victory lap to our travels. We spent a month in Japan, another month in Vietnam, and then in Thailand.

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Even though I was excited to get home, I was still able to be fully present with those places. However, one thing was different this time around.

During our stint in India, I made a point of not thinking about what I wanted to do for work when I returned home. I knew that my frantic mind would be clawing and scratching at every idea and opportunity to build another career and acquire wealth. I was leaving to distance myself from those old mental patterns.

Now, at the prospect of returning home and taking responsibility for a mortgage again, I knew that it was time to live from the equilibrium that I had been seeking for so long. It was time to learn to be in the world while still recognizing that I am not necessarily of it.

Could I pursue a career and make money without it consuming me? This was the question that poked at my mind.

While in Japan, I considered various options for my next career. I was trying to find something at the crossroads of what I was good at, what I was passionate about, and what would serve other people (whatever that means), or, at the very least, do no harm.

I’ve always loved writing, so I decided to start a Substack (welcome!). I didn’t have many intentions of making money from it, though I was open to the possibility. I knew, however, that it would not be my main squeeze, so to speak.

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Then one morning, while I was working out, an idea struck me.

During my ten years in sales, recruitment, and leadership, I found that the activity I loved most, and where I often made the biggest impact, was coaching people one-on-one. What if I became a full-time coach?

Coaching is one of the few activities where I lose track of time. It’s one of the few things that leaves me feeling lighter when I finish than when I started. I loved it enough to do it for free, but it was also a service I was paid well for.

That made it a pretty compelling candidate for my next career. Still, I knew I wanted to build something, so coaching felt like only part of the picture.

I began developing an idea for a platform—something a bit like YouTube but closer to MasterClass—where people could access curated material from vetted professionals rather than being misled by self-appointed gurus. The platform itself would be free or inexpensive, and its main purpose would be to connect people with the coaches and experts they resonated with. It felt meaningful. It seemed to blend my interests with something that could genuinely help people.

So I started working on a business plan. I began networking, started designing the website, and even reached out to people I had coached before to gauge their interest.

But while all this was happening, something felt slightly off. The idea felt good; great, even, but something was missing.

In my life, when the right path has come into view, I’ve usually known it, without doubt. A calm sense of certainty has appeared only a few times at the more important crossroads of my life, but when it does, I recognize it.

This idea felt close, but not quite there. So I kept experimenting with it while staying open to what I might be missing.

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Then, while we were in Vietnam visiting Ninh Binh, I spoke with an old mentor of mine. He was the first real boss I ever had in college, when I worked at his startup, Tuition Specialists.

Through a mutual friend, I heard that he had been buying small businesses since 2019. Not only had he bought his own, but he had helped a few other people, including his wife, do the same. It intrigued me, so we scheduled a call.

During that first conversation, as he explained the process, the benefits, the risks, and the basic model, the lightning bolt struck.

This was what I wanted to do.

Not just buy a small business for myself, but help him help other people do the same. At first, I couldn’t fully explain why it resonated so strongly, but I think a lot of it had to do with him.

Will is one of the most sane people I know.

He’s one of the few people I’ve met who plays in the material world, has done well professionally and financially, and yet has remained deeply grounded. That’s not to say he never gets stressed, but he handles life with a humanity and authenticity that I trust. It felt like the kind of energy I wanted to be around.

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I was afraid to get back into business, especially after coming from such a hustle-driven environment. I’m still sensitive to the diseased quality that often surrounds ambition, money, and status.

I feel a bit like a recovering addict—wary of putting myself back into an environment where the temptation to fall into old patterns might be overwhelming. I knew that if I wasn’t careful, I could easily slip back into my old rise-and-grind mentality and lose the perspective I had fought so hard to gain.

Because of that, I felt I needed one of two things: either to work for myself and carefully shape my environment, or to find a person or company that aligned closely with my values.

I do believe those companies exist, but I have yet to run into many of them.

So it seemed like the better choice to pair my interest in entrepreneurship with the gap in availability of conscious businesses, and just start one myself.

When I approached Will with the idea of building something together, he responded with similar enthusiasm. He was still involved in another company he had started, and thus had expected this to remain a side project for a few years. But with me on board, we could move up the timeline.

This was the feeling I had been looking for. It felt right.

That calm certainty returned, the same kind that had guided me through other important turning points in my life, and I was ecstatic. I was so excited, in fact, that I had trouble sleeping for the first few nights. Parallel to all the previous moments of calm clarity in my life, I remember calling my mom from the mountains of Ninh Binh and telling her I had found what I was supposed to do next.

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And it wasn’t just excitement about working with Will. The deeper I looked into the idea, the more tangible it felt.

I had spent years investing in the stock market and in real estate with modest returns. Enough, at least, to help fund this three-year sabbatical. But small-business investing seemed like a different category altogether.

The return potential was far greater, but so was the risk. That was what made the idea compelling: if we could help reduce that risk, we could open access to an opportunity that most normal people never get to participate in. I

thought of my sisters and their families, my mom and stepdad, and close friends. People I care about. People I would love to help.

Then the vision expanded even further.

In addition to helping people buy small businesses, we began imagining a system that could help manage them as well, further reducing risk and improving the quality of the investment. Someone could invest in a business without becoming a full-time operator or sacrificing their job or family life.

Because of Will’s background in systems and operational management, we had a real path toward building that.

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I apologize. I realize I’ve been ranting for a while now, but as you can see, I’m still quite excited.

We’ve been working on the idea for a little over four months now, and it’s really starting to come together. I’ve been searching for a business to invest in for myself and have been building the systems and processes to do so at scale for others.

However, while being my own boss and having what I consider a very healthy partner to work with, I’ve still noticed old tendencies creeping back.

There have been days when I’ve caught myself frantically trying to check everything off my to-do list. Old habits die hard.

Even though I’ve been moving the mission forward steadily, that old part of my brain interjects, “You’re not doing enough. Move faster!”

But I catch those low-frequency thoughts faster now. Instead of having that unstable energy dominate entire months or years of my life, it might dominate an afternoon, or sometimes only an hour.

I still set aside time for three sittings a day and for other aspects of my spiritual practice. And whereas I used to voraciously read business and self-development books, I now spend most of my reading time on spiritual texts and philosophical contemplation.

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I’m definitely not out of the woods by any means. After all, the ego is trickiest when you think you’ve got it beat. My biggest concern is that if I get overtaken by the insanity of the world again, truly overtaken, then I will be unaware of it. So I’m doing my best to remain vigilant.

It’s a razor-thin line I’m attempting to walk, and I fear I might fall. In fact, I know I will. I just hope I’m conscious enough to get back on it when I do.

I chose to re-enter society not because I don’t care deeply about self-realization, but because I felt called to bring that practice into daily living.

I felt called to build a homestead and have a garden again. I felt called to start a family, and I still felt called to experiment with business. Only this time, I sincerely hope I can carry my breath with me as I toe the line of twilight.

I am not a candle meant to be burned at both ends. I recognize that my worth and value do not come from my achievements or output. Whether I can remember that as I step back into society, only time will tell.

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The end of one adventure is simply the beginning of the next.

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I got to be there for the birth of my nephew, Jack.

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Spending my birthday in Japan with Toriya’s parents, Todd and Rachel!

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Enjoying a beautiful sunset in Ninh Binh, Vietnam.

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When I was 18, all I wanted was to go out on my own. Now, all I want is to be with my family.