Do I Own My Business, or Does it Own Me?

A friend recently shared an article that describes Unschool Adventures, my little travel tour business, with scary precision:

Let me ask you a question. If you went overseas for six months leaving your business behind, when you came back would it be in better or worse shape than you left it? Would you even have a business left?

If your answered negatively to either of these questions, then it’s likely you don’t have a business – rather you ARE the business. . . .

Don’t get me wrong, [such a business owner] may be financially successful. Their business may be thriving with a loyal base of customers but the problem is they are stuck – shackled to their business.

If they were to leave or get sick for an extended period of time, their business would cease to exist.

Yup, that’s pretty accurate. Unschool Adventures is me. Although I hire staff assistants on the trips I run—and once in a blue moon an entire trip happens without me—if I completely ignored my business, ceased my marketing efforts, or attempted to outsource everything, it would soon fold.

The alternative to the one-man business show is a business that’s built on systems: one where the individuals are replaceable, because their job functions are well-documented and new people can be trained to do them.

The thing is, I like being in the muck. I like working face-to-face with the young people I serve. I like traveling. I like feeling special and irreplaceable rather than being a shadowy owner in the background. I created Unschool Adventures to enable a certain kind of lifestyle for myself, and it’s succeeded wildly in that regard.

The one-man business show also feels honest. It makes me feel like I’m a “working Joe” in the small-business sense: someone struggling day to day to keep the doors open. In contrast, the fully systemized business strikes me as smarmy, especially given this example in the artcle.

The poster child for business systems is McDonalds. This is a complex, worldwide, multi-billion dollar business that is essentially run by pimply teenagers who can’t even be trusted to make their beds.

How do they do this?

They manage to run this hugely successful and profitable business because they have amazing business systems. Their operations manual covers everything from hiring to product delivery to customer interaction.

Do I really want to emulate McDonalds? Do I want to create an enterprise that so efficiently depersonalizes everything that it might as well be run by robots? No, I don’t.

But I do think I have something to learn here.

My Weird Family Goals

Here’s what inspired all this. I’m almost 34, and in the past year I’ve been thinking more about the kind of life I lead with my (future) kids and (future) long-term lady partner. Yesterday, while contemplating that business article, I found myself writing this:


To explain: When I have kids, I want to do awesome stuff with them. I want to be that weirdo adventure family. Some of my favorite ideas include:

  • Living abroad for 1-2 years with my kid(s) during the magical language-sponge years
  • Thru-hiking the Pacific Crest Trail as a family [inspired by this 10-year-old girl, who I met]
  • Going on long road trips (6+ months) across the Americas [inspired by this family]

Here’s the rub: I probably won’t be able to do these things if I continue running Unschool Adventures as it does today.

(Hell, I probably won’t even be able to hold down a long-term relationship if I continue running Unschool Adventures as I do today! But that’s a different story.)

I’ve built Unschool Adventures into a quasi-location-indepent business. It’s more like, “choose your location dependence a few times a year.” I can choose to run a trip anywhere in the world, but when it’s go-time, I need to be in that location 24/7. Then, in between trips, I get to be location-independent again. That’s nice. But I’m still not able to really ignore the business. I’ve built myself in too far.

To confidently move toward my goals, I’d need a location-independent business that I could also walk away from for 6+ months. In other words, I’d need the same 4-Hour Work Week style “freedom business” that I railed against a year ago. Gosh, what a hypocrite I am!

The Adulting of the Lifestyle Business Owner

Adulting is the act of holding responsibilities such as a 9-5 job, a mortgage/rent, a car payment, or anything else that makes one think of grown-ups. While I consider myself an adult and I hold pretty serious responsibilities (like the lives of teenagers in foreign countries), I’ve also carefully avoided 9-5 jobs, mortgages, rent payments, etc., for all my adult life. No regrets there. I love how much compensation I take home in the form of time.

“Adulting” doesn’t mean “settling down” for me, obviously. Perhaps it means: creating a systems-based business that offers sustainable and truly location-independent income. 

Something that I can manage from a PCT trail stop, a city in South America, a café in Anytown, America.

Something that doesn’t require 6-week+ international voyages, which are great right now but unfeasible with a small child in tow.

Something as honest and meaningful as leading life-changing trips for teenagers.

Yup, that sounds about right. Not easy, not quick, and perhaps not feasible—but right.

I’ll let you know where I take this idea.



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