One of my friends who has a great business is looking for a job. For many people, “having a great business” and “looking for a job” are incompatible. If you had a great business, you wouldn’t be looking for a job, right?


They’re looking for a job because they’ve realized that their business isn’t the right container for their skillset. Some consulting gigs over the last year have shown them what they can do with the right team setup. But their business niche isn’t sufficiently large enough to build that kind of team without completely changing their business model. Even if they changed the model, they still wouldn’t get to do what they do best.

The Trouble with Strap-Ups

Let’s unpack “they still wouldn’t get to do what they do best” bit. The skills and focus required to scale a strap-up (bootstrap + startup) are heavily centered on sales, talent cultivation and management, and team development — in simplistic terms, the generalized executive functions. At each successive growth plateau, my friend would become more removed from the work of the business to work on the business. My friend would spend ever-larger portion of their days in meetings, communication, management, financial gymnastics, strategic networking, and strategy-execution troubleshooting with ever-smaller percentages of direct-to-customer value creation.

Some wide-opportunity businesses have such a high market ceiling that they generate customers fast enough for the founders to cross-train or hire people to replace themselves. This is much harder to do with service-centric strap-ups, even when they have a high market ceiling. There’s typically a deep expertise set that people providing the service have to be validated, trained, and compensated for, all three of which can take 9-24 months to do. You can’t just pull someone off the street and put them in the seat with two weeks of training.

My friend would need to spend the next three to five years pivoting their business model to replace themselves, but even then, the people creating value wouldn’t be creating the value that best aligns with the work that lights my friend up. They’d be managing service providers, not running a marketing team that sells a company’s products. So, after all that work, they still wouldn’t be doing the work they want to grow into right now.

The die-hard entrepreneurs reading this article probably thought, “Well, go build another business!” But my friend doesn’t want to build an agency or spend the next decade or two building a business that could support a 5-10 person marketing team. There’s a more direct path to doing that kind of work.

Others may say that there’s no such thing as a great service business because they’re always exchanging time for dollars. I’ve already written a post to rebut that nonsense, so I won’t do it again here.

Choosing to Thrive

I’m excited for my friend’s journey, just as I was Ally’s and another client who got acqui-hired last year. It’s not just that they chose to thrive, but that they chose to thrive while clearing out the head trash that accrues from years of absorbing the entrepreneurial culture’s bullshit. While few in the entrepreneurial culture will admit, a very strong vibe exists that says jobs are for people who aren’t good enough to be an entrepreneur, that for entrepreneurship to not be for someone is a defect of character and competency. With that vibe in play, getting a job is tantamount to washing out.

When the entrepreneurial path is the path of someone’s thriving, I’m all for it. When it’s not, I’m all for them exploring a different path as soon as possible. Life is too short to not do our best work.

My friend might get a job and hate the choice 18 months later. Maybe they’ll have to go through two or three jobs to find the right one. Maybe they’ll stumble upon some hybrid option that works really well for them.

But they already know the path they’re on isn’t taking them where they’re called to go. The courageous path — and the right path — is for them to step into the void, create a new opportunity, and figure out the rest as they go. (Tweet this.)

And you better believe they won’t be doing it alone.

Oh, and you may be curious to know that my friend started their new job a few weeks ago!

Originally published at


  • Charlie Gilkey

    Author, Speaker, Business Strategist, Coach

    Charlie Gilkey helps people start finish the stuff that matters. He's the founder of Productive Flourishing, author of the forthcoming Start Finishing and The Small Business Lifecycle, and host of the Productive Flourishing podcast. Prior to starting Productive Flourishing, Charlie was a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon.