I have spent ten years making businesses need me less. For most of that time I thought I was working on separate projects, one after another, each a sensible next step from the last. A cleaning company. A staffing agency. A school. From the outside it probably looked like a series of pivots. From the inside it felt like a series of pivots too.
Only recently did I see what had actually been happening. I had been asking the same question the whole time, a little deeper each time.
Where can the owner work?
Think Maids asked the first version. I needed to be in Japan and the company needed to be in Washington, so the question was purely practical: can the owner of a local business work from somewhere else? After eight years and a sale to an industry buyer, the answer was yes. Anywhere, it turned out.
What actually needs the owner?
Inova Local asked the next question down. Once location stopped mattering, the real question appeared underneath it: of everything an owner does, how much genuinely requires them? The answer, across companies all over North America, was far less than most owners believed. With good assistants, written systems and a little software, most of the office could be done by someone else, and done well.
Can other people do it too?
The Local Business MBA asked whether any of this was specific to me. It wasn’t. More than 250 students in sixteen-plus countries have taken the model into their own towns, and thousands of operators now run some version of it.
What kind of business are we building?
Somewhere along the way I stopped designing businesses for growth and started designing them backwards from the life I wanted. That sounds like a slogan, so here is what it meant in practice: deciding first how much of my time the business could have, and where, and then building a company that fitted inside that, rather than building the biggest company possible and seeing what time was left over.
It changed small decisions constantly. When someone asked whether I would move our cleaners from contractors to employees, I said not really: my primary goal was freedom, not a big business.
What does progress mean?
Designing that way changed what counted as progress. Revenue still mattered, but it stopped being the scoreboard. Better measures were things like how many decisions still reached me, how long the business could run without a message from me, and how the team felt at the end of a hard week. And the growth came anyway. I have come to think growth is what a well-run business does, and a poor reason to run one.
What was the freedom for?
Then I sold the two companies I had started, our son was born, and the last question arrived. For a decade I had been chasing freedom from: from the phone, the schedule, the business needing me. That turns out to be only half of it. The other half is freedom to. To disappear for a few months when your son is born. To take a Tuesday afternoon. To start something new because you want to, not because you have to.
Independence, and then options
This is the distinction I most want to develop, so let me put it plainly. Owner independence is freedom from: the company doesn’t need me. It is valuable and hard to build, and most advice about removing yourself from your business stops there.
Optionality is what independence makes possible. Because the business doesn’t need you, you get to decide what part it plays in your life. You can work hard on it because you enjoy it. You can step back for a season. You can sell it, keep it, or build the next thing alongside it.
Independence is the floor. Options are the point.
The Optional Owner
That is where the decade lands. I call it The Optional Owner: a business designed to create options for its owner. Build it. Systemise it. Step back from it. Then decide, deliberately, where you want to be useful.
It explains my own path better than I could at the time. Each company was an attempt at the same question, asked with a little more depth: where can the owner work, what actually needs the owner, can others do it, what are we building, what counts as progress, and what was all of it for. I don’t think I have finished asking it. I suspect that is the point.
If this sounds like the question you are circling too, the letter is where I keep asking it, most weeks.