The Optional
Life

In my final semester of university, the woman I wanted to build a life with was in Japan, and I was in Washington, D.C. Nobody was going to employ me in America and let me live on the other side of the world, so the income would have to be built. I started a cleaning company with seven hundred dollars. I didn’t have the word for it then, but I was buying an option: the right to live where my life was, rather than where a job happened to be.

Looking back, that has been the pattern of my whole life. I’ve been building options, first in my own life and then in other people’s. Inova Local gave owners the option of not answering their own phones. The Local Business MBA gives students the option of a business of their own. The Optional Owner is the same idea with its name finally attached: a business that makes its owner’s presence a choice.

What an option is

An option is a right without an obligation. You pay something small to hold it, and it pays you when the world changes in a way you couldn’t have predicted. Nassim Nicholas Taleb puts it in one line: “Options, any options, by allowing you more upside than downside, are vectors of antifragility.”1 The important word is right. An option you’re forced to use was never an option.

Holding options is different from frantically keeping every door open. You hold one so that you don’t have to decide yet, and so that when you do decide, the decision is free.

The four I keep coming back to

The Optional Owner is about one kind of option: your time, and whether your business needs it. Over the years I’ve come to think it works best alongside four others.

Money

The FIRE movement, financial independence and early retirement, traces much of its thinking to a 1992 book by Vicki Robin and Joe Dominguez, Your Money or Your Life, which asked readers to see money as something they trade their life energy for.2 Its arithmetic comes from a 1994 paper by a financial planner, William Bengen, who tested withdrawal rates against US market history. Taking 4% of a portfolio in the first year, then adjusting for inflation, would have lasted at least thirty years in every period he tested.3 Turned around, that becomes the movement’s rule of thumb: about twenty-five times your yearly spending. It’s a guide drawn from one country’s past rather than a promise, and it has been argued over ever since.

FIRE is usually described as an early exit from work. I think its real gift is smaller and better: the freedom to say no. Money set aside is an option on every decision that follows it: the client you can turn away, the deal you don’t have to take, the year you can spend building something slowly.

Body

Movement practice is the option you carry everywhere. Mine is plain: long trail miles with the dog, handstands wherever the ground is flat, and the old basics, ground, hang and carry, done barefoot and outside when I can. What I’m after is range more than any one skill: being able to get down to the floor and back up, to carry, to climb and to run when I need to, for as many years as possible.

Place

I’m British-American, and I live in Japan. A passport is the plainest geographic option there is: the right to live and work somewhere, kept in a drawer until you need it. A second language, a residence permit and friends in more than one country do the same job more slowly. Each one widens the map of where your life could happen. And when life changes, as mine did when the person I loved was on the other side of the world, the size of that map decides how hard the change will be.

Work

Entrepreneurship takes your career into your own hands, for better and for worse. The better is plain: you decide what you work on and with whom, and the skills travel with you to whatever you build next. The worse deserves honesty. Only about a third of the business establishments opened in the United States in 2013 were still operating ten years later, by the Bureau of Labor Statistics’ count.5 A business of your own is an option on your working life, and it can also put every risk you have in one place.

That’s where the fifth option comes in, the one this site is about. A business that needs its owner is a job with extra risk attached. One that doesn’t is an option on your time, and The Owner Independence Ladder measures how much of that option you already hold.

The trap

Options have a failure mode. You can get so good at keeping doors open that you never walk through one. Pete Davis calls it Infinite Browsing Mode, and in Dedicated he argues that keeping our options open has become the defining habit of our moment.6 An option you never use is only a cost.

This is the part the word optionality can hide. The aim was always to be free to choose, and then to choose: to give yourself to something without being trapped by it.

Options in the foundations, so that you can commit to what matters without being trapped by it.

Beginner’s mind

Zen has its own word for this, though it never says option. Shunryu Suzuki opens Zen Mind, Beginner’s Mind with it: “In the beginner’s mind there are many possibilities, but in the expert’s there are few.”7 Beginner’s mind is optionality of attention. The expert knows how things go, and has stopped seeing the other ways they could go. The beginner still sees them.

And yet a Zen life is about as committed as a life gets: the same posture, the same breath, every day, for decades. Zen keeps the options open in the one place they matter most, the mind, and closes them almost everywhere else. Sitting daily has taught me that the two belong together. Freedom without commitment is restlessness. Commitment without freedom is a cage.

Space, then pursuit

Computer scientists have a name for the balance: the explore/exploit trade-off. Brian Christian and Tom Griffiths explain it in Algorithms to Live By: explore while you still have time to use what you learn, and exploit, going deep on what you know is good, as that time runs short.8 Options are what make the exploring affordable. They give you room to try things that don’t have to pay, and to notice what you care about before you’ve committed your life to it.

Then they let you pursue it. When our son arrived this year, the question that came with him was what all the building had been for. The options gave me room to ask it, and room to act on the answer: more time at home, the writing and the teaching, and the sitting underneath it all.

That’s the order I’d suggest to anyone. Build the options first, in money, body, place, work and time. Use them to make space. Use the space to find out what matters to you. Then spend the options on it, gladly.

An options audit

Five questions, one for each option, with a first step for each. Answer them honestly, once a year.

The options were never the point. They’re the clearing in the wood, and what you build there is yours to choose.