“Every morning I roll out of bed and ask myself, what should I do today?”

These were the very first words I wrote on Deep Dish, 2.5 years ago. I’m as surprised as anyone to find that I still have that same untrammelled freedom today. It’s been transformative in all sorts of ways, which is why I’m such a relentless booster for personal autonomy.

In fact, if I had to try and pin down the central theme of this blog, it’s exactly that: opening up your options. I’m not going to stop writing about that stuff any time soon.

But I do want to introduce a new through-line. A bit of character development, if you will. Something I’ve learned the hard way during this extended sabbatical is that you can absolutely have too much of a good thing.

Total unconstrained freedom is… well, kind of freaky, actually.

Here are some archetypes:

• The Peter Pan manchild who refuses to grow up
• The Trustafarian rich kid aimlessly wandering the earth
• The attractive New Yorker who constantly dates, but never settles
• The dilettante who flits from job to job without ever pushing the boundaries
• The early retiree who triumphantly quits her job, then falls into a depression

Let’s start with something simple.

The One Note Solo

When you’re learning to improvise a guitar lead, the fretboard is huge and distracting. There are 49 unique tones across ~144 positions, which approaches infinity if you add harmonics and bends. So you start by confining yourself to a single note.

Later on, when you’re a master musician who knows the fretboard inside out and upside down, you write one of the greatest solos of all time by…confining yourself to a single note.

Constraints can be liberating. Just ask a programmer, or a writer, or anyone who does creative work. The total space of all possibilities is so vast that it’s unworkable. You have to carve off one tiny little sector, and think inside the box.

I don’t know who coined the term constraints that liberate, but the concept goes back at least a couple of millennia. Cicero wrote that to be completely free, one must become a slave to a set of laws.

Another way of saying this is that by restricting your freedom along one dimension, you can create more freedom along another dimension. Almost every life philosophy—minimalism, frugality, Christianity, the Paleo diet, whatever—boils down to some kind of tradeoff like this. Do this and not that, and you get to retire early/lose weight/ascend to heaven.

Constraints seem to come in handy during two distinct phases of life. There’s one set that helps you generate better options in the first place. Then there’s another set that helps you exercise your options.

Pruning the Possibility Tree

A quick definition of optionality:

Optionality = the right, but not the obligation, to take an action

UPDATE: My book on this subject, Optionality: How to Survive and Thrive in a Volatile World, is available now

Optionality is not the same thing as merely having lots of choices. If your crippling student loan debt effectively makes you an indentured servant, the fact that you can choose between 43 brands of cereal for breakfast doesn’t give you much in the way of optionality. If you’re in prison, and the guards sometimes let you choose what to watch on the telly, same again. The quality of choices matters.

The single most powerful way to open up your options is to a) have more money, or b) require less of it in the first place. That’s why I write a bunch about personal finance and frugality, with a secondary focus on the other raw materials of optionality: health, knowledge/skills, and social capital.

If you want to build optionality in any of these domains, perversely, you have to limit your choices. Imagine all the potential actions you could take as a giant decision tree of branching possibilities.

Now imagine taking to it with a giant pair of pruning shears, Edward Scissorhands-style:

Finally, all my teenage years as a part-time orchard labourer are about to pay off! As it turns out, pruning trees isn’t about making them look stylish and sophisticated. It’s about improving the quality of the fruit they bear. If you don’t lop off some of the branches, you end up with a million misshapen little nubs. You have to be surprisingly ruthless about it, too.

What might that look like?

Perhaps you limit your screen time, and divert that surplus to productive work instead. Or you ban yourself from online shopping, so you can repay a debt that’s messing up your credit rating. Or you make a rule not to keep junk food in the house. Or you wear the same clothes or eat the same meals every day, to free up mental bandwidth for more important decisions.

You’re constraining your short-term choices, in order to build long-term optionality.

This initial round of pruning dramatically improves the quality of choices available to you. From the tip of each branch sprouts a fat purple fruit. But which ones to pluck?

Withered on the Vine

There’s a famous passage in Sylvia Plath’s The Bell Jar, in which Esther has a disturbing vision of a fig tree:

One fig was a husband and a happy home and children, and another fig was a famous poet and another fig was a brilliant professor, and another fig was Ee Gee, the amazing editor, and another fig was Europe and Africa and South America, and another fig was Constantin and Socrates and Attila and a pack of other lovers with queer names and offbeat professions, and another fig was an Olympic lady crew champion, and beyond and above these figs were many more figs I couldn’t quite make out. I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn’t make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.

Generating better options is much more important than being a perfect decision-maker. But after a certain point, you have to do something. If you never exercised any options, they’d wither and rot. You’d just keep hoarding more and more ‘maybes’, forever and ever, until you died.

So once again, you have to prune the tree. This time, all the branches have appealing outcomes: you’re not just dithering over 43 brands of breakfast cereal. But you have to say no to most of them, commit to something, and then grasp onto it with both hands.

How Much Freedom is Too Much Freedom?

The tension between freedom and limitations comes up in enough areas of life that I want to prod at it from a few different angles.

Instead of making vague mumbling noises about future posts, I’ll prune my own possibility tree right now. The details will probably change, but here’s a rough overview of what I’m thinking:

1. Constraints That Liberate
2. Office Hours
3. Same Salad, Different Day
4. Better to Reign in Hell Than Serve in Heaven
5. The Embarrassing Problem of Premature Exploitation
6. No Man is an Island
7. The Sigmoid Curve
8. Escape from Neverland
9. Pandora’s Box

These will run in between other posts, as and when I feel like writing them. Each of them should stand alone, but I thought it would be fun to explicitly link them into a loose sequence.

I was so chuffed when I wrote those words: “every morning I roll out of bed and ask myself, what should I do today?” but, uh… that no longer seems like a desirable state of existence.

The idea is to write about some of the constraints and rules I’ve added back into my life, and why I’ve circled back to convention (with a few twists).

You can think of this series as my journey to ‘discover’ ancient wisdom, in the sense that Columbus ‘discovered’ the Americas, i.e. entirely by accident, driven by hubris, and 15,000 years too late. All aboard!

Not Sure What the Future Holds? Get Your Copy of Optionality Now.