Manage your indefinite optimisms

It’s just a thing I read in this book when I was twelve. The girl in the book has a terrace that’s outside of her bedroom, and she planted flowers on it, and I just loved that. It just kind of always stuck with me. It’s impractical, I’m not gonna try to get a house like that. Uhm, they don’t even make houses like that in Scranton. So, I’m never gonna... [Starts to cry]
—Pam Beesly, The Office

What is indefinite optimism?

Peter Thiel coined the term indefinite optimism in his book Zero to One to identify a flaw that plagues startups. It’s the vague expectation that the future will improve, without any concrete plan for how that improvement will happen. Definite optimism, by contrast, confidently makes plans to bring about a better future.

Indefinite optimism, says Thiel, happens not only to businesses, but also at the broad societal level. He warns us that contemporary America is guilty of it—we have hope that things will improve, but we mostly think the magic of stock market growth will get us there (today you could argue we’re betting it all on an AI-driven productivity boom, which is more of a plan, but think of America just a few years ago, without that hope).

And if America is indefinitely optimistic, maybe I am, too.

The indefinite optimist

Thiel’s diagnosis also applies at the personal, life-planning level, and I’ve found it to be a really useful, if scary, tool for that. When I was in college I had severe indefinite optimism about the future—how could I not? Up to that point everyone had been telling me I had my whole life ahead and that I could be anything I wanted, and they were basically right! So I could take any possible future that sounded kinda cool and entertain it as a serious possibility. A fantasy that doesn’t quite admit it’s a fantasy.

I wondered what it might be like to work at a startup. To run a startup. To manage a team. I wondered what it would be like to live in Ireland for six months and just read and enjoy nature. I assumed I’d get rich enough to afford a personal chef.

And when I graduated college, the indefinite optimism continued. Even though I got a job and planned to stay with it, it never really sunk in how that would limit my future possibilities.

Indefinite? That’s bad :(

In 2018 I traveled to Italy and saw beautiful estate houses with enclosed courtyards. I loved that feature of the architecture. And somewhere deep in my mind, radiating warmth to the rest of my experience but mostly staying out of view, was a thought, “maybe someday.”

“But how would you ever get that? Do they even make houses like that in America?” I don’t know, and I didn’t ask. I was in Italy, enjoying it, and I just felt good with the idea that I could possibly live in a building like that one day. That’s it. That’s what makes it indefinite!

But future hopes come at a cost. To simply appreciate the beautiful courtyard is free, but that’s not what I’m talking about. I’m talking about the inkling of an expectation of some gain in the future. It will either come to pass or it won’t, and if it doesn’t, then I’ll experience that adjustment of expectations as disappointment.

Optimism? That’s good :)

What do you daydream about? What are the pleasant future daydreams you have? The future-fantasies that come with a small spark of “but maybe” that sets the whole thought alight?

It’s ultimately a good thing that you can grab onto ideas that are just at the edge of what’s possible for you. That’s the seed of ambition. That’s the start of the hero’s journey.

But it does need to start. Or, the hero decides this wasn’t the proper journey after all, and that’s fine too. Either way something must be done; passive hope doesn’t work for startups, and it doesn’t work for people.

Make a list

If you sit down and try to make a list of all the indefinite optimisms you quietly harbor, I bet it’ll be difficult. These ideas tend to slip out of your consciousness; you don’t want to examine them, because either you’ll deem them impossible or not worth it (in which case they’re destroyed), or they’ll be loaded up with a plan of work to realize them.

I tried to list mine, but actually most of the list was added periodically in the following two or three years.

Start the list, and just know that it’s there. Then, when you feel that spark of “what if,” that’s when you write it down. I found I could only notice my indefinite optimisms when I was feeling them.

Eventually you’ll have a pretty substantial list of things you’ve secretly hoped for but which you have no plan to get and might not even be possible. Scary stuff!

Return to your list

What then? Do you make a plan to acquire/achieve each thing on the list?

Your indefinite optimisms are not goals. They might become goals, if they hold up under conscious consideration, but they very well might not. They are whimsical—they don’t promise to be worthwhile, and they’re not urgent for you to attend to.

Look at your list a few years after making it. Ideally, look at it when you’re considering undertaking a big life commitment that will collapse your future possibilities:

• going to college

• moving to a new area

• taking a new job

• living with partner

• getting married

• having kids

Then you can ask, “Which items on my list will most likely be ruled out of all future possibility, if I make this commitment?” Maybe you’ll decide to cram a few of them in before taking the leap to the next stage of life. That would be like doing a micro-retirement, but more general.

But this process is not just “plan to get the thing or painfully give it up.” Reality is more forgiving than that! When I revisited my list:

• 7 of the 26 things had since been achieved, just incidentally, without me remembering they were on the list. In retrospect I wondered why I even considered these things “indefinite” at one time. Perhaps by writing them down, I encouraged my subconscious to hold onto them and subtly work toward them.

• 4 items were no longer appealing to me—my interests had changed—so I dropped them with no grief. In fact I always value opportunities to look at my past self and see how I’ve changed.

• 12 items are still possible*, and I moved them into other lists/notes/projects where I can take active steps toward them.

  • *Sometimes your wants are overly specific and demand an overly strict course of action. Loosen them up by asking, “What is it about this that appeals to me?” I wrote down “Live off the grid hunting and gathering for a short time,” but I don’t have wilderness survival skills and I’m not really interested in learning them. What’s the essence of that want? I think it’s just being completely detached from Internet-era technology and being around nature all day every day, and seeing how that changes me. I can do that from a cozy cabin in the woods; it’s certainly possible in my future.

• And 3 items, I still would’ve liked, but I don’t think they’ll happen in my life. So I mourn them a bit, which is really just mourning the mortal nature of man; we’ll die someday, there’s never enough time to do it all, etc. It’s good and right to feel sad about this from time to time. Consider the alternative: you don’t get everything you wanted in life, your responsibilities become more restrictive, you grow older and less capable, and you refuse to think about any of this. What might that do to your mood? To your spirit?

Do it all again

What’ll I do next, now that I’ve faced down my indefinite optimisms and grounded them in real decisions and actions? I’ll keep the list, and keep adding to it. Why would this be a one-time thing? I haven’t changed; I know I’m going to keep finding crazy incredible things to vaguely hope for—maybe because I’m an American, or maybe because the world really is full of cool things and it’s a great time to be alive. The optimism stays, and the definition will come in due time.