How to make hard decisions

Decision-making is easy. In most cases, we already know what to do. And then we spend weeks, convincing ourselves it’s the best option. Sometimes, we never get to make the call.

Why are we doing this to ourselves?

First, because we expect serious decision-making to be really hard. Maybe we even want it to be hard. Because if we spend weeks instead of minutes on deciding and fuck it up anyways, we’ll have a sound excuse for ourselves — “But I tried my best!”
Second, we always try to come up with the very best option. Because the stakes are damn high. This is a straight path to a weird world called Analysis-Paralysis, where we get stuck for ages.

This year, I’ve made more tough decisions than ever in my life. I decided to shut down the startup we were working on, fly to China to study Shaolin Kung-Fu, and pass on a dream job offer to start a new venture and move to London.

And I would never have made them without thought experiments.

What are thought experiments

In its simplest, thought experiments are questions. Very well-structured hypothetical questions that employ our subjunctive reasoning, like “What might happen if...?”

By using these hypothetical questions, we get two things:

We gain new information. Just by looking at already known empirical data from a different and unusual perspective, we can draw new (a priori) inferences for our decision.
We invoke intuition. This is more important and less obvious. For many decisions, we already know the right answer. It just feels right. We need the guts to make the call.

To improve my decision-making, I’ve carefully explored and tested hundreds of thought experiments. To save you months on doing the same, I’ve collected the best nine in this post. They come from brilliant people, whom I credit gratefully for their work.

Please don’t think about these experiments as a checklist to go through when making a decision. Think for yourself which one might be a good fit and apply it wisely.

1. The Simulation, by Tim Urban

This is my favorite thought experiment (and most powerful).

Here’s how Tim describes it:

If someone gave you a perfect simulation of today’s world to play in and told you that it’s all fake with no actual consequences—with the only rules being that you can’t break the law or harm anyone, and you still have to make sure to support your and your family’s basic needs — what would you do?

It works is by removing risk from the equation — if I have one more life anyway, why not try this crazy thing? It took me a few weeks to realize how deep is the thought behind it: there’s no difference whatsoever between the simulation and real life.

Once you accept that truth, your most risky desires start popping up.

2. The Movie Guy, by Joe Rogan

Here’s how Joe describes it:

Live your life like you’re the hero in your movie. And right now is when the fucking movie starts and your life is a shit bag disaster. Pretend you are, right now, you’re in the part of the movie that starts and it shows you as a fucking loser. And just decide not to be a loser.

Live your life like this is a documentary crew following you around, analyzing you. Do what you want to do so your kids one day will look back at it and see that documentary and look on it with pride, like, wow, my dad was a bad motherfucker, he really did what he had to do. Wow, my mom really got her shit together.

I’d love a success story, but even more than a success story I like a dude who fucks his life up and then gets it back together again story; those are my favorite stories. And the way to do that — you gotta write shit down, you gotta think that you are the hero in your own fucking movie, and then you gotta sit down, and you gotta write shit down. Write down what you need to do.

The question:

What would the movie guy do? – Joe Rogan

3. The Deathbed Me, by Tim Urban

Here’s how Tim describes it:

The deathbed test is casting yourself into the distant future, imagining yourself lying on your deathbed and asking what your future self would want you to do at the current juncture of your life.

To stay on the 'default' path you’re travelling now – complete with its comfort, certainty, status and security – or to take the road less travelled? To go with the convenient 'less hassle' option, or to dig deep and to veer onto a path that tugs at your heart, despite the comforts you have to give up in the process?

Let’s face it, there will always be many reasons to justify taking the easier path, sticking with the status quo and avoiding the possibility of failure. Yet the longer I am alive, the more firmly I believe that living a life that nurtures our souls, and not just a short-term sense of comfort or security or status, will often require trading comfort for inconvenience, security for uncertainty, and going that extra mile (or 10,000!) when you can easily justify not bothering.

So what about you? As you think about the big decisions in your career and life, and perhaps a few of the smaller ones, are you currently on a path that puts you at risk of one day looking back and wondering, perhaps regretfully, ‘What if I’d tried?’

The question:

Am I currently on a path that puts me at risk of one day looking back and wondering, perhaps regretfully, “what if I’d tried?” – Tim Urban

4. The Regret Minimization Framework, by Jeff Bezos

Here’s how Jeff describes it:

The framework I found, which made the decision incredibly easy, was what I called — which only a nerd would call — a “regret minimization framework.” So I wanted to project myself forward to age 80 and say, “Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have.”

I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision.

And I think that’s a very good if you can project yourself out to age 80 and think, “What will I think at that time?” it gets you away from some of the daily pieces of confusion. You know, I left this Wall Street firm in the middle of the year. When you do that, you walk away from your annual bonus and that’s the kind of thing where there short-term can confuse you but if you think about the long-term then you can really make good life decisions that you won’t regret later.

Sam Altman also adds on this:

If you think you’re going to regret not doing something, you should probably do it. Regret is the worst, and most people regret far more things they didn’t do than things they did do. When in doubt, kiss the boy/girl.

Gary Vee also adds on this:

What kids struggle with is the decision they want to do versus the decision that they think they’re supposed to do based on the other voices. Nobody old and about to die talks about what they did. They talk about what they didn’t do. Don’t not do what you wanna do.

The question:

At the age of 80, will I regret not doing this? – Jeff Bezos

5. Fear-Setting, by Tim Ferris

Here’s how Tim describes it:

I do an exercise called “fear-setting” at least once a quarter, often once a month. It is the most powerful exercise I do. Fear-setting has produced my biggest business and personal successes, as well as repeatedly helped me to avoid catastrophic mistakes.

If you are nervous about making the jump or simply putting it off out of fear of the unknown, here is your antidote. Write down your answers, and keep in mind that thinking a lot will not prove as fruitful or as prolific as simply brain vomiting on the page. Write and do not edit—aim for volume. Spend a few minutes on each answer.

Define your nightmare, the absolute worst that could happen if you did what you are considering. What doubt, fears, and “what-ifs” pop up as you consider the big changes you can—or need—to make? Envision them in painstaking detail. Would it be the end of your life? What would be the permanent impact, if any, on a scale of 1–10? Are these things really permanent? How likely do you think it is that they would actually happen?
What steps could you take to repair the damage or get things back on the upswing, even if temporarily? Chances are, it’s easier than you imagine. How could you get things back under control?
What are the outcomes or benefits, both temporary and permanent, of more probable scenarios? Now that you’ve defined the nightmare, what are the more probable or definite positive outcomes, whether internal (confidence, self-esteem, etc.) or external? What would the impact of these more likely outcomes be on a scale of 1–10? How likely is it that you could produce at least a moderately good outcome? Have less intelligent people done this before and pulled it off?
If you were fired from your job today, what would you do to get things under financial control? Imagine this scenario and run through questions 1–3 above. If you quit your job to test other options, how could you later get back on the same career track if you absolutely had to?
What are you putting off out of fear? Usually, what we most fear doing is what we most need to do. That phone call, that conversation, whatever the action might be—it is fear of unknown outcomes that prevents us from doing what we need to do. Define the worst case, accept it, and do it. I’ll repeat something you might consider tattooing on your forehead: What we fear doing most is usually what we most need to do. As I have heard said, a person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have. Resolve to do one thing every day that you fear. I got into this habit by attempting to contact celebrities and famous business people for advice.
What is it costing you—financially, emotionally, and physically—to postpone action? Don’t only evaluate the potential downside of action. It is equally important to measure the atrocious cost of inaction. If you don’t pursue those things that excite you, where will you be in one year, five years, and ten years? How will you feel having allowed circumstance to impose itself upon you and having allowed ten more years of your finite life to pass doing what you know will not fulfill you? If you telescope out 10 years and know with 100% certainty that it is a path of disappointment and regret, and if we define risk as “the likelihood of an irreversible negative outcome,” inaction is the greatest risk of all.
What are you waiting for? If you cannot answer this without resorting to the previously rejected concept of good timing, the answer is simple: You’re afraid, just like the rest of the world. Measure the cost of inaction, realize the unlikelihood and repairability of most missteps, and develop the most important habit of those who excel and enjoy doing so: action.

Here’s a step-by-step guide I wrote for doing fear-setting.

The question:

What if I..? – Tim Ferris

6. New Homunculus, by Nate Soares

Here’s how Nate describes it:

When you're feeling guilty, it is sometimes helpful to close your eyes for a moment, re-open them, and pretend that you're a new homunculus (a little person in your head that can move your hands and shape your mouth and that decides where to steer the body and so on).

Close your eyes, and pretend you're arriving in this body for the very first time. Open them and do some original seeing on this person you now are. Rub your hands together, look around, and take stock of your surroundings. Do some internal checks to figure out what this body values, to figure out what it is you're fighting for. Check the catalog of plans and upcoming actions. Check the backlog of memories and obligations.

There will probably be some housecleaning to do: homunculi are known to get a little careless as they age, and the old homunculus that you replaced probably let a bunch of useless tasks accumulate without realizing it. As a new homunculus you have the privilege of pruning the things that obviously need pruning. Maybe you'll look and say "Ah, yes, we're going to cancel lunch with that person; this body was secretly dreading it. I also see that this body is currently spending a lot of cycles feeling guilty about a date that went poorly last week; we can dismiss that, it's no longer useful for this homunculus. And also, "exercise" doesn't seem to be on today's schedule at all! How strange. This body definitely intended to exercise today; somehow it fell off the list. I'll put it back on."

It can be quite liberating to be a new homunculus, without any obligation to propagate the errors of the old one. This is, in fact, a common technique for dealing with the sunk cost fallacy (also known as the "pretend you're a teleporting alien that just teleported into your body" technique). This is useful for avoiding sunk costs because the new homunculus has no reason to honor the old homunculus' sunk costs.

Say the old homunculus bought plane tickets which would let you travel to Texas tomorrow (and return in a week), and that the ticket is non-refundable. The old homunculus may well have an attachment to the "go to Texas" plan, and may try to convince themselves to go even when it becomes clear that the trip won't be worth the time. The new homunculus, however, has no such loyalty to the sunk costs: it can just evaluate whether or not to go on the trip regardless of how much the tickets costed.

The question:

What would the new homunculus do?— Nate Soares

7. The Last Day, by Steve Jobs

Here’s how Steve described it:

When I was 17, I read a quote that went something like: “If you live each day as if it was your last, someday you’ll most certainly be right.” It made an impression on me, and since then, for the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure — these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.

The question:

If today were the last day of my life, would I want to do what I am about to do today?— Steve Jobs

8. The Big Green Button, by Tim Urban

Here’s how Tim describes it:

Some of the most telling thought experiments help hear what the gut’s saying by trying to remove the often deafening voice of fear from the question and seeing if that changes anything.

For example, to test whether a resistance to breaking up is just a dread of the actual breakup itself, you could ask: “If there were a big green button in front of me that, if pressed, would make me fully single, where everything has been worked out with getting our things from each other’s apartments, where everyone in my life already knows, and where I’m totally emotionally recovered and moving on—in fact, I have a date tonight—would I press the button?”

Or if the real fear is of being single for years and years and never finding a new relationship, the button could do all of those things but also include “and I’m immersed in a new relationship.”

The question:

Would I press the button? – Tim Urban

9. The Envelope, by Tim Urban

Here’s how Tim describes it:

Imagine you were being arranged married by the town matchmaker and she handed you an envelope with your to-be spouse’s name written inside. You open the envelope and it’s the name of your current partner.

This image might just make your gut jump up for a second and say, “Phew!” Or maybe instead, it would deflate just a little, just for a moment. If either happens, that’s good information.

Tim came up with this thought experiment for making relationship decisions, but I think it applies to many other hard choices as well. Just replace the content of the envelope with your subject and imagine that there's some town wizard who decides stuff for you and you have no control whatsoever.

The one thing that really helped me was to make this experience as realistic as possible. I tore up a sheet of paper into pieces and wrote down a separate option on each of them. Then I shuffled them, selected one randomly, put it into the envelope, taped & sealed it, and imagined the whole thing how the town wizard is passing me over this envelope. I have no other options besides opening it and accepting the choice. It worked like magic; my intuition was like — "Hell no!”

Principles

Finally, here are some principles for decision-making that I found to be useful:

Check for good conditions for decision-making, both physical and mental. Examples: not tired, not sleep-deprived, not hungry, calm, not unhappy, or worried about something, not on the go, no need to rush.
Spend time describing the problem before you spend time describing possible solutions.
Check for biases (i.e., sunk cost, confirmation biases).

Ask yourself: What obvious things a reasonable person would do before making this sort of decision?

Would they spend a full five minutes (by the clock) brainstorming alternative options before settling on a decision?
Would they consult with friends and advisors?
Would they do some particular type of research?
Ask yourself: What's the best action I can find in the next five minutes? This has proven to be extremely efficient. More than 50% of my final decisions were these initial ideas drafted in under 5 mins timer.
Check if your options have components that might distort your thinking; break them down by removing one element at a time. Example: if the decision has the potential to impact your income significantly, then imagine you have full financial freedom and ask, "Would I still be interested in this?" The goal is not to ditch away money, but to identify what's pulling you back.
"Often any decision, even the wrong decision is better than no decision." — Ben Horowitz
"Would I still be interested in learning this thing if I couldn't ever tell anybody about it? That's how I know it's real. That's how I know it's something I actually want to know." — Naval. This is a great tip for removing fame / social acceptance out of the equation.
"If you have more than one reason to do something (choose a doctor or veterinarian, hire a gardener or an employee, marry a person, go on a trip), just don't do it. It does not mean that one reason is better than two, just that by invoking more than one reason you are trying to convince yourself to do something. Obvious decisions (robust to error) require no more than a single reason." — Nassim Taleb
"I don't believe that I have the ability to say what is going to work. Rather, what I try to do is I try to eliminate what's not going to work. I think being successful is just about not making mistakes. It's not about having correct judgment. It's about avoiding the incorrect judgments." — Naval
"If you're not saying "HELL YEAH!" about something, say "no"." — Derek Sivers
"If two equally difficult paths, choose the one more painful in the short term (pain avoidance is creating an illusion of equality)." — Naval
"Live the life you want other people to live." — Naval
"If you can't decide, the answer is no." — Naval

I’ll leave you with this quote from Jerzy Gregorek:

Easy choices – hard life. Hard choices – Easy life. – Jerzy Gregorek

Thank you very much for reading my work.