20 Questions — The Ultimate Guide to Making Choices

A COMPLETE Decision-Making Checklist

On May 4, 1886, an unidentified man ignited a stick of dynamite. He was somewhere in the middle of a crowd in Haymarket Square, Chicago. The incident, which took several lives, became known as the Haymarket Massacre.

The Haymarket Massacre. Source: https://blog.newspapers.com/haymarket-riot-may-4-1886/

1. Are you in the right frame of mind to make a decision?

If you’ve ever bought a car, a salesman has probably told you “there’s a lot of interest in this car. If you don’t buy it now, it may be gone tomorrow.”

When possible, you should wait to make a decision if:

  • You feel sleep-deprived, hungry, intoxicated, or impaired in some way.
  • You’re experiencing temporary high stress or anxiety — especially if it’s caused by the people or environment around you.
  • You are being pressured by someone, especially if that person benefits from your decision.
  • You are under an artificial time-constraint.


  • Decisions often feel different in the morning than in the evening. Many people feel more rational in the morning. Sometimes, “sleep on it” is the best advice.
  • Is a decision making you feel chronic anxiety? Schedule a time on your calendar to worry about it.

2. Are you able to delete any choices based on these practical considerations?

Here’s a simple checklist before we go further. It may be all you need.

  • Are all my options affordable? Though there are exceptions, such as medical expenses, if you can’t afford something, you shouldn’t buy it.
  • Do I have the time and resources for all my options? Many decisions, like choosing to go back to school or joining a gym, come with a time commitment attached. Plus you’ll need books or equipment.
  • Do any of these choices require me to compromise a personal value or put a more important goal at risk? If a choice puts something more important to you, like your health or your family at risk, that’s usually a good enough reason to skip it.
  • Is there an ROI for each option? We sometimes agonize over decisions that don’t have an upside either way. (When I was 12, my mom asked me what color I wanted to paint my room. After a lot of color swatches I picked green at random.) If there’s little-to-no Return on Investment for a choice, that usually a good reason to give it a miss.

3. Are you agonizing over a decision that doesn’t matter?

Have you ever spent an hour comparing products on Amazon or scrolling through Netflix deciding what to watch? Have you agonized over what to order at a restaurant?


If you’re indecisive or you struggle to make low-stakes or no-stakes decisions, here’s a good rule of thumb:

4. Are you letting logical fallacies dictate your feelings?

Imagine you’re planning to buy a new computer. Before you buy it, you see a keyboard for a Windows PC and you buy it for $20. While shopping for computers later on, you realize you want a Mac. But, you can’t return the $20 Windows PC keyboard. What do you do?

5. Are you doing limited basic research?

It’s surprising how often this one falls through the cracks. For any decision you have to make, there is probably someone who has had to make a similar decision before you. Someone has written about it online.

  • Considering a move to a new city? Someone else has probably asked about that city online.

6. Are you already more informed than you think you are?

How much does my computer’s graphics card weigh? Should I buy 5 cats tomorrow? How many hotdogs are in my freezer?


Some decisions are “peace of mind” decisions. These include choices like whether to buy flood insurance, or whether to stop for gas when you can probably make it all the way home. You probably already know yourself well enough to answer: is this going to keep stressing me out? If you know you can afford it and you know it’s going to stress you out, the peace of mind is probably worth the small expense.

7. Are you judging past decisions too harshly?

Annie Duke is a champion women’s poker player. For years, she made more money than any other woman in the sport. In her new book, How to Decide, Simple Tools for Better Decision-Making, she warns users about “resulting.”

8. Are you letting F.O.s make your decision more difficult?

Patrick McGinnis invented the word “FOMO.” In his excellent book Fear of Missing Out: Practical Decision-Making in a World of Overwhelming Choice, he warns readers about two irrational fears. These fears can make simple decisions feel much more complex.

  • FOBO (Fear of a Better Option) is the bad side of FOMO. It causes us to second-guess good options. It’s what keeps us scrolling through Netflix when we’ve already found a few movies we’ll enjoy.
  • FOBRA (Fear of Buyer’s Remorse Afterwards) or (Fear of a Bad Result Afterwards) is another version of FOFGA. We experience it when we engage in two much resulting-style thinking.

9. Are you counting forwards or backwards?

You move to a new town. Exhausted after a day of unpacking, you head to the nearest restaurant. There’s no way you’re cooking tonight. Besides, the dishes are still in a box somewhere.

10. Are you letting other people make the decision harder?

When we’re feeling indecisive, we tend to gather lots of opinions. We ask our significant others, friends, or family, “what should I do?”

Follow these 3 steps to find out:

  1. Is “the crowd” like you? You have unique, personal goals and values. Some activities energize you. Some things get you out of bed in the morning. Some activities put you in a flow state. Knowing these details about yourself will help you in all areas of decision-making. They can help you avoid following the wrong crowd.
  2. Are you asking for data or opinions? Advice often won’t help you — unless it comes from someone who knows you well and has been in your specific situation. Real data will help you much more. For example, when you’re interviewing for a job, ask about the real turnover rate for your role. What percent of people in the role get promoted? What percent leave? Those percentages will give you far more information than asking “do you think I’ll stay at this job?”
  3. Are you being a “nice guy?” Nice guys struggle with decision-making. They know what they want to do (or what they don’t want to do) but they feel they have to do what someone else wants instead. They agonize over doing favors they don’t want to do. They agree to things and then search for ways to back out. They often do “nice” things with a secret expectation of some kind of repayment.


If you’re a “nice guy,” learn to follow this rule: always ask upfront for something in return for your time, even if it’s something small. You need to stop doing favors with hidden expectations attached. Don’t do favors as a sneaky way try to make people owe you something in return. If someone asks you to do a favor, be honest about what you need for it to be worth your time. It can be as simple as “sure I’ll help you move, but you order the pizza.”

11. Are you stuck in a false dichotomy?

A “false dichotomy” happens when you inaccurately believe you have only two choices. When we feel indecisive, we’re almost always trapped in a false dichotomy of some kind. Often, this false dichotomy comes from external sources — usually people who don’t want us to think outside the box.

  1. “What if I didn’t choose either option?” What if you didn’t take either job or any job at all? What if you went back to school? Would it be so bad to take a sabbatical?
  2. How can I make this decision reversible? Is there a way to test either option before committing? Let’s say you’re about to start a job in a new state, but you’re not sure you’ll like it. Don’t buy a house yet. Rent for now. Commit to checking back in after 3 months. You can decide if you want to stay then.


Whenever you find yourself asking, “What should I do?” Replace it with, “What could I do?”

12. Are you asking for what you want?

I’m consistently surprised by how often this works. Ask for what you want. It’s simple and effective, yet we often avoid it.

13. Are you comfortable with endings?

Flappy Bird was a mobile game that became so popular, its creator shut it down. That might sound counter-intuitive. Every day, the game made its creator $50,000. Why shut down something so successful?

14. Are you letting imaginary data scare you?

If you’re struggling with a big decision, you’re probably playing the “what if?” game. You’re playing out all sorts of scenarios in your head. You’re feeling stress about things that haven’t happened and probably never will. You’re playing a game of chess against the future, trying to anticipate its moves.

  • Do I have any real, specific, stand-up-in-court evidence that any of these “what if” scenarios will happen?
  • Can I tie any real probabilities to the scenarios I’m imagining? Am I worried about something with a 1% chance of happening?
  • Do you know what success and failure look like? Using as much real data as possible can I picture a realistic worst and best case scenario for each outcome? Could I accept those outcomes?


Many people find it helpful to think in bets. It can help to ask “how much money would I be willing to bet on this outcome?

15. Are you just getting cold feet?

Have you made a decision, only to get cold feet? Are you second-guessing your choices as a deadline nears?

  • Have you come into new information. Do you have some new, hard data that renders your previous reasoning obsolete?
  • Has your situation or emotional state changed since you made the decision? For example, did you make a decision while under pressure from a salesperson?
  • Does your choice put you or someone you care about at risk of serious physical or financial harm?
  • Do you frequently get cold feet and then later realize everything was fine?
  • Are you feeling cold feet just because it’s a big decision and you naturally feel emotional around big decisions?

16. Are you able to tolerate “meh” results?

You’ve probably heard the statistic — that nearly 100 percent of drivers think they’re better than average. You’ve probably also heard the claim that money doesn’t buy happiness. Once you have enough money to comfortably pursue what’s important to you, additional income doesn’t appear to make you happier.

What is your tolerance for getting ripped off?

It can’t be zero. This is one of the most important rules for successful investing. Whether you’re putting money in the stock market, starting a business, or buying real estate, some of your money will get lost to high fees, unexpected downturns, bad hires, and more.


Fill in the blank: “I can never be certain that…” Say it out loud. Acknowledge to the world and to yourself that there is no guaranteed right answer. Absolve yourself of responsibility to be perfect, and embrace the thrill and adventure of life.

17. Are you able to calculate chance or expected utility?

Sometimes, math makes life easier. You can outsource many decisions to a calculator. Imagine this scenario:

  • Divide 120 dollars by 6, you get 20 dollars: the expected utility for Option 2.


Sometimes, to make a decision, all you need to do is calculate the odds. By applying math, you can get out of the emotional headspace that might be making your decision harder.

18. Are you focused on details that don’t matter?

In 1973, Paul Slovic tested a theory. He gave professional horse racing experts a few pieces of data and asked them to predict the outcome of a horse race. Then he gave them a few more pieces. Then a few more.

“Yes, which college you choose probably matters a lot, but once you’ve put a certain amount of time into selecting a school, there are diminishing returns on putting in more effort. If two options seem equal, they probably are.” — Jonathan Bales

I know exactly what he means. I agonized over my college applications. I might have read every single review of every single college I could get into. To this day, I have no idea if I made the right decision. My decision turned out ok, and I probably would have been as happy no matter where I went to school as long as it fulfilled my basic criteria.

How can I make this decision with the least information possible?

Way back in 1957, the psychologist Herbert Simon discovered the key to decision-making bliss. He suggested that decision-makers should aim to “satisfice” rather than “maximize.” Decide on your absolute must-haves, and go with whatever option best fulfills those.


Sometimes, it helps to see your problems from a third-party view. Imagine that someone else has to make the choice instead of you. What would you tell them to do?

19. Are you being true to you?

The Subtle Art of Not Giving a F*ck by Mark Manson is a surprisingly good book — especially if you’re indecisive. One of Mark’s insights is this:

“The solution to one problem is merely the creation of the next one.”

Every solution to a problem leads to new problems. Whatever job you take, house you buy, city you move to, or person you marry (or don’t) will be imperfect. Each will come with their own unique problems.

12. Are you learning from every decision?

The first few steps in this decision-making process are about vetting your decisions. You want to make sure that you’re asking the right questions, and that your decision is worth consideration in the first place.

  • What didn’t I worry about that did end up mattering?
  • Can I set some ground rules in the future, so that I’m prepared next time I have to make a decision like this one?
  • If I had to give someone a rule of thumb for making this kind of decision, what would it be?

Are you seeing a pattern yet?

In her most famous work, The Bell Jar, the poet Sylvia Plath wrote these haunting lines:

I interview startup gurus and recently founded my own business, Wrenworks — helping startups launch MVPs.

I interview startup gurus and recently founded my own business, Wrenworks — helping startups launch MVPs.