20 Questions — The Ultimate Guide to Making Choices

A COMPLETE Decision-Making Checklist

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.

A century later, psychologist Daniel Gilbert drew on the incident in the introduction to his book Stumbling on Happiness. In the book, Gilbert tells the story of the Haymarket Martyr — an innocent man who was falsely charged and executed for causing the explosion.

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

You might assume the Haymarket Martyr was pretty unhappy about the whole situation. But according to Gilbert, the innocent man was happy with his unjust sentence. He believed that his death would bring about important changes in society.

Meanwhile, people all over the world, in seemingly far better circumstances than the Haymarket Martyr, are often depressed and unhappy. It’s no secret that many famous and wealthy people are miserable — even lottery winners.

How is it that martyrs can be happy and millionaires unhappy? Gilbert argues that as human beings, we are hard-wired to fail at predicting the circumstances and choices in life that will make us happy.

If Gilbert is right, how can we make good decisions?

This research-based, 20-step exercise will teach you to make decisions quickly and confidently. If you apply this process to a few real-life decisions, you’ll become more decisive. You’ll be able to make decisions faster and be happier with the outcomes. And (good news!) you won’t have to face an 18th-century justice system to do it.

Don’t just read this. Save it. Come back to it when you have a difficult decision to make. This is a long post. I used to be a really indecisive person, so I’ve put a lot of time and thought into this. I’m going to cover a bunch of books, studies, and theories. It’s long, but it will give you everything you need to make decisions quickly, confidently, and without regret.

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.”

He knows the car will still be there tomorrow, and there are others like it. But, you’re sitting in his office, and he’s bombarding you with sales tactics. He’s telling you he can give you a special price, but only today.

Stressful situations like this make you less rational but more anxious. If possible, take yourself out of the stressful situation. Tell the salesperson you’re going to grab lunch, and you’ll be back in the afternoon.

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.

Tips:

  • 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 realistic? Are there any choices I should remove from consideration because they are not actually achievable? (One of my favorite examples of this question is the mid-life crisis. Sorry, but you can’t be 20 years old again, even if you move out, shack up with your secretary, and buy a Porsche.)
  • 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?

We sometimes devote more effort to small decisions than big ones. Small decisions feel in our control. We feel like we should get them right. But big decisions can feel overwhelming. Sometimes, we make big decisions quickly to get them off our plates.

99% percent of all our decisions are low-stakes or no-stakes. The phone we buy, the movie we watch, or the dinner we order tonight won’t matter a few weeks from now. Even if they do matter a bit, like buying a phone, they’re reversible: you can return the phone.

Tip:

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

Go with whatever you liked first. Sometimes your unconscious brain knows things you don’t. If something on the menu jumped out at you right away, order that — even if you spot something else a second later that might be better.

This theory has been tested on exam-takers. When you’re not sure about an exam question, resist the urge to change your answer at the last minute unless you have a good reason.

No matter what you choose, your “decision is basically a coin-flip,” says Lucky Maverick Jonathan Bales. Agonizing over low-stakes decisions isn’t worth the stress. Life is too unpredictable. No matter what you order at the restaurant, it might arrive overdone, underdone, or get dropped on the floor in the kitchen and you’ll never even know. (Source: I worked at a restaurant in high school.)

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?

If you feel pressured to buy a Windows PC because you already bought a Windows keyboard, you’re suffering from sunk cost fallacy. The $20 is gone no matter which computer you buy. There’s no reason to saddle yourself with an expensive computer you don’t want for years to come.

Several other logical fallacies can make simple decisions feel difficult. If you’re not familiar with them, take some time to read up on the big ones and how they can impact your decision-making process.

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.

  • Buying a house? Search for a checklist of things to look out for.
  • Considering a move to a new city? Someone else has probably asked about that city online.

Don’t go overboard. For most decisions, like what to order at a restaurant, research is unnecessary. The purpose of doing research is to do your due diligence. You shouldn’t make a big decision like buying a house without doing research.

Warning!

Many people get stuck in the research phase of making a decision. Avoid the temptation to search endlessly for a hidden flaw you haven’t discovered yet. Don’t live in fear that you’ll make a choice, only to have something go wrong that you should have planned for.

Everyone has “why didn’t I think of that!?” moments. They’ll happen no matter how much research you do. Yes, you should do basic research for big decisions. But, past a certain point, you’re not going to dig up some magical piece of new information that changes everything.

The right amount of research should make you feel confident — not overwhelmed. Set a limit on the amount of research you’ll do. Even for big decisions, 5–10 articles or checklists are plenty. Especially if you start to feel as though you have too much information, it’s time to stop researching.

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?

If you were to guess the answers to these questions, you might guess something like: “1 pound,” “no,” and “12.”

We’ve never met. You haven’t done research into any of these topics. But all of your answers are nearly spot on.

Believe it or not, for most decisions, you already have most of the information you need. You are never making a decision in a total information vacuum. You know a lot about yourself what you care about. You know a lot about the world. This knowledge is often more important than the small details you’ll find online.

In other words, you can trust your instincts more than you think you can.

One way to think about this concept is called Recognition-Primed Decision-Making. Developed by firefighters, who have to make decisions rapidly with limited data, RPD relies on pattern recognition. Even though the exact circumstances of every decision may be different, patterns or similarities to previous decisions emerge when we look closely.

For example, when you buy a house for the first time, you’ll also have to decide what home-owner’s insurance coverage to get. You’ve never purchased homeowner’s insurance coverage before, but maybe you have purchased car insurance before. You can draw on your experience with car insurance to estimate what deductible you’ll be comfortable with and more.

Even if you don’t own a car, you could still apply this principle by considering other times you have had to insure yourself against future risks.

Tip:

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.”

“Resulting” is what we do when we judge our decision-making strategies based on a decision’s outcomes. When we make a risky bet and it wins, we congratulate ourselves on our boldness. If the same risky bet had happened to lose to a player with a better hand, we’d regret our foolishness.

Resulting: the same decision, evaluated two different ways based on luck.

Resulting is a combination of logical fallacies. It makes us poorer decision-makers because it prevents us from learning from our decisions. Getting something wrong when you couldn’t have predicted the outcome wasn’t a mistake. Past “right” decisions don’t always mean they were good decision-making processes.

Don’t feel bad, stupid, or guilty about a decision that didn’t work out in the past. It’s difficult to be decisive when we live in fear of the guilt we’ll feel for a poor outcome. Anxiety is largely a waste of time.

“Adulthood,” someone once said on the internet, “is like looking both ways before you cross the street — and then getting hit by an airplane.”

Life is so strange and unpredictable that our worries are often misplaced. It’s not that bad things don’t happen — they do. It’s that there’s much less point in worrying about them than we think. Nearly all of the misfortunes I’ve suffered have been unexpected. Meanwhile, the things I’ve worried about the most have never happened.

This has been the case so often in my life that I have started to use it as a rule: the more worried I am about an outcome, the less likely it is to happen. It’s a self-fulfilling prophesy. I take steps to avoid the things I’m worried about, and I worry about the things I’ve taken steps to avoid. If something is going to go wrong, it is likely to be something I couldn’t possibly have predicted, so there’s no point in beating myself up too much.

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.

  • FOMO (Fear of Missing Out) can push us outside of our comfort zones. But, it can also create a lot of stress.
  • 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.

I want to add two more fears to the list:

  • FOFGA (Fear of Feeling Guilty Afterwards) is the cause of a lot of stress. We don’t want to decide until we have some sort of barrier against guilt. We seek something we can point to if things go wrong as proof that we tried our best.
  • 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.

When you struggle to make a choice, or you feel unhappy with past choices, be sure you’re not just feeling irrational F.O.s.

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.

You find a restaurant, and the food is good. It’s really good. It’s so good, you eat there nearly every time you go out.

A few years later, you get a new job. You have to move again. You pack your dishes up. You head to your favorite restaurant for one last meal. It’s closed. For the first time, you go somewhere else.

The food at this new restaurant is amazing. It’s way better than the place you’ve been going to for years. You’ve been eating at the wrong restaurant this entire time! It’s too bad you’re moving out of town.

In decision-making, time matters. When you have a lot of time (or a lot of room for mistakes) you should experiment. You should take risks. When you have less room for error, you should be more cautious. It’s why your 401k shifts more money from stocks towards bonds each year.

Imagine you’re in a relationship that feels just OK. It’s tolerable, but mediocre. The person you’re dating is great, but not perfect. You’re feeling FOBO and want to play the field. You agonize over whether to stay in the relationship and try to improve it, or break up.

If you’re in high-school or college, the answer is: break up. You’ll have years to meet new people. Your tastes and personality will change. If you’re already unhappy with the relationship, you’ll be really unhappy with it in ten years.

But, if you’re in your 40s, you’re in a different situation. You should probably work on improving the relationship rather than walking away. The hard truth is that you no longer have as much time to play the field, and you’re options will be fewer.

The important thing is that you count forward, not backwards. You should not fall into “sunk cost” thinking. Even if you’ve been dating all through college, that doesn’t mean you have to stay together.

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?”

What are other people doing? What do other people recommend? Asking around seems like the right thing to do. We think that if we let other people tell us what to do, we can take care of that FOFGA and FOBRA.

We imagine we’ll feel better about our choices if we know that we can blame a bad outcome on somebody else. Nobody can blame us for our mistakes if we are doing what everybody else did.

There are even some pretty good data to suggest that a herd mentality might be just what you need. In The Wisdom of Crowds, NY Times Business writer James Surowiecki argues that large groups can be smarter than individual experts.

Instead of making us feel more confident, all the advice sometimes makes us feel more overwhelmed. We feel pressured to follow the advice, even if we don’t agree with it. We follow the herd, even though we don’t like where they’re going.

So when should we follow the crowd, and when should we strike out on our own?

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.

Tip:

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.

We’re at our most indecisive when we believe we have two or three options and only those options. Often, we attempt the impossible task of mentally forecasting the outcome of each decision. Then we try to compare the imagined outcomes of each choice. We feel anxious because we can’t predict the future. Often, both options seem too equal, or too unpredictable.

If you feel trapped between two or more equally appealing (or equally unpredictable) options, ask yourself these questions:

  1. “What could I change about either option that would make this a way easier decision?” For example, if you’re comparing two job offers, could you negotiate for better benefits, a higher salary, or extra time off at one of them?
  2. “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?
  3. 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.

Tip:

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.

Are you unsure whether you’re getting paid fairly? You might be surprised to find that your coworkers are totally willing to discuss their salaries — especially if you return the favor.

Indecisive people have a strange, emotional aversion to asking for what they want. Maybe you’re worried about offending people. Maybe you’re worried about exposing a weakness, as if you don’t want to admit how little you know. Whatever your reasons, you may be surprised what happens when you ask.

If you’re struggling to make a decision because of too many unknowns, you may have fallen into this trap. There may well be someone you can simply ask for help.

I don’t mean that you should ask a friend for advice. Instead, I mean that you should call in the experts and ask for raw data. Sometimes, you can even ask a perceived enemy for information. You might find common ground.

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?

The answer: the game was addictive. People who started playing couldn’t stop playing. They dedicated thousands of dollars and hours of their lives to playing it. To the game’s creators, Flappy Bird was so addictive it felt immoral to keep selling it.

One of the features that made Flappy Bird so addictive was its lack of endings. When players lost, the game instantly restarted. The game was designed so that players never had an opportunity to put it down and move on. It capitalized on a weird quirk of human beings. We hate endings.

We hate endings so much, we stick in jobs and relationships that make us miserable. Every time I’ve quit a job, I’ve felt a twinge of sadness or panic as I walked out of the building on my last day — even if I was moving on to a much better job.

Flappy Birds are everywhere. Everyone has Flappy Birds in their lives. We all have endings we avoid. Most decisions, especially big life decisions, are Flappy Birds. When we make a big choice, there’s something that has to end. As the saying goes: a door has to close so that another may open.

To become better decision-makers, we must get over our fear of endings. We need to recognize that endings are not all bad. Endings are a necessary and valuable part of life. They are inherent to advancement.

Every time you get promoted, one job ends and newer, better-paying one begins. To find a great relationship, you probably have to break up with a few losers.

Learn to seek out endings. Like in video games, endings are often a sign that you are on the right track. If you’re not leveling up, you’re probably losing the game.

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.

The “what if” game is often accompanied by wishful thinking. You’re not just thinking about all the hypothetical bad things that might happen if you make the wrong decision. You’re also imagining all the things that could go right if you make the right decision. You’re scared that if you make the wrong decision, you might miss out on something great.

Imaginary data can over-complicate any decision. If you’re playing the “what if” game, try asking these questions instead. You might be surprised how many of these practical questions you’ve forgotten to ask:

  • What do I know for sure about this person, place, company, etc?
  • 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?

Tip:

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?

It’s normal to get cold feet. In fact, it’s a sign of a healthy, functioning mind. Congratulations, you’re a human with human emotions and critical thinking skills.

Here are some questions to ask before you let cold feet convince you to run for the hills.

  • Did your actual, material situation change? Has a significant event occurred that changes everything?
  • 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?

If that’s true, you might want to redo your decision-making process. But, here are some situations where you can feel safe to ignore your cold feet.

  • Are you engaging in logical fallacies, what-if scenarios, or any of the other irrational types of reasoning we discussed?
  • 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?

If you had good reasons to make a decision, and none of the facts have changed, don’t let cold feet change your mind.

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.

Fortune and tragedy, it turns out, do not impact happiness nearly as much as we generally assume. We human beings are terrible at estimating what will make us happy, and what decisions we will regret. We don’t know ourselves as well as we think we do.

People who lose limbs, experience earthquakes, and even go blind often report similar overall levels of happiness in the years after the traumatic events to the years before. The reason for this strange phenomenon is known as the “hedonic treadmill.”

The Hedonic Treadmill works like this: no matter what happens in our lives, after a short time, we almost always return to a baseline level of happiness. If you are a generally unhappy person, a single choice or event (like buying a new phone or going on vacation) won’t make you happier in the long run. If you are generally happy already, a single misfortune is unlikely to change that.

In other words, a single decision, even a big one, probably won’t impact your overall happiness as much you expect it to. A wrong decision or poor choice is not likely to make you as unhappy as you fear. A right decision or good choice is unlikely to make you as happy as you hope. The most likely outcome of your decision, either way — measured in lifetime happiness — is negligible.

The result of your decision is likely to be just OK. Can you live with that?

Here’s another way to think of it:

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.

If you are unwilling to experience imperfection, disappointment, and ripoffs, you’ll never be able to make a choice again. Everything has downsides. You need to know what your tolerance for those downsides is. How much money can you afford to lose on an investment?

In any decision, you have to know your tolerance for imperfect results. Unless you’re playing Russian-Roulette, your tolerance probably isn’t zero.

A desirable outcome is still a desirable outcome even if the results aren’t perfect. If you buy something you need at a price you can afford, you still made a good choice — even if you find it on sale for cheaper two days later.

Tip:

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:

I give you two options to win money:

Option 1: I flip a coin. If it lands on heads, I give you 20 dollars.

Option 2: I roll a dice. If I roll a 6, I give you 120 dollars.

Which option do you choose? If you like math, this is a simple choice.

  • Divide 20 dollars by 2, you get 10 dollars: the expected utility for Option 1.
  • Divide 120 dollars by 6, you get 20 dollars: the expected utility for Option 2.

Option 2 is the best. Even though there’s less chance of winning money, the amount you win is high enough that it’s worth it. Your risk tolerance is also high: if you don’t win anything, you’ll be fine. You’ll have just as much money as when you started. You won’t go broke. Whether you win $120, just $20, or no money at all, your baseline level of happiness is unlikely to change.

Let me give you a harder riddle:

Your boss tells you to hire a secretary. But there’s a catch. You have to interview them one at a time, and you have to accept or reject each applicant right at the end of the interview. No re-dos. No call-backs. That means if you hire somebody, you can’t interview anyone else. If you interview every candidate, you’ll be stuck selecting the last one, whether you like them or not.

If you have 100 secretaries to choose from, how (or which) do you choose?

The Secretary Problem has many names. Sometimes, it’s called “the Marriage Problem,” “the Sultan’s Dowry,” or the “Fussy Suitor.” It’s so compelling because it mirrors many of the difficult choices we make in our lives. As its many names suggest, we don’t get to marry multiple people and then pick the best one.

While there are many proposed solutions, no strategy is guaranteed to land you the best possible secretary. The best you can do, according to mathematicians, is to interview and reject about 37% of the applicants. Then identify the best candidate you’ve interviewed so far. Let’s call her Jane. You can’t hire Jane (those are the rules) so continue to interview more candidates.

As soon as you find someone who is as good or better than Jane, hire that person. This strategy doesn’t guarantee the best possible secretary, but it gives you the best chance of getting one of the best.

Tip:

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?

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.

The results of the study were shocking. Once they had a few important pieces of information, the rest of the information didn’t matter. Experts were as accurate with seven pieces of data as they were with 20.

The only thing that changed was their confidence. The more data they had, the more likely the experts were to overestimate their chances of being right. In other words, the experts were most accurate when they focused on only a few important pieces of information.

Most decisions might as well be coin flips. It doesn’t matter which option you pick because once you’ve taken the important information into account, the odds of getting it “right” don’t change that much.

“This can be the case with small decisions, like which shoes you should wear on a date, but also with very consequential ones, like where to go to college,” says Lucky Maverick Jonathan Bales.

“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.

If anything, I focused on too many small details. I read about college cafeterias and gyms when I should have been interested in affordability and social culture.

Your job as a decision-maker is not to maximize the amount of information you have before you flip the coin. All you need to decide is:

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.

If both options fulfill your requirements well, go with the front-runner.

Look at each of your options and ask yourself “if this was the only choice I had, would I be happy with it?” If the answer is yes for both, you can go ahead and pick either one. You probably won’t get any better of an outcome by analyzing your options any further.

This isn’t just a theory. Simon tested it and found that Satisficers were indeed happier than Maximizers.

Know what’s most important to you and focus on that. As you research each option, forget any data that isn’t the most compelling. If you don’t work out that much, don’t let a nice gym factor into where you go to college.

Tip:

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.

Rather than trying to avoid these problems, you should try to steer your life towards the problems you want to solve. To be a “satisficer,” seek problems you enjoy solving. Do not seek to have no problems at all.

There’s an old piece of relationship advice that goes something like this:

You don’t want to marry someone you’ll never fight with. You want to marry someone who’s worth fighting with.

In The Subtle Art, Mark gives advice for identifying which problems you should try to solve. How do you know who is worth fighting with? He says to think about your internal values, and the metrics you measure your values by.

External values like “I want to be the most popular,” will lead to disappointment. Popularity is a goal over which you have little control. If you base your decisions on (or measure them against) this type of goal, you will never be happy with the results.

Instead, try to identify internal values, or create them if you don’t have them.

“I want to work hard so I can be a role model for my kids” is one such value. You can control how hard you work. Choosing a difficult career over an easy one may seem counter-intuitive, but if it lines up with a core, internal value, you will be happier with the results.

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.

The next step is to cut down on the amount of information making your choice more difficult. Most of it doesn’t matter, and will only confuse you further.

The final step is to take those key pieces of information and see how they line up with what is most important to you. The choice that best satisfies your fundamental needs is better than the perfect choice — because the perfect choice doesn’t exist.

Every decision is an opportunity to learn. Taking a moment to think about each decision can help you become more decisive in the future. Once you know your values, you can use them to make decisions more quickly. Each time, you’ll get faster and faster and more and more sure of yourself.

If you’re an indecisive person, consider keeping a decision journal. Record the decisions you made. Write down the options you considered. Note the people you asked for advice and what you asked them. Write down the information you found. Pay special attention to the concerns that worried you the most.

Check back in later, once you know the outcome of your decision. Then ask yourself questions like these questions:

  • What did I worry about that didn’t end up mattering that much?
  • 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 saw my life branching out before me like the green fig tree in the story. From the tip of every branch, like a fat purple fig, a wonderful future beckoned and winked. 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 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.”

Sylvia could not stand the risk of settling for an imperfect life. She did not want to choose the wrong fig. Instead, she taped up the door between her kitchen and her children’s bedroom, stuck her head in the oven, and turned it on.

Sylvia did not have to choose the perfect fig. Whichever option she chose -homemaker, poet, or professor — didn’t matter. None was the best choice. None would have been perfect. Each option would have been what she made of it.

It is not our individual choices that matter. It is who we are: the pattern of choices we make, big and small, every day. It’s our values — the things we care about most — and the way we think about the world, that define our lives.

There is no magic to making perfect decisions every time. When it comes to predicting the future, the only guaranteed way to fail is to try. Do not let a million little details convince you otherwise. Choose the general direction that suits you best, and go that way. Focus on what is most important, then let the chips fall where they may.

Do not try to choose the perfect fig. Don’t wait for life to choose one for you. Don’t fear missing out on a better fig. Instead, know what you need in a fig (fat, purple, wonderful) then grab the fattest and purplest. If you grab fast enough, you may get more than one. If you wait, you’ll miss out on them all.

Originally published at https://www.strongweekapp.com on February 21, 2021.

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.