How to Make Important Decisions and Never Regret Them

Reading Time: 9 minutes

The decisions we make shape the life we live. Whether consciously or not, we’re constantly deciding. To watch a movie or read a book. To get a job or start a business. To join a University or move to Thailand and live as a gong ringer in a temple. Decisions are unavoidable. And not deciding is also a decision.

But only a select few of these choices are crucial. They outweigh all the other decisions combined. A handful of moments make the difference between a life to be remembered and a story better left untold.

For Einstein, it was taking a job at the patent office. For Rosa Parks, it was saying No to a bus driver. And for Bill Gates, it was leaving Harvard to start Microsoft.

What if there was a way to recognize such decisive moments? Even better, what if there was a method of knowing the outcome ahead of time, so we could always make the right choice? It would be like playing life with cheat codes, right?

Don’t worry. This method won’t get you into trouble for cheating. But it might make your life so awesome that people will wonder if you are playing fair. If that’s a risk you’re willing to take, read on.

The story of Malcolm Little

Before I give you the blueprint for always making the right decisions in life, let me tell you a story. It began 90 years ago in Omaha, Nebraska, where a boy called Malcolm Little was born. He was the fourth of seven children.

To say he had a troubled childhood is like saying Michael Phelps was a good swimmer. His first memory was of the Ku Klux Klan burning down his home. He was four. At six, his father got killed. At 13, his mother was dragged into an insane asylum, leaving Malcolm to grow up in a foster home, away from his siblings.

What followed is no surprise. Malcolm dropped out of school and started stealing, dealing drugs, and gambling. He became a con-man and a pimp. Eventually, he got arrested and sentenced to 10 years in prison. He was 20.

If I stopped telling you this story right now, what would you say happens next? He gets in a prison fight, stabs two guys, and serves a life sentence, right? Or he gets out after ten years, starts dealing drugs again, bangs a few prostitutes, and dies of syphilis. Any such scenario is far more likely than what actually happened.

In prison, Malcolm made a decision — one that would turn his life around and earn him a place in the history books. Instead of joining a gang or pumping iron, he spent time with an inmate called John Bembry. Malcolm described him as “the first man I had ever seen command total respect… with words”. Malcolm decided he wanted to do the same — stop demanding respect with guns, and start earning it with ideas.

At first, he was frustrated because he couldn’t express his thoughts properly. So he went to the library. He spent weeks copying a whole dictionary, from aapa and aardvark to zwieback and zygote. He wrote every word by hand. Next, he started reading anything he could get his hands on. When he finally felt ready, Malcolm began writing letters to someone he admired (a religious leader called Elijah Muhammad).

Reading veraciously and exchanging ideas not only changed Malcolm’s attitude toward the world — it changed his destiny. To mark this pivotal moment, he also changed his name. From then on, he would be known by the same name you’ve heard about him in history class: Malcolm X.

What would his life have looked like if he hadn’t made that decision? Your guess is as good as mine. But one thing is certain: had Malcolm not recognized the importance of that moment, I wouldn’t be writing about him 70 years later. So how can we identify such moments in our own lives?

Photo by Mathew Schwartz on Unsplash

How to identify crucial moments

35.000 — no, that’s not the number of hookers Charlie Sheen has sponsored. It’s the estimated number of decisions we make every day. Multiply that by 365 days and by 60 years. What you get is… well, it’s a number you can’t even read, let alone do anything meaningful with it.

So how are we supposed to recognize which one of these decisions is crucial for our life?

One can argue that each of these decisions has the potential to change your life. Every time you decide to go buy milk you could bump into the man/woman of your dreams. But that’s like saying every blogger has the potential to be the next Hemingway. Sure, in theory you may be right. But we’re not here to discuss theory. You want clear-cut advice, so here it is.

Whenever you’re in front of a major life decision, you feel it in your gut. I know this doesn’t sound scientific, but it’s how things work. Your brain processes information on many different levels, and one of them manifests itself as intuition or gut feeling. It’s the feeling you get before moving to a new country, handing in your resignation, or asking someone to marry you.

If you don’t know what I’m talking about, you’re too young to ask yourself such questions. Don’t sweat it. You’ll find out soon enough. And if you have such strong feelings every other day, there’s an easy way to separate the life-altering moments from the wannabes.

Before making the decision, ask yourself what impact it will have in 10 years. Will you look back and see it as pivotal? Is this the type of decision you will tell your grandchildren about? If so, then let me sho you how to make the right decision. Every single time.

How to always make the right decision

This is a three-part process. Going through all the steps won’t be easy, so reserve it for the decisions you have identified as crucial. Otherwise, you might end up with analysis paralysis or procrastinate yourself to death. This is a finely tuned, high-precision decision sniper. Use it wisely.

1. Decision making by surrogation

Remember what I said earlier about playing life with cheat codes? When I was in third grade, I loved spending my evenings playing Wolfenstein 3D. There’s something about running through an underground dungeon shooting pixelated Nazis that helps you wind down after a long day. It’s even better when the guards can’t hurt you. You guessed it: I was using cheat codes.

I wasn’t using them all the time — that would be boring. But whenever I got to a particularly hard level, I would enter a cheat code to learn more about the environment. I looked for the fastest way to get to the boss, study his moves, and time his actions. Then, armed with my newfound knowledge, I would restart the level and play it for real.

Wouldn’t it be great if you could do a similar thing in the real world? Well, you can. Except for the killing Nazis part — that I wouldn’t recommend.

Whenever you’re in front of a major life decision, find someone who has faced a similar choice before. First, look for general similarities: people who have also had the opportunity to move to another country, make a big career change, or whatever your dilemma may be. Make a list of those persons.

Next, narrow it down. Look for people who have training, ideals, or interests similar to yours. People who want the same things in life, dispose of the same resources, or have the same dreams as you do. Ideally, you want someone who has your background and was in your exact place 10 years ago.

Granted, that’s hard to find. But if you take a long, hard look at everyone you know, I’m sure you can find a person who is close enough. Then, reach out to that person. This can seem awkward, especially if it’s someone who’s not that close to you. But this is a decision that can affect your whole life, so screw the awkwardness.

Explain how important this is to you and what impact their help will have. They will understand. You can also make it easier for them (and more helpful for you) by asking clear questions.

  • Why did you make this decision?
  • What were your hopes back then?
  • What are your regrets?

Ask anything relevant to your current dilemma. If you do it right, you’ll get a pretty accurate simulation of the outcome — and with it, a tiny simulation of your future life. No cheat codes involved.

You must learn from the mistakes of others. You can’t possibly live long enough to make them all yourself.

Samuel Levenson

2. Interviewing the right candidate

This is one of those things I wish I’d discovered earlier in life (you can read the other 30 things here). You can learn something from every person you meet. And when it comes to major life decisions, older people are often your best bet.

In my walks, every man I meet is my superior in some way. And in that, I learn from him.

Ralph Waldo Emerson

Last year, I started a small personal project. After making several poor decisions and later realizing how much stress, anxiety, and effort I could have avoided, I decided to finally do something about it. My bet was that other people have made similar mistakes in the past — smart people, from which I could learn. So I made a list of all the people I admired and asked them one question:

What advice would you give your 30-year old self?

Your question or selection criteria may differ. But the method is the same: look for someone who already is where you want to go. Find people who are living the life you dream of, who are working your dream job, or who have achieved something you aspire to. Then interview them.

Find out what it’s really like to be living the dream — not just during the good times, but also during the shitty ones that came before the glory. Then, and only then, can you make an informed decision. Is the sacrifice worth the effort? Or would you rather look for a different path?

3. You can have your cake and eat it too

When she was younger, my daughter wanted to touch the coffee cup every time she saw me drinking. No matter how often I would tell her it’s hot, she still wanted to see for herself. And I can’t blame her — daddy isn’t any different.

Learning through experience is one of the best ways of making sure a lesson sticks. We are far more likely to remember something after doing it, than after just seeing or hearing about it. But it’s one thing to learn that touching hot objects is a bad idea. It’s an entirely different thing to find out you’ve been toiling at the wrong job for the past 15 years. Or that you’ve married the wrong person.

What if you could gain the experience without exposing yourself to the risk? Turns out you can. It’s called shadowing. Think of it as internship — but without fetching coffee and kissing the boss’s ass.

Again, find a person you admire. Ask if you could spend some time watching him/her up close. Tell them you admire what they’re doing. And that you want to spend some time in their shoes, so you can see what it’s really like.

This could mean doing 3 night shifts per week alongside a medical resident. Or spending a few days and nights with a mother of three. Or tagging along with a successful lawyer, working 80 hours/week. Whatever your dream may be, use this technique to immerse yourself in the day-to-day aspects of it. This way, you can gather first-hand experience, without any risk of consequences. Only after doing this final step should you decide if you want to pursue this dream further.

Fools learn from experience. I prefer to learn from the experience of others.

Otto von Bismarck

Bonus: build your own compass

Photo by Colton Sturgeon on Unsplash

Our minds are weird and dangerous things. We forget, reinterpret, and misremember stuff in the most convenient ways. A poor argument leading to a good result doesn’t mean you made the right decision. It means you got lucky.

The first principle is that you must not fool yourself, and you are the easiest person to fool.

Richard Feynman

But if you can’t trust your mind, how are you supposed to make important decisions? After all, it’s our mind that makes them.

The secret isn’t to take our mind out of the equation, but to eliminate any subjective tendencies that may distort reality. Which sounds way more complicated than it is. All you need is a pen and a notebook. Using these cutting edge tools, we will create a high-tech reality distortion scrambler — which I call a decision journal.

Every time you are faced with an important choice, grab your decision journal and write down 3 things:

  1. The decision itself (e.g. I decided to move to a new country)
  2. The reasons/hopes behind it (e.g. I was fed up with the authoritarian regime and hoped to enjoy more freedom in another country)
  3. Termination clauses (e.g. if more freedom makes me depressed and miserable, I will go back)

This will be your own decision compass, always showing the true north regardless of the circumstances. It will prevent packing your stuff and moving back into your parents’ basement after a rough day at work. And the termination clause will keep you from persisting with a decision if it conflicts with important aspects of your life.

Whenever in doubt, pick up your decision journal. It will help you remember why you made this decision in the first place. Is it still bringing you closer to your goal (albeit slowly and painfully)? Then grab a beer and chill. Nobody said this would be easy, but you’re on the right track. That’s what matters.


Like anything in life, this method isn’t perfect. Your mileage may vary. But at the end of the day, you will know you did all the research, weighed all the options, and did everything you could to make the right decision. And often that’s more important than the decision itself.

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Pair with The Autobiography of Malcolm X and How to Make Tough Decisions Easy and Have a Happy Life


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