How to Make Optimal Decisions Using The Path of Least Regret

Written by Joe Cohen, BS | Last updated:

My Taoist Approach on Using Philosophical Tools

I don’t believe people should exert energy trying to implement any trick or hack by someone else – whether by me, Tim Ferris, or anyone else.

I have a more Taoist outlook that things should flow effortlessly.

The best relationships are often those that just happened, not those that were planned out. The best jobs often come as an extension of a skill you’ve acquired from expressing your internal energy, not something you planned out.

Whenever you try to implement something positively with exertion, it uses willpower. This willpower takes out an essence from ourselves and makes us less happy and more anxious. It takes away from your future productivity if you use too much now. You get burnt out. You don’t want to waste this essence because we each have a limited supply.

I think one reason we’re so unhappy in this era is that we’re maxing out our will power. We try to control everything in a top-down approach.

Your life should flow effortlessly. I’ve constructed my own life in this manner and I love it. The more I do this, the happier I am.

These days, my life just flows. I don’t exert energy – but rather I harness the energy that already wants to be expressed.

Life is one massive journey, and it’s comparable to paddling across an ocean. You don’t need to paddle hard in an ocean. The waves and wind will do most of the work. When you paddle against the waves, your energy is wasted. When you paddle vigorously with the waves, you might go a little faster, but you will get exhausted quickly. The journey is just too long for this.

Like an oceanic journey with a paddle boat, you can’t predict your path from one point to the next. The winds and the waves are in control. I believe that your environment and genes (and their expression) are almost completely in control.

These winds and waves have a lot of energy and these are like your life force. What you can do is ride with them and let your internal energy take you where you are destined to go. You don’t need to flap your hands to create more wind.

We all have a human force that wants to create, express and improve – ourselves and the world. That force wants to make a difference.

If you let it express itself without exerting willpower, it will be expressed whether you like it or not.

I think the whole idea of a new year’s resolution is terrible. It’s an attempt to control. You are basically saying that if left to your own device, you would be lead astray – so you need a plan. Your internal force will take you to where you will be happiest in life. Trust it. You don’t need plans or resolutions.

If you find yourself procrastinating often, then you’re not truly listening to your force. Procrastination is an expression of unhappiness with what you are doing. If you are chronically procrastinating, you should ask yourself if it’s time to change something in your life.

The biggest punishment for people is to lock them in a room and not allow them to do anything – quiet time for kids, prison for adults. It’s painful for our force to be suppressed.

Coming back to my main point, I don’t think people should exert energy in implementing any tool I or anyone else presents.

You should just read it and if it resonates/suits you, you will implement it effortlessly. If it doesn’t you will forget about it and never use it. My role is just to plant the seed.

When I hear Tim Ferriss’s advice, I think most of it just doesn’t work for me. It just isn’t me. He’s trying and exerting way too much and that’s why he’s miserable and filled with angst.

This whole idea of over-exerting ourselves goes together with the modern fantasy that we control our destiny and that anyone can do anything if we just try hard enough. The Ferriss’s of the world believe we just need to find some ‘hack’ to do it. I say you should try everything and not be afraid of failing. But trying to control our destiny is bound to fail and also cause you to be unhappy and anxious.

I will never be Elon Musk or Albert Einstein, nor should I try to be. My skills lie elsewhere and I’m going to ride them where they take me.

It took me a while to understand what I’m skillful in, but now I know. You will learn in time if you don’t know yet. It can take the time to figure this out and you will need to dabble and experiment with trying to acquire different skills. You shouldn’t be afraid of trying to be good at something and failing. But also don’t keep trying if you see you’re more talented in other areas.

Ferriss speaks about being a generalist vs a specialist. His position is that we should be generalists. My position is that you should do what your internal system is driving you to do and not listen to anyone. Follow your internal compass.

Some people love specializing, while others like being generalists. You generally excel at what you like doing. If you like being a specialist and you listen to Ferriss about being a generalist, that will cause internal dissonance.

My personal style wavers. Sometimes I like to become a master at a specific field and other times I like to try new things. I just follow what my compass tells me. If you attempt to exert control, it will harm you in one way or another.

If you have a bug to micromanage and control your life then do that – but don’t do that to be ‘successful’. Do that because you enjoy the process of micromanaging and controlling. I happen to think this is a manifestation of OCD and that various biological tweaks will help you, but you should still follow the impulse of your current biology.

I’m not against Ferriss at all. Sometimes I like listening to his and other people’s ideas because maybe I’ll like something and I will effortlessly do it. Or he can give me a different perspective and allow me to see how other people view the world. So even if I disagree with him on many topics, he could still implant a seed that will improve my life in some way. However, I’ll never put an ounce of effort trying to implement anything he or anyone else says. I used to do that, but it just added complexity to my life.

He asks other people about their rituals. Oh, this is flawed thinking. You shouldn’t be copying anyone else’s rituals. You should be doing what is effortless for you. Any time you copy someone else, it requires effort.

All of the advice I hear by ‘successful’ people is completely useless nonsense. Everyone is always giving advice that worked for them, without realizing how different we really are. You should do what feels right for YOU. If you do this, then I consider you to be a successful person.

What is the Path of Least Regret?

Should you buy X? Take X job? Go back to school? Get married or date someone?

We are bombarded daily with truly difficult decisions.

I’ve struggled a lot with making decisions. As an adolescent, when my OCD was out of control, I’d be in a store for an hour thinking if I should purchase an article of clothing. I remember a good friend screaming at me back then that I wasn’t buying a house and I should just make a decision.

I’ve been using a simple tool to make decisions and it’s been working for me. I haven’t really regret any decisions or purchases I’ve made in a number of years.

Whenever I have a decision to make, I ask myself what would I say in 1, 5, 10, 20 or 60 years down the line about my decision? What would I regret the least? In some cases, I think of the worst case scenario and re-ask myself if I’d regret my choice.

If it’s a purchase I ask myself what would I say if I bought the product and it sucked? Sometimes I purchase something – say a supplement or device – and think there’s a 90% chance this won’t work for me, but I’ll figure it’s worth it if it can produce dividends for the next 60 years.

Indeed, most of the supplements that I’ve bought in the past haven’t worked for me. But I don’t regret purchasing them because it was worth it to get to the supplements that do work.

When thinking about risk, I also use this heuristic. When I up the dosage of supplements, I ask myself if I’d regret it later even if it turns out badly.

Regarding investments, I ask myself if everything goes to hell, will I look back and say this was a bad investment or will I say that at the time it was a good decision?

I use this decision in trying to find potential mates. Would I regret dating/marrying this person later on?

The Path of Least Regret and Moral Decisions

In general, the decisions that are most painful for me are those that involve something like loyalty and gratitude. I naturally have a strong sense of these, but often gratitude to someone else could hurt us much more than it will help them.

Being compassionate means to be compassionate to yourself as well.

For example, my mother cares tremendously about me and many of my life decisions bother her. She wants me to be religious, marry a Jewish girl, become a lawyer or doctor, be more ‘normal’, not have dietary restrictions, etc… And it really bothers her that I am not following her path at all. She used to call me daily, pleading with me to follow her path and advice in life.

My mother has a heart of gold, she raised me and I certainly owe her an unspeakable debt of gratitude. So it hasn’t been easy for me to completely not listen to her. It’s not illogical to say that maybe I should listen to her a little just because I owe her so much.

In a case like this, without the least regret test, my decision would be hard and I’d agonize about it for a while because I am hurting someone I love.

But when I use the least regret test, the decision becomes easy. I know there is no other path for me.

In every case, I would regret listening to her and living the life she wants me to live. This is simply because I have to live my life day after day, minute after minute and she doesn’t.

When I’m 50, I can’t see myself saying that I should’ve shifted my life path because of my truly wonderful mother. If I did, I wouldn’t be showing compassion to myself. She’ll get over it eventually, but I will never get over it because I have to face that reality every minute of my life. At any age, I’d regret listening to her and be upset with myself that I didn’t listen to my inner voice and follow my true path.

In relationships, people often change and don’t necessarily suit their partner anymore. Maybe you started dating someone when you were a completely different person. Should you stick it out because of a moral sense of loyalty or should you move on and be happier?

Using the least regret test, you have to ask yourself how much it will bother you if you move on. If it will eat at you every day of your life by leaving the person, then stick it out. If it will eat at you every day that you stayed in the relationship, then you must leave – for your own sake and for your partner’s.

Often, the answer isn’t so clear and both decisions might bother you later on, but the point is that the path of least regret makes the decision easier for you. And I would add that if you think about it and you’d regret both decisions equally, then you should realize this and just choose one over the other. I’d also suggest you work on the practice of letting go.

Other big questions include whether you should have kids and how many, whether you keep your job, go back to school, etc… The least regret test works well for them all.

A Few Big Decisions I’ve Made

I’ve used this heuristic before I started this blog. I asked what would happen if I started it and no one read it. Would I say later that it was a stupid thing to do? The answer was no, so I started it.

Three months ago, I had to decide if I wanted to do this full time. I asked myself, would I regret this if everything just collapsed? The answer was no. I even took it to the extreme. I thought of the worst possible scenarios and I still would’ve been happy with my decision.

Recently, I’ve been thinking about perhaps going to a Ph.D. program. When I asked myself if I’d regret a Ph.D. 10 or 20 years later the answer was yes.

It’s because a Ph.D. takes a really long time to acquire, is wildly inefficient and doesn’t fit with my personality – at least not where I am now. A Ph.D. would feel stifling for my current state. To spend 5 or 6 years working hard and pursuing something that there’s a good chance I won’t enjoy would cut a big chunk out of my life. And it doesn’t end there. People normally have to spend many years as a post-doc.

What would happen if after 5 or 6 years I got run over by a car and died? In the vast majority of scenarios, I’d regret that Ph.D. decision.

Even in 60 years, it’s likely I’d regret a Ph.D. because 5-6 years of the most prime time in my life is just too significant. A year I would do – maybe. My general philosophy is if you have certain smarts and work hard then you’ll be successful in this economy with or without degrees in the long term. Degrees are good for security, but they aren’t usually good for actual achievement, especially with my personality.

I’d always have it in the back of my mind that I would be way more successful and certainly happier if I didn’t get the degree.

This calculus might change next year and I might decide it’s wise. But for now, using the path of least regret, it doesn’t make sense for me.

I used the same heuristic for my drink when I decided to delay it for a while because I thought I would regret it if I moved too fast and too quickly. It would take away too much from the blog and my research and I would regret it if it failed. When things will develop more and it feels more natural, the situation will be different.

Living Your Life as if Every Day is Your Last?

There’s a meme that we should live our lives as if every day was our last. That’s terrible advice.

If I thought today was my last, I’d be depressed and meditate all day to relieve the depression.

Sure, we shouldn’t take this literally but even if I knew I had 6 months left to live, I would live it very differently. I’d probably max out my credit cards and go all over the world traveling.

The problem is I know I’d regret this for the 6 months after that because I’d be broke. So it would be 6 months of maybe being 10% happier and another 6 months of feeling significantly less happy because of financial insecurity.

The point is there are many flaws in this advice. However, when I use the path of least regret, I know I won’t regret a single day of my current life in a month, a year, 5 years or 80 years. I’ll always know I maximized the happiness out of my life to the best of my ability.

Sometimes you have to do things you don’t want to do in order to be able to do the things that you do want to. But you won’t regret this later.

The Most “Successful” People Use This

I don’t like the word successful because many people think of success solely in monetary terms, but certain people are commonly thought of as ‘successful’.

It turns out that Elon Musk and Jeff Bezos use this.

I watched a documentary a while ago in which Jeff Bezos said he had a cushy job making a lot of money at a hedge fund. He could’ve either had the security and stayed with it or start Amazon.

He asked himself, what would he say about his choice later on? Would he regret it if it failed? His answer was no.

Elon Musk started SpaceX and Tesla with the assumption that there was a good chance both would fail. He did it anyway because he deemed it worthwhile to try even if they did end up failing.

Bad Decisions Will Occur

Every day we’re faced with dozens or hundreds of decisions. It’s impossible to have 20/20 hindsight vision. No one can predict the future. Part of life is buying things you don’t like and doing stupid stuff.

But even when in hindsight I think a decision was bad, I also realize that only experience in life could have taught me what I learned. I am therefore happy I learned a good lesson and move on, happily and without regret – because I chose the path of least regret.

For example, I don’t regret the relationships or dates that I’ve had in the past because each time I came out of them wiser about what I truly want in a mate. I needed to make those mistakes to learn and make better decisions in the future.

Bottom line: “bad” decisions are almost always educational for me.

Genetics Plays a Role – We’re All Different

If it were possible that two individuals had the same exact life, the path of least regret will produce different outcomes based on their genetic predisposition.

Some of us are more thrill-seeking and adventurous, while others are more risk-averse. So part of this approach is to listen to your own biology and look for patterns of regret.

In general, however, you should be practicing letting go of regret. But where ever you are in this practice, using this tool will help you.

The Path of Least Internal Resistance

The path of least regret goes well with the path of least internal resistance.

When I look back at my life, whenever something didn’t feel right, it turned out that it would’ve been a bad decision for me.

Feeling if something is right requires self-awareness and experience. But in general, if something feels like it will take too much out of you or if there’s too much internal resistance, you should not go ahead with that decision.

Sometimes we’re just afraid of what others or ourselves will think. If this is the case, we should do it anyway. Fear is a different feeling then internal resistance and you should pay attention to the difference. This is an art, not a science.

Somehow, the true you knows what you want and you should listen to it. I consider listening to this inner voice the “path of least internal resistance.” It knows best…

Beware of the Ego

Most of the time, it’s not our stupidity that prevents us from making good decisions. It’s our ego. We are afraid of looking bad or failing.

We aren’t only afraid that other people will see us as a failure, but we’re more scared that we’ll see ourselves as a failure.

I believe that most of the time we’re scared because-because our ego is too high.

Fear is almost always not something that will benefit you. Being afraid of standing on a cliff might save your life, but in the vast majority of situations, it’s not something useful.

It makes no difference in your life if you’ve completely messed up a speech or did something embarrassing.

The fear is there because we are afraid of our image and what others – or ourselves – will think if we fail. The fear is there because of our ego.

Bottom line: don’t ever regret doing something because it might hurt your ego.

About the Author

Joe Cohen, BS

Joe Cohen, BS

Joe Cohen flipped the script on conventional and alternative medicine…and it worked. Growing up, he suffered from inflammation, brain fog, fatigue, digestive problems, insomnia, anxiety, and other issues that were poorly understood in traditional healthcare. Frustrated by the lack of good information and tools, Joe decided to embark on a learning journey to decode his DNA and track his biomarkers in search of better health. Through this personalized approach, he discovered his genetic weaknesses and was able to optimize his health 10X better than he ever thought was possible. Based on his own health success, he went on to found SelfDecode, the world’s first direct-to-consumer DNA analyzer & precision health tool that utilizes AI-driven polygenic risk scoring to produce accurate insights and health recommendations. Today, SelfDecode has helped over 100,000 people understand how to get healthier using their DNA and labs.
Joe is a thriving entrepreneur, with a mission of empowering people to take advantage of the precision health revolution and uncover insights from their DNA and biomarkers so that we can all feel great all of the time.


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