How to Stop Being Fooled Into Choices You Regret

If you remember this one tip, you’ll be safer, smarter, and happier.

Posted Aug 06, 2019

Everyone makes mistakes. Here, I’ll suggest that there are two kinds: the ones we make when we dial in the wrong tactics for the task at hand, and the ones we make when we treat tactics as though they’re surefire formulas.

We learn from the first kind, getting better over time at figuring out which tactics to dial in when. The second kind – treating tactics as surefire virtues – stunts growth and impedes learning.

Make the first kind of mistake, not the second, and you’ll live a safer, smarter, happier life because you’ll learn from your mistakes, getting better at knowing which tactics to dial in when.

Here, let me explain.

Whether we admit it or not, we’re all living the serenity prayer, trying to decide what we can and can’t change. And not just that – we’re also all living variations on the serenity prayer, seeking the wisdom to know the difference between when to speak or be quiet, reward or punish, be blunt or tactful, cooperate or compete, hold or fold, be loyal or defect, settle or keep looking, raise or relax our standards – the list goes on (see below).

The serenity to accept and the courage to try to change things are tactics, as are the options paired in any variation on the serenity prayer. Throughout our lives, we guess when to dial in which tactic.

The serenity prayer has a weird term in it: “Wisdom to know.” Aren’t wisdom and knowledge different?

“Wisdom to know” could mean either of two things. One is that you’re officially wise if you know precisely when to dial in serenity and when to dial in courage.

The other is that the wisdom is in the praying, not to God or some magical wise source that always knows what to dial in, but rather in the questing all learners do. The wisdom is in wanting to know the differences between when to dial in which tactic. In other words, it’s wise to want to get better at dialing in the right tactic for the situation, cultivating smarter intuitions about best tactical responses in different circumstances.

Failing to dial in the right response is how the first kind of mistakes happen, for example pushing courageously for what can’t succeed or accepting serenely on what could be improved. On the one hand, it’s a mistake to flog dead horses. On the other, it’s a mistake to walk away from a gold mine.

Since we never have absolute wisdom – some perfect formula for dialing in the right tactic for the situation, we’ll be wrong sometimes, making errors of both kinds:

Courage when serenity would have been the better tactic: “If only I hadn’t been so attached to winning. I just kept pouring good money after bad.”

Serenity when courage would have been the better tactic: “If only I hadn’t given up so easily. I should have known that success was just around the corner.”

It’s like learning to drive. At first you might veer too much to the left or right on some winding road, but over time you get better at keeping away from either shoulder – not perfect but better, and anyway life is way more complicated than driving winding roads, hence our ongoing, lifelong quest for refined knowledge about what tactics to dial in for changing circumstances.

There’s no escaping our serenity prayer lives but there is pretending we’ve escaped it. This is where we get mistakes of the second kind, pretending we’ve already got the wisdom to know what to dial in when.

There’s something in us that would like to stop questing for better tactical knowledge. We’d like to feel like we’ve already got official wisdom – all the knowledge we need. That feeling comes in handy when we doubt we’ve dialed in the right tactic, an anxious feeling we often have.

It’s easy for any of us to claim we’ve already got all the wisdom to know. All you have to do is treat any sometimes-useful tactic like it’s always the right tactic. To justify a choice, people often talk like it’s always the right choice.

“Why am I choosing to be serene and accepting? Because serenely accepting is always the right answer. Obviously.”

"Why am I courageously trying to change things? Because having the courage to change things is always the right answer. Obviously.”

Wait. If they were both always the right answer, you wouldn’t need to know the difference between when to apply which.

Still, to rationalize a choice, we’ll often pretend it’s not a tactical choice but a moral duty. Always be loyal. Always be generous. Always employ this one tactic and not its opposite. We’ll even switch between tactics as absolute virtues mid-sentence:

“I should be allowed to speak because people should always be allowed to speak and you should be quiet and listen because people should always be quiet and listen.”

Treating a tactic as always virtuous is as growth-stunting as explaining why you turned right instead of left at some intersection by saying one should always turn right.

We often overgeneralize from successes too:

“Why should we always turn right? Because, once I was at a crossroads, I turned right and got where I wanted to go. From that, I learned that one should always turn right.”

Such moralized tactics are words to the unwise, the un-questing, and over-rationalizing. Throughout your life, you’ll hear a lot of those unwise words, for example, people touting loyalty as though it’s a supreme virtue when it’s actually a tactic to apply selectively.

You’ll hear people touting serenity or courage as though they aren’t just positive names for tactics that have absolutely negative consequences in some circumstances. It’s absurd: The serenity to accept someone killing your family? The can-do courage to stick loyally with a crusade for evil?!

Pretending a tactic is a pure virtue will relieve you of having to quest for wisdom. It will also relieve you of any good fortune you have. It will stunt your growth and make you an absolute hypocrite, pretending you always turn right when, in practice, you’re still living your serenity prayer life, turning right sometimes and left other times like everyone else.

There is something general to learn from every step and misstep. Learn to keep learning. Don’t lurch toward easy formulas for pretending that you’ve found the right tactic for all situations. Remember that they’re tactics. Remember that you’re never going to escape the work of dialing in the right tactic for the situation. That’s life. Just keep living and learning.

Here are some variations on the serenity prayer that there’s no escaping – each followed by some half-wit cop-out you’ll hear for pretending that we can escape them.

1. Should I try to change this?

Grant me the serenity to accept the things I can’t change, the courage to change the things I can, and the wisdom to know the difference.

Be serene, never stubborn!
Be steadfast, never spineless!


2. Should I join this?

Grant me the enthusiasm to join the things that will prove to have been worth joining, the aversion to not join the things that will prove to have been not worth joining and the wisdom to know the difference.

Always be a team player, never be a trouble-maker!
Always think for yourself, never be a sheep!


3. Should I stay with this?

Grant me the dedication to stay with the things that will prove to have been worth staying with, the impatience to not stay with the things that will prove to have been not worth staying with, and the wisdom to know the difference.

Always be loyal, never a quitter!
Liberate yourself, question authority!


4. Should I be consistent here?

Grant me the flexibility to try new things in situations in which changed behavior will pay off, the steadfastness to be consistent in situations in which changed behavior will not pay off, and the wisdom to know the difference.

Always be flexible, never pigheaded!
Always stick to your guns, never be wishy-washy!

5. Is this significant?

Grant me the focus to concentrate on the things that will end up proving significant, the obliviousness to ignore the things that will end up proving insignificant and the wisdom to know the difference.

Stay focused, don’t dither!
Care about everything, no tunnel vision!

6. Should I say this?

Grant me the honesty to say what will prove to have been helpful, the tact to not say what will prove to have been unhelpful and the wisdom to know the difference.

Speak your mind, never lying!
Be tactful, never unkind!

7. Should I sacrifice here?

Grant me the selflessness to sacrifice in situations in which the payoffs to the group will prove to have been worth it, the selfishness to do my own thing in situations in which the payoffs to the group will prove to have been not worth it and the wisdom to know the difference.

Be selfless, never selfish!
Be tough, never bending!

8. Should I delay gratification here?

Grant me the patience to delay gratification when the future payoff will prove to have been worth the wait, the impatience to gratify now when the future payoff will prove to have been not worth the wait and the wisdom to know the difference.

Seize the day, demand more now!
Be patient, never impulsive!

9. Should I keep hoping here?

Grant me the yearning that keeps hope alive when I will be able to make my dreams come true, the realism to let go when I won’t be able to make my dreams come true and the wisdom to know the difference.

Always stay hopeful, never give up!
Cut your losses, don’t be attached!

10. Should I regret?

Grant me regret when there are lessons to learn that will prove helpful with future choices, no regrets when there are no lessons to learn and the wisdom to know the difference.

Stay proud, no regrets!
Be humble, always admit to your mistakes!

11. Should I expect more of the good I’ve got here?

Grant me the sense of entitlement to expect more of the good I’ve had when it will be forthcoming, the surrender to let go of the good I’ve had when it will not be forthcoming and the wisdom to know the difference.

You’re entitled to what you’ve come to expect, never compromise!
You had your day in the sun, be grateful and always let go!

12. Should I give here?

Grant me the generosity to give to those who will be motivated by it, the firmness to not give to those who will not be motivated by it and the wisdom to know the difference.

Always be generous, never stingy!
Set firm boundaries, don’t be a pushover!

13. Should I keep track of who owes what here?

Grant me the contentedness to stop keeping track of who owes what in cooperative friendship, the wariness to keep track of who owes what in competitive negotiations and the wisdom to know the difference.

Don’t be controlling, be open to whatever!
Don’t let people walk all over you, demand what you deserve!

14. Can I trust them?

Grant me the trust to invest in those who will prove trustworthy, the wariness to distrust those who will prove untrustworthy and the wisdom to know the difference.

Don’t be paranoid, be trusting!
Don’t be fooled, always be wary!

15. Should I comply with the letter of the law?

Grant me the obedience to comply with the letter of the law when it serves the spirit of the law, the defiance to disobey the letter of the law when it doesn’t serve the spirit of the law and the wisdom to know the difference.

Be principled; don’t cut corners!
Do what’s right, even when it defies the law!

16. Should I doubt?

Grant me the doubt that motivates a search for more wisdom when the path is unclear, the confidence to stop searching when the path is clear and the wisdom to know the difference.

Always trust your gut, don’t second guess!
Think and doubt always, don’t assume!