5 Tips for Better Doubt and Regret Management

How to feel good about your big decisions however they turn out.

Posted May 14, 2018

Doubt when deciding, regret when a decision has gone wrong – these are not fun feelings. They make us feel incompetent.

They can be avoided through bluster. Some people seem to get through life without doubt or regret. There’s this US president I’ve heard about…

Still, life with no doubts or regrets is a risky and annoying way to live. I’m sure you know plenty of people who bug the heck out of you because they never seem to doubt or regret. Indeed, psychopaths have no doubts or regrets. We don’t consider them model humans.

Don’t want to be an idiot know-it-all? Expect some doubt and regret. Here are some techniques for managing doubt and regret – those two healthy human responses – for minimal pain and maximum gain when making big decisions.

1. Visualize failure

When making a big decision, minimaxing is a technique for minimizing the maximum cost of each option’s worst-case scenario.

Say you’re choosing between two options. Stay in your partnership or leave? Have kids or don’t? Switch jobs or stay? Stick with, or change careers?

You’ll probably have some gut preference based on picturing the best immediate and/or long-term consequence of one option as better than the other. For example, “Leaving this marriage will feel like taking off tight shoes and I’m bound to end up with the partner of my dreams.” Or the obverse, “Staying in this marriage is going to make my partner so much happier today and I can picture us dancing on our 60th anniversary."

Those are nice upsides and maybe they’ll pan out. But maybe not. In addition, visit the worst middle-range downsides of both options. For example, you’ll leave the marriage, feel immediate relief and then profound disappointment at what you get, maybe never partnering again before you finally adjust to a partner-less life. Conversely, you’ll stay in the marriage much to the relief of your partner but the problems will continue to fester. You’ll end up regretting that you failed to get out when you first thought you should.

To make a big decision more realistically, imagine yourself living with the downside of each option. Spending some time with each worst-case scenario will make for a more thorough decision, and maybe in the process, you’ll come up with ways to minimize the costs.

2. Floodlight

Big decisions are big because the consequences matter and it’s not obvious what to do – there are benefits and costs to each option. We often make big decisions rashly by spotlighting just some of the benefits or costs. It’s best to leave such spotlighting for after you’ve made the decision. It’s how you’ll motivate yourself to stick with a decision you’ve already made. But for deciding, it’s the rash way to go.

Instead, floodlight the costs and benefits of all the options. And don’t just shine light on them. Imagine being strapped with the costs. Pre-grieve them for each option. Project yourself into that middle-range future. Talk in the past tense about the decision you’re about to make, for example, “I bet that I should leave (or stay in) the marriage, and it didn’t work out well for me.” Picture in detail why it didn’t work out well. Do that for each option.

Picturing it won’t make it come true. That’s superstitious nonsense, like saying “I don’t drive defensively because, if I imagine distracted drivers, I’ll magically draw them to me.”

Why visualize your bets failing? If they do fail you won’t have to add self-insult to injury. You won’t feel like a naïve chump for ignoring downsides up front. You’ll have the consolation of thoroughness. You’ll know that at least you made a careful, not a naïve decision.


About bets, there’s an obvious truth that’s hard for us to wrap our minds around:  You can bet right and still have it turn out wrong. You can bet on the 75% chance and end up losing with the 25% outcome. You can bet on the 75%-chance cancer cure and still have it fail. There’s no escaping such odds, but there is escaping the gnawing exaggerated regret that if it turns out wrong you must have bet wrong. You escape that by being thorough up front.

3. Pre-finesse a rationalization for each option

Big decisions are often big because they affect others immediately. To decide carefully, you have to figure out how you would break the news to others in a way that wouldn’t erode your resolve.

You’re deciding whether to change careers? Some friends may be rooting for the change. Some colleagues may think you’d be out of your mind to leave. To avoid making a decision based just on peer reaction, think up how you could report your decision in a way that’s at least convincing to you, a way that you could declare what you’ve decided such that they respect it enough to not badger you into re-opening the decision.

Finesse an explanation for each option – that way you level the decision-making field. And do it without pretending the decision was obvious, because with big decisions, it isn’t.

See, we tend to rationalize decisions as though we made the obvious choice. But that’s a devil’s bargain. Your choice isn’t obvious, and you’ll look naïve if you pretend that it is. Instead, having thought through the worst-case scenario of the option chosen, finesse an explanation for your decision that admits that the worst-case is a possibility you recognize.

Figure out how to declare the decision confidently, saying something convincing enough to you and solid enough that in polite society people will at least humor you about it. It will give you peace of mind.

4. Don’t take the omniscient devil’s bargain.

All big decisions are bets, gambles on how things will turn out. We’d like to think that with bigger decisions we could remove all uncertainty but actually, the uncertainties grow with the size and influence. There are more consequences, more of them unforeseen, unintended and paradoxical ­– the opposite of what you were aiming for.

With big decisions, we often hunger for an infallible formula. Thinking we’ve found one is a devil’s bargain. “I did the obvious right thing” has immediate benefits, but pretending that you’re not gambling, that you’ve chosen right makes you feel better up front but at a sacrifice to the consolation of thoroughness if your bet turns out badly.

Armed with the consolation of thoroughness, you’ll be able to stand corrected more correctly, your dignity intact as you learn what you can from your bet going badly. If your bet doesn’t work out, you won’t think you were naïve, that you must have bet wrong. You’ll have regrets you can live with because you’ve been realistic throughout, from deciding through decided, to living with the consequences of your bet.

5. When regretting, remember the good and bad

Very few bets turn out all good or all bad. Did your bet turn out badly? Probably not completely, and don’t forget it. Regret motivates learning. Too much regret distorts learning. It too can make us lurch toward black-and-white thinking, all good or all bad and all obvious. You want to avoid that by learning carefully, not over-reacting, overcorrecting, taking oversteps in the right direction.

So when something doesn’t turn out well, remember this: Life is trial and error. We are all part of a great search party and our place in it has value even if we didn’t end up finding what we were searching for.

We root for ourselves of course, but we also root for the search party. We have split allegiances, to ourselves and to the search. We’ll tend to say “let the best plan win and it damned well better be mine,” but when it isn’t, remember that there are no sure-fire formulas. We’re all guessing. Chance matters.

Keeping this in mind, you’ll be less prone to stubborn insistence as a way to avoid the pain of doubt and regret. You’ll be more willing to live like a human, not pretending to be or be associated with an omniscient god. You’ll be more flexible in your commitments. Flexible commitment is a fundamental, inescapable paradox of life.

Doubt and regret – now that’s quite the pair
Both of them laced with dreaded despair.

No wonder we skirt them whenever we can
through stubborn self-certainty – just stick with the plan.

And if the plan fails, forget that it did.
“Nothing to learn here,” just snap on the lid.

For feigning control that practice will work
though it’s sure to make many decide you’re a jerk.

Both are emotions that eat at your clout.
Should you be in or should you be out?

Doubt about whether to invest in a bet
and, “there’s something to learn here” when filled with regret.

Doubt and regret – that healthy-dread pair.
They’re better embraced and managed with care.