How to make decisions you won't regret

Summary

Life Kit Episode Summary: "How to Make Decisions You Won't Regret"

Released on June 2, 2025 | Host: Marielle Segarra | Guest: Nell McShane Wolfhardt, Professional Decision Coach

In this insightful episode of NPR's Life Kit, host Marielle Segarra delves into the intricate process of decision-making with Nell McShane Wolfhardt, a seasoned decision coach. Through a candid conversation, they explore strategies to make confident choices, minimize regret, and navigate the complexities of personal and professional crossroads.

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Introduction to Decision-Making Challenges

Marielle Segarra opens the episode by sharing her personal struggle with making decisions, highlighting the universal nature of indecision. She introduces Nell McShane Wolfhardt, who has dedicated over a decade to helping individuals confront and overcome their decision-making dilemmas.

“Sometimes you get stuck in your head, trapped between all the options, and you just need an outside perspective.” — Marielle Segarra [00:30]

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Understanding Regret in Decision-Making

Nell emphasizes that decision-making is fundamentally about minimizing regret. She explains that while some regret is inevitable, the duration spent agonizing over choices often leads to greater dissatisfaction than the regret from the decision itself.

“Everyone is trying so hard to avoid that really, really uncomfortable feeling [regret].” — Nell McShane Wolfhardt [05:37]

Nell asserts that acting promptly on decisions can reduce the time spent in indecision, thereby lessening overall regret.

“People regret the time they have lost deciding so much more than the occasional decision that they made too hastily.” — Nell McShane Wolfhardt [06:33]

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Maximizers vs. Satisficers

The conversation shifts to the classification of decision-makers into maximizers and satisficers. Maximizers seek the best possible outcome by thoroughly evaluating all options, which can lead to prolonged decision-making and increased regret. In contrast, satisficers opt for “good enough” solutions, resulting in quicker decisions and greater satisfaction.

“Maximizers... were also found to be less satisfied in those roles. Higher rates of maximization have also been correlated to higher rates of regret and social comparison.” — Unnamed Contributor [07:38]

Nell advises striving for a balance between these two approaches by making informed yet timely decisions based on relevant data.

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Making Decisions Based on Values and Future Goals

A pivotal part of the discussion revolves around aligning decisions with personal values and long-term objectives. Nell introduces two exercises to aid this alignment:

1. Values List: Creating a prioritized list of personal values to evaluate which options best align with one's core principles.
2. Future Projection: Envisioning one’s ideal life in 1, 5, and 10 years to assess how current decisions contribute to future aspirations.

“Sketch out 1 year ideal life, 5 years ideal life, 10 years ideal life, and then you can just take the options that you're deciding between and see...” — Nell McShane Wolfhardt [10:30]

An example provided illustrates a client choosing to remain in a stable job to build her own business concurrently, ensuring her decision directly contributes to her five-year goal of entrepreneurship.

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Testing Options Instead of Speculating

Nell advocates for experiential exploration over theoretical deliberation. By testing options, individuals can gather concrete data to inform their decisions rather than relying on assumptions.

“You can spend six months testing the waters, starting it in a small way. And by the end of the six months you will actually know...” — Nell McShane Wolfhardt [13:45]

This approach allows for informed decision-making based on actual experiences and outcomes, reducing uncertainty and enhancing confidence in the chosen path.

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Assessing and Understanding Personal Risk

The conversation addresses the subjective nature of risk and the importance of honest self-assessment. Nell advises redefining what constitutes a risk by distinguishing between perceived and actual stakes.

“The definition of risk in any decision is often relative... it's important to be honest with yourself about the stakes of your decision.” — Nell McShane Wolfhardt [17:58]

She also cautions against the sunk cost fallacy, encouraging individuals to consider opportunity costs and the potential benefits of new opportunities over the investments already made in a current path.

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Consulting Others: Whom to Approach

Nell recommends seeking advice from a select group of trusted individuals when facing significant decisions. She advises limiting consultations to three to five people to avoid overwhelming opinions that can muddy the decision-making process.

“Everyone should talk to, like three to five people when they're making a big decision. And that's it.” — Nell McShane Wolfhardt [19:27]

She stresses the importance of choosing advisors who support and understand one's values, avoiding those who may be negative or unsupportive.

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Embracing Regret to Make Bold Decisions

Nell shares a transformative perspective on regret, suggesting that accepting some level of regret is liberating and can empower individuals to make more adventurous and fulfilling choices.

“If you can accept the idea that there'll be some regret either way and accept that this is kind of a liberating idea, I think it frees us up to make like bigger and more adventurous decisions.” — Nell McShane Wolfhardt [21:35]

This acceptance encourages stepping beyond comfort zones and pursuing aspirations without being paralyzed by the fear of potential regret.

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Key Takeaways

1. Act Promptly: Avoid prolonged deliberation to minimize time lost in indecision.
2. Align with Values and Goals: Base decisions on a clear understanding of personal values and future aspirations.
3. Test Instead of Speculate: Gather actionable data through experimentation before finalizing decisions.
4. Understand Risk Relativity: Assess the true stakes of decisions based on personal circumstances.
5. Seek Selective Advice: Consult with a few trusted individuals to gain supportive and objective perspectives.

“The thing that you ought to do is often a thing that is more exciting, that is more adventurous, that really serves your true self.” — Nell McShane Wolfhardt [16:38]

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Conclusion

Marielle Segarra and Nell McShane Wolfhardt provide a comprehensive framework for making decisions that align with one's true self and long-term goals. By embracing strategies that reduce regret, clarify values, and encourage decisive action, listeners are empowered to navigate life's crossroads with confidence and clarity.

“You are going to regret it so much more if you spend half an hour deciding on that particular breakfast...” — Nell McShane Wolfhardt [06:36]

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For More Insights:

• Other Episodes to Explore:
  • Packing for a Trip
  • How to Move More Efficiently
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Produced by Claire Marie Schneider with contributions from Beck Harlan, Malika Garib, Megan Kane, Beth Donovan, Margaret Serino, Sylvie Douglas, Kwesi Lee, and David Greenberg.

Transcript

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[Marielle Segarra]

You're listening to Life Kit from npr. Hey, it's Marielle. Normally my intros for episodes come together pretty quickly, but for some reason, I got in my head about this one. I was trying to drum up an anecdote for you. A time I was struggling with a big decision. I was like, do I talk about health stuff? Nah, too personal for this one. What about a breakup? Yeah, let's not dredge all that up. What about my friend's breakup? I had someone in mind, but they definitely listened to this podcast and they would know I was talking about them. So I went over to Tony Cavan's desk. He's the managing editor of Standards and Practices at npr. Asked him to brainstorm with me and he pointed out the obvious irony here. I can't make a decision about this episode, which is about decision making. See, sometimes you get stuck in your head, trapped between all the options, and you just need an outside perspective. That's the job of people like Tony, editors, and people like Nell McShane Wolfhardt. If you've ever agonized over a decision, maybe for days on end, you've gone back and forth a million times, looked at every possible ang, until you finally threw up your arms and yelled into the ether. Somebody just decide for me. Nell is that person. She's a professional decision coach and has been for more than a decade.

[Nell McShane Wolfhardt]

Well, I invented the job, actually. I've just always been the person that friends and family came to for very straightforward advice. And if someone, even a perfect stranger, starts telling me about their problems, my brain just goes right to work, figuring out what it is that they should do. And. And eventually my best friend said very kindly, stop telling me what to do. Maybe other people want to hear this. And it turns out that she was right.

[Marielle Segarra]

Nell specializes in helping people make big, potentially future shifting, fork in the road decisions.

[Nell McShane Wolfhardt]

I'd say there's about four main categories. A lot of career stuff like should I take this job offer? A lot of location things, romantic relationships, Should I break up with this person? Very, very vague topic of discussion around here. And should I have a kid?

[Marielle Segarra]

Nell is very clear about what she is not. As in she is not a therapist or a behavioral scientist.

[Nell McShane Wolfhardt]

So I only do one thing. I offer a single session in which I help somebody make a big or a small decision, she says.

[Marielle Segarra]

An hour is usually all it takes to find an answer, no matter how big or complicated the decision may seem.

[Nell McShane Wolfhardt]

I have found in general, most people know, but they don't know that they know. You know. Sometimes it just takes talking to a complete stranger or a third party or a coach to help pull them out of it and get them on their way.

[Marielle Segarra]

On this episode of Life Kit, Less debating, More Decision making. Reporter Andy Tagle is gonna talk with Nell about how to understand your personal relationship with risk taking, how to make speedier decisions, and how to deal with any post decision regret.

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[Ira Glass]

This is Ira Glass of this American Life. Each week on our show we choose a theme. Tell different stories on that theme. Alright, I'm just going to stop right there. You're listening to an NPR podcast. Chances are you know our show. So instead I'm going to tell you we've just been on a run of really good shows lately. Some big epic emotional stories. Some weird funny stuff too. Download us this American Life.

[Andy Taegel]

You know, for me personally, I find I'm often plagued by Indecision, even when the stakes are virtually non existent. You know, omelet or pancakes? Which podcast do I start on my run? A collared shirt or a plain tee? You know what's going on there. Exactly. Nell, can you speak to the role of regret in our lives, whether it's real or imagined?

[Nell McShane Wolfhardt]

Oh, regret is so powerful. I mean, the decision making business is really just the regret minimization business. You know, everyone is trying so hard to avoid that really, really uncomfortable feeling. And because my big thing is about getting people to make decisions faster, especially omelet versus pancakes or whatever, something like that, you know, we just have to accept that yes, occasionally we will regret our choice and it's inevitable. But you are going to regret it so much more if you spend half an hour deciding on that particular breakfast, or if you spend a year trying to figure out if you should go to grad school or three years deciding if you should get engaged. I've just found that people regret the time they have lost deciding so much more than the occasional decision that they made too hastily. You know, so in general, I would say that we can eliminate a lot of regret by just moving faster.

[Andy Taegel]

The pain of lost time hurts more than the pain of regret.

[Unnamed Contributor]

Usually, yes.

[Nell McShane Wolfhardt]

Many, many more people regret taking too long to make a decision than making a decision too quickly.

[Andy Taegel]

What if you feel the opposite? You know, if you're going to a decision coach, then you're probably dealing with intense indecision. But if you feel like you jump too quickly to make a decision, how can you slow down? I often don't want to deal with the discomfort of not knowing, so. So making a decision in the short term feels good, but then I'll regret not thinking through it more.

[Nell McShane Wolfhardt]

I would say that in general, I would not encourage people to decide more slowly. And I've found in general that the amount of time you spend making a decision does not really correlate with the quality of the decision itself. You know, like after a certain amount of time, more thinking, more googling around for articles, more soliciting opinions from friends and family is not adding anything to the decision. Actually, it's just making the decision harder and. And it's making your life worse. And I often recommend that people who struggle with indecisiveness, you should take the amount of time that you think you need to make a decision and cut it in half.

[Unnamed Contributor]

What Nell is describing here is the difference between two different poles of decision makers. Maximizers and satisfies. These are the terms often used in psychology circles. If You're a maximizer. You might be more likely to suffer indecision because you're the type that seeks the best possible outcome. Chase perfection. That's not a bad thing, but it often means spending a lot of time spinning your wheels, deliberating and considering every option. Research has shown that maximizers can and do make good choices. One study found they tend to land jobs with higher starting salaries, for example. But maximizers were also found to be less satisfied in those roles. Higher rates of maximization have also been correlated to higher rates of regret and social comparison. Satisficers, on the other hand, find contentment with the good enough option, hence the contraction of the words satisfy and suffice. They make decisions that meet their basic requirements, but without always considering all the information available, which means they might sometimes be hasty and miss out on better opportunities, but are also more likely to be happy with whatever choice they make. Nel's take and takeaway one is to aim for the best of both worlds. Make smart decisions promptly, based only on the relevant data available to you, not what ifs or a bunch of outside opinions. Then, to minimize regret, separate that choice from the outcome that follows.

[Nell McShane Wolfhardt]

We are just taking our best possible guess at the time with the information that we have. Sometimes that thing is not going to work out. It turns out your new boss is a micromanager, or it turns out that your new apartment has rats. I mean, take your choice. And those things are things that it was impossible to know when you were making the decision. So I think people who feel less regret are people who are able to say, okay, I made the best decision I could with the information I had at the time, and this outcome I couldn't know in advance.

[Andy Taegel]

Let's talk about then how to make good decisions quickly. Let's talk about what that process might look like with your clients.

[Unnamed Contributor]

Can you spell that out?

[Andy Taegel]

I know the first step is understanding your values, right?

[Nell McShane Wolfhardt]

Absolutely. These are two exercises I give every client. Anybody can do these at home and just use them as a shorthand for making your decisions. First is to make a list of your values. Not moral values or corporate values, whatever they are, but just the things that make your life good on a daily basis. Mine includes never setting an alarm clock, being able to wear sweatpants all the time, being in warm weather, these kinds of things. You make the list of your values, try to put them in order of importance if possible, and then when you're making a decision, you can literally go down the list and see which one of your options you checks More boxes on that list of values. That's often an easy way to figure out, like, oh, this decision is right for me. It's more in line with who I am. The second exercise is to imagine yourself in the future. Now, I will say that everybody hates doing this exercise. Like, they really struggle with it. I also struggle with it. Humans are very bad at picturing what they want in their future. But I would say sketch out 1 year ideal life, 5 years ideal life, 10 years ideal life, and then you can just take the options that you're deciding between and see, like, okay, option A. Can I draw a straight line from this option to the life that I want? Or is it more of like a wavy line? Like, oh, well, I could take this job and do that for a while and maybe that would get me into this company and then I could try and start this project. Then I would eventually get to this part and I could start my own business. That's a very wavy line. But there's often an option on that list where you can draw just a straight line. If I had to make this choice, I can get much closer to the future that I want. Just do that one.

[Unnamed Contributor]

Could you give us an example of what that might look like?

[Nell McShane Wolfhardt]

Sure, yeah. I had a client maybe a year ago who, when I asked her to sketch out her future in five years, she wanted to have her own successful business. She wanted to be a business owner. Now, at the time she was employed, she was an employee. And the decision she was calling me about was that she'd had a job offer that was, you know, in her field and better paid and more prestigious. Should she take that job offer? On paper, that seems like an easy decision, of course, like, just take the job offer. But when we talked about in five years, she wanted to have a successful, thriving business of her own. A business that was so successful she could take time off to spend time with her kids when she wanted, or to take long vacations. She didn't actually have time to leave her first job, go to the second job, get settled in, do well, save some money, and then start building up her own business. Five years is not that long. You know, we have less time than we think. So the second option was to not take the job offer and either quit her job and start her freelance business immediately or to stay in this job, which wasn't very demanding, and to start her business on the side and then get to the, to that five year point. But either way, the idea was to be able to draw a straight line from the choice she was making to the thing that she actually wanted.

[Unnamed Contributor]

Takeaway 2. When faced with a big decision, start by listing out the things in your life that you value most in order of importance. If you can then think about future you. Where do you want to be 1 year, 5 years, 10 years from now? Nell says the most direct route to that ideal future you is likely the best choice. So really try to game that out. Like for that one client of hers.

[Nell McShane Wolfhardt]

We decided that she should stay in her current job, which was like really undemanding. The sort of job where she could take like a long leisurely nap after lunch to save money and start working very hard at building her own business in her free time. That to take that time that she would normally spend like having a post lunch nap or walking the dog or knocking off early and while she was still making that salary to go all in on building her own business so that in five years she could actually have the thing that she wanted.

[Andy Taegel]

Another thing that I really like is the idea that you can test things out. You don't just have to sit in the what if, right? You don't just have to sit in the what might it be like? Can you speak a little to that?

[Nell McShane Wolfhardt]

Yes. Huge, huge fan of testing things out. And I feel like people can test out a lot more things than they think. You know, the way we make good decisions is just not by sitting at home and wondering if we're going to like something. Right? It is by trying the thing out and then we have actual like tangible data that tells us whether or not we write, you know, we like something. So somebody wants to start a business, great. You can spend six months thinking about the business you'll start and wondering if you're going to like it and hoping people are going to pay you for it. Or you can spend those six months testing the waters, starting it in a small way. And by the end of the six months you will actually know if people will pay you for this thing that you want to sell or if you like doing it or if you like being an entrepreneur. So the same amount of time will have gone by, but you have so much more information. You can make like a real decision out of knowledge, just not out of guesswork.

[Unnamed Contributor]

Takeaway 3. If you're stuck between a rock and a hard place, get creative with your problem solving. Don't just wonder. Try the thing. Gather some data to help make your decision off of. Give yourself a deadline so you don't endlessly feel around in the dark. And in that time maybe try to look for new approaches. Nell says she's a big fan of third, fourth, and fifth options. It doesn't always have to come down to a simple this or that, yes or no.

[Nell McShane Wolfhardt]

If somebody is wondering, like, okay, should I stay at my job or should I quit to stay home with my kids? Okay, have you asked if you can go part time? Have you thought about maybe just doing some consulting gigs independently and being able to still bring in some money and still have a flexible schedule? That's the most simple example. But I think there's a lot of other ways in which you can sort of dip a toe in or find a middle ground that really might suit you better.

[Andy Taegel]

Can you talk about assessing risk? People's internal risk, thermostat. How does that come into play?

[Nell McShane Wolfhardt]

So I coached a woman who was in her early 20s, and she was thinking about dropping out of college. And on the surface, this seems like a really risky move. You know, she was almost finished. She was gonna get this degree. Her mom really wanted her to stay in college. In fact, she was afraid to tell her mom that she was thinking about dropping out. And I could have spent the whole session telling her, well, you know, you're almost there. Keep going, Stay in college, et cetera, et cetera. But when I, after I talked to her for a while and I probed a little bit and I asked a bunch of questions, it was clear that she wasn't going to stay in college, that she had already, somewhere inside, made up her mind about this decision. And I found that in general, even when it comes to things that feel risky, people are gonna do what they want to do. And my only job is to, like, pull out of them the thing that they want and then to essentially write them a permission slip and tell them it's okay to do that thing. Because most of the time, the thing that you want to do and the thing that you ought to do are the same thing.

[Andy Taegel]

The thing that you want to do and the thing you ought to do are the same thing.

[Unnamed Contributor]

Why is that?

[Nell McShane Wolfhardt]

The thing that you ought to do is often a thing that is more exciting, that is more adventurous, that really serves your true self. And people want to do those things. It's inside them that they want to do it. But it can be layered over with other people's opinions and societal expectations and things like that. But I would say that in general, if you can figure out what it is that you want to do, 99% of the time, you're good to go. Just go ahead and do that thing, and it's gonna work out better than if you force yourself to do something because other people tell you it's a good idea or they think it's too risky to do the thing you actually want, or society kind of frowns on it. You know, you're not gonna be happy doing that. It's not gonna serve you or anybody else. So if you can figure out the thing that you want, I would say 99% of the time, go do that thing. It's the best decision.

[Unnamed Contributor]

Takeaway 4. The definition of risk in any decision is often relative. Like, should you bet all your chips on that brilliant business idea, a married parent with two school age kids will surely have very different considerations than that of a retired widower living on a pension or a 20 something student intern subletting an apartment. Nell says regardless of your personal logistics, it's important to be honest with yourself about the stakes of your decision.

[Nell McShane Wolfhardt]

You know, when I ask them to imagine the worst case scenario, they, if they take this new job, it's really not, you know, they're going to be living in their car, they're going to end up in prison. The most likely worst case scenario is that they're going to end up in a job that they just don't like very much. And they're probably already in that scenario. You know, if they're interviewing for other jobs and they're taking offers, they're probably already in a job that they are not that fond of. So what's the actual risk?

[Unnamed Contributor]

And similarly, beware of the sunk cost fallacy. Nel says to remember that new or unfamiliar doesn't always equate to higher risk.

[Nell McShane Wolfhardt]

People think all the time about sunk costs, right? The time they've already put into something, the money they've invested, you know, the years of building the relationship or whatever, and they spend almost no time thinking about the opportunity costs that they're missing out on by staying in a situation that's not really what they want. You know, you're missing out on like other wonderful opportunities, maybe job opportunities, maybe relationship opportunities, these. And you're missing out on that time that you could spend really living your life enjoying yourself, doing the thing that you actually want. But people are very attached to their sunk costs. That's true. It can be hard to convince them to leave those behind.

[Andy Taegel]

Let's talk a little bit about other people. Making decisions on your own versus enlisting the advice of others is something I'm very, very guilty of. You know, is leaning on other people. When is that a good idea?

[Nell McShane Wolfhardt]

Honestly, I think that everyone should talk to, like three to five people when they're making a big decision. And that's it. By the time someone comes to me, sometimes they've talked to like 10 different people or 20 different people. Their best friends are sick of hearing them talk about it. You know, they're sick of talking. They're sick of talking about the decision themselves. And it's just really muddying the waters. You know, they're not taking in any new information. It's just other people's opinion. It's not really effective. It's not helping you make the decision, and it bores people to listen to.

[Unnamed Contributor]

After a certain point, three to five.

[Andy Taegel]

Max, you're just spinning your wheels after that.

[Nell McShane Wolfhardt]

100%. Yeah.

[Andy Taegel]

Are there best and worst people to talk to?

[Nell McShane Wolfhardt]

Well, you really have to know your audience. So, you know, I talk to a lot of people who are making decisions that they're maybe more traditional or conservative parents would disagree with. Okay, so if you know that you are talking to somebody whose values are different from yours, or they don't really respect the way you live your life, or they always have negative things to say about your choices, do not talk to those people while you are deciding. In that case, make the decision and then tell them that's what you've decided to do. Don't say, like, I'm thinking about, you know, moving to Canada. Just, you know, decide to move to Canada. Buy the plane ticket and then inform them you'll be moving to Canada. So you really have to think about your past history with everyone that you've talked to and think like, okay, does this person support me and give good advice and do I usually agree with how the choices they've made to live their life? Or is this person negative about all my choices? Just, like, pay a little attention to your past history with these people before you decide to talk to them about a decision.

[Unnamed Contributor]

Finally, takeaway five. You don't need the opinion or approval of everyone in your contact list to make a big decision. If you need to talk it out, seek the advice of a few of your most trusted, objective advice givers. Or maybe even seek out a third party like a coach, counselor, or therapist. And if you've done all of these things and you still feel unsure, or maybe if you made a choice, but now you feel some regret, Nell's got one last bit of advice for you.

[Nell McShane Wolfhardt]

I was coaching somebody who was thinking about having a kid, right? She didn't have any kids. Was a big decision she was making. And she said to me, well, I know that I'll regret it either way. And I thought this was like really great. This is almost a revelation. You know, when it comes to making a big decision, you are going to regret it either way. You know there's gonna be a small amount of regret no matter what it is that you decide to do. But if you can accept the idea that there'll be regret either way and accept that this is kind of a liberating idea, you know, it sounds bad, it sounds depressing. Like, again, we're trying to avoid regret at all costs. But if we know that there's going to be some regret either way, I think it frees us up to make like bigger and more adventurous decisions. You know, if you're going to feel bad, whether you do the exciting thing or the careful thing, you might as well do the exciting thing and see what happens.

[Unnamed Contributor]

Nell McShane Wolfhardt, thanks so much.

[Nell McShane Wolfhardt]

Thanks so much for having me.

[Unnamed Contributor]

Okay, let's recap. Takeaway 1. Don't spend longer than you need to thinking about big decisions. Aim to make smart decisions promptly by using only the relevant data available to you, not what ifs or a bunch of outside opinions. Once you've made your choice, separate it from the outcome that follows. The decision is within your control, the outcome not always. Takeaway 2. When faced with a big decision, start by assessing your values and your future plans. What's most important to you right now and in the future? The choice that helps you draw the straightest line from who you are now to who you want to be is likely the right decision. Get creative with your problem solving. Don't just wonder. Try the thing. Gather some data to help make your decision off of takeaway 4. The definition of risk in any decision is often relative. Regardless of your personal logistics, it's important to be honest with yourself about the stakes of your decision. And finally, takeaway 5. You don't need the opinion or approval of everyone in your contact list to make a big decision. And remember, if you're stuck between two hard choices, that's probably because there's both good and bad on both sides.

[Marielle Segarra]

That was Life Kit reporter Andy Taegel. For more Life Kit, check out our other episodes. We have one on packing for a trip and another on how to move more. You can find [e-mail] and if you love Life Kit and want even more, subscribe to our newsletter. Why don't [e-mail] LifeKitnewsletter Also, we love hearing from you, so if you have episode ideas or feedback you want to share, email [e-mail] this episode of Life Kit was produced by Claire Marie Schneider. Our visuals editor is Beck Harlan and our digital editor is Malika Garib. Megan Kane is our senior supervising Editor. Beth Donovan is our executive producer. Our production team also includes Margaret Serino and Sylvie Douglas. Engineering support comes from Kwesi Lee and David Greenberg. I'm Mariel Segarra. Thanks for listening.

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