How to use regret to make better decisions

Have you ever wanted to live a life of no regrets? As I was reading The Power of Regret by Daniel H. Pink, he discusses how regret is universal and that we can harness its power to make better decisions. His research projects on regret identified the types of regret discussed and how we can use our regret to benefit our lives.

Photo by Marcos Paulo Prado on Unsplash

Main impacts

These are the key points that stood out to me:

  1. Inaction regret is stronger than action regret
  2. Regret can make us better
  3. Use anticipated regret to your advantage

Keep reading to find out more about each one.

Inaction regret is stronger than action regret

Inaction regret is when you regret not doing something, compared to action regret is when you regret doing something. For example, inaction regret would be not asking someone out on a date compared to an action regret of going on a date with someone.

Inaction regret tends to be longer lasting and produce stronger feelings. It leaves you with an unknown, forever pondering “what if?”. Inaction regret leaves you wishing that you had done something, and leaves you wondering what could’ve happened and what your life would be like now. These kinds of regrets might prompt questions like, what if I pursued a different degree or career, what if I’d gone on that trip, or what if I’d done this sooner? The unknown is what makes the regret so much stronger.

I’d rather regret the things I’ve done than regret the things I haven’t done.

Lucille Ball

Personally, that just sounds like strong encouragement to take risks and do the things you fear, rather than living with the unknown of “what if?”. Seems like people can more easily accept regrets from what you’ve done rather than what you haven’t. So lean towards action rather than inaction, embrace the risk, and take that leap of faith. Most of the time you can always go back, but you may not have this opportunity again.

Four types of regret

In the book, Daniel talks about how it’s easy to see regret in different areas of people’s lives and that was initially how they started categorizing the regrets (such as career, education, family, relationships, etc.). But the more regrets he read about, he started to see overarching thematic themes, rather than where it occurs. The four themes were foundational, boldness, morality, and connections.

These are the four types of regret used throughout the book:

  • Foundation: these regrets refer to putting in the work and building a solid foundation to build on. This could be relating to finance (saving earlier), education (doing the work), career (putting the effort in), etc. It’s about looking back and realizing you could be so much farther ahead if you did the work at the beginning.
  • Boldness: these regrets refer to taking a risk and being bold in any area of life. This could be things like being more confident and talking/meeting people, taking the leap of faith and making a change in your career/education/living situation, or just doing things outside your comfort zone.
  • Moral: these regrets surround some kind of moral decision, either not doing the “right thing” (inaction) or doing the “wrong thing” (action), for whatever you perceive to be morally right or wrong. Common regrets in this category involve cheating (relationship-related or otherwise), and harming others (emotionally/physically/mentally/etc., such as bullying).
  • Connection: these regrets all involve some kind of relationship or human connection, it could be a breaking of a relationship or one that never fully formed. The ones that break tend to happen either as a drift (slowly falling/drifting away from each other) or a rift (some large event creates a rift).

When each of these are an inaction regret, it looks like:

  • Foundation: if I’d only done the work.
  • Boldness: if I’d only taken the risk.
  • Moral: if I’d only done the right thing.
  • Connection: if I’d only reached out.

Regret can make us better

We can use regret to inform our future choices and make better decisions. Regrets can improve our future actions by learning from our regret and truly understanding why we regret it. One of the best ways to use regret is to make a different decision when the opportunity arises again, such as taking the risk, reaching out, making the right decisions, etc.

When used properly, we can use regrets to improve ourselves, not to self sabotage. If we take time to reflect on what we regret, then we can make sure we don’t keep making the same mistakes. Reflecting also helps you to move on and move past your regrets. But make sure you’re not just dwelling on your regret, dwelling without change is not useful. If we ignore our regrets and pretend like they don’t exist then we will likely keep making similar decisions.

You may always have that regret as it’s unlikely you can go back in time and change what you did. But you can grow from that experience and minimize future regrets by making better decisions in the future. Regrets can help guide our growth by showing us who we want to be, what’s important to us, and what kind of decisions we want to be making.

Use anticipated regret to your advantage

You can use anticipated regret to help avoid bad decisions. Anticipated regret is when you take time to consider if you’ll have any big regrets before making a decision, by considering regrets from both making the decision or not taking any action (remember those inaction regrets).

This anticipation of regret can be useful, but it can also be exaggerated to just become a form of procrastinating. You have to be careful that you’re not using the idea of “avoiding regret” to avoid all risk. Some risk may be inevitable, you won’t always be able to know what you’ll regret, but that shouldn’t prevent you from taking risks and making decisions.

The goal of anticipated regrets is not to weigh every little decision, but to be mindful of the big decisions you make.

Generally, if you think the regret is not going to land within one of the four main categories of regret (foundation, boldness, moral, connection – see above for more details), then make a decision quickly and move on. However, if it might be within one of the four big categories, then take some time to consider future you and how you will feel in each of the potential outcomes, weighing the anticipated regret from each option. This reflective exercise can hopefully allow you to avoid the largest regrets.

Final thoughts

I found this book thought-provoking. It reminded me of the list of the top regrets of people dying (the essay by Bonnie Ware), especially how there were such strong themes across all demographics.

I liked how the book is based off of ongoing research (you can still take part in the survey now!) that covers a huge range of ages, geographic locations, gender/religion/sexual identities etc. Having such a large sample size with all kinds of people, shows how universal regret is. We all experience some kind of regret, and that’s normal. It further reinforces the idea that all humans share the same wants and desires, no matter who we are.

Nowadays, it feels like most people want to live a “no regrets”/YOLO kind of life, which isn’t really realistic. I liked how this book highlighted the ability to both accept and embrace your past decisions, while still learning from the experience and choosing to move on. When you make the most of your regrets, you’re able to move on and make better decisions in the future. It doesn’t mean you no longer regret the decision, but it seems to provide a way that reduces negative impacts of dwelling on regret.

I don’t feel like this book was revolutionary or mind-blowing. It essentially boils down to “learn from your regrets”. The book was pretty much what I expected it would be. However, I still enjoyed listening to the audiobook. It was still interesting to hear about the universality of regret and ways we can use it to make better decisions.

If you’re interested in regret or the shared human experience of life, you may find this book interesting.


Did you know timing can be a science?

Have you ever wondered how important the timing of events is? As I was reading When by Daniel Pink, he discusses the science behind the timing of experiences and events. He discusses that when things occur can be as important as what is happening, and helps you to understand when you should be scheduling your time so that you get the best outcomes.

Photo by Nathan Dumlao | Accessed on

Main impacts

These were the key points that stood out to me:

  1. The power of endings
  2. When can be just as important as what
  3. Breaks are important

Keep reading for more details on each.

The power of endings

Endings tend to be much more memorable than the rest of the experience. You rarely remember experiences as an average of how you felt throughout it, rather you’re more likely to remember an experience based on key moments and/or the ending.

Therefore, endings can significantly impact how you felt about an experience or situation. If the overall experience was either bad or just not great, a good ending can change your memory of the experience to be much more favourable. It’s not just good endings, but poignant or memorable endings can also override a negative feeling from an experience.

Even if the experience is longer and more painful, you’re more likely to judge the experience by the ending. See my post on the book The Power of Moments by Dan and Chip Heath, that talked about an experiment where people showed this bias when having to keep their hand in cold water.

Generally, how the ending makes you feel is how you will judge the rest of that experience. Whether it was a day, a vacation, an employment, or a conversation, the ending can have a huge impact on your memory and feeling of the experience, whether or not you consider it to be a fair judgement.

But you can use this to your advantage! Whenever you are planning something, be mindful of the ending and find ways to make it more memorable or enjoyable.

A tip for a better work day!

Here’s a tip to having better work days. At the end your workday, take a few minutes to reflect on what you did, make a note of what you’ve accomplished and how it went, and maybe even send a short thank you message/email to someone. Taking a moment to reflect on the positive aspects of the day and your accomplishments (small or large), will help to end your day in a positive way and can leave you feeling better about your entire day.

When can be just as important as what

When you do things can be just as powerful as what you choose to do. Which means you should always take into consideration the timing of your schedule, such as big decisions (made by you or someone else), life changes, etc.

There are certain times of the day when we are more likely to pick the easier option, whether or not it’s the right decision. We tend to default to the easiest option. One of the examples in the book was judges deciding if a prisoner should be released on bail, and the study showed that judges were consistently less likely to release prisoners on bail if they were making the decision right before lunch or a break (taking into consideration all other factors).

Another example was talking about when we should, or rather shouldn’t, go to the hospital. Apparently the worst time to go to a hospital is in the afternoon, because that’s when they tend to make the most mistakes. The afternoon is usually at the end of a very long shift, meaning the doctors or nurses have been working long hours and are more likely to make a mistake.

In the book, Daniel also talks about sleep chronotypes, which identify if you’re a morning or evening person, or somewhere in between. Understanding which chronotype you have, will highlight when you will have peak energy levels and help you to plan your activities throughout the day. Some parts of the day are best for deep work, whereas others are better for the less intensive work, but these times differ based on your chronotype.

There are so many interesting details in the book on knowing when to do big life changes, decisions, or even daily routines. In the end, timing is a science, and there’s a lot of information on how to use that timing for the best outcome.

Breaks are important

Taking breaks can make you even more productive. Breaks are important on a daily basis, throughout the workday, and also over longer time frames. A break can help you reset and give you fresh perspective, not to mention help improve your energy levels. All of this allows you to return to your work refreshed.

During the day, it’s important to give yourself a break from focused work. It’s great to have dedicated time for focused work, but don’t forget to break it up with time away from your work. It’s always better if the break also includes movement by stretching, walking around, etc. or other people such as making it social (think water cooler talks).

In the theme of breaks, one of the types that Daniel advocates for are naps. Naps can provide so many benefits, and leaving you feeling so fresh. Just make sure that the naps are not too long, around 20 min or less is ideal. There are also a handful of locations around the world that have naps (siesta and others) built into their culture.

Ideally, you should integrate breaks into your daily routine and long term thinking. Make sure to be strategic and deliberate, by picking the time that works best for you and scheduling your break (otherwise you might not take them).

Final thoughts

This was a really interesting book, with so many useful details. I want to re-read it as I realized I don’t remember all of the details.

There’s so much that affects how we feel and we don’t even realize it. The more we understand the science of timing, the better we can use it to get the best outcomes and have great days.

I like this because it wasn’t another productivity book about how to do THE MOST amount of work in a day. That wasn’t the purpose at all. It was about understanding how to schedule your days (and life) to get the best results. It wasn’t about working more, it was about finding what works best for you and understanding why it works for us.


Here are some useful links:

  • You can buy the book on Amazon here.
  • You can find more information on the book on Goodreads here.
  • You can find information from the author here.
  • Here’s the author’s website here: