Do the Painful Things First

Before I became an entrepreneur, I went to business school. While studying for my MBA, there was one lesson that I learned which has proved to be useful over and over again in my life.

I was sitting in a marketing class and we were discussing ways to design a wonderful customer experience. The goal was not merely to provide decent service, but to delight the customer.

Behavioral scientists have discovered that one of the most effective ways to create an enjoyable experience is to stack the painful parts of the experience early in the process. Psychologically, we prefer experiences that improve over time. That means it’s better for the annoying parts of a purchase to happen early in the experience. Furthermore, we don’t enjoy it when painful experiences are drawn out or repeated.

Here are some examples…

  • If you’re at the doctor’s office it’s better to combine the pain of waiting into one segment. The wait will feel shorter to your brain if you spend 20 minutes in the waiting room rather than spending 10 minutes in the waiting room and 10 minutes in the exam room.
  • People enjoy all-inclusive vacations because they pay one lump sum at the beginning (the pain) and the rest of the trip is divided into positive experiences, excursions, and parties. In the words of my professor, all-inclusive vacations “segment the pleasure and combine the pain.”
  • If you’re a professional service provider (lawyer, insurance agent, freelancer, etc.) it is better to give the bad news to your clients first and finish with the good news. Clients will remember an experience more favorably if you start weak but finish on a high note, rather than starting strong and ending poorly.

These examples had me thinking…

If you can make a customer experience more delightful, why not make your life experiences more delightful? How can you take advantage of the way your brain processes painful and annoying experiences, and use that knowledge to live a better life?

Here are some ideas for how to do it…

To Boost Happiness, Stack the Pain

A delightful customer experience combines the painful experiences into a single segment that occurs early in the process and then improves over time. If you want to increase your happiness and have a more delightful day, you can do the same thing.

Here is an example…

On a normal day, you might have something annoying or painful to do (like paying the bills). And you also might have something good happen to you (like a friend sending you a thoughtful email).

If you read the email on your lunch break and then pay the bills when you get home from work, you will remember your day as going from a good experience to a bad experience. That’s the opposite of what you want.

However, if you decide to stack the pain early in your day — for example, if you pay your bills in the morning before you go to work and then read the email from your friend on your lunch break — you will remember your day as going from bad to good. As a result, you’ll feel happier because your brain likes it when experiences improve as time goes on.

This same principle can be applied in dozens of ways throughout your day.

  • When you’re working on a project, cleaning the house, or doing homework, start with the task that you dislike the most. Once that is out of the way, your experience will improve and you’ll finish with a more satisfied feeling.
  • When you’re trying to start a new habit, combine the pain of starting into a small segment. For example, in this article I discussed how one woman eliminated the pain points that prevented her from exercising consistently. By reducing the pain she felt at the beginning, it was more likely that she would follow through.
  • When you go to the gym, start with the exercise you dislike the most. With the hardest exercise out of the way, your experience will improve throughout the workout and you’ll be more likely to remember your workout as positive. And when you remember your workouts as positive, it’s more likely that you’ll show up next time and workout again.

Stacking the Pain for the Long-Term

It’s easy to worry about making the right choices with your life. However, if you choose to pursue things where the pain of the experience is largely in the beginning — like building a business, losing weight, or creating art — then you will tend to look back on those experiences fondly because they improve over time.

By comparison, doing things like trying to beat the stock market or become a professional gambler are very inconsistent. They can provide big wins, but they can also provide big losses at any time. The pain isn’t necessarily in the beginning. Because of this, these experiences are less likely to make you happy over the long-run.

Of course, that can be easy to forget when you’re struggling to succeed with other goals. In the beginning, it can be easy to feel like, “Building a business is so hard, why shouldn’t I try to beat the stock market?”

Understanding this difference can help you stay on track and continue to master your habits even when the day-to-day grind gets frustrating.

  • It might be painful now to put in the work required to get in shape or become a better athlete, but as your skills improve over time you’ll remember the experience as a positive one.
  • It might be painful now to create bad art, but as you master your craft and your work gets better you’ll remember the experience as a positive one.
  • It might be painful now to battle through the uncertain early years of entrepreneurship, but as you learn to build a stable business you’ll remember the experience as a positive one.

Choosing to front-load pain and discomfort isn’t just a choice that applies to daily tasks and errands. It can also be used to nudge you toward the goals you have that you tend to procrastinate on.

Where to Go From Here

If you’re anything like me, you want to get to the end of your life and remember it as being joyful and happy. Given what we know about behavioral psychology, we are more likely to remember our lives as happy if they improve over time.

This is one reason why working through the pain of learning new skills for your job, training to become stronger and healthier, and putting in the time required to master your craft is worthwhile. In the beginning, you may feel stupid while learning a new skill or frustrated while sacrificing current pleasure for a future payoff, but when you make the choice to go through the pain early, you get to enjoy the benefit of delight later on.

The path to a delightful life looks a lot like the path to a delightful customer experience. It starts off with a few painful experiences and improves over time. Using this strategy allows you to move toward happiness even when there are annoying or painful things you have to get done.

All the more reason to stop procrastinating, get the bad experiences out of the way early, and take on the hard stuff now.


  1. Great post! I talk about something very similar in my cheat sheet “10 Classy Ways to Say No.” All of them work better if you put the “no” first and then follow up with something positive. Because the message gets better as it goes along, it’s easier to say AND easier to hear.

  2. My friend had another way of looking at this. He said if you have to eat a frog, eat it first thing in the morning. If you have to eat 2 frogs, eat the big one first.

  3. Hmm this is super interesting… I wonder how this plays into the lives of athletes who are highly invested in their sport. I know quite a few football players who aren’t as contented as I feel they could be once they finish playing, and while there are a number of things involved (investing in multiple passions, defining goals into process vs. end goals, etc.) I wonder if this is a major factor. Same thing happens to some Olympic Athletes I have talked to.

    Another thought – does this argue for getting logistical stuff out of the way first in a book or a podcast episode, and ending the book or episode with something incredibly inspiring? If so, my question then is what about hooking your audience so they are invested enough to stay until the end?

    • i don’t exactly know what you mean with “logistical stuff”, but i think you could say or write something like this:

      if you want to get X, it’s important that you do these things first. actually doing these steps first will make the whole process easier for you. a lot of people do this wrong and start right of with X but won’t finish it in the end. so with doing these things first, you are already ahead of the others and closer to finishing X.

      great article James. this is probably a fundamental principle (i don’t follow way too often).

  4. The great thing about a post that draws your attention to things that you already experience, but never really put 2+2 together, is that now it’s anchored in my memory forever.

    As I read your post I kept repeating, “That’s right, that’s right. That’s right!”

    Great insight and information, James. Thanks so much for illustrating one of life’s little complexities.

  5. Hi James — here are two little expressions that I enjoy following:

    Happiness is a journey, not a destination.

    A happy life is just a series of happy moments. (If you watch for these happy moments on a minute-by-minute basis every day, you will find there are dozens and dozens of them!)

    Best wishes,
    Roger (Vancouver, Canada)

  6. Hi James, I do so enjoy reading your blog! Tons of great ideas.

    One connection you don’t point out is the “recency” aspect of doing the most fun thing last. We are hard-wired to remember the last thing more easily than the middle things.

    Since we are also hard-wired to remember the first thing we do or learn (“primacy”),I might suggest though, that it can be difficult to start with something difficult. It might be easier to get going if you start with something easy, then after you have some success dive into something difficult, and end with something fun/easy. Just a thought.

    Thanks, as always for your great posts!

  7. Thanks a lot, James! This is a great idea to consider, and I will, starting with the most “painful” stuff tomorrow morning. ;)

    All the best, Maria.

  8. James, I have a question. How would you reconcile your advice in this post with the tactic of getting the hardest and most important thing done first? I know a lot of entrepreneurs and blogger types who say that the first they do every day is write, or make sales calls, or whatever takes the most creative energy and willpower.

    Doing annoying things takes willpower and mental energy. But I find that creative tasks use up even more.

    I guess my take-away is to do hard, important creative activities first. Then do annoying stuff. Then let your day play out more delightfully. What do you think?

    • I thought about that, too, Ryan. I’ve split the difference on it. This week, I started getting up 60-90 minutes earlier to balance the bank books, pay bills, plan what I’m going to write today, and so forth. Since I already was getting up at 5:30, it’s not easy. But I was so burned out on decision fatigue by the evening, nothing was getting done. Even after just a couple of days, I’m doing more.

      So I guess I’m saying to do the creative work that you’re excited to do after the tough responsibilities that you’d put off to do the creative work. And by you, I mean me.

  9. I believe the principle of front-loading pain works because of the following reasons:

    1. When we experience pain first, this sets the level of expectation deep inside our minds. So naturally, we expect more pain in the future. But when we hit pleasure, it contradicts and also exceeds our expectations. This leads to happiness.

    2. Further, when you look at your life in hindsight and painful experiences were followed by delightful experiences, then the delightful ones are closer to your present from where you are looking back. Hence, the brain falsely and fortunately concludes life to be a pleasant one.

    An awesome article though. Dan Gilbert and Elliot Aronsohn have also pointed this out in their classic works in different contexts.

  10. This is so true. If only my college swim coaches would work this way. Our strength coach does dead lifts and squats start the work out off. But not our swim coaches.

  11. First of all, thanks for writing. Seriously, I now open my e-mail every Monday and Thursday, noticeably eager for updates.

    I recently made a schedule for practicing art about three hours a day (besides classes at the atelier I attend to) and I was on schedule for 3 days, a bit late the next three and yesterday I missed it. (Hold on with me, I’m up to something)

    I pledged to do it today and I started to, but the drawings were not as nice as the ones from the first days. Naturally, I felt discouraged and stopped. And now

    Any advice for this particular case?

    I feel ashamed of being a Lazy bum who can’t stick to a schedule. Nevertheless, I’ll do my best tomorrow.

    Once again, thanks.

  12. Very interesting to read your thoughts. This is actually the opposite of what I was taught when I was doing my PGCE (teacher training higher education). We were told to give the negative feedback first and to an end on a positive note. I spent 20 years as a university lecturer and I wonder whether I caused unnecessary emotional/psychological distress.

    • Hi Jose — It sounds like we are following the same strategy. My suggestion is to stack the pain early in the process and end well, which is the same as giving “negative feedback first and ending on a positive note.”

      Keep up the good work!

  13. Thanks for your wonderful words of wisdom. It’s not that I haven’t heard this before in a different way, it’s that I needed to be reminded of the message after a difficult day building my new business. Your timing was spot on. Thank you for helping us improve our lives.

  14. Hi, I’m writing you from Mexico. I really enjoy every post you make. I find them very interesting and I try to apply them during my day.


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