The Counterintuitive Approach to Finding Happiness: Do the Painful Things First

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.

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 ... See more

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.

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.

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.

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

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.

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.

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.”

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.