The Surprising Way to Enjoy Work

Confession: I don’t always enjoy working. It makes me procrastinate sometimes.

I have, however, figured out how to work whenever I want, and the solution isn’t what I thought it would be. It’s all about my expectations.

Last year, I went to a concert of my favorite band, CAKE, and being a fan for years, my expectations were extremely high for the concert. Looking back, the performance was fantastic and I should have loved it, but I didn’t enjoy it as much as I’ve enjoyed some other concerts. Why? My unrealistically high expectations reduced my enjoyment of the concert more than any other factor. 

Managing Your Work Expectations

When I first think about starting a new project, there’s some amount of fantasy involved. That is, I’m not thinking about the work sessions in which I think so hard I fall asleep, or the hours that feel like an unproductive grind of slow progress. I shelve those thoughts, and instead think about the satisfaction of the finished project. I tend to misattribute that satisfied “I’m finished” feeling to doing the work itself. 

When you expect work to be more enjoyable than it will be, you give yourself no chance to enjoy it. 

If you expect work to be satisfying, impressive, and “clean,” then you’re likely to never start (and even if you do, you won’t like it). The moment you consider actually doing a work task, you’ll be faced with dozens of imperfections. Maybe you’re tired. Maybe you’re distracted. Maybe you don’t have any good ideas right now. Maybe later just seems like a better time to start. Such imperfections are the reality of every work session.

If, however, you fully expect this more realistic version of working on your project, you’ll be much more willing to do it. It’s not pessimistic to expect work to be well, like work, it’s creating realistic expectations to increase your enjoyment and willingness to work. 

I’m proud of the books and courses I’ve created. They’ve helped a lot of people and are rated highly for their quality. But the individual work sessions required to get them to that point was usually some combination of messy, irritating, dull, and inconvenient. There were no angelic choirs playing as I strained to come up with useful ideas. I experienced more blank-minded creative tragedies than epiphanies.

This is not unique to my profession. This is the nature of all kinds of work: You have to put in a lot of ugly, frustrating, and difficult hours to create beautiful results. Yes, sometimes you will “get on a roll” and have a dream session of work, but those are few and far between, and you will only find such gems by digging through the mud first.

The Best Way to Approach Work

When you consider working—whether it’s household chores, business projects, or anything else—don’t expect it to be a smooth, fun, exciting time. Expect it to be bland but demanding, frustrating at times, and somewhat unappealing. But, and this is key, you can also expect it to be totally worth it. Expect to feel satisfied afterwards with what you’ve done. Expect to feel a burden lifted off of your shoulders for doing it now instead of later.

With this approach, you won’t put off work because you expect it to be “a better situation” later. You’ll recognize that work is always a flawed but worthwhile action, and that now is always the best time to do it. This perspective is important because it correctly kills the idea that a perfect work situation will ever happen.

How many times have I allowed the fantasy of a perfect work session ruin my present opportunity to do good, plain work? Too many! When minutes, hours, or days pass and I’ve done nothing, I feel that familiar burden of unfinished work weigh on me. And yet, my situation is no more suitable for work. Deep down, I know the always-present imperfections of work never change.

I’ve been most productive when embracing the “rough” nature of work. It allows me to experience the intermittent joys of good work while preparing me to handle the inevitable slog through the work doldrums. If I let my work fantasies run, real work will rarely be appealing enough for me to get started.

Think of working as a mud run. If you expect a clean track, you won’t take the first step. But if you think let’s get dirty as you rub mud on your face, you’ll be the first one to go, and the first one to realize that dirty, hard work can actually be fun in its own sick way.

For more on embracing the imperfection of work and life in general, read my book, How to Be An Imperfectionist.

About the Author

I'm lazy, but you can call me Stephen. When you're as lazy as I am, you need superior strategies to live well. My strategies are so effective that I'm productive every single day. As the world tries to figure out how to always stay motivated, I create strategies that don't require it.