Be Sincere—Not Serious

One of the best parts of working at a media company is seeing how the work we publish can change people’s lives. Our most recent hire, entrepreneur in residence Brandon Gell, had his life changed by the piece you are about to read (which we originally published last year). It was the key for him to find joy in his career. It may just do the same for you.—Evan Armstrong

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Back when I was a manager at a large corporation, I noticed myself alternating between two distinct states at work. Most of the time, work was fun. Even when I clocked long hours on challenging projects, I enjoyed myself and looked forward to doing it again the next day. 

Other times, I was a tightly wound ball of stress who sucked the joy out of a room like a dementor from Harry Potter. Even when my workload was lighter, things just felt difficult. Eventually, I realized the work itself wasn’t to blame—it was my attitude that was triggering one state or the other. For a long time, I wondered how to fix this problem.

I found an answer in the work of British philosopher and writer Alan Watts, who delivered the statement in a lecture: “I assume that maybe you are not serious, but sincere.” 

His words jumped out at me. I reflected on the difference between these two modes of being and something shifted. Suddenly, I had a new tool—a lens with which to identify whether a curious, playful approach to challenges might be more effective than tension and struggle. It turns out that you can’t be serious and sincere at the same time. Seriousness precludes sincerity.

For the most part, you’d be better served by being sincere rather than serious. Yet, in life, we often gravitate towards the reverse. Let’s dive into the difference between the two and find ways to help you access the life-changing magic of sincerity.

It’s just a ride

In his stand-up routine, American comedian Bill Hicks compares the world to a rollercoaster: "The world is like a ride at an amusement park, and when you choose to go on it you think it's real because that's how powerful our minds are. And the ride goes up and down and round and round. It has thrills and chills, and it's very brightly colored, and it's very loud."

Some people, he points out, recognize that life is "just a ride," while others seem strongly invested in it being, in some sense, real: "Look at my furrows of worry. Look at my big bank account and my family. This has to be real!” Hicks’s tone is stronger and more judgmental than I would use, but his point is clear: It's possible to get so caught up in the bells and whistles that you lose sight of the bigger picture. 

Imagine you're playing a board game with someone who takes the game too seriously. They’re trying to win and follow the rules to the letter. Eventually, they forget it is just a game that will end and that life goes on regardless of the outcome. When I play games too seriously, I don’t have much fun. Later, once the game is over, I worry that I ruined the fun for others. Being serious turns the game into a drag. Even if I technically “win,” it doesn’t feel that way in the end.

Consider the alternative stance, one in which you never lose awareness of the fact that it's just a game. This doesn't mean you can't be fully involved in the game itself, playing to the best of your ability and aiming for a particular outcome. That’s what it means to play sincerely—to be engrossed in the experience of the game without taking it too seriously. In my experience, that approach is a lot more fun for everyone involved.

Finite games are serious

In his book, Finite and Infinite Games, James Carse describes two kinds of “games” that we play: “A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play. Finite games are those instrumental activities—from sports to politics to wars—in which the participants obey rules, recognize boundaries, and announce winners and losers. The infinite game—there is only one—includes any authentic interaction…[that] exists solely for the purpose of continuing the game.”

Let’s say you’re angling for a promotion at work. On the face of it, this goal could be treated as a finite game, where there are rules and the expectation of a winner and losers. Indeed, many—if not most—people approach work as a series of finite games. 

But what if getting a promotion is merely a part of the infinite game of your career? How would you approach the promotion if your goal were to continue “playing” the game of a career you enjoy, rather than to “win” it? I’m not suggesting you should be any less ambitious or work less hard, just that you solve for long-term enjoyment instead of short-term rewards.

Outside of work, another expression of the infinite game is romantic partnership. What does “winning” even mean in that type of long-term context? You may well win the argument (the finite game) and risk or lose the relationship (the infinite game). 

This distinction between finite and infinite games maps well to the mindsets of seriousness and sincerity. A finite game, where the goal is to win, can easily become a serious, grave affair, devoid of fun and levity. An infinite game, where the goal is nothing more—or less—than to continue to play, lends itself to sincerity. Confusing an infinite game for a finite game can be a subtle source of suffering in life.

The point is not the end

When I introduce this distinction to people, some resist the idea that life should be treated as a game, since games can sometimes be seen as frivolous or childish (Carse’s more sophisticated framework aside). My intention here is not to imply that life is unimportant, nor do I want to suggest that it doesn’t involve intensely difficult challenges. 

If you are having trouble with the word “game," try substituting the metaphor of life as a game with life as a dance. Again, Watts got there first, when he said: “We thought of life by analogy with a journey, a pilgrimage, which had a serious purpose at the end, and the thing was to get to that end, success or whatever it is, maybe heaven after you’re dead. But we missed the point the whole way along. It was a musical thing, and you were supposed to sing or to dance while the music was being played.”

Think about the qualities a dance would take on if you were to approach it with seriousness. What would your body feel like? How much would you enjoy it? How fluidly would you move, and how responsive would you be to your partner, the music, and the crowd around you?

As with the board game, it might be easier to see the difference in approach by thinking about who you’d want to dance with. Would you prefer a dance partner who has a strong attachment to doing it perfectly and “winning,” or one with the capacity to flow with the music and the movement? 

You might be thinking: Isn’t it important to focus on getting good at things and doing them right? Doesn’t it imply letting go of standards and striving to achieve difficult things? 

It doesn’t—because all of that is still possible through sincerity. The difference between seriousness and sincerity is not how involved you are in the activities of your life, but in how tightly you grip. In fact, I would go even further still: Gripping less tightly can unlock better performance and with much less effort, as I’ve written about before. Simple activities, like playing catch, floating in a pool, or balancing on a beam, require the right amount of effort, but not too much. Otherwise, you start to get in your own way. 

Many non-physical things in life also benefit from commiting to the process without stressing about the outcome. Difficult conversations at work, parenting, writing, and other pursuits suffer when you prioritize the result (the finite game) over the process (the infinite game). If you can cultivate a sense of playfulness within the challenges of life, you might be surprised by what you can accomplish (in both the short and long term).

The best approach might feel silly 

Seriousness can get in the way of the most constructive course of action. Think of a meeting at work toward the end of the day. People are tired, and there are some difficult decisions to make. As Jonny Miller tells us, the best thing to do might be to ensure everyone’s nervous systems are well regulated—perhaps by taking a big physiological sigh, shaking your body, making some noise, or cracking some jokes. 

But, in a lot of professional contexts, those things might be regarded as silly. This attitude of “we don’t do that sort of thing around here” can be seen another way: as excessive attachment to the supposed rules of the game. This perspective can interfere with easier and more effective ways of working and living. 

Adopting a posture of sincerity helps you navigate this problem. If you can regard yourself and your situation with a sense of humor, you can embrace what may feel silly and remember the rules you’re following aren’t set in stone. That allows you to see through the limitations of the game you’re playing.  Playfulness makes it easier to adapt the rules of the game to meet everyone’s needs in the situation. You might decide to invent a new rule, change a rule—or play a new game altogether. 

You may now be wondering how to implement this idea, so I’ll leave you with these thoughts. 

Start small in your personal life before moving on to more challenging work contexts. I encourage you to tune into the experience of seriousness in your day-to-day life. What aspects feel tight, heavy, and constrained? In these areas, see if you can tune into any undercurrents of enjoyment. In the context of games, the way to let go of seriousness is to focus on just having fun. And the same applies in life.

Another approach is to consciously try to turn up the seriousness, to exaggerate it almost as if you were an actor performing in a comedy play. Go far over the top and see if your perspective shifts a little. Can you find some levity even in the depths of seriousness?

Finally, I’ll lean on the wisdom of the Stoics, who encouraged their adherents to meditate regularly on their own death, as illustrated in this short guided “death meditation” in the Stoic tradition. Memento mori is a powerful way to reestablish and maintain a sense of perspective if things are getting too heavy. You are going to die one day. Does this situation really require such seriousness? After all, the point of the dance of your life is not to get to the end but to enjoy the music along the way.

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Michael Ashcroft is a teacher of the Alexander Technique, a coach, and a writer with a background in energy technology innovation. You can read more of his work at michaelashcroft.org and expandingawareness.org.

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