Why Serious People Have More (and Better) Fun

James Walpole/ September 21, 2017

Tonight was a rare social outing for my very busy startup company’s team. We all climbed into a bus and drove to the nearby Braves stadium for a baseball game on this late summer night.

We’re a hardworking, serious bunch. When we’re in the office, we’re heads-down problem-solvers and experienced firefighters. We face down some fearful odds and challenges. All of us know how to take responsibility and get things done with few resources, with a little ingenuity, and with a lot hard work.

But tonight we got to bring out a, well, “different” side of our team dynamic.

We were cracking jokes. We were drinking (some of us more heavily than others) and dreaming about the future. We were taking selfies. We were telling jokes, sharing embarrassing stories, competing in feats of yoga and physical strength, singing along to “take me out to ball game,” dancing to music in the stands, passing popcorn amongst ourselves, and generally cutting up like children after a long day of work.

It’s not something we do every day, but this game refreshed my memory: my team is amazing. Any time can be special when you spend it with a group of people who are dedicated to building something great. Spending time outside of our normal work environment reminded me of that.

This experience my team had tonight also reinforces something important I’ve seen in my own life since entering the working world: as I assume more responsibility and put up with more s%^& in life, I become better able to really enjoy the fun moments of life as well.

Let me explain.

The Fun Narrative Is All Wrong

I’m relatively young (heck, many of us are) for the work I’m doing. Most people expect people my age to be having a lot of fun and “being young” – not trying to fill management roles at companies, not building my finances, not making my own way.

If I spent my time like many other 21 year-olds who are in college, I would (presumably) be partying every weekend and twice during the week. I’d be around my peers all the time. I wouldn’t be nearly so burdened with cares, and I probably also wouldn’t be thinking about more weighty things like a creative legacy or my career.

People who think this tend to think that you get to have less fun as you leave school, get older, and take on more responsibilities. I’ve found the opposite to be the case.

While I never went to college, I did live a pretty normal-ish (a big emphasis on the “ish”) teenage life. And I’ve never been more bitter, cynical, and stodgy as I was then. Back then my needs were fully provided by someone else, I spent all of my time around peers in high school (“the best days of your life!”), and I had very little responsibility outside of writing some papers, filling in some bubble-sheets, and sitting reasonably still in a desk for part of the day.

So why wasn’t I having the carefree fun that’s advertised so heavily to irresponsible youth?

Well, for starters, perhaps it’s only when you haven’t taken on the real responsibility of being a free person that you can afford to have a stick up your ass like I did. I would never have enjoyed a night like tonight because I was a snob who couldn’t cut loose. I was a snob because I considered myself awesome and superior without ever testing my own hypothesis – i.e. getting out into the world and doing something. I was a snob because I had never taken responsibility and seen how much gratitude I owe others for creating the world I live in.

When I did do fun things, my friends and I were often using our “fun” (sometimes questionably enjoyable – much group “fun” at this age is social posturing) to run away from responsibility. We were celebrating things we hadn’t earned, or celebrating for no reason at all.

Our fun was avoidance of our future, and in the back of our minds I think we knew it. That meant the things we did were stupider, the way we acted was less considerate, and the aftermath felt less satisfying.

“Fun You” Needs “Responsible You”

My relationship with fun definitely changed when I left school, moved to a new city, and got a job. I had to learn fast. I went from someone with few real cares to someone pretty much completely on my own two feet in little time. I had to “grow up,” and according to the theory of most people, I had to give up on “the best days of my life,” or at least life’s best fun moments.

It’s been three years, and I still have a long way to go toward “growing up”. But I continue find that the more I do embrace maturity and responsibility, the more childlike and playful I find myself becoming as well.

That primarily happens in the course of my work. I’ve been through layoffs, a capital raise, several product launches, and everything in between. All that has taught me to be harder, to be braver, to be more ruthless, to carry more weight and criticism and fear.


Through these experiences, I’ve also become funnier. I’ve stopped being a snob about so many things. I’ve become more adventurous. I’ve become more imaginative. I’ve become a far bigger presence at parties. I’ve even pretty much made the switch from introversion to extraversion in just the time since I started at my current company.

That’s given me everything I’ve needed to enjoy a night like tonight and the other times – even if they’re just occasional – that I get to be a young person having a good time.

Now, when I have fun, I’m not (as I did in high school) using to pleasure to run away from the responsibility of life. Our pleasure is a way of running toward a full, responsible life. Our fun keeps company with our challenges, duties, doubts, and ambitions. There is no contradiction. In fact, our ability to enjoy the night was made deeper and more meaningful by the fact that we had worked so hard for it.

Ayn Rand wrote something along these lines in Atlas Shrugged. Her protagonist Dagny Taggart was born a CEO but (briefly) forced into the debutante mold. There she met the same ideas of irresponsible, immature enjoyment that I’m calling out:

“It’s just a thought that disturbs me once in a while….I thought about my first ball….I keep thinking that parties are intended to be celebrations and celebrations should be only for those who have something to celebrate.”

“Celebrations should be only for those who have something to celebrate.”

In the book, Dagny remembers this after she has achieved a goal that took months of excruciating mental work. If you read the book, you’ll understand what intense stress and responsibility she takes on to do it. It’s no walk in the park, and it’s no frat party either. But at the end, she has something to celebrate, and she can celebrate more cleanly and more fully because she made her sacrifices to get what she wanted.

So did we. We had something to celebrate tonight. And in my good days, that’s what drives the amazing, fun experiences I get to have.

The real deep kinds of fun and pleasure come with the rewarding feeling of knowing that I have not lied to the world or myself to achieve it. The pleasure is better because I know that I achieved it, and that I created the conditions necessary for enjoying it. I can pour all of my youthful enthusiasm into enjoyment of the things I’ve created and I’ve earned, without being ignorant of what it took for those beautiful, good things to exist.

Hopefully now you see the power of this paradox. The serious and the fun belong hand in hand. Only the truly serious can have fun in the truest sense.

Perhaps another time we’ll talk about why only the truly jolly (fellow belly-laughers of the world, unite!) can be truly serious.

James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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