Can anything easy and fun be worthwhile?

My reaction to 'easy and fun' used to be something like disgust, or revulsion, with a strong undercurrent of disbelief and just a whiff of admiration

Art by Stephanie Davidson

There is a wonderful concert festival in San Francisco’s Golden Gate Park each year called Hardly Strictly Bluegrass. As the name suggests, the event has bluegrass as well as all kinds of adjacent music. It always happens on a flawlessly sunny day in early October, and it’s completely free. There are no fences around the venue, no check-in lines, no restrictions on bringing your own food, just a stream of San Franciscans of all ages dragging wagons and folding chairs to the park to listen to some good music. I have loved this event since I first went in 2014; it represents a free community-feeling celebration of the likes I rarely see these days.

The festival is free thanks to billionaire Warren Hellman, who founded and funded the festival during his life, and whose estate has picked up the tab since his death in 2011. Needless to say, this man was extraordinarily rich. One year at the festival, I stumbled across an exhibit honoring the founder/funder, and, curious about who he was, I skimmed the poster boards documenting his life. He was a banker and investor…blah blah…and then a pull quote stopped me in my tracks. It was Hellman saying something along the lines of:

“I only do things that are easy and fun.”

Now, big caveat, I may have completely misremembered this, it was a long time ago and I was certainly tipsy on sunlight and beer at the time. But that doesn’t matter for our purpose, because I thought the quote said, I only do things that are easy and fun, and it stopped me in my tracks. My reaction to that statement was something like disgust, or revulsion, with a strong undercurrent of disbelief and just a whiff of admiration. Easy and fun?

Reading this clarified for me a long-held belief: that anything I could ever describe as “easy and fun” certainly must not be worthwhile, by virtue of being easy and fun. Worthwhile things are hard and require struggle, full stop. Not to mention the fact that so many people have almost no room at all for easy and fun, so a billionaire saying that he operates only in that world seems both a bit icky and completely out of reach.

Hard and miserable

I have thought about this many times since I saw this quote in my mid-twenties. I thought about it while I was running my startup, a job that was almost never easy and fun, or anything close. Where did my aversion to these words come from? Why is it that I automatically correlate difficulty and misery with activities worth doing?

School

I can’t help but think that my education had something to do with this. As I’ve written about before, I went to all-girls private school, an education that gave me some of my greatest gifts and also saddled me with some of my greatest struggles. I learned to write there, and I learned to love writing. I also learned that being perfect is the goal, that there is a right way to do things in order to deliver perfection, and that prestige is paramount.

Studying was always a strength of mine, but it was rarely fun. I often did not make academic and extracurricular choices driven by my interests, but rather by calculation: what would be best for my resume, what would get me ahead. My senior year I took AP physics, a subject that did not interest me, and I was on the school disciplinary committee—I think everyone can agree that decision could have only been resume-driven, because nothing about that sounds easy or fun at all. But worthwhile…yes, maybe? I was learning? I was demonstrating leadership? It was a combination of my innate traits and my school context that really honed my ability to do hard, unfun things well, even really well.

Work

My first job was at McKinsey & Company, the crème de la crème of jobs for Ivy Leaguers in 2010. I had done it. I had worked and worked, and I had shown that I could get the best thing, whatever that thing was. McKinsey only deepened my skills in the hard/miserable area. I was more unhappy doing work there than I ever had been in school, but since I had never failed yet to deliver the goods, I refused to fail in this context either. I would prove to myself and to them that I could do it. Everyone around me thought this job was the best, so it must be. My subsequent journey starting a company in Silicon Valley followed the same general arc, but was arguably even less fun and more miserable at many points. It took a massive toll, but it seems by then my pattern was set.

I just expected anything that mattered to be hard and miserable.

What if…

After I left my startup career, I thought about this question of whether to prioritize “easy and fun” a lot. I still remembered the (alleged) Hellman quote all those years later, and it still niggled at me. Do I want to continue down the hard/miserable path, according to a belief that this is how one does worthwhile things? This also seems like a very worthy inquiry as I begin my parenting journey and (doubtlessly) pass on my beliefs about what matters, at least a little. It’s also related to managing chronic illness, which mandates certain lifestyle changes. What would life be like if the adjectives easy and fun did not make me tsk with disgust and look around for some other activity?

Now, I certainly cannot not stomach an approach that prioritizes only easy and fun and nothing else, that is too far from my whole history of decisions. It also feels a little too Warren Hellman, billionaire—who else in this world can really prioritize easy and fun all the time and make life work?

But, then again, given how far I’ve gone in the opposite direction, what would it be like to bring those two adjectives into my calculation even a little?

Starting to practice easy and fun

Just the other week, my friend

Alex Dobrenko`

and I tested out the idea of recording a conversation and publishing the audio. We talk every Friday anyways, and the recorded conversation went very much like our normal Friday conversation, batting around ideas, with just a bit more performance. We talked for 30 minutes and then turned off the recording. Alex noted that he would have gone much longer, because he never feels like he’s done enough. I said that the whole thing seemed way too easy and fun. We both have our hangups.

But actually, the conversation also felt good and worthwhile. So, very possibly, it was good, and worthwhile, and easy and fun. I am still in disbelief that this combination exists. But in many ways, I think the easy and fun feeling is my physiological and psychological reaction to an activity that’s actually just a really good fit for me.

Talking about ideas. With someone I like and trust and enjoy. That’s kind of my jam. And so following this easy/fun instinct in this case seems really smart, savvy even.

The same goes for my relationship with The Lady’s Illness Library. While I don’t think it would be right to categorize talking about chronic illness as “fun,” I would describe the conversations as generally easeful, energizing, and very often enjoyable. After I did the first couple of them, it was this observation that made me certain I would keep going. I have described the project as “having its own momentum,” and “having a special energy,” and I think both of these are related to the fact that I have found a project that’s a good fit for me.

So I’m going to continue pushing on the easy and fun frontier. I am going to continue trying to quiet the voice telling me that anything easy and fun is just a luxury, just a waste of time, just privilege, whatever is the self-shaming word of the day. While I don’t think I’ll ever want to pull a full Warren Hellman, (if he actually even said this, if not, my sincerest apologies and thanks for being a wonderful foil, Warren), I do want to continue the inquiry and see how far I can comfortably take it.

✍️ I’m curious…

What have you done lately that was easy and fun, or had a “special energy” to it?

What have you done lately that was neither easy nor fun, but felt satisfying anyway?

What is something hard and miserable that you’ve given up for good