Hey B, How Can I Have Fun Again?

I feel so guilty being unproductive that I can’t enjoy myself.

Hey B,

Often, when I’m doing an activity that doesn’t lead to a better future outcome (i.e. playing a board game or attending an event vs. studying or basically anything useful) it feels like I’m wasting time, and it makes me not enjoy what I’m doing. This is super lame — especially since I imagine that many (if not all) top performers across most activities aren’t concentrating on future outcomes, but are enjoying what they’re doing.

This is maybe two questions: “How does one get lost in what they are doing?” and “What can I do to enjoy things that are un-fruitful?”

In Search of Blissful Boredom

Hey Bored,

I know this feeling all too well.

I remember not so long ago going to my partner and saying, “Hey, um, I need to do something for fun.” He said, “Great, yeah, you should do that!” And I said, “Awesome… what do I like to do for fun?”

So lame.

If only I had had the self-awareness then that you demonstrate in your letter, dear friend. Because of course, it’s not that I was lame for not knowing what I like to do for fun. It’s that I was too paralyzed with angst to get enjoyment out of much of anything — except work, of course. I’ve always enjoyed successfully doing things I’ve deemed “useful” or “fruitful”.

But how do we deem these things as such? How do you know if something does or doesn’t “lead to a better future outcome”? Are you a fortune teller? If you were, I am confident you wouldn’t feel so paralyzed, because you would know exactly what steps you need to take today to have a fulfilling future.

It seems to me that you’ve got an obsessive genius in your head, and he’s popping adderalls even in his off hours in order to solve an equation about the future. Unfortunately, the givens of this problem are incomplete, and the equation is therefore unsolvable. This genius will cover all the walls of your mind with facts and figures if you let him. And he will never get anywhere. The equation won’t be solved until the future arrives. Because only in the future will all the givens finally be clear. But when the future arrives, the genius in your head will already be off to the next future equation, not leaving any room for you, dear friend, to enjoy or make good decisions in the present.

So how do you tell the genius in your head to give it a fucking rest? How do you slow down these thoughts — these fears of future failure, these conceptual judgments about what a productive life looks like? Here, we’ll turn to the genius Ludwig Wittgenstein for wisdom:

“A man will be imprisoned in a room with a door that is unlocked and opens inwards as long as it does not occur to him to pull rather than push.”

We all innocently do the best we can with the information we have, until we get new information, and do something else. When we come to fully realize that something doesn’t serve us, we stop doing it.

Dear friend, when you fully come to see — deep in your bones — that you cannot solve the future using the information you have in the present, you’ll have a lot more room in your head to enjoy yourself. And you are only one moment of calm, one distraction, one insight away from seeing this. You could see it right now. And it could change everything.

Paradoxically yet wonderfully, once you do see it, you’ll have a lot more clarity to see the opportunities right in front of you that could put you on the productive path you know deep down you were designed to walk — things like the sign that says,“PULL”.

And most blissfully of all, while the genius in your head is taking a much needed vacation, I think you’ll find there isn’t much of a line between “fruitful” and “un-fruitful” after all.


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Brooke is a mentor, writer, and facilitator. She teaches clarity to creatives — helping you gain greater access to your own best ideas so you can start doing all the awesome sh*t you were born to do.

You can find her writing weekly here on Medium and at brookebishop.com. Click the if you like what you see, and sign up for weekly updates using the form below.