There are generally two hurdles to overcome when you’re trying to Do The Thing:

1. Getting started
2. Keeping at it (without burning out)

It’s easier to start Doing The Thing if you have an idea you’re excited about, an idea that sounds Fun to you.

Similarly, once you’ve started, it’s easier to keep Doing The Thing if the process is Fun. If the grind is Fun.

This is, I think, what’s actually at the core of the popular quote: “Choose a job you love, and you will never have to work a day in your life.”

If I could do a Find-And-Replace of this quote in people’s minds to try and reframe it, I might pick something like: “Choose a job you love, and your time spent working hard will fly by.” Because it’s not that your life suddenly becomes easy or wholly pleasurable if you find a job you love. In fact, it’s the opposite; if you love what you do, you’ll probably end up working incredibly hard at it. Because you want to. You’re still grinding, it’s just that the grind is kinda fun, too.

I like how Ava describes it in her blog post about how making things is hard:

“Making things is hard and I feel like that’s the most useful thing to say about it. You have to try to be consistent, you have to practice constantly, you have to read, and you can’t make yourself be interested in topics you aren’t interested in. And you have to accept that it’s always going to be challenging. … I think this is because most of making things is just being perpetually stuck in the long middle.” (emphasis mine)

(Actually, just go read the whole thing immediately as it’s great and I absolutely cannot do it justice here.)

Making things is hard, and a lot of the process is just taking step after step and pushing through the long middle. BUT if the grind is fun, it makes taking each step a little bit easier.

So what does this look like? What does a “fun grind” feel like? Well, the annoying answer is that you have to figure this out for yourself, develop your own sense for it. Kind of exactly like when a recipe tells you to “salt to taste”.

That’s what I’m chasing now. And if you’re anything like me, then you might have to navigate through an internal storm of competing desires of what to do, to find what you actually really want to do. Competing desires include:

• What you like to do
• What you feel like you should do
• What you do because it gives you a feeling of improvement or progress
• What you do to be like the people you admire
• What you do because it’s in opposition to something you despise
• etc.

All easily identifiable as (read: mistakable for) Fun, at least early on to the untrained eye.

But over time and with more experience you inch closer and closer to feeling and knowing what you actually enjoy, from a place of true Fun.

Ideally you check in with yourself regularly to see if you actually still like the thing you are doing. How does your long middle look for you? How does it feel right now? In your work, in your hobbies, in your relationships. If things continue as they are for another year, or another three years, how does that prospect make you feel?¹