It’s Okay if Your Work Feels Like Play

Last night I was out for a walk with daylight savings time. It means finally I can go for evening walks around seven or 08:00 p.m. Here in Minneapolis. And there’s still a little bit of light out. And it’s gorgeous. It’s beautiful. There’s this incredible weather. It must have been like, in the low 60s.

Absolutely gorgeous. Now, when I. When I like to go for multiple walks throughout the day. But from this particular walk, I was working on sketching out the outline to a new speech that I’ll be giving next month at the best ever conference. And I was out there for an hour just walking this beautiful riverfront path right next to what’s called the Stone arch bridge. It’s absolutely lovely. And just in my own world, creating this speech in my mind and the outline for it, and I blinked. It felt like.
And I looked up and suddenly an entire hour had gone by, and I was like, wow, that was crazy. That was really cool. But it elicited a thought, which was, wow, that felt like play. I’m doing work right now. The work I’m doing is I’m crafting a speech that I will deliver to a couple thousand people. And that’s very high leverage, high value work. But it felt really easy. It felt like play in that moment.

And this gave birth to a particular weird reaction that I noticed in myself over the years. And I want to share it with you in case this is something that you resonate with. And maybe knowing that you’re not alone on this will bring you a little bit of value, is that the work you are most called to do is unlikely to feel like actual work. It’s going to feel like play. And this can paradoxically make you feel guilty, like maybe you aren’t actually doing work. Maybe you’re not being productive because it feels so easy. You look at your time spent and you’re like, oh, that was nothing. And other people might tell you, you’re so great at this, and you’re like, it’s no big deal, right? You look at your gifts, at your strengths, and the work feels light, it feels easy.

And so it doesn’t almost feel like you did anything, doesn’t feel like you did any work. And you’ll look back at the end of your day and think, was I productive? Was I effective? I see the rest of my team working, and I feel like I’m not doing anything helpful, especially if you’re the visionary in a company, this can be very difficult because you’re the one that’s setting the strategic vision, you’re setting the path and saying, this is where we’re going. And that does not. A lot of the time when you’re thinking you need to make space to not really do anything productive. You need to just go and wander and let your mind simmer. And you’re doing a whole lot of things that aren’t producing something tangible. And as a result, this can make you feel like you’re not meaningfully providing to the helping out the team. And so the trap that I’ve fallen into over the years is then that means I start filling up my calendar with hard things, things that I don’t like doing, things that I hate doing, just so it will feel hard and therefore I will feel productive.

It’s almost like self sabotaging myself. But when you play the games that you’re designed to win, the game gets easy, and that’s the point. So don’t self sabotage yourself. Here’s the interesting balance that we all have to find, is that as an entrepreneur, especially in the early days, if you’re a solopreneur, you don’t have a big team that you have surrounding you. You’re going to have to do the things that you both like, and you’re going to have to do a lot of things that you don’t like. So in the beginning, you will feel productive because you’re doing a lot of things that you don’t like to do. And then over time, as you start to grow and you learn how delegate and you start to bring on team, now you’re going to be hiring around the things that you suck at, which are probably the things that you found hard and heavy. And it’s leaving more time for you to do the things that you’re good at.

And the really interesting paradox here is as you start to find success in this way, you will feel like you are doing less and less and less. And that can be a real mind fuck. Truly, I share that because this is something that I really struggle with over the last five years in all my businesses. Whether that’s escape climbing, that’s invictus capital, that’s my personal brand. Everything that I love doing feels easy. My strengths, like this podcast, this doesn’t feel very hard to me. Sitting down and writing out a speech and practicing and rehearsing it, rehearsing it, rehearsing it. That doesn’t feel hard to me in the same way that sitting down in a meeting for an hour feels incredibly difficult.

And yet, when I leave at the end of the day, that hour meeting will make me feel like I did something, because I’ll feel exhausted, I will feel tired from it, and I’ll think, oh, therefore, I must have done good work, whereas when I spend hours writing, I don’t necessarily feel tired afterwards. And so I think, oh, I must not have done anything. And that’s not true. In fact, I spent that time doing the most high leverage, most high impact activities that I could. So don’t make the mistake of equating difficulty with productivity. Now, again, going back to those who are at the beginning of the journey, you don’t necessarily have this problem quite yet, because you have to do everything simultaneously, and you might need to force yourself through discipline to go and do those hard things. Later on, you start to do them as almost like an escape mechanism, so that you can feel like you’re being a meaningful, productive member of the team. So I wanted to share that with you, because maybe it resonates and it can save you from falling into a similar trap that I’ve fallen into over the years, which is kind of self sabotage myself and make myself do the things that I hate just so I can feel productive.

When the reality is the things that I love doing, those are the things that I’m most suited for. They feel like play, and those are the things that I should be focusing on. So hope this brings you a little of value. If it did, let me know. If it didn’t, let me know that too. I appreciate any and all feedback you can give. It helps us grow the podcast by helping us improve, and that’s going to do it for me. We’ll catch you in the next episode, but until then, stay hyper focused, my friends.