Even if you can push boulders up the hill, it doesn't mean you should. Even if you're strong enough to be Sisyphus, it doesn't mean that's what you should aspire to.

When you're looking for your day-to-day — your job, your work, or even just confirmation that the path you're on is the right one — ask yourself: am I pushing a boulder up a hill, or am I running downhill?

It's a heuristic for understanding where the energy in your life flows. Are things coming easefully, or do they require tremendous effort?

effort vs. chore

That's not to say you shouldn't work hard, or that every good thing should come easily. But you'll notice that when you put effort into something while running downhill, you go further, faster — and it's more fun. The challenge of pushing a boulder up a hill isn't just a challenge. It's a grueling chore. And sometimes we conflate the good things that come from a challenge with that Sisyphean task — pushing a boulder up only to watch it roll back down, repeating yourself in one form or another.

the best boulder pusher award

I experienced this firsthand.

For the past six months, I was in a role where I did well. Strong enough to push the boulder up the hill, over and over and over again. But honestly? I felt the stress of it on my body, on my mind, and I wasn't seeing the payoff. It's not like I won the Best Boulder Pusher award.

Here's the thing — I'm switching into a new role now. Not because of the work I was hired to do, but because of things I did outside my scope. Not above my responsibility, but literally beside it — complementary to it. I started building tools for my team, applications that helped people do their work better, while my actual job was customer-facing, post-sales work.

In the small amount of time I could dedicate to building tools, that effort had a completely outsized impact on the org. Every time I published an application for my team to use, I got tremendous recognition.

That was the signal. That's what running downhill looked like.

20x the work, none of the payoff

It took me a while to accept it. I had told myself, "I'm trying to succeed in this post-sales capacity. I want to grow here. I want to become a manager, a lead." I put easily 20x the effort into trying to do well at that — working 14-16 hour days, weekends — and I got no outsized recognition for it. I was performing well. I was respected. But the sheer amount of work I was putting in didn't lead to a promotion.

That burned. That hurt.

But it was a sign.

Spending a weekend building a tool got me praise, recognition, attention, and ultimately an entirely new role crafted for me — to focus on building exclusively. A switch to a team that's excited to have me. A raise.

That sounds like running downhill.

the heuristic

This whole journey has been a lesson in being a little less stubborn about fixed ideas — what success is, what a challenge is, what "following the energy" means. These experiences are reference points now. A heuristic I can come back to.

Am I pushing a boulder up a hill? Or am I running downhill?