Doubling down

“You gotta wear the saddle if you wanna get the apple but you can't enjoy the apple if you only wear the saddle.” - Brendan Milburn & Valerie Vigoda (Image by rihaij)

I have a tendency to slow down when things are going well.

It as though I’m heading off the highway and into a small, sleepy town. I have the sense that I’ve arrived at my destination. It’s 25 mph here, not 70. I wind through the streets, slowly taking turn after familiar turn.

That’s fine if I’m actually there. But more often than not, I’m not. I’m slowing down and exiting when I still have miles and miles to go.

I’m not sure exactly where this came from. Maybe I learned it as the eldest of four, giving myself a handicap when playing games with my younger siblings.

Maybe I learned it in sixth grade, when a scornful classmate told me I didn’t always have to raise my hand to answer questions.

Maybe it arose out of self-consciousness about how deeply I get into something when I first begin it, from guitar to knitting to entrepreneurship.

Or maybe it was a coping skill from my first years as an employer, ensuring that I never made more money than the peers I was hiring to teach music at my school.

Wherever this habit originated, it is persistent. When I first became aware of it just a few years ago, I took up tennis in order to strengthen my competitive spirit and get more comfortable playing to win.

Now, I’m finding a lot more opportunities to practice this type of thing in real life. During most of the pandemic, opportunities for winning have been scarce, but now that we’re emerging to the other side of that, I’m seeing some pockets of success. And instead of slowing down, whether by deliberately sabotaging myself or by getting distracted, I’m doubling down.

What does this mean? Well, in Blackjack it means to double your initial bid in exchange for one more card. In other words, you’re taking on an additional risk.

But in real life, if something is working well, putting additional effort into it isn’t so risky. It’s probably wise. What have I been doing all these years?

It’s incredible how good my brain has become at tricking me into diverting my attention away from potential success. I’m always beginning another project once my initial project is showing some good progress. Or I wait too long to follow up on a lead, or I take a break like the hare in the Aesop fable.

Seeing a pattern like this goes a long way toward correcting it. If I know that I have tendency to do a certain thing and I don’t want to do it anymore, I can be vigilant in looking for instances of this behavior and consciously do something different — like doubling down.

So even as I begin casting about for the next thing and the next thing that I want to do down the road, I’m challenging myself to stay focused. I want to see what happens if I put even more effort into doing the thing that’s working, as opposed to giving into external or internal pressure to back off.

It feels weird. It feels uncomfortable. By now, I know that these are feelings that indicate that growth is happening. There’s another reason to keep leaning into the work.

Doing things differently will take me to a different place. I’m not going to be rolling around that first small town off the highway. It may be nice enough, but it wasn’t where I was going. I don’t have to settle there. I want to see what life is like in that other place, farther up the road, that I feel called to go.

Have you ever experienced this temptation to self-sabotage? How have you handled it? I’d love to hear your story.