Letting Go

Wakeboarding

The way wakeboarding works is you’re on a surfboard (or anything really) and you have to hold on to a rope that’s tied to a boat, that drags you around the waterbody. You enjoy floating on the water, kind of flying, kind of surfing, kind of holding on for dear life, but definitely having a great time as the wind kisses your cheeks and goes through your hair. So holding on to the rope is critical, right?

Wrong.

Learning to let go is the critical lesson. If you fall into the water, and you don’t IMMEDIATELY let go of the rope, you will die because you would have lost the support of the surfboard, but you’d be holding on to the rope which is still tied to the boat that’s going at a crazy speed. You’ll be waterboarding yourself and pretty soon your lungs will have filled up with water and it will be a very painful end.

Most of life works similarly. Especially entrepreneurship, and often relationships (platonic and romantic both). Maybe other aspects of life too, but I’ll focus on these two for now.

There is a plethora of research on why startups and founders should truly fail fast, learn fast and be agile, but the reality is, it’s remarkably difficult to implement that. I cannot speak for everyone, but a huge learning curve for me has been to detach myself from the project I’m doing. Probably the fastest self sabotaging thing I’ve done as a founder is to get so emotionally invested in what I’m doing that I blur the lines between “it” and my identity. My work becomes an extension of me, and that is a terrible idea because then any critique of my work becomes a critique of me. This mindset also meant that any failure of the project meant that I had failed. And nobody wants to be a failure.

So what did I do? I kept holding onto the rope till the water drowned me. Relationships deteriorated; the repair work for which was harder than building them in the first place (taking responsibility for your actions is harder than you’d think!). My mental health - went lower than the deepest part of ocean, which meant neither I, nor those around me were having a good time.

I’ve seen similar patterns in relationships both romantic and platonic. Recently, I’ve been hearing from so many of my friends about how they hate the situations they’re in. They don’t actually enjoy their “friend” group or the people they are around, but they still hold on to them out of fear of missing out, or to avoid the discomfort of putting themselves out there and investing in building new friendships from scratch. No amount of rationality gets them to see their own fault or the abuse they’re going through, until they breakdown and someone else needs to step in to help them.

I know it’s scary to let go of things, but I’ve rarely seen others or myself be happy sticking onto people and ideas that are not reciprocating efforts or producing results. But the longer you hold on to the rope, the worse it gets. It is always harder to get out of a toxic friendship or relationship 5 years into it than a few months into it. Similarly it’s much easier to bear loses of a few thousand dollars on a project instead of a few million dollars.

Obviously, I’m not making a case for not committing to anything. I’m making an assumption that you’re reasonable enough to both identify and work on your own shortcomings, and on realizing when your relationship or company is just going through a rough patch that requires you to pass the test of time compared to when you need to pull the plug.

Recognizing when to let go of a project, person, idea, venture, heck even a class, is a life skill. You’re not failing at something. You’re saving your life. But more importantly, you’re letting go of a poisonous vine, to a make space for you to go on to do better things, and be with better people.