Skipping Steps

December 11, 2023

UM Thanks to DALLE-3.

One thing I notice in people who haven’t accepted who they really are is a desire to skip steps.

I know several tech workers a few years out of uni who dream of being a General Partner at a VC firm. A friend’s flatmate had a poster on his wall that said Wake me up when I’m CEO. There’s a certain type of guy who wants to be a founder”.

I think I went through the ultimate version of this in my final year of uni: I wanted to work in private equity. Imagine parachuting into the management team of a company as a twentysomething, getting to figure out who to hire and who to fire, and what would drive value—not to mention making shitloads of money. Sounds amazing!

The problem? Like most twentysomethings, I didn’t understand the first thing about business. I literally failed 20 case study interviews at consulting companies—which are a pitiful simulation of real business problems. If I couldn’t even pass case studies, why did I think I’d be able to hire and inspire a team of people? I was so naive I didn’t even consider that would be part of the job.

The thought that the fun” of managing a business would comingle with the anxiety of having to manage real people: with families, and illnesses, and bereavements and all the shades of grey in peoples’ real lives never occurred to me.

I saw only the external status of the role—making money, fancy articles in the newspaper, people oohing” and ahhing” when you say what you do at parties—and not the actual role, which is hiring and firing people, dealing with legalistic and bureaucratic bullshit, and staying up until 3am figuring out why your excel model broke. There’s not much glamour in that.

The desire to skip steps comes from insecurity. You see someone successful and you think the only way you’ll feel OK is if you’re successful just like them. And since you want to feel OK, you want to skip steps to get there as fast as possible.

But skipping steps won’t lead you to success. And being just like your idol won’t make you feel OK. In fact, if it were possible for you to skip steps and end up where you wish you were, I bet you’d feel even more anxious than you already do.

A friend of mine is a notorious step-skipper.

At rugby practice he gives teammates unsolicited feedback on their pass, when he can’t hit a standing player from 10 metres away. He’s trying to steal the clout of the coach without having actually earned it through his actions. Even when he’s right, people find it annoying when he opines. He hasn’t earned their respect through doing the reps himself.

Our coach was ill one day and couldn’t train, so we put my friend in the role to run practice. It was awful. He couldn’t command the attention of one teammate, let alone 15. And it showed—people ignored him, the practice collapsed, and we started playing pick-up instead.

My friend was furious that people had disrespected him. But deep down I think he was furious because he knew he hadn’t done enough to earn his teammates’ respect. He skipped steps.

If you want to skip ahead to a role that seems far above your station, ask yourself why. If it’s because you think it might make you feel better about yourself, perhaps you should reconsider why you’re doing what you’re doing.

To get the role you seek, and the trappings of status that come with it, you have to earn it the hard way. As a Venture Capitalist, you can’t persuade founders to take your money if you can’t demonstrate to them that you know how to help them build a company. You can’t persuade a team of rugby players to respect you if you can’t pass the ball properly. You can’t be the founder” of a successful business without first starting a terrible business with no employees, no customers, and no revenue.

The only way to be able to truly inspire people—to be incredible at those high-status, higher level steps—is to have mastered every lower level step. This gives you the confidence you need to know you belong right where you are.

Every job in the world is a grind to most people—the secret to a full life is to find the work that feels effortless to you but looks like chewing glass to everyone else.

Once of the secrets to success is not to idolize players a few steps ahead of you—it’s to fall in love with the game you’re playing right now.