Lessons to my younger self (and other young people today)

Sam Gerstenzang
3 min readJan 1, 2019

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One of the challenges of being young is you don’t know what excellence looks like — you just don’t have the reps to know. So you should make it a priority to shortcut those reps in any way you can— read the books, find the people, look at the work. Over and over again.

Learning from failure is overvalued. Understanding success and more importantly, why it was successful, will create a useful mental model to jump off from.

But equally important to understanding excellence is not to be paralyzed by it. You have to just do — while being constantly aware of the gap between excellence and your work.

This is enormously difficult because fear gets in the way. Will I ever be able to achieve excellence? Am I enough? Self-sabotage sets in at this stage — if you never try you’ll never have to witness the valley of inferiority.

You must overcome by separating your ego from your work– your work is not you.

Most young people fail because they 1) don’t understand what excellence looks like, 2) don’t do the work (due to fear, laziness, or disinterest) or 3) don’t have the skill. You can only control parts 1 and 2, and if you solve those, you may solve part 3.

Above all — do the work. Even– especially — outside of work. You don’t know enough to do the job well just during work hours. And do the work that you say you’re going to do — that alone will differentiate you.

But mastering skills is only one part of your evolution. “Experience” has three components:

  1. Ability to predict future outcomes, usually based on past data

To predict future outcomes better, you need data (again — read, listen, watch– and find shortcuts to do so) and to constantly try to understand why.

Predicting outcomes allow you to make better decisions today. Be mindful to pay attention to whether the decision at the time was the right one — ignore the result itself — only look at the decision process.

One of the advantages of being young is you have not yet learned lessons that are wrong. You are less likely to be an average of your experience, and much more likely to spike in ways that others won’t. This is a huge advantage of the young — and those who age well are often good as good at forgetting earlier lessons as they are at applying them.

2. Behavioral — do you know how to act? How to run a meeting properly, how to make sure deadlines are met, etc.

To learn good behavior, models are once again, helpful. Learning good behavior is best learnt from other people — find good people to spend time with — in and outside of work. In the absence of direct experience, I’d suggest watching The Defiant Ones as a place to start.

Confidence is another strange thing in young people — I see young people way too confident and way too unconfident. Confidence is like compensation — some people have too much, some people have too little — and no one has precisely what they deserve. I’m not sure about you in particular — but the right mix probably looks something like a belief you have to paddle hard to be in the room you deserve to be in.

Find people who will answer your questions graciously, and pay them back with loyalty. (Thank you.)

3. Emotional control — how do you act, really?

To learn good emotional control will take your lifetime, and everyone will require a different journey. My personal toolkit is as follows:

  1. Read The Wise Heart by Jack Kornfield, and The Power of Now by Eckhart Tolle.
  2. Log every extreme emotion you have, as close to the occurrence as possible. Use this log for step 3.
  3. Find a coach or therapist you jell with. It’s a highly leveraged way to accelerate your emotional development.

How do you seek advice?

One mistake I’ve seen when younger people ask me for advice is that they ask either a) things I can’t possibly answer or b) questions already well answered. For example, “I’m a generic smart person but without deep skills. What should I do?”

That’s a difficult question to answer. I’d suggest you seek to ask a different question: “Here’s what I know. What am I missing?”

This requires more preparation on your part — to understand what you know — but provides a more fruitful answer. Most advice of the variety “here’s what you should do” is not very useful. But providing a window in to what is unseen can shift your world.

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Sam Gerstenzang

Building @askumbrella. Previously building products, teams, and companies at @sidewalklabs & @imgur, investing at @a16z http://samgerstenzang.com