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Best Early Career Advice
DW #126 🟡

The best early career advice I ever got came from my first boss out of college over a beer after work. It wasn’t profound, it was brutally simple, and I think about it often:
simple career growth model:
ask questions,
say yes to uncomfortable growth opportunities,
make your boss look good,
be the first one in and/or the last one to leave— Ramsey Shaffer (@RamseyShaffer)
7:24 PM • Sep 12, 2025
1) Ask good questions - many young people are too scared (maybe too proud?) to ask questions. But naivety is a gift, if you don’t ask you don’t learn. To get good at anything you need to dig down to the first principles, find out the why behind the thing. You should ask your boss the why behind decisions, try to figure out the context you’re missing, learn lessons from past failure. This shows you’re thinking, not just executing.
2) Say yes to uncomfy things - you speedrun growth this way. It’s the old ‘no growth in the comfort zone, no comfort in the growth zone’ thing. Discomfort is the price of admission to everything worth having. You will build character, you will stand out, and you will learn even more this way. It may feel cringe, it may feel scary, and the most valuable thing you can learn is how to past those feelings early in your career.
3) Follow through on the things you say you’ll do - in other words, own your shit. It sounds obvious until you realize how rare it is. This is the corollary to #2, if you are going to take on uncomfortable opportunities, you have to deliver. Talk is cheap baby, execution is where you make your hay. This is where you build a reputation, and next to learning how to learn, your reputation is the most important thing to develop early. Do what you say, when you say you’ll do it.
4) Be the first one in, last one to leave - not about grinding for grinding’s sake or any of this 996 bs. Its about being present when important conversations happen, being where the action is. The best ability is availability. You can’t watch what you’re not around to see. Make this a habit and get it in while you can before you have all the other adulthood responsibilities of family / mortgage / etc. Becoming reliable is a skill to cultivate.
5) Make your boss look good - speaking of reliability, the way to the top is to reliably make the top brass look good. If you’ve ever read Robert Greene’s 48 laws of power, this is his #1 - never outshine the master. Their successis your success. Their problems become your problems. The best hack is making the person above you genuinely excited to have you on their team.
My favorite part of this advice is when you realize that none of it requires exceptional talent or connections. It’s all simply about showing up and doing what many believe is too simple to be effective.
People love to overcomplicate things, in reality 80% of success is owed to embodying the core tenants and getting really good at them.
The fundamentals never change - when you’re 22 in your first job or building your own company. Success isn’t complicated it’s just uncommon.
There’s no such thing as adults. There’s no such thing as experts. Everything is designed by people no smarter than you. Courage is in shorter supply than genius.
Do the work!
Peace,
Ramsey