Working at a startup in your 20s? Read this.
Congrats, you are the youngest at your startup… Now what?
You are a young graduate or a dropout maverick. Your family warned you about taking this job. “Go get some corporate experience”, they said. Startups are brutal, how will you survive with no training? Still, this is your first rodeo and you can’t be more excited. After all, aren’t startups supposed to be fun?
Well, yes. But, just like a rollercoaster ride, you want to make sure you are safely strapped to enjoy it. Otherwise it can turn into a nightmare pretty quickly (startups fire ~25% of their employees within their first year on average). Before diving in, here are a couple of tips to help set you up for success.
1. Build Leverage
You grew up with an iPad and YouTube, that’s a superpower. From games, TikTok to Discord, there’s something you just learn faster than others. This doesn’t mean you should only take these “Gen Z jobs”, it means you can pull insights into your work that no one else sees. This is leverage. New to Figma? TikTok tutorials will get you set up in no time. Learning web3? You will find all the alpha Discords before others do. It takes you 10 mins to make an Instagram Reel while McKinsey analysts spend weeks understanding what “short-form video content” is. Don’t take the things you are good at for granted. You consume and synthesize information differently, use this to your advantage.
2. Learn or Earn
You are young and have a career ahead of you. Whether it’s building your own startup or working at someone else’s, make sure you are either learning or earning. Ask yourself when you feel stuck: am I going somewhere? If the answer isn’t obvious, you should re-evaluate how you are spending your time. Remember, you can’t afford to get stuck. Upgrading your skills allows you to productize yourself and be ready for the right opportunities later in your career. Earning or owning equity in a business unlocks life choices through achieving financial freedom. Both make you competitive. If you aren’t doing either, quit your job and work on something else.
3. Harass for Feedback
Here’s a guess: you are a 20-something working with a bunch of 30-year-olds, you are most likely shy about asking for feedback. In fact, you worry about being perceived as incompetent for almost everything you do (including being funny on Slack). Stop doing this, it is one of the most harmful things you can do to your career. No one hires 20-year-olds without conviction and a plan. Your manager is dying for you to talk to them about what you want to get good at. They have all the resources and want to train you, but they can’t do it unless you tell them you want to grow. Know that at a startup, your training is coming out of someone’s personal time. No one has a responsibility to babysit you if you don’t talk. Whatever you want, ask for it loudly and repeatedly. Never, ever, be apologetic about asking how you can learn to be better.
4. Do One Thing Really Well
Pick something to work on and deliver, everything else is a distraction. This is hard: you work at a startup and there is always a million things to do. But in order to make everything work, you need to make something work first. Ask for space and focused time, your manager will understand and respect you. Build a brand for yourself as early as possible. Show that you are effective and can get something done on your own. The challenge is to do one thing really, really well when you are constantly surrounded by shiny objects. Deliver something — all the fun stuff happens after.
5. Don’t Quit
Working at a startup feels like eating glass shards. Because of your lack of experience, every cut is going to feel even more painful. Your insecurities mean that it will be easy to take things personally (like when you get critical feedback or need to deal with a difficult colleague). When this happens, you will likely want to run away. If you are working for someone else, you will want to start your own thing; if you run your own startup, you will want to quit and get a regular job. Try not to indulge in these fantasies: avoiding problems won’t solve them. A better approach is to reframe them as opportunities to grow. Critical feedback? Your manager is telling you things to change so they get to keep you for longer (it means they care). Annoying colleague? Perfect way to practice being a future CEO. Whatever you do, don’t just quit. Vent all you want, but at least try work on it first. Your future self will thank you.
