How to Succeed in Your 20s (Pt. 1)

Do these things to outperform 99% of your peers.

I just got back from Hawaii and I’ll be in Toronto this weekend. Next week, I’m in Miami hosting the second Lumos House.

The Lumos House is a series of dinners, tech events, parties, and fireside chats taking place in a private mansion that my friends at Blindspot and I rented. It’s free of charge! Apply here.

After that, Los Angeles, San Francisco, and Seattle. New York Tech Week is also in June, and I’m planning something big. If you’re a sponsor or brand that wants to get involved, reply here.

Now that I’m in my late 20s (I’m 28), I like to spend time reflecting on what I did right in my early 20s to land me where I am now.

I’m lucky to have had the experience of working in product and business roles at both large companies like Google and Meta, and tiny startups. I’ve also been able to advise and invest in early-stage startups as an angel and investment partner at a $1B venture fund, write about tech careers for publications like Business Insider, and build an events company that allowed me to quit my corporate job and sponsor my own visa in the United States.

Some would look at my career and scoff, “That’s it?”. Others might (hopefully) find some inspiration in what I’ve accomplished.

Personally, I’m very happy with my career, from both an experiential and financial perspective. I’ve learned skills that allow me to excel at large corporations and entrepreneurship, and I’ve created a fulfilling life for myself as a late-20s entrepreneur.

This is for those of you who are in your early 20s, who want to build an exceptional career in tech.

How to Succeed in Your 20s (Pt. 1)

Your early 20s are interesting. You’re incredibly ambitious with big goals, but might not have the skills and competency to achieve them quite yet.

Many of you are focused on earning (I certainly was), but in reality, learning is more important. The most important things to prioritize are to develop your skills, find your strengths, build your reputation, and acquire specific knowledge.

Do these things in your early 20s, and you will outperform 99% of your peers.

Climb more hills.

I came across the classic algorithmic problem in computer science called hill climbing:

Imagine you’re going for a hike in hilly terrain and your goal is to reach the highest peak. It’s foggy, and you can only see a few feet in each direction.

The approach to solving this is analogous to how we should approach our careers:

1. The simplest approach is to keep walking upward. Take the path that slopes upwards the most and keep going. This is the best immediate choice, and in computer science, is referred to as the greedy algorithm. The risk is that you could end up at the peak of the smallest hill. You’re only covering a tiny part of the terrain. This approach refers to the individual who chooses to do the same job for decades and stays within their comfort zone.

2. A better approach is to introduce some randomness and sophistication to your path selection. Halfway through your climb, choose a slightly different route and occasionally move to a lower point to explore other paths to reduce your likelihood of taking the path to a smaller hill and maximize your surface area covered. This approach refers to the individual who pursues different interests, roles, and disciplines to experiment, learn, and grow.

The most fulfilled people I know are those who have pursued non-linear career paths by trying new things, making pivots, and having the courage to start again from day one.

Create proof that you can do hard things.

Make it your first instinct (and second nature) to go after things that scare you.

The more difficult, gritty, and hard things you force yourself to do, the more competent you will believe yourself to be.

When I first moved to America, I was horrible at public speaking - it scared the crap out of me! So I relentlessly grilled my manager on presentations until she would let me present in front of executives, and I did ~30 of them in a year until I was satisfied. Today, my fear is mostly gone, and I’ve spoken on podcasts with tens of thousands of listeners, on stage in front of hundreds of people, and at events like SXSW and Advertising Week.

One of my favorite quotes:

“Do the thing you fear most and the death of fear is certain.”

— Mark Twain"

Strive to give first (and don’t keep score.)

The most successful people I know have built a reputation by consistently solving problems for other people. They’ve spent their early careers giving, helping, and supporting others—consistently building goodwill with the community.

Important: They never keep score. When the time comes and they need help, the community gives back tenfold.

When I was first building my network, I made it my mission to help as many entrepreneurs as possible. I connected them with investors, got them featured in national publications, helped them hire and scale their teams, etc. Today, I have a large network of founders who trust me, send me deals, participate in my programming, and offer their time, products, and services to me. The value has come back 10x.

Learn to communicate clearly.

In school, we’re taught that great writing is substantial (remember minimum word counts?) and creative. In the business world, this couldn’t be further from the truth. Effective writing and speaking are concise, clear, and direct.

When communication isn’t done well, the people involved pay a price. Poorly written emails cause tension and confusion. Long-winded conversations kill positive energy. Unclear presentations destroy momentum. The best way to communicate is to do it as simply as possible.

Meet 1 new person every week.

The easiest way to consistently expand your circle is to remind yourself to meet at least 1 new person every week. Do this by attending industry events, cold emailing others, or asking someone for an introduction.

If you spend the majority of your time around the same people, you will be prone to groupthink, bias, and narrow-mindedness.

Incrementally expand your network to access more opportunities, ideas, and ways of thinking.

Occasionally, break free from the herd.

The most radical and innovative businesses today started as “weekend projects” built by tinkerers. If you spend your time watching, reading, and listening to the same things as everyone else, you’ll achieve the same average outcomes. Take time to understand what truly interests you (the more niche, the better), and ignore what others may think about them.

As a kid, I had hobbies that weren’t considered “cool” to the masses. But today, I attribute a lot of what I know about social psychology, group dynamics, and influence to my years of obsession with the hobbies I loved as a child.

Understand that compensation growth is non-linear.

At my first internship at 19, I was making $500 a month at a large advertising agency. I couldn’t afford to do much but I learned a ton. At 21, I made $40,000 a year, working for a large national company. Most of my friends were making over $80,000 a year. I felt inferior but believed in the long game - that learning skills today would result in earning tomorrow. Three years later, at 24, I tripled my compensation with a job switch into tech, and doubled it again in the next two years.

I know several people who are currently in a position where they are making below market for what they should be compensated, but I have no doubt that in the next five years, they will triple or quadruple their income based on the skills they’re learning now. If this is you – believe that the hard work and effort put into developing your skills will pay off in the future.

***

Thanks for sticking with me through this. I hope it was helpful!

Leave a comment below to let me know what stuck with you. What would you add?

Stay tuned for part 2.

📌 Andrew’s Picks

Fascinating internet things I’ve come across…

• Career Decisions – Elad Gil, entrepreneur and investor, shares his blueprint for building a successful career for yourself.

• The Four Stages Of Competence – The 4 stages of learning, originally coined by polymath Josh Waitzkin, chess prodigy and competitive martial artist. He’s mastered the art of learning to the point where he’s considered an expert in multiple disciplines.

• What We Look for in Founders – The 5 traits Paul Graham (founder of Y Combinator) looks for in founders to invest in.

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🖼️ Behind the Scenes

I just got back from a week-long trip to Hawaii with my girlfriend. We ate poke, hung out at the beach, and snorkeled, and upon returning to New York, I realized how grateful I am to be able to just fly to a tropical island on a Tuesday to spend time with people I love.

It got me thinking about what freedom truly means.

A lot of people talk about reaching Financial Freedom. The liquid net worth number you have to hit to reach financial independence and “retire” and not worry about working.

What people don’t talk about as much are Time Freedom, Relationship Freedom, and Purpose Freedom. These matter just as much.

• Time Freedom. You spend your work life doing what you love. You dictate your own hours and are free from work responsibilities.

• Relationship Freedom. You have the option to answer to nobody. You choose who you get to work with—and you spend more and more of your time surrounded by people who energize you, whom you appreciate, and who appreciate you.

• Purpose Freedom. You spend your life serving a mission or solving a problem that you deeply resonate with. You don’t just have a job or a career, you have a vehicle to connect with all the things that resonate with your life values and ideals.

I believe that the most fulfilled people in the world have achieved at least 3 out of 4 of these freedoms.

Me and Nicole in Hawaii!