28 Lessons I Learned at 28
Reflections on my birthday, Lumos House in SF/LA & Job Opportunities!
👋 Friends,
I turn 29 today.
This past year has been the most important one of my life.
I quit drinking, met the love of my life, quit my job—and went all-in on building a company—taking it further than I ever imagined
I’ve learned a lot about taking risks, managing relationships, building wealth, and motivating myself from people much wiser than me.
Today I’m sharing the 28 lessons I learned at 28. Hoping one of them be helpful and can impact you in a small way.
Learn to do things with fewer moves. Like chess, there is elegance in doing things with simplicity, like writing with fewer sentences, speaking with fewer words, or accomplishing a goal with fewer actions
Being kind is the ultimate life hack. It casts a halo over you, improving your ability to do whatever you’re trying to do. Conversely, being unkind will make everything slightly worse. Remember to be kind.
Find your playground. Just as children have legos and playgrounds to be creative, adults need a space to feel fulfilled too. Starting a business is one. Writing or creating art is another. Find something that lets you be a child again.
Build your naked skills. Learn to be a better communicator, leader, and problem-solver, as these are the skills that stick with you, no matter where you are. Build the skills that will help you succeed across roles and industries—even if you were suddenly transported halfway across the world.
Like attracts like. The easiest way to evaluate a new acquaintance is to observe who they spend time with. Are they motivated, collaborative, and kind? In contrast, there are people who I avoid intentionally because of the cliques they participate in.
Problems are opportunities in disguise. Most people complain when they face a tough problem. They ask, “Why me?”, and perpetuate a self-reinforcing belief that they’re cursed and unfortunate. But hairy problems can also be a gift—they are opportunities for you to learn how to solve them and prove that you can do hard things.
Find asymmetric risk. When you find opportunities with low downside and limitless upside, not taking the leap can be the riskiest choice of all. The real danger lies in living with a lifetime of regret and wondering, "What if?"
Opportunities like quitting your job, speaking in public, or asking someone out might seem risky, but in truth, the potential downside is negligent compared to the potential upside.
If you’re about to write an angry email, wait. Write the email, but wait 24 hours before you hit send. You most likely won’t end up sending it, saving you from potentially disastrous consequences. Angry emails accomplish nothing. The same goes for texts and phone calls.
Nobody is thinking about you as much as you think they are.
Motivation is overrated. Environment design is underrated. Stop relying on doing things with sheer discipline, and instead, find ways to manipulate your surroundings to help you accomplish your goals.
Building your own routine is overrated. Most of the world still operates on weekdays and relaxes on the weekends. Entrepreneurs glorify the freedom that comes with being able to design your own schedule, but they still have clients who work nine to five and friends who are only free on the weekend.
Saying “I don’t know” is underrated. Say it more. You’ll learn more, open up more doors, make more friends, and people will trust you more.
The whole point of your career is to build an awesome life. A great career lets you accumulate wealth to buy freedom. Freedom to spend more time doing what you love, with people you love, and if you sit on wealth and never use it, you’re missing the point.
Lift heavy things more often. You’ll be more attractive, more confident, healthier, reduce injuries, and improve your ability to do all the physical things you love.
You do your best work when you’re not working. Just as your body needs rest to build strength, your brain needs downtime to form new ideas. If you’re always trying to get things done and be productive, you might be blocking your most profound ideas.
Tell people you admire them.
How to manipulate time. Adjusted for the subjective increase in how fast time passes life is half over by 23 or 24. Slow time down by doing novel things. Take a new path on the way to work. Stop and smell the roses. Travel. Do things you’ve never done before that excite you and stimulate your senses.
Big things take the same amount of effort as small things. A job that pays $300k a year will take the same 40 hours a week as a job that pays $60k a year. Similarly, servicing a client that pays you $15k a month will take the same effort as servicing one that pays you $5k a month. Always ask yourself, “How can I 10x this without increasing my effort?”.
Chase awe. As a child, we were always in awe of new ideas, new things, and new experiences. Somewhere along the way, everything became routine and we lost the ability of awe. Get it back by opening your mind to new ideas again. Read new books, try new things, and go to new places.
Trust is earned in drops and lost in buckets. It takes a lifetime to build a reputation and minutes to lose it. Similar to how there is asymmetric positive risk, there is asymmetric downside risk too—opportunities with low upside but unlimited downside. Avoid them at all costs.
Record more stuff. Capture your parents’ favorite childhood stories, film memorable moments with friends, and record special moments with your partner. In a decade, you'll be grateful you did.
Fire your boss (or your client). Remember, you have the power to leave a bad situation. Your relationship with your boss or client goes both ways—you can offer suggestions, give feedback, and even say no. We often underestimate our own value, and sometimes, they need you just as much as you need them.
Don’t plan further out than a year for your career. Five-year plans rarely go as expected, and creating one might make you rigid and stubborn. Instead, plan a year ahead and be prepared for unexpected opportunities. Luck happens when preparation meets opportunity.
Trust your gut. Careful, deliberate decision-making can only get you so far—you need to listen to your emotions too. A good rule of thumb: If you have a good feeling about something, take your time. But if you have a bad feeling, you should trust your intuition.
Useful, not true. Sometimes, we spend too much time trying to find out whether something is true or not:
“Will this work?”
“Am I good at this?”
“Does this person like me?”
…but the truth might not even be valuable at that point in time. Instead, reinforce the belief that is most useful, not true.
Host events. You’ll gain respect, make more friends, and be happier.
You’re capable of more than you think. If you aren’t failing at something from time to time, you’re too comfortable, and you’re probably not pushing yourself hard enough.
Don’t listen to me. I’m just someone on the internet sharing advice that’s worked for me. You don’t know my skills, luck, or unique life circumstances.
Career outcomes are rarely deterministic and you can only connect the dots looking backward.
In fact, don’t listen to anyone—they don’t know you as well as they think they know you, so trust your instincts, stop listening to others, and own your decisions.
📌 Andrew’s Bookmarks
Fascinating internet things I’ve come across…
Second Nature Skills — Ever noticed how some things just come naturally to you, while other people have to try really hard at the same things? Anu calls these “second nature skills.” You probably have more than one.
Anything You Want – One of my favorite recent books on entrepreneurship.
Alex Lieberman builds an app in 10 minutes without technical knowledge – Everything is about to change.
💼 Job Board
Sharing job postings from companies that I advise, have invested in, or have close relationships with. Please apply below and reply to this email once you’ve done so.
Lead Product Manager, ResortPass
Account Executive, Thera
Head of Engineering, Thera
Founding Engineer, Superpower
Chief of Staff, Eniac Ventures
City Launcher, POSH
Growth Marketing Manager, Blindspot
VP of Sales, Otis AI
Senior Account Executive, Cal.com
Client Enablement Associate, Carry
Software Engineer, Cassidy
Founding Full Stack Engineer, Micro
Founding Full Stack Software Engineer, Plymouth Street
Business Development, Remedy Product Studio
Founding Engineer, Rubie
Head of AI, ARI
Have a job to share? Please reply to this email.
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🖼️ Behind the Scenes
One of the most rewarding things I’ve done in my career has been building a team from scratch. Jacob was my first hire and is now my Chief of Staff. Some of you may have met him and immediately noticed how diligent, personable, and on the ball he is.
We celebrated a successful first half of the year at Keen’s (I recommend the T-bone), and it’s been surreal to watch him grow into a leader, capable of hosting multiple events a week and producing on 500-person conferences independently.
I hope you all get to meet him!
Excellent list of lessons! Really brilliant! And happy birthday :)))))))
Happy Birthday and go Jacob!