40 Lessons from 30 Years

Why keep it to 30

Over a slice of drunken pizza on dirty Sixth street last weekend, my friend Zakk asked me to come up with 30 life lessons for my 30th birthday.

I only got through five before I got distracted, but I thought completing the challenge here with a few extras would be fun.

So, here they are, in no particular order.

It’s never the right time. Any time you catch yourself saying “oh it’ll be a better time later,” you’re probably just scared. Or unclear on what to do. There is never a right time for the big things in life: having kids, changing jobs, breaking up, getting engaged, married, moving in together. And no it’s never an amount of money, either. 

Err on the side of too early over too late. Related to that point, since there’s never a “right time,” it’s almost always better to do things “too early.” Your conception that it’s too early is just your fear, and once you dive in you’ll figure it out. Old people tend to regret the things they didn’t do, or didn’t do earlier. Not the things they did.

Bad things happen fast, good things happen slowly.

You have more time to build a career than a family. You can complete great work well into your 80s and 90s. If you want to know your grandkids as adults, you only have until your mid 30s to start a family. Every year you spend waiting is another year you lose with your future family. 

Beware of shadow careers. This idea comes from Steven Pressfield: “Sometimes, when we’re terrified of embracing our true calling, we’ll pursue a shadow calling instead. The shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.” See also: When The Money’s Just Too Damn Good. 

Get in shape. It’s not enough to not be fat, you need to be strong and have endurance too. Find a form of exercise you enjoy doing. Focus more on increasing your physical capacity than on losing weight, the weight loss will follow if you’re getting better at running, swimming, lifting, etc. 

You do your best work when you’re not working. Your brain needs downtime to connect the dots like your body needs rest to strengthen itself for the next workout. If you’re always working, always trying to download information, always trying to be productive, you’re stifling your best insights from bubbling up. 

Standing events are the best way to regularly see friends. Constantly having to schedule outings, dinners, etc. makes it hard to regularly see people. Create standing events. Invite people you want to spend more time with. It’s the easiest way to get more friend time in your week.

Remote relationships cost you real relationships. Every minute you spend cultivating relationships with people through a screen is a minute you’re not deepening relationships with people you can actually see and touch and smell. 

No one is thinking about you very much. So don’t worry about looking stupid or embarrassing yourself or whatever. No one cares. 

The time will pass anyway. Maybe it’ll take you five or ten years to succeed at whatever you want to do. Well, those ten years will pass anyway. In ten years you can either have made progress on your goals, or still be whining about how long things take. 

Someone else has already solved your problems. Unless you’re at the fringes of science and technology your problems are not new, people have been dealing with some form of them for thousands of years. Read books, they’ll give you answers.

Most of the world is held together with duct tape. The last 5-10% of everything seems to get slapped together at the last minute. It’s just hard to see in any area where you aren’t an expert. Don’t worry about living duct-tape-free.

Money is a tool for freedom. The best reason to accumulate wealth is to buy yourself freedom from anything you don’t want to do, and the freedom to do the things you do want to do. Money is not an end in itself. If you sit on it and never use it, you’ve wasted your life. 

The faster you get something, the faster it tends to go away. Languages, money, influence, friends, the sharper the rise the faster the fall.

Rebuild some relationship with nature. Spend as much of your day outside as you can. Eat local food. Go for long walks. Try hunting or harvesting your own food at least once. You were not meant to sit in a wood box staring at technicolored glass all day. 

Another water bottle won’t fix your hydration problems. A new note taking tool won’t make you a better writer. If you find yourself looking for a tool to solve a problem, you’re probably just procrastinating. 

Many of the best changes in life are unknown until you make them. Feeling “fine” is a dangerous attitude. You might have no idea how much better you could feel, how much happier you could be, how much fuller your life could be. Changes like exercising regularly, cleaning up your diet, doing psychedelic therapy, it is impossible to convey the change in perspective to someone who has not experienced it. Sometimes you just need to trust the zealots. 

MDMA and Psychedelics. On that note, two of the most important experiences in my life were doing MDMA and psychedelics in introspective self-work settings. There are some risks, and obviously legality is a concern, but I consider them absolutely pivotal, life changing experiences. I cannot fully explain the impact to you if you haven’t used them.

Host more events. Everyone wants to do more social stuff, but no one wants to organize it. Organize it. It’s not that much work, you’ll be much happier, and you’ll make more friends. 

Get physical. Buy real books. Print photos. Write cards. Buy vinyl. Space is how you show yourself and others what you value. Minimalism is a horrible, dull trend. Fill your life with totems to what you care about. 

Money can absolutely buy happiness. So long as you spend it on upgrading and expanding the things that make you happy, instead of using it to play status games or on fleeting experiences. 

Advice only works in retrospect. You usually have to have experienced a failure or loss to understand the relevant advice. Hearing some piece of advice will rarely stop you from making the related mistake. 

The whiners are the loudest. Happy people are off enjoying their lives, not complaining about them on social media. This is especially true for parenting. 

Be early. Get on trends early, try new things early, visit places early, learn how to develop the requisite taste to be a little ahead of everyone else. It’s fun and can be profitable.

Embrace the many things you’ll never do. Enjoy saying, “I’ll never learn Chinese,” or “I don’t need to visit every country.” Everything you say no to creates space for the most important things to say yes to. 

Slow down. 

You can handle more than you think. If you aren’t occasionally failing at things, you’re not pushing yourself. 

You only need to make a few great decisions per year. You only need to get a few big things right each year and follow through on them. Your life will be shaped by surprisingly few big choices. 

Don’t open a cafe. Trust me. 

No one is crazy. They just have different values and information than you. If you had their life experience, you’d probably think the same. The sooner you embrace this, the sooner you can empathize with people you disagree with instead of pretending you’re superior. 

There’s interesting gray between the black and white. If something seems obvious, but people strongly believe the opposite, see if you can convince yourself of their view. You might just learn something.

You find what you like by trying it, not by thinking about it.

Increase the difficulty. If you’re reading this, then your life is (probably) already on easy mode compared to the global and historical standard. You need to strategically introduce some challenges to keep yourself motivated. Don’t ruin yourself, but don’t let yourself get too complacent, either. 

If it looks sad, it needs water. A good rule for houseplants and humans.

You usually kill by overwatering, not underwatering. Another rule for houseplants and humans. Sometimes the best action is to do nothing or wait instead of trying to constantly do something. 

Build relationships with restaurants, cafes, bars, etc. Learn the names of people who work there. Help make their jobs and lives easier. Bring new customers to them. Help the local places you care about succeed. Invest in your community through action, not just money. And never be friends with someone who treats wait staff poorly. 

You don’t have to make money back where you lost it. If something in your business or life is losing money, you don’t have to plug the hole right there. Often it’s easier to make the money back elsewhere. 

Trust your negative gut, not your positive gut. If you have a great feeling about something, you might just be excited or gullible or not thinking it through, so take your time. But if you have a bad feeling about something, you’re almost certainly right about it. 

Stressing about a problem rarely fixes it. Try to bias towards improving things instead of whining about them. Or if you can’t fix them, forget about them.