Today is the last day of my 20s. Tomorrow I turn 30. I spent time this week reflecting on the life lessons I’ve learned that are worth communicating.
I don’t envy the challenges of growing up in an age of connected disconnectedness. I imagine it’s harder than ever knowing who to listen to when you have more options than ever before.
The democratization of opinion has led to the platforming of beautiful ideas from voices who wouldn’t otherwise have a platform. At the same time, personal algorithms lead you to what you want to hear and create feedback loops around ideas that may be comfortable but will keep you in unhelpful or damaging patterns.
Here are the core values I prioritize:
Authenticity, Achievement, Adventure, Community, Curiosity, Friendships, Inner Harmony, Self-Respect, Integrity.
Interpret the following advice accordingly.
Whether you’re entering your 20s or well into this season, this is my contribution to your quality of life. I hope that you can use my experiences as a useful data point in yours. Choose to live an incredible life.
Here’s a handful of hard-won lessons I want you to hear.
Tomorrow I turn 30, here’s what I learned in my 20s…
Money doesn’t bring happiness – it brings options. Figuring out what makes you happy has nothing to do with money. Grinding does not equal unhappiness. Time freedom does not equal happiness. A limiting belief I had to shed was that the price of future happiness is unhappiness now. If you believe that, my friend, you’re in for a nasty surprise.
At 30 you will have begun to see and feel a divergence in life outcomes based on how people spent their 20s. Habits compound quietly for years and then get louder.
The skills you need to go from zero to 1 are not the same as those that take you from 1 to 100. In anything.
Satisfaction and dissatisfaction compound and are the cumulative result of your decisions.
Use your 20s to deep dive into the patterns and traumas you collected from childhood. Heal yourself and define yourself. Build yourself and be yourself.
Shame is often an “x marks the spot” for the inner work you must do.
The only way to grow is by looking directly in the eyes at the darkest parts of yourself.
Your growth ceiling is equivalent to your ability to tolerate discomfort.
A marriage (relationship) ending is not the end of your life. However, not learning from pain can be. All pain is a lesson.
Neglecting your health is unintelligent. This will keep you unhappy.
The levers of global optimization are nearly always different from the levers of local optimization.
If it’s a question between betting on yourself or the other guy, bet on yourself.
Your education is the only investment that compounds forever. Invest accordingly.
If she doesn’t pay attention, that’s not a signal to try harder – it’s a signal to walk away.
Don’t listen to rules on dating. Act from your principles. Be a good person, develop your own intuition, and trust your gut.
Most of the dating advice on social media is designed to rack up views and sell products by playing on your fear and insecurity. Use “cui bono” as a test.
Pickup lines are a surefire way to embarrass yourself. Smile, look her in the eyes, and have a normal conversation. The object is connection, not a phone number.
Emotional maturity and an ability to laugh at yourself will make you way more attractive than anything else you can become.
The “friendzone” does not exist. If you think you’re in it, then you’re not being honest about what you want.
- Any successful relationship must be able to talk candidly about sex, intimacy, work, money, play, children, spirituality, growth, and dreams. If you are walking on egg shells about any of them, it’s a red flag.
- The best gift you can give to a relationship is working on yourself.
Men, if you can’t maintain friendships with women – you may want to check to see if you subconsciously believe that women are simply sex objects.
Learn to decouple shame from every aspect of your sexual inclinations. Sexual shame only comes from external programming and doesn’t benefit your quality of life.
You cannot hope to be healthy together if you haven’t yet learned to be alone.
Love needs action. Trust needs proof. Sorry needs change.
When someone shows you who they are, believe them the first time.
No one is owed a seat at your table – family and old friends included. If you keep someone around who doesn’t inspire you or contribute to your happiness in some way, you’re choosing to play life with a handicap.
Intimidation is the tactic of a small man. Small men are easily manipulated by ego and fear.
If you want something from someone, create a scenario where they get to be the hero.
Happiness, meaning, and community – if you spend your time trying to “find” them, you’ll be searching for a long time. Spend your time creating them.
The more you can kill your ego, the greater control you have over yourself and your surroundings.
The fastest way to grow is by looking directly at the parts of yourself where you feel shame and exploring why. Meditation will help you to integrate these parts. Psychedelics will do it faster. (Legally I am not encouraging you to do anything that breaks any laws, I am stating evidence-based research.)
Animals respond to behavioral conditioning. Humans are animals too.
Read broadly. Collect ideas. Inventory your biases. Ruthlessly edit your working assumptions. Spend time with great thinkers.
Respect does not equal authority. Beware those who conflate the two.
Everyone is looking for meaning in their existence, be kind.
Nice does not equal kind. “Nice” is violence against the self. Candor, clarity, timely feedback- these are kind.
Go to therapy. Find your blind spots. Therapy is a tool to show you where you can grow. Integration is the process after therapy where growth happens.
Nobody is coming to discover you. You have to do it for yourself.
Make your peace with death. Then life will truly begin.
Religion is a comfort blanket. Be wary it becomes a sedative.
A belief that cannot be questioned is a bridle in your mouth.
A morality that concerns itself with uncouth words but not hungry mouths or broken bodies isn’t worth much.
You can’t know what other people think about you. So decide to fill in the gap with a best-case outlook and take the risk.
If movement encounters resistance, you’re likely going in a growth direction.
A surefire way to stunt your growth is by exaggerating to yourself about what you have done, who your friends are, what your skills are. Conversely, growth is accelerated by acknowledging the limits of your knowledge and abilities.
If asking questions makes you look dumb then try to look dumb as often as you can.
Life may not become easier, but your soul will be lighter after you have that hard conversation.
Wherever possible, provide constructive feedback in private. You will likely gain an ally. However, disrespect needs not be afforded any such courtesy. This applies to both the feedback and the privacy.
When someone insults you publicly, you are no longer having a person-to-person interaction, you are on stage in front of an audience. The most effective way to respond is indirectly – keep cool and give them the rope to hang themselves. Questions like “I don’t understand, could you explain what you mean?”, “Could you repeat that last part?”, “What does ___ mean?”, “Are you having a bad day?”, “Are you feeling ok?”, restating the disrespectful part as a question and staying silent – these are lethal.
A compliment is a gift and an acknowledgment – honor the gift by receiving it with thanks, not deflection.
Staying cool and collected in the face of an emotional outburst is a flex.
Obedience is not a virtue.
A list of achievements is far more powerful than a list of plans, even when the achievements are small. Put in the effort to consistently bring your superior the first list and they’ll love you for it.
The world will NOT be better off if you’re not in it.
A sense of humor that relies on putting anyone down is the expression of insecurity and self-loathing.
Want to become trusted? Engage in anti-gossip – give people compliments behind their backs.
What is obvious to you is not always obvious to others.
The most effective communication is not concerned with expressing an idea. It is concerned with understanding where an audience is and guiding them from A->B.
If you don’t look up to their experience, then don’t take their advice.
Fix your negative self-talk as early as you can.
A direction is sufficient – you don’t need a defined destination, you need movement. You can’t steer a parked car.
The best stories always come from saying yes to situations that are laced with uncertainty – strange circumstances, people, and opportunities.
One of the most consistently valuable skills is learning how to make someone else smile. The ROI cannot be overstated.
Advocate for what you’re worth. If you don’t, you’re accepting future resentment.
Learn what effective boundaries are and then learn how to set them.
Become consistent at under promising and over delivering.
Pausing while maintaining eye contact will tell you if they’re lying.
Cheap dopamine will enslave you. The way to break dependencies/addictions is by deconstructing the upstream need that is not being met.
Be wary of allowing any ideology or ideological position (religious, political, or other) invade your sense of identity – you will lose the ability to distinguish between dissent and personal attack.
Regularly inventory your habits – if you lived the last 2 weeks on repeat, would it get you the life that you say you want?
Authenticity requires courage. It’s also the price of admission into the lives of others who are authentic.
Step change is not a reliable growth strategy. Focus on consistent incremental growth. 1% better every day.
You can go from zero to reasonably competent in any skill with 10-20 hours of focused learning.
If you want to become a sharp thinker, learn logical fallacies and collect mental models.
If you want something you’ve never had, you have to do something you’ve never done.
I used to look with raised eyebrows at people who took a gap year either after high school or after college as falling behind. After climbing one mountain only to descend for a new peak, I think a gap year(s) can be a useful tool to gain perspective. There is no “behind”. And there will be beautiful vistas on any climb. If you’re still not sure where to go, then start climbing anything – you’ll be able to see farther than in the valley and you’ll be a better climber for the next adventure.
Lead by example in your friendships. Be the friend you want others to be to you. Cultivate friendships with people who inspire you.
Don’t throw good energy after bad. If someone does not respect your boundaries or time, move on.
There’s no such thing as “not enough time” only the expression of priorities through lived actions. This is just as true for other people as it is yourself.