29 on the 29th

I arrived into the world 29 years ago today. Leading up to my birthday each year, I usually find myself in a state of thought and reflection. I think about where I've been and the direction life is taking. I think about the choices I’ve made so far, the ways of thinking that brought me to this moment.

I know a year from now I will be turning 30. That knowledge is there in the back of my mind, as it is for many of us during important life milestones. What have I accomplished? What am I leaving behind? Sometimes it’s easy to lose sight of the big picture in the little details of every day life. Every now and then, it’s important to take a pause in the constant activity and look at the bigger picture.

There is a feeling of significance as I approach this final year of my twenties, a sense of urgency. I think about expectations I’ve had. Where I anticipate I will be at 30. The past few months, I feel as though I've had some important realizations. Someone very close to me passed away just before the start of this year, and I think about all the things I was sure she would see me accomplish. There's plans and ideas, scenarios mapped out in your mind, and the finality of death makes you realize the stark difference between thoughts and reality. A part of me feels like she never got to see me 'successful', always just striving towards an ambiguous goal.

When will I ever feel satisfied, successful, as though it's 'enough'? There's a sense of vulnerability to putting this into words. It gives a voice to unacknowledged fear, a fear that you aren't good enough as you are. I feel a sense of inadequacy, insignificance.

Thinking all of this over, I pulled down the ‘commonplace books’ full of notes I’ve collected over the years, and spent time distilling 29 of the most important bits of wisdom I've come across. It helps to know that there are others throughout history that have struggled with the same questions. Because of reading, I have access to understanding and insight far beyond of my modest 29 years. I have the capacity to become a unique collection of the thoughts of everyone who has come before me.

I think about the amazing people in my life. I think about what they would say If they had to sit and write something to say at my funeral. How would they feel? What would they miss most about me? What did I give them while I was alive? What did my life allow them to discover about themselves? I think about how you measure life. There’s so much I want to be. I want to be a better friend. A better husband, son, brother. But wanting to be better, constantly striving, seems to imply a sense of not being enough where you are. How do you balance ambition, wanting more, wanting to be better, with acceptance and gratitude? This, I think, is a central question to life, one I have wrestled with over the past few years. The best answer I can come up with is to cultivate the skill of adaptability. "Adapt to the unknown" has become a motto of sorts. There is an inherent uncertainty to being alive. I've learned to love and respect the power of the Latin phrase "Amor Fati", Love of fate. Overall, I feel overwhelming sense of gratitude. If you're reading this, thank you. I'm so glad that our lives have intersected for this brief moment. And, those of you who know what you mean to me, thank you for your impact on my journey through life this far. Your friendship and love mean everything to me.

One last thought as the day comes to a close- "When you run so fast to get somewhere, you miss half the fun of getting there". Where am I trying to get? To the end? The end of what? There is no end, only a perpetual present. Here’s to living in that present together.

1. Invest in long term relationships. Commit to a partner- Life is far more fun shared with someone else. Yes, love takes work and dedication. That’s part of what makes it worth it. It's invaluable to have someone who understands you. It has been a decade to the day since my wife and I began dating, and I don't hesitate to say it's been the most consistently rewarding aspect of my life so far.
2. Be very careful with identity and give plenty of consideration to the ways you define yourself. Maintain an inner scorecard. Diversify your identity, with multiple areas in which to find fulfilment. For example, if you have an off day in business, it helps to offset with an athletic pursuit you can make progress in.
3. Define and defend your principles. Consider- when was the last time you had to make a hard choice in support of what you say your priorities are? For me, it was the decision last summer to skip a weekend of bachelor party camping to drive home and attend a family reunion put together by my Grandma. I didn't know it then, but it would turn out to be the last time I saw her. I will always be thankful for that choice. 
4. Read widely and learn from the experiences of others. Recognize that whatever you are facing, whatever you are going through, there's a strong chance that someone throughout history has encountered the exact same scenario, and has has written about it. Keep a commonplace book to collect your thoughts in a central location.
5. Write. Capture your "monkey mind" on the page. Seeing your thoughts in front of you takes away their power to control your emotions. Also, clear and concise writing is the sign of a well-ordered mind.
6. Even if you only get one idea from a book, it’s well worth any price. Related, when writing, sometimes 99% of it is irrelevant but there is 1 seed of a good idea in there to develop.
7. Two complementary sayings: Discipline equals freedom (Jocko Willink) and Hard choices, easy life. Easy choices, hard life (Jerzy Gregorek). Take cold showers. Practice fasting. Get comfortable being uncomfortable. Adapt.  
8. Question systems and habits regularly. Develop your own personal operating system. Be disciplined where it matters so that you have the freedom to be creative. Being stable where it counts allows you to take risks in other areas.
9. Two strategies I like from the world of investing: the Barbell strategy (balancing 10-15% of risky, speculative bets with 85-90% of conservative, safe investments) and Asymmetrical risk/reward (protect the downside).
10. Be Antifragile. To be Antifragile is to not only endure challenge but to be strengthened by it. Nassim Taleb describes the central illusion in life well: that "randomness is risky, that it is a bad thing- and that eliminating randomness is done by eliminating randomness."
11. You become the average of the 5 people you spend the most time with (also known as the "5 Chimp Theory")
12. Be multi-disciplinary, build up a latticework of mental models to pull from. Learn to see connections between different areas.
13. Visualization is powerful. Use your imagination and develop the ability to vividly picture what it is you are after.
14. Lead with gratitude. 
15. "What you do is more important than how you do it, and doing something well does not necessarily make it important". Focus on effectiveness over efficiency.
16. From Marcus Aurelius: "Reflect that our successors will see nothing new, just as our predecessors saw nothing more than we do; such is the sameness of things, a man of forty with any understanding whatsoever has in a sense seen all the past and all the future."
17. "Someday" is a disease that will take your dreams to the grave with you. Learn to recognize Resistance in its many forms (see: War of Art)
18. Remember the formula (+)(-) and (=). Martial arts coach Frank Shamrock has a formula for achieving greatness: Plus, minus and equal. You constantly need to surround yourself with someone who is better than you are (+) someone who is not quite as good (-) and someone who is equivalent to your skillset (=). 
19. When facing multiple options, ask: Which 'lead domino' will make the rest irrelevant or easier? Learn to ask better questions. Clarify by asking: what would this look like if it were easy?
20. Test assumptions. For example, just because you're born in a particular place doesn't mean you have to settle there. 
21. Cultivate patience. We'll see. Don't be a Donkey.
22. You must never, ever fool yourself, and you are the easiest person to fool (Feynman). Related to this is the vital importance of self-awareness. Ego is The Enemy.
23. Learn and understand cognitive bias.
24. Desire is a contract you make with yourself to be unhappy until you get what you want. Choose and limit your wants carefully.
25. Behind mountains are more mountains (you get to the peak of one and then it's soon time to climb the next). In life, there is no finish line. 
26. The meaning of life is to help others find meaning in theirs. (Man's Search for Meaning).
27. Follow your own advice. Sweep every day.  Many of these things I thought I had understood. I've written them out, considered them. And then, upon reflection, I realize there are often cases where I fail to apply them.
28. Regret minimization framework. "When Im 90, will I smile when I think back, or will I frown and regret not having done it? ...Success is about making your life a special version of unique that fits who you are. Not what other people want you to be." (Mark Cuban)
29. MEMENTO MORI. Remember your mortality. The balance of life diminishes day by day. Look at the clock. Today is almost over. Have you lived well today? That's all you can ask for.