40 Lessons From 40 Years

I turn forty today. I can’t even believe I just typed that sentence. Over the past month, I've been reflecting on the lessons I’ve learned directly through experience or indirectly from family, friends, mentors and teachers.

I wanted capture and share these learnings for one important reason: I’m now a father to a beautiful baby girl and I’m not going to be here forever. Preserving myself digitally is becoming more important as I enter middle age.

Here are forty nuggets of wisdom that I’ve picked up throughout my first forty trips around the sun. May the next forty (god willing) be as wonderful and enlightening as the first forty.

  1. It’s ok to say, “I don’t know” because it’s impossible to have all the answers. The older I get the more I realize knowledge is practically infinite and I don’t know that much.

  2. Don’t underestimate the power of being the first to truly believe in someone.

  3. Everything rises and passes. It’s a law of nature. Change is constant around us and within us.

  4. Don’t always trust your feelings and snap judgements about others. We’re very good at crafting stories and beliefs in our minds with very little information and context.

  5. Every person is likely struggling with something. Be kind. Be helpful.

  6. Don’t buy something just to buy it. Accumulation of things will never lead to sustained happiness.

  7. When we speak openly about our challenges it can give others the strength and courage to do the same.

  8. Time is the single most important non-renewable resource we all have. Fill your days with what truly brings you alive, fills you with energy and allows you to grow.

  9. The only person you can change is yourself. It is nearly impossible to change other people. However, when they notice your own change, it might give them the courage or impetus to change themselves.

  10. Being a parent is 5x harder but 100x more enjoyable and fulfilling than I ever imagined. Love for a child is boundless. Caring for your child is the purpose of life.

  11. If you want to make progress on the things that matter most, you need to decide who you’re going to disappoint. It’s inevitable.

  12. Real trust and deep relationships can’t be manufactured or rushed. These are built over time through countless authentic and meaningful interactions and experiences.

  13. Traveling is single most effective way to learn about yourself, humanity and the world.

  14. Most of the time, family and friends don’t need you to fix their problems, they just need you to be there with them.

  15. We are all far more powerful, resilient and adaptive than we even realize. It’s never too late to change and remake yourself. We are all a work in progress.

  16. Equanimity isn’t suppression of thoughts or feelings but rather being ok with how a situation unfolds or how we feel in a given moment.

  17. Meditation is surest path to understanding yourself, your feelings, your thoughts and your perceptions.

  18. If you wait for the perfect moment or inspiration to learn a new craft or create something, you’ll never progress. Start now if it’s truly burning within you or else you’ll be exactly in the same place ten years from now.

  19. Listening with your eyes is just as powerful as listening with your ears.

  20. Living a sober life is vastly more enjoyable and liberating than society wants you to believe. You can have fun and be social without substances.

  21. Every single one of us has a different map of the world. So if you want to understand someone then you have to understand their map.

  22. Don’t force things. Apply the just right amount of effort but not too much.

  23. Being uncomfortable will take you to your edge and that’s where real growth and transformation happens.

  24. How you spend your time and your calendar reflects what you truly value in life.

  25. Pick your spots. We have limited time and our brains can only process so much. Focus is key. Choose wisely.

  26. A great teammate always puts the organization and its purpose ahead of their own self interests.

  27. Admit when you’re wrong and/or being an asshole. And when you are, learn from those experiences.

  28. You can’t be everything to everyone so might as well be yourself. Follow your values.

  29. All relationships, even the healthiest ones, are difficult and complex because most humans aren’t ‘compatible.’ The key to making them work is open communication, patience and compromise.

  30. You can likely learn the fundamentals any topic or craft if you dedicate ~100 hours. That’s not much time in the grand scheme of things. Immersion leads to progress.

  31. It’s not about the light at the end of the tunnel. It’s the tunnel. Show up every day and enjoy the process.

  32. Journaling for at least fifteen to thirty minutes is one of the most powerful forms of self care and therapy.

  33. You’ll never get what you don’t ask for or actively seek out. Go for it!

  34. Don’t expect to achieve very much if you spend your life trying to please others.

  35. Good physical and mental health is the single most valuable thing in the world. It starts with a good diet, regular exercise and ample sleep (7-8 hours).

  36. Long walks in nature are amazing for processing thoughts, emotions and important decisions.

  37. The best investment you can make is your own education. Never stop learning. The second best investment you can make is building your network through authentic and meaningful interactions. It is what you know and who you know.

  38. Sometimes you need to slow down to speed up or go backwards to move forward.

  39. Forgiving and making amends are brave and powerful acts that can help you turn the page and begin to move forward.

  40. Life isn’t perfect for everyone but we all have the freedom to choose how we respond to our circumstances. Don’t underestimate the power of faith, hope and positivity.

Parker Palmer On Vocation

I just finished reading ‘Let Your Life Speak’ by Parker J. Palmer. He’s an author, educator and activist focused on community, leadership, spirituality and personal growth.

The book is essentially a collection of Palmer’s essays about listening to your inner voice or true self, finding your vocation in life, crawling out of the depths of depression and finding the path towards meaning and fulfillment.

I found his essays to be deeply thought provoking and timely given I’m turning forty in October and wrestling with some big life questions. This book has helped me find some clarity by tuning into my inner voice, recognizing what gives me energy and asking myself what’s truly important.

There is one passage in the book that really struck a nerve for me. I wanted to share it with you in hope that it speaks to you as well.

“Vocation at it’s deepest level is, “This is something I can’t not do, for reasons I’m unable to explain to anyone else and don’t fully understand myself but that are nonetheless compelling.”

What is your vocation?

The March To 10,000 Hours

How long does it take to become a master at something? I first learned of the “10,000-Hour Rule” about a decade ago when I first read ‘Outliers’ by Malcolm Gladwell. The premise of this rule is simple: the key to achieving mastery in any skill or craft, is, largely, a matter of putting in the time and practicing for roughly 10,000 hours. Gladwell argued that legends like The Beatles, Bill Gates and others crossed this milestone before truly breaking out.

I’ve been thinking about the “10,000-Hour Rule” following a conversation I had a few weeks ago with a talented and thoughtful executive at a well known startup in NYC. This gentleman just turned thirty and is starting to think about the next phase of his career and life. Despite being very good at his job, he doesn’t feel like he has made an impact or developed real skills that are truly valued in the world.

He told me about Thomas Callahan, a bike builder in Brooklyn, who is the founder of Horse Cycles. Thomas makes about twenty custom steel bikes each year. His bikes are incredibly well made and beautiful. I can assure you Thomas has passed the 10,000 hour threshold building bikes. He’s a master craftsman.

My friend explained, “there’s something intoxicating about the idea of building something with my hands, delivering it to a customer, and then seeing that person derive happiness and meaning from that exchange.” I got the sense my friend desires to transition from his “desk job” to a new vocation that has a tangible impact on others. Thomas Callahan clearly has impacted my friend.

How does this story relate back to 10,000 hours? My friend just entered his thirties and is clearly contemplating what to do next with the next phase of his career and life. I don’t know what is the right answer and path for him. BUT I do know that he has the time to remake himself and master a craft if that’s what his heart truly desires. God willing he makes it to eighty, he has five decades remaining to devote to his craft. Five decades! That’s fifty years! The time no doubt will go fast but it’s certainly more enough to achieve mastery.

So what does the march towards 10,000 hours look like? Eight hours a day for five days a week gets you there in only five years. Seems challenging but doable especially if one switches careers. Here’s another combination: two hours a day for five days a week gets you there in twenty years. That’s the part-time path to 10,000. There is even a calculator should you want to go down that rabbit hole.

Here’s my point in all of this. We all have the ability to launch our lives in a different direction. We all have the ability to master a new craft. We all have the ability to bring our visions to life. 10,000 hours seems like an eternity but remember time is on our side for many of us especially if we get started today. Each of us can become our own version of Thomas Callahan if we’re willing to put in the effort, passion and of course the time behind a vocation that we truly love.


On Privilege

Last week, I published a blog post titled, ‘Decoding the Qualities of a Great VC.’ The spirit behind the piece was to spark a conversation about what makes a good venture investor and whether that can be predicted. It was generally well received until I saw this Tweet from Nathalie Molina Nino, CEO of BRAVA Investments, an investment platform that cares less about creating the next woman billionaire and instead backs businesses that create wealth for a billion women.

I immediately became defensive because I had good intentions in writing the post and felt I highlighted ‘universal’ attributes of great investors. Without giving it any thought, I quickly replied to Nathalie with the following tweet.

I then felt a backlash from a number of individuals including Katherine Gordon, Founder of The 3% Conference.

At that point, I became uncomfortable because my ignorance was obvious. Growing up in a predominately white upper middle class town in Massachusetts, I was indirectly taught that privilege was about wealth rather than race, gender, sexual preference, etc.. I incorrectly believed I wasn’t privileged because a) I was raised by an amazing single mother who worked two blue-collar jobs, b) I’ve earned an income since my early teens, c) I financed my college education, d) and I’ve worked hard to be self supporting for nearly two decades. It dawned on me through those various exchanges that I have been eating my own bullshit. What I began to quickly realize is that wealth is just one component of privilege and arguably the weakest one.

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Over the weekend I was fortunate to participate in my first “Medi Club,” a monthly gathering of urban-dwelling meditators. Medi Club is the brainchild of Jesse Israel who wanted to create a safe place for modern meditators that achieved three core goals 1) meditate with like-minded meditators; 2) discuss how meditation relates to issues like relationships, creativity, sex and work/life balance; and 3) deepen practice with new knowledge and interaction with the community. Here’s a little more context on what Medi Club is all about: ‘A Place for Modern Meditators.’ Last night’s theme was centered around transitions in life and work. This particular topic has been top of mind for Jesse because he’s in the process of finding a new path.

For many people, going through a career transition can be both exciting and scary. There’s so much unknown. What are people going to think of me? Can I survive without an income? What do I want to do with my life? Who should I talk with? What would make me happy? Who do I aspire to work with? How long will this take? So much is on the line. For many New Yorkers, a big part of our identity is tied to what we do for a living because it provides meaning and context in a dense city with eight million people. When our immediate existence is challenged, it’s only natural to feel anxiety and uncomfortable because there’s so much uncertainty. In my own career, I’ve found change is never easy but it’s a natural step in the process and it’s required to evolve into a better human.  

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