Being 40

In August, I turned 40. I have much to be thankful for; healthy and independent parents, a growing family, and interesting and intellectually fulfilling work. However, it was also bittersweet. I had a sore ankle, a sore lower back, and felt older.

As a husband and father, I want to be at my best for my family and be active with my kids and set a good example of behaviors to model. As I get older, I know my health is not going to organically get any better, and I need to invest in practices that improve both the quality and the length of my life.

Here are a few pieces of advice to myself for the next decade to help me grow, and live a better life. I fully expect, when I reread this in the future, that I’ll cringe and/or not adhere to these pieces of advice, but I’ll definitely try my best.

Enjoy the Journey

It’s not just about the outcomes (although winning feels great) and it’s about the people that you build bonds and the shared experience you have together. Enjoy the moments, no matter how small and be fully present with the people you care about (from The Power of Now).

When working with people try and be empathetic and kind and bring humanity and humor to every day interactions. When you think/feel something positive about someone, tell them even if the thought is fleeting. When you’re frustrated or angry, hold back and make sure you observe a pattern so you can synthesize and share productively.

I want to be mindful of this when spending time with my young children. It can often feel like “work,” but there are so many magical moments that if I am not paying attention, I’ll miss them.

Embrace Variety

I’ve learned that I am least motivated when I’m stagnant and that I’m most motivated when I’m learning new things and growing as a person. I don’t like doing the same things all the time and I get bored with excessive routine.

I like being at high-growth companies because this naturally leads to more variety in my roles and the nature of work changes with the company stage. I also like being at the cutting edge of technology. For example, working in crypto naturally lends itself to more variety given how fast the industry itself is evolving which makes it a good fit for my temperament. Given these biases I’m naturally inclined to run experiments and “explore” but should make sure and reserve some space for doubling down and “exploit” when the time is right.

Angel investing also helps scratch the variety itch as I get to meet interesting people and learn new things from them (often at the cutting edge). I plan to continue investing in startups as long as I’m able.

Be Consistent

Ok, I realize this is the total opposite to embracing variety but there are certain things that I know I need to be consistent about to achieve the compounding benefits of repetition and better daily habits.

An example of this is managing my weight which I’ve yoyo’ed with over the last decade because I struggle with consistency. without variety. I plan to try some new experiments like being consistent about tracking my food, but eating a variety of foods or consistent about exercising daily but increasing the variety of my workouts.

Being consistent applies to many other parts of my life too – a colleague, a manager, a husband, a father, a friend. People around me value consistency in temperament and values because it makes you a better collaborator and person to be around.

Take Some Off the Table

I’ve been investing and spending my time on risky pursuits (crypto, startups etc) for over a decade accumulating equity. Most of the gains can be explained by a Power Law Curve, and a few outcomes drive the overall performance. When given the option, I should take some money off the table even if it caps the overall outcome. A good rule of thumb is to take the maximum of 2x my original investment or 20% of the current value of the investment (Fred Wilson’s “Taking Money Off the Table” was a great inspiration). I also try not to have any single asset be more than 5% of my total net worth, but am not sophisticated enough about considering correlated assets.

Since the start 2022, crypto is down 80% and many growth stocks are down 65%. Most of my “successful” investments fell into these categories, and I would have benefited from taking more off the table.

In the Tao of Charlie Munger he talks about keeping cash on hand to bet big on extraordinary opportunities and I hope to put myself in a better position to do this in the future.

Look After Yourself

Great health is a gift but also needs focus and investment. I need to look after my whole self (body, mind, soul) better and this will continue to become more important as I get older. I need to prioritize things that fill up all these cups and deprioritize things that drain them.

When something hurts, stop playing the sport or working out. When I was younger, my ego would tell me to “power through” but now when recovery takes 10x longer, or I’ll be unable to exercise for weeks it’s really not worth it.

In general, being more mindful and knowledgeable of the point of negative marginal benefit is really important. It’s always better to stop before the point where you’re going to overdo something – eating, drinking, working out, watching tv etc.

There are times when it’s both fun and appropriate to overindulge and in those moments enjoy it and know that you’ll suffer for a bit in the future.

Time is Finite

More than ever, I realize time is our only non-fungible resource, and I need to prioritize intentionally to make sure I’m in control of my own schedule (check out the book Essentialism for more). I want to continue to prioritize spending time with my friends and family and doing something every day that is regenerative and gives me energy. We spend 90% of the total time with our parents by age 18, and I try to have longer periods of unstructured time with them. This graph of how we spend time as we age is interesting food for thought.

Writing is Refined Thinking

I’ve picked up writing in the last few years and really enjoy the practice. “Writing is Refined Thinking” is a quote from Stephen King’s book, On Writing. I love this quote and often find that concepts that are apparently clear in my mind are not clear when I try and articulate them on paper which often exposes gaps in my thinking.

Writing forces me to ensure that I actually understand my thinking and can explain it to others. It also allows me to share experiences and knowledge at larger scale and keeps my memory honest (no ability to look back with rose tinted goggles).

I have been neglecting writing for fun as work and family take up more of my headspace and time, but will try and write more (starting with this post) regularly.

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