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Reflections on 40


I turned 40 years old a few days ago. Leading up to this birthday, I spent a lot of time thinking about what it meant. Was it a midlife crisis causing me to think so much? Was it simple ruminations on my life to that point? I don't know. However, what I do know is that leading up to my 40th, I began to drink from the cup of pessimism. Considering the ages that my grandparents passed away, I began to dwell on what I had convinced myself as fact–half my life was gone.

But I don't know that. I could die tomorrow. I could live to be 105. That is the beauty of being human. We simply do not know. So, when the day arrived, my mental state had changed 180-degrees. I was excited and energized. As a part of the Farcaster community*, I posted a simple AMA to celebrate my birthday. The response was overwhelming and the thoughtfulness of that community made me think deeply about my life, where I've been, where I'm going, and more. So, I thought it would be nice to aggregate the questions and answers here in an abridged format.

*Farcaster is an alternative social network, similar in style to Twitter, but with open data thus making it easy for users to use a variety of different apps instead of one single app.

In no particular order, here are the questions and my answers.

What's one accomplishment you're proud of from your 30s?

Cop out answer would be raising my kids and being a good dad. But I’ll go with learning to code and launching Graphite Docs.

I said it was a cop out answer, but I am incredibly proud of the way I have been there for my family despite working demanding jobs, starting two startups, and spending 3 months in a startup accelerator.

What is something you no longer believe in?

There are a lot of things I no longer believe in, but the one I kept coming back to is that you have to do everything yourself because no one is going to help you. I still struggle to ask for help, but I know there are tons of people who are happy to help.

This question gave me a lot of pause and I took a few hours to answer it. It helped me realize how many times I've changed my opinions on things in the last 20 years. And that's a good thing.

What did you wish you knew when 30?

I wish I would have known how far pulling at threads could take me. I had only started pulling then. I would have pulled harder and pulled more if I knew.

This was somehwat of an abstract answer, but what I meant was that I grew up believing I needed to go to school, get a job, work long hours, and climb the company ladder. I didn't know that I could explore creativity and do things differently that would eventually lead me on the path I am currently on. If I had known this, I would have started experimenting earlier.

If you had to wipe all of your memory but keep only one concert you attented, who was playing, where, and what did it bring to you?

Either Carlos Santana in Tucson when I was little and hated it because I can now appreciate how special that was or Breaking Benjamin in Dallas with my wife because it was our first concert together.

I honestly haven't been to many concerts in my life, and maybe that's a regret I can rectify in my 40s.

Does 35 feels like long time ago?

In some contexts yes. When I think about starting my last company, it feels like a million years ago. But when I think about my kids, 5 years ago seems like yesterday.

The pace at which life passes you by is both slow and fast at the same time. The accumulation of knowledge can happen quickly but feel like it happened over a very long time. On the flip side, children grow up faster than time suggests.

Who's your favorite poet? Or, if you don't have one: what does poetry mean to you?

I’ve only recently started trying to get back into poetry. Robert Frost was my first exposure as a kid and helped me love writing. Kaveh Akbar’s book Calling a Wolf a Wolf is my most recent poetry purchase though.

I can still remember sitting in class when I first read Dylan Thomas's Do not go gentle into that good night and feeling how that poem, stacked upon everything I had read from Robert Frost, would forever shape me as a writer. I don't read as much poetry as I should, but when I do it sticks with me.

If you could do over ages 35-40, what would you do different?

Only thing I might have changed it keeping Graphite Docs up and running for free instead of shutting it down because I couldn’t find a path to revenue. Other than that, age 35-40 was filled with really good decisions and outcomes.

I surely made bad decisions, but the ones I can remember led to lessons I wouldn't give up for the world. Contrast that with the bad decisions I made in my teens and twenties, and I'd say these last 5 years were filled with strong decision-making.

Do you feel young?

I feel younger than ever in everything besides my bones. Mentally, I feel incredibly young and like I’m just getting started.

Arthritis runs in my family, so it's hard to escape bone pain. But exercise keeps it mostly at bay. Playing baseball and basketball with my kids also helps keep me feeling physically young.

What are you looking forward to the next 40 years?

To continue making things. I want my brain to be as sharp as my grandfather’s was his entire life. He kept sharp by writing and researching and creating in his own ways.

My grandfather passed away earlier this year after having a stroke. The thought of him losing his mind, which was sharp as ever all the way up until the stroke, devastated the family. He spent his life learning. In his work, he was a chemist with dozens of patents to his name. In his retirement, he was a writer and a researcher with an appetite for knowledge that continues to inspire me even though he is gone.

How are you feeling?

Happier and healthier than ever.

This is 100% true. I remember one of my co-founders at my last startup asking me to rate my happiness a few years ago. When I rated it an 8 of 10, he couldn't fathom that and didn't think I was being honest with myself. This makes me sad because I know what it feels like to be unhappy. Before meeting my wife, I was an unhappy and angry young man lost in a world of confusion.

Gonna shave & see what she says?

Definitely not going to shave! I wouldn’t recognize myself.

This one made me laugh because I assumed it was a follow-up to a separate conversation I participated in on Farcaster about growing beards. My wife is an outlier in that she loves my beard and doesn't want me to ever shave. I've had a beard for my youngest son's entire life, so it's part of my identity now.

What would you advise your 30 year old self to not do/remove, to start doing, and to keep the same?

1. Don’t live in a place you hate (DC was a horrible experience for my family)
2. Take fitness seriously (I didn’t do much more than run until the pandemic)
3. Being home as much as possible for my wife and kids

In 2013, my wife and I moved across the country with our oldest son (who was not even 2 at the time). We left the desert of Tucson, AZ and I took a job that helped propel would would eventually be a career in tech forward in Washington, DC. However, I didn't get a raise. The cost of living difference nearly destroyed us if not for the grace of distant family who let us bail on our first lease and live with them rent-free for a few months. Combine that with the mentality difference of people in DC compared to Tucson and it was a difficult time for me and my family.

How 40 is different from 20 and 30?

I feel like more of a novice at 40 than I did at 30. At 20, I thought I knew everything.

When you let go of the concept of expertise, you learn more. And you learn more broadly. I recommend reading Range by David Epstein.

Do you have any expectations for yourself or for the world?

The only thing I expect of myself is to be a good husband and a father. However, I hope to also create things that make me and others happy along the way.

Making things that make me happy is enough. However, if one or many of those tings touches someone else and makes them happy, all the better.

If you have advice when you 20, what is it?

The advice I would give to my 20-year-old self would be to learn more. At 20, I (like most people that age) thought I knew everything. Now, at 40, I realize I'm always going to be a novice and that's a good thing because it encourages more learning.

Again, realizing that expertise is a false goal helped me embrace the process of learning and to learn much more about a wider range of subject.

This was an insightful way for me to celebrate my 40th birthday. I hope by writing this down I will be able to look back on this post years from now and recognize how special life is in general and how special my life is. Thank you to the Farcaster community for asking great questions.