i hope this finds you well — letter one

This is the first installment in a series of letters written to my son, to be read when he is my age. #

Self reflection has the utility of masturbating.

This week has been the closest I’ve been to wanting to end my life. Not becuase anything particularly bad has happened but because I know its inevitable that it does. All of history confirms this truth.

I looked up the 20 most famous people born in 1850. I don’t know a single one of their names but their lifespan catches my attention.

Robert Louis Stevenson 1850–1894

Guy de Maupassant 1850–1893

Joseph J. Dowling 1850–1928

Robert Brower 1850–1934

Lord Kitchener 1850–1916

Lafcadio Hearn 1850–1904

Of the 50 people on the list of “Famous people born in 1850”, fourteen lived into the 1920’s and 8 into the 1930’s. The oldest in the Top 50 lived one day shy of her 89th birthday;

Theo Mann-Bouwmeester

Theo Mann-Bouwmeester was born on April 19, 1850 in Zutphen, Gelderland, Netherlands. She was an actress, known for Judith(1923), Pro domo (1918) and Frauenmoral (1923). She died on April 18, 1939 in Amsterdam, Noord-Holland, Netherlands.

No one made it to 1940.

My father was born in 1950, and given his passage into the new century, he’s already beaten the statistical odds of most of his human counterparts. He’s alive into the 2020’s. This year he’ll be 72 this year.

We can learn alot by considering our lives using the context of the lives of the men that lived before we did. Much like the humans who went before him my dad probably won’t make it to 2040 which is 90 years after his birthdate. Even thinking about him as a 90 year old man puts a lump in my throat because watching the elderly live is, ironically, the most potent reminder we have of the looming inevitability of death. Death is most pungent on the breath of those whose bodies are breaking down. They can’t help it. Even if they’d like to stay alive, they can’t hold back the wave.

Today I am 33 years old. Assuming I live to 1940, I will turn 52 years old. When my dad was 52, I was 14 years old. I remember it well. I was a freshman in highschool and Cara Brown was probably the most attractive girl I’d ever met. She was a senior and she took enough of a liking to me to entertain conversations in the hallway. I wasn’t even on the social hieararchy. Too short for basketball. Too small for football. Not skilled enough for soccer and just too lazy for track and field. I probably could have been a decent distance runner. Maybe even good enough to get a scholarship to a D3 school if I trained hard enough.

I was extremely interested in clothes and fashion however. I worked extremely hard to put together outfits that wouldn’t make me look as poor as I thought my family was. It turns out we weren’t poor that poor they were just frugal and 2 years later they built a 3,700 sq house on 3.5 acres in a suburb of Rochester, NY.

As a man whose love of clothes has evolved into a love of watches and sports cars, I’m not entirely sure whether this obsession comes from my soul or is merely a response to the biological need to signal my sexual availability by seeking attention. In either case, my love for clothing played out through experimentation. I’d shop in the womens section for clothes that fit more like offerings on the runway. In 2002 Italian men were seen as the pinnacle of male style. Sprezzatura is a term that essentially embodies the italian approach to both life and style. It loosly translates to something like casual luxury. As I tried to replicate this style on the racks of J. Crew and Goodwill, my dad never said a word. Sheer tops, blouses, skinny jeans. Today, it wouldn’t be as unusual but if you look up picutres of how people dressed in 2002, it’d be more clear why an interest in skinny jeans was unusual for a young straight boy.

My father never said a word or treated me differently or even brought it up to be honest. In retrospect there are some outfits I wore where I wish he. The reason that time period was so significant has everything to do with our innate desire to make our fathers proud. As a black boy with a black father, I didn’t know that my experimentation wouldn’t trigger disapproval.

I honor my father for accepting me completely as I experimented with who “me” was and I honor myself for exploring it publically.

This year, 2022, I’m at a crossroads. I’ve spent the last 6 months living with my sister and her family in Nashville TN and on Monday January 3rd, I’m leaving here for either California or Texas. San Francisco is where startup culture is HQ’d however moving back to Austin isn’t a terrible option for someone who is entrepreneurial. It’s called Silicon Hills for a reason.

Life is about solving problems. In your career, you will be compensated according to your ability to solve problems and in your personal life, the problems you are able to overcome will define your self confidence and sense of worth. I don't know whether this is “the way it should be” but I’m fairly sure this is the way it is and so this year, I will take the most significant steps I’ve ever taken toward solving our financial problem. I say ours because if I did not take this year to try and solve it, you would inherit it. Money is not everything but it is the power of choice and the options (and creativity) would absolutely be constrained by your access to capital.

My goals for this year are not lofty. Many people have done them but they will be unbelievably difficult because they will require me to let go of things. Let go of seeing myself as someone who has no influence. Let go of seeing myself as someone who no one actually cares to hear from. Let go of seeing myself as someone who cannot manage large sums of money (even if large sums don’t come this year, a lack of confidence in my ability to handle millions will lead to my self sabatoge while managing thousands). Let go of seeing myself as someone who is great at first impressions but cannot connect deeply over time.

Here are the actual goals:

  • Serve first 100 customers
  • Establish social media presence and reach 100,000 people
  • Get a UX job at a FAANG company
  • Get first 1,000 Youtube Subscribers
  • Write 52 blog posts
  • Produce 1 product I’m proud enough to share with Ben Laws
  • Spend 1 week with DJ alone
  • Learn HTML and CSS
  • Make atleast 1 big bet on the future (crypto, metaverse, NFTs)
  • Attend 1 in person conference for Startup Founders

This year, I don’t want to get better through self-reflection and going deeper into myself. This year I want to get better by engaging with the world around me and discovering who I am and what my limits are in light of the world I’m living in.

Time is too short.

Yesterday my dad asked me when I was going to get him those things I promised him when I was a kid. I told him if we were on Facetime I could have walked him into my room and shown him where I’d written about that exact subject hours earlier in my journal.

Wanting to make your father proud may not serve you towards developing the independence needed for manhood, but it does serve as a motivating force.

What will make my father proud is watching me find my own way and, as a father, what will make me proud is watching you find your own way. Becoming a man requires you owning your own consequences. Being a man that I’m proud of requires you being awayre of your decisions.

We haven’t met yet but you can’t imagine how much I love you already. There is no limit to what I will do for you and if you’re reading this, and there’s something you need (physically or emotionally), just ask.

If you, then, though you are evil, know how to give good gifts to your children, how much more will your Father in heaven give good gifts to those who ask him! — Matthew 7:11

your father and friend,




UX/UI Product Designer | Tailor | Slowest cyclist south of the Mason-Dixon Line.

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Chaz L Day

Chaz L Day

UX/UI Product Designer | Tailor | Slowest cyclist south of the Mason-Dixon Line.

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