A Year in Chicago: Reflections

About a year ago I moved to Chicago. In that time my life has changed completely.

In that time I’ve written 130 of these blog posts, sold my first company, launched my second, became the director of a startup training program, officiated a wedding, made new friends, completed my second year of marriage. A few lessons learned about life and notes-to-self:

1) You owe it to yourself to be uncomfortable. When we first moved here I was scared. The city felt so big, I didn’t know if my business would survive. The city has a way of shrinking, things have a way of falling into place. That’s where growth happens.

2) Density matters. There is power in continuously showing up, in person. Proximity to other people doing cool things, to coffee shops, to parks, to friends is power. You really miss out on that third dimension from behind your computer.

3) Chicago Dogs, a love story. I didn’t realize how good a hotdog could be until I lived in Chicago. I also didn’t know a city could have such a romantic relationship with a food like the hot dog - there’s something poetic about it (no ketchup allowed).

4) Public transportation can be a beautiful thing. It is the gauge of a functional, developed democracy; a great equalizer, a magnifying glass to see society, all varieties of people the top and the bottom, up close and personal.

5) I wish you would dream bigger. You really can just do things. The world is a museum of passion projects. Genius is abundant, courage to act on it is scarce. More than anything, the river boat architecture tour is a $40 education in the history of courage.

 6) Find a side hustle or hobby. Dedicate your life to a singular purpose, but find other ways to keep yourself grounded, creative, and blow off steam. The gym counts, hackathons count, poker or catan will do too. Avoid vices, get addicted to good things.

7) A city will teach you pace. Things move faster in the city. Decisions, conversations, opportunities. You either speed up or get left behind. I've also learned when to slow down, the importance of long walks, smelling the roses, letting your brain process life.

8) Money is just stored time. At least in startup land, it’s the ability to get from A→B more quickly. In the real-world maybe it’s better though of as stored mobility. Invest your dollars young into things that compound (experience, appreciating assets).

9) Your network is your net worth. More value than money is connections, especially in your twenties. Connect with people who can help you get where you want to be. Surround yourself with good mentors and people who make you a better person.

10) Marriage is the start, not the goal. I wish young people would get married earlier (I sound old yes). There is nothing like committing yourself to someone and them to you. Best friend, biggest fan, partner in crime. It’s a cheat code to a wonderful life.

Just a few thoughts for now, what do you think? Maybe I will revisit after year 2. No plans to leave we are just getting started.

Peace,
Ramsey