Note to (past)self

you're on your own, kid.

Ernesto Bazan, Salsa Musicians Rehearsing, Havana, Cuba, 1997

Once upon a time, you were filled with grand visions for the future. You tried to strike out on your own, but quickly lost faith in your abilities. Instead, you joined a startup because you believed it was the best way to do something interesting, impactful, and fast. The early years were spent coming to the office at 7am and leaving at midnight. Every lunch discussion was about grandiose dreams of the future or the miniscule details of the present: could we create a new type of bank? Should the new object in the API be split into two? What about migrating the dashboard to this new web framework? You were thrilled by the tiny details of technology. You thought you’d stick around for about a year, but you were having too much fun with your new friends. The company was growing too fast and the dopamine hits were too addicting. You stayed. You were willing to trade autonomy for fast feedback loops. 

You were there when everyone-knew-everyone. You were still there when the era everyone-knew-everyone reached its end. You saw process and structure multiply sometimes too fast, sometimes too slow. You experienced the thrill of truly juicy victories shared with a team: the sleepless nights and uncertainty ending in new customers, sales deals, and launched products. You loved the discipline and the validation. You thrived off the pace. It was never enough chaos for you; the energy was exhilarating. You always wanted to go faster, faster.  

When you became a manager, you had your first stumble. You had your first few dramatic disagreements, which left you doubting yourself and feeling insecure. You redoubled your intentions in order to get it right, still going to the office early and leaving late. You said the hours were because work was too much, but you secretly wanted to avoid everything at home. You were hiding from your relationship. You thought about dating as a tolerance exercise, something to endure instead of enjoy. Work was where you could ignore the questions in the back of your mind, the whispers that “maybe this wasn’t right,” in your relationship that nagged you. You took the opportunity to pour yourself into something that felt meaningful and fun. Your ghostly self occasionally haunted your home, cruel in its indifference.  

When your mother became sick again, you dropped everything at work in an instant. Dropping everything helped you realize how much you had been carrying. In those moments of silence in the hospital, you realized how much you craved the agency over your outcomes that work offered. It was heaven compared to the bewildering questions of real life. You returned to work a week later. 

As the company scaled even further, you slowly distanced yourself from the decisions you used to help drive. You saw sacred company rituals get abandoned too early. You saw sacred company rituals get abandoned way too late. You climbed the mountain and started seeing the clouds. You started to see departures — both voluntary and obviously involuntary.

You realized the most important asset you’d take wasn’t the shares in the company, but the community of people who you’d probably follow throughout your life. You went to their weddings and their baby showers. You cried when they faced hard times. 

You realized the most important thing you had learned wasn’t all the tactical tips, but was the self-knowledge that you could work harder and learn faster than you believed possible.

You grew very quickly in the organization, but it came with a small sacrifice. You didn’t get to stay involved in the details and vision you loved so much. Your conversations turned from big hopes for the future and miniscule details of the present to organizational dynamics, the trappings of the work instead of the work itself. You went to trendy bars in New York and San Francisco to kvetch about VPs and re-orgs. On the outside, you were a lucky and successful employee who rose the ranks at a high growth company. On the inside, you were still afraid. You began to realize that it might be time for a new season of life.

You quit your beloved job. You ended your less-beloved relationship. You felt scared, risky, illegible, off track. But you were once again filled with grand visions for the future. You felt a desire to strike out on your own. 

Now, you are back to where you started, on level 1 of the game. This time, you are armed with your hard-won knowledge, belief in your abilities, and skill. Begin again.