Leo's Letter // Entering A New Era
Not the typical "turning 30" post
Hey, it’s great to have you.
I’m back after a period of highs and lows during my ongoing exploratory phase.
What I’ve Been Up To
I started my funemployment with optimism, excited that I could finally have the time to try everything on my bucket list. Wouldn’t it be great to travel, do some consulting work, experiment with business ideas, and look for jobs with all this newfound free time?
Turns out it’s not that simple. I spent some days doing too much and wearing myself out. I then had to spend a few days doing very little to unwind. Every time I fell off, it took as much force as rolling a boulder up a hill to get back on track. Sometimes I would plan for a few days filled with activities, fail to start, fall behind, and feel bad about it. My excuse was that I would start the next day, but that time would come and I still wouldn’t do anything and feel even worse. The cycle would repeat for a few days until I changed my environment and got back on track.
It’s ironic that I was oftentimes more stressed in this period of self-imposed deadlines than I was with external ones.
Things improved when I decided to focus on only one thing at a time. I spent most of the past few weeks focusing on the job search and established a routine where I would spend the mornings focusing in this area so I felt that I had spent at least part of my day in a productive manner. I joined a peer-led job search council and have been following the steps outlined in the book “Never Search Alone” to determine which roles and industries I wanted to focus on and how to position myself. I built momentum by reaching out to friends, former colleagues, and other acquaintances - many who have been helpful in my journey and made me feel that I was not alone in this search.
While I’m still in the process of landing a new role, I feel invigorated by the support I’ve received and my confidence rises the deeper I go in my explorations in the roles I’m targeting.
Lessons From Turning 30
Now onto the heart of this post: I recently turned 30 and felt that it would be good to share some observations as someone living in the NYC area and has noticed some significant changes from my early and mid-20’s.
People move on
Large cities are transient and people move, both literally and physically.
People move out of the city for various reasons: for work, to be closer to their families, or for more peace and quiet (even me, having moved from Manhattan to Jersey City).
Even when you and your friends are in the same city, you might not be in the same life stage. You may be single and your friend group may be mostly couples. Some couples might even have kids (a perfect valid reason for why you haven’t seen a friend in a while).
Lastly, people’s interests change. What might have been fun a while back may not be fun anymore, and it’s ok. There was a time and place for that.
All of this is natural progression of growing up.
Identity without labels
I remember my senior year of college where all of the students would ask each other what they would be doing after graduation. I had felt a sense of FOMO because I wasn’t going to be working in a prestigious job like investment banking or consulting.
On the other hand, I remember the time I was working in venture capital and the frequent inquiries I would get from founders wanting to pitch their startup, vendors wanting to work with the portfolio companies, and other requests. I felt like I had in a sense “made it”.
Now that I don’t have a full-time job, it took me a while to adjust. I felt some hesitation going to networking events because I didn’t have my job title.
Eventually, I got over this by focusing on what I could bring to the table over my label. I approached events with curiosity, without any expectations for networking and this helped me ease into going to events. I’m even hosting my own event in early December and I know those who are going know me for who I am versus what I appear to be.
Everyone has their own pace
I’ve been both “ahead” and “behind” in my career. But the only point of comparison should be oneself.
In fact, the further out you go from school, where everyone starts off, the more variables come into play. Some people got to where they were by being at the right place at the right time. Others chose the wrong company, or an industry that was too early for its time. Personal events happen. All this to say that there’s a lot that can’t be controlled, you never know the specifics of one person’s journey.
I can only measure my progress one day at a time. Did I do what I set out to do? Did I challenge myself? If so, then I did well. For example, I had to re-learn SQL for a job interview, and even though I didn’t get the job, I passed the SQL test and for that I feel accomplished.
The War of Art covers the concept of “Resistance”, the force that holds you back and must be overcome on a daily basis. Resistance is the only one to beat.
Always produce
I’m still figuring things out right now but I’m writing as a way to help me do so. This post was largely motivated by catch-ups with a few friends who mentioned writing, so thank you to those who encouraged me.
Paul Graham, founder of YCombinator, once said “Always produce will discover your life's work the way water, with the aid of gravity, finds the hole in your roof.”
Here’s to consistently overcoming resistance to produce and figure things out along the way.
P.S. - I’m making more efforts to keep in touch with friends old and new. I’ll be hosting a holiday party at my apartment in Jersey City on Saturday, December 7. If you’d like to come, send me a message (open invite)!