Ten Life Reflections from 2020

Stillness at Lake Merritt after a day of reflecting

In my 2019 reflection, I mentioned how 2019 was one of my hardest years personally and professionally.


As you can imagine, the momentum that came out of that reflection sputtered quickly into early 2020, forcing a whole new set of life adjustments. While it was a series of tough times, there are also some fun things retrospectively that happened in 2020:

  • Chatted regularly with a therapist for the first time
  • Took the longest hiatus from drinking since before 21 (almost 3 months)
  • Lost close to 30 pounds in peak quarantine (Mid-July)
  • Started a newsletter and actually shellshocked my imposter syndrome by growing an email list to hundreds of people
  • Celebrated graduations, birthdays, work anniversaries, and more digitally
  • Reconnected with friends across the country and met lots of incredible new people through Twitter and the OnDeck fellowship (some whom I may never meet in person but still feel a light kinship with nonetheless)

As I had done last year, wanted to share some reflections that come to mind from this year:

  1. True work-life balance involves drawing your own boundaries and giving yourself permission to fail at work without it impacting self-worth. One of the largest shifts we saw in COVID was the blurring of boundaries — there was no set time to commute to an office, so you could effectively log on and off at your leisure. Even after weeks of the company insisting we take care of ourselves, I still had trouble peeling myself away from work. Removing emotional attachment to validation was a big part of meeting the company halfway. I wrote more about it here.
  2. Your ignorance is useful to people. Be comfortable with learning in public. When I first decided I wanted to write a newsletter, I struggled with the idea that my domain and functional expertise in marketing was something people widely wrote about. Instead, I decided to take a new approach: effectively researching topics in order to write about them, often leading to incomplete hypotheses but nonetheless fun ones. There is a liberation in acknowledging that you might not know everything.
  3. Simply living in the present, practicing patience, and showing gratitude is productivity. COVID-19 forced us all to redefine productivity. In the first 30 days of quarantine, I read far less books than I had hoped, abandoned my daily writing practice almost immediately and hadn’t started any businesses or chipped away at any larger abstract life purpose. But I slowly realized that some of other work — identifying emotions, dissecting situations, finding emotional fulfillment, and finding gratitude — was all productive in its own sense. I wrote more about it here.
  4. We are not working from home. We are at home during a crisis trying to work. Inspired by this tweet and something I couldn’t stop thinking about. When people spread the gospel of how amazing remote work was, I couldn’t help but shrug. Being out of an office hardly reduced the distractions and exigencies of the world. It only served to open my mind more. That unavailability was not a sin, but a circumstance.
  5. Focus on process, not outputs. If nine months of remote work opened my eyes to anything big, it was the realization of just how many inputs needed to judge someone’s output are lost. Sean Blanda wrote a piece that caused me to reflect on this a lot: With the removed context of a real-life office, your team’s output is difficult to individualize for your manager — especially if work is done in private DMs or one-on-one Zoom calls. Do the other team members appear to enjoy working with this person? And, if they are struggling, is it due to a lack of effort/focus or something outside of their control? It caused me to reshape my curiosity around my colleague’s contributions — and also drove a healthy skepticism around optimizing remote work environments.
  6. Golden insights often come from dumb questions. Nobody loves to ask dumb questions. Why do we brush our teeth? is not necessarily a question you want to see yourself asking after 20+ years of indoctrinating yourself to do so. But I find that some of the most interesting observations of the world come from pausing and asking ourselves why things exist — this was the entire premise behind my writing this year. The insights often make the dumb questions smarter in retrospect. Why do we boycott things? is a seemingly inane question. Writing about it made here opened my brain to a whole new layer of psychology behind boycotting. But more than that, it motivated me to continue asking dumb questions.
  7. It’s okay to love a hobby the same way you’d love a pet. This is a quote from a piece by Molly Conway on the trap of turning “hobbies into hustles” and a philosophy that resonated with me a lot. The full sentence she embellishes is here: “It’s okay to love a hobby the same way you’d love a pet; for its ability to enrich your life without any expectation that it will help you pay the rent.” We don’t have to monetize or optimize or organize our joy. I began using TikTok frequently during quarantine and it was the manifestation of this, a joyful hobby that I had no plans to grow or focus on beyond that. A cathartic and fun escape.
  8. Your lived experiences can’t always decide your passions. There’s a quote I really love: “Education is the progressive discovery of your own ignorance.” What it effectively gets at is that there is no way we have a full enough picture of the world to understand what we love. What we love today could change easily tomorrow, simply because there is magic in things we haven’t yet experienced. There were moments of serendipity, anger, and discovery I found during the pandemic that I couldn’t have imagined finding in the 20+ years before that. When people tell you to follow your passion, follow your curiosity instead. Your curiosity is inspired by your lived experiences but fully malleable enough to move past them as the world evolves.
  9. Being an ally doesn’t absolve you from systemic injustice. One harsh realization I had this year was unlearning biases — the realization that — even after years of considering myself a nice guy who was hardly complicit in racial injustice, I found that it was impossible not to be. There is no meritocracy in plain respect. Sure, I didn’t support saying the N-word, condone blackface, or support anti-immigration policies. But, I had to admit to myself that I hadn’t once thought about education funding from property taxes, spiritual bypassing, or discriminatory lending. I hadn’t thought deeply about the role of paternalism and have definitely unintentionally prioritized white voices in some areas as experts. I wrote a brief reflection back in May here but it’s a quote from author Scott Woods that continues to stick with me: “While I agree with people who say no one is born racist, it remains a powerful system that we’re immediately born into. It’s like being born into air: you take it in as soon as you breathe. It’s not a cold that you can get over. There is no anti-racist certification class. It’s a set of socioeconomic traps and cultural values that are fired up every time we interact with the world. It is a thing you have to keep scooping out of the boat of your life to keep from drowning in it.”
  10. Nothing you create for the first time will be that great. Create more anyway. If there’s one thing I realized from talking to lots of writers and assessing my own start to writing, it’s that we spend so much focusing on the right intersection of good art and finding the right audience. Important conversations to have, but ignores the reality that just by creating something, you’re in the 1% of people who have tried that thing. Finding fulfillment in creating is hard. Remaining consistent over time is hard. So few people attempt to do the same thing more than ten times. When you create, focus on having fun. Create things, get them off the ground, let them fall, and create again. Create to the point where you can add “creator” to your identity and nobody can take it away from you. This quote by Elizabeth Gilbert hits home: “If people enjoy what you’ve created, terrific. If people ignore what you’ve created, too bad. If people misunderstand what you’ve created, don’t sweat it. And what if people absolutely hate what you’ve created? What if people attack you with savage vitriol, and insult your intelligence, and malign your motives, and drag your good name through the mud? Just smile sweetly and suggest — as politely as you possibly can — that they can go make their own fucking art. Then stubbornly continue making yours.”

Whatever this year brings you in reflection, I hope it’s equally nourishing. Happy New Year and see you in 2021!

Growth @Livongo • Bostonian • Fan of sports and quirky theatre • Marketing Nerd • Weekly reads http://mindmeld.substack.com ✍️

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store