Welcome 2021! In lieu of a New Year’s Resolution I want to spend time to reflect on the course my life has taken and explore how I could’ve handled situations better. Over the next few weeks I’ll go over one mistake I made each of the past five years that hurt my career or other aspects of my life. I’ll describe what led me to the incident, how it affected me in the short term, and how it impacted me in the long run.
Posts in this series:
- 2016: I Kept My Return to Game Development a Secret
- 2017: I Almost Started a Sports Bar (and Put My Friend in Financial Trouble)
- 2018: I Let Personal Finance YouTube Channels Take Over My Life
- 2019: I Overcommitted
- 2020: I Failed to Be an Ally in a Pivotal Moment
2020 in Comparison to Other Years
Despite 2020 being chaotic in the outside world, the year provided me an opportunity to calm things down in my personal life. I’ve come to terms with what my limits are and I’ve learned to work effectively within those limits. I’ve distilled the various aspects of my life down to the elements I find most enjoyable.
I can watch sports just for the sake of it; I don’t need to crack jokes about the game to gain followers online. I have a financial plan that doesn’t require me to become an investing supergenius like Warren Buffet. I can enjoy learning about a topic without turning it into a business all the time, because only one of my businesses will matter in the end. I still have ambitious goals, but I’ve allowed myself to take them on one at a time.
So if 2020 was all about cleanup, did I get into any new messes? I’m fortunate to say I avoided the level of self-sabotage I got into in the past. But there were still flubs I made that year.
For most of the year I would’ve said my biggest regret was not attending the nyc.rb Meetup in January. My company hosted the event and I was asked to help with event but declined. Who knew that was my last chance to meet people before the world was shut down? That being said, there’s no way that was my biggest mistake in 2020.
I could also discuss how I left my team astray while my manager was on parental leave later that year. There were things I could’ve done to make the team work more effectively, like communicate the urgency of certain tasks. However, I’m still unpacking lessons from that experience, so I won’t be talking about that either.
Politics in Tech
Instead, I’ll talk about another professional event that happened in 2020. I’ll leave the identity of the group a secret, but they held an online discussion that summer on how improve diversity and inclusion in the tech industry. Attendees were asked to watch a video in advance and come to the meeting to discuss their reaction to the video and the topic of diversity in general.
I came into the event not really thinking much about it. The tech community in New York has largely been in support of diversity and inclusion initiatives even before 2020 happened, and I assumed this talk was going to be more of the same. However, this group included engineers from other parts of the country, some of whom had different sensibilities. Because of this, the event ended up being something completely different.
I think most of the problem came from the video we were asked to watch. The title of the video was a bit clickbait-y, so it probably set a bunch of people off right away. My issue with the video was that there was a lot of “both-sidesing” on part of the creator which muddied our discussion. Instead of bringing up socioeconomic issues, the video was more about cultural attitudes that minority groups had. While I agreed with some of the takeaways (e.g. blacks shouldn’t bully other blacks for being nerds), some attendees doubled down on this aspect of the video. The conversation was supposed to be about the things we could do to achieve equitable representation in tech, but it became apparent there were attendees who instead wanted to place the blame on minorities‘ lifestyles for their economic condition.
Many people were disappointed with how this event turned out. This would be the part where I say I should’ve stepped in and reclaimed control over the conversation, but let’s be real here. I didn’t prepare myself to engage in a debate, and any ideas I have on how to achieve a better outcome are ultimately untested. If knew the event was going to be such a farce I would’ve just cancelled it altogether.
Social Change in Relation to Life Goals
Since this event I thought long and hard how to tackle social issues in the future.
First was a reflection on my overall approach to social and political issues. I went over it in detail during my series on Extreme Ownership, but it boils down to the following:
- Be honest and upfront about what you believe in.
- Any time you obscure your opinion, you risk the following:
- You hurt your allies because you want to support them but say something that attacks them instead.
- You help your opponents because you weren’t direct in expressing your opinion.
- Everyone else is confused because they don’t know what point you were trying to make to begin with.
In terms of substantial action, I’ve come up with a multi-phased plan:
- Send monetary support to organizations I want to have succeed. I’ve already allocated a part of my budget toward this activity, and since my free time is spent being a creator on the Internet this is realistically the most I’ll do.
- Once my entertainment franchise is safely established, start making my political views public. I must act judiciously so that this only consists a small portion of the content I create, to avoid being pigeonholed as a political activist.
- Once I have enough resources, support businesses and people I like by buying real estate to rent out at a discount, providing business loans, or engaging in venture capital.
I have strong feelings on how society should function, but I’ve been hesitant to express them throughout my life. Unlike my peers who are more willing to share their political views, I feel like I have to play by a different set of rules because I will become a public figure in the next decade and mistakes will be more costly at that scale. However I must remind myself that the overall result, and not reputation by itself, is what matters and I must always evaluate my contribution to society under that lens.