My 2019 Review

In 2018, I started a new habit of writing an end-of-year review as an excuse to pore over my various self-trackers artfully disguised as a thoughtful reflection upon the year. You can find last year’s review here and be the judge of that.

However, I did hit publish one hour before midnight this year, so I consider 2019 a resounding success. Writing is never perfect, and I had probably written 80% of the substance in 20% of the time anyway (~ten hours).

Table of Contents

• On writing
• On reading
• On building
• On teams
• On identity
• On relationships
• On fitness
• Wrap up

On writing

I did far less personal writing this year than I wanted to. But ironically, from a professional standpoint, I may have written TOO much. After all, my co-workers call me a documentation fiend. Nothing excites me more than a clear and concise write-up. What’s funny to me is that our current level of documentation is, at best, the bare minimum at Amazon. I guess we’re products of our environment.

One lesson I learned this year- documentation is undoubtedly scaleable but not always the right tool for the job. Let me give an example.

Say you want to onboard your first product manager onto the team. An important part of onboarding is helping this product manager understand the company’s high-level, multi-year product vision (future) and the key decisions we made that led to today’s product (past). So we have two documents: one is a timeline of the company’s history (past), and the second is a deck of our company’s 2020 strategy (future). We assume the new hire can learn most of what she needs to know by reading these two documents and then asking us questions. Unfortunately, that’s not quite right. It’s a classic example of the curse of knowledge.

In this case, the most effective tool was a hour white-boarding meeting in which the new PM drives the discussion with questions. Why? Because in-person communication provides those nuances like body language, tone, the slight nods of agreement, the puzzled looks, and the inevitable random tangents that help an individual digest complex concepts. Documentation here should be used as a supplement and as a reference after the meeting when the new hire is post-processing the information overload.

I also realized that most of my professional writing is really written for me as the audience. My co-workers ask all kinds of questions. Half the time, I don’t remember the answer off the top of my head and I reference the documentation I’ve written. It’s immensely helpful for me, but not necessarily as helpful for the inquirer to pore over. In other words, writing is one of many tools for effective communication, and it’s an entirely valid use case to write documentation for yourself.

On reading

I only managed to read nine books in 2019, so we might qualify that as a failure. For reference, my Goodreads goal was 30.

I’ll point out a couple things I’ve learned about my reading in general. First, my purpose for reading splits cleanly into two buckets: entertainment and education. Entertainment can be consumed anytime, anywhere. Educational reading, however, is incredibly context dependent.

I’d argue that reading most educational books is worthless. Don’t get me wrong- the pursuit of knowledge is a worthy endeavor. But if the purpose is to learn applicable, long-term knowledge, then I would say I’ve failed to accomplish that with most books I’ve read, and would therefore retroactively consider reading them as an act of entertainment. I want to frame this is a miss on my part as the reader, not on the author or the book. I even take copious notes and review them periodically. But there weren’t immediate applications through which I could solidify the knowledge- it wasn’t the right time. One of the best books I’ve ever read is about space and the universe. Objectively, I learned a lot, but there’s unsurprisingly minimal application to my life.

So if I could reframe that I “only” read nine books in 2019, I would say that I read four educational books, and that it was in fact the perfect number. I’m happy with reading less if I can apply what I learned from what I DID read.

There are the four books along with the key questions that were answered:

1. The Everything Store- How do a handful individuals shape the culture of a company? How is a behemoth organization able to operate like a startup? What were the key turning points in the company’s history?
2. Range- What are the environments in which a generalist or specialist is better suited? What are the current and future trends that will change that? How many instruments and sports should I force my future kid to participate in?
3. High Output Management- What does it mean to be a manager? What are the highest leverage activities you can be doing as a manager? What makes a good manager, and in what situations?
4. Bad Blood- What are factors that incentivize companies to cut corners in the pursuit of growth/success? How do people get coerced into doing things they know are bad/wrong? How should I NOT treat other human beings? How do small lies snowball and turn into far bigger lies?

On building

Year one of the company known as Persona is in the books. We have a long way to go, but raising another round, undergoing a re-brand, bringing on twenty incredible teammates, getting rave reviews from customers, and overcoming growing pains are positive signals that we’re building something enduring and important. If the definition of success is a successful exit (for what it’s worth, that’s not my personal definition of success), we’ve 4x’ed our chances of success. On the other hand, we’re still facing an 88% chance of failure!

There are two main tracks on building that I think about:

1. Building a startup: This year was about becoming market/industry experts, formulating product and go-to-market strategies, and building a high-functioning team. Building a great product is informed by a cohesive strategy, which is informed by a deep understanding of the market. As the year went on, it was clear we made significant progress. For example, in a couple minutes, we can discern a prospect’s problem and recommend a solution. Another example, we defined clear target segments and use cases. We haven’t had trouble finding world-class talent, and fingers crossed that we never will. Fun fact- we thought we would have eight people by the end of 2019. The challenge has been making sure everybody is aligned and moving in the same direction while maintaining our insane speed.
2. Building a product function within a startup: This year was about building out the function from scratch. Early in the year, I started moving into a product role. It wasn’t an easy transition, but it was one that I had envisioned since I joined. I knew I had foundational skills and experience, but I still didn’t know what I was doing. Despite all the roadmaps, prioritization discussions, competitor research, etc. I still feel like I’ve barely scratched the surface. But through plenty of experimentation, questions, debates, articles, brainstorms, napkin sketches, and just flat out building stuff, I know now what the purpose and value of the product team at Persona is, and just enough about how we execute on that purpose to keep us learning and improving.

I also finally decided to make a trip to LA this fall to attend Lavalab’s Demo Night. When I was a senior in college, I had the privilege of helping get the organization off the ground with a close friend. To go back and see the students pitch the products they’d been working on for the semester was one of the most gratifying experiences I’ve ever had. I’m thankful that we planted a seed, and that each successive cohort of students has continued to pour their energy into building something even more impactful.

On teams

This topic deserved a section for 2019. Individual genius is well-recorded throughout history. It’s easier to tell a good story by focusing on individual achievements. There’s a reason why the CEO takes the lions share of the credit but also the brunt of the blame. There’s a reason why all the memorable fables and tales are based on individuals.

Personally, I know I’ll never be able to achieve the impact I’m looking for without working with an incredible team. I enjoy presenting my work and receiving recognition as much as anyone, but I thrive more behind-the-scenes. I enjoy 2x’ing the productivity of everyone around me. I take pride in being the glue across functions. It even manifests in videogames- I always pick support characters. That tells me that I’m best on a team. What’s the point of tracking monthly goals and areas for improvements for work? To become a better leader and teammate.

By nature of being an early employee and being in a product role, I have the privilege of working closely with everyone at the company. For all the challenges it presents, I relish the opportunity and will be nostalgic when that’s not true anymore. This year has been particularly illuminating in working closely with different kinds of individuals. My job is really to communicate effectively across different personalities, which also means I may get conflicting feedback that’s difficult to reconcile. What works for one person may not work for another. That’s been my biggest challenge this year in being a good teammate, and will continue to be a point of emphasis next year. With focused listening, empathy, and a willingness to incorporate tough feedback, I hope to keep improving.

On identity

In the 2018 post, I laid out my struggle with the idea that working is not synonymous with success. But producing something meaningful is a significant part of my identity, for better or worse, and that’s why I’ve always wanted to put my all into something that I actually believe in. Let me tell a story about why online identity is the right “something”.

My mom recently came up to me and asked if I had heard of truepeoplesearch.com or whitepages.com, sites that aggregate and show you personal information like address history, emails, relatives, and more in seconds. The conversation went like this:

Mom: “Have you seen this?! How are they able to get all this information?”

Me: “Mmm, I’ll tell you a truth. Privacy is dead.”

Mom: “What?! Who’s providing all this information?”

Me: “Every time you give you personal information to a site, they’re probably selling that data to someone else. Even worse, entities you trust like banks and credit bureaus do it too.”

Mom: “How are they allowed to do that?”

Me: “There’s minimal regulation in the US around the data industry. Especially in the US, the identity data industry is just companies selling data to each other. It’s really messed up. Europe is a bit better. But really, this is why Persona exists. If everybody’s data is already so readily accessible, there needs to be better ways to verify that you are who you say you are.”

Mom: “How can I get them to remove this information?”

Me: “Honestly, it’s too late. All our information has been exposed in one way or another. You remember all those data leaks? If a bad actor really wanted to impersonate you, it’d take them five seconds and a couple cents to get all the information you need. Fact is, we’re not important enough for them to care.”

Mom: “I can’t believe this.. this is really terrible..”

Tying self-actualization to a startup that has a large chance of failing is a risky proposition. But it’s the type of risk I’ve always wanted to take and 2019 has only provided further evidence that this drive is a net positive for me.

I take pride in my work, which means I get very attached to it. Therefore, it’s been difficult for me to let go of the work I’ve started as new folks join. Inherently, I know that they’ll do a much better job than I ever did, but I always have the urge to fully hand off all the work I’ve done in the hopes that the new owner won’t have to go through the same mistakes I did. Learning how to be comfortable with letting go of things and giving guidance as opposed to direction has been one of my greatest challenges this year. And this article was instrumental in helping me think through and start solving the problem.

'Give Away Your Legos' and Other Commandments for Scaling Startups

I’m all too cognizant that burnout and overworking are constant obstacles on the path of tying my work and personal identity together, so it’s fortunate that I can also focus on other areas like relationships and fitness.

On relationships

It always bears repeating that I’m immensely grateful to have such incredible people in my life.

This year, I was reminded of the role that luck plays in our relationships! It’d be one thing if I met my girlfriend on a bus ride. Instead, I merely saw her on the sidewalk as the bus whizzed by her waiting at the stop. We were old classmates, and I decided to reach out via Facebook messenger:

“super random, but was on the 38 bus this morning passing Fillmore and i swear i either saw you (or someone who looked a LOT like you) on the sidewalk”

That was all the spark we needed.

At a startup, I’m lucky to be grinding through the early stages with people I not only respect professionally but also consider close friends. As more folks join us, it won’t always be the case, so I’m thankful for the bonds we’ve forged this past year and cherish the small moments. Some of my favorite moments with them were simple. We’d be at the office late, round up everyone for dinner, and eat and laugh before going home.

With each passing year, I recognize the increasing important role that proximity plays in relationships. Many folks I know have started families and moved back to Dallas (my hometown) to be closer to the rest of their families. And for my own parents, I’m continuing to seed the idea to move out to California. It won’t be easy, but we made some progress this year when my sister and her husband bought their house in San Jose.

On fitness

I took a break from weightlifting, and picked up rock climbing (bouldering, specifically). I would’ve preferred not to offer myself up as another trite example of a SF techie, but I am what I am! There’s a number of reasons why I picked it up:

1. weightlifting is boring
2. friends pulled me into it
3. it’s an individual activity but very social
4. you’re solving a puzzle with your body
5. my body type affords me a lot of advantages
6. looks cool when you do it right
7. I’m already a monkey according to the Chinese zodiac

Wrap up

2019 goes down as The Year of Going in the Right Direction. Why? 2019 laid the foundation for better things to come. I feel challenged by and proud of what I’m doing day in and day out and I’m grateful that I can continue to build deep relationships, both old and new. I could never understand how the average American could watch up to four hours of TV a day. Now, I get home each day after a long day at work, and I’m so mentally drained that I can’t read, write, or do anything that requires a modicum of thought. So what do I do instead? Watch YouTube videos, check sports scores, and go to bed. I get it now.

I’ll end with ten more memorable moments from the year:

1. Midnight hustle on Slack to launch the Persona rebrand
2. Cooking a Chinese dinner for my girlfriend and roommate on a random Wednesday night
3. Day trip to Portland, Maine
4. Persona Friendsgiving
5. Mom’s 60th birthday
6. My high school roommate getting married to his high school sweetheart
7. Discovering slot machines and earthquake in Vegas
8. Each one of the three new offices we moved into
9. Going outdoor climbing for the first time
10. Camping amidst the beauty of Washington in the fall

Best wishes for a happy and healthy new year!