My 2018 Review

Image via Lucidchart

I’m a fan of self-tracking. Possibly obsessed. I log workouts and calories consumed. I track red, yellow, green against personal monthly goals. I maintain a CRM of family and friends. I recap books and save key takeaways in a sortable spreadsheet. Each week, I write down five things I’m grateful for. I jot down what I did that I’m proud of each day. Before bed, I review a checklist of ten habits I’m trying to build. I don’t check off everything every day, but this habit of tracking habits helped me start flossing regularly this year. Maybe a decade or two late but better late than never!

As I reviewed my assortment of spreadsheets at year end, I decided to bring it all together in the form of a written recap. It would be a worthy challenge to condense a year into a couple thousand words, offer a life update to friends and family, and hopefully stimulate others to reflect on the past and upcoming year. Personally, I hope to read this ten weeks and/or ten years from now and appreciate how 2018 affected me.

It’s human nature to underestimate the effect of randomness and luck, an inclination that causes complacency and incorrect correlations as well as being a popular topic in books I’ve read: Superforecasting, Thinking in Bets, Creativity Inc, Algorithms to Live By, and 99% of behavioral economics books. Knowing that, I’ve learned to do postmortems for both successes and failures, so I wanted to reflect on both the good and the bad in this review.

Table of Contents

Why self-track

Self-tracking serves four key purposes:

  1. Stay focused on my commitments. I’m constantly reminded why a certain goal is important to me and how to achieve it.
  2. Have data to observe trends and positively adjust my behavior over time.
  3. Stay motivated. Unsurprisingly, my future self is exceedingly lazy and underachieving.
  4. Great for monthly, and now, yearly reviews!

It might be laughable that I need a reminder to be grateful. But I’m not the kind of person to frequently give compliments or express love and adoration to friends and family. I’m working on it, and I see a spreadsheet as a concrete step to being more empathetic and compassionate. That’s the beauty of tracking everything- it’s a mechanism for step-by-step improvement. And 1% improvements compound quickly.

Compound interest is the eighth wonder of the world. He who understands it, earns it… He who doesn’t, pays it.

- Albert Einstein

I try to be mindful that working is not synonymous with success. It’s easy to be infatuated by mindless progress. One thought that really stuck with me this year was that being busy has become inextricably linked with success. I struggle with this. And self-tracking reinforces the importance of being busy, so I can always have something to track. At least once a day, I feel like I’m wasting time by not doing something “productive”. I tackled this conflict by reminding myself to relax once in a while (where relaxing is a euphemism for watching sports), avoid comparisons with others, and be happy for and celebrate others’ accomplishments.

On writing

I wanted to write more this year. This post explains why. TLDR: it’s challenging.

I’m enormously grateful for the feedback I received on my South America blog. If I was to distill all the comments into one overgeneralized statement, it would be, “I like your style”. That’s great! I’ll keep upgrading my vocabulary, so I don’t have to google synonyms for “big” and “small” all the time. I’ll be overly transparent. I’ll be snarky. I’ll use bad puns. I’ll be witty and fail. But most importantly, I’ll keep practicing. This year, I wasn’t consistent. Days of writing were followed by months of nothing. While I’m not ready to commit to daily minimum word goals, I’ll aim to write habitually whether it’s first thing in the morning or right before bed.

I also thought I made significant strides as a writer. I applied more active instead of passive voice. I added more vocabulary to my repertoire. I discovered unique elements of my voice, tone, and style. But then I was exposed to the world of marketing copy while tasked with writing copy for the company website. What do you mean I need to repeat myself constantly? Is that a real sentence? Wait, is that even a real word? I was humbled by the nuances. I’ll never be a professional copywriter, but I look forward to learning more about the art of sales copy in the next year. And for anyone who engages in persuasive writing (i.e. everyone), the below deck is one the most helpful learning resources I’ve encountered.

On failure

My most important holdover goal from last year was to put myself in a position to fail and to take big risks. I’m immensely grateful to have lived and continue living a privileged life. But I seek challenges. Or maybe I’ve been reading too many startup books in which failure is romanticized and outright celebrated? Iterate your way out of failures and into resounding success! Don’t let anyone out-fail and out-iterate you! Jokes aside, what does resonate with me is growth by discomfort.

Solo backpacking in South America was one risk. Not finding a job and instead building Floop as a self-taught web developer was another. I joined Persona as the first employee and moved to San Francisco in less than two weeks, fully understanding that there’s an absurdly high chance, say 99%, that we never reach our long-term vision. Heck, I didn’t have healthcare for three months! Talk about living life on the EDGE…

But I could’ve done more. I should have gone to those developer meetups even though I felt hardcore imposter syndrome. I should have sent cold emails to the people I admire and want to meet. I should have said hi to the cute girl on the plane. I’ll strive to fail more.

On reading

Books are the ultimate hack. Thousands of hours of experience and reflection by domain experts are compressed into a format that I consume in a fraction of the time. I had a goal to read 31 books this year. I read 28 due to a steep slowdown after moving to San Francisco, but I’m not particularly worried. The number served as a reminder to set aside time to read. Hyperawareness of a numerical goal in this case incentivizes picking shorter books. That proved to be true inadvertently, as more of my reading shifted to long-form articles (driven by Medium), which I foresee as a continuing trend.

Here’s a shortlist of book recommendations with links to my reviews:

See all the books I read here.

On building

One of the best decisions I ever made was attending a hack-a-thon for education in 2015. There, I met a group of amazing people, and as a team, we embarked on a multi-year journey to build a tool called Floop to help teachers give students more effective, efficient feedback. After three years, we’ve had several hundred users. Our total revenue is in the double digits. We haven’t exactly blown up. Did we build a great product? No. Part of that is because I’m not a great web developer. Completing a mobile web development course helped, though not as much as I expected. But did we solve a problem? Absolutely. I’m proud of what we accomplished with a side project while juggling full-time jobs and starting with no experience to build working software from scratch. We hit on a real pain point, but we didn’t have the right combination of skill and expertise to execute. Timing also wasn’t right, and it was a tough decision to move on from the project this year.

In October, I moved to San Francisco to join a high school friend’s startup. We’re working toward a super ambitious vision to be the trusted identity provider on the internet. Today, our personally identifiable information is fragmented across the internet and constantly leaked by insecure services that are more interested in monetizing our data than protecting it. Businesses are challenged to confirm that customers are who they say they are, frequently forced to add unwanted friction to the customer experience. We’re building Persona to be the solution. This is the kind of business that keeps up you night. I even had a dream about work- whether it’s a good thing is debatable. As the first employee, I’ve been wearing different hats and learning a tremendous amount in three months while building out our sales funnel, managing data providers and vendors, becoming an industry expert, and much more. While some day-to-day work is inevitably a grind, there’s never a lack of things to learn and do. It felt right to share the most interesting bits, so I’m blogging our monthly learnings to:

  • share learnings about building a business
  • share perspective as an early employee
  • have concrete learnings if we fail
  • know how we got there if we succeed
  • help future employees understand how we evolved over time

I recently told a friend what I was currently doing and he asked me if it was like Silicon Valley, the TV show. To which I nervously laughed and replied yes. We’re such a typical software startup, it hurts. Although I hope we’re not as awkward. I’m not sure whether that helped or hurt the blog from a promotional standpoint, but my hope is that readers take away something to apply to their lives and get a good laugh. Look out for the first post in January.

On being a better listener

I like talking. I do it a lot. Writing, when I think about, is exclusively talking. But I want to listen more. As I’ve gotten older, I’ve found more wisdom in the old mantra that most conflicts are due to miscommunication. And in my personal experience, most miscommunication is caused by people talking over each other. Therefore, talking over each other leads to conflict. I emphasize that this observation is based on my personal experience because most of the people I’ve interacted with on a daily basis follow the dominant Western principle of “make your voice heard”.

This year, I’ve built up a toolbox of strategies:

  • Ask questions. Give opportunities for others to open up.
  • Get comfortable with awkward silences (a great negotiation tactic too).
  • Repeat what you heard back to yourself.
  • Repeat what you heard in the form of a question (e.g. I think I heard you say that…).
  • Hold eye contact. If it gets too awkward, look at the bridge of the nose instead.
  • Be more empathetic. Ask people about their family. Show people that you remember what they said.
  • Not every statement requires a response. For example, I’m still learning how to gracefully accept compliments. The Great CEO Within frames this well. Praising others requires courage- don’t deflect and devalue the act by talking around it. Just listen, accept, and say “thank you”!

There’s so much to learn from smarter, more experienced folks. But it’s hard to do that if I talk more than listen. So the simplest key indicator of whether I’m a better listener is whether I’ve learned more this year than last. And for 2018 that was definitely true.

Learning a language happens to be a great way to sharpen your listening skills. This year and last, I’ve re-discovered my passion for learning languages, specifically Spanish and Mandarin. In fact, one of the reasons I went backpacking was for language immersion. Speaking is the hardest part of language learning, so I’m naturally inclined to talk less and listen more. Simply hearing is not enough. There’s a three-step process that requires my full attention. Listen carefully, translate, and interpret. While backpacking, the difference between hearing and listening was being stranded in the middle of nowhere or getting to my intended destination.

I’m happy to have started integrating language learning into my daily routine, but I recognize that immersion is such a major, and currently missing, part of the equation. Self-learning isn’t cutting it, and I’m not surrounded by native Spanish or Mandarin speakers. Being forced to survive with your second language is a strong incentive to improve rapidly. I won’t be able to live abroad in 2019, but my goal is to find a language learning community to bridge that gap.

On relationships

I both failed spectacularly and made clear progress. This year, the momentum really shifted towards nurturing relationships that I’ve already made. I have amazing friends and family, and I decided to prioritize them. That’s why I created a personal CRM. There are so many people that I want to spend time with, keep in touch with, celebrate accomplishments with, and support in any way I can. For the first three months of year, I was still solo backpacking in South America. I met incredible friends there, but the true test will be how those relationships grow over time.

On the other hand, it was another quiet year for romance, or for that matter, dating. That in itself isn’t an issue. I don’t mind being single. But over time, I’ve started to justify my lack of confidence as the result of being too busy striving for success to dawdle in relationships. Or that I’d rather read than meet people. That’s true sometimes, but not all the time. And I definitely need to stop using these excuses as a perverse indicator of success.

On fitness

While backpacking wasn’t great for my waistline or strength, it was amazing for my cardio. I haven’t felt that good about running and hiking since before my trifecta of ACL surgeries. Marathon anyone? I also started tracking my daily stretching, though I wasn’t as consistent compared to 2017. Hardwood floors are no excuse! I didn’t do as much pilates as I would’ve liked either, which besides being great for flexibility and core strength, is also a great remedy for my historically poor posture and slouching in a front of a screen all day.

After returning home from backpacking, I refocused on strength training and eating healthy. Many thanks to my mom for bearing with my painfully bland diet and those soul-sucking, snack-less afternoons. I’m proud that I hit 12% body fat percentage at some point in my life. Didn’t last long, though. It’d be easy to blame external factors (e.g. moving to a new city), but it was squarely my fault for not setting aside time to exercise. I also erred in not shelling out for a gym. A monthly sunk cost and working out next to randoms are underrated motivators.

The final numbers are bleak. I had six strength goals based on my bodyweight, and only hit the first two. One interpretation is that I’m strong proportionally. Another is that I have the upper body of a scrawny Asian. Both true.

  • 100 pull-ups in 20 minutes
  • 1.75x squat*
  • 1x military press*
  • 1x barbell row*
  • 1.25x bench press*
  • 2x deadlift*

*5 sets x 5 reps — a standard lifting baseline

Wrap up

2018 goes down as The Year of the Couch. Why? Simple, it felt like I spent more nights sleeping on a couch than on a bed. I did the math, and it turns out I was only SLIGHTLY exaggerating. By my best guess, I spent somewhere between 100–150 nights on a couch. It’s a symbol of the generosity that was shown to me and the incredible people I got to spend time with!

I’ll end this inaugural annual review by sharing some of the items that showed up the most on my gratefulness tracker:

  1. Family & friends- I’m always grateful to make new friends. But I’m especially grateful this year for old friends and my family. The ones that know me, shared memorable experiences with me, support me, and constantly challenge me.
  2. Travel & trips- Backpacking was (likely) a one-time experience. But what I can always look forward to are the yearly trips and weekend excursions with friends and family.
  3. Flexibility- Both in terms of how I manage my time and exercising my freedom of choice. I feel empowered to do things that I want to do.
  4. Habits- I’m mixed on the willpower-depletion theory. But building good habits makes life infinitely easier.
  5. Free housing- In the form of a couch, of course.
  6. Not having to set an alarm
  7. Good and improving health

Goals for 2019? Finish the annual review at least 1 hour before midnight on New Years Eve. Best wishes for a happy and healthy new year!




Endlessly curious, always optimizing. Startup and product enthusiast.

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Vincent Tsao

Vincent Tsao

Endlessly curious, always optimizing. Startup and product enthusiast.

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