At the end of every year, I spend a disproportionate amount of time reflecting. This is only possible given the copious amounts of free time I have after the big tech companies shut down during the last 2 weeks of the year. This year blew by and on the surface, not a lot has changed - I am still working at Shopify in the same role, living in the same place in Toronto. I had grand ambitions to live outside of Toronto for an extended period of time (didn’t happen), write / publish more (published once) become a better chef (kinda happened), amongst many other goals. I might not have accomplished all that I set out to do, however, there were so many amazing highlights that made 2021 memorable:
Explored Vancouver Island in a camper van
Saw my sister get married
Caught up with friends in Kelowna over many glasses of wine
Drove through Joshua Tree National Park in a muscle car
Learned how to surf and snowboard
Bought a car and learned how to drive manual
Met my coworkers in real life after 1 year of working together
Got promoted for the first time ever
Became a Skillful mentor and created the Product Ops Sprint
Although 2021 wasn’t what I thought it would be, I found that I learned and grew in ways that I didn’t expect. Here is a compilation of my top ten lessons that I hope to take into 2022 and beyond:
Life
Over-indexing in a single category quickly leads to diminishing returns. When I evaluated the past year, I broke it down into components such as career, physical / mental health, relationships, hobbies, adventure and more. I found that I spent a disproportionate amount of time this year in the career bucket. While I did get rewarded for my efforts, it came at a cost of my physical health and relationships as I got to spend less time with people who matter.
Do more non-work things. During the winter break, I deliberately set aside work despite a part of me wanting to get ahead for 2022. I was able to spend time on more physical activities such as bouldering and learning how to snowboarding. I also rediscovered my love for reading fiction this year (highly recommended Recursion and Red Rising Saga if you’re into sci-fi) and pivoted to almost 50% fiction v.s. 2020 when only 10% was fiction. While none of what I did this break has any direct benefits to my career, I feel recharged and ready to go for 2022.
Focus less energy on doing what I think I should do v.s. what I want to do. When I do what I think I should do, it results in less engagement as the driving force for action comes from a place of obligation. By focusing on what I want to do instead, I gain more energy and greater overall happiness.
Work
There’s never a good time to take vacation. I always have mild anxiety when I take vacation. I found that I have to be okay with having some minor things slip and trusting in your team to help support. Any healthy organization will have some redundancies built in and it is a humbling reminder that no individual is ever that critical to an organization’s success. I was able to spend ~4 weeks this summer in BC with minor days of work mixed in and it was the best decision I made. I also found success with workation when I tagged on a couple extra days onto my LA / NYC work trips to sneak in some extra adventure.
Crafting your own role is tough, but highly rewarding. In my role at Shopify, I play a mix of a Product Operations and Product Management role. This is the perfect fit for me given I have high level visibility while still having being able to execute on specific projects. It didn’t start that way and took a lot of tough conversations, luck, and people to take a bet on me (thanks Mike!). Given the role is crafted based on my team’s needs and my interest, it requires constant re-evaluation, but when it works, it is so much more rewarding than a generic job description.
The people side of building products is just as hard as building. When I first started working in Product Ops, I thought the technical aspects of building was the hardest part. After 1.5 years, I can see the people side of things is just as hard. Having seen a re-org behind the scenes, I saw how tough it was for newly formed teams to understand the organization’s shifting mission and their individual roles in it. Managing interpersonal issues is highly important to having high performing teams and neglecting it results in high turnover and poor products.
Make educated bets, early and often. Experimentation was a big unblocker for my team’s work. By driving of an experimentation culture, teams felt more enabled to make more bets, some of which paid off in improved metrics and others in improved understanding. This increased the overall velocity of shipping and confidence that the work we did actually moved the needle.
Creating
Publishing at 80% complete is better than a 99% complete draft. I have many semi-complete blog post that are stuck in draft mode. There are few times in life where you actually need to have something be 100% perfect and blogging definitely isn’t one of them. The main blocker is mainly my own ego and fear of being judged for a subpar piece of work.
Writing is a huge amplifier and worth the time investment. My post about Product Ops 101 took me ~3 hours, but has helped me scale myself by not having to repeat the same spiel about the role to prospective candidates. This enabled coffee chats to dive into deeper conversation about the role / fit in less time or eliminated the need for a synchronous meeting.
Creating is hard and not everyone will love what you make. I had the chance to launch various product experiments and features this year and found just how tough it is to build from limited data to unforeseen bugs. I even received my first mean tweet for a launch I helped lead, which I wear as a badge of honor that someone cared enough to tweet about it.
Let me know if any of these lessons resonated with you! I have no idea what 2022 will bring - my only hope is that I am wiser and more curious and learn the lessons to come.