Over the years, I’ve found it immensely helpful and inspiring to hear about and learn from the career journeys of others. As I cross the first decade of a 40-year career journey, I thought I’d share the story of mine, the choices I’ve made, and some of the lessons I’ve learned along the way.
1. Be bold, deliberate, and forward-looking with your career choices.
I majored in Biochemistry and Economics in college and had laid the foundations for pursuing Chemistry in graduate school. Look, I was a co-author of a chapter in a book on tissue imaging 😂!
I share this with you as a representation of how wildly different the seeds of a career I was actually planting a decade ago than the one I’m pursuing today in engineering, but also to myself as a memory of an important milestone in my career journey—this was the last project I ever took on in the field of Chemistry.
After college, I began to notice that I wasn’t energized by my work; I was doing it simply because it was the path of least resistance. There were several reasons why I wasn’t happy, but I mustered the energy to focus instead on what might make me happy, or what was important to me in a choice of career. This is the same approach I took over the years when making similar decisions—to understand what I am running toward, rather than what I am running away from. I made a list that I still remember well today:
I was good at math and science. I wanted a job that leveraged my analytical abilities.
I wanted a career that gave me the opportunity to create value through building. I wanted the output of my work to, even if just in a small way, make the lives of future generations better, and last beyond my lifetime.
I wanted more control over the progress I would make with my career path. I preferred career tracks with fewer formal requirements. For example, I considered the actuarial profession for a hot second until I realized the arduous credentialing system that is part of the job.
I am a fairly impatient individual. I wanted to be able to see the results of my work quickly. Chemistry experiments often take too long, sorry!
I didn’t care to be crazy rich, but I hoped to find a career that will allow me to build a comfortable financial cushion.
As you can guess, I figured a career in software engineering and startups might fulfill these items. The real question was: how do I find my way into the industry? I needed to equip myself with the right skills to land a job. An obvious next step was to teach myself what someone might learn in a 4-year undergraduate curriculum in computer science.
2. You can learn something new if you put your heart to it.
What’s your biggest takeaway from college? I’ve posed this question to many people over the years, and if there is a consistent theme, it’s that for most, it wasn’t the actual material learned in their classes. For some of you, my answer might resonate—the most important thing I got out of it was learning how to learn:
Recognizing that it’s not just about knowing that but also the knowing how.
It’s tempting to find shortcuts, and talent can give you a leg up, but there is no substitute for mastery through hard work.
But most importantly, realizing that the barrier to accumulating knowledge often lies within oneself, that is, we rely more than we should on the structure of formal education to fill the motivational gap in us.
It is with this spirit that I embarked on an arduous, yet exciting journey. Below are some examples of how I invested my time. You may be disappointed yet encouraged to see that these were everyday efforts that anyone can pursue:
Daily coffee chats with a co-worker and friend where he would pose a new programming puzzle or teach me a new CS concept every day. I would spend evenings reading up more online. We did this for almost 9 months.
Completed several online CS classes. These were the early days of MOOCs, and I signed up for every class available!
Built a personal website. I learn best through doing.
Participated in Hackathons. More learning by doing!
You may wonder what I think of bootcamps, and whether I considered enrolling in one. I did not; bootcamps weren’t readily available then, and I had other ongoing work obligations. That said, I believe bootcamps can be helpful to others looking to transition into writing software like I did, and I have seen successful careers built off those foundations. I’ve observed that the more successful bootcamp graduates tend to recognize that bootcamps aren’t a magic wand. They learn the how on top of the that, they know that there is no substitute for mastery through hard work, and their motivation for pursuing software comes from within. For them, the learning doesn’t stop after the bootcamp; instead, it is just the beginning. I know this well—after more than a decade in the industry, I am still learning, every single day!
3. Gravitate towards people who believe in you.
These first few years after college were particularly challenging as I navigated a wild career pivot, and I would not have found my way without the support of many people along the way:
I am lucky to have a family who was supportive of me pursuing my passion, and if my parents were ever nervous that I wouldn’t land on my feet, they never showed it.
My first boss out of college, Professor Kishore Bhakoo, so kindly gave me the opportunity to co-author the book chapter I shared above, despite my inexperience in the field. More importantly, he wholeheartedly supported my transition out of his bio-imaging lab even as he lost a team member.
Jamie welcomed me to her human-computer interface research lab and landed me my first professional opportunity in software, despite my limited CS background.
Yanchuan, the co-worker and good friend I talked about above with whom I had coffee chats with every day, patiently imparted at least 150 hours worth of CS fundamentals to me.
Yink, a good friend of over 20 years and a colleague in 4 companies over the course of our careers, inspired me to work in hi-tech startups, and was my first real software engineering mentor.
Dinesh, the founder of the first startup I worked at, hired me despite knowing it would be my first professional startup software engineering gig.
Wade made me his first trans-Pacific hire for the TellApart engineering team, helped by the strong advocacy of John and Wei.
…and very many others as well, in big and small ways alike.
Would I be doing what I am doing today without some of these folks taking a leap of faith on my ability to deliver? Certainly not. Did they know for sure I would deliver on their bets? Absolutely not. As I find myself in positions where I can create opportunities for others, I try to do the same. Sometimes, all someone needs is someone else taking a leap of faith on them.
Unsurprisingly, I had my fair share of detractors along this journey:
I was told that pursuing a career in software engineering without a computer science degree was an act of sheer folly.
I was turned down by multiple hiring managers.
I was asked why I even wanted to pursue software engineering—this was not a career that many aspired to in Singapore, where I was based then.
Gravitate to those who believe in you, especially those who are willing to take a leap of faith on you.
4. See a problem? Solve it.
In early 2014, I followed my heart to Silicon Valley, the center of gravity of hi-tech startups, when I joined a fast growing post-Series B startup that was TellApart. I don’t think I was aware or particularly deliberate about it then, but what led to a fruitful several years at TellApart and post-acquisition Twitter journey was my willingness to help solve problems.
Less than a month in, our self-hosted code review tool Gerrit broke, and a good number of engineers on the team, myself included, naturally screamed in annoyance. At first, a restart of the tool appeared to fix it, but then it began to crash more frequently. No one officially owned Gerrit, so no one devoted time to look into the cause of the crashes. One day, I had enough, and decided to figure it out. Its cost on our 50-person engineering team’s productivity justified the time I was going to spend on it. I recall pouring over Gerrit’s source code, performing manual Gerrit database operations, and upgrading the version of Gerrit we used—each of these contributing to increased stability of the tool. I was new to the team, but others saw my willingness and ability to step up and problem solve, and it earned me a healthy bit of respect that I continued to build upon to gain more responsibility over the years.
I became the unofficial Gerrit (and through similar circumstances, Jenkins!) owner over the course of my tenure at TellApart and Twitter. I think it was only as I left the team as a tech lead of a team of awesome engineers that owned one of the highest traffic services at Twitter—log ingestion @ 3M RPS peak traffic—that I recognized much of the growth I accumulated over the years could be attributed to the relentless solving of problems I identified along the way. What’s even cooler was that I got to learn something new with every problem I solved!
5. Surround yourself with people who push you to be the best version of yourself.
TellApart and Twitter was an incredible journey, but there came a time for a new adventure: a bigger challenge. It gets harder to top every exhilarating ride you take, but I would not settle for less. I spent 9 months passively then actively looking for new opportunities; I researched more than 50 startups, interviewed with several, and eventually agreed to join Front.
These were some of the major factors I considered in making this decision:
Product
There should be product-market fit; if there wasn’t, I’d prefer to take on that risk as a founder.
The TAM is huge; there are opportunities for a highly valuable product of today to grow into a frighteningly ambitious product of tomorrow.
It wasn’t in the advertising or e-commerce industries. I was happy to put those behind.
Role
I wanted the opportunity to grow as an engineering and business leader.
People
I wanted to work with folks I would get along with socially. After all, I’d be spending at least 40 hours a week with them.
I wanted to work with folks that can push me to be the best version of myself.
All of these were important, but the factor that tipped the scales in favor of Front was the people and how they would push me. The extremely talented individuals I was lucky to be surrounded by over the early years of my career brought the best out of me and pushed me to grow more than I would have in other environments. And when I saw Front and its team of hyper-intelligent, ambitious, hungry individuals that were also humble, caring, and knew how to have fun, I knew it was my next professional home. By the way, many of these qualities are baked into Front’s company values today!
6. Be a talent magnet.
While many ambitious individuals seek environments that push them to be better, I’ve noticed that fewer actively think about the responsibility they subsequently inherit to make their new professional homes equally or more attractive to future teammates. If you aren’t able to contribute to attracting top talent to your team, you are reducing the capacity of the company to attract top talent over time. The best thing you can do for your career is to help create a talent flywheel, wherever you go.
The obvious opportunity you will have in creating the talent flywheel in any company is through its hiring process. Think about the personal traits of yours that tend to attract others to work with you, and participate in the parts of hiring that allow you to showcase those most. Proactively work on areas that you fare worse in.
Over the years, I’ve observed that many individuals who want to move into management or are already in management in fast-growing companies do not invest enough in this skillset, which not only hinders their ability to succeed as a manager, but hurts the company, since team building and hiring are priorities in such environments. A suggested thought experiment: think about whether you are able to attract former co-workers to your current company. After all, if those who have seen you in action aren’t drawn to work with you again, why might someone you don’t have a prior relationship with do so?
I don’t think I am where I want to be as a talent magnet yet, but I am encouraged by the teams I have been able to build over the years.
7. Invest time in growth within companies.
I have been at Front for over 4 years now, which makes it the longest length of time I’ve worked at a company. I often get asked—what keeps me at Front? There are a few reasons:
The growth is ahead of Front, not behind. Front is past trying to be a unicorn, and has the foundations to compare herself to multi-10B companies. Even the 200B SaaS pioneer and behemoth doesn’t seem completely out of reach.
I am still surrounded by people who make me better.
I continue to find S-curve learning opportunities, supported by the continued growth and success of the company. To date, I have shipped highly challenging infrastructure projects, built and led various user-facing and foundational teams, and developed expertise in domains I never thought I would get into, like security. I have an exciting opportunity to shape the future of a product engineering organization.
The factor that many of us will have the most control over is identifying and riding S-curve learning opportunities, so I thought I’d share a few more of my thoughts on this:
I’ve found that the first S-curve at any company typically stretches 1-2 years, so I would want to either parachute out of a company within 3 months because I accidentally found myself in some serious dysfunction (thankfully not yet!!), or invest at least 2 years.
When an S-curve runs its course, I have proactively identified new S-curve learning opportunities, leveraging the relationships and respect I’ve earned to take on opportunities that may not exist by going for a reset. I have found that proactively having these discussions with my managers have led to productive outcomes.
There will likely come a time when the best way to grow is via changing companies, though I’ve found by observing those around me that it is often a mistake to make the hop before exhausting all S-curve opportunities available to one in their current company. Often, jumping into a new environment feels like growth because there is learning, but these learnings don’t always get you to the next level because they weren’t the gaps that were holding you back.
As an aside, two ideals I’ve strived toward when leaving companies are:
To leave a team in a better place than I found it.
To minimize my contributions as a factor in the team’s future success, through grooming others to replace my role in the team.
Finally, to drive home my point about investing time in companies:
The best people I’ve worked with in my career have solid stints at several companies.
Many hiring managers I respect for building great teams will immediately pass on candidates with a significant number of short stints.
8. Think long term.
I took a compensation hit when I joined Front: I left behind the liquid compensation of a public company including a good chunk of unvested TellApart acquisition dollars on the table. I certainly can’t claim or suggest that this choice is the right decision for others—we each have our own financial situations to consider. Moreover, there are a significant number of non-financial factors going into a decision like this. The point I am hoping to make, however, is that I was able to confidently make this decision for myself because I was thinking long term:
I was confident I would quickly demonstrate my value to the company such that there will be natural compensation adjustments down the road. Front will want me to stick around!
I believe in betting on equity growth potential. In a Silicon Valley context, the real financially life-changing opportunities don’t come through salary; they come through equity growth.
I wasn’t just planning for the next job, I was thinking about my 40-year career, and how Front would fit into that. I saw a company that was going to grow and will put me in a driver’s seat for its growth, and in return, reward me with the opportunity to take on bigger responsibilities with time.
So far, I am grateful that long-term thinking is paying off for my career.
How will your 40-year career look?
…and that is the story of the first decade of my career! I wrote this both as a way to share my journey with you, as well as to remind myself of some of the lessons I’ve learned along the way. Whether you connect with some or none of my professional journey, I appreciate the time you took to learn about mine, and I hope reading it did in one small way or another help you think about yours.
I mostly hope it inspires you to recognize that, whatever your purpose or motivations and wherever you are in your career, that while your managers, mentors, HR professionals, career frameworks, ladders and advice can be along for the ride, that only you can truly captain your career, and to start doing it today if you haven’t already! Dream big, and never stop believing in yourself.
Of course, what is a blog post on Front Page without a plug? 😃 If you’re interested in making Front a part of your career journey, check out our jobs page.
Written by Sean Xie
Originally Published: 23 July 2021