Things I Wish I’d Learned Earlier in My Career
I knew that I wanted to be a Software Engineer since I was twelve years old. I did everything I could to realize that goal. But did I limit my career by being too focused too early?
My daughters are now at an age where they mostly sleep through the night. Unfortunately, they are also at an age where even slight changes to their routines can have catastrophic effects. The switch to Daylight Savings Time happens to be one of these disruptive events.
On nights like these, I find myself sitting in a rocking chair with one or more curly-haired toddlers resting peacefully on my chest. With no electronic devices to distract me except for Google Home playing a curated selection of instrumental Disney lullabies, my mind tends to wander in whatever direction it desires.
Lately, my thoughts have been revolving around my career path and the series of events that lead to my current role as VP of Engineering for a high-growth technology startup. Never in my wildest dreams could I have imagined that the twelve-year-old who spent way too much time copying and tweaking lines of BASIC code from issues of Compute! magazine would grow up to lead high-performing software engineering teams.
Back then, computers were probably the only things that made sense in my life. They were simple devices that operated on Boolean logic. If you understood how to provide them with the proper instructions, they would return the expected results. Simple.
This early interest in computers had some interesting downstream effects. In high school, I was a mediocre student in every area except Computer Science. In college, Computer Science was the only degree that mattered to me. I could never comprehend why people frequently switched majors. Now I make a living from a career that oscillates between building software and teaching others how to build software.
When I tell people my story, they’re usually impressed by the clarity and consistency I exhibited in choosing my career from childhood till now. On the surface, it seems impressive and admirable, but what most people fail to realize is that I didn’t choose my career path. In reality, my career path chose me.
One of my greatest strengths is being able to focus on tasks for extremely long periods. This ability enables me to tackle problems with single-minded focus and tenacity until I arrive at a solution. Unfortunately, this trait can quickly have detrimental effects if not carefully balanced.
The Single-Mindedness Dilemma
…success is short-lived as imposter syndrome silently slinks in, feeding the need to re-establish self-worth…
It is a great irony that the one trait that has enabled most of my career success has also been responsible for limiting it to a certain degree. What could I possibly mean? It starts with the small things like skipping lunch to work on an interesting technical challenge. The challenge becomes an obsession and gets brought up in regular conversations with people who have no clue about the problem space, let alone the solution.
The late-night work sessions come next, followed by the failed solution attempts, which quickly lead to burnout and apathy. At the 11th hour, the “never give up” attitude shows up, allowing for a final push toward a solution. Success! The sense of euphoria kicks in. Management is happy. The kudos flow freely along with bonuses, pay raises, increased stock options, and promotions.
The success is short-lived as imposter syndrome silently slinks in, feeding the need to re-establish self-worth and prove value on an even more grandiose scale. Rinse and repeat.
5 Things I Wish I’d Learned Earlier in My Career
The above scenario is the classic definition of workaholism and the perfect representation of my life until a few years ago. Early in my career, I used this modus operandi to propel myself rapidly up the corporate ladder. Within what felt like a few short years, I transitioned from eager Graduate student to tenured University Professor to Lead Software Engineer and now VP of Engineering.
I’ve experienced enough successes and failures to know the difference. I’m confident in my ability to build and lead scrappy, high-performing engineering teams. I pride myself on being able to strike a good balance between people management and technical contribution.
But despite all my success, there are still many areas where I know I missed the mark. I hope that one day I’ll be able to at least advise my daughters on how to avoid these same mistakes.
If I could turn back the hands of time, here are the five things I would have focused on doing with more intention.
Be Serious About Establishing Work-Life Balance
Being a hard worker is an admirable quality; however, being work-obsessed is not.
Early in my career, it was easy to see individual effort translate to success at work. The missed vacations, avoidance of socializing with friends, and broken relationships seemed like necessary sacrifices on the path to career fulfillment. In actuality, they weren’t. Being a hard worker is an admirable quality; however, being work-obsessed is not. In the long run, this only leads to burnout, fatigue, resentment, and even health issues.
Keep in mind that the business will continue to run without you. Use those vacation hours, take time for recreation, prioritize family and friendship, and enjoy life. Set clear boundaries and expectations to avoid work bleeding over into your personal life.
I sometimes feel like a hypocrite because I encourage my team to strive toward having a healthy work-life balance, yet I often fail to lead by example in this respect. Being married and having children have certainly helped to shift my perspective, but I still have a long way to go in my journey toward achieving this balance.
Choose My Career Path Instead of Running on Autopilot
I wish I had created a career plan. It didn’t have to be a great plan and would have certainly changed over time.
I mentioned earlier that I didn’t choose my career path, but my career path chose me. What I meant by that is simply that I never really had a plan or roadmap. I essentially developed a passion for a skill that turned out to be highly marketable. I never really had any 1, 5, 10, or 15-year goals per se. I was happy to write code and make enough money to pay bills and save a little bit. Thankfully, I had several excellent managers who saw my potential and took chances on promoting me, even when I wasn’t quite ready. As a result, I was able to delay thinking about my career progression and continue on autopilot.
Coming into my role as a VP of Engineering, I realize that the job is much less about my technical skills and more about my ability to lead and motivate talented engineers to do great work. A big part of this job entails helping team members to set and achieve professional goals. Suddenly, I had to contend with is the notion of being less hands-on and more strategic. In short, no more career autopilot for me.
Maybe if I had invested more time and resources into planning my career, I would have had an easier time transitioning from individual contributor to engineering leader. I would have had a clearer picture of the job duties much earlier on and would have known what I needed to let go to be successful in the job.
Looking back, I wish I had created a career plan. It didn’t have to be a great plan and would have certainly changed over time. At the minimum, it would have helped me to have an idea of the kinds of non-technical skills, like networking and public speaking, that I needed to develop to be a more versatile and well-rounded employee.
Allow Myself to Pursue Other Interests
I wish that I had just taken those few extra steps to refine my natural talents.
For most of my academic career, I focused on classes that directly related to my major. I grudgingly took the bare minimum number of liberal studies courses that I needed to graduate. It turns out that I had other skills that I never fully developed because I was too focused on that Computer Science degree. For example, I love to write. So much so that I excelled in the creative writing class that I needed for liberal studies. I also have an ear for foreign languages and became conversant in Spanish after four semesters.
Today, writing is a critical part of my job, and the ability to speak Spanish has helped me conduct business in Latin America and parts of the Spanish-speaking Caribbean. If I had not been so focused on earning my Computer Science degree, I would have given myself the space to take the two additional courses necessary for a minor in Creative Writing or the five extra courses required for a Bachelor’s in Foreign Languages.
Although I still reap the benefit of those classes even now, I wish that I had just taken those few extra steps to refine my natural talents. It would have been nice to do more than speak Spanish “well enough” to communicate with native speakers or write “well enough” to get my perspective across to readers.
Master the Art of Networking
My attitude then was: “if my technical skills can’t speak for me, then it’s just not going to work out.”
I’ve never been comfortable at networking or making small talk. Networking, like most things, comes naturally to some people. Others, like myself, have to work hard at it. Networking can do so many things from a professional development standpoint. From building relationships with mentors and mentees to providing leads into future job opportunities, networking is a critical skill for the modern workforce, particularly when one ascends to higher leadership roles.
In college, there were many opportunities to learn how to network; however, I sidestepped all those opportunities because I was too busy focusing on earning the degree. My attitude then was: “if my technical skills can’t speak for me, then it’s just not going to work out.” How little I knew back then. If I knew then what I know today, I would have dedicated some time to develop those skills.
I’m fortunate enough to have the resources to afford a professional coach to help me with these deficits; however, I’d have been way ahead of the game if I had taken advantage of the networking opportunities that I had so many years ago.
Invest in Mentorship and Career Development
Once I began moving up the leadership chain, I realized that I needed professional coaching and mentorship to be effective in my day-to-day duties.
I never really put much stock in professional development until I transitioned from individual contributor to engineering leader. Before this, I never actively sought opportunities for career development or leadership training. Instead, I relied on the few canned courses or one-day seminars that some of my prior employers provided. I was never comfortable asking people to be my mentor, so I never really bothered. A few good managers provided mentorship to me indirectly, but never anything formal.
Once I began moving up the leadership chain, I realized that I needed professional coaching and mentorship to be effective in my day-to-day duties. As an individual contributor, it is much easier to gauge your performance based on tangible factors like the number of features implemented or bugs squashed. It’s not as clear-cut at the technical management level, especially the further removed you become from coding activities. At this stage, your success becomes based on how effectively your team operates. You become concerned with answering questions like:
- How much value is the team contributing to the overall business?
- Did your team meet established KPIs or OKRs?
- Has the team successfully achieved critical milestones needed for sales enablement?
- Does the team need more capacity or additional training to meet goals?
In my opinion, one of the core abilities that leaders must possess is the ability to take a critical look at themselves and understand their gaps in knowledge, skills, or experience and being able to seek out the right level of coaching or mentoring needed to address these deficits.
On the other side, mentoring others is one of the most satisfying parts of my career. Seeing individuals learning from my successes and failures is rewarding in itself, but being able to observe them pass on their learnings from me along with their own experiences is priceless.
I do not know what career paths my daughters will choose when they grow up. But whatever choices they make, I hope that they will have the right kind of mentorship to avoid the career missteps I’ve made. Above all else, I hope that they find the things that they are most passionate about and experience as much as possible without pigeonholing themselves into specific careers too early.
But for now, they are carefree toddlers. I will continue to enjoy these simple moments for as long as I can. I’ll take pride in seeing them grow, learn, and discover the world around them. They will be the authors of their own stories.
