Lessons from a decade of work

Career advice to my younger self

These are from an amalgamation of experiences working across both Silicon Valley and Toronto, in companies ranging from early stage startups, to a medium-sized company, to a big corporation. This can apply to many professions beyond just software engineering. I might write an engineering specific one after :)

Reverse Interview

A reverse interview is dedicated time for you as a candidate to ask questions. This is a good step after an offer is made, and the ideal person to talk to would be the hiring manager or a potential team member because they’re the closest proxy to your role. For the first few years of my career, I didn’t even think this was an option :)

Setting this call up has two other benefits right off the bat — it shows you’re interested and value your career choices and second, it buys you time to make a better decision. Time is a valuable resource in the negotiating process, especially with the rising trend of “imploding offers” in tech companies ie. offers that expire in 48 hours. Most of these timelines are negotiable, and framing it around setting up a reverse interview is helpful to ask for time extension.

Try out your job for a week

Interviews are a glimpse into what working there can be like, but it’s hardly an indication of the actual road map, the team dynamics, and so much more. A one week paid-trial, treated much like a contractor, gives both parties a chance to see if they’re a good fit. I tried this at two startups one week after the other, while trying to pick between them, and it was invaluable to my decision making. Needless to say, this idea might float better at startups instead of bigger companies that have more structured hiring processes.

Trust your instincts

It’s quite bizarre that each time I’ve started a new team/job/big project, I’ve known within a week (if not few days) whether this was a good fit. It took me a few years to even trust this instinct. After all, it did not feel rational making drastic decisions solely based on instinct and such little data.

Having the realization that it wasn’t a good fit didn’t make it any easier to act on it. In hindsight, false negatives are less likely than false positives here, so it’s likely best to save your time and others’ time. Needless to say, don’t rage quit, be honest and leave on good terms.

The previous two suggestions — reverse interviews and/or one-week trial period — will ideally prevent this scenario in the first place.

The career exploration phase is heavily undervalued

I went back-and-forth on whether a 16-month internship was a good use of my time and the allure of graduating early was certainly appealing. I’m so glad I decided to go for it though, because it significantly broadened my horizons and changed the course of my career. It wasn’t even a job I particularly enjoyed, but it made me realize what I valued and wanted in my career.

Shadowing roles, talking to people, reading thousands of articles only tell you what other people think and more importantly, are willing to share. Very few people can be completely unbiased and objective in stating the good and bad. Input from others is very valuable, but only when paired with your own experiences. Immerse yourself in a variety of jobs and industries in short internships. Nothing will never uncover as trying it out for yourself and getting a feel for how you feel about it.

The 16 month term is an interesting idea, because it is a more accurate reflection of work life than a 3–4 month term. However, the probability of finding your “best fit” in the first try is dreadfully low. In hindsight, I would recommend doing multiple internships, and more importantly, each very different from the other in terms of company or role to get broader exposure.

Exploration is a necessary part of anyone’s career. In fact, as I’m learning now, exploration in many other forms shouldn’t stop even after the initial years.

Software Engineer at Medium. Sharing my experiences and learnings from moving to San Francisco alone, being employee #1 at a startup and more :)