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The 3 rules to making big career (and life) decisions with no regrets

Uncertain about changing jobs? This former Google tech guru reveals the guiding principles that have helped him navigate life-altering choices.

The 3 rules to making big career (and life) decisions with no regrets
[Source images: Denis Novikov/iStock; Anton Darius/Unsplash]

I started my career in academia, where mentoring bright young minds is commonplace. Years later, mentoring and coaching others was one of the best parts of my job as a vice president of engineering at Google, and I tried to spend as much time on this passion as I could afford. Through countless conversations over a decade, patterns emerged, and I found myself dispensing the same three pieces of advice again and again to navigate a career with clarity—learned from my own and my mentees’ experience. So let me share them with you.

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Pick your next job to prepare for the one after

How should you think about your next job? First, think hard about the one you want to have after the one you’re currently exploring. That allows you to identify the gaps in skills, experience, etc., you will have for that job. Then, to progress toward your long-term goal, your next job needs to allow you to close some—ideally many—of those gaps. It is essential to realize that the forces of nature in recruiting will often work against you. Recruiters and hiring managers look for candidates who have already demonstrated success in the skill or role they need. Therefore, they are likely to offer you a job where you continue to do what you have already done successfully. If that aligns with your long-term goals, you are lucky, but if it does not, you need to proactively pursue jobs that help you close the gaps.

Consider the 3 most important aspects of your next job

When people approach me to share a new (internal or external) job opportunity they are considering, their focus is usually entirely on the actual job or project (and the compensation, if relevant). Unfortunately, they neglect two critical aspects of job satisfaction. First, data shows that your manager makes a big impact on your job satisfaction—a lousy manager will make the best project a nightmare, and a great one will uplevel all aspects of a job. Second, your team members and peers are also hugely important, both from a social perspective (just consider that you will spend roughly as much time with them every week as with your family) as well as from one offering an environment where you will be able to learn the skills you need for your next job from them. The actual project you work on has considerably less effect on your job satisfaction than those two factors, yet candidates tend to spend not enough time interviewing their future manager, and often miss taking a more detailed look at their future team. As a hiring manager, I always offer candidates time with their future team before committing (e.g. they join team meetings, or sometimes receive references to learn about me as a manager).

Try the “look back on your life” rule

When faced with a tough or scary career decision (or other life decision)—like moving to another country, or switching industries—picture yourself old and gray, telling your grandchildren about your life. In that reflection, if you take the path you’re considering, will you be more likely to regret that path or regret not having taken it?

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When I worked in the Zurich office of Google, an old boss invited my wife and me over for dinner. He and his partner lived primarily in Germany and Italy, but to our delight, they served us exquisite, homemade, authentic Japanese dishes. As it turns out, they learned to prepare such a meal during a two-year stint living in Japan. Although living there was quite challenging for them, in retrospect, it led to many great experiences and was net beneficial. On the way home, my wife and I came up with the “looking back on our life” rule, and applied it to a question we had debated for years: “Should we leave lovely Switzerland to live in Silicon Valley?” Looking back on our life, there is no way we would regret living in California. Worst case, if we disliked it, we would move back after a year or two (thankfully, we have enjoyed our time here so far).

After 14 years at Google where I enjoyed the challenges of building up Google Travel and Google Shopping, it was this same perspective that guided me toward my next adventure, recently joining Coda as their Head of Engineering. I was intrigued by their wildly ambitious mission to reimagine what documents can be by enabling anyone to build a doc as powerful as an app. Looking back on my life, even if we fail (which we’re not planning on!), I will be proud of the boundaries pushed and what I will learn from tackling this endeavor, which is likely exponentially more than what I would have learned had I stayed comfortable in the exact same role for many years.

It’s important to acknowledge that as a software engineer, I am privileged to even have these options. If you’re in a similar field, you likely have a career that generally affords you geographical flexibility and salary ranges that can support families. As you contemplate your next move, don’t take that for granted.

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Oliver Heckmann is the head of engineering at Coda, an all-in-one doc for teams. Previously, he spent 14 years at Google, where he worked on Gmail, Content ID, YouTube and the creator ecosystem, Google Shopping, and Shopping Ads. Most recently, he was responsible for Shopping and Travel at Google, having worked on a portfolio of travel products, including Google Flights and Google Hotels.


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