5 Career Lessons From a Decade of Working in Tech
On his 35th birthday, Aubrey Chapnick writes on what it actually takes to carve out a successful career.
I have approximately 16,308 days left on Earth according to Statistics Canada’s average male life expectancy. I’ve lived 44% of the time I’m likely to get.
It’s a strange thing to see your life in terms of a number that only goes down.
I’m pretty healthy, a former competitive athlete, don’t really drink, and workout frequently, so the real number is hopefully higher, but doing the math is still a sobering experience.
While “what I wish I knew” articles like this often feel like narcissistic navel gazing, I tend to still like them for three specific reasons.
I spent a large part of my 20s throwing darts at the wall hoping something would stick. I wish I had enjoyed it more and felt better about myself in the process.
When you are starting out, you feel like everyone knows some secret you don’t, and the proxy for that is the size of their bank account relative to yours. That couldn’t be further from the truth.
I believe the value of experience is to use it for the benefit of others, and since I’ve done a lot of random and stupid stuff, maybe someone, somewhere can learn something from my mistakes.
Since I did one of these a few years ago, this is incremental and additive. Five things that have become more crystallized since.
What You Must Subject Yourself To Is a Function of How Much Cushion You Have
Whenever someone reaches out for career advice, I often ask how much of an emergency fund they have. This is a personal and intrusive question, but it’s the most important thing that matters for career optionality other than your skills and reputation.
I’m not saying you shouldn’t spend money and enjoy yourself when you are young. I believe in that more now than I ever did. What I’d suggest is you work as hard as you can to build a cushion of at least a year’s savings. Worried about getting fired? It will help you sleep. Want to try something new? You can. Something big breaks? You can cover it.
When I was 27, I spent a lot of money on a one-bedroom shoebox in midtown Toronto. I could easily have gotten something less nice and saved more. I wanted to be in a cool, new condo with a gym and near nice restaurants but worked in consulting, so I was never there. You don’t realize how much a choice like that shapes every decision that comes after it until you’ve made it. If you want optionality, keep your housing and transportation costs as low as you can stand until you’re ready to give it up.
Your Success Is the Inverse of Taking Injustices Personally
There have been many situations over the last 10 years where the work world has not been fun. Stuff happens at work. It’s a feature, not a bug. It’s going to happen to you more than once too.
Jeff Bezos once said you should aim to enjoy 50% of your job. I think I’m doing much better than that.
When difficult injustices happened to my younger self though, my first instinct was to leave. New company, new manager, new industry. In retrospect that wasn’t always the right call. When you’re subject to any form of professional injustice, take a step back and ask what you want from your current situation and whether it’s aligned to where you’re trying to go longer term. If it is, the question becomes how to make the situation work until enough data or a genuinely better opportunity arrives to make leaving an option you can’t ignore.
The part nobody tells you is what leaving costs. Every restart buys you a year or more of relearning who matters, how decisions really get made, and where the bodies are buried, along with questions about your ability to hold down a job. I’ve made this mistake and would rather you didn’t.
The Higher You Go, the Trade Between Growth, Comp and What You Give Up Can Converge
If you want to become more senior, make more money, and accumulate more professional relevance, you’re going to have to give up other parts of your life. You cannot have everything at once.
I work a lot more now than I did when I was younger. I’m more senior, I make more money, I manage people, I have a side hustle, and there is more pressure to perform. I’ve given up things I once enjoyed doing and I’ve been ok with that up to this point.
At some point in the climb though, the incremental increase in responsibility and the incremental increase in what you’re paid to carry it can start to separate. A lot of people don’t think about that. A VP I met with recently framed it in a way I keep coming back to: At every jump, you need to evaluate if that incremental increase in comp and responsibility is worth what you are willing to give for it. It’s completely fine to decide you don’t want to be a C-level or a VP or a Director. You just have to actually decide.
You Need to Become a Good and Accurate Self-Critic
One of the most important parts of being a leader is holding other people accountable for actions and results. The worst thing you can do is wait for someone else to make you accountable to yourself.
As you grow, you learn when criticism is warranted, when it isn’t, and how to take feedback productively. Whenever you screw something up, there will be things inside your control and things outside it. One of my old managers told me you should be the hardest critic of yourself, but only when there’s something to be critical about.
Have Goals Beyond Money and Reassess Them Often
I never wanted to be in business. I wanted to be a fighter pilot. After that didn’t work out, I had no real career goal other than getting to a certain annual salary number by a certain date. When it happened earlier than I thought, I got thrown for a loop. Psychologists call this the “Arrival Fallacy”. I call it Aubrey’s big f-ing existential wake-up call.
Money is important. Probably more important today than ever because everything is so freaking expensive. But money on its own is not as important as what you use it to do, and whether what you use it for actually matters to you. You are going to trade a lot to get it.
I still care a lot about how much I earn and expect to be paid appropriately for what I can do. However, with only 16,308 days left in my life account, I’m thinking a lot more about what the money is for and how I can use it.
A Bonus: Don’t Be a “Me vs Them” Person
Almost all of my career has been spent in cross-functional or advisory roles, which invariably means having to get things done through people who don’t have to listen to me. Younger Aubrey got frustrated when a colleague didn’t do what he wanted and started thinking about the relationship in adversarial terms.
Older Aubrey has come to realize being a “Me or Us vs Them” person is incredibly unproductive in every respect. It hurts you and it hurts others. Scott Galloway calls this insanity. I agree. It doesn’t matter if someone doesn’t agree with you or won’t do what you want initially. If you think they are your enemy, you will never get anywhere. That is true in business and it’s true in life. Start with a positive assumption. Be a good teammate. Assume everyone is doing their best until you have reason to believe otherwise.
Here’s to the next 16,308.
Aubrey Chapnick is a Toronto based professional with a background spanning Product Marketing leadership roles, financial writing, management consulting, sales and capital markets. He has over a decade of experience across fintech, banking, SaaS and holds an MBA from the Sauder School of Business at UBC and is a past Globe and mail business education contributor.
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