🎓Congratulations Class of 2022! Career advice for those starting careers in tech.

Why you should 🏄‍♂️ not 🪜

I don’t have Taylor Swift-level truth bombs to drop this commencement season. Nevertheless, I’ve thought deeply about what I have to say to this year’s new class of grads - especially those entering a job in corporate tech. How does one thrive in this world where the amount of data is doubling every 18 months? Where AI is enabling anyone to be an artist and express complex ideas in new ways? Where it seems like knowledge and intuition are more in demand than ever yet the way you acquire those skills is more complex? Surviving and thriving in today’s economy requires us to embrace change and prioritize curiosity - to do that, we need chapters and seasons and breaks between them to synthesize and recharge. What follows is my take on how to think about a career as the 2020’s come into focus. It’s a reprint with edits from a post I did a few months ago.

When you start your career, you are told it’s the beginning of some long upward journey that must always build on itself. You must “climb the career ladder” and stock art when you search for “career” is filled with professionals climbing up and up:

I graduated high school in the year 2000, so this pressure to be starting at the bottom of something intimidatingly tall was all the more amplified for my generation. The promise of the new millennium awaits!

Looking back on my career, this “career ladder” metaphor has done more harm than good. What pressure it places on someone when starting out! A career shouldn’t be a one-dimensional upward trajectory towards a pre-determined end goal. Side quests are fun. Where’s the sense of renewal? How do you account for time spent figuring out the direction to go? How about looking at life in distinct chapters and cycles?

Over my 16-year career, I’ve now mentored or managed dozens and dozens of new-to-career graduates. If you start with this career-ladder metaphor, the most common reaction is: “Huh? Am I supposed to think about that now? How long in the future should I be thinking?”

What, then, is a better core frame for a career in tech today? In my retro on my work anniversary, I had a turn of phrase: “Your profession is a wave to surf, not a ladder to climb.” I want to expand on this better metaphor and speak to folks starting out their careers: Think about your future as finding, catching, and riding the right waves. And the first one doesn’t need to be perfect - it just needs to get you in the water. 🌊

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🌊 Surfing Your Career Waves

So what do I mean by the fact that your career is about catching the right waves? Well, first off, it’s just a lot more fun to think of your profession this way vs. a dull ladder to climb. It’s inspiring and reminds you that you should be enjoying work. Beyond that, there are five career lessons that can be firmed up by the metaphor.

(1/5) It’s not about the one perfect wave. Get in lots of reps.

In a recent surf lesson, my instructor let me know that the day was going to repeat itself over and over. You catch a wave and once you are done, you catch another. Sometimes waves peter out when you didn’t expect it. Sometimes you wipe out. Sometimes you ride the perfect wave.

It’s about repetition and cycles. Especially early in your career, the more reps you get, the better.

Helen’s taken this career point to heart with three careers by her mid-thirties. But catching a new wave doesn’t only mean changing jobs. I’ve worked at the same company and around the same product for 16 years. But I don’t describe my job that way. I describe it as a set of great projects, each with unique outcomes that the team was striving for. Entering a new market. Scaling a new product line. Winning key customer accounts. Revamping an aged UX. Catch a wave, ride it, paddle out and catch the next. You and your skills are all the continuity needed.

Putting it into action as a new grad: Approach your first career conversation in a short term way. It’s OK to look out just 1 or 2 months for instance. Focus on getting more smaller reps.

(2/5) You should develop intuition about which are the best waves. Great project selection is the key to faster growth.

If you body surf, you know that the number one most important skill is looking out to the ocean and choosing the right wave to catch. There is an intuition to develop - the best surfers can see the epic wave developing far out to sea and get in the right position for it. This is way more important than any talent in riding the wave itself.

Careers are often the same way. Project selection, company/job selection, and industry/trend selection are some of the most important career decisions. Sometimes that’s easy - I had two job offers out of college - one to work on emerging collaboration software and the other to write printer drivers. Guess which made the most sense given the industry’s future. But over time, project selection has been a true differentiator for me. Figuring out what technologies are hot (e.g. ensuring I worked in cloud services), what trends were going to matter (e.g. chat-centric collaboration in enterprise SaaS), and what industries were going to mature (e.g. focusing on compliance after Enron’s collapse) made a bigger difference than any skill on execution. All this thinking positioned me to leverage luck when it came. I talk about this more in my advice to those adapting to Big Tech culture, where thriving requires having the right context and intuition about what to make epic. It’s too easy to ask yourself “How?” too often and forget to ask yourself “What’s next?”

Putting it into action as a new grad: In your first performance review on the skills you are working on, you should list “selecting epic projects to work on” as something you want to excel at. This gives you permission to research trends in the industry, company context, and emerging tech.

(3/5) You catch the wave; you don’t control it. Find trends to ride that are larger than you.

The art of surfing is to catch the wave at just the right time. Too early, and it passes you by. Too late, and it crashes on top of you instead of you being able to ride down its crest. And once you are riding the crest of the wave, it’s about capturing its power to propel you. You stop paddling and let the wave do the work. At that point, it’s way more about balance in the face of unpredictable movement than it is about hard work and energy.

Great, career-defining projects are exactly the same way. You have to develop intuition around what it feels like to be in the Flow - when you have found just the right match between challenge and skillset. This is about finding balance and then feeling like you are riding something larger than yourself; it’s not about working insanely hard. I talk about Flow more in my retro on managing during a pandemic.

Putting it into action as a new grad: Ensure you experience Flow - that match between challenge and skillset where you lose track of time and it feels like a mountain of productivity - in your first six months on the job. Trust me, it’s not just a little boost in productivity, but feels like a step-function change.

(4/5) Know when you are in the white wash. Listen to your boredom.

You can ride most waves past the time when they are fun or you are learning anything. The best part of a wave is that early and middle stage - riding the crest. After that, the wave slows down and the white wash pushes you forward, but you aren’t learning anything and it quickly isn’t as much fun.

This part of the metaphor really just means watch out for when you are bored. Some of the biggest gifts managers gave me in my career was to figure out I was bored before I realized it myself. Unlike a never-ending ladder, projects often have a long tail and it’s naturally human to stay with them longer than is appropriate. Mentors can help you figure this out, too, and Helen has a great post on the various type of mentors you should have in your work life.

Putting it into action as a new grad: Unlike school, there is no final exam and end of semester. There is no confidence that thousands of students have completed the same school projects before you. Spend the time to develop systems so you can detect when you are bored or when a project is no longer a wave to ride. If you feel like you have the safety to do this in concert with your manager, you’ve found a great team culture.

(5/5) Take a break between sets. The break is where you’ll grow the most.

So much of surfing is that break between sets of waves. You paddle out there and chill as you wait for the set of waves you can ride. You talk to a friend about how the ocean is treating them that day. This is an organic and natural experience - seasons, sets, renewal, and pauses.

Is there a culture in your organization to take the time to pause and reflect? Recharge? For me personally, I’ve become more introspective on my pauses as a result of the pandemic and that culminated in my sabbatical in early 2022. I see these as essential parts of my career, giving me perspective about how to drive wellness into my life, helping refine my purpose, or what gifts I want to give others.

Here’s my definitive guide on how to take paid time off: 🧘‍♂️✈️​Adam's Field Guide to Happiness: The Secret to Amazing Paid Time Off 🏖️🏃‍♂️ (mindthebeet.com)

Putting it into action as a new grad: Use the time off given to you and be pro-active about how you want to spend it. Counter interuitively to popular wisdom, it will make you a better employee and team member - recharged people are more fun to work with, and you’ll find the time to synthesize and come back with fresh perspective.

Wrapping Up

This metaphor doesn’t mean you don’t grow in your career. You can catch bigger and bigger waves over time. But a great career is about the journey, the project selection, the renewal, the pauses, and the energy capture of something larger than yourself.

So if you are just starting your career, don’t overthink it - just find the right first wave to ride. And, in a nod to a song that perhaps only my fellow turn-of-the-millennium graduates will get, don’t forget to wear sunscreen. 🧴