Bankers in the 90s, consultants in the 2000s, tech companies in the 2010s, Cryptofiles and TikTok artists in the 2020s?!? The careers that attract the smartest and most ambitious is often a never ending cycle of trends and infatuations. Like moths on a porch light, they flock to the brightest glow. As an early thirty year old who took a rather non-traditional, nor all that celebrated, path in my early career, I’m often fascinated by those that jockey for positioning to get into highly selective and highly celebrated jobs. When I was graduating from Penn State’s Smeal Business school I didn’t have a shot at all to join the ranks of the investment banking elite that many of my Ivy league friends sought. I could have busted my bum and tried to jump into the rushing waters but even then I would have likely been relegated to a second or third tier bank. I never really envisioned myself as the winner of a gladiator style bake off anyway but rather a creative thinker who could maneuver quite effectively to build a meaningful career. Back then, post financial crisis and well into the economic rebound, investment banking was the golden step - seen as the career move that gave you both the highest near term earnings and the greatest post two year stint optionality. Those two attributes (earnings + optionality) tend to lead the way for ambitious but often confused recent graduates. Many of us desirously infallible, attempted to make the career decisions based on the loud voices of industry pundits, peer influence and social confirmation. Ironically, however, many of the in vogue paths are often in their 11th hour of glory - when the juice has already been squeezed and the secret is out. So the question becomes, do you go by way of the consensus or do you take the path less traveled and more unknown?
Sometimes the best way to get somewhere is to take the straight path and build up your 10,000 hours of expertise, but other times, the best way to get somewhere is to start by taking a detour. I often suggest the detour.
I don’t know why but people like asking me for career advice. My disclaimer is usually that I know nothing but that I have a frame work for the career decisions I’ve made. It’s simple: What do I want to learn and from who? Once I’ve learned that thing, what do I want to learn next that compounds or compliments that prior thing? With that framework in mind, here is how I would answer some of the most frequently aspired roles in 2021:
“I want to get into venture capital.”
My answer: You should go learn how to think differently. Go become an online artist and surround yourself with brilliant creatives, learn to speak the artists language, become hyper successful at putting out great artistic content and create a community, story and narrative around what you believe and then go raise capital to help fund that ecosystem for which you have deeply held beliefs. WALA, you’re in VC!
“I want to get into sustainable finance.”
My answer: go learn what’s not working and why it doesn’t work at a waste management company on their innovation team and help them think through recycling and repurposing efforts. Once you’ve built relationships with the innovative businesses working on sustainable closed loop systems, built an expertise, brand and narrative around what’s not working, go raise capital to help fund those businesses and learn how to do it right. WALA, you’re in sustainable finance!
“I want to be a product manager for a tech company”
My answer: Go learn how to do sales at an early stage company. The customers will tell you that the product sucks or lacking in some areas. You’ll work with your engineering team and help improve the product and sell through it. You’ll manage that communication to the would-be customer, promising them that the best is yet to come. The next job you have, you’ll be the best product manager because you’ve done sales OR you’ll realize running sales is way more fun than deciding that round button should be made rectangular and you’ll learn how to manage other product managers from a revenue generating seat. WALA, you’re basically a product manager!
“I want to work in crypto”
My answer: Take $20,000 (or some number you’re comfortable with losing) and build a crypto fund of your own. You’re the only investor in the fund and its only your money so you don’t have to worry about managing OPM (other people’s money). Set up the rudimentary systems of trading, build your portfolio, document your experience and share it on a substack - referencing other great crypto folks. Be bold. Once you’ve done that, you share the experience of trading and staking crypto with some aspiring blockchain developers working on new tokenizations or projects and they’ll want you to hang around the hoop and build with them. WALA, you’re now in crypto!
Survivorship bias has glorified certain career paths. When we think of bankers, technology entrepreneurs, crypto legends, and more we think of Jamie Dimon, Zuckerberg, Bezos and Brian Armstrong. We think about how THEY got there and how the successful found their way to where they are. We often don’t think about the graveyard of failures and flops. It wouldn’t be as fun and certainly wouldn’t be as inspiring as its not the beautiful story we all want to envision. We have to hold the glory in our near sight or else we won’t start the mountain ascent. The challenge, however, is that you are YOU and THEY are already taken, so you have to find your own lili pads to hop on.
It’s no longer in fashion to boast about your high salary and sizable year end bonus when it comes with soul-crushing 80 hour work weeks, deep spreadsheet jockeying that lead to endless analysis and spoiled weekends. Did I mention the early onset hair loss? Is that an amenity or an asset?! I’m not shirking hard work or responsibility - quite the contrary. I very much believe you must work hard but you have to work hard in the right way and work hard to carve your own path. For if you know the path you’re on, then it’s probably somebody elses’.