Cultivating superpowers to maximize career trajectory

What watching Andrew Yang's ascent has taught me about cultivating superpowers

Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.

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One of the simplest ways to maximize the output of an entrepreneurial career is to cultivate a superpower (a skill in which you are world-class) and apply it in different contexts and at different scales. 

Most people go their entire careers without discovering or cultivating a true superpower. As I write this, I’m still trying to figure out what mine could be.

It wasn’t until Andrew Yang’s presidential run that I understood the value of cultivating a superpower and applying it in different contexts and at different scales.

Most people now know Andrew Yang as the upstart 2020 presidential candidate, now running for Mayor of New York City. Before that, some of us knew him as the founder and CEO of Venture for America, the fellowship i joined in 2013. 

When Andrew told us he was leaving VFA to run for president, few expected that he would end up as one of the final seven democratic nominees on the national debate stage. We all knew it was an incredibly long shot. But as we observed how his campaign was gaining in popularity, it seemed eerily familiar. 

Andrew was simply applying his superpower – which he exercised and honed while building VFA – to a political context on a much bigger scale.

Andrew’s superpower is that he can identify big, complex problems that are hiding in plain sight. He then uses his charisma and relatability to help masses of people quickly understand things they’ve experienced or observed in the context of a higher-order problem. He offers a simple solution which everyone can quickly grasp, and is able to galvanize masses around the problem and his offered solution.

With VFA, the problem was that “the majority of our talent is flowing into finance/consulting/law and not enough talented young people are engaged in job-creating enterprises in our communities.” This resonated deeply with entrepreneurially-minded college graduates in 2012 and 2013 like myself. We saw our peers going into these professional services and felt the gravitational pull ourselves despite wanting to be more entrepreneurial. Yet we didn’t quite have the words to explain it. Andrew helped us understand this tension we all felt on a personal level in the context of a higher-order national problem. He offered a simple solution – a model like Teach for America but for aspiring entrepreneurs to work at startups in emerging startup cities like Detroit, Cleveland, and Philadelphia.

Andrew’s ability to concisely explain this problem in a way that quickly resonated with college graduates and wealthy donors galvanized a movement behind the idea. The Kool-Aid was very strong – in those first two years, over a hundred recent graduates excitedly moved to cities where none of their college friends lived and made salaries under $40K. 

Fast forward to 2018 when Andrew was starting his presidential run, and did the exact same thing. He identified a big problem hiding in plain sight – that automation was transforming our economy far faster than anyone anticipated and the rate of job automation would outpace new job creation. He offered a simple solution – Universal Basic Income (rebranded as a “freedom dividend”) where every American would get $1K per month. He used his superpower in eerily similar ways to galvanize a movement behind his campaign. 

The only differences between how Andrew applied his superpower with VFA and his presidential run was that (1) by the time he was running for president, he had sharpened it, and (2) his presidential run was applying it on a much bigger scale. 

I’m not sure if Andrew would articulate his superpower the same precise way that I did, or if he’d call it a “superpower.” But he’s definitely self-aware of this ability. That’s the only thing that can give someone the confidence to commit to running for president a full year-and-a-half before the democratic primary.

Being self-aware about our superpowers and finding new contexts and scales to apply them can help us create sharp inflection points in our career trajectories – much like Andrew going from the CEO of a 20-person non-profit to being one of the top 7 democratic presidential candidates.

This begs the question, “how do we cultivate our own superpowers?”

I think of superpowers as a skill in which you are world-class (as in you’re one of the best in the world). Given that the world is a big place, it helps for them to be pretty specific. Potential superpowers sit at the intersection of three things: (1) things that make you weird, (2) elite talents, and (3) practices which give you energy. Skills that sit at the nexus of those three things will come naturally, have a high ceiling, and will always be improving.

Things that make you weird

If a superpower is built on some of the traits that make you weird, you’re more likely to be differentiated and world-class. It also means that your innate tendencies will effortlessly make you better at the it.

For example, one of the things that makes Andrew Yang weird – a proclivity for analogies – is an integral part of his superpower.

If thrown front of a group of people without a script, Andrew would start making analogies. Back in 2013 at VFA training camp, Andrew would address the fellow class each day. His addresses almost always included an off-the-cuff analogy, some of which were misses (one day he went on a 2-minute tangent about how entrepreneurship was like going into a cave and coming out with a golden pear, which left many of us scratching our heads). He once referred to me as a “hammerhead shark” when introducing me to pitch my startup to 50 investors. Not all of his analogies were winners.

Andrew uses analogies to make complex concepts resonate. With VFA, he repeatedly used an analogy about cake to explain a complex problem, which is best explained in a 2016 interview about his book, Smart People Should Build Things, 

The first part of the book is pointing out that smart people, right now, are not really building things...We’re sending the majority of our talent to a professional services layer that serves primarily mature organizations. It’s like a lot of icing… and not baking the cake.

Andrew’s presidential campaign was powered by analogies. He reframed Universal Basic Income as a “Freedom Dividend,” suggesting that if the wealthiest companies provide dividends to their shareholders, then the wealthiest country should provide a dividend to its shareholders (AKA citizens). He said that technology was like the oil of the 21st century. He referred to the impact of big tech by comparing them to a “claw” sucking up commerce from local economies. He used these analogies so frequently that he became the meme candidate, and you can still buy Andrew Yang Claw Art.

Watching all of this unfold, it was remarkable to see “Andrew being Andrew” lead to so much success with the campaign (albeit he was getting a lot more polished and staying on message more).

Elite talents

Something can only be your superpower if it’s something that you’re really good at. 

I enjoy practicing basketball, and I’ve always been a little weird in trying to create structure, which meant I had really great footwork on the basketball court. So why couldn’t my superpower have been related to basketball? Well, turns out that I didn’t have the talent. 

Just because something is based on what makes us weird and we enjoy practicing it doesn’t mean it should be our superpower. These are unproductive-but-fun skills – they’re things that likely will bring us joy and come pretty effortlessly, but won’t be productive in our career trajectories.

A good question to ask when reflecting on elite talents, is “what is something that I genuinely think I could be world class at?”

Answering this question requires self-reflection, feedback from others, and learning what “varsity” looks like regarding the skill. Using the basketball analogy, there was definitely a point in my life when I thought I could be a world-class basketball player. But then I started playing AAU and received a rude awakening – my peers who were “elite” were worlds better than I was. Getting exposure to people who are truly elite at something can help us calibrate what “world class” might look like and if it’s something in the cards for us.

Practices which give you energy

Something can only be your superpower if you get energy from working on improving it, even without any pay off.

Malcolm Gladwell posited in Outliers that it requires 10,000 hours of practice to become world class at something. And even if you were to become world class at something, without practice, that skill would erode. 

Therefore it’s worth thinking about the things you enjoy practicing even without the gratification of an outcome. 

For example, despite this is my 24th consecutive weekly post, my writing has only improved marginally. Why? Because I do not get energy from practicing writing without an outcome (publishing a post). It’s not the act of writing that I enjoy – it’s the challenge of trying to find structure in complex concepts like entrepreneurial career-building. I get energy finding this structure, which usually manifests in pressing “publish.” Since I do not get energy from practicing writing without gratification, I could never be a world-class writer.

When it comes to Andrew Yang, he’s an extrovert. Earlier in life, one of his side hustles was being a nightclub promoter. He gets energy from engaging with large groups of people.

When on the presidential campaign, regardless of the outcome, I imagine Andrew enjoying and getting energy from even the smallest crowds of 20 people attending his events, even when “success” seemed improbable. Through his time building VFA and running campaign, Andrew has addressed crowds of people literally thousands of times. Addressing and interacting with a crowd is a practice that’s required to galvanize people behind a cause. And it’s a practice I think Andrew would enjoy doing even without a cause.

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Identifying superpowers requires introspection, feedback from others, experimentation, and learning what “varsity” looks like.

I think identifying superpowers often happens in retrospect. It’s not necessarily a sequential process of identifying your potential superpowers and then working on them.

But focusing and reflecting on these three things  – (1) things that make you weird, (2) elite talents, and (3) practices which give you energy – increase our chances of cultivating a true superpower.

If you’ve found your true superpower, then good for you! You should go apply it in as many different ways as you can and have a great career.

For the rest of us, the exploration goes on.