The Future of Work Looks Like… The Avengers

January 18, 2022
13 min read
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The ancient tectonic plates of the workplace are shifting. But like the plates beneath the earth, they shift so slowly that we don’t feel the movement. It’s only when there’s an earthquake-sized shift that anyone notices and the work culture as a whole changes.

There are some work-related stories and headlines that entered mainstream culture:

I’ve had over a dozen conversations with friends who work in tech, finance, non-profit, design, and advertising. They are done. No more putting up with the bullshit — low growth, incompetent managers, weak leadership, lack of flexibility — that they did before the pandemic (or during). These folks have little-to-no debt, a financial safety net and a wage-earning partner (the biggest life hack in an expensive city), and they value their time and sanity. They’re working four days a week, rethinking their careers (or even whether they want one), where they’ll live, and what kind of work they want to do. 

It’s a moment to ask the biggest questions of them all: Who do you want to become? What kind of lifestyle do you want to lead? "What is my purpose?"

The word apocalypse originally meant “the unveiling.” The pandemic tore down the veils and revealed rusted systems everywhere — rusted beliefs, rusted ways of living, rusted leaders.

Now comes the unraveling. The shedding of dead skin. A chance for a reimagination

My friends who have gone independent are making more money, working with the clients they want to, and maintaining a healthy schedule. No emails on weekends, no work calls during dinner, no Slack on their phone. And no way are they stepping back onto the career treadmill unless it checks off every box — and then some. 

The people I am describing have paid their dues. In the beginning of a career, it’s about building your portfolio and learning nonstop, getting a shiny company on your resume. You’re most likely living paycheck-to-paycheck (40% of Americans making over 100k do). Eventually, you get to a place in life where you don’t have to worry so much about where money is coming from. You have multiple skills that provide income, from small gigs to three-month retainers to connections at companies. The jobs come to you because of your name, reputation, network, and portfolio. 

These days, the crux is deciding whether you want a job or a career. “A career is a job you love,” said Elizabeth Gilbert. One of the most freeing decisions I’ve made is to not have a career in my next chapter. Don’t get me wrong — having a career, jobs I loved and poured every atom of my soul into, accelerated personal and professional growth. At this time in my life, though, I had to get off the treadmill, slow down, and look around. The game that I thought I was playing was no longer what I wanted. Also, I’m a first-generation Korean American, so the only way I know how to work is to completely tie it to my self-worth. This makes for a good hire. But it’s something I have to unlearn.

The breaking point for careerists is the onset of diminishing returns, which was amplified by the pandemic — when you have the sudden feeling that your contribution outweighs the salary and time spent; when you are no longer “mission-driven”. It is jadedness. Play a game long enough and you start to connect the dots on realities that most people would never see. You’re on the inside. You start to realize that there are charlatans in your industry, people with fame and power, yet all they do is take credit for other people’s work.

There’s a scene in Wall Street with Michael Douglas and Charlie Sheen, where young Sheen starts to realize what game he’s playing. One can argue that he knew, but by being on the inside, being with a player like Douglas, revealed rottenness and manipulation. Every — and I repeat — every industry is like this. The people at the top are better at maintaining their illusion of leadership than actually making things.

Careers are a useful and fruitful function to jumpstart a life. The most successful people I look up to all had careers that set them up to build a business. Whether we do it forever is up in the air.

Back to the convos with friends. 

The undertone of these conversations about the future of work sounds something like this: “I just want to work with thoughtful, kind people on projects that I care about. It doesn’t matter so much the industry or product, as long as the people are solid.”

What games are available now?

The most generous assumption I can make right now is that you and I want similar things in life: a healthy body, a calm mind, a loving partner, a hobby or two, close friends, a home, and a sense of purpose and fulfillment. We teach. We volunteer. We feel useful in our purpose. We host dinners for friends by a fire. Puppies running around. The life.

The question is, how will we build this life? How do we earn this? Which game are we going to play?

The game that my parents played was straightforward and normal for immigrants. Leave South Korea/Brazil. Come to America (New Jersey, of all places). Get an education. Get a job. Stay at the company forever. Work hard. Save money. Then you’ll be rewarded. You’ll be okay. They’re in their 60s and nowhere near okay.

Over time, the promises lost their durability and then became completely insufficient. The dollar is losing value, 40% of all US dollars were printed in the last year, interest rates have tanked, homeownership is becoming more unattainable, leadership is nonexistent, and some of my friends don’t see a future in the U.S. 

The games available to my generation are changing. It changed because of technology and it became apparent by the pandemic.

For example, my friends who worked at tech companies like Instagram, Google, or Facebook early on were smart to get equity and hold on to it. They got those jobs because of their college education, location, networks, and future-facing skills, like product design or coding. The money they’ve made is a stepping stone to building generational wealth. This is important especially for immigrant kids. That game is widely available; previously it was reserved for those who work in (mostly) coastal cities and in tech. Remote work changed this for a lot of people not privileged enough for this kind of access. Talent can be pulled from all corners of the world, especially from Asia, Africa, and India.

The game that designer friends play is to go to a prestigious design school, then join an agency (because schools work with agencies for job placement). They learn how work is made and how clients behave, and they add interesting projects to their portfolios. Some stay in agency land and others leave to go in-house. Others start their own studios. 

The game that engineer friends play is to learn a coding language and work at a tech company. Glassdoor claims a junior engineer in NYC makes $66K on the low end of average. Some companies are offering six-figure salaries to graduates straight out of college. If you’re 21 years old and making $66K, you’re probably doing better than your parents did and certainly making more than designers and writers out of the gate. That number goes up astronomically as you advance in your coding and work at bigger and more famous companies. All you need is one famous company on your resume as a stepping stone to future opportunities. Getting a job these days is easier, too, because the demand for engineers is so great and programs like the Bloom Institute of Technology provide the bootcamp and job placement.

The game that a lot of Gen-Z kids are playing is the TikTok game. The influencer game. The YouTube game. What they’re hoping for is to get picked. To go viral. And to use that viral moment to become famous. Fame to them is the means to money and a desirable life. But so many kids are realizing the cost of this game

And there’s a whole game being played on the internet with NFTs and blockchains and DAOs, where JPGs have sold for millions of dollars, where anonymous groups act like a VC fund, and the conversation around what is art and what is its value is transforming every week. But that’s a rabbit hole you’ll want to go down on your own. (I wrote about my experiences here.)

On one hand, my friends cannot see themselves ever going back to a company full time unless it ticks off every box. Some will only join a startup if that startup idea solves a meaningful problem, like healthcare or education or climate crisis. They’ll gladly take a pay cut. Most important of all, they’re asking: Are the people kind? Do I want to spend time with them? Is this a calm environment? Will I learn? Because they’ve dealt with their fair share of narcissistic, sociopathic leaders and toxic work environments, they can spot red flags from miles away.

On the other hand, none of us are so wealthy that we can avoid working. And purpose is central to life. I hope you meet people in life that have seemingly everything one could ask for — health, wealth, homes, and millions of dollars — and still be miserable. It is humbling to witness and important to learn from. You need purpose and you cannot buy it. If you’re reading this, you’re probably someone who gets paid to use your imagination and creativity, so you need to feel purposeful in what you contribute and do with time, or else we’ll spend 18 hours a day on Twitter pretending to be politicians or healthcare experts. 

So, which game are you playing? 

A long game? A short game (nothing wrong with that if you’re clear about it)? A status game? A money game? Wealth games? Career game? This thread by Julie Zhou is insightful.

Imagine the future of your work to be like...

Walk with me for a minute.

The future of work will look like… The Avengers. Let me preface this by saying: Not everyone will want this or be cut out for it. 

Especially for people with families and kids to take care of, working at a company will be the kind of safety and stability that they depend on, especially in America, where retirement and healthcare are tied to the job. Otherwise, you either get lucky, win the lottery, or build a business.

What I am asserting is that as new technologies evolve — and as our attitudes to work, careers, and productivity change — it widens the boundaries of how we earn a living, how we create products or businesses, and how we connect with talent.

On the flip side, doctors and dentists have to play the same game that has been played for decades. So do anesthesiologists and lawyers. 

For writers, designers, engineers, illustrators, animators, career coaches, etc., the game is evolving. The opportunity to learn new skills, join communities, build a portfolio, and get skin in the game is easier than any other time in history.

Big tech companies are already catching onto this, giving huge salaries or bonuses to retain talent. I have a few friends that literally all they do is draw mythical things, abstract objects, and gradients at a tech company making $150k+ a year. Junior engineers are making six figures out of the gate. There aren’t enough brand designers to service all the new brands being built, so they can charge insane rates. Wild times. 

And the friends that are like solo Avengers have what I described above: a strong portfolio, a network, character, etc. One email with a couple of dozen people BCC’ed to it can generate multiple conversations for month-long retainer gigs. These talented folks know their worth and refuse to join a company full-time. One, they can make more being independent and two, they can free themselves from the internal games of a big company.

A close friend started her own boutique agency, hiring the people she wants to work with, and taking on projects that can set her up financially for an entire year. But she had to have multiple career moments to have that level of expertise and leadership.

What these new edge cases provide is more flexibility from the industrial mindset trap. So much of how we work is informed by the factories of the industrial era. 

Then there’s the salary ceiling. In many industries and job roles, in order to make more money and advance in your career, you have to manage people. 

Imagine it like this: You’re someone with deep experience. Because of your name, your reputation, the quality of your work, and how you show up online, companies reach out to you for projects. You personally know brand strategists, photographers, writers, animators, and coders. You reel in the projects, get a budget, and pay your friends 2x or 3x what they would normally make. You get to work together. Happy. Healthy. Fun. Each person has a unique superpower that is needed for solving this challenge. You’re essentially a Nick Fury, the founder of the Avengers. You’re a project manager. You don’t code or write copy or design things. You manage contracts and timelines, clients and processes. This will always be an available role for senior-level people. And they’re massively in short supply.

Or you’re someone who, like me, has worked in a variety of industries. You have a set of skills that companies need. You don’t want to manage anyone. You are a super independent contributor who doesn’t need to be managed. You know the game at a high level, can speak to executives, and deliver quality work.

How does this dreamy idea that (truthfully and at present time) will be reserved for one in a million creatives? What about the person with immense talent and no connections? 

This is where I stress the lifelong value of caring about your portfolio. Your resume of projects and the things you built, edited, managed, and shipped. 

This kind of life is earned through hard work, integrity, and character.
Relationships (who knows you; who trusts you).
Mastery (deep expertise).
Character (“I like working with this person”).

You choose who you get to work with. You have a portfolio. You have a network. You have a reputation. This doesn’t mean you need to be Twitter or Instagram famous. In fact, the people I most admire are the quietest ones on those platforms. You would never be able to guess that they’ve designed and built some of the largest, most successful brands in the world or sold startups to other companies.

My generation of creative people is at a major advantage. You can be playing your own game, building your network, and others will want to be part of it. You can get so good at what you do that companies will need you more than you need them. With the potential of blockchain, remote work, DAOs, and Web3 buzz, I feel we're at the beginning of something new.

We don’t mine coal or clean windows of skyscrapers. We literally sell our thinking, our ideas. We combine imagination and craft. What a life. Remember that.

There hasn’t been a more ripe time in history to achieve this level of autonomy. It is, I think, just the beginning for my generation especially. For the learners and those who work very hard, this life is widely available. And I find it incredibly exciting as I enter 12 years of being a writer, having worked in five different industries, and realizing that this is all very much the beginning of a new frontier.


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