18 Trends That Will Shape Our Careers in 2022
From Digitally Native Jobs to the Pathless Path
👋 Welcome to the latest issue of The Jungle Gym – the newsletter that helps you build a more fulfilling career by integrating your work and life.
✨ If you’re a new reader, thanks for stopping by. Feel free to check out this introductory post, which explains what The Jungle Gym is all about.
📬 To get future issues delivered to your inbox, enter your email here:
It’s been quite a year. The war for talent raged, supply chains collapsed, crypto took off and lots of people (including yours truly) exited traditional employment to pursue something… different.
As we look ahead, many questions linger. Is remote work here to stay, or will the long-foretold return-to-office actually materialize? Will the economy stay strong, giving employees the confidence to quit, or will economic turmoil send workers back to their former employers?
Fortunately, we’ve assembled eighteen of the internet’s sharpest thinkers to reflect on the emerging trends from this past year and how they might shape our careers in 2022.
1. Digitally-Native Jobs
Rex Woodbury, Principal at Index Ventures
Today’s graduates are expected to hold between 15 and 20 jobs over the course of a career. Many of these jobs haven’t been invented yet: by 2030 85% of today’s college students will have jobs that don’t currently exist.
While some of these jobs will be the result of future technologies, millions of others are already possible: they’re digitally-native forms of work built on internet platforms. You can be a professional reseller on Depop, a gaming coach on Metafy, a community manager on Discord. You can build apps on Airtable, livestream on Whatnot, develop experiences on Rec Room. And, of course, you can make a living as a creator on TikTok, YouTube, and Twitch.
Gen Z is coming of age with a new mindset around work: Gen Zs want work to be self-directed and flexible, with financial upside. We’ll see a boom of “solopreneurs” and creators who don’t rent their time to corporations, but instead forge their own paths with hustle, savvy, and digital fluency.
2. Headless Projects
Mario Gabriele, Founder of The Generalist
Many of our most interesting and impactful projects will be multiplayer. We'll work together to create art, make games, tell compelling stories, and build new technology. Many of these initiatives will be fundamentally "headless," or lacking a singular leader. Instead, emergent groups will arise to tackle different problems and earn more responsibility through their successes. While there will still be a need for direction, much of that could be set bottoms-up, rather than top-down.
DAOs (Decentralized Autonomous Organizations) are probably the most obvious instantiation of this, but headless coordination can occur in other formats. The Wall Street Bets/GME farrago managed to move markets and take down investors without any clear leader or DAO to organize their efforts.
This type of coordination raises all sorts of interesting questions. How many people can headlessly collaborate? What infrastructure will be needed for orchestration? Are these unions transitory, or will they last for longer than a few weeks? How do you maintain, reward, and sustain communal effervescence?
I don't have the answers, but I'm intrigued to watch.
3. Building Careers Beyond Our Jobs
Deborah Liu, CEO of Ancestry
For too long, we have viewed our careers as the list of jobs on our Linkedin profiles. While this perspective has dominated for decades, these past two years have given us the space to view our professional identities in a more expansive way.
We have come to recognize that we are not just our jobs. And, as much as we may give ourselves to work, our jobs are only one small part of our overall story.
These days our career narratives are being shaped just as much by the:
Talks we give at conferences
Advising we do with startups
Writing we publish online
Non-profit boards we join
Companies are coming to recognize that these “extracurricular activities” do not actually compete with our work. Instead, they enhance our ability to perform it.
4. The Rise of the Chief Workflow Officer
Khe Hy, CEO & Founder of RadReads
When it comes to Hybrid Work, Cmd-C, Cmd-V doesn't work. You can't take a 20-person Staff Meeting and simply flip it into a Zoom call. The new normal has challenged companies to reconsider how they organize, collaborate, and communicate — creating a unique opportunity to rewrite some antiquated rules (umm, 40-hour workweek?).
Of course, this is no small endeavor as it involves integrating a cornucopia of new tools while changing the norms and expectations between complex beings (called "humans.") Individuals who can combine tech proficiency, systems design and emotional intelligence will rise to the top as organizations find themselves transformed for the better.
Over time, it would not be surprising to see this skillset formalized into a specialized function, with its own set of titles like Chief Workflow Officer.
5. DAOs Will Win the War for Talent
Vyara Ndejuru, CMO of Late Checkout
In August of 2021 4.3M workers left their jobs– the highest number since that metric’s been tracked. As more people exit their jobs to pursue fulfilling, creative, and collaborative work, what once seemed like strange employment alternatives will start to normalize.
DAOs (Decentralized Autonomous Organizations) are uniquely positioned to reap the benefits of this disruption. By offering their members flexibility and a strong sense of shared purpose, DAOs are finding new ways to harness talent. Whether it’s through empowering people with new forms of governance or lowering the barriers required to contribute, DAOs have the potential to reshape both how and why we work.
6. Staying Competitive: Remote Salaries and Benefits
Steph Smith, Director of Marketing at Trends.co
One of the hottest topics of 2022 will be location-based compensation.
Many remote-first companies have been paying location-based salaries for years -- including GitLab that previously had their compensation calculator public. Yet, when asked if fully distributed companies should pay people based on their location, the majority still responds with “no, same role, same comp”.
While “equal work, equal pay” might seem like the obvious answer, the reality is that the job market is… a market. If someone with double the talent asks for half as much, wishful thinking won’t get us very far.
Non-adjusted pay schemes also come with their own problems. If everyone is paid the same… based on what market rate? How does this impact the company’s competitiveness? What about local economies?
As a middle ground, some suggest a global minimum with an upward location adjustment for high cost of living (COL) locations. Either way, the conundrum of location-based pay will be a decision that all digitally native CEOs will have to make, and clearly, not everyone agrees on a “right answer.”
Location-based salaries also fit nicely into the growing push for open salaries, as employees look to rebalance information asymmetries. The good news for skilled talent is that they can also command leverage in this two-sided marketplace. To stay competitive, companies will experiment with offering a set of FAANG-level benefits, without the office. These can range from Uber Eats stipends to fertility support. Companies will also compete on flexibility using principles like 20% time or the ability to rethink vacation.
Remote work has opened the kimono and that doesn’t just mean where we work. It means every facet of work is rethought from how we’re paid to how we’re incentivized to stick around.
7. Simulations for Teaching Tacit Skills
Tom Critchlow, Strategy Consultant & Blogger
“Tacit knowledge can be defined as skills, ideas, and experiences that are possessed by people but are not codified and may not necessarily be easily expressed.”
The future of knowledge work is increasingly going to rely on tacit knowledge. Whether it’s knowing how to navigate the organization or how to build a great marketing campaign – this is the knowledge that will determine career success.
It turns out that the most effective way to acquire tacit knowledge is not through “professional development” programs. Research shows that the best way to learn these nebulous and hard-to-teach skills is through simulation.
Traditionally, simulations have been hard to construct. But as software continues to eat the world, we’ll see a huge explosion in simulations as the default medium for training. Facebook would have you believe these simulations will happen in 3D VR - in “the metaverse” - but in the near term, it’s far more likely that they look more like Wharton Interactive - a set of engaging business simulations to teach you MBA style skills more quickly and more effectively than a traditional MBA program.
Wharton Interactive uses the line “Serious Games. Serious Knowledge.” and I’d bet that is an apt description for the future of professional development.
8. Taking Extracurriculars Seriously
Brie Wolfson, The Kool-Aid Factory
Our year+ of working and playing from home has blurred the lines that once distinguished these activities. We took up hobbies, found communities, acquired new skills, and rekindled old ones. We started newsletters, joined DAOs, learned to program, got surprisingly into NFTs, finally started playing guitar, went deep on SQL, all out on backyard gardens, or all-in on roasting coffee beans. Our participation in these extracurriculars is not a new phenomenon, but making them such meaningful fixtures in our lives is.
Where work–especially in tech–promised to be the center of social lives, outlets for our skills, a reliable path to financial freedom, and the primary source of self-actualization, now our extracurriculars have proven to be capable of the same. They're not going anywhere.
Companies and managers will be asked to face–and very likely support–a fiercer-than-ever passion for and loyalty to these extracurriculars. And, they will be asked to do so with the knowledge that some of these curiosities, projects, and relationships are seriously competing with their Capital-W Work for time, energy, satisfaction, and maybe even sources of income.
9. Fractionalized and Composable Work
David Phelps, ecodao/cowfund
The twin forces of fractionalization and composability are empowering workers to put their hours of labor to better use.
When applied to work, fractionalization unbundles work into smaller modules while composability bundles modules into larger units of work. While these twin forces are acting across the economy, they are native features in web3 organizations.
Take DAOs. By fractionalizing core functions (treasury management, onboarding, governance, etc.), DAOs allow workers to fractionalize their time across many organizations. Meanwhile, a given task that a worker performs for a single DAO tends to be composable– meaning it can be applied to many other DAOs.
This is why web3 offers such a compelling value proposition for workers. Rather than giving all their working hours to a single organization, workers can spread their efforts among multiple promising projects. Meanwhile, workers do not have to silo their efforts to single organizations. Instead, DAOs allow them to cross-pollinate their efforts, to get extra leverage out of each hour of labor.
10. Speed of Learning & The Future of Income
Mercedes Bent, Partner at Lightspeed Venture Partners
New forms of earning are emerging faster than ever. Just in the last year, we saw personal tokens, securitized music, tradable bets, crypto, NFTs, vertical creator marketplace, social shopping, and direct-to-fan engagement take off as new forms of income.
The greatest income arbitrage exists when an emerging new form of income develops and few have the skills and platform knowledge to transact. To keep up with the increasingly fast rate of change, people will need to learn new skills faster than ever. This has made the speed of learning become the most prized skill someone can focus on improving as they pursue the future of income.
11. Giving Employees the Founder Treatment
Erik Torenberg, Co-CEO of On Deck and Co-founder of Village Global
A common startup idea is to “look at the services rich people have and find ways to democratize them to everyone else.”
We can apply a similar framework to the world of work: “look at all the benefits founders get and find a way to democratize them to employees”.
For example, founders get special professional development, peer networks, and coaching. Companies like Reforge, Enrich, and On Deck are extending programs like these to employees.
Many founders also get to diversify through angel investing. Employees are increasingly getting the same opportunity through VC scouting programs.
As the labor market tightens, employee job changes are increasingly resembling a fundraising process. Even before an in-demand employee starts looking, they will often receive a “pre-empted offer” full of creative perks to entice the individual not to look elsewhere. Over time, employees will get the same leverage that helped make the fundraising market more efficient for founders.
It’s not hard to imagine an employee telling a hiring manager:
"I'm going to take the next 3 weeks to talk to 10 companies—I'll let the market dictate price."
12. Community-Based Hiring
Kai Han, Founder & CEO of Pallet
Remote work has drastically changed how we interact with our professional networks. Where we once met people by attending networking events and master’s programs, we now build relationships through Twitter, Discord, and cohort-based courses. In this new reality, we find ourselves engaging in niche online communities more than ever before.
These communities are increasingly becoming conduits for opportunity. Members are using them to find new jobs, contract work, and even co-founders. As more tools get built to support these behaviors, online communities will become a critical element of career progression and talent sourcing.
13. A Boom in IRL Event Innovation
Amanda Natividad, Marketing Architect for SparkToro
As attending digital events becomes a standard consumer behavior, planners will need creative ways to convince customers to attend their in-person experiences. This means crafting events that are both novel enough to get customers to travel, and safe enough that they can attend without fearing infection.
Is it possible to create engaging attendee experiences that still account for vaccine requirements, ventilation, and on-site testing?
Fortunately, the past two years have featured plenty of great experiences that managed to toe the line. Dolce & Gabbana built a decked-out traveling Airstream that customers could book to visit their homes. Sephora and Kohl’s partnered to create an outdoor maze to engage beauty and makeup enthusiasts in a way that naturally enabled social distancing. With travel restrictions easing (for now), this boom in IRL event innovation only seems poised to grow.
14. Transformational Upskilling
Andrew Barry, Founder of Curious Lion
In most companies, learning and work are treated as two separate things.
L&D departments convince employees to take time from work to consume passive content, delivered in a top-down approach. The problem is– we don’t learn like that. We learn best by following our curiosity and connecting with others on a similar journey.
The good news for employees is that this kind of self-directed community-based learning has never been more available. The problem is, it isn’t integrated with work, which means employees need to do it on their own time or leave to pursue their growth.
To attract and retain talent in the coming year, winning companies will integrate work and learning. They will give employees opportunities to experiment within the context of their jobs and share reflections within cohorts of their peers. Rather than emphasizing the transfer of information, workplace learning will prioritize the transformation of learners.
Confucius once said that to become a leader, you must first become a human being. Companies that embrace this style of transformational upskilling will retain leaders ascending their path to personal mastery.
15. The Creator Side Hustle
Fadeke Adegbuyi, Lead Writer at Shopify
From freelancing and consulting to online selling and tutoring, the side hustle has become ubiquitous. But with the rise of creator platforms and the promise of making a living through the creator economy, this trend is accelerating in an interesting direction: side hustles are increasingly for building an audience rather than winning a client or customer.
Alongside a 9 to 5, it’s more common than ever to see individuals with a creator side hustle. Substack has fuelled a newsletter renaissance, with some popular publications being penned during evenings and weekends. On TikTok, there’s an entire genre of creators taking you behind the scenes of their day jobs––working as a Product Manager at LinkedIn or running a business cleaning residential pools––demonstrating that almost anything can be monetizable content. On YouTube, the same trend plays out through long-form videos.
These creator side hustles often transform into full-time occupations. For example, Alexis Gay worked at Patreon while creating humorous videos about the tech industry. Now she’s a full-time comedy creator and podcast personality. Mario Gabriele started his newsletter, The Generalist while working at a VC firm. After seeing significant growth, he decided to work on it full-time. In the coming year, we’ll see more employees dip their toes into the creator economy, and perhaps, go all-in.
16. The Distributed Reality Distortion Field
Cedric Chin, Writes Commoncog
You cannot make a good decision if you aren’t able to make sense of the reality around you. Unfortunately, sensemaking is only going to become more difficult the more plugged into social media we become — one species networked into a global hivemind.
The problem? That hivemind is host to a knife-fight of competing narratives. Whenever we open our phones, we subject our brains to the radioactive blast of an ongoing psyop war.
On the net, you may find arguments for any of these positions, of which the most compelling narratives spread the furthest. Some of these narratives are shilled by true believers; others are recruited to the cause as unwitting hosts for a mimetic sensemaking ideavirus.
A smaller group will see the psyop war for what it is, and they will deliberately shape the narrative landscape to their advantage.
It is this last group that is relatively new.
In the future, two things will likely happen: more people will realize they have the power to play narrative games to their benefit, and they will get better at shaping the dominant sensemaking frames in their respective niches.
Second, good sensemaking will only get harder.
17. Working with Your Friends > Working for Other People
Sari Azout, Founder of Startupy.world
As the boundaries between life and work become more porous and businesses transform into webs of interrelationships between people, we are seeing old social technologies (like co-ops) being paired with modern technologies (like tokens) to align the incentives of collaborators in new, digitally native ways. For many people, the idea of a long-term career is being replaced by a string of interesting projects with people they vibe with.
Most people would rather create a podcast or merch line with friends than on their own. They’d rather start an investment club or side hustle with their colleagues.
If working bullshit jobs at a corporation is about somebody else’s goals (“other”), and the creator economy is about you (“me”), what I’m describing here is a redefinition of “us” that acknowledges our primal drive for both autonomy and belonging. It is grounded in the well-being, both financial and emotional, of people, not a shallow culture that glorifies individualism while downplaying how the resulting self-reliance has deeply tarnished the human spirit.
Legacy corporate structures are outdated. As we make the transition from individualism to collectivism, there is a massive opportunity to build the picks and shovels for intimate, intentionally small groups of friends and Internet friends to build things together and create wealth together.
18. The Pathless Path
Paul Millerd, Author of Boundless
The default career path – the one that most of us have been following since the end of WWII– is no longer leading us to a desirable place. This path was a byproduct of industrial economies that supported pensions, lifelong employment, affordable homes, and nuclear families. But, as our economy changes, our scripts about work must do the same.
The alternative is what I call the pathless path. It is less of a script and more an acknowledgment that we are in a time between scripts. Until we land on a new “default path,” the only way forward is to create our own. This is quite hard. It involves defining success, grappling with insecurities, running experiments, and embracing a broader definition of “work” beyond what we can be paid for. It is a commitment to figuring out who you are, finding the work that matters to you, and doing it on purpose.
As companies experiment with new ways of operating, the possibilities for organizing our lives around work will increase. That means that the earlier we embark on our own pathless path, the better off we will be.
That web3 education project that I’m working on is publicly launching this week, but I wanted to give you all a sneak preview. If it looks compelling, we’d love to have you as early members of our community.
The Talent Collective is accepting new applications. If you’re considering making a move in the next few months, just fill out your information and we’ll start sending you intro requests from fast-growing startups in our network.
Note: for those of you who already signed up, we’ve been migrating from Airtable to a new system which is why you may not have heard much from us in the past month or so. We’ll be moving your info into the new system so we can start making some more matches for you all 🙂
If you enjoyed this issue of the newsletter, I'd really appreciate it if you could forward it to a friend, family member, or colleague who you think might like it too.
Or, if you'd like to share it on one of your social networks, that’s always great as well.
Until next time,