Nine Trends That Will Shape Our Careers in 2021

💌 The Roundup // 020

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Dear friends,

Before we get into it, I just wanted to say: thanks.

It’s been a strange year for all of us. Socially distanced from friends, coworkers, and relatives, we all needed a coping activity. Some baked bread, others played chess, and me– I got really into writing this newsletter.

Writing online can be a lonely pursuit, punctuated by moments of intense overexposure. At times this year, it definitely messed with my head. But the encouragement you gave, and the referrals you made helped me sustain the motivation I needed to keep this up.

Some of you know I started out my career as a screenwriter. Turning my back on that path was one of the worst periods of my life. This year is the first time since then that I can feel my passion for writing returning.

Thanks for kindling the flame.

Until next year,


The Rundown

Here's a quick summary of what this issue will cover:

Featured Essay

🔮 Nine Trends That Will Shape Our Careers in 2021

From living online to live-streaming work, here are nine trends from the year that will change the way we build our careers in the years to come.

Recommendations & Riffs

  • ⚡ Embedding learning in the flow of work

  • 🙏 Why tradition isn’t irrational

  • 🧠 Personality-laundering schemes

  • 🤩 Prestige in the recruiting process

  • 🌓 Linkedin’s Alternate Universe

Nine Trends That Will Shape Our Careers in 2021

To say 2020 has been a year of unprecedented change is an understatement. But few domains have been altered as drastically as the world of work.

For this year’s final issue of The Jungle Gym, I asked nine readers who have expertise in the future of work to weigh in on the trends that they believe will shape our careers in the coming years.

1. Living Online

Erik Torenberg, Co-Founder of Village Global & OnDeck

Historians will look back on 2020 as the year we moved our lives onto the internet.

In the coming decade, career success will depend much less on your physical location than where you spend time online. That means that getting into the right group chats and online communities has never been more important.

To be sure, IRL interaction will always matter. People will still meet for coffee, work together on whiteboards, and attend live conferences. But these modes of interaction will no longer be the only way people form relationships. 

In this new reality, where you live will no longer determine your fate. Particularly as more companies permanently transition to remote work, people from all over the world will get the chance to join fast-growing companies and network with other talented individuals.

Living on the internet will be the great equalizer. 

2. Global Hiring

Alberto Arenaza, Co-Founder of Transcend Network

From language barriers to illegible foreign credentials and esoteric local regulations, it’s no wonder most hiring happens at a local level. 

But as work continues to go remote in 2021, hiring will go global.

Whether companies like it or not, they will need to support employees traveling and living around the world. Naturally, these workers will refer candidates in the countries they visit, and companies will want to take advantage of these talent pipelines. 

HR departments will not need to bear the burden alone. Startups will emerge to make navigating global talent management. These new companies will help companies source and evaluate candidates, serve workers standardized compensation and benefits packages, and enable global educational credentials.

I look forward to the day when organizational cultures take precedence over national cultures for companies building their teams.

3. On-demand talent

Janine Leger, On-demand Talent Lead at Deloitte

This past year catalyzed a wave of interest in on-demand freelance talent.

While hiring freelancers is not new, the turmoil of the past year has made this model much more attractive. As a result of market shifts and cost-cutting measures, 3 out of 4 companies have skill gaps that are limiting their service levels and/or business growth.

Combine that with high turnover costs and long wait times to fill roles, and it’s no wonder this talent acquisition method is gaining popularity.

Modern freelance marketplaces allow companies to hire freelance experts much faster than traditional methods. Rather than having to wait months, managers can use talent marketplaces to get help in a matter of hours.

In the coming years, I expect on-demand talent will be an increasingly popular channel for filling open positions.

4. Liquid Employment

Packy McCormick, Author & Founder of Not Boring

Maybe because I’m a full-time newsletter writer and don’t work for a company anymore, but I can’t shake the idea that careers will become a lot more fluid in the years to come.

Pre-COVID, showing up to the same office every day made it hard to work for a second employer. But when another job is just a Slack workspace away, it becomes much easier to work multiple part-time jobs.

This flexibility will significantly increase the opportunity cost of choosing an exclusive employer. Every decision to spend four years vesting at one company will mean shutting off hundreds of other opportunities.

Investors would never choose to invest in just one company; the risk is too concentrated. Instead, they build portfolios. Over time, workers will invest their time in a similar way. 

Currently, liquid employment is largely impractical for workers and employers alike. But the same thing could have been said about remote work at one point. Spreading risk over a few companies makes sense for employees. That means that the companies that want an edge to hire the best people for a given role will eventually adopt it.

5. Employer Leverage

Taylor Stockton, COO of FutureFit AI and Co-Founder of Pathway Ventures

There’s a big risk that the economic events caused by the pandemic will cause an enduring shock to the balance of power between companies and workers. Unfortunately, this seems unlikely to tip in favor of workers.

Though this balance has historically fluctuated, in recent years, the leverage that companies have over workers has been growing as the influence of unions fades and outsourcing becomes easier.

When we look at the economic trends accelerated by COVID, there are some worrisome signs for labor. A recent McKinsey survey showed that since the pandemic, 67% of companies are accelerating the adoption of automation technology (fewer jobs), 70% of companies are hiring more independent contractors (fewer benefits), and two times as many companies plan to adopt remote work after the pandemic than before its arrival (more potential for outsourcing).

The pendulum of leverage seems to be swinging even further towards companies, especially for workers in vulnerable groups. Without further intervention, we could see existing socioeconomic and racial inequalities get much worse in the years to come.

6. Action Management

Liz Fosslien, Head of Content at Humu and author of No Hard Feelings

COVID forced organizations across every industry to make historic changes. The pandemic also rendered every one of their expensive, complex action plans useless.

As the pace of change continues to accelerate, leaders need a better approach to planning. That’s where Action Management comes in. Action Management isn't about building a meticulous 5-year forecast for an unpredictable future. It's about empowering employees to build the habits and skills that will allow them to quickly respond to changes in the environment. 

Instead of rigid plans coming top-down through department heads, companies will increasingly focus on building cultural structures that encourage employees to run experiments, flag problems, and teach colleagues what they know. 

In the coming years, the most successful leaders will be those who can empower their people with the skills and mindsets needed to deliver exceptional work in any scenario.

7. Wellness Culture

Carrie Bevis, Managing Director, Communities & Partnerships at Institute for Corporate Productivity (i4cp) and Connected Commons

Over the past year, organizations across every industry have started thinking about how to promote employee well-being.

Traditionally, the responsibility for an employee’s wellness fell on their manager. However, with the stressors of working from home, many managers are ill-equipped to give their direct reports the support they need.

In the year ahead, companies will drive employee wellness through structures and activities at the cultural level like:

  • No-meeting days 

  • Slack-free lunch hours

  • Virtual walking meetings (as a much-needed reprieve from video calls)

  • Team meditation/mindfulness sessions before meetings

Instituting programs like these can help create a culture of well-being for all.

8. Community Learning

Mercedes Bent, Partner at Lightspeed Venture Partners

After spending the year cut off from our broader social networks, people are hungry for community. As a result, I expect we’ll see several ed-tech companies try to leverage the power of social learning to drive better education and business outcomes. 

For example, imagine: 

  • Masterclass with a robust small-group learning community built on top of it

  • Duolingo leveraging live cohort-based messaging

  • Udemy matching learners who are studying the same topic

Some versions of social learning will emphasize the motivational power of bonding learners who are on a shared path, while others will promote learners teaching one another. Companies that manage to pull this off are likely to drive better learning and financial outcomes.

9. Live-Streaming Work 

Tom Critchlow, Freelance Strategy Consultant

In our age of remote work, it’s harder for knowledge workers to learn from one another. Whereas once it was easy to observe co-workers navigate problems by peering over their shoulders or jamming on a whiteboard, now their work has been rendered invisible.

This diminishing ability to witness work impacts junior workers the most. As they get less exposure to functional experts, they lose out on learning and networking opportunities.

What will emerge to fill this gap? One answer is Twitch. Ben Pieratt, a brand designer, launched Pre-Brand, a rapid branding service that mostly happens in Figma, live-streamed over Twitch. Increasingly these kinds of “working in public” experiences will create better visibility of knowledge work. 

Next year, I hope to see more managers live-streaming themselves triaging email or building decks. If this becomes standard practice, it will offer much-needed learning opportunities for the next generation of knowledge workers.

What trend do you think will shape our careers in the coming years? If you’ve got one to share, drop it in the comments.

Leave a comment

Recommendations & Riffs

Embedded Education

10-minute read from Tina He

We live in an age of abundant learning content. From how-to videos on YouTube to online Teachable courses, it’s never been easier to find quality educational content. Yet, few of us would say learning is seamless.

The question is– if access to content isn’t limiting our ability to learn, what is the biggest barrier?

I’d argue the answer is motivation. To summon up the drive to learn, we need to face off against Silicon Valley’s brightest designers, marketers, and product thinkers who have been pouring effort into making gaming, social media, and streaming video content as addicting as humanly possible. How can we possibly fight back?

Embedded education provides one answer. By integrating learning into tasks that learners are already driven to accomplish, it becomes much easier to overcome the motivation challenges.

At the moment, embedded education content is mostly used to promote feature usage within products. But there’s an opportunity to both deepen the kind of learning companies offer in these contexts and expand it to other arenas.

🙏 In Praise of the Gods

13-minute read from Simon Sarris

Years ago, a career counselor assigned me an exercise to help me define my values. On the table in front of me, he spread out 50 cards displaying words like honesty, family, and creativity. My job was to identify the ones that resonated and separate them from those that didn’t. Since all of the words sounded good, it was a relief when I came across a card I could quickly discard. It read tradition.

I’ve always imagined myself to be a “smart person” who arrives at opinions through reason based on scientific evidence. For much of my life, I viewed those who prioritize tradition as backward religious types, incapable of thinking for themselves. However, as I’ve grown older, I’ve come to view tradition and those who adhere to it quite differently.

Far from being a crutch for the irrational, I now see tradition as a value for those who are smart enough to realize how little we humans are capable of knowing. When confronted with the true extent of our own ignorance, the only rational response is to draw lessons from what has worked in the past.

It is said that traditions are answers to enduring questions, and so dispensing with them because we do not understand them (or "see the point of them") is an unfortunate way to squander this inheritance.

🧠 Torturing Geniuses

7-minute read from Agnes Callard

As a kid, I often wished I had a missing limb. It wasn’t that I wanted to deal with the challenges that come with the condition. Rather, I craved the sympathy and understanding that is often afforded to people who are grappling with hardship.

You see, I was a weird kid. For the majority of my childhood years, I wasn’t great at holding on to friends. Although I went to an all-boys school, I found it hard to connect with other boys. My inability to make friends caused me to act in ways that only made it harder to get what I wanted.

In the article, Callard refers to genius as “a personality-laundering scheme” that allows the geniuses to get away with bad behavior. Looking back, this scheme is exactly what I hoped to gain through my aspirational missing limb. 

But, as the author points out, creating a world where your faults are tolerated won’t cure your loneliness. “Real connection requires ethical community, and ethical community requires shared rules—not the exemption from them.”

Ultimately, I’m glad I kept my limbs. Of course, for the functionality. But also so that I didn’t have an excuse for my personality deficits. Instead, I was forced to confront them, and have a happier life because of it.

🤩 Prestige in the US Today

6-minute read from Robin Hanson

Contrary to popular belief, most hiring managers aren’t trying to pick the best candidate for the job. They’re looking to hire whoever will protect them from looking foolish. While these goals have a good deal of overlap, there are situations where they diverge. 

For example, while a Harvard degree may not improve a candidate’s job performance, it does provide a face-saving excuse for the manager if the new hire doesn’t work out in the role. “How could I possibly have known a Harvard grad wouldn’t be able to handle it?”

This, in part, is what makes prestige so important in the hiring process. It de-risks the candidate so the manager can prevent potential embarrassment. As the saying goes, “no one ever got fired for buying IBM.” The same holds for hiring Harvard.

🔮 Linkedin’s Alternative Universe

11-minute read from Fadeke Adegbuyi

While Twitter may be the most rage-inducing social network, Linkedin takes the cake when it comes to inducing cringe.

The fascinating mystery is whether Linkedin encourages normal people to act cringey, or if it gives naturally cringey people a space to fully express themselves?

Either way, read the whole thing—lots of laughs.

Jungle Gym Deconstructed

One of my goals for The Jungle Gym this year was to make the contents of older issues more accessible for new readers.

In service of that, I’ve overhalling the community hub and turned it into a library of links from previous issues of the newsletter.

I’m calling it “The Jungle Gym Deconstructed.”

If you get a chance to poke around, I’d love to hear what you think in the comments.

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