The Future of Work: Age of the Chrysalis

Coachabl
7 min readMar 22, 2020

Workforce Cocooning, a Multiplex of Transitions (and AI Acceptance) and Remote Ranging

We are entering a fascinating/horrifying stage of being which includes distancing, remoting and transitioning — akin to a new Age of the Chrysalis in the workplace. This is the future of work.

Sweatpants’ fabricators and video conferencing devs of the world rejoice…

However, this is more than a new WFH (or WTF) pandemic paradigm shift, this new and constant shifting will normalize “workforce cocooning.”

Between all of one’s job shifts, workers will acclimate to this cocooning, virtually metamorphosizing themselves into their next roles with multiple tenures and transition periods in between.

Predating COVID-19, many have already posited that remote is the future of work. Remote work or telecommuting is up 159% since 2005.

What if this sudden and ongoing rush to remoteness grows based on:

  1. Traditional employment tenures are reducing and doing so at higher magnitudes and frequencies;
  2. Automation or AI drives an aggressive need for reskilling (reskilling of jobs which currently is neither well funded nor widely available) at faster cycles and with more acceptance;
  3. That the gig economy is creating more independence, spreading skills and related remoteness which will also be disrupted repeatedly; and,
  4. Younger demos will be open and accepting of these more constant shifts, being “chrysalis-ready” for change and ranging opportunities.

Change has always been good, but will these more persistent transitions create a workable metamorphosis in our lives?

To begin with a personal use case: I’m not quite sure if I’m a serial entrepreneur or a serial executive, and I don’t think it’s just me.

It’s a lot of us, transitioning, more often than we think.

I’ve had a blend of both serial entrepreneurship and executive tenures — head of digital at three studios, founder of four businesses (two strategy agencies, one accelerator and one human-centric AI coaching startup in Coachabl), Chief Developer Officer and US CEO at two big tech startups (fintech and AI-based IoT with over $150 million raised between the two) and now working across M&E and PE sectors with a powerhouse transformation company. That’s ten businesses…

I’ve also mentored over 75 startup CEOs across many of these endeavors, everything from how to break into Media & Entertainment to how to transform your company to staying relevant in the Age of Information (aka Data), Automation (AI/ML) and whatever disrupts next.

Likely I’m a serial entrepreneurial executive (a “SEE”) with multiple transitions that provide me with a rich diversity of experiences. That, I tell myself, is the positive spin. However, average tenures are shrinking as we gig, side hustle and solopreneur into new futures.

With today’s standard work tenure being roughly four years for the middle-aged according to the Labor Bureau, and Millennials clocking in discounted or 50% reduced two-year tenures with assuming half the comp and benefits to boot (much like the two-year tenures at most big tech firms such as Google, Apple, Netflix, etc. without the signing bonuses and RSUs), are we looking at a multiplex of tenures?

A diverse portfolio of experiences (creating range) is becoming the new normal and perhaps a better way to succeed, according to David Epstein in his book, Range: Why Generalists Triumph in a Specialized World. Having range allows you to find a steady focus and discipline once you have experienced or sampled many pursuits.

Case in point, look at Disney’s new CEO, Bob Chapek, who ranged (aka transitioned) across the studio leading multiple business units, allowing him to specialize yet understand the overall cohesion of the brand and its consumers.

On front two, automation is set to remove 800 million jobs by 2030 according to McKinsey’s 2017 report. With data inflation and/or in expanding Moore’s law, let’s put that at one billion jobs, conservatively.

If “AI is the new electricity” of the 21st century, as Andrew Ng said, then we are in for an interesting century or start of the Fourth Industrial Revolution or Industry 4.0.

Anything repeatable will be automated; anyone able to work across roles in a more collaborative way will evolve less impacted. Hemant Taneja in his powerful Unscaled book writes that as humans “learn to collaborate with AI-driven machines [that we will further] unleash human potential.”

However, we’re woefully unprepared. With faster cycles of AI, we’re looking at large swaths of blue and white-collar roles becoming less relevant in major metros. Large spans of time (or tenure) spent may be akin to data gathering; once a role is sufficiently understood, can it be automated and added to the AI pile?

Automation affects many sectors: QSR (quick service restaurants with robotic cooks and kiosk “super-size oriented” order-takers) to logistics (trucks, taxis, Ubers), but also flows heavily into white-collar: accounting, legal, finance, research, sales, HR and other repeatable, process-oriented roles.

Areas currently protected by AI are creativity, collaboration and problem-solving — all areas which seem driven by diversity, experiences and range.

Per Forbes’ interview with Box’s Chief Product Officer, “Intelligence is the next frontier of the enterprise.” He adds though that 500 million white-collar jobs may be at stake. No one is safe but the net job growth in reskilled jobs may be a salvation of sorts. However, outside of companies like Coursera and universities like MIT providing new training and education, plus Bezos dropping $700 million to ‘upskill’ his workforce, there’s not a lot of retraining available, much less government-funded aid.

Will a new class of solopreneurs, e.g., those that leave corporations to start solo businesses (usually remotely), ride out this transition?

With the income gap shrinking between traditional and gig workers, we start to see its attraction for Millennials, Gen Z (born 1995–2009) and Gen Alpha (2010–2024).

However, with more risk in transitory gig work comes, of course, more chance for upheaval. Independent workers contributed $1.3 trillion to the US economy in 2018. As that number rises, it will certainly not be a stable ride.

I highly recommend Brad Stone’s Upstarts’ book with Uber’s former CEO’s infamous prediction, ‘The minute your [self-driving] car becomes real, I can take the dude out of the front seat […] I call that margin expansion.”

So, hypothetically, when Uber, Lyft and other gig workforces get fuller automated, we would experience additional transitions, moving a percentage of the 162 million gig workers (an already dated 2016 number from McKinsey) into their next role.

One agency creative and serial startup founder whose IRL business narrowly missed the pandemic refers to the “uncaging” of this talent caught in corporate cages:

“[Traditional companies are] too invested in old ways of capturing and at times ‘caging’ their talent as office-bound employees, and they’re the ones hardest [hit] as they try to adapt to a new remote work reality.” — Ryan Gill, Communo CEO.

This metaphorical uncaging sounds very similar to the metamorphosis of the chrysalis…

Finally, Millennials and younger age demos may be the most vulnerable but also most adaptable to this tide of automation.

With “75% of millennial-age managers say[ing] job-hopping has helped to advance their careers,” according to an Akumina survey, expect more fluidity to provide more growth and protection.

Millennials likely see Uber’s ‘margin expansion,’ which butterflies out to market expansion, tenure expansion and community (work, transport, education, entertainment and overall living) expansion. Upending these standards seems the new norm.

As we step into a Millennial-led society in 2030, we can likely expect a very different work currency: “The forty-hour work week may be challenged, along with the currency of higher education, [aka] the 120-credit degree.”

Millennials' acceptance of a diversity of experiences will enable them to navigate freely and go solo more easily in a shared economy.

A new employment model seems at play here.

We’ve gone from the “twenty-year gold watch” corporate gig to the 4.2-year current tenure to potentially a 4-day work week (assuming we all WFH anyway) to shorter 1–2-year solopreneur-influenced tenures to in-between gig work— all broken up by a myriad of transitions between each role.

So, traditional tenure > transition/cocoon/chrysalis > startup tenure > chrysalis > solopreneur > chrysalis > gig worker, repeating again and again and again…

The quick math: a 25-year-old worker retiring at age 70 in 2065 can potentially expect to mileage >20 multiples of two-year tenures:

25-years-old x 22.5 tenures (x 2 years) = 70 or retirement
35-years-old x 17.5 tenures (x 2) = retirement
45-years-old x 12.5 tenures (x 2) = retirement
55-years-old x 7.5 tenures (x 2) = retirement

Add a little hiring ageism to the above and tenures may actually multiply faster in the post-40 workforce. If we include transition timing between tenures, which could include solopreneurships and gig work, expect 3–6 months to 2–3 years of additional buffering.

Quicker tenure turns, automation leading to a more transformative workforce, remote career metamorphoses more readily accepted by younger generations, and solopreneurship are rising.

Who will help navigate these chrysalides? If COVID-19 has created an emergency chrysalis for the world — which it has, how will we come out of this? Humanity will need a reboot following a global pandemic. Country by country resurgences will require rapid transformations and acceptance.

I believe that we will learn to accept and traverse these workplace and life metamorphoses with assistance. New agile, human-centric AI, like Coachabl, will help us accept uncertain change, transformation and automation, an entirely new multiplex of transitions, and the new Age of the Chrysalis.

Author: Adrian Sexton, Coachabl CEO
Coachabl > Connecting Great Minds
Coachabl is a scalable coaching platform with human-centric AI.

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