The “everything” career — is this the future?

Welcome to the very first (!) edition of Monday Mornings. This publication explores the new world of work beyond the 9-5, diving into the shift toward mass entrepreneurialism through in-depth analysis and interviews with the builders, thinkers, and leaders shaping it. Whether you're a future-of-work expert or simply curious, this newsletter unpacks the good, the bad, and the ugly of this transition. Together, we'll navigate what this means for individuals, businesses, and society. You can learn more about Monday Mornings and what to expect here.

Monthly Briefings will include the following segments: In a nutshell, Get informed, Trailblazers, A final word (from me) and some Monday Marvels and Moanings this month.

Please consider sharing Monday Mornings with a friend or colleague who might enjoy it!

Happy Monday, folks!

In this month’s briefing, we’re digging deep into ‘Portfolio Careers’ and will be covering:

• The data proving they’re no longer niche

• The age-old pay gap issue

• The Trailblazers to watch in this space

Could the portfolio career path be the perfect post 9-5 solution, aka the “everything career”?

Portfolio careers are defined by those who seek out multiple, diverse streams of income (rather than one fixed job in a single sector), typically used when describing those in white collar, professional roles. Imagine: a Chief Marketing Officer resigns from their 9-5 and takes on a Fractional Marketing role for two days a week, a Board position with a promising startup, provides 1-1 mentoring to junior marketeers and occasionally guest lectures for a local University.

The portfolio career path is often seen as a natural ramp off for a senior professional ready to move away from the hustle and grind of their full time role, into more flexible, fluid arrangements.

The OECD predicts that by 2030, 50% of professionals will be building a portfolio career.

How close are we to that today, and, what nuances lie behind the data? Let’s dig in.

1/ The State of Portfolio Careers in 2024
(Source: TPC, February, 2024)

This article focuses on a poll conducted by The Portfolio Collective (TPC), a community of professionals curious about portfolio careers.

After polling 230 professionals, the survey pinpointed four key categories of portfolio careers: freelancers, multi-hyphenates, focused experts and side hustlers.

Survey respondents reported that 64% of their work came through referrals and networks. And, the biggest anxiety felt was around ‘generating a consistent income’.

The data also demonstrates a clear gender disparity in terms of pay, which is discouraging. The lower day rates are populated by more women, and higher day rates ($800+) by at least 50% more men than women. So a portfolio career does not solve the gender pay gap that is so often attributed to discriminatory HR/employment policies. Rather, the income gap is attributed to a self-reported imposter syndrome felt by those at the lower day rates. Whether or not these individuals simply have less experience than their high-earning counterparts, we cannot tell at least from these findings.

Portfolio careers are often cited as the antidote to the all encompassing 9-5, and, less risk than company-building. Yet this data infers some tropes and traits from the rest of the working world still persist — pay discrimination, income insecurity and ongoing hustle to land work.

2/ The Future of Work Revolution & The Rise of Portfolio Careers
(Source: The Portfolio Career Lab, November, 2024)

This podcast from The Portfolio Career Lab by Build with Brie, features Bradley Schurman, an author and consultant on demographic evolution.

Although it may not currently feel true — amidst high living costs and mass layoffs —he sees that the pendulum is swinging back in favour of employees regarding working relations. The dynamic of an aging population and shrinking talent pool will soon force employers to provide more flexibility (a top requirement from today’s workers). He sees the portfolio career path as one of those options — essentially the opportunity of working part time for an employer.

Many workers face increased pressure such as caregiving for both children and aging parents—making them increasingly in need of more flexibility. In addition, we are about to witness the great wealth transfer as a generation of Boomers pass on their assets to their Gen X and Millennial children, many of whom will become millionaires overnight. He asks how likely those newly minted millionaires will put up with a 40+ hour work week when they could attempt more flexible or entrepreneurial paths with their newfound financial security.

Though employers may seem resistant to flexibility, particularly with return-to-office mandates ongoing, Schurman warns that if they don’t adapt, “Who is going to do the work?!”

3/ McKinsey’s Women in the Workplace 2024 report 
(Source McKinsey, Sept 2024)

This report exploring “the path to parity” provides the largest study yet of women in corporate America. It reveals that for many women, their day-day-day experiences in the workplace are no different (or worse) than they were ten years ago.

Surveyed organisations revealed that gender and racial diversity were not priorities for their organisation; sharply observed by the statistics that the pipeline of women in corporate remains underrepresented (29% of C-suite roles, just 7% of which being women of colour). This pipeline problem starts early too, as more men than women get hired into entry level positions to begin with.

During the course of their working careers, women report the significant impact of micro-agressions, ageism, and being under rewarded and under recognised for their contributions.

The survey, however, revealed some areas where progress had been made: support in place for parents and caregivers (who are disproportionately likely to be women). Similarly, progress had been made in terms of workplace flexibility.

“If companies don’t take action, they risk losing not only their current women leaders but also the next generation,” the report states. This highlights that progress remains insufficient—and may explain why so many women are turning to portfolio careers.

The same McKinsey report from 2022 underscores this trend, describing it as a “Great Breakup” given the sheer volume of women leaving their roles.

• Squadra — Founded by Benoît Simeray, Squadra is reimagining the C-suite, by providing organisations with on-demand access to part-time executives.

• The Now Work — Founded by Laura Hunter and Hannah Phang, The Now Work have created portfolio career opportunities for sustainability & impact consultants, specifically.

• The Portfolio Career Club — Run by Julie Fedele, who set up TPCC to provide mentorship to women ready to ‘consciously uncouple from their corporate career’.

A Final Word (from me)

In its most idealised state, the portfolio career path could be imagined as high day rates, flexible hours, diversity of opportunities and leveraging the power of a personal brand to attract opportunities. This presents a lot of intrinsic appeal and a form of dipping ones toes into the world of entrepreneurship without the need to go ‘all in’ on one venture or income stream. It's a form of hedging bets.

When that is the case, this path presents a compelling alternative to the 9-5 especially, as we have discovered, especially for women and caregivers.

But I can’t help but notice — the prevalence of the portfolio career path in the public zeitgeist has coincided with a wake of mass layoffs by employers. It’s likely so many professionals are pursuing a portfolio career because they must string together whatever pieces of work they can. In other words, for them, it’s not voluntary, which worries me.

It’s not always the case that every form of income stream is a desirable one. The reality (at least for some people I’ve met) is there is often the “work that pays the bills that I don’t really want to do so I try to cap it to 2-3 days a week but sometimes it spills over” combined with “the work I want to do but can’t make financially viable in itself yet”.

That poses the question - is this a professional ménage à trois, juggling the steady partner that pays the bills with the alluring mistress of passion projects?

And, in other news this month…

👍Monday Marvels  

Farming collectives have provided land to business owners who want to build sustainable projects, with the tagline “no gear, all the ideas”. Thanks to Pitch Up! a total of 12000 acres of land has been offered as part of an innovative solution to share natural resources with business owners who can build a more sustainable future. Applications are open for the next round until 30th Nov.

👎 Monday Moaning

The inverse of quiet quitting is ‘silent firing’; a term we’re seeing used widely in the wake of the RTO (Return to Office) mandates — most publicly Amazon’s five day’s per week in the office by January policy. This piece by Fast Company covers the realities: RTO mandates are the best way to decrease employee retention while saving on redundancy payouts.

That’s a wrap for the very first edition of Monday Mornings! Stay tuned for the next one in two Mondays’ time, featuring a Q&A with the lead researcher at one of the largest talent platforms in the world.

I’d love to hear your thoughts on today’s topic. What else do you think should be considered? Share your opinions in the comments!

Monday Mornings is written and hosted by Ellen Donnelly, a writer, speaker, and coach focused on the future of work. She specialises in the shift towards mass entrepreneurialism, and supports founders navigating pivots in her private coaching practice, The Ask.