Work is the new playlist

How the job bundle is breaking apart and why we need new skills and systems to replace it.

Buying the full album

For most of the 20th century, a job wasn’t just a job but the organizing institution of modern life.

When you sign an employment contract, you don’t just get a salary. You get a daily routine, colleagues, healthcare, a pension plan, credibility at the bank and a whole identity neatly wrapped inside the package of employment. Stability and a safety net included. The job is the gateway to income, status, security and belonging.

Companies like Google took this to the extreme where your entire life conveniently comes with the job: sushi chefs, gym, laundry service, a doctor on site, education, childcare, maybe a car. You hand all your life to the company. You could spend 24 hours on campus and never need to leave. It is less a job and more a lifestyle subscription. And once you are in, good luck walking away - that comfort was designed to be sticky.

The traditional job is less like a single track you chose to play and more like buying the full album at the record store. Even if you only liked two songs, you had to pay for the entire thing because that was the only way to listen.

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Breaking up the album

The traditional job bundle is unraveling and not because of one single factor but a perfect storm. Technology cracked it open with automation and AI stripping away tasks that used to require teams, while global platforms connect workers and employers from anywhere in the world. Suddenly, being tied to one office, one company or one country no longer feels inevitable.

Rishad Tobaccowala describes it well in his book Rethinking Work¹. The rise of marketplaces from Fiveer to Upwork, from Shopify to Etsy, from Uber to Amazon have allowed individuals to access opportunities and offer services and products in a scaled global way from their mobile devices. Add the acceleration of work from anywhere made possible by distributed work and now the removal of barriers to knowledge or talent (agents, freelance, fractionalized employees) and the biggest shift which few are prepared for is underway.²

Economics accelerated the shift. Wages stagnated while the cost of living rose. Companies normalized layoffs and outsourcing, transferring risk from the institution to the individual. ‘Jobs for life’ turned into short-term contracts, gig work and project-based roles.

And culture plays a role too. Gen Z especially, but not only, resists traditional work structures and is unwilling to grind away in rigid hierarchies for a gold watch at retirement. They want flexibility in where, when and how they work. They want jobs that fit their beliefs, protect their mental health and deliver more than a paycheck. They strive for meaning, community and social purpose. The old bundle promised stability and status but for younger generations, putting all your eggs in one employer’s basket began to feel less safe, not more. Diversifying income streams came to look like the smarter hedge.

And of course there was COVID, the great accelerator. Overnight, millions were pushed onto Zoom and the office was revealed as less a temple of productivity than a habit of culture. People glimpsed an alternative - working without commutes, rigid hours or bosses peering over their shoulders - and many didn’t want to go back.

Put together, these forces shattered the monopoly of the traditional job and opened up alternative models. The CD case is starting to crack at the hinges and once you’ve gotten a taste of picking your own tracks, it’s hard to go back.

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Creating your own playlist

One full-time job rarely satisfies all of our reasons for working. So what if we stopped trying to find a single perfect job that contains everything we want and broke it all up into smaller pieces that make up our own versions of work?

Instead of squeezing everyone into a one-size-fits-all model for work, what if people were free to rebundle the parts that matter to them? That’s where the portfolio career comes in as one potential alternative model.

A portfolio career is defined as having several part-time jobs or multiple income streams rather than one full-time gig. It involves pursuing multiple passions, interests and types of work.

Mine looks something like this: a fractional role two days a week that pays the bills. Creative impact projects such as my Substack that lets me explore ideas that matter to me. AI tools as my invisible backstage crew. Investments for long-term stability. A schedule shaped around my energy, not the other way around.

And the social layer? I decoupled that from work a while ago. During four years of fully remote startup life, I had to figure it out myself. Co-working spaces became my substitute for office lunches, friends replaced colleagues and when I moved to Lisbon, I built a whole new social circle from scratch. For the first time, neither a company nor a university played any role in it. Instead, it came through hobbies, yoga, random café conversations and communities built around my interests. Third places and online networks are starting to take over what the office once provided.

In the process, I’ve remixed pieces of the old job bundle into something that feels more personal, more resilient and a lot more fulfilling.

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Building the sound system

Of course, here’s the catch: our systems are still built for the traditional job. Taxes, healthcare, pensions, mortgages, they all work best if you’re traditionally employed. The world is set up for albums, not playlists.

I don’t blame anyone for not jumping in yet. It’s still early stage, and early stage means friction - the kind only early adopters are willing to tolerate.

The system needs to catch up

On the system level, Lawrence Lundy-Bryan has some excellent thoughts. In his opinion, the opportunity for regulators isn’t to protect jobs at all costs, but to build systems that empower people directly.

“What’s needed is a replacement for the job’s bundle. Not necessarily in a single institution, but as a network of systems. Decentralised if you like. Or composable if you want. Or basically, just services, if you are a normal person. Portable benefits that follow individuals across projects. Legal wrappers that spin up and down as collaborations form. Early signs are visible. In Belgium, SMart acts as an employment proxy for freelancers, smoothing income and handling taxes. In the U.S., Opolis offers health insurance and payroll infrastructure to independent workers. Stripe Atlas and Shopify reduce the cost and complexity of running micro-enterprises.”³

Being in charge of your own career

These are glimpses of a new infrastructure but we’re not there yet. In the future governments might offer portable benefits tied to the individual not to the job. More startups may emerge as one-stop shops for solopreneurs. And multinationals might lean further into hiring fractionalized employees instead of full-timers.

You’ve probably noticed by now: I’m all about agency and shaping your own future. If you want to stay ahead, waiting for institutions or companies to catch up isn’t enough. The playlist model is already here, whether they’re ready or not, which means the responsibility and the opportunity, is ours.

For the first time, individuals have the tools to build their own bundles. Decentralization is moving power out of firms and into the hands of people. But this independence requires agency.

Entrepreneurial skills are becoming survival skills. Even if you never planned to found a startup, you can learn how to shape your own bundle: navigate multiple roles, manage your own safety net, build networks outside a single employer. Just as important are the meta-skills such as learning how to learn, staying curious, reinventing yourself and building a reputation beyond any one company. A category of one at best, connecting different skills, knowledge and interests.

If the job bundle is coming apart, then - as Lawrence argues - we need to tell a positive story about what replaces it. A future where individuals can remix their own playlists of work without losing the security that once came bundled in the album.

What shaped my thinking.

1. Rethinking Work: Seismic Changes in the Where, When, and Why - Rishad Tobaccowala

2. Strategic Reset - Rishad Tobaccowala

3. Unbundling the job - Lawrence Lundy-Bryan