"This is the biggest labour story of our time, but no one talks about it" — Jeff Wald

Welcome to Monday Mornings! A publication which dives into the new world of work beyond the 9-5, exploring the rise of mass entrepreneurialism. Through sharp analysis and interviews with the builders, thinkers, and leaders driving this shift, we’ll unpack what a post 9-5 world means for individuals, businesses, and society.

This edition is a Q&A Interview, where an expert guest offers their take on the future of work, along with our signature Monday Marvels and Monday Moanings segment.

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Happy Monday, folks!

In this week’s Q&A Interview I’m talking to Jeff Wald; serial entrepreneur, author and creator of the “Future of Work” prize.

Some of you may be aware of Jeff as author of The End of Jobs (which I was very excited to dig into with him). Others of you may familiar with him as founder of Work Market, acquired in 2018 by HR services leader ADP, Work Market enables organisations to better manage their contractors.

Today, Jeff is working on his sixth startup also in the HR space, Boomerang Intelligence. He has also challenged experts to predict their version of the future of work and will select the winner with the closest prediction in 2040, awarding them a $10m prize. 

I asked Jeff:

• Is it the ‘end of jobs’ as we know it, or is this just rhetoric?

• What employment trends has he witnessed while building HR tech companies?

• Is AI taking more of these jobs?

Enjoy!

Q: Jeff, you named your book “The End of Jobs.” But ironically, you have been vocal about these workforce shifts not being as drastic as many claim?

A: The book predicts the end of the traditional 9-to-5 model: one office, one manager. That type of job has been “dead” for a while; it just doesn’t know it yet. Today, we don’t stop working at 5 p.m. and forget about our jobs until the next day. However, while freelance and on-demand work has grown, it’s happening slowly. There’s no sudden, massive structural shift—it’s incremental, not revolutionary.

There has been a decline in traditional employment, but it is very slow. It is very small, it will continue over time, but the idea that suddenly there's going to be some huge, structural shift just has no basis.

In the U.S., the tax code differentiates between full-time traditional “W2 workers” and on-demand workers, who lack many of the same protections as W2 workers.

On-demand work means you’re not tied to one employer. It’s a category that has certainly grown, but not nearly as much as people claim. In 2010, everyone would say that by 2020, 50% of the labour force would be on-demand (aka contingent workers). Then, as we approached 2020, people said that it would be 50% by 2030.

Quite frankly, people see a statistic that the on-demand economy grew by 7% last year and keep making the same mistake of extrapolation. You don’t just ‘do that math out’ that’s not how the world works. So let’s all be careful and look at history and at data and talk to those making labour force decisions to get a logical view of how the labour market may evolve.

Q: So it might not be as big of a shift as was predicted, but has there still not still been a sizable shift in the number of freelancers?

A: What matters is how did it rise in comparison to the full-time economy? There has been a share shift of about 3% over a decade... It doesn't matter what percent the on-demand economy rose each year.

We always kind of project these trends into the future to be kind of sensationalised more than the past. People say that the on-demand workforce is taking over the full-time workforce because it plays into a narrative that companies are taking advantage of workers and that we are always in a worse and worse employment situation. But statistically, by every measure, work is better today.

We tend to romanticise work and how it was before, and be incredibly fearful of how employment is going to be in the future. But for the last 200 years, work has steadily, slowly gotten better: we've worked fewer hours for a higher standard of living.

Q: What career experiences led you to this conclusion? And what made you care enough about this topic to write a book (and talk to me today)?

A: It’s mainly from the hard-fought experience of building Work Market, a company that helped businesses engage freelance workers efficiently and compliantly.

During that time, I attended countless HR conferences where the narrative was always the same: “Everything is going on-demand.” I’d ask, “Can you point me to all of these companies transitioning their labour forces?” Because I had spoken to hundreds of them and not a single one (and I mean zero) where they transitioned their labour force to on-demand.

Of course, I'm an entrepreneur, and we chase revenue. So if somebody wants to potentially buy from me, then I'm jumping on a plane. I flew all over this country… all over the world… because companies claimed they were considering transitioning thousands of workers to freelance. And then they would say, yeah, no, we can't actually do it. Whether it was regulatory hurdles, customer concerns, competitive dynamics, or internal business process reasons, the transition never materialised.

The companies we worked with were those that had already transitioned decades ago. Our software brought compliance and efficiency for them. But the idea that a wave of businesses were shifting to on-demand labour… just wasn’t true.

I flew to one company in Texas three times because they kept dangling the prospect of transitioning thousands of workers. But after a while, it was clear that it wasn’t going to happen. Fool me once, shame on you. Fool me twice—well, I kept coming back a few more times before catching on!

Q: Surely all this hype about the move towards on-demand work isn’t just hype. Are there roles or industries driving this more than others?

A: After many conversations with clients, potential clients, and consulting firms, we developed what we call a “labour equation.” It consists of about ten variables that determine whether a company will engage a freelancer or opt for a full-time, part-time, or temporary worker. These variables vary in importance depending on the industry, role, and geography but they are the same core ten variables.

There are all these different factors such as intellectual property concerns, customer interactions, and regulatory issues. For example, if your customers keep seeing a new person every time they interact with your company, it can damage trust in your brand. Or if freelancers are working on sensitive IP, the risks might outweigh cost savings.

People always think it’s about cost. They say, “Freelancers are cheaper because you don’t pay them benefits.” But that is not the case. Yes, all else being equal, companies will choose the less expensive option. They are profit-maximising entities, so all things being equal, if they can, they will. But everything else needs to be equal.

Another example is the rise in ‘1099 forms’ (these are used to report freelancer income in the U.S.). While the number of 1099s has increased, it’s only meaningful in relation to the number of W2 forms filed for full-time workers. But say 1099s in a period grew by 5% but then W2s grew by 6% in that same period then the on-demand economy would have actually shrunk in relative terms.

In many cases, we’re just formalising what was previously informal. For example, take dog walking: before apps like Wag, many dog walkers were paid in cash “under the table.” Now, apps track these transactions, leading to more 1099s being filed. But this isn’t a structural shift in the labour force—it’s the formalisation of a grey-market transaction.

Q: We’ve talked a lot about employers and their preferences for workers. What about the workers themselves? From my vantage point at least, there is a growing trend of people wanting to work for themselves.

A: There’s definitely a certain type of person who thrives on the freedom and flexibility of working for themselves. It’s more of a psychographic trait—a mindset—than something tied to demographics. That mindset has grown, and the services supporting self-employment have made it more viable than ever.

In the U.S., for example, the Affordable Care Act (Obamacare) was a game-changer. It gave people access to health insurance without relying on their employers, removing one of the biggest barriers to striking out on their own.

Fifteen years ago, when you said “freelancer,” people heard “unemployed.” They’d respond with something like, “Oh, you’re a freelancer? That’s adorable.” Today, when you say “freelancer,” the first association is “entrepreneur.” It’s a massive undertone shift in perception—and one that reflects broader cultural changes.

But to me the more interesting conversation to be had is the rise of the on-demand services which have reshaped how people interact with the workforce. Consumers are saying, “I don’t need to own a car. I’ll just use ride-sharing apps. I don’t want to go to the store—I’ll get it delivered. I don’t even want to walk my dog—I’ll hire someone to do it.” These shifts in consumer behaviour have created structural changes in how work is done and what workers are willing to do.

Q: How about the rise of AI, how does that change your perspective on the future of the job market?

A: AI and robotics will certainly mean that we will lose jobs—there’s no question about that. But the idea that massive structural declines are coming tomorrow is just crazy. It’s not going to happen.

Every time a new technology emerges, jobs are destroyed in some areas, but they’re also created in others. New fields arise, existing ones expand, and historically, this process has actually increased the total number of jobs.

I believe that the rate of adoption and productivity increase with AI is greater than the rate of job destruction capable of, so my statement is that we will have no net job losses.

When it comes to AI and job loss, it also has to be viewed against demographic trends. Labour forces in developed countries—Germany, Japan, France, China, and soon the United States—are shrinking. For the first time in history, we’re seeing a decline in the labour force in these regions.

This is the biggest labour story of our time, but no one talks about it because it’s not as sensational as AI. Yet it’s the key variable in the future of work. As labour forces shrink, the balance between jobs needed and jobs wanted becomes crucial. As long as society maintains that balance—where the amount of work matches the workforce—we can focus on increasing standards of living instead of panicking about job losses.

AI will bring some disruption, of course. But this idea that AI will lead to mass unemployment flies in the face of 200 years of history, where new technologies consistently have created more opportunities than they have destroyed.

To find out more about Jeff’s work, his book The End of Jobs and the future of work prize visit Jeff’s website and follow him over on LinkedIn.

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

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And, in other news this month…

👍Monday Marvels 

The UK’s £125bn creative sector could gain greater protections from tech companies who have been taking creator’s work to train their AI models. Greater protections for artists and creators could come as a result of the proposal for the ‘right to personality’, which is currently under government review.

👎 Monday Moanings

Some unemployed Americans are now spending over a year looking for a new job. A recent study of 100,000 job seekers found that 44% had been out of work for more than 12 months, with 64% stating that the job market is worse than it was six months ago.

Thanks again to Jeff Wald for joining us in today’s Q&A Interview. Stay tuned for the next Briefing post in two weeks’ time, all about the skills we most need for the future.

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 career pivots in her private coaching practice, The Ask.