Meet the new boss, different to the old boss

How the AI-driven gigification of the labour market will play out

The three most harmful addictions are heroin, carbohydrates, and a monthly salary.
Nassim Nicholas Taleb, 2010

If you don't like how the table is set, turn over the table.
Frank Underwood, 2013

CEOs Start Saying the Quiet Part Out Loud: AI Will Wipe Out Jobs
Ford chief predicts AI will replace ‘literally half of all white-collar workers’…

In interviews, CEOs often hedge when asked about job losses, noting that innovation historically creates a range of new roles.

In private, though, CEOs have spent months whispering about how their businesses could likely be run with a fraction of the current staff. Technologies including automation software, AI and robots are being rolled out to make operations as lean and efficient as possible…

“I think it’s going to destroy way more jobs than the average person thinks,” James Reinhart, CEO of the online resale site ThredUp, said at an investor conference in June.

Corporate advisers say executives’ views on AI are changing almost weekly as leaders gain a better sense of what the technology can do—and as they watch their peers more aggressively change hiring plans or flatten corporate structures.
Chip Cutter, The Wall Street Journal, 2/7/2025

As I’ve observed every Friday morning for the last six months, many jobs are about to disappear.

I’d assumed what’s now being widely referred to as the ‘white-collar bloodbath’ wouldn’t kick off in earnest until 2026. However, I’m beginning to fear the large-scale bloodletting will commence during the second half of 2025. As has been widely noted, Microsoft has gotten the ball rolling by jettisoning over six per cent of its workforce in the first half of 2025.

But this isn’t yet another post about the robots taking your job, dear reader. It’s about how the labour market will likely function in the transitional period before stronger AI obviates the need for such a market.

The job is dead, long live the gig
If AI takes your job, you’re unlikely to be able to put your feet up and start collecting UBI. It’s also improbable you’ll be able to walk into another full-time employee role if every business in your industry is ‘right-sizing’ its workforce by 10/50/99.99 per cent.

What to do?

Many freshly retrenched workers will presumably enter the gig economy.

Some will do so in conventional ways, such as driving people, restaurant meals, or groceries around. (Software developer Shawn K wrote a viral Substack post a couple of months ago about supporting himself as a delivery driver while applying, unsuccessfully, for the best part of 1000 jobs.)

But many will attempt to leverage the skill set they’ve spent decades developing and attempt to earn money as consultants/contractors/fractionals. (Fractional CEOs, CFOs, COOs, CROs, CTOs and CPOs seem to be all the rage nowadays, which in itself could be an indicator of how AI is impacting the labour market and broader economy.)

I’m a long-time denizen of the gig economy and, as our American friends say, I have notes.

How tasks get completed in the digital age
Since the Industrial Revolution, it has been common for large businesses to employ large numbers of people on a full-time basis. Ford employed about 300,000 workers in the 1960s. In some instances, tens of thousands were employed at a single Ford site.

Due to the social, legal, and economic changes of recent decades, the traditional Monday-to-Friday, 9-to-5 job working for The Man is no longer the overwhelming norm. Nonetheless, it remains the default, especially for the Professional-Managerial Class (PMC). That's just how the life script plays out. You study hard to get into a good degree at a good university, so that you can get a good job at a good company, then set about climbing the greasy pole so you can enjoy a good lifestyle while in the workforce and a good retirement following that.

That is all now going away.

The difficulty grads are now having with the ‘get a good job at a good company’ part of the sequence suggests the second act of the PMCer life script has already been fed into the paper shredder.

None of which should come entirely as a surprise to white-collar workers. After all, they witnessed and often facilitated the offshoring and automation of blue-collar jobs in recent decades. Usually with precious little concern for the life scripts of those affected by their actions.

However, I imagine many PMCers will struggle mightily to accept that they are ultimately just as dispensable as a switchboard operator, typist, assembly line worker, Blockbuster franchisee, parking attendant, travel agent or, ahem, print media journalist. The more prestigious the university they attended and the position they once held, the more painful the struggle will be.

Having been there myself during the collapse of the legacy media, my advice is to work through the Kübler-Ross stages of grief as efficiently as possible. If you’re currently in Denial (‘There’s just no way AI could ever do my job!’), you can expect to cycle, not necessarily sequentially, through Anger, Bargaining and Depression before arriving, eventually, at Acceptance. (‘AI took my job, I’m not going to have the career and life I once envisioned, now I need to work out what to do next.’)

In the gig economy, you’re paid on results
Here’s how I envision things will unfold over the next couple of years. Businesses will automate any task that can be automated ASAP.

Public-sector employment could go either way. Governments will presumably be torn between wanting to cut labour costs and use the freed-up money for more generous welfare benefits, and being tempted to mop up some of the excess labour no longer employed in the private sector. Politics being what it is, there will be some combination of the two approaches. Deep cuts made in some areas (e.g. tax collection), while more people will be employed in others (e.g. aged care and healthcare).

That’s the bad news.

The good news is that, for the next few years at least, not everything can be automated away. To be clear, there will come a day when almost everything is automated away, but even the most wild-eyed AI boomers and doomers expect that to take a minimum of five years.

That means businesses and government departments will still require humans to perform tasks, and humans will still need or want to earn money by completing those tasks.

What won’t be happening so much in future is businesses collecting a bunch of tasks together and employing an individual for 40 hours a week to complete them. Instead, unautomatable tasks will be advertised on an online marketplace.

Such marketplaces have been proliferating since the GFC, with Uber, Airbnb and TaskRabbit all launching in 2008-2009. Depending on your location, occupation and interests, you’ve probably familiar with some of the larger task bazaars – Airtasker, Fiverr, Freelancer.com, Guru, Handy, PeoplePerHour, TaskRabbit, Toptal, Upwork.

Looking the part vs getting stuff done
It’s completely off-brand, but I must deliver at least some good news about the imminent gigification of the labour market.

The gig economy is outcome-based. You may protest that your current employee role is also outcome-based, and I’m sure it is to some extent, dear reader.

But there are university libraries full of studies proving that there are a plethora of factors that go into who gets hired, promoted and ‘let go’. To summarise: accent, age, class, clubbability, disability, ethnicity, gender, height and physical attractiveness.

In the more glamorous industries, looking the part, which is usually code for being young(ish) and hot, counts for a hell of a lot. Of course, that’s handy if you currently happen to be young(ish) and hot, but not so great once the ravages of age start to become apparent.

But a business or individual using an online marketplace to farm out a task doesn’t tend to care too much about the non-outcome-based stuff. They certainly care about it much less than a business or individual hiring a full-time employee who will be representing their brand.

Back in the day, I interviewed Airtasker co-founder Jonathan Lui. He was most keen to make the following point:

We’re not supplanting an existing labour force. What we’re doing is creating a whole new industry… there are a lot of people that find it difficult to access a conventional job. That can be because they’re an older person or an inexperienced, younger one. Airtasker provides a way for those people to be part of the workforce, to earn money and stay active.

When we started Airtasker it was mainly school and uni students but now we get a lot of semi-retired people. Another interesting development is that Airtasker isn’t just something people do on a moonlighting basis anymore. There are a lot of people now working full-time hours doing tasks and making a good living out of it.

Risk-averse company man vs gig-economy hustler
It would be a mistake to assume that the differences between giggers and employees run only skin deep.

As many have observed, the traits needed to rise in a corporate setting are different to those required to succeed as a (micro) entrepreneur.

If you want to ascend the greasy pole at a blue-chip company, it’s rarely helpful to be a risk-taking independent thinker willing to call it as you see it, regardless of who might be offended by your hot take.

In contrast, those who are self-employed are under far less pressure to be arse-covering team players. They are also well-placed to avoid most of the standard corporate bullshit, such as soul-crushing bureaucracy, performative busyness and, until very recently, DEI struggle sessions and cringe woke-washing.

The first shall be last, and the last shall be first
The thing about profound change is that it turns over the table. That’s usually mostly downside for those who have long benefited from the status quo, but largely upside for those who have failed to prosper under the ancien régime. If you’re good at what you do, but don’t quite look or act the part, you may do better as a gigger than you ever did as an employee.

Conversely, if you’re an office politician who has clawed your way up the org chart by practising the dark arts of credit-stealing, blame-shifting, reputation-destruction and image-management, you may find the gig economy inhospitable territory.

Be like the Chinese Farmer
There’s a Taoist parable, popularised in the West by colourful Zen Buddhist Alan Watts, that was originally entitled, ‘Who knows what’s good or bad?’ or ‘Maybe’. Nowadays, it’s usually known as the ‘Chinese Farmer’, ‘Zen Master’, ‘Lost Horse’ story. If you’ve watched Charlie Wilson’s War (2007), you may remember Gust Avrakotos, played by the late, great Philip Seymour Hoffman, sharing the story to warn the hawkish Democrat Charlie Wilson of the possible second-order consequences of his actions.

You can read the story here, but the tl;dr is that several things happen to a farmer. His neighbours oscillate between declaring these events to be good or bad fortune, while the even-keeled farmer just keeps replying, “Maybe”.

The moral of the story is that the world is a complicated place. Especially in the moment, it’s difficult to determine whether an event is ‘good’ or ‘bad’. Just to add to the complexity, supposedly ‘negative’ events have apparently ‘positive’ consequences and vice versa. (Buddhists refer to this as the Law of Dependent Origination, aka codependent arising.)

My fellow Substacker Evgeny Shadchnev recently penned a cautiously optimistic version of the ‘Maybe’ narrative for the AI age.

Demonstrating a serenity I’m struggling to attain, Shadchnev has also noted:

So many of us are trying to understand what’s going to happen with AI. Will it take our jobs? How will new grads learn? Why build something today if AI will be able to build it in 6 months? Will humans even survive AI?

I don’t have the answers, and I don’t suggest we ignore them. They matter. We must try to make sense of the exponential pace of AI even though we don’t have to keep up with it.

But we don’t need to lose sleep over the daily flood of AI news feeling like the world is falling apart. It might be, but in truth we don’t know.

In the face of accelerating change and deep uncertainty, the wisest response is the same as it was thousands of years ago:

‘Maybe.’