What happens when the job that defined you disappears? And what does it mean to rethink your relationship with work when the world of work itself is being reinvented?

In this conversation, Andrea Levinson sits down with Tim Duggan to explore identity, meaning and what it actually takes to lead well in a moment of profound change. Tim shares the inside story of building Junkee Media to 65 staff and facing near-bankruptcy, what he learned driving around Australia for six months after exiting the business, and why the skills we’ve been calling “soft” may be the only ones that truly matter now.

Five Things That Stayed With Me

1. The MAP framework

Tim’s antidote to identity fragility: know your Meaning (what gives your work and life purpose), your Anchors (personal values), and your Priorities (how you want to spend your time). These three things supersede any job title, and they’re the only things that hold when the world changes around you.

2. The 20% rule

Research from a UK hospital found that doctors who spent about 20% of their time on tasks they found meaningful had the lowest levels of burnout. You don’t need everything to feel meaningful. You just need a fifth of it.

3. The one-legged stool

If your entire identity sits on a single work pillar, any external force can tip you. Tim lived this when he left Junkee. The answer isn’t to care less about your work, it’s to build other pillars alongside it. If one shakes, you have somewhere to lean while you rebuild.

4. The great irony of AI

The skills we’ve spent decades calling “soft” - leadership, empathy, creativity, the ability to conflict well - are the ones that can’t be replicated. AI is not making them less relevant. It’s making their value undeniable.

5. 4,320 work days

If you’re 45 today and retiring at 63, you show up to work 4,320 more times between now and then. That number has a way of clarifying whether “fine” is actually acceptable.

Work feeling ‘fine’? Use the Leadership energy reset to gain clarity and a specific path forward.

Quotes Worth Holding

“The great irony of artificial intelligence is that it’s going to show the importance of human intelligence. — Tim Duggan”

“The line between success and failure is so, so thin. — Tim Duggan”

“The problem with identity is that it can also use you. — Tim Duggan”

“We’ve taken the snow globe and shaken it. But we haven’t put it back on the mantelpiece yet. — Andrea Levinson”

“Feelings are for feeling.”

What We Explored

0:00 Introduction

1:48 Tim’s leadership edge: near-bankruptcy at Junkee Media

6:10 When your work identity becomes a one-legged stool

12:01 The MAP framework: Meaning, Anchors and Priorities

22:00 The future of work is personal, messy and already here

29:34 Who wants to live “fine” for 4,320 more work days?

31:11 The 20% rule: how much meaning you actually need

35:08 The loneliness epidemic and what work replaced

40:03 The case for experiments — at work and in life

43:25 AI and the great irony of human intelligence

53:06 Final thoughts: every CEO is just a human figuring it out

About Tim Duggan

Tim Duggan is a journalist, author and leading voice on the future of work. He is the author of Work Backwards and Cult Status, and writes a weekly column for The Sydney Morning Herald and The Age. Tim was co-founder of Junkee Media, a digital media company he built to 65 staff before exiting in 2020. He now dives deep into the big, complicated questions facing leaders and workers - simplifying them for people trying to figure out where they stand in a rapidly changing world.

If this conversation resonated, explore more insights and resources at andrealevinson.com.au

Full Transcript

Lightly edited for readability. The full timestamped version is available on YouTube.

ANDREA: Welcome everybody to Leadership at the Edge, this conversation for April. Today we're joined by Tim Duggan and I'm really excited to get into this conversation. For those of you that don't know Tim, he's a journalist, author of Work Backwards, a leading voice on the future of work.

It feels like collectively and individually we are in a moment where we're rethinking our relationship with work — what it means, how we do it well, what we're willing to give to work, and what we want back in return. So we'll unpack some of that today.

For everyone listening, my invitation is really simple. Stay curious. Notice what resonates, what challenges you, maybe how what we talk through might apply to your world, your team, your leadership. Curiosity wins every time.

Now Tim — when have you found yourself up against the edge in your own leadership? What did that look like? How did you navigate it?

TIM: What a great first question. Most of us are thrown into leadership in the deep end — all of a sudden you have someone underneath you saying 'what do I do?' and you need to figure that out as you go. That happened as my co-founders and I built a media company over 15 years, which I then exited in 2020. We had about 65 staff at our peak. That's where my leadership was forged and we were up against the edge most days.

We had a significant moment when we discovered we were massively in debt and didn't realise it until it was almost too late. A co-founder, myself and our chair were knocked sideways by almost a million dollars in debt we had a few weeks to find, or the whole company was going into administration. That was so hard to deal with personally and professionally — and we had to basically hide it from our staff. We were in glass-walled offices and people could look in and see the look on our faces. Leadership is about having judgment calls around how much to share and what you share with people. The line between success and failure is so, so thin.

ANDREA: So thin. And also — you've survived the hardest day, right?

TIM: 100%. We were able to beg, borrow and steal money from anyone who would listen and found it within two weeks. Didn't go into administration, and continued building a really successful business.

ANDREA: It sounds like a very challenging and defining time. The higher the highs, the lower the lows. Building a tolerance for that I think can be really important. How did it feel navigating walking away from — or closing a chapter on — building that business, exiting and crafting something new? It's that path from point A to point B that unsettles people. Not knowing what it looks like or how to get there keeps us in mediocre, keeps us in fine, keeps us in meh.

TIM: Identity is one of those fascinating topics. All of us have a work identity that we carefully build — and then it can be taken away in a redundancy, in sickness, or by our own choice. My identity for years was 'Tim from Junkee.' When I left in 2020, I didn't realise how hard it was going to be to not have my identity tied up with my job. My husband and I jumped into a camper van, drove around the country for what was meant to be six weeks and ended up being six months. That's where I started to shed some of the identity.

I spent time reconnecting with what I loved before I got caught up in the whirlwind of running the business. For me that was writing — coating my thoughts into words, sharing things with people, teaching people. All the things I really loved doing when I was a music journalist in my early 20s. I reconnected with that, wrote Cult Status, then Work Backwards.

There's something really powerful in recognising that if we wrap everything about our identity into one pillar — it's like a stool with one leg. If you take that leg away, of course we're going to be very unstable. Whereas if we've got different identity pillars, if one shakes we can lean into the others while we're wayfinding and rebuilding.

Having your identity so deeply wound up in it was really motivating at the time. That's the allure of a strong identity. But the problem with identity is that it can also use you. Your identity can take over. And if you're not the one controlling when you're going to leave — which most of us don't have complete control over — a layoff can happen at any stage. That becomes really hard because you can have your identity ripped away before you're ready.

In Work Backwards I went into a simple acronym called MAP — Meaning, Anchors and Priorities. If you know what meaning you get from work and outside it, if you know what your anchors or personal values are, and if you know the order of your priorities — how you want to spend your time — that is way more important than any job title is ever going to be. That's what you can hold on to when the world changes around you.

ANDREA: I love MAP. A lot of the time we use the label of work identity as a substitute for what actually guides our priorities or what is meaningful to us, rather than doing the deep excavation. This discussion around AI is really bringing some of these things to the forefront — all of a sudden we do have more time. A report that would have taken four hours now takes four minutes. The question is what are we choosing to do with the rest of that three hours and 55 minutes? And that comes down to the MAP.

TIM: Exactly. And for busy, achievement-oriented people who've outsourced their sense of satisfaction to accolades from others, it can feel very confronting to sit still and do nothing.

ANDREA: A question in the chat from Jenny — about outplacement and the loss of identity. She's observed it has been more confronting for her male clients. Do you see a gender differential?

TIM: I think there are gender differentials in almost everything because of the way society has raised people. On a broad sense, traditionally the genders do have differences in this. Maybe it's a singular leg to the stool for men when it comes to work. Maybe there are a few more legs for women. I'm drawing a long bow there.

When people are laid off, the ability to process that emotionally and then actively move to the next stage is really different for everybody. It depends on personal situation, mental health, financial situation, where you are in your career, what your industry looks like.

ANDREA: I would 100% agree, and I love the call-out around emotionally processing that shift first and foremost. We can't just rush into the next thing even though we feel like that is the answer. There's so much opportunity in that moment to choose again. I'll never forget the phrase 'feelings are for feeling.' How often do we put a lid on it — pushing it down because we're anchored into the need to do, to get to the bottom of the inbox?

TIM: Totally. I think that's one of the biggest leadership lessons I've learned over 20 years — the need and the right and the privilege to process things emotionally before moving to the next stage. I have been guilty of rushing straight to action instead of allowing myself the space to process. Understanding how long it takes you is something I'm constantly aware of in all relationships.

ANDREA: Warren in the chat has suggested we've got an identity outside of work too.

TIM: A great call-out. When I talk about Meaning in the MAP acronym, there are two parts — what meaning you get from work, and what meaning you get outside work. Understanding both is really important. If you get all your meaning from work, you might have a great fulfilling job for a while, but that's not going to last forever. We are in fact well-rounded humans as opposed to robots designed just to do a job.

ANDREA: You mentioned so much is shifting in the world of work — AI, psychosocial risks, wellbeing at work. I feel like there's an opportunity for us to re-craft the way we relate to work. What's a very tactical, tangible next right step somebody can take?

TIM: The future of work is three things. Personal — because it's very different for you and me. Messy — because we're all going through this at the same time. And here right now. The simplest thing I often tell people is not to worry too much if you feel uncertainty and fear and apprehension — because every single person is going through this at the same time. No one is an expert in this technology. As soon as you make that mental switch from fear to 'we're all figuring this out together and I'm going to experiment and make mistakes' — it just changes your mindset.

ANDREA: I look around at the organisations and clients that I work with and it's like we've taken the snow globe and shaken it, but we haven't put it back on the mantelpiece yet. We keep picking it up and shaking it again.

TIM: I don't think we're ever going to put it back on the same shelf. I think we had a period of relative stability in workplaces from the 70s to the 2010s. Yet in the past seven years, how we work, where we work, and why we work have all changed dramatically. And I think the great irony of artificial intelligence is that it's going to show the importance of human intelligence.

ANDREA: I did some quick maths recently. If you are 45 today and retiring at 63, you show up to work 4,320 more times between now and then. I talk with so many people who've climbed this career Everest and it feels a bit 'meh' — but I guess this is it, right? Who wants to live fine for 4,320 more work days?

TIM: Amen. And there was a fascinating study for Work Backwards that looked at doctors in a UK hospital and their level of burnout. They were asked to measure which parts of their job they got meaning from and how long they spent on those areas. What they found was that doctors who spent about 20% of their time on tasks they found meaningful had the lowest levels of burnout. Less than 20% and burnout was high. At 20% it was low — and once they got over 20%, the level stayed about the same. You don't need to find every aspect of your job meaningful. As long as about a fifth of it is meaningful for you, you can live with the rest.

ANDREA: That feels much more realistic and achievable. And there's actually a tool called job crafting — figuring out which parts of your job give you meaning and doing more of those. Maybe it's not your paid job. Maybe 20% of your time is volunteering or a community piece.

TIM: I think the best one is people you work with. Can you find someone you consider a friend and enjoy working with? Then it doesn't matter if you're doing something you really dislike — if you're doing it with someone you enjoy the company of, that can make a huge difference.

ANDREA: And I think you wrote recently about the loneliness epidemic at work.

TIM: Yes. Up until 2020, almost all of us had a daily ritual from Monday to Friday. Even just going to that same coffee place, saying hello to Jenny as you walk past, making a coffee at 11am — all of that was ritual. And that was really important. I'm the biggest proponent of working from home — it has so many positives. But we need to talk about the negatives too. We are increasingly becoming more lonely.

When I published that story, I had dozens of messages from people saying 'thanks for talking about this.' Two very quick ways to deal with it: one — when you go into the office, what are you doing versus what you're doing at home? They should be very different things. Don't sit at your desk and type out emails in the office. Do that at home. When you're in the office, have that meeting, have creative collaborations, go out for lunches. Two — for workplaces: rethink how you're setting things up. Give people budget to go out for lunches. Make sure people come in on similar days.

ANDREA: That intentionality has so much potency. But it requires cognitive load. A lot of us have fallen into rhythms where we're saving brain calories rather than intentionally thinking about it. Perhaps there's an opportunity to craft a new structure and rhythm that supports us.

TIM: My favourite word in the workplace is 'experiments.' Giving someone the experiment framing means it can fail and that's okay. It has a limited time period. And by definition you should choose what you're measuring. I always tell people: if there's something you want to try — a four-day work week, working from home one day a week — go to your manager and say 'I would like to run an experiment.' Set it up for three months. Agree what you're testing. Most managers would at least consider it.

ANDREA: That experiment lens is so valuable. Impermanent. We're not saying I'm right and you're wrong. We're lowering the stakes. We're trying it on for size. And with that new data, we get to make much more informed choices.

TIM: Exactly. And I think about the purpose of a piece of work. If we think the purpose of a report is just to generate a report and send it to somebody, then maybe AI is the way to go. If we think the purpose is to build understanding, pressure-test an idea, build our mental model of something — then we approach that task differently. We need to know what we're solving for.

ANDREA: I have a new rule forming in my head — if someone expects me to spend time reading something, I expect them to have spent time creating it. AI-written books are never going to properly take off because we don't want to consume something entirely written by computers. When someone sends me a 40-page report and you know from the first line it was written by AI — why should I spend an hour reading it when you've spent a minute creating it?

TIM: The ultimate irony — someone writes three bullet points, creates a 40-page report, you ask AI to summarise it and you get three bullet points back. Just send me the bullet points in the first place. Communication is leadership. Communication is relationships. It's one thing that sets us apart as a human species. And if we're 20 and AI writes all of our emails and does our essays at university — we will never learn how to do it. That's going to be the biggest thing we need to keep our eye on.

ANDREA: This feels like a beautiful point to bring the conversation into land. You're talking about the human skills that are going to be the differentiators — the ability to connect, to build trust, to think critically, to be creative and innovate.

TIM: The great irony of artificial intelligence is that it's going to show the importance of human intelligence. Leadership, creativity, conflict management, empathy — skills we thought were 'soft.' Skills we thought weren't important. These are skills that cannot be replicated. That emotional intelligence of how you read the room, how you look someone in the eye and say 'I like you but I disagree vehemently with what you say' — all of that is so much more important. AI is showing us just how important they are. And if there are any skills we should be leaning into over the coming years, it's all of these human skills.

ANDREA: Tim, any final thoughts?

TIM: When we talk about leadership, we tend to forget the human side. Every CEO is just a human trying to figure it out. They might look ruthless or harsh on the surface. Yet underneath all of that, we're all the same. Every single leader — even the ones we put on pedestals — has the same fears, hopes and concerns as all of us. We're all figuring this out at the same time. That's such a freeing thought.

ANDREA: So freeing. And there's so much permission in that. Tim, thank you so much. Such a broad-ranging conversation. I think you've painted a really beautiful picture of a moment in time where so much is up for grabs in the way that we relate to work. We can do that individually, as leaders, as workplaces. But we need to see it as the opportunity that it is — an invitation to run some experiments. The more we lean into that, the more successful and more importantly the more fulfilled we will be.

TIM: 100%. Thank you so much.

ANDREA: For those of you who have joined us, really appreciate you being here. Have a beautiful rest of the day.