This transcript has been edited for clarity and checked against the available source transcript and recording. Filler, false starts, and obvious transcription errors have been corrected without changing the speaker’s meaning.
Lisa: All those boxes of success—the promotion, the work-life balance of training for an Olympic-distance triathlon—felt like a big mistake because I was in bed. I was bedridden.
Journey from Law to Radio#
James: I know your most recent podcast episode was about changing careers, and I’d love to hear about your experience. Going from law into radio, along with the other things you’ve done, is an interesting journey, so I’d love to dive into that.
Lisa: Do you want to hear how I went from law to radio, James?
James: Yes, I would love to hear that.
Lisa: I followed the path you follow when you come out of university. Everyone said I should try to get articles in a law firm, so I did. Then you blink, and seven years later you’re still working as a lawyer. I was really enjoying it, and it took me to London.
Picture London in the year 2000. We were all excited about the year 2000, the internet was suddenly booming, and in what is now called the internet bubble, a lot of money was being splashed around. I followed the money trail to London and started doing incredible transactions during the internet boom. Then came the bust, and the people funding this amazing movement lost their money. I stopped doing those huge transactions and, as a technology and e-commerce lawyer, was pulled into a different area: mergers and acquisitions.
They were still huge transactions, but the role of the technology lawyer was quite limited. I had to review, as part of due diligence, all the technology contracts for these big companies to make sure they were up to scratch. In those days, that involved sitting in an airless, windowless office for hours each day, reviewing piles and piles of documents.
I slowly died inside as I reviewed those contracts. Then a friend said, “Have you ever thought about volunteering for hospital radio?” The hospitals in London are so big that each one has a full-blown radio station. You volunteer, but you also get trained.
You do your flying time on other people’s shows. I did Monday-night bingo and read out calls such as “legs eleven” and “two little ducks, twenty-two.” Every Monday night, there I was. Once I had built up my hours, I received panel training. I would practise with my pens, pulling up the fader and talking, then pulling down the fader and turning it off.
Then I got my own show, Thursday Night Therapy with Lisa Leong, where I interviewed anyone I found interesting. I’d ask my friends, “Can you come and talk about this?” The show started gaining traction and grew an audience—maybe because it had a captive audience in a hospital. I fell in love with it and wondered, “How do I turn this into a career?”
I’m really curious about that part: once you’ve discovered that you love something, how do you turn it into a career? Looking back, I didn’t simply leap. I did a whole load of little things. As the consultant and coach Dorie Clark says, “Optimise for interesting.” Be very curious about this new thing.
I kept volunteering at different hospitals and radio stations, got myself onto other people’s shows in London, and did a lot of research. I listened to and analysed hours of radio, read books and did all those things. Then I decided to write letters, attach my hospital radio show as a demo and send them everywhere. I now know my strategy was “spray and pray.” It wasn’t very wise, and I received lots of rejection letters.
I got so many rejection letters, James. Although I can say that lightly now, it didn’t feel very good at the time. It was like asking, “Do you think there’s something here?” and having everyone say, “No, there’s nothing here.” I thought, “What was I thinking? I’ve got a bogan voice. I’m crap.” I turned on myself, lost a lot of confidence and thought, “I’ll just be a lawyer.”
The turning point came from empathy. I asked myself what life would be like for a program director making a big decision about whom to put on air: really busy, to be honest. I didn’t think they were listening to my demo tape, so perhaps I could do something else to have a conversation with them.
I found out that the program director of Liberty Radio—one of London’s biggest radio stations by footprint—also presented the weekend breakfast show by himself. I decided to cold-call him face-to-face. I took the first train out in cold, sleeting weather and arrived unannounced at the radio station. When I pressed the doorbell and he answered, I wondered whether I should run away. I was scared and thought, “Oh my God, he could call the police on me. This is ridiculous.”
Then I thought, “What’s the worst that can happen? He could call the police or reject me again. I’ve already been rejected, so let’s give this a go. What if it works?” I said, “Hi, my name is Lisa Leong. I’m a radio DJ. Can I make you a cup of coffee this morning?” Mind you, I was 30 years old, not 16. I was literally a corporate lawyer asking, “Can I make you a cup of coffee?” He buzzed me in, James.
I was meeting a man I’d never met before. He didn’t know who I was, but he let me in. I found the kitchen, made him a cup of coffee and, when he beckoned me into the studio, sat and watched him talk. I thought, “Wow, this is cool.” When he stopped talking and put on a song, he asked, “Okay, who are you? Tell me your story.” Suddenly, I was chatting with this guy. He was the dude, right?
The next week, I rang the doorbell again and said, “Hi, it’s Lisa Leong, the radio DJ, here to make your morning cup of coffee.” He let me in, and this time he put me on air with him. I chatted with Tom on the radio and returned every weekend until he was so sick of me that he gave me my own Sunday show. I brought in my friend Zoe Mack, and together we presented a show on Liberty Radio, which had London’s largest footprint. Getting that commercial radio experience was one of my biggest breaks.
He helped me put together a better demo tape, which got me into the Australian Film Television and Radio School after three rounds of interviews. I resigned from my law firm because I had learned that either 95 or 100 per cent of the school’s radio graduates got jobs. That was enough for me to say, “I’m going to do this. This is where I roll the dice. If I can get into AFTRS, I’ll resign.” I left my London job and came back to Australia. That set me on my radio path.
James: That’s a super-interesting story and a great example of initiative. It’s hard to turn up at an office like that. I think it’s quite bold.
Lisa: I think it takes micro acts of bravery, James, because there is a lot of inertia. Especially when you’re gaining experience, do you keep going or pivot? At those big career moments—what I call moments of truth—you need micro acts of bravery to change something, because inertia is strong. One day can simply roll into the next if you’re not purposeful or intentional.
Dealing with Pressures changing careers#
James: That’s really cool. I want to ask about the move in particular. You were working at the law firm and doing radio on the side. What did people say about that? They might have thought it strange that you were working at the firm while doing something seemingly random on a radio show. Leaving law entirely to pursue radio isn’t a classic move, either. Did you feel pressure to keep doing what you were doing? You had also invested so much time in law, and people often feel that they can’t do anything else because they’ve spent so long doing one thing. How did all of that flow through your mind at the time?
Lisa: In a way, James, I think it’s easier now. We talk about bringing our whole selves to work, and people understand that we don’t have to fit a very narrow idea of a worker. When we began working remotely and could see into people’s homes, we learned more about each person as a whole. Because of the internet and social media, I can also see that you have different hobbies or pastimes, or perhaps a side business or side hustle. All of that is part of you.
Back in the 1990s, I would say that we had a very professional persona. I was lucky to join a law firm that let me be myself, so I was all-singing, all-dancing, both as a casual worker and later when I did my articles. They absolutely knew that I was a lawyer, but I would also host or chair section meetings with a little boombox playing intro music. I would put out two lounge chairs and say, “Come and sit in my hot seat,” as if it were a television show.
They knew who I was and truly supported me. A nurturing environment can say, “Oh, that’s Lisa. There she is, singing to the clients again.” I never hid it. My law firm in London was supportive too. They said, “Wow, that’s unreal. You’re becoming a radio DJ. Nobody has ever resigned to become a radio DJ.” They were awesome.
If you’re honest and authentic, people can be your greatest supporters. I feel that work environments can now see that we all come in different shapes, sizes and modes, and that it’s all important.
The work for each individual is to see every day as lab day: an opportunity to learn more about yourself, particularly your superpowers and values. Your superpowers are the strengths unique to you. The more you play to them, the more helpful and happy you are at work, and the more likely you are to find flow and do your best work. That’s important for you and the organisation you belong to, because then you’ll be your best self and do unreal work.
Values are about understanding how and who you want to be in the world. I had a few mishaps with my health, so health became one of my most important values, above everything else. Others are connection, curiosity and freedom. I’m someone who needs to be quite free and autonomous. Whenever my life bumps up against a value, or I’m not playing to a superpower, bad things happen. You want to do the work of understanding yourself so that you can bring your best self to work. How does that resonate with you, James?
Creating your Values#
James: Definitely. I’ve recently been thinking about values and understanding what mine are. Have you ever followed a formal process—writing down what you value and thinking deeply about it—or have your values evolved until you realised what they were? What does that look like for you?
Lisa: A bit of both. It started with understanding when I felt aligned with an organisation and what was happening there. There is a specific exercise called the values elicitation process. Interestingly, because I recently wrote this book, there is a whole chapter on values.
We found one of the world’s experts, Greta Bradman, who happens to live in Melbourne. She’s a psychologist and a classically trained soprano, as well as a beautiful woman and soul. She has done a lot of meta-research bringing together all the research on values, and she shared her process with us and used it on us.
There is a list of values, because it’s quite hard to pull them out of the ether. She has roughly 50. You go through and mark the ones that jump out at you, then cross out the ones that are definitely not you. That gives you a good sense, although you’ll still have perhaps 20 or 30. From there, you whittle the list down to about five.
You also want to make each value unique to you. One of mine is curiosity, but what does that mean for me? I’m curious about people. Even when ideas come from a particular person, I’m interested in what drove that person to go deeper into those ideas. For me, it’s all about people.
That’s the values process. It’s worthwhile doing formally, but your values might also change over time. Hedonism was one of mine when I was about 20. I was thinking, “Follow the fun. Where’s the fun?” That was fine; I don’t regret it. Freedom has always been there, too. I’ve travelled a lot.
James: That’s interesting. Once you’ve mapped out your values, making decisions can become easier. Moving from law to radio, for example, might be easier once you know what you consider important and can map that onto what you do day to day.
Lisa: Would you like another exercise, James?
James: Of course.
Lisa: Another useful one to keep up your sleeve and do periodically is something I came up with in 2000, when I was wondering what to do next. I thought I had invented it and called it the happiness graph. I’ve since discovered that it’s a well-known exercise called the lifeline exercise; in the book, we call it the life flow exercise.
Imagine a graph with horizontal and vertical axes. The vertical axis represents subjective levels of happiness or a sense of “yay.” The horizontal axis represents time. You go back as far as you can remember, then move forward to today, mapping the highs and lows—the peaks and troughs—of your life.
You might remember an amazing moment in childhood, which is a peak. Perhaps your first year at university wasn’t great, which is a trough. You draw this subjective graph of highs and lows. For every peak, ask what made it a peak experience: who surrounded you, what you were doing and what the environment was like. For each trough, ask what caused it, what you were doing and whom you were with.
Then step back and look for trends. What made those experiences peaks? You can use that insight to build more consistent peaks intentionally. Troughs happen in life and you can’t always plan to avoid them; life ebbs and flows. But instead of blindly and accidentally hitting the same trough every time, learn from it. Every day is lab day, and you don’t repeat an experiment when you know it will have a negative result and fail.
For example, a peak experience for me was in 1999. One of the banks—your bank, actually—was creating an amazing division. We were essentially creating internet banking, and I was asked to go on secondment as the division’s lead and only lawyer. It was such a peak experience: diverse, creative people coming together to create something no one had created before. I was in heaven.
I had been working long hours at the law firm. At five o’clock, everyone came to my desk and asked, “What are you doing?” I said, “I’m working,” and they said, “Stop working. Let’s go to the pub.” We went to the pub and had the best time together. I was valued for the quality of my work, not the quantity. That was a learning in itself. The team was full of the best and most varied people: financiers, advertisers, marketers and project managers. I loved it.
That was a peak. For a trough, remember the airless, windowless office where I was effectively by myself. There is a theme: creating new things with other people was a peak; being by myself was a trough.
This is where the exercise becomes useful. I moved into radio, which involved curiosity and communication—unreal. Then I got an amazing capital-city commercial-radio job that everybody wanted. I was like a Z-list celebrity in this place, seemingly having it all. Yet I would do six-hour stints on air, come out and cry. Looking back, I asked, “Why am I so unhappy?” I was spending six hours by myself in an airless, windowless office, talking to myself with very little interactivity. Of course, there are no other human beings around when you present weekend breakfast for six hours.
I thought, “I’ve made a terrible mistake,” and applied to the ABC, where you work with producers and interview guests who come into the studio. I needed the objectivity to see that the problem wasn’t the industry; it was the environment.
James: That’s really interesting.
Lisa: So there you go: the life flow.
James: That’s a good exercise. I’ll have to go away and do those things. We’ve spoken about your book a little already, and I’d love to dive into it more.
Biggest Learning from the book#
James: What has been your biggest learning from the book, the podcast or the show of the same name? You’ve been doing it for a while now, so what have been the biggest learnings from the whole endeavour?
Lisa: We had been producing the podcast—which is also broadcast on Radio National as this working life—for a while. We always set out to ask with curiosity: why do we work the way we do? How might we work differently? How might we be more human at work? Those questions underpinned much of what we did, James.
Before COVID, we would ask those questions about topics such as remote working. There was always a mix of answers, but the gist was usually, “It’ll never work,” or, “That’s just the way it is. Why question it?” During COVID, remote working became a huge global experiment. We found that we could do it, although each approach has pros and cons that we’re still learning about. We’re now more willing to ask why we work the way we do, how we might work differently and how we can become more human at work.
Suddenly, these questions gained a kind of zeitgeisty traction, and we were all in it together. I call us a squad of explorers, because nobody is the expert. You have some data, James, and it differs from my data points, but together we can piece together what’s happening. That completely ignites my value of curiosity.
People were really along for the ride with This Working Life, both the podcast and broadcast. It was helpful because I think we were asking the right questions for people at the right time. It was super-rewarding, exciting and humbling.
Then I received a LinkedIn message from Arwen Summers at Hardie Grant asking, “Have you ever thought about a book?” Until then, I’d been talking to a publisher friend about whether there was a book in This Working Life, but before COVID the idea hadn’t quite formed.
Arwen asked the question at the right time. I thought there was a book because I was beginning to receive emails from people who didn’t know what to do about their careers. Some had been in the same job for 20 years; others were starting out and didn’t know how to make choices in such a crazy, chaotic environment.
The book formed around the question: how do you navigate your career in uncertain times? Careers are no longer linear. You don’t simply lock in, bunker down and go deeper and deeper into your expertise.
Remember the lesson from my peaks: don’t go alone. “Lisa Leong, don’t sit by yourself in an airless, windowless office.” I had luckily been collaborating with the wonderful ABC journo and digital editor Monique Ross, and I’d noticed that she was an amazing writer. I cheekily asked her one day, “Mon, have you ever thought about writing a book? You seem to love writing. Would you like to write one with me?” She said yes.
Collaborating with Mon was the most delightful thing on the planet, and we also worked with Arwen, our editor. We even created a soundtrack for the book. We got to work with a musician, Little Green, as well as her manager, and my husband made a video clip because we released an LP for the book. Isn’t that crazy? We started collecting people until everyone involved in the book became part of our squad of explorers.
Another learning was not to become obsessed with the output. You can fixate on what the finished product will be, but I said to Mon, “Let’s enjoy this and find joy in every moment.” Even the writing was joyous. We came up with ideas together and got them down. When something didn’t work, we approached it with curiosity: “That chapter failed. Let’s try again.” It was fine for me. You might need to interview Mon to see whether she also enjoyed the process.
James: The interrogation can take place in separate rooms.
Lisa: That’s right. “Lisa had a great time. Did you?” “No, it was terrible.”
James: That’s amazing. It certainly looks good, and although I haven’t read it yet, I definitely will. I think it’s relevant to people in my audience.
Lisa: Yay.
James: You’ve clearly put a lot of hard work and effort into it, and it seems to have been received well by everyone. Fantastic job. There it is, for those watching. Looking at the lessons in the book and on the podcast, are there any you think people underappreciate or undervalue, or that you wish more people were interested in?
Undervalued pieces from the book#
James: Is there an area that you think is cool and important but doesn’t get the reception it should?
Lisa: A funny one is that, when I started, my producer was intrigued by the fact that I’m a biohacker. Do you know that term, James?
James: I’ve heard about it. Is it when someone eats foreign green food, such as herbs from an Eastern culture?
Lisa: It’s using science and technology to hack your body. I did a lot of biohacking because, before COVID, I travelled long-haul frequently—to the US, or to New Zealand nearly once a week. Air travel takes it out of your body.
One example of biohacking is that I would use a device to shine light into my ears. There are photoreceptors in your brain that you can reach through the ear canal, and that would help me with jet lag. I would shine it when I was meant to be awake, for example.
A more extreme example is cryotherapy. You enter a chamber at about minus 170 degrees, as nude as possible, for roughly three minutes, and it kind of recharges your body. We produced a series in which I presented my biohacks to scientists, who assessed whether I was crazy and whether each one was worth doing. That was really fun.
We cover serious topics on the show, but we also have quite a lot of fun. That was one of the things I got to do on This Working Life.
Perhaps one of the best career topics we covered was portfolio careers. The concept helped me understand my own career. Instead of seeing one thing as your main career and everything else as a side hustle—at one stage, I had a consultancy while the ABC and This Working Life were side hustles—you see your career as a portfolio. Like an investor’s portfolio, it is diversified, but everything makes sense together.
At the moment, I present my ABC Sunday show and This Working Life on Radio National. I coach CEOs and executives, and facilitate off-sites for organisations. That could look like a hodgepodge and make me ask which part is my main job, which is my side hustle and who I am. A portfolio career is a helpful way to manage a whole career while seeing every part as additive and working together in harmony.
That’s the approach of Dorie Clark, whom I interviewed on the show. She introduced me to the term “portfolio career.” She actually came up with it because, early in her career, she was heavily reliant on one arm of it and then lost her job. She realised that was too many eggs in one basket.
Especially when you’re a freelancer, a diversified portfolio means that if something like COVID happens and you can no longer travel, you might have other aspects of your career to help you survive. That happened to me, so I had to consider what else I could do—or just take a mini-holiday for a little while.
James: That’s an interesting way to put it. I’ve heard the term before, but framing your activities as a portfolio sounds more comforting. You can see how the different parts intersect and how each gains value from the other things you’re doing at the same time.
Lisa: I think it’s important to see that relationship rather than thinking the different parts are destructive or in tension. My two ABC radio shows are an example. One is a live show broadcast on ABC Radio Melbourne on Sundays from 10 to 12. The other, This Working Life, is a highly produced weekly show on Radio National.
Rather than being in tension with This Working Life, my live broadcasting helps me present it more conversationally and listen better. For me, it’s all additive. Working in corporate environments also helps with This Working Life because I’m with real people in the real world—it’s like being in the wilderness of work. When I coach executives, I can understand what people are thinking and feeling and what the current zeitgeist is. Often, on This Working Life, I can say, “This is happening in the world of work. Let’s do our take on it. We’ve got to do this show.”
A Failure that ended up being a success#
James: I like that a lot. Has there been a failure or another time when something didn’t go to plan and it felt as though the world was crashing down, but it later worked out for the best?
Lisa: I’ve got so many. I seem to trip up a lot, James, so I’m always learning.
One that might be relevant to you came when I was doing really well in a client-relationship and business-development role. I kept being promoted, which was exciting, until I was offered an amazing role that I couldn’t say no to: leading business development in Asia for a large organisation. I thought, “How sexy and fun is that?”
My husband, my daughter—who was four or five at the time—and I moved to Hong Kong. Because I covered all of Asia, I flew around a lot, gallivanting across the region. I had an amazing, cross-cultural team of 18, and we were trying to do something special.
I was extremely busy. My calendar and inbox were full, and I had lots of responsibility. I was absolutely loving what I thought was a high-powered role. Then I thought, “Work-life balance? I’ll train for an Olympic-distance triathlon.” I was running, swimming, cycling and working. I didn’t feel stressed, but I was waking at three in the morning with a lot on my mind. I would work for hours, take a little nap, then work for the rest of the day while flying around.
I went on holiday with friends and, unsurprisingly, my body gave out. When you’ve spent too long running on adrenaline, all that adrenaline seeps away on holiday and your body says, “Actually, I’m stuffed.” Bang: I got shingles. I had no idea what it was; I thought shingles was a medieval disease.
It’s a bad, rashy thing, but mine became complicated and caused secondary nerve damage called postherpetic neuralgia. My GP said, “Whatever you do, don’t Google postherpetic neuralgia.” I went home and Googled it.
I found horror stories about people who never went back to work—never—because nerve damage causes searing pain. I was on seven different painkillers. I couldn’t hug my daughter or my husband. I would simply cry and think, “Oh my God, I’ve stuffed up.” All those boxes of success—the promotion, the work-life balance of training for an Olympic-distance triathlon—felt like a big mistake because I was in bed. I was bedridden.
I eventually recovered. A friend suggested meditation, which I’d previously dismissed by asking why I would do that. But I followed Jon Kabat-Zinn’s program, mindfulness-based stress reduction. It’s from a Massachusetts hospital and is scientifically tested, I guess.
It was hard, but it really helped me manage pain and stress and gain a greater sense of presence. My brother described one result by saying, “You’re so much nicer now.” It also helped me be with another person, truly present and focused.
That was when I became a biohacker and a health-first person, James. I would have been quite old by then—maybe 40. It took me a while; I’m a slow learner. Actually, I might have been in my thirties. I have no sense of time, so let’s say 30-something.
I realised that health is so important. If you don’t have health, you’ve got nothing. Being bedridden isn’t good. I began asking what putting health first looked like for me, which led to my morning routine and many of my other practices. Although freedom is one of my values, I’m still disciplined. Structure gives you the right amount of freedom.
James: I don’t know whether you’re familiar with Jocko Willink, but he has a saying—
Lisa: The commando, right?
James: That’s right. He’s like a commando. I’ve forgotten the saying.
Lisa: I don’t have it tattooed on my chest like he does.
James: One day we’ll get there.
Lisa’s Advice for Graduates#
James: I’ve got one more question, Lisa, about careers and young people. I ask every guest on the show: if someone were graduating from university and heading into the world, what advice would you give them, knowing what you know now and what you’ve been through?
Lisa: Never listen to someone who gives you advice without asking questions first. That’s my advice. Isn’t that a head spin?
The other piece is: don’t put too much pressure on yourself. I think you find the right path, whatever road you take at a fork. There is a lot of pressure to make the right decision, but it all comes out in the wash at the end of the day.
If you make a misstep and accept a position you absolutely hate, tick: well done. You’ve learned what you don’t want next time. Take the pressure off; you’re okay. If every day is lab day, you’ll be fine.
James: That’s a good attitude: every day is lab day. Experiment, move closer to the things that give you energy—the highs you mentioned—and steer away from the lows where possible. If people want to learn more about you and connect, where should they go?
Lisa: The best place is LinkedIn. I think I’m listed as Lisa S. Leong. It’s a good place for anyone with a career, so I’d encourage you to create a basic LinkedIn page if you haven’t already. You can also follow me on Instagram as Lisa S. Leong. Those are the best places to connect with me and write to me.
James: Thanks so much for coming on, Lisa. It’s been a very entertaining and insightful chat.
Lisa: Thank you, James.
Outro#
James: Thanks for listening to this episode. I hope you enjoyed it as much as I did. If you want my takeaways—the things I learned from this episode—please go to Graduate Theory.com/subscribe, where you can get my takeaways and all the information about each episode straight to your inbox.
Thanks so much for listening again today, and we’re looking forward to seeing you next week.