Unfinished Business Podcast Episode 4: How to Work Backwards and Build a Life Beyond Work
In Episode 4 of Unfinished Business, Anaita Sarkar speaks with Junkee Media co-founder and Work Backwards author Tim Duggan about the shift from founder to employee, the hidden operational load behind a growing business and his approach to designing work around the life you want. Tim explains why reclaimed time needs a purpose, how he protects his calendar and why working backwards is a gradual practice rather than an overnight reset.
Welcome to the fourth instalment of the Unfinished Business series. Unfinished Business explores the uncomfortable truths and behind-the-scenes realities of running a small business – the stuff nobody talks about.
As usual, we meet our regular host Anaita Sarkar, founder of Hero Packaging and Staje, and author of the book Sell Anything Online. In this first of three posts, Anaita speaks with Junkee Media co-founder and Work Backwards author Tim Duggan.
Their conversation covers the strange transition from founder to employee, the realities of managing a growing business, and Tim's "backwards" approach to building work around the life you want.
Part 2 of the blog series covers Reality Check, where real small business owners confess their failures and ask for guidance, while Part 3 covers the Growth Hotline, an in-person interview with an emerging founder who needs help expanding their business.
Tim Duggan talks Junkee Media and learning through failure
Anaita introduces Tim as someone who's done "a bazillion things", including writing three books. His latest, Work Backwards, focuses on designing work around the life you want to live. Tim is quick to point out that people remember success more than failure. For every success, he says, there were countless ventures that never worked out.
For Tim, it all started at age 23 when, as a music journalist, he co-founded a website with the publisher that eventually rebranded into Junkee Media.
“It was a big, thriving, hard, exciting and daunting business to run.”
Junkee grew over roughly 15 years, reaching around 65 employees. As digital media took off, the business rode the wave before selling an 85% stake to oOh! Media in 2016.
When the business you love becomes cash flow, legal and HR
Tim notes he found a big disconnect between what the outside view of running a small business involves, and what his actual day-to-day looked like. Most businesses start with something their founder genuinely cares about. As the business grows, that passion often takes a back seat to management duties – controlling cash flow, legal issues, and human resources.
When they eventually sold the company, Tim says that all the extra overhead became someone else’s problem, and he felt he had the headspace to focus.
“I could hand over my problems with people, finance and legal to teams who could help.”
It was at this point that Tim felt he could take stock of what he’d been through and what he’d learned along the way. With the extra help on hand and room to breathe, he started work on the manuscript that would eventually become his first book, Cult Status.
From founder to employee, then back to something new
Tim stayed on throughout the earn-out period because, somewhat unexpectedly, he enjoyed being an employee. The business still faced challenges, but there were specialist teams to handle problems that founders often manage themselves.
After a few years, Tim felt the itch to do something new. The success of his first book encouraged him to pursue writing more seriously, and he still receives messages from readers applying its ideas in their own businesses.
Working backwards
Guided by his experiences, Tim started writing Work Backwards as a way of sharing his philosophy of work and life, along with practical examples of how to reprioritise life over work in meaningful ways.
Tim says the starting point should be simple – decide who you want to be, how you want to spend your time and what kind of life you're trying to build. Then work out what it costs to make that life possible. Once you've done that, look at how work fits around it.
“Instead of automatically treating work as the most important thing, how can we reframe life as the most important thing?”
Rather than trying to live around work, Tim says that work should serve the life you want to lead, and while work is still important, it’s not the most important thing.
Anaita asks whether Tim actually lives the Work Backwards philosophy. He says he does 100%, but notes the book isn't just based on his own experience. He spoke to people from different backgrounds to understand what reprioritising work and life looks like in practice.
The three-day work week and fiercely protecting the calendar
Tim has worked a three-day week for the past five years but says it requires discipline. He limits meetings to a small window between 10am and 2pm, Monday to Wednesday, and treats exceptions as exactly that. The goal is to protect time for the things that matter outside work.
Anaita agrees, stating that his experience of having time to live life outside of work is the goal for herself and many other entrepreneurs.
"It is not about chilling on a beach. It is about having mental space."
She says that many founders – herself included – do not give themselves the breathing room they need to think about life. Instead, they support their teams during the day, do their own work after hours, and spend weekends thinking about what they should be doing next. Without the space to think about life, Anaita says that founders and small business owners find it hard to work backwards.
Freedom took 10 years, not one productivity hack
Tim agrees that it is a hard ask but asserts that a change in priorities of this magnitude does not happen overnight and requires a deliberate, deeply personal decision.
For Tim, that change took him 10 years to reach and involved trying – and failing – to sell a business he’d spent over a decade growing. Then, when it sold, going through the earn-out phase and beyond to gain the time and space needed to speak with other founders and investors. And when his dream of moving internationally seemed about to come true, COVID hit, putting the rest of it on hold.
Far from being an effortless switch, Tim's journey is really about creating more choice in how he spends his time.
Start small: reclaim 30 minutes and give it a purpose
Tim's advice is to start small: reclaim 30 minutes and use it intentionally. That might mean picking up the kids from school, going for a walk, meditating or pursuing a hobby. The activity itself matters less than consciously choosing something meaningful.
“If you want to hike, hike. If you want to spend time with the kids, do that. Whatever gives you meaning.”
Of course, ask any small business owner or founder what they might do with an extra half an hour and they might tell you they’d spend it working. But if every spare minute automatically gets absorbed by work, nothing really changes. Tim says that, instead of working on autopilot, it’s worth asking yourself what you’re working for. Then use the desire for that goal to reinforce your decision to condense your work hours, lock down your diary, or use AI to handle summaries.
The important Part, Tim asserts, is that you make the decision, then enforce it by giving the decision meaning.
Key takeaways for small business owners
The common thread through Tim's advice is simple: decide what matters, then build your work around it.
1. Define what a meaningful life looks like for you
It’s easy to say you want to spend less time working, but what do you want to do with your time? Make a clear statement of what you value – how you want to spend your time – then describe how you want to include those values in your day-to-day.
2. Design work to support your life
Once you know what matters, you can start working on the logistics. How much time will you need? How much will it cost? Does your current work environment support these needs? What changes can you make towards making them happen? Will 30 minutes less work be that big a deal?
3. Use boundaries intentionally
While it may not be possible for every founder or small business owner, Tim’s rule about limiting the time allowed in his calendar for meetings is an excellent example of how to use boundaries to bring about change in your work patterns. Set the expectation, enforce the boundary, and let it become normal over time.
4. Expect gradual change
Meaningful change takes time. Tim spent years adjusting his priorities before his work properly aligned with the life he wanted to build.
5. Give reclaimed time a purpose
It’s one thing to claim back 30 minutes of your workday. It’s another thing to then consciously spend it outside of work. Deciding what you’ll do with the time in advance – then sticking to it – helps reinforce your resolve, while slowly changing how you view your work/life balance.
Thanks for reading Part 1
That's it for Part 1 of our Episode 4 recap. Part 2 is here, and you can check out the full episodes here:
If you prefer to read your small business info, we also have the full episode transcript available here.
Anaita
Welcome back to Unfinished Business. I am your host, Anaita Sarkar, founder of Hero Packaging and Staje, and author of Sell Anything Online. Today we are joined by a man who has shaped the way a generation of Australians consumes media. He is the co-founder of Junkee Media and the author of Work Backwards. Please welcome Tim Duggan.
Tim
Thank you for having me.
Anaita
I feel like I said two things that you have done, but you have actually done a bazillion things, including being the author of Cult Status. And you are writing your fourth book at the moment?
Tim
My fourth. We normally talk about the things that work. We do not talk about the things that fail. There would probably be about 30 things you could list and say, “He founded this thing that failed.”
Anaita
For everyone listening, it is not just Work Backwards. Everyone would know you originally from Cult Status. Tell us where it started.
Tim
I was a journalist to start with, primarily a music journalist in my early twenties. Then, when I was about 23, I co-founded a website with some friends, without knowing much or thinking of it as a job or career. Over 15 years, that grew into Junkee Media. At its peak we had about 65 full-time staff, so it was a big, thriving, hard, exciting and daunting business to run.
Anaita
How long did it take to reach 65 employees?
Tim
It was gradual over 15 years. Within that 65, there were hundreds of people we had hired, fired or made redundant, and all the highs and lows of business. We rode the wave of digital media and Facebook, which at the time was the main way people consumed information. We sold the business in 2016.
When you start a business because you are interested in the topic, and then it grows, you can end up spending most of your time dealing with cash flow, legal and HR. When we sold to a company with about 1,000 staff, I could hand over my problems with people, finance and legal to teams who could help. For the first time I had some headspace, and I started writing Cult Status.
Anaita
Did it really help you?
Tim
It really did. We still had the problems, but all of a sudden I had help. Before that, it was me and my business partners fumbling our way through and using consultants where we could. I stayed for about four years through an earn-out, and then even longer, because I enjoyed going from being a founder to being an employee. It was a different experience.
Anaita
Did you?
Tim
For a couple of years. Then the itch happened again and I needed to do something different. Cult Status came out in 2020, and six years later I still receive messages almost every day, or certainly every week, from people saying they have applied something from the book to their business. I love seeing a new generation take something from it and apply it to everyday life.
Anaita
Then you transitioned to another style of book, Work Backwards. Do you actually live the Work Backwards life, and can you explain what that is?
Tim
One hundred per cent. Work Backwards is a way of thinking about work and how we prioritise what we do in life. Instead of automatically treating work as the most important thing, how can we reframe life as the most important thing? Start with what we want to do and who we want to be, then the money we need to do that, and then work. Work is still important, but it is not the most important thing in our lives.
I live by it. While writing the book, people would say, “Your life looks pretty nice. How do you do this?” I did not want the book to be only about me, so I spoke to 60 or 70 people, from bakers in Glasgow to founders, who were reprioritising the role work played in their lives.
I now work three days a week, and I have for the past five years. I control when people can put time in my calendar. Normally, I only let people book between about 10am and 2pm from Monday to Wednesday. It is not perfect. If I have a book deadline, I will work on a Friday. But I am fiercely protective of it. My husband and I spent three years living in Mallorca, and we both worked three days a week and spent the other four days living.
Anaita
You are goals to me and to so many founders and entrepreneurs. It is not about chilling on a beach. It is about having mental space. At the moment, many people work all day helping their team, do their own work at night and think about work all weekend. We do not have the freedom or space to think about life. I find it hard to work backwards.
Tim
It is really hard, and it does not happen overnight. It took me about 10 years to reach that stage. That meant deciding I wanted more freedom, speaking to co-founders and investors, trying to sell the business and failing, trying again successfully, going through the earn-out, then COVID stopping our plans to move overseas.
What I love and want is unique to me. I love hiking and diving, so I make time for those things. For somebody else, it might be picking up their child from school at 3pm. It might be reclaiming half an hour to meditate, or sleeping in. The concept is to start small. Ask, “How can I save half an hour today?”
The temptation, if you save half an hour, is to think you now have another half-hour to work. Instead, consciously ask what you are working for. If it is more time with family, and you save half an hour by using AI, having better meetings, condensing your work hours or controlling your diary, decide what you want to do with that time. If you want to hike, hike. If you want to spend time with the kids, do that. Whatever gives you meaning.
Anaita
It starts with deciding that is what you want to do.
Tim
Exactly. Most of us do not make that decision. We get caught in the swell of life, and before we know it, we are working 24/7.
Anaita
Now it is time for Reality Check, where we listen to real stories submitted by listeners about things that do not always go right when running a business.
Listener 1
I launched a new product last year on Instagram and bought a few thousand fake followers to make the account look more established. It backfired spectacularly. Now about 90 per cent of my community is bots from accounts posting crypto scams, and my engagement is about 0.01 per cent. I am basically talking to a digital brick wall. Please help me out.
Anaita
I do not mean to laugh in a bad way. We have all done these sorts of things and it never goes well.
Tim
I am laughing in a bad way. I have not done these things.
Anaita
You are a master of community engagement, so I can see why you would laugh. But as a small business, you sometimes feel you need to fake it until you make it. What are your thoughts?
Tim
The quality of your community does not need to be about quantity. I would rather have 1,000 people who were my exact audience than 10,000 who were not. I understand vanity metrics, but I would recommend that he start again.
Anaita
A new account?
Tim
Yes. It feels like this one is ruined. Aim for 100 people. When we talk about online numbers, they stop meaning anything. If you have 1,000 real people following you, you are talking to potential customers. Once you reach 100, aim for 200, then 500.
Anaita
People underestimate the value of starting again. You have made the mistake and learnt that the followers and engagement mean nothing. Creating a new account and fresh content can take you further than keeping an audience that does not engage.
If you were giving advice about going from zero to 100 followers, what would you say?
Tim
Figure out exactly who you are going for. At first, he was going for a number. Now he needs to go for a particular type of person. Put yourself in their shoes. What do they want to know? How can you help them? How can you create content that is valuable to them?
Anaita
I would also find people who already own my audience. I would ask to be on their podcast or find ways to give value to their audience. That gives you a starting point, and then you create content that resonates with the right type of person and addresses their problems. Leveraging other people’s audiences is one of the best ways to begin.
Something smells wrong when an account has 10,000 followers and no likes. That looks worse than an account with 1,000 followers and meaningful engagement.
I have been looking at business social accounts to understand what works. Many seem to have fake followers, and some appear to be paying for engagement, with the same number of likes on every post. Businesses may do it to look bigger or more successful. But those vanity metrics do not mean cash, customers, repeat loyal customers, brand ambassadors or real engagement. They only boost your ego.
Tim
I think they do matter, but not in the way people think. They matter because they distract you. They take your time and attention away from figuring out how to get leads and conversions. You end up chasing, “Congratulations, we reached 20,000 followers.” Who cares?
Anaita
We have one more Reality Check.
Listener 2
I am a founder who likes to be flexible with my team, but lately they have taken it too far. We recently had a 9am strategy meeting and I was the only person there. One was on the road, one forgot and I do not remember the other explanation. I want to be a good boss, but not a doormat. How can I give my team independence and flexibility while ensuring they come to meetings on time?
Anaita
This is made for you: future of work, leadership and workplace conflict. What would you tell him?
Tim
I hear him. We are living in a time when the line between what is acceptable and unacceptable is blurred. Six years ago, everyone would be in the office by a certain time. If you were not there by 8.30 or 9am, your manager would have a conversation with you. That was the social norm.
Now we have moved in the other direction. People work from home and the boundaries are more flexible, which can invite problems. Accountability can fall away. But you can have accountability and still have a flexible workplace.
This was a strategy meeting, not a regular weekly meeting someone happened to miss. It sounds important. The founder should have one-on-one conversations with everyone who was absent. Explain why it matters and the behaviour he noticed. Do not begin by judging or yelling. Ask each person to explain why they acted that way.
Once you listen, you can get to the real reason. They may not have realised it was important. There are many possible explanations. But unless you have honest, hard conversations with your team, nothing changes. He needs to put his big-boy pants on and have those awkward conversations. About 80 per cent of people will avoid conflict if given the chance, including me.
I have spent the past few years studying workplace conflict because I am writing a book about tension. One of the most interesting findings is that there is a single word I think is the most powerful in conflict.
Anaita
What is it?
Tim
“How”. Every time you incorporate “how” into a question, you invite the other person to solve the problem with you. Researchers call it forced empathy. In this situation, you might ask, “How am I meant to do my work if you do not arrive on time?” or “How do you think this sets an example for the other employees?” You invite the other person to understand the impact and help solve the problem.
Anaita
It is about asking the right questions with a curious mindset.
Tim
Yes. Some questions are leading because you already know the answer. “How” can create an open question.
Anaita
It is also how you say it. You cannot make it accusatory.
Tim
The intention matters. The only way to tighten loose boundaries is by asking questions and being clear. My new book is called Clear Intention, and it is about being clear in moments of tension.
Anaita
You heard it here first. When I started my first job at an accounting firm about 23 years ago, there were rules on rules. I was told off for certain clothes, being a minute late or saying certain things. We grew up in a much more black-and-white workplace. Now those people are managers and leaders, and we have to lead in a different way. It is hard.
Tim
It is more open. You need to be flexible while setting boundaries. People management is one of the hardest things. You can go through your entire career fumbling your way through it. We learn from mistakes and move with the times. Things are greyer now. Different generations are working together, and it is hard.
Anaita
You had 65 employees. If you could give one tip for creating a culture that benefits everyone, what would it be?
Tim
Most people think culture is set from the top by founders and CEOs. It is actually also set from the bottom up, because culture is how people behave. Leaders can say what they want the culture to be and must model it, but culture can be undone by people who do not agree with it or behave toxically. You need to be conscious of it.
You never reach a point where you can say, “Done. We have a good culture.” It is a living organism. It comes from the top, the bottom and the events you have. It can change in an instant, and you need to adapt as people’s behaviour and the world around them change.
Anaita
Leadership and people management are hard, but also incredibly rewarding. To the listener: have the difficult conversations. Difficult conversations, easy life.
Anaita
Now it is time for the Growth Hotline, where a real small business joins us to talk about where they are and where they want to go. Our guests are Lauren Barber and Elisha Mullins, the founders of NeedleCalm. They have created a medical adhesive pad designed to block pain signals for people with needle phobias. Welcome.
Lauren
Thank you.
Elisha
Thanks for having us.
Anaita
I am genuinely excited because this is so needed. Lauren, you are a registered nurse. Tell us how you came up with the product.
Lauren
I have been nursing for just over 16 years, mostly in emergency, before moving into postgraduate cosmetic dermatology. While working for a dermatologist, I was involved in a needle procedure on a three-year-old. It went wrong, and I ended up with a dirty needle in my finger and needed surgery.
That became the turning point that made me focus on needle phobia. While recovering, I researched it and reflected on clinical practice and how we manage it in hospitals. I saw connections between early needle phobia and people avoiding later healthcare.
Needle phobia often starts around ages three to six, when children receive many vaccinations. Clinicians have their own tricks, and many are amazing, but there are many variables. I looked at the products available and realised many were designed for children. There was no adult-friendly option. I began experimenting with materials and developed NeedleCalm to be proactive rather than reactive, addressing fainting, trauma, shame and embarrassment.
It is intentionally clinical-looking and low-key. Many of our patients are six-foot-plus men covered in tattoos and piercings. Needle phobia affects everyone. You cannot tell someone they do not look like a person with needle phobia.
Anaita
Can you show us how it works?
Elisha
This is the device. I was astounded to learn that up to one in four adults has needle phobia.
Anaita
I am not astounded. Needles hurt.
Elisha
It is a double-sided pad made from a specialised thermoplastic. You store it in the fridge. One side acts as a desensitising pad. When applied directly above the point where the needle enters the skin, it helps block the pathway of pain signals to the brain. It relates to the gate theory of pain, which has been around for about 60 years. It effectively confuses the brain and desensitises the needle area.
Anaita
What reactions do you get from people using it for the first time?
Lauren
It varies, and people need to be educated about it. I describe it as feeling like a firm toothbrush on the skin. People with severe phobias may take time because their brain expects the pain to be 10 out of 10 based on a previous traumatic experience. With NeedleCalm, perhaps they use it and say the pain was six out of 10. The next time, they use it again. Repeated positive experiences help them become comfortable and build trust with the clinician.
If someone says, “Stop being a baby”, that may be a sign they are not the right person to perform your procedure. There is a psychological aspect to it. The pad is intentionally shaped like a bandage and designed to fade into the background so clinicians do not make a fuss and heighten the patient’s anxiety.
Anaita
The innovation is incredible. Is it registered as a medical device?
Elisha
It is registered with Australia’s Therapeutic Goods Administration as a Class I medical device. That brings requirements, including instructions for use and an advertising code. We need to be strict about what can and cannot be said about it.
Anaita
What is the biggest challenge NeedleCalm is facing right now?
Elisha
There are many competing priorities. It is an ecommerce product, so you need the website, social media, content and marketing. You also need clinical research, funding and stakeholder conversations. There are many shiny objects. The challenge is deciding: if we can do only one thing, what should it be? Some things cost money and generate money; others cost money without generating it. To fund everything else, we need to generate revenue.
Anaita
Who is the ideal target market?
Lauren
Parents and nurses are the top two. Parents see the full trajectory. At the moment, the aim is for them to buy the product and take it into doctors’ practices or hospitals.
Elisha
It is a parallel path. Consumers, including parents, deal with the fallout of a child preparing for a vaccination. Nurses in emergency departments may spend 20 or 30 minutes completing a procedure that could otherwise take two or three minutes. The market can be very broad, which makes the challenge narrowing it.
Pharmacists are also performing more vaccinations, so they are a potential target. But to stay focused, we need to choose the people who understand the full patient story. At the moment, that is the parent.
Tim
Once you narrow in on parents, ask a simple question: where do they congregate? It could be online or in person. For me, the answer includes schools and school gates. It is easier to target one school with 500 parents than to attract 500 separate people to an ecommerce site. What has your school outreach been like?
Elisha
It has been limited, although there have been approaches through online parent communities and Facebook groups. We have discussed school uniform shops. We have found traction in diabetes communities, where parents may be supporting children who have daily injections. That is targeted and specific.
Anaita
If you pursue parents, think about each segment on its own. For school parents, there are school newsletters, school gates and community groups. One parent can love the product and tell the whole school.
Tim
School WhatsApp groups are an undertapped resource. All it takes is one person in the group saying, “I used this for my daughter. It was amazing. Here is the link.” A huge task becomes much narrower: how do you reach that one person?
Lauren
We have seen clusters of orders from similar Melbourne suburbs, which may have come from word of mouth between school parents.
Tim
You can also ask. The art of asking is underrated. Send a follow-up email three weeks after every sale: “Did you use the product? Did it work? If it did, could you share it with other parents?” Make sure they understand your strong origin story. If every customer shares it into a relevant group, there is your audience.
Anaita
You could also create an educational school session. Make something scary and painful feel less overwhelming. Lauren, you are an experienced nurse and an expert who could help children understand the process.
Lauren
We have created colouring sheets featuring Ned the Needle.
Elisha
Lauren has created a children’s activity pack that parents can buy with NeedleCalm. It starts a conversation and helps children engage with the process differently.
Lauren has also worked with the Sydney Phobia Clinic and understands the whole patient journey, including helping people who have avoided needles for years. It is more than a product. It is the origin story, education and the benefit to the patient and their family.
A bad needle experience can lead someone to avoid a doctor or blood test, delay a diagnosis and eventually require more serious healthcare. If we can intervene at the prevention stage and educate the community, that can make a difference.
Anaita
I love the business. In summary, understand exactly who you want to reach. There will always be shiny things. Parents are a strong starting point. Go deep into school communities and the online places where parents gather.
Thank you, Lauren and Elisha, for coming in. Tim, thank you for being our guest expert today.
Lauren
Thank you.
Elisha
Thank you.
Tim
Thank you.
Anaita
I am Anaita Sarkar. Thank you for listening to Unfinished Business. Please leave us five stars, write a review, tell us your feedback and share the episode. We will see you next time.
socialmedia