Halftime Lessons: 23 Things I've Learnt In The First Half Of My Career

I was never good at sport but boy I loved halftime. The ref’s whistle would slice through the fog of competition and I’d shuffle to the sidelines. Out of nowhere, a Tupperware container full of roughly cut oranges would materialise as I caught my breath, slowed down my thinking and focused on all of the action that had just occurred. Those precious ten minutes, squeezed in between the hectic halves, were crucial to playing as best as I could manage; the world came slowly back into the focus and the clarity of distance helped me refuel and strategise.

Today I’m blowing the ref’s whistle on the first half of my career. I’ve worked for two decades straight, beginning at 18 in the mailroom of an advertising agency and ending now a few years after selling the media business I co-founded with some inspiring lifelong friends and business partners.

It’s been a wild, intense, tiring and rewarding first half, and now I’m stepping onto the sidelines to have a break and re-energise. I want to look with some objectivity at what just happened so that my second half can be even more informed, effective and aligned to what I want to achieve.

In reflecting on the past 15 years at Junkee Media (nee Sound Alliance), I’ve compiled a loose list of 23 of the most important things I’ve figured out along that way that I seriously wish someone had told me at the start of my career. It might have saved me a lot of heartache along the way. Here they are, in no particular order:

1. It's harder to make something more simple than it is to make it more complicated.

I started my career as a music journalist writing 50-word album reviews, and quickly realised it’s way easier to write 500 words than it is to refine, refine, refine until there was not one wasted word. I’ve seen hundreds of documents where competing ideas are all thrown on top of each other until the end result is a mess. Knowing what to take out is a skill you can develop. With every project, simplify it until you can describe it in just one page, then one paragraph and finally in just one sentence.

2. The smartest person in the room often asks the ‘dumbest’ questions.

It’s easy to think that those who ask the most obvious questions in a meeting are the least switched on, when in fact the inverse is true. The really smart ones are those who listen, digest and prod every part of an idea to ensure they really understand it, and aren’t afraid to ask the questions that everyone is thinking. 

3. Your workmates are more important than any work.

I’ve been packing up my desk this week, going through old documents that once seemed so important and sending them off to the right departments. The only things I’m keeping are a bunch of Polaroids of long-departed colleagues capturing some of the memories from the five thousand days I’ve dedicated to doing work that I love. Find your tribe at work and stay connected with them long after your email addresses have all changed.

4. Become an expert in one area.

Decide what it is you want to be known for, and then own it better than anyone else. Over the past 15 years I’ve been singularly focused on becoming an expert on millennials, then expanded that into ‘native advertising’, Gen Zs and digital publishing. One of my favourite quotes is from Niels Bohr who said “an expert is someone who’s made all the mistakes that can be made in a narrow field”. Narrow your field down until you’ve mastered it, and only then should you start leaning into other adjacent areas.

5. You’ve usually got six months in a new job before groupthink kicks in.

When someone new joins the team, they’re full of fresh outside thinking on ways to make things better. There’s a real value in that new perspective, and generally it lasts for about half a year before they become indoctrinated into how things are collectively done. Ultimately that’s not a bad thing as you want everyone aligned with a similar approach and vision, but that first six months is a rich, often under-appreciated time to inject new thinking and ideas into your team, so make sure you take advantage of it.

6. The best skill you can learn is how to say no.

This has been a hard lesson for me to learn. I’m an eternal optimist and don’t like letting people down, but you have to know your limits so you can focus on the important things. The further you go in your career, the more important this is. It’s not just saying no without thinking, it’s explaining why you’re saying no and creating rules to help you prioritise. When I chatted with the super productive Zo? Foster Blake for my book Cult Status, she told me her system which I loved: whenever she’s asked if she wants to do something she gives it a number out of ten based on how enthusiastic she’s feeling about it. Her only rule is that it can’t be a seven. If it’s below six, she doesn’t do it, and everything above eight is a ‘hell-yeah’. If it’s not a hell-yeah, then it’s a no.

7. Always hire people who can do a better job than you.

The smartest thing you can do is hire smart people. It’s tempting to feel threatened or intimidated by them, but the best people I've worked with are a thousand times better at doing the work that’s needed than I ever could be. I have such an immense pride at the things the talented people I've worked with have created, and continue to do so.

8. It’s easier to start something when you don’t know anything.

This is one of the great ironies of experience. Naivety is a powerful business tool that most people only appreciate in hindsight. When you don’t know what you don’t know, you really can believe that anything is possible. Of the hundreds of successful entrepreneurs I’ve spent time with, an overwhelmingly large majority had no idea what they were doing at the beginning.

9. Conferences are 20% content and 80% connections.

Work conferences are magnets that attract people in your industry with similar interests, but it took me attending several of them to realise that just sitting in a room passively listening to speakers is a huge waste of time and money. They’re a rare opportunity to forge new connections and deepen existing ones in real life, especially when you’re not in your home town, so make sure you actively use any networking opportunity to actively cultivate new friends.

10. If you’re going to eat shit, don’t nibble.

This learning comes from Ben Horowitz’s book The Hard Things About Hard Things and was quoted often by my business partners / mentors / lifelong friends Neil Ackland and Tony Faure when we went through our own hard times dealing with shit things. When you need to make a hard decision, don’t play around the edges and just go all in. In business there are way more hard times that you could ever predict, but you’ve got no choice except to deal with them and try to move on. So don’t nibble on it.

11. The line between success and failure is razor thin.

Over the years we came perilously close to losing our whole company when times were tough. Some of my most sober memories from the past decade are board meetings with potential administrators and daily cashflow management spreadsheets when every dollar in and out was critically important to maintain solvency. They take a physical and mental toll on you, and taught me to have just as much respect for those who tried and failed as we do for those who 'win'.

12. Learn how to disagree well.

It’s ok to disagree with things, just don’t be an idiot about it. Learning how to argue your points at work with rational, unemotional language and based on solid insights rather than personal opinions or defensiveness will serve you well. I imagine that some people might even disagree well with some of the things on this list, and that's totally fine. These are my opinions, based on my experiences, so of course everyone else's experiences will create their own unique viewpoints. Don't think that you're always right all the time.

13. Inbox zero isn’t for everyone.

You can can fight me on this one, but my experience is that time’s too precious to file emails away and respond to every single one. Improved search has usurped the need for filing, and a good to-do list that you control beats using your email as one. The majority of the barrage of daily emails don’t need a response, and the most important ones will usually return to your inbox or can be resolved with a quick conversation instead of email ping pong. Drop the inbox guilt we’ve been trained to feel, and liberate yourself.   

14. A lot of workplace problems can be avoided with a solid job description.

This is a lesson that I’ve had to learn, many times, the hard way. By being crystal clear at the very beginning exactly what expectations, skills and output are required from both parties, you can hopefully surface any mismatches before you start. This is an area everyone claims to be across, but the difference between a thoroughly understood and vetted job description and a tick-a-box exercise can end up saving you an immense amount of heartache. Trust me on this one. 

15. Do other work outside work.

Applying your brain to solving problems that aren’t your day-to-day actually helps you with your regular work. I wholeheartedly encourage everyone to start a side hustle, volunteer with a non-profit, join a hobby club or just do something outside normal office hours that makes you think differently. Over the past 15 years I continued to throw events outside my day job which has brought me a lot of joy (and income), and have seriously loved being on several boards including the Griffin Theatre Company and Hello Sunday Morning. Applying what you know to help solve someone else’s problems gives you a lot of clarity in return.

16. Attitude beats aptitude every time.

You can always upskill someone in a job, but you can't make a dick less of a dick. Atlassian use the term ‘brilliant jerk’ for the type of colleague who does their job amazingly but can destroy their team’s culture in the process. When we hire for new positions now, we always aim to put a candidate’s attitude above everything else, including how great they might be at doing the actual work.

17. Brainstorms are the most uncreative way of being creative.

There is no bigger killer of creativity than gathering a half dozen people around a table with no preparation and expecting them to come up with good ideas on the spot. Brainstorms are convenient, but that doesn't mean they are effective. Shake up your creative process with different locations, pre-thinking exercises and new people. The best ideas hit you unexpectedly in the shower, during a car ride, or on a walk, and very rarely come from sitting around a boardroom table.

18. Culture is everyone’s responsibility.

Some people seem to think that a work culture is the responsibility of HR, or senior management, but it’s not. Culture emanates from everybody inside a company deciding how they want to work as a collective. If you want to change it, start with yourself and your team and what you can control. Culture is everyone’s responsibility to build and maintain.

19. The best people in your career always come back.

You might eventually say goodbye to all of your colleagues, but the best ones will stay in your life. Most industries are incredibly small, and you’ll end up working with them again in some other capacity. I’ve seen so many great workmates come and go over the years that I never get too teary at farewells knowing that I’ll see them again soon.

20. Turn it off, then turn it back on again.

Trust me, do this before you call IT. For some devilish reason it fixes the issue 99% of the time and saves you the awkward, embarrassed mumble when it miraculously starts working again and you swear to the IT technician that is wasn’t working right before they turned up.

21. Emotions are reflective.

If you turn up at the office in a foul mood, it will often just bounce right back at you. The same is true for the flipside; positivity, calmness and smiles will reflect right back at you and make your entire working environment a way better place to work. This is one of the lessons that applies as much to everyday life as it does to the workplace. 

22. You gain just as much from passing on knowledge as the person receiving it does.

Give away as much information as you can, through sharing research, insights, advice and mentoring. Hoarding hard-earned knowledge is wasting it. There’s a bunch of things you do that you probably think are obvious (and of course it’s obvious to you as you’ve lived it), but that advice might save someone hours, days or months of struggle. When you force yourself to explain things succinctly, you’re the one who ends up learning more about it.

23. Figure out what success means to you, then stop if you get there.

We’re told to keep striving with no end in sight until retirement. Just keep going, bigger, higher, further. Instead of just blindly following that, decide now what success is to you and re-evaluate if you're fortunate enough to get there. I decided early in my career that success to me was creating things I'm proud of and selling a business. I’m very privileged to have reached those milestones, and now it’s time to stop and reflect.

So that’s it. 23 of the things I’ve learnt so far in the first half of my career over the past two decades, most of it the hard way and with so much help from colleagues and lifelong friends drawn from the hundreds of people I've been lucky enough to work with at Junkee and oOh!media. It’s now time to take some time out, cut up some oranges and savour each one.

If you enjoyed reading this, my recently published book Cult Status: How To Build a Business People Adore is out now, and every fortnight I send out an email with one of the most interesting things I’ve learnt. There’s no spam, promise. You can sign up here.

See you back on the field when the second half begins.