23 Lessons From Halftime

Some hard-earned rules from the first half of my career plus a bunch of time on the sidelines.

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 off the field. 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.

Two and a half years ago I blew the ref’s whistle on the first half of my career. I’d worked basically full-time for two decades straight, beginning at 18 in the mailroom of an advertising agency and ending a few years after selling the media business I co-founded with some inspiring lifelong friends and business partners.

At the time I wrote a LinkedIn post to try to sum up sum of the lessons I’d learnt in the first half of my career. I wanted to look with some objectivity at what just happened so that my second half could be even more informed, effective and aligned to what I want to achieve. When a friend recently told me they were taking a mid-career break, I sent them the post and re-read it with fresh eyes.

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One Useful Thing for July 2023: 23 Lessons from Halftime

This month I’m sharing the original post with you, with a bunch of updates and additions since I first wrote it. This a list of hard-earned lessons, in no particular order, that I really wish someone had told me during my career. It might have saved me a lot of heartache along the way and helped me worry less about some of the unimportant things. So here goes:

1. Your workmates are way more important than any work.

When I packed up my desk after 15 long years, the only things I kept from the years of filing and documents and records were a bunch of Polaroids of long-departed colleagues capturing some of the memories from the five thousand days I 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.

2. If you’re going to eat sh#t, 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 sh#t 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.

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

When someone new joins a 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 good advantage of it.

4. 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 helping to run a company 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 have 'won'.

5. 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. 

6. Go deep into one area.

Decide what it is you want to be known for, and then own it better than anyone else. 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”. Start you career as a generalist and then keep continually narrowing down your knowledge until you know everything it. Only then should you really start leaning into other adjacent areas.

7. 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 spoke with super businesswoman Zoë Foster Blake for 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.

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

The smartest thing you can do is hire smart people. It can be 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. It fills me with such an immense pride to watch the talented people I've worked continue to create, manage and lead great projects.

10. 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 expecting to learn is a waste of time. 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 contacts.

11. Learn how to disagree well.

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. It’s ok to disagree with things, just don’t be an d#ck about it.

12. 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.  Even when my emails decreased to a trickle after leaving full-time work, I still didn’t feel the need to file or respond to every single incursion. Life’s too bloody short for inbox zero.

13. Staff zero is incredibly freeing

Staff zero is a mindset where you work for yourself, with no full-time staff to have to manage, inspire or fret over. Since I stopped working full-time in October 2020 I went from managing dozens of people to just being responsible for myself, and the lessons I’ve learnt have been immense. Of course you miss the camaraderie, but on the other side the ability to experiment, explore, and take on jobs for enjoyment and curiosity instead of necessity more than make up for any losses. It’s not for everybody, but if you ever get the chance to work for yourself without the pressures of other people (even if only for a short time), take it.

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

This is a lesson that I 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. Just like a User Manual can help you avoid cluserf#cks, so too can a great job description.  

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. Everyone should 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. 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 an idiot less of an idiot. 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. After hiring hundreds of people over the years I learnt that you should always put someone’s attitude ahead of how well they can do a job.

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

This is the hill I will die on. 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. Heck, I even wrote a whole book about this topic.

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 every single person 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 return.

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. This one has proved itself so true over the last two a half years, as I continued working closely with some of my favourite people.

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

Do this before you call the IT department, trust me. 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 technical help 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 those 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. Since starting this newsletter from scratch six months ago, over 5,000 people now regularly read each edition, and I can’t tell you how much I adore every single message saying that you are using some of the tools, advice and information.

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 then it was time to stop. Instead of having one big finish line at the end of your career, have multiple smaller finish lines and celebrate crossing each of them.

How to use this: Think about these lessons, sit with them and mentally file them away for when you need it most. Share them around with work colleagues you reckon might also enjoy, and let me know which one/s resonate most strongly with you.

I’m currently back in Mallorca, sweating through the steamy Summer, with some upcoming trips to mainland Spain and Finland for book research, interviews and exploring. The second draft of my new book is almost complete, and all of the disparate threads of how to work (and live) better are coming together just at the right time, I think. I hope.

Until next month,

Tim