Retirement part 1: DECISION

When you are an athlete or a founder, making the choice to step away from your sport or startup is one of the toughest decisions you'll ever make. Here is how 8 people thought it through.

My new title: Ex-athlete

A few months ago, I retired from elite sport. 

Again.

It’s the third time. 

The first time, I felt like I’d achieved nearly everything I could in my career. That was trampolining. The second time, I had two pathways to pursue, and had to choose one and leave the other behind. I said goodbye to CrossFit. This time, I felt like I was no longer improving so I made the choice to quit. Farewell beach volleyball. 

For 30 years I have been able to say ‘I am an athlete’. 

Now, I’m not sure who I am.

With thanks to those who are also walking this path

Having retired three times, you’d think I’d be better at it. I am not. So this time, I asked a few other people - both athletes and founders - who are also walking the path of retirement. 

I have always thought that the mindset of elite athletes and founders are similar. Both groups aim for seemingly impossible goals and commit years of their life to them. Just 0.02% of athletes make it to a pro level. Only ~0.6% of founders raise capital, 0.00006% companies become unicorns worth $1B. Both groups are leaders. Both are resilient. Both are optimistic, future focused, and embody grace under pressure. Both have ridiculous work ethics. On the flip side, both groups can be single-minded to the point of being selfish. Both can be tough to work with as we prioritise achieving goals over feelings. And we can be boring - all we want to talk about is our sport or startup. I have always thought they are similar, but this process of sharing our retirement stories has shown we are not just similar, but almost identical. 

Thank you to the following people who so candidly shared their story, struggles, and advice. They are quoted with permission throughout:

Athletes:

• Matt de Boer - AFL player (GWS), now Founder of Athletic Ventures

• Cale Hooker - AFL player (Essendon), now Head of Talent and Partnerships at One Future Football

• Luke Mathews - 800m and 1500m runner (Olympian), who is taking a pause from elite sport and working as a Valuation Consultant at EY

• Me - Trampoline, CrossFit and Beach Volleyball athlete (Australian representative in all 3), and now an Investor at Blackbird Ventures

Founders:

• Rod Hamilton - Co-founder of CultureAmp, who stepped down from the Chief Product Officer role and is taking some time to focus on family and decide what’s next

• Vaughan Fergusson - Founder of Vend, who sold the company for $500M and is now the Inventor at the Institute of Awesome and deciding what’s next

• Megan Bellish - Founder of Bellish, who shut down her company due to burn out, then worked as Head of Founders at Startmate and is now exploring options

• Kate Glazebrook - Co-founder of Applied, who stepped down from the CEO role, and is now Head of Impact and Operating Principal at Blackbird Ventures

This is a 6 part series with blogs focused on:

1. Decision: How to make the decision to retire

2. Unfinished business: Coming to terms with not achieving everything you could have

3. Identity: Grappling with who are you now

4. Mastery: Going from being world class, to being a beginner again

5. Emotion: How to fill the void and find fulfilment elsewhere

6. Aftermath: What comes next and lessons from looking back

Blog 1 is focused on making the decision to retire. And there were some common, and sometimes unexpected, threads that everyone spoke about. 

A gradual process

‘Love the team. Love the boys. Love the pursuit. Love coming in. Love trying to get better. Love being a leader. Love trying to help the team to achieve.’ ~ Matt

How many people could say the same about their career? And if they could, why would they ever consider leaving that career?

‘Not many people get this opportunity, right? Whether it's earned or whether you're lucky or whatever you wanna call it. Like ‘Rod, not a lot of people are in the position you are in where you're part of this amazing company. You get to work with these people, how can you turn your back on that sort of thing?’’ ~ Rod

What became clear over the course of these interviews, was that no founder and no athlete wakes up one day and says ‘it’s over’. The decision is gradual. Carefully considered from all angles. Talked over with people in our inner circles. 

‘The acquisition was a long time in the making. When they presented the final number, it was like zero hesitation. I was like, yep, that's the number, it’s a no-brainer. That number makes sense for everyone involved. But in the lead up I had heaps of hesitation. This was the third go at being acquired by this company. The first two times it was the definite no. And then in the lead up to this one, there was lots of doubt. ‘Are we selling too soon?’ and ‘What would I do afterwards?’. But the number sort of short circuited that.’ ~ Vaughan

‘I spent a few months trying to figure out what to do. Could I recover and continue to lead the company? Could we hire a CEO? Could Bellish go on without me?’ ~ Megan

‘It's hard to test out your thinking with people because of the unique pressures of being a founder. Ideally you want to speak to people who have a sense of that same context but at the same time I do think one of the big challenges is it's a conversation that is hard to unhear. A lot of being a founder is being the face of the ambition and future of the business - for investors and your team.  You spend a lot of your time being the person people turn to for faith and comfort that even in the hard and uncertain times, the future will be bright. In that context, that doesn't leave that much space for your own doubt. And you know that sharing it - especially a big move like stepping back - is hard for those people to unhear. There is a natural kind of limit to how much you want to share your doubts.’ ~ Kate

Two years before I retired I had given it serious thought. Australia’s lockdowns during covid meant no international travel. And travel was both my favourite thing about the sport, and necessary to keep improving both my skills and world ranking. But I wanted to make the decision myself and not be forced into it. I kept training and fought with the Victorian Health Department for a permit to do it during lockdowns (bizarrely they suggested I practise in an indoor sandpit so people couldn’t see me playing my sport!) 

Passion changes over time

‘You’re so lucky to have found your passion.’ It’s a phrase I’ve had said to me more times than I can count. I took that passion for granted. Retirement forced me to unpick what it was about sport that made me so passionate - and why I no longer felt the same drive. Was it winning? The tight relationships I had with my coach and teammates? The recognition you get for being the best? The intense emotional highs of competition?

There are elements of all these things, but the commonality across the decision to retire from all my sports was that I no longer felt I was improving. For me passion = progress. And in beach volleyball, when my coach moved away, my volleyball partner moved away, and the level of players I was training with in Melbourne weren’t as elite, I couldn’t see a way to keep improving. 

‘It's about growth ultimately, and nonlinear growth for me. The thing that I've always been chasing is growth. It’s not that I’ve stopped chasing growth, though. I’m just chasing a different type of growth now, growth in other parts of life that matter to me more now’ ~ Rod

‘Was I still improving? Perhaps in some areas but there was a law of diminishing returns in my improvement. But I was definitely still always improving as a leader, and as a teammate. I don’t know if my passion diminished. I just didn’t think I could keep adding as much value to the team - both on field and off-field.’ ~ Matt

‘I hadn’t taken time off. I hadn’t taken care of myself. I had given everything, literally everything I had to the company for 5 years. I hit a wall. Burnt out. Tried to navigate around it. Couldn’t do it. And shut the company down.’ ~ Megan

‘My passion was racing and, and racing well. When you’re doing a block of six months of training and being at altitude in the mountains and waking up early Saturday and Sunday morning and never having a sleep in… you do all that so that you can run well on race day… But I had back-to-back injuries. I hate cross-training. I hate being on the bike, I hate being in the pool. I hate doing all of that. So when someone said to me, ‘you're getting surgery on your heel to fix your Achilles and you're gonna be in the pool for six months’ it's pretty hard to be motivated.’ ~ Luke

The emergence of other interests

And it’s not just that passion for your sport or startup diminishes, other passions emerge too. To be a founder or an athlete is demanding. There isn’t much room for balance. As new priorities arise the level of sacrifice required to continue in your career can reach a point where the tradeoff is no longer worth it.

‘I had to have the realisation that if you want to be the best in Australia, be the best in the world, you can't really do anything half-assed. I had to have an internal conversation and say with my mindset right now, with what's happening in my life, what's happening in my career, what's happening with my family… can I do what I was doing when I was 20, 21, 22 and put everything else second and running, number one? And I just had that realisation that I couldn't really do that right now.’ ~ Luke

‘My priorities started to shift more towards my family.’ ~ Matt

‘I had the option of continuing on the same growth trajectory, or  another path. One where I could really invest in other areas of my life, which I've chosen in the past to spend less time on. And that's about being a dad, a partner, a brother, and being far more involved with friends and the community.And I looked at the two things side by side and I went, the predictable  path is the CultureAmp one, but I'm really interested in exploring this over here and see what comes of it. And I'm ridiculously privileged to have that choice.’ ~ Rod

For me, I was in love with my new career in venture capital, and I knew to keep improving at beach volleyball would require moving overseas to train and play. I had fought so hard for my job, and I wasn’t willing to give it up. 

Thinking of others

In many ways sport is a selfish endeavour. To succeed, over and over again you must prioritise yourself. You say no to social invitations so you can train. You leave family dinners early so you can sleep. You maintain a crazy travel schedule to compete and miss weddings, funerals and babies. I imagine that the early days of a startup are similar. 

And yet, at the closing of our careers many people are thinking of others. 

‘More than anything, I believed in the business and wanted it to succeed. My passion for the problem we're solving at Applied never waned, nor the people who had dedicated themselves to doing it. And there's no shortage of need for it either. But if I'm being honest, there came a point where I had to acknowledge that I was not the best CEO for the company anymore. That someone else could do a better job than me.’ ~ Kate

‘I was able to help coach the boys and be a leader right up until the end.’ ~ Matt

‘We got acquired by our biggest and most competitive competitor, and had an exit for half a billion dollars. Which I think is huge by everybody's measure. And it was great. This was a great exit for everybody involved. Every investor, the founders, the early staff members all did really well.’ ~ Vaughan

Conviction in the decision

Despite how gradual the decision making process is for everyone, almost universally there was a sense of certainty that it was the right decision. Perhaps it’s due to the naturally forward looking nature of athletes and founders - we briefly celebrate successes but are always looking to the next goal - but no one looked back and doubted their decision. I’ve retired from three different sports, and not once have I thought ‘maybe I should have played longer’.

‘It was the right decision, but it was incredibly hard. It’s so difficult to walk away from your company. Especially when there is something there with the business.’ ~ Megan

‘Everyone says you’re a long time retired - as in you should keep playing. I sort of had the view that you’re a long time retired - I want to be healthy and ready to go.’ ~ Matt

‘I only want to be a runner if I'm an Olympic athlete, I only want to be a runner if I'm one of the best in the world. I knew that if I did it half-assed, I wouldn't be that athlete.’ ~ Luke

And a sense of ownership

What no one explicitly said, but was so obvious it shone through in every sentence, was that every person owned the decision. 

They took 100% accountability for their choice to retire. That was true when their career was externally deemed a success with an exit or a gold medal. And that was true even when they shut down their startup, or were pushed towards retirement due to injuries or their athlete contract hanging in the balance. 

Perhaps this is one of the superpowers of athletes and founders - extreme ownership. 

Sharing is still hard

Making the decision is difficult. Telling your family and friends and teammates and coach… it can be even harder. I’m thankful I didn’t have to make a public speech like Matt did. 

‘I told my wife. Then I called my parents - that was tough. I know they get immense pride from watching. And then my best mates. A few of my closer teammates to give them the heads-up before my retirement speech - I started crying on the phone.’ ~ Matt

‘The people who are close to you have a vested interest in the outcome… my partner, my parents, my friends who wanted me to move back to Australia… They understand that you're ambitious and you're going to do lots of different things in life, but it'd be naive to think that they don't have a personal interest in where you land, even if they support you regardless.’ ~ Kate

‘I don't know whether it’s a running thing or whether it's just a me thing, but I feel with my career I've always ran for and with my family. My mom was my coach. My dad was on the bike pacing me. My friends have always been beside me. So I felt with a decision like that because I had so many people on the journey with me, that they were probably the people that I had to speak to. And realistically the only opinions that really mattered.’ ~ Luke

‘Telling other founders was hard. But they get it. Founders know that every single day there is a small part of them that asks: ‘Is today the day I’m going to quit?’ So the kindness and understanding I got from other founders was really good.’ ~ Megan

For me, my mum was one of the last people I told (sorry mum!) Beach volleyball has always meant family. My parents used to drag me down to watch them play a weekly social league. We had a family 4-a-side team when I was a teenager. I played my first ever tournament with my mum. My brother and I were men’s AA state champions one year when they let me play in the opposite gender. And when my dad died suddenly, it has been the beach volleyball community who have kept his memories alive. 

But because beach volleyball means family, I couldn’t get an unbiased opinion from them. Whether they told me to play or to stop, there was too much history to trust the advice. Instead, I spoke to people 3 degrees removed. Other players who had retired. Friends outside of the sport. Essentially I tested the idea in my mind by saying it out loud to people who just didn’t care that much about my career. 

Then I talked it over with my coach. When he said ‘I’m sad that you won’t keep playing, but in your shoes I’d probably make the same decision’ it became final. And finally, I told my mum. 

Final thoughts on decision

Making the decision to step away from your sport or startup is one of the biggest decisions you’ll ever make. It takes self awareness. Courage. Accountability. It’s a decision made in private but judged in public. There are tough conversations. And you’ll always feel like there was something more you could have done. 

I have made this decision 3 times as I stepped away from 3 different sports. Each time before this I could always still say ‘I am an athlete’ as I jumped into another sport. Now, I can’t.

I am no longer an athlete. But I’m also not the only one trying to figure out who I am now, and what comes next. Thank you to Matt, Cale, Luke, Kate, Megan, Vaughan and Rod who each made me feel less alone on this journey.

The decision has been made. Now the real work begins.