Retirement part 2: UNFINISHED BUSINESS

Athletes and founders are incredibly future focused. One goal done, onto the next. At the moment of retirement, there is always a goal left undone.

This is blog 2 of a 6 part series on retirement. You should read blog 1 first :) 

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

The athletes and founders featured are:

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

The dark side of belief

My beach volleyball partner and I are 14-9 down in the third set of a quarter-final match. The set only goes to 15 points. 

The odds of winning from this scoreline are minuscule. One error, one point, or one good hit from our opponents and it’s over. The crowd is already starting to stand up, think about the next game they want to watch, and leave the court. In a decade of playing I’ve seen a team win from here maybe once. But today, we are making it happen. 

We will not lose. 

The other team serves. Right down the middle, trying to cause confusion. But my partner and I are playing in sync, and there is no hesitation as she takes the pass. I set. And she hits the ball smoothly and cleanly for a point.

14-10. 

My serve now. Unlike tennis, in beach volleyball the advantage is with the receiving team. This serve needs to be something special. But if I miss… we lose the match. 

I know I’m not going to. 

The umpire blows the whistle for the point to start. I lock eyes with the player we’ve been targeting all match. She knows it’s coming to her. I toss the ball. Make contact. It’s a short serve, barely clearing the net. A serve we rarely use. But I’ve spent the off-season practicing. 

The opposing player dives for it. Falls on her stomach. Arm outstretched. But the ball hits the sand before she gets there. Point for us.

14-11.

I go back to the baseline. Stare again at that player. Try to put even more pressure on her to make a pass. 

I serve short again. Such a risky serve twice in a row. I see the moment of disbelief in her eyes as she realises what I’ve done. She scrambles forward. Too late. Ace. The crowd, who had switched off earlier, are back with us. To them, winning is possible again. Maybe.

14-12. 

This time she takes a big step forward, ready for the short serve. Instead I serve high and deep - over her head. The ball floats in the wind, making it almost impossible to read. She touches it but it flies off in a random direction.

14-13. 

They are arguing on the other side of the net. 4 match points have slipped through their fingers. My partner and I are smiling. We have this. 

The next point they pass the ball, get it set on the net. But her confidence is down and the pressure has risen. She hits the ball out.

14-14. Tied game, and the momentum is with us. From here, the first team to get a two point lead will win the match. 

I whisper to my partner, tell her to run a fake. It’s a play we’ve kept up our sleeves the whole game. Right before the player attacks, she pretends to pull off the net, making it seem like the court is open for an aggressive hit. The opposition winds up her arm, jumps, looks up at the ball. And then suddenly my partner is right in front of her with a perfectly timed block. And the ball bounces down onto the sand on their side of the net.

14-15. Match point to us. 

Once more I go back to the baseline to serve. Before I even toss the ball, I know we have this game. 

And once more, I take the risky option, the short serve. This time right in the middle of the court. Both players dive for it. They lay out at full stretch on the sand. And both miss. 

Our point. And our victory.

It’s a shock to our opponents. It’s a surprise to the crowd. But to my partner and I… we believed we would win this game. We did not hope. In our minds it was a certainty. 

It is this absolute belief that makes the mindset of elite athletes rare.

And it doesn’t just happen in games. It applies to entire careers. Athletes pick a goal so crazy people tell them it’s impossible. A goal that will take decades of insane work ethic to have even a tiny chance of success. But they believe so strongly, and for so long, that those goals often become reality. Founders do exactly the same thing. They will an idea into existence with their belief. 

‘I know I suffer from this problem where it's like I can see something that seems so obvious. I can see success in the future. I can almost smell it and taste it. I can almost draw it for you. So that becomes the belief. It seems really obvious that we can totally go do this thing and it's going to be amazing when we get there. But what I've come to realise is that most people don't operate that way or they don't see what you see. And part of being a leader in an organisation is sharing that vision and just making sure that everybody can see and believes the same thing that you believe. Otherwise they're just sort of turning up for a paycheck. They need to absolutely, to their bones, believe the same thing that you believe.’ ~ Vaughan

Founders and athletes can see the future. And they don’t just see it. They expect themselves to achieve it. They possess unwavering certainty that they can. And as each goal is achieved, we again look to the future and see that we can do more. 

But then what happens when you retire? No matter how successful you were, no matter how many medals or millions of dollars you have, there will always be a goal left unachieved. And not just a goal that would have been nice to have, but a goal that you know, with zero doubt, was possible for you.

No matter when you retire, there will always be unfinished business. 

‘I do have a lot of stones left unturned in the sport. I would've always thought that I'd end my career with a couple of Australian records, a few more medals at majors, a few more national championships. I just know that I probably just didn't get the most out of my career thus far. I think that I should have ran a bit quicker. I think that my PB should definitely be a lot lower I probably should have a bit more success at a championship level. But that's the thing with running, it's like there's no real finish line.’ ~ Luke

‘There's no natural point to step off. People will always feel that they're never done. I do still feel a sense of unfinished business because I know that problem is nowhere, nowhere near being solved.’ ~ Kate

‘In terms of what my expectations were… I got halfway there. I was on the path. I could have done more. But you need to think about how you share that feeling externally because you don’t want to be knocking yourself down all the time.’ ~ Megan

Effort over outcomes

I did not achieve everything I wanted to in sport. I went to 5 World Championships. I competed in the World Games, the CrossFit Games, and on the World Tour. I was the youngest ever athlete to go to the Youth Olympics for Trampolining and I won bronze. Across 3 different sports I’ve won over 40 national titles. I have international gold medals. And Australian records. 

But… I never went to the Olympics (and annoyingly that’s always the first question people ask when you tell them you are an athlete). 

I have unfinished business, and a goal that will never be achieved. Like most founders and athletes, I tend to measure myself not by how far I made it from the starting line, but by how short I fell from the finish line. 

When I asked how others were dealing with this dichotomy - how they reconciled an overall successful career with their unmet goals - everyone emphasised effort.

‘I got the best out of myself. I finished my career and I left no stone unturned. That’s all I can do. I gave it my best.’ ~ Cale Hooker

‘Try to have no regrets. You are doing everything you can, right? You're doing everything that you're told by your coach? I think that's probably the best way to go about things because at least if you go somewhere down the track and say, well, what else could I have done? You know, I didn't win this race or I didn't do this, but I did everything that I possibly could. And I mean, there were times in my career where I did everything I possibly could and it didn't work out. And there were times where I did everything I possibly could and it did work out.’ ~ Luke

‘One thing my coach would talk to me about a lot was, ‘Hey Rod, when have you done enough? When's done? When can you feel comfortable with what you've achieved in this domain?’ I used to always talk about having unfinished business. There's more I want to achieve, there's more to be done. It took me a while to get there, but now I can feel good about what we’ve done. I can think ‘okay, I’ve done enough.’ ~ Rod

Kindness and gratitude

What each person also spoke about, but most were finding hard to do, was to be kind to themselves. To look back with gratitude for what they did achieve, and to be kind to their earlier selves. It’s hard to balance this against those high expectations we have, but we can see that this is the path we should take with our thinking. 

‘Even if you win 10 premierships, you’ll wish you’d won 11. No one will ever be completely happy. No matter what, you have to look back with gratitude.’ ~ Cale 

‘I don’t like the word regret. But you always want more. I played in 2 grand finals. I lost in 2 grand finals at the AFL level. I won a WAFL grand final which I’m really proud of. You look back and think ‘if I’d done this a little bit differently, if I’d focused on that, what if I’d played a different position…’ All those things do go through your mind. I’ve just promised myself to be content now, and not wrestle with that. To just be excited by the future… I like to think the relationships I’ve got with my teammates, and the impact we’ve had on each other, is what I’m proud of. You can always do more, and you always think you should do more, I’ve just tried to let myself off the hook and be proud of what we have achieved and not what we haven’t...’ ~ Matt

From someone else’s eyes

We fixate on the small things we could have done better. At my last trampolining world championships, after completing a series of double somersaults with multiple twists in a perfect layout position… I took a single step on my landing. That was the difference between a medal, and 9th. 

To anyone else, top ten in the world is something inspirational.

Immersed in the day-to-day of training or building a company we forget that what we are doing is out of the ordinary. That other people look up to us. During each conversation I had with the people in this blog, there was a moment of magic where they stepped out of their own head, and viewed their career from someone else’s perspective - a friend’s, a fan’s, a stranger’s. There’s a dawning realisation that the path they have chosen is unusual, what they’ve achieved is rare. 

‘You take for granted what you’ve done’ ~ Luke

‘There’s a bit of imposter syndrome throughout my career. Like ‘I’m not a professional athlete, I’m just Matt that’s trying to get better everyday.’ Some people put you on a pedestal and you’re astounded by that at the time. I’ve never really aligned to the pro-athlete tag. And maybe that’s held me back. I don’t know. I just tried to come in every day to get after it, to get better, and be a great teammate’ ~ Matt

‘It could be so easy to think: ‘I didn’t reach a billion dollar valuation and therefore I’m a failure.’ But when I step back and look at everything we did achieve, it was extraordinary.’ ~ Megan

Cutting ties

A lot of people asked me ‘why don’t you just play volleyball for fun?’ 

My coach even reminded me that most players who retire and play the next season for fun tend to have their best ever results (you haven’t lost your skill or fitness, but you don’t have any pressure so you play relaxed). 

For me, it was easier to make a clean break. Zero tournaments. I never want to play and feel like I was slowly getting worse. And perhaps it’s egotistical, but I don’t want to lose to teams I used to beat when I was training properly. 

For athletes paid to be in a team the decision is naturally more binary. But for those like me in sports where you pay your own way to play it’s a decision that can be left open-ended.

‘I think that me going back to professional running is not highly likely, but at the same time, I don't want to say I'm retired. I’m taking a pause.’ ~ Luke

And for founders, it’s even less clear. Their hard won skill and expertise doesn’t diminish with reduced physicality like an athlete. Both Kate and Rod remain on the boards of Applied and CultureAmp respectively. 

Final thoughts on unfinished business

A huge part of the mindset that sets elite athletes and founders apart is unreasonable, unshakable belief in themselves. We expect to achieve the impossible goals we set. We see the future and will it into existence. 

It’s what sets athletes and founders apart, but it’s also what results in this universal sense of unfinished business. 

‘That was the hesitation in selling Vend. It's like, ‘I think we could take this to be a billion or 2 billion or 10 billion’. And I've seen that in other founders and entrepreneurs. They see something or believe something that most people wouldn't and they can see no reason why they couldn't go and achieve that thing. Almost irrationally.’ ~ Vaughan

No matter when you decide to retire, there will always be something left undone. To deal with this requires us to look back on our careers and be kind to ourselves, to be grateful for the experiences we had, to remind ourselves that we gave every effort, and sometimes to view our careers through other people’s eyes - with a little bit of awe.