Retirement part 6: AFTERMATH

After you step away from your sport or startup - what comes next? What do you do with all that time you suddenly have? How do you move on?

Christie Jenkins

Mar 07, 2023

This is the final blog in a 6 part series on retirement. You should read blogs 1-5 first.

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 dawn of our new lives

It’s 7am on a Saturday morning in July. The sun is just peeking over the horizon. It’s probably 6 degrees outside, and that cold Melbourne wind that blows up from the Antarctic is whistling.

And I’m in bed.

For the first time in 12 years, I’m not on the beach starting my first training session of the day. What a luxury.

Retirement definitely has its moments.

This blog is about how athletes and founders have found those moments, and what comes next.

Start with the small things

Time…

Suddenly you have a lot of it.

I reflected in these conversations that despite working full time now. Despite still doing some form of exercise 6 times a week. Despite starting to try all those activities I could never do when I was a professional athlete… I still feel like I have so much free time. 2-3 hour training sessions multiple times a day, recovery, just constantly thinking about your sport and performance all took up hours and hours each day. Time is a precious sensation.

Most of us started retirement by appreciating the small things. Like being in bed at 7am on a winter’s morning. Or not having sand everywhere in my apartment.

‘Now I’m more present. I can go out to dinner and give my full attention because I’m not thinking ‘I need to be home at 9:30pm so I can sleep and train well tomorrow.’’ ~ Cale Hooker

‘One of the communities I've reconnected with is my high school friends who I hadn't had a lot of time in my life to hang out with. We used to play Dungeons and Dragrons when we were teenagers and so now we have a regular fortnight catchup where we play D&D for hours and hours and hours. It just seems really geeky and dumb. But it's one of my highlights of the week’ ~ Vaughan

‘I’m going to yoga. I’m going for long walks with my dog. I’m going to bed early. I’m prioritising my health.’ ~ Megan

‘I don’t have to do a time trial or skin fold measures when I get back. I like being able to go out to a restaurant and not have to look up the menu to see if there is something I can eat in advance. To enjoy the meal and not be constantly looking at my watch so I can get home by 9pm.’ ~ Matt

Of course, when you’ve had such a mammoth purpose for so long, the small things sometimes don’t feel like enough. That’s normal.

‘I knew people who had exited and got their opinion and they all kind of said the same thing: ‘You're going to lose yourself. You're not going to know what to do with yourself and you're going to get horribly depressed. You'll struggle to get out of bed in the morning because you'll just lose your purpose. This thing was such a driving force for so long - without it you're going to feel lost.’ And I was like, nah, I'm gonna have a great time. It'll be awesome. I'm going to sleep in cause I want to. I haven't slept in in years. But no, they were right. It kind of sucks.’ ~ Vaughan

Protect that time

While we all reveled in the sensation of having more free time, each person also spoke about wanting to hold onto that sensation. To protect that time.

‘I worked massive, massive, massive weeks with my company. Like 80 hour weeks. Probably like athletes train massive weeks. I just assumed more is more. Now, I’m working 40 hours a week and I’m fiercely protective of my personal time.’ ~ Megan

‘I talked with a few of my mates and everyone's like, ‘oh wow, how good is this? You basically don't work, you don't have to worry about anything’. And yet, all I can think about is what the hell am I gonna do next? I've gotta stop myself from thinking about that… Trust your future self. You'll figure it out.’ ~ Rod

‘Make the space to find something new. Don't feel like you need to rush into something new, but you will need to find something new. Just proactively make this space. You need to say no to everything for at least a year. And I did that, and it felt great and in a way it was so liberating. Just politely say no to everything until you're just feeling compelled. There is that risk when you filled up so much of your life with one thing, when that goes it creates a vacuum and then you feel compelled to replace it very quickly with something else.’ ~ Vaughan

‘I got this advice from another player about the power of ‘no’ when you retire. I said no to lots of things. I want to keep my flexibility until I find the thing that I want to dive into.’ ~ Cale

It’s ok not to have a plan

Since retiring, I’ve been asked ‘what are you going to do next?’ hundreds of times. On the sporting front, I have no idea. I’m dabbling in many activities. For once, I’m trying to just have fun with sport without constantly thinking about how to become the best in the world.

There is an expectation in society that you don’t quit one thing, unless you have something better or even more ambitious lined up. Society is not comfortable with ambiguity. When I spoke to Rod, he said that people had even reached out to him saying they’d heard he was working on something new (he’s not!)

Since society won’t do it for us, we need to be generous in reminding each other it’s ok not to have a plan.

‘I used to have like a five year horizon, which was like, I can see myself in five years being here and this is the first time I can remember I don't have a five year horizon. It's like I have no idea where I'm gonna be in five years time other than five years older.’ ~ Vaughan

‘Everyone was asking me ‘what’s next? What are you going to do next?’ I found it really frustrating. I don’t know. I’m taking a year to figure it out. It’s not a helpful question.’ ~ Cale

‘As an elite sports person, you're not at peak performance the whole year - that would lead to sub-optimal outcomes for your body that mean that you wouldn't win. So what's the longer term career version of this? It’s uncomfortable for you to think of this as a deliberately fallow or slow period without a plan or goals, but maybe that's the right outcome.’ ~ Kate

‘I’m trying to just stand behind my decision to go into this and not have a plan. I don't want to focus on work at the moment. So part of not having to focus there is not having a plan. My focus is family, friends, community, me. That's the thing that I'm pushing into.’ ~ Rod

And once they understand, people will be more positive than you expect

I was terrified people would think I was a quitter. That I was a failure. But instead of judgement, what I received was people who sought to understand my decision, and share compassion for the difficulty of it. The question ‘how are you?’ was suddenly asked in a meaningful way, with depth, rather than as a throwaway line.

‘What I would say to founders is your investors have seen a lot more than you imagine. So be less scared about talking to them about it. And also, people don't scratch you off a list of people they ever want to interact with again. They invested knowing there was a lot that they couldn’t predict but also because they care about you as a person as well as the business you’re building. So long as you are all of the things that actually matter, like someone who acts with high integrity, is truthful, responsive… you take the time to speak to people in the right sequence with the right information… then people respond far better than the 2am fretter in you might fear. Hopefully I handled all of the relationship elements of that well.’ ~ Kate

‘It’s actually quite nice to get to know people from a genuine baseline ‘I’m interested in who you are’. Whereas before maybe it was kind of fake. It's like people wanted you because you were successful. You were a leader in your field. So they kind of wanted something from you, whether it was advice or association or money or a job. It's actually quite nice to have people want to hang out with you because you're just you. ~ Vaughan

‘Sometimes there's a little bit of a fear that this will make me irrelevant in a space where I'm considered to be relevant. But I've only received positive feedback from people when I talk to them about what I’m doing and why.’ ~ Rod

Starting to take the next steps

When we retire, most of us don’t know what’s next. But press a little deeper and a common thread comes through - impact and working with elite teams. Before I knew what career I wanted next, I knew one thing: I wanted to work with A+ players. With those who were striving to be world class.

‘Founders are aligned with athletes with their mindsets. There are plenty of setbacks along the way, progress is not linear, but if you have the culture and the team you can win. So I like being involved through Athletic Ventures, I like trying to win with the teams in our portfolio. Founders and athletes are both high energy.’ ~ Matt

‘I tried to list out all of the features of a job that mattered at all to me, even in some small way. Everything from feeling like I'm valued, working with really, really smart colleagues and working on something that I'm passionate about and something that I can be proud to say that I do. Then force myself to stack rank the four or five features that must be true of a job for me to want it.’ ~ Kate

‘I've played a small part so far, but I hope to play a bigger part in supporting and growing a community of other innovators. And these could be people who are well on their journey - they’re trying to figure out how they're going to raise their next capital round or solve a product problem. Or it could be right at the beginning of their journey. Or they're not even on the journey yet. They've still got the awe and wonder of how they're going to change the world when they're 12. The more people that have that mindset of believing that nothing is impossible… We're going to have more amazing startups, we're going to have healthier communities, we're going to have people solving the world's problems. That's kind of my new mission. I could go and do another startup and I have confidence in myself that it would probably be okay to successful. But I actually think the most impactful thing is to go and enable a thousand other people to do that because then we would all be better off.’ ~ Vaughan

Amongst figuring out our own next steps, there is a sense of passing the baton. Stepping aside to make space for a new generation of founders and athletes. It reminds me of the All Black’s mantra: ‘Leave the jersey in a better place’. We each seek to leave our sport, or our industry or the problem we have worked to solve in a better place. And to inspire the next person to take it further.

‘I think that there's a lot of people in sport that get bitter about people's other people's success. I’m never like that. I would almost say that I'm so envious of the people that will get to run at the Commonwealth Games or the Olympics because I remember how good it felt when I was doing it and I'm just like, ‘damn, I'd love to be doing what they're doing, I wish I was out there right now.’ Instead I’m cheering them on.’ ~ Luke

‘We are all passing through. They aren’t going to retire my jumper.’

Advice for others

As you’ve read this series of blog posts, it’s obvious that when we retire we all feel the same things - grief, worry that we won’t find fulfilment again, loss of identity, being behind and having to catch up... We all struggle with the same things. And yet, each of us has felt alone in those emotions and struggles. It is a rare thing to be an athlete or a founder - but not so rare that no one has walked the same path!

Learning from others through these conversations has been the best help I could yet. And in that spirit, I asked what advice each person would give to those also considering stepping away.

‘Making a decision, we sometimes compound the difficulty unnecessarily because we’re worrying about some other factor. In my case for example, how would the team, who I’d been part of convincing them to quit their cushy jobs to come work for this early stage company, how would they feel? How would the investors who had been with me for a long time and had really supported me feel? I worried a lot about that sense of commitment that I'd made to those people. And even, would these investors ever trust me with anything ever again. And that was borne out of a lack of knowledge of how common CEO transitions are these days.’ ~ Kate

‘Momentum matters. Get up, start your day. Before you know it you’ve rung someone, read something. If you stay in bed til 9 or 10, before you know it it’s 12 and you haven’t done anything.’ ~ Cale

‘When I was a young kid and I was going down to Little Athletics they'd always say, ‘what's the best piece of advice’? And they'd say, ‘just have fun or enjoy it’. And I used to think that is the biggest throwaway line. Like that is such bullshit. I hated it. But now I think that that is probably the best advice. It’s so cliche. When you’re young you think performance and fun are at opposite ends of the spectrum and as you get older you realise, ‘oh, if I'm enjoying it, I actually perform better’. Enjoy your career. Then enjoy this time. ~ Luke

‘Be kind to yourself through these transitions. Don't be alarmed if you regret parts of it. Even though it was my decision and in my hands, there are still parts of it that snag me occasionally and I just have to get used to that. That is probably always going to be true.’ ~ Kate

Final thoughts on retirement

Retirement is not the end of your life. But it’s the end of a life. One we should celebrate.

‘People say you should have a funeral before you die so you can hear all the nice things people say about you. When your sporting career ‘dies’ that happens which is kind of nice.’ ~ Matt

‘You become a better player in retirement. People remember the highlights of your career.’ ~ Cale

‘An incredibly pleasing part of the process of stepping out of the role is there are a lot of people who actually explain to you the impact that you or the company has had on them as individuals. And that's really touching stuff.’ ~ Rod

We were athletes. We were founders.

Emphasis on ‘were’ - past tense.

But the dent in the world that we made is not in the medals we won, or the valuation we achieved. It’s not in the skills we developed, or the accolades we received. The dent we made is on other people’s lives.

From these conversations, the biggest thing I’ve realised is that my ability to make a impact does not depend on my role as an athlete. It depends on my role as a human.

And you can retire from being an athlete. You can step down from being a founder.

But you can’t quit being a human.