What Extreme Sports Taught Us About Surviving Early Retirement

Generation X-treme

There’s nothing like cracking an aircraft door at 14,000 ft on a clear summer’s morning.

The air 4 km above the ground is sub-zero. It feels fresh and light compared with the thick, humid air at ground level.

The roar of crisp air rushing through the open door is exhilarating. We crowd around the door with some of the other experienced jumpers.

Someone counts us.

We let go. 

With our heads toward the ground, we reach terminal velocity seconds after exit.

It doesn’t feel like we’re falling. It’s more like we’re weightless. 


It’s the first jump of the day, and everyone’s in a fun mood. We come together and link up. Some jumpers flip from head-down to head-up, flying on their feet.

After years of training in this strange environment, where gravity powers movement and air has pressure you can push off, we don’t need to think about how to move. We just fly.

When You Can Fly

We peel away from flying vertically and track across the sky at a sharp angle. Some are flying on their backs, looking up at the sky. We turn left and right and alter the pitch, challenging ourselves to fly in a tight formation.



Diving steeper toward the ground, we track back to vertical. We come together, flying fast and steep now, carving around each other, like water swirling down a drain.

Then my audible alarm beeps and I wave off. The groups turns and flies in every direction, searching for clear air to deploy their parachutes.  

Around me, colourful parachutes pop open like fireworks.

I feel the familiar thump of my canopy opening and the force of deceleration. Then it’s quiet and the air is warm and thick again.

We’re still 1 km above the ground. We can see the city in the distance and the ocean to the east. Patchwork farmlands quilt the land toward the mountains. The criss-cross airstrip marks the drop zone.

We stack up in landing order and swoop our canopies toward the ground, levelling out at the last moment, our feet skimming along the dewy grass. Then, all too quickly, our weight transfers to our feet, and we are standing on the ground. Slow, cumbersome and earthbound.

Human again.  

Generation X Early Retirement Extreme Sport Lessons

Finding A Way Back

The skydive community is small, insular and obsessive. It’s bonded by the intensity of the sport and the separation between jumpers and ‘wuffos’ – the skydiver term for non-jumpers.

Why are they called wuffos? Because they always crack the same joke, “Wuffo you jump out of a perfectly good aeroplane?”

When skydiving takes over your life, it consumes all your spare time. Eventually, your wuffo friends stop calling, having grown tired of you never saying yes to their invites to earthbound activities.

Inevitably, your friends are replaced by skydivers, and cult-like community becomes your social life, support group and family.

Once obsessed, there is nothing more terrifying than going back to a normal life. Except, perhaps, realising how hard it is to go back.  

Retiring from an Extreme Sport

Retiring from an adrenaline sport is like an extreme version of early retirement from full-time work. If you haven’t thought it through, it’s a blunt stop coupled with a lot of existential angst; what do I do now? what is the point of me? -type stuff. There’s lessons to be learnt for Generation X, which is now starting to produce a cohort of early retirees, and is asking itself, “what next?”

Retiring Early

We ran smack-bang into all the problems new retirees often report: boredom, restlessness, regret and relationship pressures.

I’d like to tell you we dealt with these problems with intelligence and grace, but this isn’t that kind of blog. And we aren’t that kind of people. So we bumbled through the best we could.

Fortunately for you, dear reader, our trauma (and hindsight) offers a few helpful lessons on adjusting to early retirement.

Here’s what worked for us:

Retire Like You Mean It

This one we got really wrong.

With hindsight, we should have left skydiving with more intention, rather than just jumping less and less. It left us with a lingering feeling we had unfinished business.

For a long time, we didn’t entirely understand that we’d actually retired from the sport.

When we retire from full-time work in 1869 days (but who’s counting?), we’ll be more purposeful about it. Maggie and I are ticking off career goals now, while we can, and are resigning ourselves to not achieving everything we thought we would.

Letting go of unachievable goals (my plans for world domination are looking increasingly unlikely) will be important in countering feelings of unfinished business.

Find a Stepping Stone

It’s all down from skydiving (pardon the pun). There are no other sky sports that have the intensity, challenge, adrenaline, camaraderie and general all-round coolness. So it helped to make the first step down as small as possible.

We took up paragliding. The slower, more relaxed nature of paragliding helped us adjust. It took a couple of years to learn the basics, so the adjustment period helped put time and distance between our new life and our old skydiving life.



For early retirees, it could be worth having a stepping-stone as well. Perhaps a part-time job, business or passion project to dive into upon retirement that could make the transition easier. In The Meantime is a project Maggie and I are developing for our early retirement.

Don’t Look Back

Never, ever go back.

Without exception, every time I’ve gone back to something or somewhere to relive a moment or chase a feeling, I’ve been buried under a monumental poo slide of disappointment.

And worse, memories of the original experience were sullied from the poop-alanche of disappointment.

Forget it. It’s better to preserve your fond memories and look ahead to new experiences.  

What next?

Check you’re prepared for early retirement. Take a look at  this post to make a flying start.


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