Contemplating Retirement

What Will It Look Like for a Lifelong Leader?

by 

Jun 14, 2024

I’ve been in charge for decades—raising four children, now onto my grandchildren, hurtling towards my sixties – steering this ship through stormy seas, navigating the treacherous waters of business, and juggling flaming torches all while riding a unicycle on a tightrope. But now, as the years creep up, I wonder: what will old age and retirement look like for someone who’s been a leader forever?

Image credit: Pexels

Picture this

Retirement. A life of leisure, where I’m supposed to kick back, relax, and enjoy the fruits of my labour. Ha! As if I even know what that looks like. The closest I’ve come to relaxing is the ten minutes I spend each morning pretending to meditate before the daily chaos begins. The thought of endless days without a to-do list? Terrifying.

 

People say I’ll need hobbies. Hobbies? My whole life has been one big, insane hobby I somehow managed to get paid for. Gardening? I can barely keep a succulent alive. Golf? Only if it involves running between meetings. Maybe I’ll take up knitting—at least then I can pretend those tangled messes are intentional.

 

Then, there’s the inevitable battle with technology. Let’s face it: I’ve spent years relying on younger, tech-savvy employees to handle the gadgets and gizmos. Imagine me trying to figure out the latest smartphone or smart TV. I’ll probably end up talking to the microwave, wondering why Alexa isn’t responding.

 

Person looking puzzled at a microwave.

If there’s one thing I might excel at, it’s being a grandparent. After all, leadership skills do transfer, right? As my 3 eldest grandchildren hit 7, 8 and 9, I’m already priming them to learn PowerPoint presentations, video editing and some of the small admin jobs that I believe are ‘perfect’ as a Saturday job for them.

 

They’ll probably mutiny and lock me in the playroom, but hey, at least I’ll be in my element.

 

And what about the retirement community? I can picture it now—me trying to organise the bingo nights with military precision, setting up quarterly performance reviews for the residents, and drafting a five-year strategic plan for the garden club. I’ll probably be the first person in history to be fired from retirement.

 

Let’s not even talk about the withdrawal symptoms from not having a boardroom to command. Who will I debate with over the placement of the office plants? Who will listen to my long-winded speeches about synergy and KPIs? My family will have to endure countless “meetings” over dinner, complete with flip charts and brainstorming sessions about the best way to arrange the living room furniture.

Of course, there’s always the possibility that I won’t actually retire, and there will be a constant recycling of the inevitable comebacks. I’ll be that octogenarian who just can’t let go, showing up at the office with my walker, barking orders, and demanding updates on the latest projects. My team will have to gently guide me out the door, only for me to sneak back in the next day.


So, what will old age and retirement look like for a lifelong leader? It will probably be a hilarious, chaotic blend of failed hobbies, tech mishaps, and unwanted leadership in places that don’t need it. But you know what? That’s okay. Because just like running a business, retirement will be an adventure—a new chapter in the story of my life.


And despite the inevitable hiccups, I wouldn’t change a thing. After all, what a privilege it is to have spent decades doing what I love, leading amazing people, and building something worthwhile. And if I end up organising strategic bingo nights and getting fired from retirement, well, at least it’ll make for some great stories.


While writing this and leaning toward the topic, I remind myself that surely, I’m at least two decades away from actual, serious contemplation of retirement. And as my natural entrepreneurship spirit rises, I have now started contemplating all the bat shit madness I can cause chaos with until then…


If you get stuck… call me.

Dawn

Truth is Service