I used to think the good part of life was something you earned — a reward waiting for you on the other side of retirement, once you’d put in enough years.
Then I learned the hard way that isn’t true.
If you’re waiting for someone, or something, to finally tell you it’s your turn, here’s what I want you to hear:
It’s time to stop waiting for permission to live your life
Here’s how I learned that…
It was the summer of 1990.
I was a 20-something year old, working as a concierge at the Hyatt Regency Hotel in downtown Vancouver — booking restaurants, selling city tours, chatting with pretty much every guest who came through the lobby.
(Man, how I loved that job.)
It was my first cruise ship season.
A lot of those guests were couples and retirees, finally taking the big trip they’d been promising themselves for years.
But sadly, more than once, I heard that someone hadn’t made it back home from the cruise.
That vacation was their last.
They’d waited. Worked hard. Saved up every penny. But when retirement came they never got to live the life they’d spent decades waiting for.
I remember hearing that and thinking:
Holy sh*t, I am NOT doing that! I’m not putting the good things off until “one day.” I’m going to do them now.
It was an important life lesson, and one I’ve been living by ever since.
Sure, life hasn’t always been easy…divorce, single motherhood, aging parents, 9-5 jobs with brutal commutes.
And even now that I have more time-freedom, I still have plenty of responsibilities: two businesses, a mortgage, a son who’s finishing his degree and still lives at home.
But I’ve never forgotten what I learned that first cruise ship season.
How important it is to live our lives now.
What actually fills me up
Case in point: every summer, I drive up to the Okanagan in BC, where I spend a week with my sister and her family.
Pool days, family BBQs, bike rides around the rolling hills. Feet up, wind chimes tinkling, warm summer sun on my face.
Then I head east to spend another week with a dear friend from my Toronto days — long walks, late-night chats, fitness classes, and spontaneous visits with other family members and friends.
This annual getaway isn’t a big decision for me.
It simply starts with: when am I heading up to the Okanagan this summer? That’s it.
This trip fills me up because it meets my top values — freedom, connection, fun, ease, adventure. And that’s not a fluke.
That’s what happens when you get clear on what matters most to you, and start building it in, in whatever small way you can.
Over time, it becomes the shape of your life.
Stop waiting for permission to live your life
So many of the women I’ve worked with get stuck in the waiting.
⌛ Waiting until retirement to take the trip.
⌛ Waiting until their kids are launched.
⌛ Waiting until their career feels stable.
⌛ Waiting until they’ve somehow earned the good stuff in life.
As if there’s a future version of themselves who finally deserves it.
But what if this is the good part? What if the things that fill you up — the ones that bring you joy and contentment — don’t need permission to happen now?
You don’t need a big leap
My younger, hotel-concierge self would take one look at where I am right now — the pool, the sun, the e-bike rides, the family get-togethers, the not-waiting — and think:
Yeah baby. That tracks.
But none of it started with a big decision. It started with one small thing: choosing the Okanagan trip over “someday,” one summer at a time.
That’s really it. You don’t need the whole plan. And you don’t need to feel ready.
You just need one honest, tiny step in the direction of the life you keep putting off.
If you’re waiting to feel ready before you start, I put together a free guide — How to Stop Waiting and Start Moving Forward — to help you find that one small step and actually take it.
Kerry xo