The decision to leave my corporate job in 2008 was one of the hardest ones I’ve made. Whenever I’d question myself and start to flounder, one clear thought would help keep me on track: “I don’t want to be here to get my 15-year anniversary certificate.” I don’t think I was ever very good at my job, and there was something about that milestone that felt too heavy to bear. So, I left.

Other milestones quickly followed: The day a few months later when my house sold; and a few months after that, the day I left Canada with a backpack and a one-way ticket to Zagreb (September 10, 2008), which would eventually lead to me buying a parcel of land on a tiny, remote island in Indonesia (sometime in 2009?) While those markers were no less terrifying, they were also filled with air and light and pierced through with adventure and hope.  

Flash forward to the summer of 2022, when I noticed a whole pile of impending milestones barrelling towards me at once: 30 years in Montreal, 15 years in the same apartment, and of course, my 55^th birthday. One of the three I didn’t have any control over, leaving just two for me to weigh.

They felt heavy.

So, I left.

And here we are in the early days of 2024, almost a year and a half after I packed up and moved to Mexico with my ancient feline, the purry paperweight of my heart, Mimine.

Fifty-five arrived on January 23, celebrated in Montreal by friends and love and flourishes of silver and gold and pungent wafts of birthday candle smoke as I blew my wish out into the universe. It is a milestone that shoots optimism and uncertainty through the chaotic spirals of my greying mane. Where is all of this leading?

For the moment it is all leading back to that tiny, remote island in Indonesia, where, in the wee morning hours of a day in mid-November, I received a message that there is a buyer interested in my parcel of land. I don’t know yet how I feel about this particular marker. A lot of dreams have been sown into that sandy soil over the years. But I think it is time to pass those dreams onto someone else, and free up the road ahead for other adventures.

An excerpt I found online explains milestones like this: “Milestone literally refers to a roadside marker that lists the distance to a particular location. These days, the word is more often used figuratively to refer to significant events in life, like graduating from college or getting married. It acts sort of like the road sign: it’s often a moment when you reflect on where you stand in life.”

Whatever those milestones are for you — career, relationship, the place you call home, that gym membership that’s up for renewal — we owe it to ourselves to heed them as we approach them; to assess if they’re going to lead us closer to where and who we want to be, or pull us toward some muddled path and weigh us down. I won’t pretend for a second that it’s always easy to do. In fact, a lot of the time it’s really, really hard. But if you pay close attention and you are very brave, you will always feel the right answer in your gut.

And if it feels too heavy to bear, call me. I will do my damnedest to help you find the courage to leave it behind. Because, I promise you, ahead of you is where the gold lies.

“Cara’s Paradise”, Gili Air, Indonesia, circa 2009