It’s a happy, happy morning because after I hit send, I’m packing my Away luggage with cozy knits, stocking up on some Whispering Angel and Bordeaux, and jetting off on a girls weekend to Tremblant.

And while it’s only a 2 hour drive from Ottawa, it does cross the provincial border into Quebec, which can only mean one thing: euro vibes and our impending metamorphosis into deux Parisiennes. Maybe even dusting off those high school French immersion skills…

Weekend motto? Boujee Vibes Only.

But fabulousness aside, a spa weekend away also happens to be where my career masterminding goes down. It was last year on this same trip (if you know me, you know I love turning everything into an annual tradition) that I decided to leave my Shopify identity and step into my mixed-bag career of writing and project management.

Ahhh, nothing like a walk down memory lane.

Am I alone in my forever-nostalgic mood? There’s something about looking back a year—where was I? What was I pining for? What were my goals? What scary things did I do?

When I look back and connect the dots of my career, it’s always the impulsive moves that made a bigger difference than the over-planned ones.

The over-planned ones take us from point A to point B, but the impulsive ones can take us from point A to an off-grid wonderland.

(And this is coming from a project manager who, by definition, makes a living from making plans.)

That’s because the leap from Nothing to Something takes magic. Prepare to confuse the hell out of everyone around you.

And the step from Something to Something 2.0? That takes planning. It’s going from grade 5 to grade 6 to grade 7. From entry-level to mid-level to senior-level.

It’s a career built on “More”.

But moi? I prefer a career built on “And”.

Miguel started building his “And” career this year and it’s been wonderful to watch those first steps unfold. Oh, how familiar the transition! From excited idea to imposter syndrome, from confidence to overthinking, from strong boundaries to people pleasing.

The cycle of emotions when starting something new is annoyingly predictable. And it’s something you can’t understand until you’re in it yourself. Which is why I delight so much in pointing out, “Ha! Now you know why I overthink!” or “Ha! Now you can see why I doubted that thing that seemed so insignificant!”

There is soooo much I want to dive into on this emotional cycle (maybe I’ll write a future Friday Newsletter on this topic?)

But something else I’ve been noticing are the questions he’s getting:

So… are you quitting your job now?

So… is this your new career?

So… what’s your plan with this?

Mixed in with a few opinions, too:

Maybe test it out a bit longer before fully committing.

Maybe grow slowly so you don’t fail.

Maybe just keep it small for now.

A career built on “And” looks different from a career built on “More”.

But being understood is overrated.

Having an understandable career is overrated.

We’re pursuing twisty-turny careers over here. The ones that ruffle feathers. The ones that might even ruffle your feathers.

Thankfully, we’re not afraid of a little imposter syndrome or overthinking.

Heck, I overthink what chocolate to get at the store.

Now if you’ll excuse me, I have to go overthink what outfits to pack.