Confessions of a Control Freak…And My Big Breck Excitement

Everyone knows my favorite time of the year is quickly approaching. Killington opened two weeks ago, and we saw flurries in Boston this week!

It’s almost time for the thrill of crisp turns down my favorite trails, early morning treks up north, and the negative wind chill biting at my nose. You know…Après ski, meeting new ski friends, the whole thing.

I’m ecstatic.

Remember my post about staying present last summer? How I wanted to make sure I was living in the moment without wishing the warm months away? I did it! Between trips, weddings, ocean days, time with friends, and soaking up the summer, I didn’t even have time to miss ski season.

It’s been almost eight months since I last touched snow…and I’m spending Thanksgiving Breckenridge, CO. My parents left the planning to me, and my inner control freak has had a ball. Five days of gallivanting around town, staying in a drool worthy ski town Air BnB, cute outfits, mountain views, skiing (!), and extravagant dinners—all perfectly scheduled.

But suddenly, my brain is full of “what ifs”: What if skiing doesn’t live up to the hype? What if there’s only one trail open and my family is bored? What if my perfectly scheduled plans are a bust?

Oh, and the ‘what ifs’ aren’t stopping there—they’ve officially expanded to the whole ski season. What if the season isn’t as fun as last year? What if I lost my love for skiing because I didn’t obsess every minute of the summer about it?

Isn’t it funny how the human brain works? I successfully manage to stay present, and now my mind is bugging me about the pressure and expectations for this trip and season. UGH!

Here’s the thing—especially with the holidays coming up. We love to hype things up. That anticipation? It’s dopamine, baby. It feels good to look forward to something during short, dark days. But at what point do we go from being “excited” to “setting ourselves up for disappointment”?

Are we spending too much time constructing perfect scenarios in our heads, only to be let down by reality?

Am I so worried about everyone else’s experience that I’m missing out on the excitement before the trip even starts? Kind of like last April, when I was worried that I’d miss an entire summer of fun because I was pining over my cold weather fling…skiing.

How do we make sure we’re living in the present while enjoying whatever life throws at us in that moment?

That’s a loaded question. I think it starts with separating hopes from reality. Notice when you’re projecting or building up a situation in your head. Focus on what you can control — like your mindset, your plans, or your boundaries — and have a flexible Plan B for the rest. That’s how you stay grounded instead of disappointed.

By tempering our expectations, we can allow more joy in. By shifting our mindset, we’re able to live in a way that is more prepared for enjoyment and less set up for disappointment. We can prepare ourselves with whatever we need beforehand—which is different for each situation.

For me, that means reminding myself this ski season won’t be the same. And that is okay! It will be filled with my serotonin sticks (hi skis), friends to share the slopes with, and the ski days that I obsess over like a hit of a drug. It will be a fun season because I will be doing what I love—and that is perfect in itself.

And our trip out west? You all know Colorado is my favorite place on Earth. Honestly, I could have the worst vacation ever and still be grinning—because, hi, I’m in the mountains! Time with family, skiing, cozy dinners—there’s no need for high expectations. I can just exist and enjoy everything it has to offer.

And honestly, this mindset doesn’t just help when things are exciting. It works when stuff goes sideways too—plans change, people flake, or the vibe just isn’t what you pictured. Keeping expectations realistic lets you roll with it instead of spiraling. I’ve found that the imperfect days end up being the ones you remember most anyway.

Take last Thanksgiving: I had to work the day before and after, felt lonely and sad, and my expectations of family time were crushed. But then I volunteered, made my own turkey and stuffing, had a hot toddy…and that holiday ended up being surprisingly memorable, even alone.

Being realistic with our anticipated outcomes or excitement doesn’t mean never being excited for something. Trust me—I become like a kid at Disney with a turkey leg when I get to ski again or see my family for the holidays. I’m giddy with excitement.

What I am saying is that if we just chill and drop the expectations, we might actually surprise ourselves—feeling grounded, content, and fully there. Whether it’s Breckenridge slopes or the holiday chaos at home, being present wins every time.

You all know I’ll be testing this theory on my trip out west—send me your own holiday expectation meltdowns, I want the full report.

Happy expectation managing,

Charty

And get ready for major Breckenridge content — I’m taking you along for the whole trip (with an itinerary blog coming soon, obviously.)