Why Dreaming Matters (Especially When You Feel Stuck)
When was the last time you let yourself dream?
Not the tidy, goal-oriented kind, but the kind that makes you ask, What if?
The kind that feels a little wild, a little scary—like you’re reaching for something you’re not sure you can hold.
I’ve been thinking about this a lot lately, ever since my friend Ritchie asked me a question I wasn’t ready for: Who am I outside of work? At the time, I gave him a passable answer, and since then, the question has been quietly lingering.
It’s not an easy one to answer. Work has always been a big part of who I am, and stepping outside of that feels unfamiliar. But maybe that’s why dreaming matters so much right now. It’s a way of figuring out who I am beyond the day-to-day grind, beyond the roles and routines that sometimes feel too small.
That’s where dream sessions come in. Jillian once suggested the idea over brunch—her antidote to life feeling too formulaic. We started with brunch, and before I knew it, we were asking big questions:
What do we want?
Where are we headed?
What if we tried something completely different?
I’ve done a couple of these sessions with her, and even a few on my own, and they’ve quickly become a way to shake myself out of the routine.
Then there’s Sara, who has a knack for saying exactly what I need to hear. After one particularly aimless rant, she said, “If you just acted on one of these ideas, it’d be amazing.” She’s absolutely right, of course—but for now, dreaming is enough.
Dreaming has already taken me to unexpected places. During the pandemic, I started singing lessons, which turned into my first gig a couple of years later. I tried stand-up comedy, which was both terrifying and exhilarating. And I gave kickboxing a go, which really challenged me but so worth it. None of this would’ve happened if I hadn’t allowed myself to imagine something different.
Now, having spent a few weeks on holiday and being in New Zealand, surrounded by quiet moments and patchy Wi-Fi, I’ve found even more space to think. There’s something about the slower pace here that has reminded me how much room dreaming needs. It doesn’t happen in the middle of back-to-back meetings or endless to-do lists. It needs breathing space—and maybe a little brunch.
Writing this blog is part of that process, too, because it’s helping me figure things out. It’s a way to show up for myself, to work through the questions, and maybe even enjoy the process a little.
