Sienna Pierre: On your twenties as a trial period
Sienna's twenties have been shaped by curiosity - across continents, career pivots, and the conversations in between. She joins me to reflect on growing up, being vulnerable, and living fearlessly.
If you ever find yourself at a dinner party with Sienna Pierre, there’s a good chance she’ll charm you with a story or two from her travels.
The Seattle-based 25-year-old certainly isn’t short on material - after all, she kickstarted her twenties while on a study abroad programme in France, and since then, has managed to tick off 21 of the 30 countries she’s hoping to visit before turning 30.
“Travel is synonymous with my twenties,” Sienna laughs when we connect over the phone on a sunny Wednesday morning, during which we chat about everything from authenticity and vulnerability, to the best parts of being iced-drink-loving Gen Z gals (coffee for her, tea for me).
“Travelling has helped me prove to myself that I can be thrown into any situation and figure it out. You miss flights and trains, things don’t go the way you want, some nights you have nowhere to sleep, and you just have to stick it out. That has made me confident now that no matter what happens to me, I can handle it.”
And while these experiences have given her plenty of conversation starters - perfect, she says, for dinner parties and social settings - what’s stayed with her the most is the realisation that it’s not actually the big moments that matter, but the small ones.
“We dream of the travel, trips, weddings and big life events,” Sienna shares. “But life is lived in between those things. And I think the more we can bring little, fun activities into our everyday, the happier we can all be.”
That’s exactly why she’s so committed to keeping puzzles and colouring books on hand, signing up for random classes, treating herself to her much-loved iced coffees, and following her curiosities as they emerge. And it seems Sienna is reaping the rewards of that philosophy - there’s a soft, magnetic kind of radiance to her, and a warmth that makes you feel like you’ve always been a welcome part of her world.
Clearly, Sienna has gathered a fair amount of wisdom in her twenties - and when I ask her the one question that’s been sitting in the back of my mind since our conversation began, she proves there’s plenty more where that came from.
“How are you finding the experience of letting your life fall apart?”, I ask, in reference to a striking coming-of-age video she’d previously posted on YouTube, claiming that your twenties are for exactly that.
Sienna laughs, telling me, “it’s going very well.”
“I think in our twenties, we can be messy,” she goes on to explain. “I’ve heard from enough adults that have started over again in their thirties and beyond to believe that the seriousness we often bring to our twenties can be moved up to when we’re in our thirties. For now, we don’t have to take ourselves too seriously. We can be playful and light. We can do things, and then decide we don’t want to do them anymore, and all of that is okay.”
There’s substance behind these words, too, given that last year, Sienna made the bold decision to quit her “not very exciting” desk job and instead pursue a career in social media.
Now on the other side of that leap - which, by the way, she’s incredibly glad to have made - Sienna recalls, “I set the intention of treating my twenties like a trial period for my whole life. I have my whole life to work a steady, stable job, but right now, I don’t have anyone depending on me, so I can take a chance and try a different opportunity. And if it fails, the worst case scenario isn’t that bad, I’ll just come back to a desk job.”
While the work itself lights her up (she’s especially drawn to creating content that helps others feel seen and validated - a natural extension, really, of her caring tendencies as an older sister - and as one of her many keen followers, I reckon she’s smashing it), what’s left the biggest impression is what the process has taught her about herself.
“I have this limiting belief that I’m not a creative person. I’ve just never thought of myself that way,” Sienna admits, acknowledging that part of this likely stems from a deep-rooted fear of messing up. “But in this kind of work, your income is dependent on your creativity. So I’ve been forced to reconnect with what creativity is. I’m still on a journey of figuring out that relationship, but I take it one day at a time, and I’m proud of myself for what it’s turned into.”
We stay on the topic of pride for a while (at my request - Sienna is, to be clear, very humble), but given how intentionally she stays connected to both who she’s been and who she’s becoming, I’m curious about the growth she’s most proud to have experienced in the space in between.
“There’s a fearlessness we have in our youth,” Sienna reflects. “Every year we get older, we become more fearful. But I’m proud of myself for being brave and holding onto that fearlessness. And I’m proud that I’m leaning into curiosity and play. Not to be dramatic, but I think adulthood is a bit of a trap, and every day the temptation to become more serious gets stronger. But the only way we get through the heaviness that life can bring is by keeping it light.
Still, it’s not all lightness. Sienna has, of course, weathered her share of hard moments - and as I’ve come to expect from her, she carries them with a refreshing perspective.
“I’ve made plenty of wrong turns and mistakes in my twenties, but I don’t consider them as that, because everything has brought me to where I am now,” Sienna says, drawing reference to the quarter she took off during college - a choice that threatened to interfere with her ability to graduate on time. It didn’t, by the way - and looking back, it gave her the space she needed to imagine the career she has now.
“That wouldn’t have happened if I’d been rushing to meet the milestone of graduation. I would never have slowed down enough to even realise the conversations I was having were leading me to a potential future career.”
“That’s why I’m big on savouring these precious years,” Sienna goes on to explain. “There’s so much value in being able to live out every season we’re in to the max. Because we’re only in each season of our life for a short time, and once we pass through a phase or a milestone, we can’t go back and live the life we had before then.”
As for right now, Sienna is fresh off a move from California back to her Washington State hometown - and in the transition, she’s learning, for the first time, what it means to rebuild a network of friends from scratch.
“It feels like there’s a new lesson every few months that life and God are trying to teach me. And right now, it’s friendship,” Sienna reflects. “To be honest, with where I’m at, I feel like I’m starting over in a way. I have never been in a place where I’ve had to make all new friends before - and it's made me realise how having people in your corner is so important for your mental health. Even just conversations with your girlfriends about how ridiculous life can be - I’ve come to cherish them more now that I’m not having them as frequently.”
To meet this moment, Sienna has been leaning into vulnerability. “It’s so important to be seen and validated in your feelings, and to do that, you need to be vulnerable with your friends. When you put yourself out there and say you’re struggling, or having a hard time, or even that you’re excited about something, that’s what gives you an opportunity to share in that and to relate to each other. So I’m prioritising that vulnerability a lot.”
The challenge of finding connection in new places is one I know well - and just as two long-time friends might, Sienna and I naturally slip into a deeper conversation about it. A few traded stories later, and we find ourselves laughing - the irony not lost on us that Sienna’s reflections on vulnerability as a bridge for connection have just played out between us, and deepened the connection we’ve been building over the past hour.
And while we could easily keep chatting for another hour (or more - Sienna has a special way of making you feel like she’s got all the time in the world for you), at this point, I decide to ask if she has any parting words for anyone hoping to live with the same presence and depth she does (and, unsurprisingly, she doesn’t disappoint).
“This period of our life is so precious, and I don’t want us to wait until it’s over to realise it,” Sienna says wisely.
”I’m trying to think of a non-cheesy way to say it,” she continues, laughing gently. “But I want to encourage anyone in their twenties to define what this time will be to you. What would make you say, by the end of your twenties, I really lived out this decade in an exciting and honest way? And then work backwards from that.”
Written by Chantelle Cobby for In Our Twenties.
Follow Sienna on Instagram @siennapierre and YouTube @siennapierre.