🌿 A Decade in Review: Highlights, Challenges, and Transformations of My 20s

Theresa Wilson
Aug 22
5 min read

As I step into a new decade of life, I’ve found myself looking back—replaying memories, reliving milestones, and sitting with all the unexpected moments that shaped my 20s. It’s hard to believe how much life fit into ten years: the false starts, the slow growth, the quiet wins, and the lessons I didn’t know I needed. This decade wasn’t always easy. There were seasons I struggled, times I felt lost, and chapters I didn’t think I’d make it through. But looking back now, I see how each twist and turn brought me closer to myself—even when it didn’t feel that way at the time.

What follows isn’t just a highlight reel. It’s a reflection on the shifts, the setbacks, the soft moments of becoming. It’s an honest look at where I started, how far I’ve come, and the version of me that’s emerging as I move into my 30s. If you’ve ever felt like your journey didn’t follow the timeline you expected—or like your growth was happening in the background—I hope this reminds you that it still counts.

✨ The Highlights: Little Moments, Big Shifts

Looking back, the highlights of my 20s are a mix of loud, exciting milestones and quiet, meaningful moments that shaped who I am today.

I changed my path multiple times before landing in the job I have now. It wasn’t a straight line, but each turn brought me closer to something that felt right.
I reconnected with my passions—writing, photography, reading, and creating—after years of feeling disconnected from them. Letting creativity back into my life felt like coming home.
I took a solo trip to Victoria, and while it was recent, it deeply shifted the way I see myself. It was proof that I’m capable, brave, and allowed to choose myself. That trip also sparked a new desire for adventure—next weekend, I’ll be heading to Banff for my very first trip of my 30s, and I’m already planning another adventure for next year.
I made lifelong friendships and, along the way, slowly learned what kind of people I want to surround myself with—those who are kind, intentional, and energizing.
I took creative risks—even when I wasn’t sure anyone would care—and started showing up more as myself, online and offline.

Some highlights were clear “big moments,” but others were just quiet affirmations: the first time I said no without guilt, the first time I asked for what I needed, the first time I believed I was enough.

🌧️ The Challenges: What Shaped Me Most

Not every part of my 20s was easy—in fact, some years felt impossibly heavy. But those hard moments played a big role in shaping who I am today.

I was diagnosed with depression and anxiety shortly after my 20s began. Even with a name for what I was feeling, it took years to truly understand how deeply it affected me.
I struggled most between 2019 and 2023, when my mental health hit some of its lowest points. Some days it felt like I was just surviving—but even that was a form of strength.
I experienced heartbreak in the form of a ten-year friendship that slowly faded away. Letting go of that connection hurt in a quiet but lasting way.
I dealt with financial stress and had to learn to ask for help—something that challenged my pride but ultimately taught me the power of vulnerability.
I spent years feeling lost, like I wasn’t where I was “supposed” to be, and carried the weight of comparison and uncertainty.
I believed that focusing on self-care was selfish, only to realize later that taking care of myself was one of the most important and transformative things I could do.

But looking back, those hard seasons held some of my biggest transformations. They taught me to slow down, listen to myself, and choose my well-being—even when it wasn’t easy. Those years weren’t what I expected, but they shaped me into someone stronger, softer, and more self-aware.

🔄 Growth I Didn’t Expect

What surprised me most wasn’t how much I changed, but how quietly it happened. Many of the highlights of my 20s were also moments of quiet growth. They weren’t always dramatic, but these small shifts added up over time:

Learning to sit with discomfort instead of numbing it
Finding peace in routine when I once craved constant change
Embracing slowness as a strength, not a flaw
Letting go of what no longer fit—even when it used to mean everything

One of the biggest lessons I’ve learned is that asking for help is not a weakness. For several years—and even now—I still live with my parents due to affordability, leaning on their support as I build my life. Living with family isn’t a setback when it’s part of a loving, supportive system. Accepting help when it’s available is an act of strength and self-care, not failure.

My 20s pushed me to unlearn a lot: perfectionism, people-pleasing, and the pressure to constantly perform. In the space that unlearning created, I began building something softer, steadier, and more aligned with who I truly am. Even the difficult moments became part of the highlights of my 20s, teaching me resilience, self-awareness, and the importance of choosing myself.

💌 What I’d Tell My 20-Year-Old Self

If I could go back and speak to myself at 20, I’d say:

“You don’t have to have it all figured out. You won’t, and that’s okay. Life rarely follows a straight path, and the version of success you’re chasing now will change as you grow.

Trust yourself—especially when it feels hard or uncertain. Take care of yourself, and don’t feel guilty for making your well-being a priority. Self-care isn’t selfish—it’s necessary.

Try not to get caught up in what others are accomplishing. Everyone’s journey is different, and comparison only steals your joy. You’re exactly where you need to be, even if it doesn’t always feel that way.

Let things fall apart if they need to. Sometimes what’s breaking is making room for something better—something more aligned with who you truly are.

🌅 Looking Ahead to My 30s

I’m not entering this new decade with a grand plan—no detailed blueprint or rigid checklist—but I am bringing with me a newfound clarity, deep gratitude, and a lot more compassion for myself. After the twists and turns of my 20s, I’m learning to embrace the unknown with openness instead of fear. I’m excited to live more intentionally, to nurture what truly matters, and to keep growing into the person I want to be—even when the path ahead isn’t perfectly clear.

My 30s feel like an invitation to slow down and prioritize balance—between ambition and rest, between dreaming big and appreciating the present moment. I want to cultivate more meaningful connections, deepen my creative passions, and build a life that feels authentic and joyful. There’s still so much I want to do, so many places to explore, stories to tell, and experiences to savor.

This decade begins with a symbolic first step: a solo trip to Banff next weekend. It feels like the perfect way to welcome my 30s—with courage, curiosity, and a sense of possibility. From there, I’ll continue chasing experiences that stretch me, inspire me, and remind me that choosing myself is always worth it.

What feels different this time is that I get to step into these goals with experience, self-awareness, and a little less fear. I’m more patient with myself, more willing to take detours, and more confident that even the setbacks hold value. This decade won’t be perfect, but it will be mine—full of learning, love, and quiet strength.

Until then, thank you to my 20s—for the lessons, the losses, the late-night thoughts, the love, the rediscoveries, and everything in between.

Here’s to the next chapter. 💫