Finding My Way: From Fearless Beginnings to Hard-Earned Confidence

Looking Back: The Start of My Career

It’s funny when I think about it now—I started my career at a level people work years to reach. At 25, I somehow landed the role of Communications Director at a tiny start-up. Even now, I’m still not sure how I got there. My résumé had a few internships, but nothing that really screamed "qualified." I hadn’t written a marketing plan, built a website, or created a media strategy. Most of the stuff I’d done was just surface-level, the kind of tasks you get during an internship. I’d never done any of it on my own either, and I had zero experience in the wind energy industry. Still, the CEO believed in me.

Learning on the Fly

I remember sitting in that conference room, just the CEO and me, hammering out the company’s marketing strategy. It was surreal. For a 25-year-old, it was beyond exciting—empowering, even.

Looking back, I wonder: Was I scared? Did the weight of it all hit me, or was I just riding the high of finally getting a job after so much rejection? Strangely, I don’t remember being afraid. What I do remember is feeling alive, energized. The start-up grew as I did, expanding from a four-person team to over 20 employees. Before long, I was managing a small team—two interns and another communications person.

Gaining Confidence in the Chaos

We achieved some pretty cool things. We launched several websites—one for the company and others for the wind farms—put out press releases, got media coverage, and created a bunch of newsletters, blogs, and marketing materials. For a young marketing professional, it was a dream, and I jumped right in, giving it my all.

So why, nearly two decades later, am I hesitating to take on a management role again? It's been almost 20 years since I last held a similar position. What changed? Well, I did—and so did my experiences.

The Doubts Set In

With time comes experience, but also what some might call baggage. Back then, I didn’t know anything about office politics or navigating relationships at work. Sure, I’d dealt with rejection, but not in a professional setting. I quickly learned. My need to please and be perfect slowly started chipping away at my confidence.

It all started at that first job. One day, my boss bluntly told me he didn’t understand why I had pursued a communications degree because, in his opinion, I wasn’t a good communicator. I was crushed. I remember crying in the office bathroom that day. He intimidated me—he had high standards, and I was desperate to meet them. Over time, he started favoring someone else on our team, a brilliant young woman who was on her way to a legal career. Suddenly, it wasn’t just the two of us building the company anymore. The office filled with new faces, and the excitement I’d once felt began to fade, replaced by doubt.

A Pattern Emerges

That was just the beginning. When I left the company during the recession, the doubts came with me. It shaped how I approached every job after that. I took on smaller roles, never quite reaching that managerial level again. About eight or nine years later, I applied for another management position and was turned down—they didn’t think I was ready. Later, when I joined a new company and the manager left, I was passed over again. No one got promoted; we just took on the extra work without the title or recognition.

Facing Familiar Fears

Now here I am, in a similar situation. Another manager is leaving, and there are no plans to hire someone new. But this time, I’m scared. Years of criticism and rejection have planted seeds of doubt that have fully bloomed. I question myself constantly, even though, ironically, I never doubted myself when I was 25 and knew next to nothing. Back then, I had total confidence in my ability to learn.

Rediscovering My Confidence

It’s wild to think about. Despite having no experience back then, I believed I could do it. I’m still a lifelong learner—I take pride in teaching myself new skills, asking questions, and figuring things out on my own. That’s my strength, and I need to remind myself of that. I’ve got 20 years of experience now. Why am I doubting myself? I can do this. I need to shift my mindset. In this field, there’s rarely one "right" way to do things. It’s all up for interpretation. I just need to trust what I know and tap into the energy and confidence I had when I was younger.

Stepping Up

I got hired back then because my boss saw my potential to learn and adapt. That’s always been my edge. There’s nothing to fear here—except my own self-doubt. And today, I’m more prepared than I was 20 years ago. It’s time to stop running from this opportunity and just go for it.

As I stand at another crossroads, I’m determined to use all the experience, knowledge, and resilience I’ve built. It’s time to turn my fear into fuel and push forward. With my experience and that same enthusiasm I had as a rookie, I’m ready for this challenge.

I’ve got this.

Finding Myself Outside the 9-to-5

The Illusion of Finding Myself Through Work

I spent way too much of myself on my career, thinking it would somehow lead me to who I really am. But it didn’t. Looking back, I realize there was nothing truly me in any of it. Work was just a way to make a living—survival mode—not a way to actually live. I poured my heart and soul into something that could never give back, and in the process, I lost touch with who I am. I let society steer me, following the standard path everyone expects. But in doing that, I ignored what I really wanted.

At the Edge of Something New

Now, here I am, standing at the edge of something unknown. I picture myself in a forest, surrounded by towering trees, crickets chirping, birds singing, and creatures rustling around me. It feels like an invitation to step forward, but honestly? I don’t know where to start. I’ve gotten so good at being the person I was “supposed” to be—the one who goes to college, lands a corporate job, and checks all the boxes. But that’s not the road I want to keep following.

Finding My Own Way

I want to wander off the beaten path, explore the unknown, and take in the sounds, smells, and mysteries of nature. I crave that space to figure things out. It’s not going to happen all at once, and I know it won’t change my life overnight, but it’s a start. And right now, a start is exactly what I need.

Looking Back, Moving Forward

Nostalgia and Regret

Middle age has me feeling nostalgic—a little yearning, perhaps, to have another shot at it all, even though I know that’s not realistic. People often say they have no regrets, but what if I admit that I do? Am I one of the few?

The High School Hustle

Almost 25 years ago, I was fully immersed in my senior year, doing everything possible to secure a scholarship and get into a good college. I dreamed of being an actress, so I threw myself into every arts-related extracurricular: musicals, choir, plays, and forensics. My goal was simple: achieve, then achieve more, until I reached the top. But I was constantly in competition, not just with others but with myself.

With an almost perfect GPA, I found myself lumped in with the “smart kids”—that superhuman clique of students who seemed to excel at everything. Top scholars, top athletes, top performers. Yet, I always felt like an outsider. I was book smart and worked hard to succeed, but I lacked the natural, almost genius-like abilities that my peers had. They shined effortlessly. I was always pushing for what little space was left.

Reopening Old Memories

These memories came rushing back as my 25th reunion approaches. Nearly 25 years gone, and I’m starting to look back. One realization struck me: I never bought my yearbook that final year.

At the time, jealousy and frustration colored my view of that book. It symbolized all the missed opportunities, the roles I didn’t get, the popularity I didn’t achieve. I wasn’t in many photos, I wasn’t the lead in anything, I wasn’t a valedictorian, and I didn’t get the big scholarship. I was close to the top, but I never quite made it.

Now, as a forty-something adult, those thoughts seem a little silly. In high school, I was so focused on what I hadn’t achieved that I missed out on enjoying that fleeting time. I let perfectionism rule my life, when I could have embraced the freedom of youth. Back then, the expectations of others felt overwhelming, and they steered me toward practicality: a journalism degree instead of my dream.

The Yearbook Rediscovered

But back to that yearbook—I finally decided to buy a reprint, 25 years later, to see if those feelings still lingered. Flipping through the pages, I found traces of that old jealousy. The same top students dominated the photos, filling pages with their accomplishments. Out of curiosity, I looked up those seven standout students. Were they still at the top? In most cases, yes—they were lawyers, doctors, financiers, even a hedge fund VP. They were every bit as accomplished as I once thought they’d be.

And yet, seeing this didn’t hurt like I thought it might. Instead, I felt a strange sense of peace. I realized it no longer mattered. Comparing myself to them had held me back for so long, and I finally felt the weight lift. In fact, I discovered something surprising: I’d won an English department award in high school, one for excellence in research and writing. I didn’t remember it, and I certainly hadn’t valued it then.

Discovering My True Passion

My dream was to act, and when that didn’t work out, I shifted to broadcasting. I was still chasing validation, hoping to stand out. But with writing, I found a different satisfaction—a quieter, more lasting one. In the past few years, I’ve embraced my love for writing again, just as I did back then, only now I’m able to see its value.

Looking Forward, Letting Go

So yes, I have regrets. I regret letting perfectionism and competition consume me back then. It’s cost me time and peace, focusing on why I wasn’t like others instead of leaning into my own strengths. But I don’t want to look back anymore. After too much time spent reliving old memories, I’m finally ready to move on.

Here’s to living the next half of my life without regrets. Here’s to letting go of the past and living for myself.

A Battle Against the Inner Storm

The Calm Before the Inner Storm

The sky stretches out, a wide, endless blue with not a cloud in sight. It feels like it goes on forever, like you could get lost just staring at it. The air is warm, almost perfectly still, with just a hint of a breeze brushing by. Sunlight spills over everything, making the trees look like they've been dipped in some kind of shiny gloss. Birds are chirping, their high-pitched calls blending into this peaceful little soundtrack, with the occasional sharp squawk from a blue jay breaking through. It’s late September, and the day feels almost too perfect – like something out of a movie.

The Fragility of Serenity

But even as I sit here soaking it all in, my thoughts aren’t cooperating. Inside, there's a storm brewing, like my mind just can't settle. It's weird how, despite the soft curtains swaying in the breeze and the sun filtering through in this picture-perfect way, I can't shake the feeling that this calm won’t last. Any second now, it could be gone—a kid yelling, a bird squawking too loudly, or someone cranking up a leaf blower. It's as if moments like this are always slipping through my fingers.

Cherishing Beauty in a Transient World

So, I try to take it all in. The warmth on my skin, the breeze, the quiet. This world, with all its small wonders and shiny, fleeting beauty, needs to be appreciated while it’s here. It won’t last. The bright greens and warmth will soon give way to the cold, with trees stripped bare and everything turning brown and gray, eventually buried under snow. The wind will cut through, harsh and unforgiving. It’s strange how the same world can shift so quickly. It makes me miss the summer before it’s even fully gone.

Finding Peace Amidst Chaos

I want to hold onto this moment. I’m trying to quiet my mind, to let go of all the noise and just be here, right now. I think I can do it—if I can just keep myself present, keep my eyes open, and not get lost in the storm swirling around inside me.