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

From a fearless 25-year-old in a startup to facing self-doubt 20 years later, I’m ready to embrace my experience and rediscover the confidence I once had. Here’s to stepping up again.

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.

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Breaking Free from the Shadows

In this journey of self-rediscovery, I confront feelings of anger and emptiness. It's time to let go of others' expectations and reclaim the joy and clarity that comes from embracing my true self.

The Weight of Emptiness

I am angry. I feel abandoned. I feel alone. I feel like no one cares. I’ve never had such a burning sensation of worthlessness or been so unsure of how I fit into the grand scheme of things. I just don’t know where I’m supposed to go or what I’m supposed to be. Everything feels gray and uncertain.

Trapped in Stagnation

I hate the uncertainty. I hate not knowing and feeling stuck. I guess that’s it – I just feel stuck, unfilled, and lost in my own thoughts. Why do I always feel this way? Why is there never any clarity? Why can’t I just let myself go and ‘just be’ in the moment?

The Battle with Self

There’s always something holding me back, something preventing me from realizing who I really want to be. I know who that person is. I’ve known the whole time, but I’ve never allowed myself to truly understand what that person wants. I’ve always pushed that part of myself away to meet the needs of others and to be who they want me to be.

The Mirror’s Whisper

In the process, I’ve looked at myself in the mirror and whispered, "I hate myself." It’s almost an unconscious thought that rises to the surface, living in the empty space. It’s as if saying it out loud will justify how I’m feeling. Sometimes I don’t even know I’m saying it. It’s that voice on my shoulder, always reminding me that I’m not good enough, not smart enough, not resilient enough, or extroverted enough to influence anything. I feel forgotten, ignored, or pushed aside.

The Turning Point

But I have to remember that it’s me making that happen. I’m letting people get inside my head and influence how I feel about myself. I have to stop this.

Reclaiming Joy and Purpose

I have to find a way out. I have to learn how to be me – the version of me that brings joy, not the version that lives in this seething self-hate. That person I hate doesn’t actually exist.

Becoming Whole Again

It’s time to let go of others’ expectations and finally become the person I’m meant to be. To find clarity, joy, and peace, I have to rediscover the real me.

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