Finding Clarity Through the Fog of Doubt

“I am not a writer. I’ve been fooling myself and other people.” — John Steinbeck

I’ve started and archived a handful of blogs over the years.

In 2010, after a year of backpacking in South America, I moved to Mexico City to chase my dream of becoming a travel writer. 

I was obsessed with the PBS show, Globe Trekker, but making videos of my own seemed out of reach at the time. Instead, I wanted to write for print magazines and guidebooks.

But print was already on its way out, and everything was moving online. My focus shifted along with it.

I started a blog to promote my work and began networking with other travel bloggers. This opened doors to freelance opportunities, a writing project with the tourism board, and an ambassador role promoting travel to Mexico. 

Everything seemed to be falling into place ― but with each new opportunity came a nagging sense of self-doubt.

I found myself wondering, Who am I to write about this? The thought kept looping in my head. I wasn’t an expert. I was still figuring things out. What if people saw right through me? 

Behind the Mask

The ambassador program ended a year later and I moved to Playa del Carmen, then Cancun. 

I loved what I was doing, but I couldn’t shake the feeling that I wasn’t enough or that I didn’t belong. It was like I was constantly questioning whether I had earned my place. So, when a full-time content developer role came up, I saw it as a way to gain the professional credibility I felt I was missing.

I spent the next four years working in an office in downtown Cancun writing editorial content and sales copy for an online booking site. It was a solid job, but eventually, the six-day workweek (yes, really!) wore me down, and I started looking for something with more flexibility.

I moved on to a part-time content manager role for a small, family-owned real estate company, which allowed me to work remotely. During this time, I also took on contract work for a few other travel booking sites and started another blog that never really took off. 

Fast forward to 2020, and I was back in Philly about to start a full-time SEO analyst role when the pandemic hit, and the offer was rescinded. I’ve been freelancing ever since.

Over the years, I’ve watched some of the bloggers who started around the same time as me become very successful. Some of them I’ve followed for over a decade now. 

It’s wild to think what could have been if I’d been able to get myself in the right headspace, but back then I didn’t understand what I was up against.

Imposter syndrome is one of the biggest roadblocks for solo creators. It creeps in when we start something new, step outside our comfort zone, or put our work out into the world. It convinces us that we’re not good enough, that we don’t belong, that we’ll be exposed as a fraud.

But here’s the truth: Almost everyone who has found success doing work they care deeply about has felt this way. The difference is, they kept going anyway.

The Echo of Doubt

Imposter syndrome isn’t just self-doubt ― it’s the persistent feeling that you’re not as competent as people think you are, despite evidence of your skills or success.

It’s the voice in your head that whispers:

• “I just got lucky.”

• “I don’t actually know what I’m doing.”

• “Eventually, people will realize I have no idea what I’m talking about.”

It’s especially common when you’re starting a new business or stepping into a new industry. When you’re charting your own path ― without a boss, a clear roadmap, or external validation ― it’s easy to feel like you don’t measure up.

But what many don’t realize is that imposter syndrome often has deeper roots.

For many of us, it’s shaped by early experiences, especially those from childhood, where we were told, directly or indirectly, that our thoughts, feelings, or creativity weren’t valuable.

These early messages are deeply ingrained, and it can feel like our nervous systems are constantly on high alert, interpreting every new challenge or opportunity as a test of our worth.

The inability to show up as our true selves, for fear of rejection or criticism, often fuels the voice of imposter syndrome. We internalize these early lessons and carry them into adulthood, where they continue to shape how we approach our work and creative projects.

It becomes a cycle that feels nearly impossible to break. But here’s the key: recognizing where these feelings come from is the first step toward letting go of them.

And here’s the paradox: The more you learn, the more aware you become of what you don’t know. That’s why imposter syndrome often hits hardest when you’re actually making progress. 

Instead of a sign that you should stop, it’s often proof that you’re growing.

Now that I understand imposter syndrome for what it is, I’m moving forward with a clearer perspective, knowing that setbacks and pauses aren’t failures ― they’re simply part of the journey.

Letting Go of the Lie

If you’re waiting for the day imposter syndrome disappears, you might be waiting forever. The truth is, it never fully goes away ― you just get better at moving forward despite it.

Instead of seeing it as a problem, recognize it as a sign of growth. It means you’re operating at your edge, stretching beyond what’s comfortable, and growing into the person you’re becoming. 

The key isn’t to eliminate it but to learn how to work with it. Here’s how:

• Reframe self-doubt. Instead of “I’m not good enough,” try “I’m in the process of improving.” Progress is the goal ― not perfection.

• Take action despite the doubt. Confidence isn’t a prerequisite for putting yourself out there. It’s a result of showing up, over and over again.

• Look at the facts. Make a list of your wins ― big or small. Revisit it whenever imposter syndrome creeps in.

• Surround yourself with proof. Join communities, connect with other creators, and remember: You’re not alone in this.

Confidence isn’t built by waiting until you feel ready. It’s built by taking action, proving to yourself that you can figure things out as you go. Every step forward is proof that you belong, even when doubt tries to convince you otherwise. 

Imposter syndrome still shows up for me from time to time. Some days, that voice creeps in ― but now I recognize it for what it is: a signal that I’m stretching beyond what’s familiar.

And when that stretch starts to feel like too much, I’ve learned it’s okay to pause. Sometimes, stepping back is exactly what we need to stay grounded. Slow growth is sustainable. It lets us move forward at a pace that honors both our energy and our vision, even when doubt is along for the ride.

So, the next time you hear that voice whisper, Who are you to do this? ― answer it with action. Keep showing up, keep learning, and keep going. Because the only way to fail is to quit.

That’s all for this one.

I hope it helped.

TLDR: Imposter syndrome never fully fades ― work through it, not against it.

Dispatches from the Edge of What’s Next

"How we spend our days is, of course, how we spend our lives." – Annie Dillard

For years, I struggled with the idea of traditional work. 

The 9-to-5 grind never seemed to align with the kind of life I wanted ― a life where freedom, creativity, and personal growth were central to everything I did.

When I was in my 20s, I read three books that fundamentally reshaped the way I thought about how we choose to spend our time: Vagabonding by Rolf Potts, The 4-Hour Workweek by Tim Ferriss, and Your Money or Your Life by Joseph R. Dominguez and Vicki Robin. 

These writers challenged me to question the status quo and reevaluate what meaningful work could look like. They helped me see that fulfillment doesn’t always come from climbing corporate ladders or following predefined goals, but from building a life rooted in purpose and passion.

Their ideas planted the seed of possibility, showing me that it was okay ― even necessary ― to carve out a path that wasn’t conventional if I wanted to live in an authentic, fulfilling way.

I’ve leaned into these ideas over the years, balancing part-time roles and freelance gigs with long-term travel while prioritizing time freedom. But the dream of starting a business and earning a living solely from my creative work has always been there, and now, I finally feel ready to make it happen.

Thinking Out Loud (on Purpose)

As I step more fully into this next chapter, I’ve been reflecting on the broader shifts happening in our society. The way we work is changing. Traditional jobs and business models are no longer the only paths to success. Instead, we’re seeing a shift toward independent digital work and the creator economy.

More and more of us are embracing the flexibility and autonomy of being freelancers, creators, and solopreneurs. We now have the power to forge our own paths, whether it’s through content creation, offering niche services, or starting a one-person business.

But for many Gen X creatives, the shift toward independent work isn’t optional. Traditional creative roles are disappearing, increasingly replaced by automation or absorbed into algorithm-driven platforms.

Faced with fewer conventional opportunities, we're adapting to survive, to stay relevant, and to keep creating in a world where AI is rapidly reshaping traditional jobs.

This evolution is at the heart of Higher Trail.

Social media, for all its power to connect and inspire, often moves too fast, prioritizing quick takes and fleeting moments over real reflection. Here, I want to explore the ideas that matter, free from the constant churn of algorithms and the race for engagement.

This blog will focus on three core areas that drive my curiosity and fuel my creativity:

👉 WORKLIFE

Worklife is all about empowering creators and solopreneurs to thrive in today’s evolving work landscape. With AI as an ally, not a replacement, solopreneurs have the ability to work smarter, unlock creativity, and build ventures that reflect their values.

But this shift isn’t just about quitting your job or becoming your own boss. It’s about embracing a mindset that prioritizes autonomy, creativity, and connection.

It’s about doing work that aligns with who we are and what we value most.

By stepping away from the constraints of conventional employment, we unlock the freedom to be more creative, the chance to directly impact a niche market, and the ability to build something sustainable ― all on our own terms.

The future belongs to those willing to adapt, innovate, and lean into what’s possible.

👉 TRAILS

Trails celebrates Pennsylvania’s breathtaking landscapes with scenic hikes and outdoor adventures. From peaceful forested paths to adrenaline-pumping ridge runs, this pillar highlights PA’s diverse trail offerings, bringing them to life through immersive storytelling and creative content formats.

Ultrarunning has started to take up more space in my life ― not just as a personal challenge, but as a gateway into a tight-knit, inspiring community.

I want to use this space to explore what it takes to get started, what makes these events so magnetic, and how newcomers can find their place at a local race or group run.

Whether you’re an experienced ultrarunner or just curious about this corner of the outdoor world, there’s something special about the rhythm of moving through nature on foot ― and the people who show up to do it together.

This is where passion, place, and community meet and I’m excited to keep exploring it.

👉 PROFILES

Profiles will spotlight local creators, solopreneurs, and bold thinkers who are forging their own paths. These are people who’ve taken the leap ― trading predictability for purpose ― and built ventures rooted in passion, skill, and personal values.

Together, we’ll explore the diverse paths one-person businesses can take, from niche content creators to small business owners and everything in between. And who knows… some of these conversations might even make their way onto a podcast soon.

These stories will serve as inspiration for anyone wanting to pursue a similar path, showing that success doesn’t have to follow a traditional blueprint. Instead, it’s fueled by clarity, creativity, and the courage to build something that’s entirely your own.

Through these themes of Worklife, Trails, and Profiles, I’ll explore the intersection of two growing trends: the booming interest in outdoor recreation and the rise of one-person businesses ― and what it means to build a life at the crossroads of both.

Work, Wild & Free

But what does it really mean to build something meaningful on your own terms? For solo creators, the answer lies in the steps we take and the freedom we claim along the way.

Being a solo creator means forging a path that’s entirely your own ― and with each step, you’re building something that reflects your values, vision, and voice.

The path won’t always be smooth, especially for those of us who didn’t grow up in this digital-first world. For Gen X creatives, this era demands reinvention. Many of the traditional roles we trained for have disappeared or been reshaped by AI, leaving us to carve out entirely new lanes.

But that’s also where the opportunity lies.

We’re not just adapting to change ― we’re actively reshaping the future of work. And for those of us blending purpose, creativity, and a love for the outdoors, the future of work looks wild and free.

That’s all for this one.

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TLDR: Work is evolving ― carve a path that fits your life, not the system.