Fear. Failure. Courage to Keep Going
Tom's Kuegler path to success
Courage to:
Break Free: Imagine the stifling walls of an office closing in, the hum of monotony drowning out the whispers of your soul. Tom felt it too. He dared to listen to that inner voice, a voice yearning for adventure, for a life less ordinary. He chose the open road, the unknown path, over the safety of conformity.
Leap into the Void: With a heart full of dreams and a suitcase full of hope, he embarked on a cross-country odyssey. Picture this: endless highways stretching towards the horizon, the thrill of new experiences mingling with the uncertainty of the future. That's the leap of faith Tom took, armed with nothing but his courage and a burning desire to write his own story.
Speak Truth to Power: In a world obsessed with appearances, Tom dared to expose the cracks in the facade. He challenged fellow creators, risking their wrath and his own reputation, to reveal the truth behind their carefully curated online personas. It was a David vs. Goliath moment, a lone voice rising against the tide of manufactured authenticity.
Bare His Soul: Tom doesn't shy away from vulnerability. He invites you into his world, sharing his triumphs and failures, his hopes and fears, with raw honesty. He lays his heart on the page, creating a connection that transcends the digital divide.
Meet
, a writer who bleeds words and chases dreams.
Q: Tell us a little bit about your background:
I was born and raised in Maryland and remained there until I turned 22 years old. That’s when I started traveling.
I moved to Orlando to find work after graduation but realized soon after I hated the idea of working an office job!
It was here that I started freelancing on Upwork. I loved writing back then and still do, and my dream was to make money writing full time.
I scraped and scrounged for $200 a week for about a year, until one night when I found the website of a travel blogger called “Adventurous Kate.” She got paid to travel the world. Cue jaw dropping.
I immediately knew I wanted to be a travel blogger, too, and packed all my stuff up and took off on a road trip across the United States. Right before my trip, I snagged a $500 per week remote job, and this sustained me enough so I could pay for gas, hostels, groceries, and other things I needed.
Long story short, it was a fantastic experience, and I came home months later with so many new perspectives and stories. I started writing these stories on Medium.com.
This was in late 2016.
After a year, I had 10,000 followers there and was a contributor to the biggest publications. I started coaching people how to write better because readers would ask me so many questions about how to grow on Medium. Eventually I started making a full-time income from coaching and quit freelancing entirely.
A year later, in 2018, I went to the Philippines, and also started a travel vlog on Youtube. In September of that year, I had a video get 2,000,000 views within one week, and suddenly I became a famous vlogger in the Philippines.
I made videos there for three years and went on many adventures to many of the Philippines most beautiful islands.
After a while, though, I shut down my Youtube channel and moved to Mexico, where I met my future wife. I live here now and still coach writing to people online, while writing about my adventures on my newsletter, Finding Tom.
Q: Beyond the act of hitting "publish," what's the most courageous thing you've done as a writer on Substack?
It’s definitely been starting a newsletter with my Dad. In January 2024, he asked me if I wanted to start a newsletter with him, and I immediately accepted his proposal.
But going on this journey with him where he gets to discover this world of blogging and trolls and getting obsessed over views has been challenging sometimes.
Also, just having a public dialogue with a parent is scary, you know? I never knew what he was going to write, and I just trusted that what he wrote would be useful to people and not make anybody super angry.
I actually don’t care much about what people think personally, but I do care for his feelings. Trolls can be really hard to deal with, and it was scary to think that he might find them eventually.
In my opinion, he’s done such a great job and I plan to revive the newsletter with him very soon here. We took a short hiatus because I’ve just been so busy lately.
Q: Many people dream of writing but fear judgment or failure. What advice would you give to those who are hesitant to share their voice on Substack?
I’ve failed so many damn times, haha! I’ve written so much crappy content over the last few years. I’ve published videos that bombed or attracted endless streams of trolls. It’s part of the territory.
Give yourself time to develop. We all suck at things when we first get started, right? Writing is not a talent you’re born with, it’s a skill you develop over time with practice and education.
It’s normal to not get many views at first, so just expect it.
And if you get trolls? Well, I like to tell writers they’re doing something right if they’re getting trolls. ;)
Q: In your opinion, what's the most courageous thing a reader can do after engaging with your work?
Tell me I’m wrong in a way that’s meant to be genuinely helpful. I’m not talking about trolling or spewing anger on the screen.
I’m talking about thinking through my arguments and telling me I’m wrong with the goal being to help me see another point of view.
That’s courageous to me.
There is, however, nothing courageous about getting angry at someone online and writing hate mail to them in the comments.
Anybody with fingers and a keyboard can do that.
Q: Vulnerability is often a key component of courage. How do you balance being vulnerable with maintaining healthy boundaries as a writer in such a public space?
Yeah I mean, I talk a lot about vulnerability, but there are many thoughts I have that I would never write about in a million years. And to be fair I don’t think writers need to write about every thought they have anyway. For me I want to do two things when I write.
One, I want to explore an idea that’s interesting to me in writing.
And two, I want to be helpful to people.
If my story gets too dark, or I start oversharing, or I feel I’m making people uncomfortable, that’s not what I want to do.
I want to help the audience. And sure, sometimes you have to explore difficult subjects or stories in order to do that, but I try to keep a certain ratio of comfortable passages and uncomfortable passages in my post.
Maybe something like 80:20? If I’m making the audience uncomfortable only about 20% of the time in a particular post, I’m good with that.
You might ask ‘Tom, how do I know if I’m making the audience uncomfortable?’ I would say by paying attention to how you feel when you read your article in editing. If you’re uncomfortable, your audience probably will be too.
Most of my articles, though, I try to keep very light and easy to read. If I can do those two things I just mentioned, I throw concerns about vulnerability and boundaries out the window and just write.
Q: Courage often involves taking risks. What's the biggest risk you've taken in sharing your writing or building your Substack community?
One of the biggest risks I ever took as a creator was to call out creators in the Philippines who were purposefully making videos praising the Philippines to get more views. Guess what? I kind of did that for years myself. That was a major risk because I was telling the truth and basically calling myself out in front of tens of thousands of people.
The response I got was divided. Some thought it was a much-needed statement, and others couldn’t handle the truth and sent me nasty comments.
The video I made initially calling out creators for that is the one I’m the most proud of.
Q: If you could go back and tell your pre-Substack self one thing about the journey ahead, what would it be?
I would tell him to get on Subtack RIGHT. NOW. Substack is such a beautiful community of writers who write very intimately about their lives. You can’t find this on LinkedIn, X, Threads, or anywhere else.
When I arrived here last year, I realized quickly that these are MY PEOPLE!
Real writers! People who bleed on the page because they love it.
My only regret is that I didn’t get started sooner.
I would grab young Tom by the collar and tell him to get on Substack immediately!
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way of being, too, subscribe and reach out! He’d love to hear from you.
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Lovely partnership and I love the focus on courage.
I love Tom's story and I always learn something new from him. I'm here for the bleeding on the page too, lol.
Great stuff, Magdalena and Tom!
Thank you for featuring my story Magdalena! I'll be sure to send people to this in next week's email. :)