The Top Secret to a Creative Career


It’s been a busy summer with events in New York City, Atlanta, Las Vegas, Anaheim, back to Las Vegas, and then Salt Lake City. During and after writing “Backpack, Pen and Passport: Build a Freelance Writing Career to Travel the World I obsessed over asking successful creators at these events — from writers and filmmakers to YouTube personalities — how they got started, how to become a travel writer. Some have a steady stream of work on their own terms, others have millions of fans who hang on to their every word, but all of them had to build it from scratch.

And invariably, the answer was some version of, “Well… I just started.”

Most have complex, exciting operations filled with clients and travel, but it didn’t begin that way. Almost all of them had absolutely nothing but an idea.


As they worked over that idea, they had questions. Will anyone take me seriously? How will I find people interested in what I’m doing? Will anyone care at all? If they do, will they actually pay me for it? And if so, how much? Whether it was writing or video, they had serious doubts — and they tended to alleviate those doubts by immersing themselves in planning.


Lots and lots of planning. They obsessed over every little detail of their work, from the topic to the language to the style. The put hours into thinking about their first piece before firing up a computer or hitting the record button. They wanted to make sure their debut was perfect.


Then they put it out — and they realized that almost everything they’d planned turned out to be wrong.


Sometimes the things they thought mattered most just didn’t resonate with people, and what seemed unimportant turned out to be a highlight. As comments and feedback trickled in, they found that what their audience seized on and cared about didn’t always match what they as creators cared about. Not much of that planning actually made a difference.


For their next piece or video, they combined that feedback with their creative vision and made something a little closer to what to what made them happy and what people wanted to read or watch. They repeated this process, and a few projects in, they tended to have something radically different from their original plan.


This isn’t to suggest that embarking on a successful, flexible creative career that allows for travel means you should shoot from the hip. You want to develop your idea a little bit, think about how best to do it, and then get going.


That’s the secret all these creators revealed: they just started. No matter how much they’d planned and prepared, they ended up in a different place than they’d anticipated. Some surprised themselves with enjoying topics or styles they’d never before had an interest in, while the people actually looking at their material showed them that they had real talent in an area they’d never even thought about. They evolved.


If you want to be a novelist writing in a farmhouse in lush County Cork, you wouldn’t think, “I won’t write a sentence until I feel like I can write the next bestseller — then I’ll start.” If your dream is to work directly with CEOs on creating marketing material for Fortune 500 companies, it would be insane to wait for a massive opportunity and pass on helping small businesses as you developed your craft. Babies don’t remain silent until they can perform Hamlet’s soliloquy, and they don’t sit on the ground until they can run like Usain Bolt. In short, it just doesn’t work that way.


The writers and creators I spoke to offered four pieces of advice that outlines how it does work:



  • Don’t think too hard. Not only will the natural progression of your creative work take you to new, unforeseen places, but quite a bit of all that planning will be wrong anyway. Think a little bit, try it out, and go from there.
  • Who cares if you fail? Think of it this way — if you start and don’t get the response you hoped for, who are you disappointing? Your zero clients? Your zero fans? You’ve got nothing to lose, and every time you do a project you’ll gain insight into what will work better next time.
  • Be flexible. Be honest with yourself about what you enjoy or don’t enjoy once you start creating, then adjust. Take feedback seriously — put yourself in a reader’s or viewer’s shoes and be willing to entertain their suggestions. A top YouTube creator I spoke with is a respected source in science/tech, but his first batch of videos were all comedy. He liked research and presenting information, and people enjoyed him in that role. Once he made the switch, his career took off.
  • Really, just start. This is the big one — no matter what creative endeavor will unlock a career teeming with travel and fulfillment, you need to get the ball rolling. Write an article or record a vlog and put it out there. It won’t be perfect, but it doesn’t need to be. It just needs to happen.

You’ve got an idea of what you want to do, and you’re probably thinking about where in the world you’ll do it. So… get started. It really is that simple.


“Matthew Tabor is the CEO of the writing and marketing firm Koala Fight Media and is co-founder of the YouTube business development company Woven Gem.”

You can read Matthew’s book here “Backpack, Pen and Passport: Build a Freelance Writing Career to Travel the World”.