The biggest lessons I learned while starting a travel writing business

Like many 30-somethings, I’ve spent at least half of my life in a classroom—yet at no stage have I learned more than starting my dream writing business.  

I adopted travel writing as a side hustle to my nine-to-five communications job in 2016. I took the leap into full-time writing and photography(opens in a new tab) in 2018. The rest, as they say, is history—but it’s a history I reflect on frequently because I’ve learned countless lessons along the way. 

Starting any new business, especially in a saturated market like travel writing, can feel daunting. Competition’s high. Rejection’s the norm. And the media landscape is ever-changing. Even so, I’m proof that ordinary people like me, a writer with limited past journalism experience and no industry connections, can break in and earn a good living (a living that exceeds the salary of my previous senior-level nine-to-five role).  

Here are the most important lessons I’ve learned going from the seed of a side-hustle idea to running my own business. While my experience centers on travel writing and photography, these tips are universal. 

Hire a coach

My business has grown a lot over the past six years, and the most pivotal moves always come when I invest in coaching. I hired my first coach, Rebecca L. Weber(opens in a new tab), in 2019. She helped me set a business strategy and hone my craft in ways free webinars and podcasts never could. I then hired my second coach, Jenni Gritters(opens in a new tab), late last year when I needed to figure out how to level up and navigate an exciting new stage of my business—something free resources, yet again, just didn’t support.

Why is coaching key? For one, coaches bring a third-party perspective. Business owners are often too close to the day-to-day. Coaches lend a new way of thinking; the right ones are also trained to help you see and navigate this new perspective for yourself. My best advice for hiring the right coach: absorb their online content. I listened to both of my coaches’ podcasts before hiring them; this helped me confirm they were the right fit.

I paid for this coaching by picking up a handful of extra freelance assignments to offset the cost. I knew it would be a major investment, but I also knew that without expert help, I’d stay exactly where I was. By fine-tuning my business, and helping me brainstorm smart new ways to move forward, both coaching investments paid for themselves within roughly six months.

Find your expanders

There are three categories of people in your life when you embark on a side hustle or new business: those who are ambivalent, those who say “it’ll never work,” and those who support you full force—and push you to be your best and stay inspired along the way. Find the latter.

These pump-up friends, known in the manifestation world as “expanders,” will help you grow exponentially. For me, it’s a handful of creative and writing friends. One group, in particular, meets virtually every month to share wins, losses, and career dreams; we help each other through it all—leaving each call ready to take on the world.  

Build your business

In the first few years of my business, I took every piece of advice to heart. Scale up? Heck yes! Outsource? Let’s do it! These buzzwords, the refrain of countless TED talks and podcasts, became my goalposts for success. Then something felt off. That wasn’t my version of success. I was building my business to be “successful” in the eyes of industry thought leaders—not my own.

After much introspection, I’ve realized my definition of success means living a fun, adventurous life with a career spent creatively telling stories I care about. Sure, money’s part of that, but it’s more a pillar to support the life I want to lead, not money for the sake of money. I don’t want to “scale up” and have the coveted “10x growth.” I want to travel the world, meet new people, and make action-packed memories.

Now, I choose my business decisions based on that true-to-me goal. I outsource when it supports my path, not because a well-known podcaster told me to. I’ll push for 10x growth if and when I want to—but at this point, I’m entirely fine with my own version of scaling up: pursuing bigger adventures that push me outside my comfort zone.

Tough feedback? Sleep on it.

Feedback has been integral to the evolution of my business, but that doesn’t mean I love receiving it. I still cringe whenever I open a Word document covered in tracked changes. I know the edits and constructive criticism will help me improve; they almost always do.

That’s why I take a beat to read, review, and reflect on the notes, then close the document and take some space before tackling next steps. When time allows, I wait until the next day. Almost every time I do that, I wake up refreshed and approach the update or edit process as a learning experience. The space to absorb criticism helps me put things in perspective. Even if I don’t have time for a full night’s sleep, I’ll at least take a walk to get some fresh air so I can embrace the growth process instead of loathing it.

Find your intuition—then follow it

If there’s one thing I attribute my own business sustainability to, it’s intuition. In fact, I now make almost every decision based on what my gut tells me is right. Every time, my intuition’s right. (Every time I don’t follow it, I suffer.) It took me several years to get to this point of intuition following—not because I didn’t trust it. I didn’t know how to find it.

With content and distractions galore, it’s easy for your intuition to become muted. If you put your phone away and journal about a big decision, or take time to walk around the block and ponder it (sans Spotify or podcasts), your intuition will almost always speak up and point you in the right direction. That’s why I journal every day; my notebook is the platform for my intuition to speak up. It guides my decisions and helps me know the next right move—the move that works best for me and my personal goals in this one wild and precious life.