When you look at someone’s career from the outside, it’s easy to imagine they followed a straight, well-marked path — one lined with perfect decisions, clear opportunities, and tidy milestones. But that’s rarely the truth.
Most of us are building our own trails as we go, and I want to talk about that honestly.
This blog series — Make Your Own Map — is a collection of the things I’ve learned while crafting a career that didn’t quite exist until I created it. It’s for people who want to work with the outdoor industry — maybe as a creative, a communicator, or a problem-solver — but who don’t know where to start. It’s for folks who are figuring it out in real time, just like I did (and still am). And it’s for anyone who’s tired of gatekeeping, buzzwords, or vague advice that feels like it doesn’t apply.
So, here we are at the trailhead. Let me tell you how I got here.
I didn’t begin in outdoor recreation, conservation, or guiding. Technically, I started in state government — working for the Teachers Retirement System of Georgia, a membership-type organization where I was in charge of member communications. I helped public school employees understand their retirement benefits, launched a social media presence, managed internal messaging, and coordinated our very structured (okay, rigid!) annual report. After a move to Colorado, I transitioned to a business association where I worked with an incredible team and even more incredible members. I got to wear a lot of hats — planning marketing strategies, managing memberships, producing and designing a magazine, writing copy, analyzing data. That’s where I fell in love with the mix: being creative and analytical, strategic and expressive. And that blend has stuck with me ever since.
But I also loved the outdoors. Hiking, camping, being in wide open spaces — they gave me the kind of clarity I didn’t always find at a desk. And over time, I realized I wanted to use my skills with the outdoor industry in some way.
When I transitioned out of my role at the association, I didn’t know exactly what I was building. But I started to piece it together, one project at a time. I leaned into what I knew: campground operators, small business owners, and membership organizations. I kept my communications skills front and center. And I started asking myself: what if I could carve out a career that allowed me to work with the people and places I care about most?
Let me be clear: I don’t have all the answers. I’m still learning about the messy stuff — taxes, finances, contracts — and trying to improve all the time. But I’ve picked up some hard-earned lessons that I wish someone had shared with me sooner:
The more specific I got — for example, working with outdoor-focused nonprofits and small businesses — the more confident and visible I became. Niching down doesn’t mean saying no to everyone else; it means showing up clearly to the people who really need what you do.
I didn’t get where I am because I applied to the right jobs. I got here because I reached out, built trust, followed up, and was honest about what I could offer. I joined Facebook groups for campground owners, reconnected with former colleagues on LinkedIn, and introduced myself as someone who understands small orgs and what they’re trying to do.
You can have the best design skills, marketing strategy, or tech tools — but if you’re not professional, timely, and clear, it won’t matter. Whether you’re pitching a project or just saying thank you, thoughtful communication opens doors.
I’m still learning things every week. And that’s okay. I’ve found that people appreciate honesty and clarity far more than perfection. What matters is showing up and being open to learning.
I’m writing this series because I know what it feels like to not know where to begin. I know how lonely it can feel to be trying to build something different — something custom, something meaningful — when most people around you don’t quite get it.
I’m also writing it because I believe in not gatekeeping. I want to share the good stuff and the hard stuff. I want you to know that building your own path is absolutely possible — and no, you don’t need a degree in outdoor rec or a massive social following to do it.
You just need a clear sense of what you care about, a willingness to connect with people, and the courage to take imperfect steps forward.
In the coming posts, I’ll be sharing more practical lessons — from how to find your niche, to the basics of forming an LLC, to building relationships without feeling awkward. I’ll talk about what’s worked, what hasn’t, and how I’ve adapted along the way.
I’ll also be offering something new: Trail Chats — short, casual 1:1 phone calls where you can ask questions or just talk through your own career ideas with someone who gets it. No gatekeeping, no judgment, no pressure. [COMING SOON!]
If you’re standing at the trailhead, unsure of what direction to take — I want you to know that’s not a failure. It’s a beginning.
You don’t need a trail that’s already been made for you. You just need a map — one that you can sketch out, rework, and add to as you go. And if I can help you draw it, I’m honored to walk a little of that path with you.
Let’s go.
Hello[at]RebeccaLeighDesigns[dot]com
