Six Months In: your hiking company
If there were ever a strategic time to become an official small business owner — an insured, licensed, legitimate Professional Outdoor Educator™ — I’m pretty sure it wouldn’t be the same year:
- I moved across an entire continent
- I landed in the nation’s capital during the worst political and economic moment my generation has seen
- I became an empty nester. Not just a regular empty nester; but after raising SO. MANY. KIDS. SO. CLOSE. IN. AGE. andthentheyallmoveoutatthesametime! What in the actual fuck. Hey. Kids. Get back here.
- I entered the “hurtling toward middle-age while every woman my age screams into the void about peri-menopause” era
- I am barely learning to deal with a cancer diagnosis and oncology appointments
- I dove head-first into trauma therapy and started facing demons that were never mine to bear, since, you know, the kids are all gone, why not?
But here we are.
At some point in the middle of the chaos, Barbarian Scientist and I made an agreement—probably at the exact wrong moment and for the exact right reasons—that once we moved here, I would finally do it. I would stop dreaming about being a professional outdoor educator and actually become one.
And as we neared our one-year anniversary in the DMV, I realized:
If I didn’t leap now, I never would.
So, I resigned from my okay-marketing job with the less-than-okay salary and even-less-than-okay commute. I filed the paperwork. I paid the fees. I became a legal entity.
And let me tell you:
It felt like reaching the capital-F False Summit of all false summits.
What I am Good At (and What I am Bad At)
I am very good at:
- connecting people to one another and to resources
- teaching conservation and Leave No Trace
- building outdoor skills and helping people train for big goals
- crafting itineraries that will wreck you and heal you
- guiding people into wilderness experiences that change their lives
I am very bad at:
- making money
- math
- charging what things actually cost
- math
- acknowledging that transaction fees and taxes exist
- acknowledging math
- math
I should mention math again.
Because friends, I am losing money on some of my 2026 trips. And when you’re under oncology care, your partner is working three jobs, and, um, when you are a human being in this disgusting capitalist society, losing money is… not ideal.
And somehow, despite all that, it does not mean I’m bad at finances.
I raised my kids without debt and still live that way as much as possible—partly out of principle, partly because keeping life debt-free keeps the math as simple as humanly possible (you’re welcome, brain – now pay me back by creating some of that serotonin the kids keep talking about).
I’ve been doing this for free for a long, long time
For years, long before I had a business license or insurance or a tax ID number, I was crafting dreamy, once-in-a-lifetime adventures for friends and groups—multi-day backpacking trips to remote Oregon hot springs, 64-mile shoulder-season thru-hikes from Idaho into Washington, sunrise summit pushes, waterfall circuits, national park marathons.
I did it all for free because I genuinely believe that we are better people inside when we experience life outside.
But then something started to happen:
I watched people build full-time incomes from the exact kind of experiences I was giving away. Some were even people who learned from me—people who had been on my trips or borrowed my planning templates or asked my advice as they built their own offerings. People who did not have my education, training, certifications, or experience.
And that stirred some feelings.
I’ve never had a particularly “winning-est” personality. I’m not curated. I’m not shiny. I’m not a natural salesperson. I am better at creating connections FOR people than I am at connecting WITH people. So I convinced myself that the only way I could inspire people to explore the wilderness was by underselling myself—my time, my labor, my expertise—because then no one could accuse me of being too much or wanting too much.
And honestly? It was easy to hide behind the noble excuse that I didn’t want money to be a barrier for people to experience wild places. That is true—reality can go straight to hell for making nature inaccessible.
But the unspoken truth was this:
As long as I made sure everyone heard only the altruistic part, we didn’t have to discuss the tender, scared parts of me that doubted I was worth charging anything at all.
Or something like that.
As If I Had Not Learned Enough Hard Lessons
This brings us back to Six Months of Being Official™, where I’ve had to confront all of it head-on.
- Transaction fees?
- Taxes?
- Overhead?
- Pricing models
- Cancellation policies
- Market rates?
- AND I am expected to put value on the time I am working? Fam. Stop.
Every time I look at the spreadsheets (well—Barbarian Scientist looks at the spreadsheets, I stare at them like they’re written in Elvish), my brain hits a wall.
I want people to see these places. I want them to have these experiences. And my soul panics:
What if they can’t afford it? Should I lower the price? Should I lower it again? Should I pay the difference? Should I just hand out money on the trail? I should probably just hand out money on the trail.
This is really what the process looks like:
- I make a note in my phone of an idea for a trip
- When I have time, I sit at a computer and begin working it out
- Then, if it sticks, I become obsessed
- Everything in life stops other than what I have to do until I have created at least 102 versions that I hate of the plan because I-literally-want-you-to-have-the-absolute-best-experience-that-a-person-can-possibly-have-and-how-could-I-possibly-think-I-of-all-people-could-provide-that-for-someone-as-wonderful-as-you?
- I decide I suck at this and at everything I have ever tried
- I do not talk to anyone at all for at least 2 days – 2 weeks
- I go on a hike
- Then I ask someone if they would please look over a draft of it
- They rave about the itinerary
- I build the cost analysis
- Repeat steps 4-8, but now with MATH, and instead of “someone” looking it over after I hike, it is Barbarian Scientist
- I scurry to my favorite corner of the sofa, with my frog habitat on one side of me, my dog on the other, my heating pad beneath me, 62 blankets on top of me, and a hot drink, a cold drink, a sweet drink, a neutral drink, a caffeinated drink, and at least one of those has a handle and a lid, like any neurotypical person, and act like whatever he is looking at on the computer screen is what a completely normal person would have passed on to him to review, not just completely redo.
- And then… And then a few minutes later, he slowly turns around the first time (this happens many times). He says, “TeddiJo. Do you know that the point of creating a business is to generate an income?”
- I am pretty sure you can imagine the rest.
Some hard-learned lessons:
- Transaction fees are astronomical. Why? WHY. Why does it cost a percentage of every dollar AND THEN ALSO ANOTHER FEE FOR PROCESSING THAT? I already paid you A LOT of money to just use your platform!
- If you don’t include transaction fees in pricing, you (business owner) pay them. And yes, I did not know this until after most of the trips were posted, so yes, I am paying the fees.
- If you don’t include taxes in pricing, you (business owner) pay those too. Yep, I got those, too.
- If you don’t know what you don’t know, you will find out later—invoiced
And this is just what we know so far.
It has only been six months.
So yes, 2026 will be a financial loss.
And yes, that is my fault.
And yes, that is hard to sit with.
At the Same Time, Something Beautiful Happened
Right when I was wondering if I’d made the biggest, boldest, most unhinged mistake of my life…
I received an offer to build and teach outdoor education at the second-largest community college in the U.S. in its inaugural year. I am the only Outdoor Educator and the curriculum is of my own making. It is an enormous honor.
It has been wild.
It has been beautiful.
It has been heavy office work.
And it has been some of the most meaningful outdoor time I’ve ever had.
My students?
Most are recent immigrants, and many are adults having their very first wilderness experiences with me. I’m teaching people how to poop in the woods (a surprisingly empowering topic, I assure you). I’m teaching people from historically oppressed countries that they can literally climb mountains and still honor their religion, culture, family responsibilities, and that climbing these literal mountains often helps us climb our metaphorical mountains at home. Every week they bring me new stories where they are producing evidence of this truth. I’m teaching people that even when they are feeling vulnerable or uncertain, or when they are not the person in charge, they are just as valuable to the community, that they are wanted, and needed.
It’s humbling.
It’s sacred.
And it requires strict boundaries, because I could very easily give every ounce of myself to the college and have nothing left for the business I’m trying to build. I mean…there is no math here, family. Just love.
The tough part about a role like this is that there is not telling what the future holds. Will my contract be renewed? Will I have a job next year? Will I get a larger budget? Staff? The uncertainty ensures I cherish my time with my students even more.
Here’s What’s Coming
MERCH:
I have an enormous goal to finally put out some branded things – at least shirts and stickers – soon.
COACHING:
I am working on some training manuals to publish as PDFs (sigh…to sell…for money) and am otherwise going to limit what I offer for coaching to focus on select endurance events and the individuals who are signed up for my trips.
YOGA:
I’m burned out on teaching yoga.
Does that mean I am doing it wrong?
Yoga will remain part of my brand—but only in special, intentional ways. Meanwhile, I need to be a part of a class more often than I am teaching a class, for at least awhile.
2026 INTERNATIONAL WOMEN’S DAY
I am hoping to add an International Women’s Day 3-day weekend to the menu, but I am not sure I have the bandwidth to pull together something I would love to share. If you are reading this and would want to collab – reach out!
2026 CO-ED TRIP
I am considering having an annual co-ed trip, and the 2026 trip would be New River Gorge. Once there is a firm decision on that, it will be listed clearly on the checkout page.
BOOK CLUB:
I am keeping my free, low-pressure book club—a cozy little corner of this adventure business where we slow down, read good things, and talk about them with good people. Here are he books I selected for 2026, each chosen to challenge us, inspire us, or help us reconnect with the natural world (and ourselves). Registration will be through Eventbrite, and I’ll post the link here on the website and across social media so it’s easy to find. We’ll meet on Zoom with zero expectations—come as you are, whether you read every page or skimmed the vibes. After each session, I’ll share my notes and the LM Notebook video right here so anyone can use them for their own reflection or even host your own book clubs down the line. Think of it as a little trail rest stop in the middle of everything else we’re climbing.
2027
January 2027 launches in 6 weeks (eeeeee!)
I will allegedly learn how to do small business taxes…seems rude, tbh (send help)
2027 TRIPS I AM WORKING ON:
- Costa Rica Hiking & Yoga Retreat
- Banff 2.0 with a Revelstoke National Park add-on
- Mount Rainier National Park: hiking to each of the lookout towers + (optional?) backpacking
- Rocky Mountain National Park + Manitou Incline (possibly co-ed)
- Grand Canyon Rim-to-Rim backpacking…or do we want to do it in 24hours?!
- I am still stuck on taking y’all to Las Vegas to show you the epic hiking and rock climbing there
- …and that is just the beginning of the list
Closing Thoughts (For Now)
I wanted to write a triumphant “look at me go!” post after six months as a business owner.
Instead, here is the truth:
It has been humbling, messy, really expensive, exhausting, sacred, and transformative.
I am not where I hoped I would be— uhhhh… that’s it. Nothing inspirational. I am not where I hoped I would be.
I hope my transparency helps someone. I hope if you are reading this, wondering if you can chase a dream, I hope you decide you can. You might end up pretty broke. And broken. But, you might end up that way anyway. Actually, you probably will end up that way anyway, so you may as well do it while chasing that dream. ✨
