It was about this time last year that I started feeling particularly sick of my day job. I was working at an outdoor gear shop most days, and guiding outdoor trips through their service, usually one or two per week. Getting outside was awesome, but the retail work was draining and every day felt like it dragged on. It’s not that the work was hard or that my coworkers were bad — it wasn’t and they weren’t — but it felt like a slog. I felt trapped, like a jaguar in a zoo enclosure, endlessly pacing my usual path around the store waiting for 5pm to finally get there.
So, it’s no wonder that I daydreamed, every day, about how I would move on from that job.
I turned to what I did enjoy doing: the outdoor guiding. Could I just do it myself? Theoretically, sure! I did earn a degree in outdoor education, after all. And I spent five years planning, budgeting, marketing, and executing activities as a camp director for the Boy Scouts. And I’d spent three years managing a large portion of the operations of my current employer’s guide service.
I knew I could do the work. But could I make it work? There would be benefits aplenty: flexibility to control my schedule, the latitude to try new ideas without having to ask permission from a boss, and, hopefully, a bigger paycheck as I wouldn’t be giving over half of it to the guide service. But for every benefit, there would also be risks: getting enough clients, managing the insurance and liability myself, making the significant investment of purchasing gear for clients to use, and entering a well-established market as a newcomer. Still, I obsessed.
My desire to build my own business stemmed from more than simply wanting those benefits. I thought I could make a real difference. I could be nimble and meet needs that long-established guide services might feel too constrained to. I could offer regular clinics to be of service to locals, in addition to transient tourists. I have years of experience and enjoy working with young kids, another group that I think is underserved. Without kids of my own, I have few other obligations and can be available for longer overnight trips. It’d be good on both sides! I would offer personal, professional, and fun-focused hiking/camping/skiing/paddling/climbing trips in the Adirondacks.
After a couple of months of feeling more and more trapped, becoming ever more convinced that opening my own guide service was the only way out, I finally told my wife how I was feeling. She had noticed my discontent and to my great relief and surprise — though I really shouldn’t have been surprised — she was on board. I regaled her with all the ideas and plans for the business that I had been scheming in my head. She was impressed. We agreed that I shouldn’t rush into anything, or out of my current job, but she had faith that I could run a successful business. We both wanted those benefits that would come with opening a small business and thought it’d be worth the risk. It would be a leap of faith — for her in me, and me in myself.
Not long after our discussion, on February 29th, I saw this post from Seth Godin. I had found my yearly theme: Leap Year.
After that, going back to work immediately felt so much better. I was no longer trapped, no, I was simply biding my time to make my big move. True to my word, I took things slow. Over the next few months, I started looking into insurance and working up a liability waiver. I attended a conference for New York State Outdoor Guides and took careful notes from guides who had started successful businesses. I brainstormed how I would differentiate myself from the crowded market (I think drop-in group events are a missed opportunity around here). I started reaching out to the large gear brands to better budget for wholesale equipment costs. I set a tentative date of June 1st for when I wanted to kick things off.
The summer came and went.
Working through a risk management plan and liability waiver ended up taking longer and costing more than I initially expected. But they were critical pieces of the puzzle. I was able to save some by being a guinea pig in a new program offered by an outdoor law group. Finally, the legal stuff was done.
I applied for an LLC, which was easier, more intimidating, and more antiquated (I had to publish notices in two local, physical newspapers) than I anticipated. The business officially existed, even if I wasn’t ready to start taking on clients yet.
I worked on a website, which was both fun as a creative endeavor and frustrating as I found that my old quibbles with Squarespace had not been resolved in the intervening years. I debating pricing structure with my wife. I scoured my photo library for good images from my outdoor adventures. I went through multiple rounds of edits on my (too long) wording to make it easily digestible by potential clients. Finally, the website was done.
And then, the doubt set in. I had chosen a name for the business long ago. One that I thought would perfectly encompass all my long-term grand plans. But, as I came to realize, it could be confusing and niche to use as the name of an all-purpose guide service. I brought up my doubts to my wife, and she agreed. The name had to change and now was the time before I built any recognition with the old one. I pitched her a few ideas I’d been tossing around, but none sounded right to her. Then she, in one try, came up with absolutely the right one: Onward Mountain Guides.
It conveys the right feeling that I’ll help clients forward/skyward/on toward their goals. It incorporates “mountain guides”, which is important for showing up for people searching for guides in the Adirondack mountains. And, best of all, it has a bit of whimsy as it abbreviates down to “OMG”, which you can bet I take advantage of for marketing. The domains onwardmountainguides.com and onwardguides.com were available, as was the @onwardguides handle on Instagram. The decision was made. I would be Onward Mountain Guides.
But that opened a whole new headache as I had already opened the LLC and bank account under the old name, and built my entire website around it as well. My only solace was that I hadn’t yet printed business cards or other physical materials that would need to be scrapped. Figuring out the name change took weeks of work, and it’s still not yet completely resolved. But it was worth it.
I “quit” my job at the end of October. I say that in quotes because I still, technically, work for my old boss. When I told him that I was ready to try my own thing, I told him that I would like to continue to be available as a freelance guide as needed, even if I was stepping back from my work in the retail shop. He took the news well, wished me the best of luck, and agreed that it would be good to continue to have me available to guide trips for them. In fact, I’ve reached out to almost all the guide services in the area to offer freelance support in case they get double-booked or just need an extra hand around. I think that will help fill my time as I work to attract my own client base.
Suddenly, I was free. Free to make my own schedule. If I didn’t have a client, I could still make the time useful by scouting out new hikes and climbs, and working on my personal skills. But also free of a regular paycheck. I’m very fortunate to have a wife who (1) has a job that can float our essential expenses for a little while, and (2) is supportive of me taking this leap while she shoulders that responsibility.
To provide a little financial security from my end, and to further service my overall goals of spending more time outside and honing my technical skills, I applied to work as a ski instructor at the local ski resort. I got the job and committed to working at least a couple of days per week there. However, I could still have the flexibility to choose when I wanted to work there and could make adjustments if I secured client trips.
My first client trips as Onward Mountain Guides were in early November, and they all went great. I hiked High Peaks with folks working on summiting all 46 of them. All of my clients so far have booked multiple trips with me — a truly great feeling to know that I made a positive impression. I’ve started getting reviews, too, that makes me blush as I publish them to my homepage.
Reaching out to the guide services and other local businesses has been working out so far too. Everyone has been very kind and receptive to having an extra person to call if needed, and a couple of spots were actively looking for a go-to guide for the winter months (and maybe longer). I’ve ended up with many promising irons in the fire, just waiting to be pulled out and hammered true.
Between adventuring with my own clients, working as a ski instructor, and spending the rest of my time working on marketing and equipment orders, the last couple of months have flown by. I’m having so much fun — even while I work to balance the new stress of erratic paychecks and knowing I’ve invested a lot of personal funds into starting the business that I certainly want to get paid back.
Everyone I spoke to warned me that by working as a guide in the Adirondacks, it would be nearly impossible to make a real living. The clientele and weather would be too inconsistent. They might be right if playing by the old rules. But I think there’s untapped potential here to be a valuable member of the guiding community, not only for my own service but by being available anywhere that wants to hire a guide. There are schools and local youth groups that want to get outside under the supervision and expertise of a licensed and insured service. There are climbers and hikers who want to work through a progression of skills, crags, and peaks over the long term — with a personal relationship with their guide instead of rolling the dice on who will meet them at the trailhead.
I may not be totally unique in being able to offer those services, but I am ready and willing to do it right now. I’ve leaped onward.
Journal
