My longing to be a real backpacker started about 7 years ago when I read Wild. Cheryl Strayed’s story of walking onto the Pacific Crest Trail as a spiritual journey spoke to my soul.

Coincidentally, I read this book right when I had made the leap from side-hustle designer to full-time freelancer. I, too, had ventured out into the wild and felt equally unprepared for what laid ahead. I, too, could not imagine the twists and turns and lessons I would learn over the next several years.

For the next 5 years I would quietly watch other women’s adventures on trail blogs and in Facebook groups. I would watch YouTube videos on gear, and I confided to my closest pals that I would, one day, backpack. 

At the same time, I quietly built a business, expanded from freelancer to agency builder. I connected with other business owners online, watched YouTube videos on how to do everything from build spreadsheets to write code. 

Then, one perfectly gorgeous spring evening on the soccer field, one of said closest pals pulled up a chair beside me and tossed a book in my lap. “I’m calling your bluff on this backpacking stuff.” I looked down confused. It was a beginner’s guide to the Appalachian Trail. 

Lesson 1: Get yourself some pals who will call your bluff on big, audacious dreams.

We figured a good place to start was a day hike. Oh yeah–had I mentioned we were not even day hikers? We were two middle-aged business owners and soccer moms. We spent that summer doing day hikes when we could squeeze them in, and spent that winter gathering gear. 

The following spring we did a short overnight trip. There were so many things I didn’t know. Who knew a proper backpack could make 35lbs on your back feel manageable? Who knew the forest could be so loud at night (earplugs are a must)? Who knew trekking poles were so amazing!? 

I felt like a total faker, a fraud, someone posing as a backpacker and looking pretty pitiful doing it. I totally overlooked the fact that I carried a 35lb pack for 10 miles.

It was a rough first outing with little sleep. Honestly, it had me second-guessing this whole backpacker thing. I felt like a total faker, a fraud, someone posing as a backpacker and looking pretty pitiful doing it. I totally overlooked the fact that I carried a 35lb pack for 10 miles.

Lesson 2: Don’t discount the little victories. 

For our second adventure, we planned to dramatically increase our mileage and double our nights in the woods. The Appalachian Trail may be a notorious 2,190 miles, but the Sheltowee Trace NRT is in our backdoor, and was the perfect next step for these newbies. 

We had a plan – 3 days, 2 nights, 26 miles.

Day 1 started before sunrise, with foggy breath and headlamps. We stopped at 10 miles–the total distance we traveled in two days on our first outing. This time we were smarter. We shared gear, lightening our load. We realized we didn’t need nearly as much food as we imagined, or extra clothes, or a lot of other fluffy stuff. We shared amazing rice and bean burritos and hit the bed early. Earplugs and a little ibuprofen p.m. helped us get a more restful night. 

Lesson 3: Mistakes don’t mean you’re a fraud; they just mean you have an opportunity to improve.

Despite ibuprofen and a luxurious new sleeping pad, Day 2 started off slow and sore. This is the point that imposter syndrome set in strong. I don’t walk 26 miles a week. What was I thinking trying to walk 26 miles in a couple of days? Occasionally, I would look up and see long, steep hills to climb. Those climbs felt daunting, but instead of focusing on the whole, I focused on the ground in front of me. I would count 50 steps, take a break to catch my breath and start again.

Same goes for business goals. I could not imagine having my current team or the revenue to support them during my first year of business. When I focused on that dream too much, I would get overwhelmed with how I would get there. 

Instead, I just keep doing the work each day and, 7 years later, I am almost to my second “big” revenue goal.

Lesson 4: Even the highest hills are just climbed one step at a time.

By midday we had a decision to make. Do we stop and make camp at 10 miles as planned, or do we push through and sleep in our own beds that night? 

At this point we had some data on our side. We had averaged 2 miles per hour for a day and a half. We were at mile 18 of 26 at 3 p.m. After some quick math and honest conversations about how much we didn’t want to spend another night in a tent, we changed plans with confidence. We were coming out of the woods.

My emotions and doubt said, “Are you crazy?! You can’t do a 16 mile day!” The data and the time of sunset said otherwise. All I had to do was keep taking one step forward at the same pace as I had. 

Yep, this felt familiar. I can’t count the times that I have told myself stories about what is possible in my business. Thankfully, I have surrounded myself with people (I’m looking at you Stephanie Skyrzowski and Autumn Witt-Boyd) who hold the data up in front of me and remind me otherwise.

Lesson 5: Data makes decision making easier and it pulls you out of your imposter head.

Something amazing happened about mile 22. Everything hurt. It had started raining about an hour before. The sun seemed to be sinking faster than I was walking.

But.

I was doing this! By God, I was a backpacker.
In the past 24 hours I had:

Carried 35lbs on my back

Hiked by head lamp

Slept in a tent at 40 degrees

Woke up sore and kept going anyway

Hiked in the rain

Hiked when every step hurt something.

Covered 26 miles in two days

Completed a 16-mile day 

I finally felt like a real backpacker. 

Are there more skilled, experienced, rugged backpackers? Absolutely! They would probably scoff at our heavy packs, slow miles or one-nighter baby hikes. But, I kept remembering the best piece of advice I have read over the past couple of years in regard to hiking. 

“Hike your own hike.”

Same goes for my business. Are there larger agencies with a more robust staff and larger accounts? For sure. Do larger agencies negate the good work we are doing for our clients? Heck no. For 7 years, P&P has been showing up and serving. I have built a business with a client list and team that I am proud of, and the success of other agencies doesn’t impact that, because…

I refuse to let imposter syndrome rob me of celebrating today’s success..

Lesson 6: There is no shortcut around imposter syndrome. 

You can’t go over it, you can’t go under it, you just gotta go through it. But once you go through it, you gain the confidence to tackle the next big challenge. Sheltowee Trace Section 2, I’m coming for you.