Finding My People on the Pathless Path
By Penny Rose, CPA and Creator Tax Strategist at Penny in Your Pocket®
When I left my job at the FBI and hit the road in a recreational vehicle to build a niche CPA firm for creators from the road, I knew I was choosing an unconventional path. I traded structure for freedom, a steady job for self-designed work, and a predictable identity for something far more fluid. I expected uncertainty. What surprised me was realizing how alone on the path I felt.
Not lonely — just unmistakably aware that no one around me had ever done what I was trying to do.
My friends from my old Federal job couldn’t give feedback; they didn’t understand why anyone would build a business this way. My fully supportive husband hasn’t walked the entrepreneurial path himself. And even my CPA colleagues weren’t creating courses, designing podcasts, or experimenting with helping creators in the ways I do. I was venturing into territory where none of my usual sounding boards could really help me.
That’s where the importance of a different kind of community became obvious.
Over the last two years, The Prosper Network has become that grounding space for me. I first joined a speed networking session out of genuine curiosity — not sure what I’d find, not sure how it worked. But conversation after conversation revealed something I hadn’t had before: people who truly understood the questions I was wrestling with.
They weren’t confused by experimentation; they lived in experimentation. They didn’t tense up when I shared a new idea; they leaned in. And the more I connected with women inside Prosper, the more I realized how essential it is to have peers who don’t flinch when you say, “I’m trying something different.”
These connections didn’t stay inside the networking calls. They became mentors, collaborators, and quiet encouragers. Some have tested my lead magnet custom GPTs. Some share my podcast episodes. One woman I met inside Prosper is the reason my micro-podcast even exists — I took her course, and it opened a door I didn’t even know I was standing in front of.
Reading The Pathless Path recently helped me put words to what I’ve felt for two years. Paul Millerd writes that the longer you stay on this unconventional path — and the more effort you invest in connecting with people walking in a similar direction — the better your life becomes. I didn’t have the words for it until now, but I’ve been living that truth all along.
Here’s what I learned:
When you redefine your work and life, you need peers who understand the version of success you’re building.
Without that, you stay alone on the path. With the right community, the ground under you gets steadier.
And here’s what I suggest you do: If you’re building a business that doesn’t look like the one you left… if you’re designing a life outside the default playbook… if you’re craving people who don’t flinch at your ideas — join a community made for the pathless path.
For me, that’s The Prosper Network. It’s where I found people who speak the same creative, experimental language I’m trying to live. And it might be where your next chapter finally clicks into place.
