In this episode of The Art of Imperfect Adulting, Amy Stone speaks with Penny Rose about the wild adventure of downsizing, embracing nomadic living, and designing a work-life balance fueled by intention and financial freedom. Penny shares her journey from a packed 1,640 square foot “sticks-and-bricks” house to 250 square feet on wheels, revealing the joys, logistical hurdles, and inner mindset shifts that paved the way for her and her husband’s life on the road.
About the Guest:
Penny is a CPA who helps multi-six-figure creative business owners gain financial confidence, make fearless decisions, and unlock the freedom they crave. Her journey began not in a business school, but in a high-stakes, freedom-limiting career as a forensic accountant at the FBI. While chained to a traditional office, she knew that to achieve true location and time freedom, she had to build a bulletproof financial system for her own remote business. She successfully created that system, and it became her escape plan.
Main Topics Covered:
Why Penny and her husband downsized and chose the RV lifestyle—including insurance headaches and financial motivations.
The planning, mindset, and logistical challenges of letting go of stuff, brick-and-mortar commitments, and local ties.
Emotional resilience in the face of change and feedback from friends/community.
The nuts and bolts of RV living: creating new traditions, maintaining community remotely, and the realities of “traveling too fast.”
Domiciling in Florida and the tax/legal intricacies for nomads and creators.
How Penny’s business “Penny in Your Pocket” supports influencers and travel creators with sound financial strategy—and her new micro podcast and online course for beginners.
Quote from the Episode:
“We obviously weren't using our space for very much besides storing stuff, stuff that we couldn't even get to... Once I met someone, I'm not only maintaining contact, I'm growing the community as I meet more people.” — Penny Rose
Timestamps: [00:00:05] Welcome & where Penny calls home (Orlando, FL—and half the year on the road)
[00:01:11] New Year’s traditions and Jeep culture
[00:02:43] First RV night: breaking free at the end of 2019
[00:03:26] Dreaming, planning, and facing “sticks and bricks” hassles
[00:07:52] Financial and emotional motivation for hitting the road
[00:09:00] How much stuff? Merging homes and the problem of “too much”
[00:10:59] Cutting other ties—work, clubs, church, and setting a departure deadline
[00:13:23] Early retirement timing and the role of benefits
[00:17:12] Downsizing method and COVID-era logistics; avoiding the storage unit trap
[00:20:13] Emotional vs. logistical challenge of letting go
[00:22:59] Community response: safety concerns, admiration, and surprise
[00:26:41] RV travel rhythm: “living” vs. “touristing,” building connection across states
[00:31:13] Domiciling 101: Florida, Texas, South Dakota, and tax homes
[00:34:43] Maintaining community online and in-person as a nomad
[00:37:56] Boundaries while working and traveling; not “traveling too fast”
[00:41:01] RV park favorites and growing new traditions
[00:43:58] How Penny’s work supports creators staying on the road
[00:46:53] Penny’s new micro podcast and online course for influencer finances
Note from the show: Guest offers are often limited-time and limited quantity. If you have an issue redeeming the guest offer please reach out to the guest or vendor directly.
