Today we’d like to introduce you to Erin Woodward.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
These days, life looks more like an art piece than a business plan.
Building and exiting businesses in the medical field gave me the financial freedom and time to explore a wide range of interests and unconventional pursuits.
That eventually evolved into funding and advising other people’s startups, often providing capital when other investors wouldn’t.
Through serving on nonprofit boards, I found myself wandering into rooms of peculiar admission.
Part of my time is dedicated to veterans and preserving history. I am currently producing a WWII-era pin-up calendar project that raises funds for veteran programs while honoring the generations of women whose lives were shaped by war.
My nonprofit work is leading me on a pilgrimage through the Pacific battlefields and inland Japan, retracing the path of World War II under the avatar Annex Fox 2027. The goal is not only to better understand war, but to write a memoir exploring family legacy, sacrifice, grief, resilience, and what we inherit from people we never fully knew.
I’ve also been focused on Rhinestone Cactus—my luxury travel concept built around the belief that meaningful experiences matter more than status symbols. It’s for people who are bored with obvious luxury and want something more personal, memorable, and unexpected.
The common thread among these pursuits is a fascination with possibility and a desire to push beyond conventional boundaries.
I’ve completely set down the pursuit of conventional success. Today, my focus is on preserving other people’s stories, creating meaningful experiences, and helping people get where they want to go.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Not even remotely.
From the outside, people often see the business exits, the travel, the accomplishments, and assume the road was somehow linear. In reality, it was full of detours and challenges. Success is a bouquet, not a ladder.
One of the hardest lessons was learning that success doesn’t solve every problem. You can achieve goals you’ve spent years chasing and still find yourself asking, “What’s the meaning of all this?” Building businesses taught me how to strive. Leaving them taught me who I was without them.
I’ve also navigated family loss, complicated relationships, burnout, anxiety, and the challenge many high achievers face when their identity becomes too attached to accomplishment. There were periods when I had to learn that productivity and worth are not the same thing.
Ironically, some of my biggest growth happened after I no longer needed another business success. Once the pressure to prove something was gone, I found myself drawn toward service, preservation, writing, and helping people whose stories may never make headlines but deserve to be remembered.
The struggles weren’t roadblocks. They were course corrections.
Can you tell our readers more about what you do and what you think sets you apart from others?
I’ve never been particularly interested in staying in one lane. Young in my career, I was singularly focused., and that’s what allowed me to achieve financial freedom.
Now that I have financial freedom, I have room to veer.
Today, my work lives at the intersection of entrepreneurship, storytelling, preservation, philanthropy, and travel.
I curate travel for others. I preserve legacies.
Can you talk to us a bit about the role of luck?
What I’ve learned is that luck tends to show up disguised as timing, relationships, and unexpected invitations. You have to recognize when you’re being blessed and walk through the door.
Pricing:
- Collector WWII era Pinup Calendars $50 – all proceeds go to veterans.
- $150 non-refundable design fee – Rhinestone Cactus Travel
Contact Info:
- Website: https://ebwoodward.com
- Instagram: https://www.instagram.com/e.b.woodward
- Facebook: https://rhinestonecactustravel.com
- LinkedIn: https://www.linkedin.com/in/erin-woodward-881830a4
