Most Workampers hit the road looking for jobs.
Tim Winders and his wife, Glori, did the opposite.
When they rolled out in their Class A motorhome on January 1, 2019, they weren’t searching for campground positions or seasonal work. They were building a lifestyle centered on flexibility, independence, and control over their time.
“We celebrated our seven-year anniversary of RVing just a few months ago,” Tim said. “That was our beginning.”
While many RVers discovered the lifestyle during the pandemic, Tim and Glori were already living it — intentionally.
“We looked at each other and realized we’re already living a socially-distanced lifestyle here in our 39-foot Class A motorcoach” Tim said.
Running a Business From an RV
Tim is a business coach who works with leaders and teams across the country. His work includes coaching, writing, and hosting his podcast, Seek Go Create: The Leadership Journey.
And it all happens from inside their motorhome.
After purchasing a 2006 Gulf Stream Sun Voyager, they gutted the interior and rebuilt it to support two remote professionals.
“We actually took the passenger seat out of our RV in order to create a small office space,” Tim said.
At one point, Glori worked remotely for a Silicon Valley company. Today, she supports operations and creative projects within Tim’s business.
This is where Tim’s and Glori’s path differs from traditional Workamping. They don’t trade hours for a site. They don’t rely on seasonal positions. Their income is fully location-independent.
That gives them the freedom to decide where they go and how long they stay.
Designing Travel Around Life (Not the Other Way Around)
Like many RVers, their early travels were driven by destinations, but that has changed over time.
“It used to be about what we haven’t seen yet,” Tim said. “Now there are two things that matter most: proximity to granddaughters and the weather.”
When your income isn’t tied to a location, your priorities change. Their travel now reflects that shift.
Tim and Glori aren’t constantly moving. In fact, they actually only move the RV and travel about 8 to 10 days per year.
“We really enjoy staying places a minimum of a month and sometimes up to three or four,” Tim said.
That slower pace leads to a very different experience.
“We’re not good tourists,” he said. “We’re good at hanging out in places and exploring. But, we’d rather explore on a Tuesday instead of buzzing in on a Friday, seeing everything on Saturday and Sunday, and then heading out again on Monday morning.”
For many Workampers, this slower approach reduces stress, lowers fuel costs, and creates a more sustainable lifestyle.
Internet Is the Backbone of Remote Work
If you’re running a business from an RV, internet is not optional — it’s necessary infrastructure.
Tim learned early that campground Wi-Fi wasn’t reliable enough for client work or video calls. After testing multiple solutions, he adopted Starlink in 2021. Today, it powers nearly everything he does.
“If you need internet for what you do…it’s worth it,” Tim said.
He also prioritizes security.
“I am not comfortable doing banking or entering credit card information on a shared network,” he added.
For remote Workampers and RV entrepreneurs, reliable internet should be treated as a core business expense.
Smart Setup Decisions That Made a Difference
Before going full-time, Tim and Glori made a few key decisions that helped simplify their transition.
They chose South Dakota as their domicile, a popular option due to its simple residency requirements.
They also bought used instead of new.
“If anything has gotten the kinks worked out, a used RV should have done that,” Tim said.
That decision helped control costs while they tested the lifestyle.
Lessons Learned Along the Way
Not everything worked perfectly.
During their renovation, they installed new flooring that looked fantastic…until temperatures dropped in Colorado.
The flooring started to buckle due to expansion and contraction from temperature and humidity swings.
It was a practical lesson: construction materials behave differently in an RV’s ever-changing climate.
Advice for Workampers Considering Self-Employment
Tim doesn’t take traditional Workamping jobs, but he regularly interacts with Workampers and respects the path.
His advice is simple:
“If there is any way to try something before you totally throw yourself into it, I would.”
That might look like:
- Renting or borrowing an RV for a month
- Taking a short-term Workamping position
- Testing a remote income stream before going all-in
For those with portable skills, self-employment is a viable option.
Opportunities that can travel with you include:
- Coaching and consulting
- Writing and content creation
- Online businesses and digital services
“If you’re feeling nudged, take a few steps and see how it works,” Tim said.
A Different Kind of Workamper
Tim and Glori Winders represent a growing segment of the Workamper community. They’re not working the front desk or cleaning sites but they’re still living the Workamping lifestyle.
They are:
- Self-employed
- Location independent
- Intentional about how they works and travels
Their story highlights an important shift — Workamping is not just trading labor for a campsite. For some, like Tim and Glori, it’s about building income streams that move with you.
Listen to the full interview with the Winders at the Workamper Show Podcast episode 328
Workamping Can Look Different for Everyone
Not every Workamper will choose self-employment. Many prefer the structure, community, and simplicity of traditional Workamping jobs.
But for those who want more flexibility or already have portable skills, there are more options than ever.
Whether you’re looking for your first Workamping job or exploring ways to earn income on the road, the key is the same:
Start small. Test the waters. Build from there.
Continue learning about unique Workamping opportunities, traditional Workamping jobs, remote-friendly opportunities, and employer listings by visiting the job listings page on Workamper.com, where new positions are added regularly across the U.S. If you want direct access to the most Workamping jobs and information on the internet, become a member today!
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