A paid gap year to backpack? How to go for a hike without quitting your job

FFinding enough free time from work to hike a long trail is an early hurdle that derails the dreams of many aspiring hikers. While some leave their jobs, wait to retire, or take advantage of a career gap to hit the road, everyone wants the holy grail: having enough free time to hike, without giving up.

Tabitha DeShane-Kirby aims to do just that, and even plans to go a step further by applying for a paid sabbatical and sponsorship for her 2028 Appalachian Trail hike.

DeShane-Kirby has been at her job, a leadership position at an insurance company, for about a year. «This is something I think I need to do more than just want to do,» he told The Trek of his AT ambitions. «However, I love my job and I have a family. I have children. I have to continue supporting them. So I can’t just leave.»

That’s why he started wondering if he could get his employer to join in on his hiking goals. In addition to the sabbatical, he hopes to have company sponsorship in the form of a one-time stipend to offset travel expenses and the cost of new equipment.

“I know I’m asking a lot, being a fairly new employee,” she admitted. But initial discussions at work have been positive so far. «They… thought it was a great idea, but not something my workplace had done before in the past. So it would set a new precedent.»

Emphasize the skills and experience you will develop

Former Amazon recruiter, hiker and Trek contributor Chloe Jacobs also weighed in on the topic. “I’m not familiar with paid sabbaticals or sponsorships, but I would recommend addressing the different skills (they) acquire from hiking that will benefit (his) employer,» she said. Some of those skills include problem solving, resilience, determination and self-initiation.

DeShane-Kirby is taking a similar strategy and going a step further by focusing on specific outcomes that would benefit her employer before, during and after the raise. «I’m in a leadership position, so… the core of what I said I would bring back to work would be contained in leadership development,» he explained.

She envisions a variety of possibilities here. «I was open to different formats, whether it was a podcast or blogs, or I had even mentioned a wellness initiative, because my workplace is huge on that. And then I was also willing to write a white paper, or even… an article for publication, and then also do trainings or Q&A sessions, things like that.» He also proposed using some company-branded equipment in the AT as a marketing tactic.

Chloe Jacobs spent five years as an Amazon recruiter before hiking the Pacific Crest Trail. Photo: Chloe Jacobs

Submit a detailed proposal

Hiker Will Trenda has taken unpaid time off from work to hike on three separate occasions dating back to 2017. Most recently, he took an extended leave from his banking job for a combined hike of the Pacific Crest and Colorado trails in 2023.

One of Trenda’s top tips for hikers looking to do something similar? Have as many answers as possible ready for your line manager, before they even have a chance to ask them. Trena recommended developing a detailed written proposal that describes the path you want to travel and why it is a realistic plan. Both Trenda and Jacobs, the former Amazon recruiter, also suggested citing studies on the benefits of gap years for both employers and employees.

For her part, DeShane-Kirby spent two months writing a proposal that outlined her goals and how they would align with those of the company. That document continues to evolve, as you adapt it to each person you need to present it to.

«You have to know your company’s values,» he advised. “I am doing (the proposal) very specific to my workplace and what they value… And then I’m also being very clear about their return on investment.”

Answer their questions before they can ask

A key goal of your proposal is to present your employer with a picture of what the raise will actually entail. DeShane-Kirby has an advantage in this regard, because his supervisor also hopes to hike the AT someday. “So I knew it was something she could relate to and would probably support me,” he said. That won’t be the case for everyone.

Most people haven’t heard of hiking or the specific trail they plan to hike, or only know about it in passing. Being able to represent the path through maps, images, and statistics can help managers understand the scale of what you are planning and make the prospect seem tangible. It also gives you a chance to show that your plan is realistic.

Will Trenda (center) and two friends on the Colorado Trail, which he hiked along with the PCT during an extended leave from his banking career. Photo: Will Trenda

“There is a little bit of support,” Trenda said of this process. «It’s like submitting your resume again.»

At this point, Trenda has perfected its proposal. You have a one-page memo template that addresses all the key points you want to highlight. All you have to do is update links to explanations of the specific path you plan to tackle, as well as the latest research that will support your argument for the benefits of a gap year.

Most companies have sabbatical and extended leave policies already codified. Don’t assume your direct manager will know what they are, Trenda said. Read them so you are prepared to express them yourself.

After submitting your proposal in writing, schedule an in-person meeting to discuss the request and, again, have as many answers ready as possible, including how this plan might fit into existing company policies. Jacobs also recommended becoming familiar with your company’s employee wellness program, if one exists.

Plan Ahead and Be Prepared for Rejection

Trenda, who previously worked in outdoor retail, has hiked the Appalachian Trail twice, in addition to the PCT and the Colorado Trail, and has never needed to leave his job to do so. Still, that’s not to say the process has always been frictionless.

When he said goodbye to his banking job in 2023, the request was so out of line from the bank’s perspective that it had to be escalated to the head of his division before he could get a response. «Because of the amount of time I wanted to take off, the reasoning, and it was also the first time anyone within our team had asked to do something like that,» was more than a simple yes or no question. It took time, but the bank finally granted his request for time off.

From a company’s perspective, there will be bureaucratic and operational complexities when an employee leaves for half a year. Giving them enough time to consider your request is courteous and will improve your chances of success. Trenda recommends giving at least eight months’ notice, depending on your industry. DeShane-Kirby is starting the process two years before her planned walk.

Photo: Will Trenda

Beyond solving logistical complexities, Trena also received criticism from managers concerned about how the time away would impact or delay his professional development. It would be six or seven months during which the company would not be able to review its work. You could miss out on bonuses.

Speaking to The Trek, Trenda was frank: «I don’t really care. I don’t feel like I’m on this earth to get promoted in a job that just pays my bills.» In any case, if a promotion results in a one or two year delay in promotion, how much will it really matter in the context of a career that will likely last decades?

Meanwhile, Jacobs has been vocal about the ways in which taking a break from work to go for a hike can really benefit your career goals. «Taking a break from your running to hike doesn’t set you back. It sets you apart,» he wrote in an article on that topic for The Trek last year. Backpacking long distances makes you stand out to employers and develops many interpersonal skills. That unique experience looks great on a resume, but your current company should value it too.

Read that article here: Why hiking is your next powerful step in your career

Jacobs reviewed thousands of resumes during her years as an Amazon recruiter. Photo: Chloe Jacobs

Know how far you are willing to go

Trena has never had an employer deny her request for time off to hike. But it’s something he says every aspiring hiker should prepare for. «Because they’re going to ask. Nine times out of ten they’ll say, ‘Hey, if we can’t do this, what happens?’

If things get tough, are you willing to quit? There is no universal right answer, but you should know your own answer before starting the conversation.

Nearly two-thirds of hikers in our 2025 Appalachian Trail Survey quit their jobs or were retired or unemployed when they hiked. But there are reasons to be hopeful. «It’s really expensive to hire outside staff and employers want to retain their employees as much as possible,» Jacobs explained. Companies have a clear incentive to retain good employees.

And the hard data indicates that it is possible to go hiking without leaving work. About 28% of hikers in our 2025 Appalachian Trail Survey made it last year: 7.6% on paid leave or sabbatical/vacation time, 7.6% taking advantage of summers off (presumably teachers), and 13.3% getting unpaid leave. Another 4% reported having a “flexible schedule.”

Requesting time off to do the hike will likely present similar mental challenges to those you’ll face during the hike itself. After all, hiking involves a lot of discipline, determination, and betting on what seem like long odds.

So is it possible to get time off, or even paid time off, to hike? Yes. Will it be easy to get it? Probably not. Either way, it’s worth asking.

Have you successfully secured time off or a gap year to hike? Let us know your experience in the comments below.

Cover image: Photo via Jessica “Stitches” Guo. Graphic design by Mackenzie Fisher.