So You Want a Leave of Absence?

If an extended hiking trip has always been your dream (and it is for me), you may be thinking about requesting a leave of absence from your job. I enjoy my work and the team I’m on, but I still knew that it was time to take a break and try hiking the AT (no pets, no mortgage, and not many other things tying me to NYC right now).

I didn’t want to quit outright and thought that requesting a leave of absence would be the best balance between my personal goals and my team’s needs. Here’s the process I went through in case you’re considering a similar ask.

Do Your Homework

Do a deep dive on your company’s policies, or better yet see if you can chat with someone in HR / benefits to get the full details on extended time off. Leave policies (if they even exist) vary by company, and it’s important to find out what the options are before you start planning. Sometimes there’s no long-leave policy at all, and you will have to weigh whether hiking is enough of a dream to justify resigning (though it’s probably an easy choice, if you have gotten this far).

At my job, I was able to accrue a certain number of vacation days, roll over some saved days from a prior year, purchase a few additional vacation days, and request leave without pay for around 4.5 months. One person I worked with took a year off, and someone else in New York did three months, but otherwise I hadn’t heard of too many extended leaves other than for medical / family reasons. After checking the leave policies, I had a few coffee chats with my friends in HR to understand more about our long-term leave policy and whether many people get approved for it.


I joined my firm in 2015 and have been with the same group for about 3.5 years. We do midyear and annual reviews, which include ratings and details across different performance areas. I combed through my reviews to highlight a good track record, which I thought would be important when asking for extended time off, especially a bit earlier in my career. The highlights of those reviews made it into my request memo.

What’s the Right Timing?

At my firm, I have a four-week notice period in my employment contract. I suppose that technically I could have asked to go on leave four weeks ahead of my start date, but I didn’t feel that was the best way to approach a career break in the long term. I had a one-on-one chat with my manager in early December, about four months before my intended start date, to lay out the reasons I wanted to hike and to see if she would be supportive of a leave of absence. Thankfully that conversation went well (consensus: it’s a crazy but awesome plan), and then I started my formal absence request process. I also think that it helped to highlight how different the trip would be from my job (no conflicts of interest) and how many things I will learn or build up along the way (perseverance, planning, leadership).

About a month before my start date, I wrote up a one-page memo with a few sentences on the Appalachian Trail, some bullets on my performance reviews and ratings, and how I would combine vacation and unpaid leave to cover my six month thru-hike attempt. I patched together my saved, rolled over, and purchased vacation with some unpaid leave, which will cover me from April through September.

Know Your Manager

The advance notice timing worked for me as I sit on a small team, and there’s plenty to do when we learn someone will be out of the office. I wanted to give my manager as much notice as I could so we could find a way to carefully approach the request without distracting everyone from our existing responsibilities. I also wanted to make sure I could tactfully announce my upcoming time out to my colleagues. Not every job or team dynamic might allow for that kind of timing, and I know some people ask for sabbaticals right at their notice period so there’s a lower chance of negative repercussions. That was a trade-off I was happy to make, and I’m glad I approached the topic early. On the other hand, if you don’t feel secure in your role, or if you don’t have a close working relationship, it could make more sense to raise the topic with your manager a lot closer to your departure date.

The Details

Make sure you fully understand the effect of a leave of absence on health insurance and other benefits your company might offer. I’m planning to get a travel insurance policy to cover my trip anyway, since I’ll be so far from my home state for much of the hike (plus, it covers a bit more than a generic health policy would, such as delays/cancellation for my train to Georgia).

I also need to sign a resignation letter just in case before departure, as jobs aren’t guaranteed at my firm if you are gone for more than four weeks on this type of leave. I’m thinking of it as a handshake agreement to come back in the role that best fits my group, because a lot can change between March and September in the business world. That’s a scary thought, but ultimately I know that I have to try the AT, and the earlier I do it in my career, the easier I think it will be to take off several months in a row.

You’re Not Alone

Plenty of other people face the same kinds of work challenges, and not just for taking time off due to hikes. This season alone I talked to two other AT hikers (fellow Trek bloggers Sara and Emily) who went through their own journeys to try for extended time off.

Ultimately you need to decide how important a thru-hike is, if that makes more sense than stringing together sections, and whether you’re willing to have a conversation about extended leave vs resigning. No two situations are quite the same, but I’ve found that honesty goes a long way in the workplace, and it’s easiest for me to be upfront about my goals.


Some helpful articles and suggestions as I made my plans include:

FastCompany’s article on an LOA from a software startup 

New York Times article on why people should take more career pauses

Fellow blogger Brandon’s leave strategy 

Various threads on r/AppalachianTrail

Advice from several current and former colleagues (who helped me keep things in perspective).

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Comments 6

  • Josh Johnson : Mar 7th

    Might have to do this myself. Thanks for sharing!

    • Katharine : Mar 7th

      Please do it! The worst that can happen is a “no,” and at least you’ll have tried.

  • Sin Nombre : Mar 7th

    Well-done article. I went through this process myself for my 2016 AT thru hike. I’d been with the department 11 years at that point; We’re a large, multi-national technology company and we had absolutely no documented provision for extended leave. I am fortunate to have had a manager who understood the appeal and what I was trying to do and who could live vicariously through my hike; He really went to bat for me in selling this up the food chain. Ultimately, it had to go for approvals three levels above my job. Troublingly, an HR director who was also consulted responded, “If we can lose him for 6 months, maybe we don’t need him at all,” so be aware that there are plenty of non-idealistic people in the corporate world who won’t understand the value in this endeavor. I know of other thru hikers my class who hit roadblocks like this HR person and had to quit to do their hikes (none of them regrets doing so). Ultimately, I did get approved, they hired a temp to cover my job for 6 months.

    One of the lessons you learn on a thru is that you make your own opportunities; For a lot of us, getting time off to do this hike is the first of many times you learn that lesson.

    • Katharine : Mar 8th

      That’s great color, thanks for adding. I’ve also never spoken to someone who regretting taking time for their hikes, which made me feel better about my request.

  • B-Squared : Mar 8th

    I’ll give my experience. 24 years as a salesman for a large corporation. Decided I wanted to thru hike the AT in 2017. Asked the boss 30 days in advance (hindsight, I probably should have done it sooner, however the company has a history of telling people to go ahead and leave when they are resigning) Explained to my boss it had been a lifelong dream, and that who knows I may decide two weeks in that long distance hiking is not for me or I might fall and break a leg. He and HR (btw HR rep had just returned from a 6 mo LOA due to her pregnancy – I know the difference – just making an observation) explained that my position was too valuable to allow LOA of that length (5-6 mo), and if I was adamant about going I would have to resign. Twenty-four years and out the door thank you for your hard work and dedication. My last day was 4/1/17 – started at Springer on 4/12 – fell and broke my wrist on 4/12. Go Figure. Had surgery on 4/14 (got lucky, orthopedic surgeon and his sister had thru hiked 20 years ago and understood what I was trying to do….after he had a hearty laugh) two weeks later started my hike again – completed my hike on 10/7/17. All during this time never heard from my old boss, but had two other competitors who heard of my adventure and they offered me a position when I got back. Moral of the story…DO IT…right or wrong who knows what the future has in store for us. Follow u, since my AT thru hike, I have done a Camino and a West Highland Way TREK – God I love to hike………………..

  • Jan Steen : Mar 19th

    We also make sure that employee are informed about the fact they should always handover a formal request for leave even though they already informally informed their manager. By doing this, HR can follow procedure and the employee and his manager does not have to worry afterwords. We use default templates like this leave of absence form. You can easily add it to you HR workflows.


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