How to Get Time Off Work to Hike the Appalachian Trail: Convincing Your Boss and Managing Life

Want to hike the Appalachian Trail but worried about getting time off work? Here's how to convince your boss, plan ahead, and balance life commitments for your thru-hike dream.

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Josh Koop

I live with my wife and daughter in Katy, Texas and my local trail is the Lone Star Hiking Trail which is an amazing way to experience the Sam Houston National Park!

Man exploring the Appalachian Trail after getting time off from a job
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For most aspiring thru-hikers, their biggest roadblock is managing their current employment. They want to know whether they should quit or if they can find a way to get a leave of absence and how to sell this to an employer as a benefit to the company.

Today I wanted to dive into how to get time off work to hike the Appalachian Trail and how to think about selling it to your employer.

The simplest and most common answer is just to quit your job. This may be the perfect answer for many with a minimum or very low wage, as there is always another opportunity. But when you have a career and have built a long-term relationship with your employer, this can be a more difficult decision process.

Since anyone with a very low or minimum wage has a simple answer, today’s focus will be on those with the more difficult decision process.

Those who may have the ability not to quit but instead take on the hike as a benefit to their employer(1). If not, many have an LOA or leave of absence they may accept.

Why Quitting Your Job Isn’t So Simple

For most people choosing to stop everything and leave for six months or longer is a huge life-altering change that impacts far more than just their job. It would affect their home, car payments, health insurance, and other benefits they receive from employment.

It’s also worth noting that people in certain positions can’t just leave without notice. If you are a doctor, lawyer, or have any type of security clearance, your employer may not accept you’re giving two weeks’ notice and leaving for an extended period of time.

Additionally, many people have a 401k or other retirement benefits that are only accessible if they maintain their current employment. Quitting would likely mean forfeiting these earnings as well.

Family Commitments

A huge issue for most who aren’t just graduating from high school or college, when you have a family and especially with children, you have a different level of commitment where you can’t just decide to leave them for six months or longer.

Doing this forces your partner to pick up all the weight; they have to manage the home, their job, and all child duties, which is unfair. This would require many discussions to determine if it’s the best thing for your family and how you would make it work.

Then you would have the mental resolve to manage to be away from them for over six months; for many, the real reason they quit isn’t physical but mental.

Financial Responsibilities

As you grow in your career and life, you build up commitments through unpaid bills like purchasing a house or monthly bills like credit cards and utilities. You also have other financial responsibilities like a mortgage or car payment, which make planning difficult.

All these make it much harder to quit your job for an extended period as you need a consistent income to cover these costs. If not, you would need to start a lengthy process of either paying everything off prior or starting the commitment to sell it all off to clear the bills.

Loyalty to Your Employer

This happens to most adults as the job becomes part of their life; they feel they are “part” of the company and find it very hard to do the work to separate themselves from the company.

This may be the hardest part of the decision to leave, as you have put so much time into building your career and developing a relationship with your employer.

Leaving all that behind can feel like you are giving up on all that progress, which is a scary proposition for many.

Insurance Considerations

Another big issue, especially in the United States, is that you have to have insurance. If you quit your job, you lose access to their option, and, to be fair, Cobra will bankrupt most thru-hikes.

If you need insurance, you can look on the open market but expect to have a large bill, or you can look into things like World Nomads and temporary travel insurance for the entire hike.

A majority of hikers must consider how they will maintain their health insurance when leaving their job to hike the entire trail .

Strategies to Gain Time Off for Your Hike

Now that there is a better understanding of limitations and thoughts before even broaching requesting time off, we can dive into ways to request or the best times to take a break from the career wheel.

Sabbatical or Leave of Absence

The best option for someone with years and a solid history with the company to get approved for would be a leave of absence or sabbatical. Both of these would mean the spot is open for you to return to once you have completed your hike.

This requires some good record-keeping on your part; generally, a sabbatical is for much longer than a leave of absence. The key with both is that you have to have a plan and present how this time off will positively affect you and the company.

The company wants to know how you will return and be better for the experience and how it will add to the company culture or knowledge.

Remote Work Agreement

More an agreement that you will work some set amount of hours each week to maintain some part of the job.

The benefit to the company is that they don’t have to replace you, and the benefit to you is that you still earn an income and can work from anywhere with internet access.

This does not work for all jobs, but it depends on how much control or ease it would be to do your job remotely.

Some companies are now more understanding of this as we have moved into the post-pandemic world, and this leads to a newer digital age and understanding of how to make this work for both parties.

Become a Seasonal Worker

Many may quit their previous full-time job and look to pick up more temporary employment. This can work well as you don’t need to explain the intent behind your leave, and this leaves you safe from termination once they know a cause for leaving.

This will make it harder to maintain health insurance but may be a better option for some people. Taking on shorter-term employment also allows you to leave sooner as you won’t be looking to save all the amount you need before starting on the trail.

Use a Transitional Period in Life

It is far more common to note that thru-hikers tend to be at a life-changing time, and this transitional period itself lends to taking on new adventures.

This may be the perfect time to knock out a long-term goal for those nearing or just starting retirement and looking for one last grand adventure.

For those who are in college or just graduated, it may be a great way to take some time before joining the workforce full-time.

This also generally coincides with having fewer responsibilities, whether a family or a mortgage.

Work Extra and Save Aggressively

This is how I did many things as a young adult; I would pick up a second job with the income dedicated to a specific purchase or need. If you want to accelerate your plan, you can add a second job to pay off bills or start or build the war chest faster.

This will put you in a better financial position to leave sooner and have more money to maintain on the trail.

Saving is critical, and how much one saves can significantly change how soon one can leave for their hike.

Downsize Your Lifestyle

One of the best ways to accelerate your ability to save and take time for your long-distance hike is to sell off the things you don’t need and downsize what you do from larger and more expensive to less expensive and more manageable.

You may move from a house or apartment to a smaller one or eliminate a car altogether. The key is to make a concerted effort to reduce your monthly expenses by looking at what you need in life.

This will help you save more money each month towards the goal of taking time off for your Appalachian Trail thru-hike.

Build a Side Business

In the age of YouTube and other online businesses, you could look to begin building up a side hustle with supplementary income to help you save for and take time off for your hike.

This takes some extra work to get going, but if you can make it work, this could be a viable option to shorten the timeline for your Appalachian Trail thru-hike.

In addition, building a website on things you love and are passionate about can change your career overall and lead to more happiness over time.

Investing in your knowledge is never bad, especially when it is a manageable cost. Unlike many college degrees, I learned how to write well and build a blog through this course if online business is interesting.

If you are interested, it is a good way to learn how to be a quality writer, but note they focus on building a site over 24 months. It isn’t some get rich quick or overnight scheme!

Man relaxing after a hike up to a peak on the trail

How to Tactfully Convince Your Employer

To effectively accomplish this, you must start at least six months in advance as you will have many things you will need to prepare them and yourself.

You don’t want to make this runway too short, or it could damage them or your relationship with your employer.

Give Plenty of Advance Notice

When you are on good terms and are a high performer, be open with them far in advance. The longer you can put the first thoughts, the better.

Telling them you are planning to hike in advance lets them think and ask you questions without you putting pressure on them.

Then they can come back with questions, and you can start the conversation around leave of absence and how this sabbatical will make you a better employee as you will face issues and have only your wits to lean on.

This growth will help you become a far more valuable employee to the company.

Collaborate on a Detailed Plan

If your boss is supportive, you will want to devise a plan for how this leave of absence will work.

This should include the expected timeframe of how long you will be gone, what projects can be delayed or assigned to someone else, and how you will stay in touch (if at all).

You should look to build out documentation of everything you do and your overall tasks and responsibilities to ensure nothing is missing and everything can be covered in your absence.

Document Your Role Thoroughly

Many times your job will be far different than your “job description,” and getting this all documented can help ensure a seamless transition while you are gone.

This will also help your boss see how valuable you are to the company and how much work is involved in what you do.

Additionally, this can be used as a training tool for someone who may need to fill your role while you are away.

Delegate Your Work Responsibilities

You want to find the right person to take over tasks and responsibilities, and one person more than likely won’t be able to handle them all. This is okay.

Ensure you have a solid plan for how things will get done in your absence, and ensure this is well documented and communicated.

This way, there are no surprises, and everyone knows what is expected of them. This also gives the company the time to know if they need to hire a contract employee or temp to help manage this if it looks too much for current employees to carry.

Offer Occasional Availability

The last part of this agreement can be to determine how often you can be available for the employer to discuss things with you and help them with their problems or issues.

You want to be able to help them still but also give yourself the time to enjoy your adventure. This may mean you are available via email or phone a few times weekly or just once a month for a video call.

Again, this should all be well documented so there are no surprises and everyone is on the same page.

Stay Flexible and Communicate

Remember, you want to keep the lines of communication open with your employer. You don’t want them to feel like you are just abandoning them.

Additionally, if things come up and you need to adjust your plans, let them know as soon as possible so they can make the necessary arrangements.

Planning Your Thru-Hike: Final Tips and Takeaways

Taking time off to hike the Appalachian Trail is a fantastic goal and one that can be accomplished with careful planning.

There are many ways to make this happen, and it comes down to how much time you need, how much money you need to save, and what your company’s policies are.

The most important thing is to start the conversation early, be prepared, and have a solid plan.

This will give you the best chance for success. Good luck!

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