Announcing your thru-hike…to your boss

Last week, I accomplished my first (and currently scariest) self imposed milestone of the Appalachian Trail adventure… I told my employer about my plan to hike. From the people in my personal life, I’ve gotten mixed feedback on this choice. Some have said I should have waited – I’m only required to give 2 weeks notice and telling my company is a risk. Others have been totally on board with me. I assume my work scenario is a pretty common challenge for people planning to complete a thru hike that aren’t at a natural milestone in their life (graduation, retirement, etc), so let me attempt to explain my choice.

Why I Told

1. I feel guilty very easily. My work requires some major future-planning, and timelines, goals, etc, are being heavily made for 2016 at this point. I have now been in multiple meetings agreeing to things that will be happening in March 2016 onward, knowing full well that I will certainly not be around at that point. I have that feeling in the pit of my stomach saying “this feels crappy.”
2. I want to do the right thing. This is the part of the post where my wonderfully philosophical hiking partner Caleb would say “What is ‘right’? Why do you consider this the ‘right’ thing to do?” Well, I don’t know. I guess I just had a feeling in my gut that said 3 months is the right amount of time to give my company. I understand that this varies vastly for people. Caleb will only be providing 2 weeks notice due to the nature of his work. But, my employer is wonderful. Flexible, great benefits, and very mission-oriented. Not-so-coincidentally, their mission includes hiring people who care about the environment and have a life outside of work (usually that includes hiking). They highly value personal pursuits and I knew that as hard as it would be to tell my boss that I would be leaving, I also knew that everyone would respect my decision and I would not get fired. I also know that the hiring process at my company takes a lot of time (~2 months), and I wanted to ensure that I allow enough time for my replacement(s) to be hired and at least somewhat trained.
3. I’m excited! I was just plain sick and tired of keeping it in! Hearing my coworkers talk about their weekend hikes, them asking me about what I’ve been up to…it’s hard not to share the planning and excitement that I have now been building up for over a year.

The Reaction

Not sure if this is accurate.

1. Kind of anticlimactic. I have a home office and work remotely 95% of the time, so unfortunately I had to do the big reveal over the phone. This really stunk. It’s hard to read people over the phone (even after thousands of phone calls over more than a year of working remotely). I imagined this scenario where my boss would say “Wow! That’s so awesome!”, and proceed to ask me all sorts of detailed questions about the trail. This did not happen. Lesson learned: no one will ever be as excited for me as I am for me. And I wouldn’t really expect my boss to be excited, I guess… I imagine it’s kinda crappy to be told a decent employee is leaving.
2. Briefly complicating. I made up my mind some time ago that I did not want to return to my company after the trail. Despite the positive aspects of my job, there are many reasons why I want to use the trail as a way to amicably part ways. Well, after I told my boss about my grand plan, he presented another option – frame my time off as a leave of absence, which would mean I could retain my health insurance and some other perks – including having a guaranteed job when I get back. This was very tempting. The trail will be expensive (even with a strict budget), and the stability of a job post-trail would sure be nice. For a while, I was really leaning toward taking this offer and agreeing to go back to my stable but kind of miserable job after the trail. BUT THEN I REMEMBERED – I’m trying to do this crazy thing to change my life and not live such a boring, unfulfilled existence! So I respectfully declined. If I am struggling post-trail and want my job back, I can always go back through the normal hiring process. I’ve always been one to do the practical, logical, safe thing, but it’s too important to me to strike out into the unknown on this one. This is why I have been planning and saving money for over a year!

What are my fellow hikers planning job-wise? If you are currently working, have you told your employer? Do you plan to return to your position post-trail? I’d love to hear your thoughts!

Photo courtesy: Michael Scott (https://media.giphy.com/media/eyjXmU6feYA3m/giphy-facebook_s.jpg), Office Space (https://fogsmoviereviews.files.wordpress.com/2012/07/office_space_milton.png)