On this blog, I have branded myself as a “part-time traveler.”
Which, by the way, I totally am. I’m not a “digital nomad”, or someone who calls a new country home every month. I have an apartment, a boyfriend, a car, and a job all conveniently located together in the bustling city of Houston, Texas.
Well, until last week, that is.
When I decided to book a one-way ticket to Nicaragua, I was simultaneously disrupting one key part of that equation: I was going to have to quit my job.
I didn’t view quitting my job as a permanent fix; it was simply something that needed to happen in order to take this multi-month trip that I’ve always dreamed of. I had the savings to afford the trip as well as some expenses after I returned, although I totally planned to find a new source of steady income in Houston when I got back.
Cool. Groovy. Solid plan, right?
Um, except the part where I have to tell my boss that I’m no longer going to be working for her.
* Cue mental breakdown *
The Lead-Up
It’s important to note that my boss is not a monster. She’s actually amazing, and as the date of me giving her my three-weeks notice drew closer, I was beginning to have more and more anxiety about it.
I was absolutely terrified about disappointing her or letting her down, as well as of placing an extra burden on her or my team members by leaving. Oh, and of stopping the flow of my one and only source of steady income.
I had savings, but what if when I returned from my trip, no one wanted to hire me? Like, ever? What if I never had a job or money ever again, and my boss and all of my co-workers hated me for abandoning them, and I had to live the rest of my days like a leech, draining the financial resources of my boyfriend and parents?!?!
I kid you not, these were the thoughts that plagued me throughout the days leading up to “the talk” with my boss.
If you’ve never had to quit a job, count yourself lucky. The guilt, stress, anxiety, fear, and self-doubt literally kept me awake at night for weeks.
But eventually the day came when I had to let her know what was up. I was set to leave in three and a half weeks, and I wanted to give her three weeks of notice to make the transition as easy as possible on her.
So, I sent her a simple email: Do you have some time to chat this week?
She responded by sending me a meeting invite for the following morning.
It was now or never.
The Talk
Me: I have something that I need to talk to you about.
Boss: Okay.
Me: I want to start off by saying that I love working here. I love working for you, and working with the other team members, and I am so grateful for all of the opportunities that you’ve given me here. But…I need to tell you that I’m giving you my notice to leave this position.
Boss: ….
Me: It’s not because of another job opportunity, it’s actually because of something a little more personal. You know that I’ve had some really amazing opportunities to travel this year (See: Thailand, Germany, Austria) and those trips have only made me more passionate about travel. I’ve really been wanting to take a longer trip abroad, and I’ve thought a lot about it, and I really feel like now is the right time in my life to do so.
Boss: ….
Me: So, I’m planning to take a trip to Central America for several months, and I’m planning to leave in September. I wanted to give you enough notice, to make sure that we have time to transition my projects to other team members or begin looking for my replacement. I’ll still be able to work here for three full weeks…assuming that’s what you want. Obviously, it’s your decision and I’ll respect whatever you want me to do, but I really do want to make this process as easy as possible for everyone else.
Boss: Wow…Kelly, I AM SO PROUD OF YOU. This is going to be an amazing opportunity for you, and you’re right, this is the perfect time for you to have this experience in your life. Of course, we’re going to miss you a lot, but I think this is going to be really amazing for you.
Me (internally): ?!?!?!
Me (externally): Thank you so much! I’m so glad to hear that.
Boss: But, I can’t accept your resignation.
Me: *awkward nervous laugh*
Boss: No, really.
Me: *smile, nod, wait*
Boss: You know, there really is plenty of work that can be done from anywhere in the world. If you ever get bored down there in Costa Rica or wherever, give me a call and I’ll be happy to give you some work. We could even come up with a schedule in advance before you leave. Just something part time, and you could work remotely. What do you think?
Me (internally): !!!!!!!!!!!!!!!!!!!!
Me (externally): Yes, absolutely! I would love to continue to help out in whatever way I can. And I’ll definitely have free time while I’m there, so I would love to keep working as a part of your team. That would be amazing.
Boss: Great! Work out a plan and let me know what you come up with. You can work as much or as little as you want. Whatever is best for you, I’m happy to do. And I’m really happy for you and this new opportunity that you have before you. It’s going to be incredible.
The Afterthoughts
Disclaimer: The above conversation is NOT a work of fiction.
This. Literally. Happened.
I just might be the luckiest girl in the world.
I mean, I’ve spent MONTHS stressing, budgeting, and deciding whether or not I was really okay with giving up my only source of stable income.
I was completely terrified of being broke, but ultimately I decided that giving up my job was worth it in the end. I was going to follow my dreams and pursue new opportunities, and if that meant stressing about money for a while, so be it.
I’ve spent the last few weeks seriously hustling to find ways to make money on the road. I’ve been snapping up freelance writing gigs whenever possible, and exploring my options for making an income remotely.
And all this time, the most viable option was right there under my nose. And I never even thought to ask for it.
Seriously, why didn’t I think of this before?
Instead of jumping straight to quitting my job, why did I never think to ask my boss for the option to work remotely?
What’s the worst that could have happened? Probably that she’d say no and fire me for even asking…which would land me in essentially the same situation as if I’d just quit.
But the best case scenario? She’d say yes! (Which magically ended up happening even though I wasn’t smart enough to ask. Dear Boss, if you’re reading this, you are THE BEST).
The moral of the story?
Aim high. If you’re thinking about quitting your job to follow your dreams but would prefer to keep making money by working remotely, learn from my mistakes. Just ask the question, and see what happens!
I have heard PLENTY of stories about people working remotely with their boss’s permission, but for whatever reason, I just never thought that could be me. I guess I never had the confidence or self-esteem to think that I was worthy of such a privilege, or that I deserved it.
How sad is that?!
I got lucky that this opportunity fell directly into my lap instead of passing right over my ultra-oblivious head, but in retrospect, I wish that I had had the foresight (and the self-confidence) to ask for this opportunity myself.
But, at least I did have the foresight to give my notice in a courteous and humble way, rather than throwing my papers in the air, yelling”I CAN’T TAKE IT ANYMORE” and quitting on the spot. So, I think there are really two lessons here:
If YOU are thinking about quitting your job to travel:
1. Consider asking for a remote job option first, because you never know what will happen.
2. Don’t burn any bridges, because you never know what will happen.
As for me, I’m officially location-independent and ready to start making money on the road! Let’s see how this goes…
Have you ever quit a job to travel or follow another passion? What happened? Do you or anyone you know work remotely?
I totally understand how you felt before you talked to your boss…. I’m such an over thinker as well!
It’s great from your boss to give you the opportunity to work remotely – very cool reaction 🙂
Ola recently posted…A Day in Český Krumlov
Yeah, overthinking is probably honestly an understatement. And I know, my boss’s reaction was the best I could have hoped for!
This is fantastic news!! Ahhhh it really couldn’t have turned out better!!! I’m so excited for you!
Emily recently posted…Five Year Anniversary at Disneyland
Thanks, I know!! I got pretty lucky haha.
That’s such great news! I remember being a complete wreck when I gave my notice for a new opportunity a couple of years ago! It’s just no fun to have to tell somebody something like that when they’re depending on you. That’s so awesome that you’ll be able to work remotely though, and that everything worked out even better than you could have planned!
Ashley Lillis recently posted…Wine Tasting in Grapevine Texas
I was totally a wreck, I’m pretty sure I was shaking when I talked to her haha. I really was just so scared to let her down! But yeah, I’m so happy with how things worked out.
Reading this gave me goosebumps! Huge congratulations, I’m so excited for you and seriously, how amazing is your boss?
Silvia recently posted…August 2015 – 1 Month in Norway
Thanks so much!! And I know, she’s seriously too cool.
Wow!! this is AMAZING! you are super blessed to get this opportunity and travel! I wish the best to you as you start your traveling journey! Wish in a couple of years to do the same! You are such an inspiration!
Monica Montoya recently posted…Family Getaway: Welk Resort: Sirena Del Mar | Los Cabos,
Thank you so much!! I feel incredibly lucky that my boss decided to give me this opportunity. I really hope the same thing works out for you, too!
This is so cool! I am so happy that everything worked out for you. I am currently working full time but I am considering taking a longer trip abroad in the future, possibly next year, and I am already feeling anxious and fearful about my options. I definitely read your post at the right time in my life! Thank you for the inspiration.
I totally get that, I was SO anxious about what I was going to do about my job in regards to this trip. My advice is just to stay optimistic, work hard, and find a creative solution if you need to–it’ll all work out one way or another!
WOW. This is awesome. Perfect timing too – I’m putting in my notice next week! (One-way flight to Colombia booked.) That’s going to be great that you’ll have income on the road. I am pretty sure this is NOT going to happen for me (I’m a lawyer and my work atmosphere isn’t very, um, remote-friendly)… but we shall see! Hooray! Long-term travel!
Rachel recently posted…As of Late: Four Things I’m Loving + One That I Dislike
Ahh no way that’s so cool! I can’t wait to read about your trip. And yeah, it probably helps that I’m in marketing and 99% of what I do can be done online. But hey, you still never go what could happen!
Congrats Kelly! I feel like “I quit my job to travel” doesn’t really get examined that much, and while I totally see the appeal of that phrasing, even, there’s always a little voice in my head that asks, ummm? I really related to all the feelings in this post–I’ve always felt bad about leaving jobs, and I’m also at a point in my life where I’m both passionate about stability and adventure. Great post, and again, so looking forward to hearing about Central America!
Yeah, I totally get that. Like it sounds great in theory, but when it comes down to actually having to make it happen, it kind of gets a little more “real” I guess haha. Luckily things worked out pretty well for me, so I still get to have a bit of stability throughout this adventure which I like!
Wow, that is amazing news. Congratulations! What an enormous difference that is going to make in your quest to be location independent. That is so so cool!! What I would have given to have a boss like yours when I left on my travels.
Justine recently posted…This Expat Life: Month 13
Thanks Justine! I know, I can’t believe how lucky I got! I’m still on cloud nine with how everything has worked out.
This is just awesome! I feel like things that are meant to be fall into place, it definitely looks like you are making the right decisions and things are working out in the best way!
Kaelene @ Unlocking Kiki recently posted…Hiking Around A Volcano In Vestmannaeyjar
Thanks! I know what you mean, it’s nice to feel like somehow my decisions are actually working out for the best.
What an amazing blog! We enjoyed reading your accounting of the last few weeks re your determination to see the world! There’s one source of income you will always be able to fall back on and that’s being an adventure/travel writer. Have a wonderful time, keep in touch with all your FB followers and above all be safe! We love and admire your passion. G’nG aka Mary and Bill
Thank you guys so much! I can’t wait to tell you both all about my trip 🙂 Love you both!
Omg, I’m so happy for you! This sounds amazing! Best of luck on your new adventures xx
Christina – CavaforLunch recently posted…Travel Talk with the Aussie Flashpacker
Thank you so much!!
This is inspiring. This point may be coming soon for me as well. I feel like my boss would say the same thing as well. May I ask how much you saved up and what you are doing about your apartment situation? Best of wishes on your move! Can’t wait to hear all about it.
mary recently posted…My Not So Remote Camping Trip
Well I live with my boyfriend, so he’ll still be living there and I’ll still be paying rent while I’m gone, although I’ll pay a smaller amount than normal. So that at least helps with storing all of my stuff and whatnot.
What an amazing result! You must have made yourself really indispensable to your team to be offered this opportunity, congrats! When I decided to go travelling long-term, I initially asked for a sabbatical… but unfortunately, I was the 3rd person in a row to be asking for this in my department and they thought I was one too many, so they rejected my request. I was disappointed at first, but in the end it worked out for the best – I am not sure I could have gone back to my old life (and well, I actually didn’t)!
Camille recently posted…Sigulda, Europe’s Undiscovered Adventure Playground
Yeah, it’s funny how things have a way of working out for the best, even if it’s not what you expected to happen!
what a great story, kelly! something similar happened to me, I loved my job but wasn’t happy with my life.. so I thought it was either STAY or GO. as I explained to my boss, she was like: “do you want to have time off, maybe 2-3 months and then come back?”
I’m right there with you, I need a steady home and income to truly feel independant, that’s what matters most to me. to now have time for myself and to travel is simply amazing – AIM HIGH, you’re absolutely right 🙂
have a lovely day.
Thanks for sharing your story! I love hearing how other people have managed to fit in both travel and stability. Hope you have a lovely day as well!
That’s an awesome story! So glad you were able to retain your job remotely instead of having to quit outright to fulfill your travel plans. Sometimes it is possible to ask for a leave of absence from your job to travel for an extended period of time. My friend did with his Corporate Finance job and another friend did it with his Events Marketing company. Thanks for sharing this valuable lesson with us!
Ray recently posted…Backpacking Belize – Visiting Actun Tunichil Muknal Cave
Thanks for your comment Ray! It’s definitely becoming more and more feasible to work remotely, which is a great option for travelers.
Wow, what a cool story! I quit my job in the magazine industry in NYC in 2008 to go freelance, but that’s a bit different. I have regular clients and outlets, but nothing is ever guaranteed month to month, so I’d say you did it right!
What industry do you work in?
I also am a “part-time traveler.” I work 80 hours a week but travel about two weeks a month for projects (or fun). Still, I have a husband and dog, a house, two condo rentals, a car, etc. I think we’ve managed to figure out the best of both worlds, don’t you? I love having a permanent base to come home to and “stuff” I can call mine, materialistic though it may be.
Kristin @ Camels & Chocolate recently posted…Joining the Biggest Party of the Year in Hungary
Yes, totally agree that having a good balance of frequent travel + home base is a great way to live! I work in marketing, but this particular role was a bit different in that my main job was to manage a website where my company stored internal marketing collateral. Yes, it was as boring as it sounds hahah BUT it was something that I could easily do from anywhere. I actually still work for this company part-time, but my role has changed a bit to more writing-based which I’m super happy with!
I just gave notice to leave yesterday and followed your script almost exactly. It worked out great and they are offering me to come back after a year. Thanks for the help!
That’s amazing!! Happy travels, and congrats on having a job to come back to – that’s a huge accomplishment!