Guest. Mentoring Director and Blogger

It’s been long that I promised to bring over some international guests, so I’m happy to intro our first guest — Sarah!

Hey, Sarah! How should I intro you to my readers?

Hey there, I’m Sarah a mid-twenties woman from the United States. I work for a small program in Indiana that trains university students to be job coaches/mentors for incarcerated teens in our Indiana prisons. I’ve been lucky enough to be able to take my role remote in the past six months and I’ve been working and traveling my way around the globe since about May of 2018.

To that end, I blog at Suitcase Six about sustainable travel for working women. I’m super passionate about being able to fit travel into our lives as women who still have strong careers we’re excited about. I also am passionate about trying to live more sustainably and protect our fragile planet. My favorite hobby is travel and right now I’m on a 180-days-around-the-world style trip, literally working around the entire northern hemisphere. I started in Chicago flying out to Norway and have been going east through Europe, Asia, and back to North America until I hit Chicago again.

(Shameless plug to follow the journey on Instagram @SuitcaseSix or at on the blog.)

Have you ever worked in an office? Why did you decide to change to a remote job?

I used to work in this position mostly in an office at the University, or from my office at home. But I’ve long wanted to travel the world on long-term trip like this. I actually had told my boss (whom I’m very close with and had worked with for years) that I could give her about two years after graduation in this position. Then the plan was to quit and travel indefinitely. When it came time to quit, she offered to let me stay on part-time remotely, and I excitedly accepted. So that’s how I ended up in this current remote-role!

What do you do now? Can you describe your usual working day?

My job now is to recruit and train mentors for our program and to help with all the remote-tasks like running our website, updating the training modules, refreshing our volunteer and staff manuals, and promoting our program on our new social media accounts. It’s called HOPE Mentoring which stands for Helping Offenders Prosper through Employment, so we focus a lot on teaching teens how to prepare for getting a job when they’re released from prison.

A typical day for me starts with checking my email and formulating my to-do list from there. Recruitment and training is a huge part of the process, and our application and training process is really intensive. A lot of my time is spent helping potential mentors get through the paperwork, reviewing the training modules they do, helping our mentors that are actively working with students, and answering questions for potential recruits.

If I work through my inbox in time on a given day, I turn my attention to our other projects. Sometimes this means posting things on Instagram or Facebook to share what we’re doing. Sometimes this means researching and adding helpful things to our manuals or trainings so our mentors are better prepared for the work they do. Sometimes I’m helping with grant submissions or writing manuscripts about the work we do for publication. And typically, I have a meeting or two each week with other people on our leadership team.

Right now, I’m working about 20 hours a week while traveling. I try to do 4 hours a day, Monday-Friday, generally first thing in the morning or before going to bed depending on the time zone and when my colleagues are awake. This leaves the weekends and half-days for travel and exploring.

What skills and traits enable you to do your job? What do people need to know/learn to do a similar job to yours?

I’m a super organized person and work best independently, on most days. Being organized is critical because I have to keep track of 20–30 people who are in different stages of paperwork, applications, training, etc. I have to make sure that I’m following up with where they are in the process, checking in if I haven’t heard back from them, and also attending to any urgent questions issues our mentors might be having.

To that end, I think being disciplined and self-motivated or creative are really helpful traits. I need to be able to manage my crazy schedule while still being available when mentors and applicants are awake back at home (within reason). I also have to figure out what needs to get done without being told — most of the updates to the website, training modules, manuals, etc. I’ve made are ones that I realized needed to be done on my own.

I think the fact that I am so organized, disciplined, and self-motivated are what helped me get this position in the first place. My boss knew that she could trust me to get the work done I needed to and go beyond just what she was asking, because she’s a professor as well as Executive Director for this program. She doesn’t have the time to give me a to-do list every day and micro-manage my work so she needs to know that I can keep myself busy and know what needs to get done to make our program work. When she realized I could do that, she decided it would be safe to let me try doing it remotely where my organization and discipline (and strong communication with her) needed to be at a top level.

More tangibly, I have some basic website design and social media skills, and strong writing skills, that allow me to run our program website and create the documents and materials we need. These are a super helpful skills to have, especially when you’re working for a small program and need to help with a wide variety of tasks.

There are lots advantages of remote working, what were the challenges for you personally when you just started working remotely and how did you cope with them?

The two hardest things for me have been finding reliable wifi when I’m staying in hostel or on the road, and dealing with the time zone differences. This mostly comes into play when I need to have meetings via Skype with colleagues or potential mentors. It’s sometimes really challenging to do when you need to be at a meeting at 1 am in the morning, your hostel wi-fi is down, and there aren’t any cafes open in the area where you can go to work. It just requires a lot of planning and open communication about the situation though. When I’ve been worried I might lose connection during a big meeting, I’ve made sure a colleague was able to cover my talking points in case I got disconnected so they could carry on without me.

What were (if any) your illusions about remote work?

thought it would be a lot easier to travel during the day after I finish work than I’ve found it to be in reality. Sometimes it’s difficult to have the energy to go sight-seeing after a morning spent hard at work. Or making timing work if you need to be at a meeting, but the museum you want to see is only open during certain hours. It’s minor though, other than the challenges in finding wi-fi that I mentioned before, it’s been mostly what I expected. It’s still work and you still have to be able to balance your life like you would at home, just with more temptation to go exploring than I usually had!

What do you enjoy the most in your work?

I really love getting feedback from the mentors or mentees about the impact the program has on their lives. A lot of the student mentees don’t have many supportive role models in their lives, and to have someone who works just with them to cheer them on and support them is huge. The mentors write logs after each session detailing what went on and the progress they made or issues that came up and they make me so proud and teary-eyed almost every time.

I also love being able to come back to my boss after I’ve taken some initiative to change something or improve something and be like “look what I did!” The independence I have in this position is amazing. I’ve always wanted to be doing something where I felt like I was making a real impact or like my work was needed. And I feel that in this position.

Would you ever consider working in an office settled down again?

I would consider office work if it was work I was really passionate about, but I’d really only want to do it if the benefits were great, I had lots of time to travel in my free time, and/or I was working in an office abroad somewhere.

How about the financial side? Are you satisfied with what you’re making with this job? How do you make enough money for all your travels?

Working remotely while I travel has allowed me to pay for my travels when I would have run out of money long ago. That said, this is an entry-level position and it comes with no benefits because of the small size of our program and limited funds from the Department of Correction who is contracting me. Especially now that I’m part time. It’s something I’ve struggled with because at some point I will need to make more money to be able to save, afford healthcare, etc. so that’s something to worry about for the future.

I am super frugal at home though and try to spend money only on the essentials. I had an old car, buy used clothes, don’t spend a lot of money out at events, had a small apartment and minimal bills (I was living rent-free at my mom’s house for a while which was a blessing). I try to save as much money as possible for my travels, and saved for about 2 years to be able to afford this current long-term trip. And when I travel, I try to stay at the most affordable hostels, choose cheaper cities where possible, and save money wherever I can to stretch my travels as far as possible.

Remote work implies some sort of loneliness as you’ve got nobody to chat with at the coffee machine, sometimes you haven’t even got a coffee machine. How do you handle this? Where do you find new people? How do you socialize and maintain existing relationships?

I absolutely do get lonely sometimes. When I’m feeling that way, I make sure to schedule a call with my best friends, boyfriend, or family. I stay in a lot of hostels where it’s a lot easier to meet people too. I’ve also found that doing group tours are a great way to meet other travelers, especially when they’re multiple days in length. Traveling along with strangers for a while quickly turns them into friends. But the great thing about being remote is you can go wherever you want. If you’re feeling lonely, move your office back to home for a bit, or to a bustling café. And consider staying in one place longer — it’s hard to meet people if you’re bouncing from city to city everyday but sticking around in the same place for a few weeks gives you a chance to make some real connections.

Do you think it is possible to make a family while working remotely and traveling?

I definitely think it’s possible. I’ve met a lot of people as I’ve been abroad who have travelled with their kids or partners! I won’t lie and say it’s easy — far from it. You have to have enough job security to make enough money to support yourself, and the bigger your family the bigger the income you need to pull in to make it work. But if you’re flexible, patient, and determined there’s no reason you can’t bring your family along with you while you travel and work.

How about medical insurance and social security when you’re a digital nomad? Have you figured it out for yourself?

I have NOT figured this out yet at all. I’m hoping someday I can find a remote gig with enough benefits that I can have some of this covered. Right now, I am still on my mom’s insurance for a year, and also have a travel insurance plan with World Nomads. But my savings have come to an abrupt halt since I’ve been travelling which is something I’ve got to sort out. Making more money would mean I could file some of that away but as it is, financial security is a challenge for me at the moment.

What advice would you give to the people who are only now starting their careers or start considering it?

I would say don’t be afraid to take risks and do work you’re passionate about. I spent about six months working as a delivery driver out of college while doing this job with fewer hours before the state finally gave me a contract, which was a huge gamble. I turned down a really nice job as a paralegal with much better benefits but way less flexibility. And because of that gamble, I’m getting to travel the world and do a job I absolutely love with some of the best colleagues I could hope for. It might not work out for me forever, who knows, but it’s working for now and I’m happy with it.

Just put your all into whatever you do and work on always improving yourself and your skills. You never know what volunteer gig or hobby or part time job might convince someone to hire you, or how those skills could help you land your dream job! Don’t feel pressured to land your dream-gig right off the bat. Just do your best and give yourself some TLC — it’s hard to not have security but I think it’s harder to feel trapped in a career or city you’re dying to leave and not having a great way out.

And thank you very much, Sarah for being so open and sharing your story!


You can follow Sarah on her Instagram @SuitcaseSix and her blog or if you’re a woman working remotely while traveling, don’t hesitate to reach out to Sarah to feature in on of her blog posts.

If you liked Sarah’s story, share it with somebody who it may inspire and follow me and in my Telegram channel for more remote job stories like this one.