How Working In A Prison Helps Me Travel The World

For the past few years, I have worked in a position for a mentoring program called HOPE. The short version of my job is that I train college students to be job coaches and mentors to teens in prison. This means that sometimes my office is a cubicle on a college campus. Other times, I work from my “prison office” – a concrete-walled room in the school a juvenile correctional facility in Indiana.

I never imagined working in a prison would open up so many opportunities to travel. Still, since the summer of 2015 I’ve visited over 18 countries while working this job. I know my situation is unique, but it’s hard to find a work/travel balance we’re happy with sometimes. I want to tell you how I’m achieving it right now by maximizing my time off, in case it can help you do the same.

My story: From college to prison

Before classes officially started my freshman year of college, I took part in a two-week seminar where I studied psychopathy and how it presented itself in children. I learned about the ways our society treats those with psychological disorders and antisocial behavior. What we were learning and its practical applications to failing US justice and education systems enthralled me. My enthusiasm must have been apparent because my professor invited me to serve as a teaching assistant for the course the following summer. When that was a success, I returned the summer after that.

Three of the Suitcase Six at an Indiana University Tailgate where they went to college. {Melissa, Marie, and Sarah}

During that third summer, before my junior year of college, my professor secured some funding and offered me a position as her research assistant. I began down the path with this bold woman, researching what we could do for the juveniles in our state who needed support to stay out of correctional facilities.

And I thought I was going to try for medical school when I entered college…

My professor, whom I call T-O, has a background in special-education. Years ago, T-O was losing track of students due to their being incarcerated. Following them where they went, she continued her special education work inside the prison. She found that what many incarcerated students are lacking in their lives is positive, caring adults. Like all kids, these students need people who will support them and connect them to resources they need for success. This gave T-O an idea.

Sometime later I joined T-O as her research assistant. She told me she wanted undergraduates to serve as mentors and be those positive caring adults for juveniles. From then on, we began building HOPE Mentoring (which stands for Helping Offenders Prosper through Employment). The goal is to connect undergraduate volunteers with incarcerated juveniles who could use a mentor, and help them develop skills for success in the workplace. Our mentors meet weekly with the students while they are incarcerated and continue encouraging them toward success when they return home.

suitcase six prison to world travel
One of the prisons in which our female juvenile offenders were housed.
Suitcase six prison to world travel
Our HOPE mentors (and my boss T-O, second from the left with the black hair!)

So how does this relate to travel?

For most of my life I’ve loved working with kids. I grew up babysitting, volunteering, and participating in mentoring programs in high school and college. It seemed a comfortable transition to help create a new mentoring program, but I could not have predicted how the work we did in Indiana would lead me to take trips throughout Central America, Europe and across throughout the United States as well.

My boss, T-O, has partnerships with colleagues at the University of Costa Rica doing prison work there too. Lucky for me, this has created many opportunities for international collaboration. In 2014, T-O invited me to spend three weeks working in Costa Rica the following summer in one such collaboration.

My travel dreams turning reality

My high school dreams of traveling outside of the USA were suddenly becoming a realistic possibility. Immediately, my wheels started turning to see how I could capitalize on this invitation. Over the course of the next year, I began planning a trip which would evolve into a 9-week Central American backpacking adventure. My work with T-O has continued, and the mentoring program we began in 2014 has expanded to exist in three correctional facilities across the state of Indiana. Our travel continues to grow too! I am in the midst of planning a HOPE work trip to Norway in May 2018 so we can learn about Norwegian prison systems.

guatemala, suitcasesix, hiking, volcan san pedro
After a hike up Voclan san Pedro in Guatemala.
cursed child, harry potter, theater, play, london
Melissa, Sarah, & Marie at the Cursed Child Harry Potter play in London.

What’s Next?

Since my time in Central America, I’ve traveled a lot – through the UK, USA, Southeast Asia, and Western Europe. Some of these trips have been for work, others for vacation. This trajectory was colored by many other experiences to lead me here – my work in a fair-trade store called Global Gifts, my close friends who comprise the “Suitcase Six,” the people I’ve met on my journeys, and the courses I’ve taken in college. But while I could not have planned for it, it has been my work with HOPE Mentoring that has allowed me to travel the world. In this position, I can pursue my two passions simultaneously – supporting youth in my community as I have been supported and experiencing as much of the world as I can.

It is these experiences which have persuaded me to write on the topics of human rights, and balancing work and travel. My area of greatest expertise is juvenile justice, so a handful of the Suitcase Six posts discuss juvenile justice in places I visit. The hope is that I’ll learn a bit more about each country’s culture and politics. With luck, I might become a better human rights worker, expanding my understanding of the field’s serious global issues. I can only imagine it will continue to enhance my work and travel.

Suitcase Six prison to world travel
Views from my last trip to Portugal.

A few things about this position that allow me to travel:

  • I’m a temporary contract paid hourly, and can only work a set maximum number of hours per week. I also don’t have benefits.
    • If I want to take a lot of time off, I don’t get PTO so there is less of “penalty” for my employer when I take a leave of absence.
    • This also means that my job isn’t secure AND can cost me a lot of money out of pocket for insurance.
  • My boss understands my love for travel. T-O travels herself and we talk often and openly about our personal travel goals.
    • While your boss might not love travel as much as you do, they’ll never know it’s your priority until you tell them. The more you talk to your boss about fitting travel into your life, the higher chance you have of coming to a compromise.
  • I work super hard when I’m on the job and make myself an asset. This means a few things.
    • My boss doesn’t want to lose me and have to train someone else. I’m in a unique position because I helped start this organization and know it better than anyone else, spare her. BUT this applies for any job. It may seem obvious, but work so hard your boss can’t stand to lose you. Take initiative to do things you notice need done, even if it isn’t asked of you. Show up on time. Be creative. Your boss may be more likely to grant your vacation time if your performance is top-notch.
    • I plan in advance to leave as little work as possible for coworkers. What I do need covered, I outline clearly with specific instructions on when and how to complete each task. This helps my colleagues feel less disturbed by my extended absences.
  • I complete a large portion of my job tasks behind the screen of a computer. This means with a laptop in my backpack and decent wifi, I can complete most of my work abroad. At this point, I don’t work much when I’m abroad, trying to enjoy vacation. BUT, ideally I’ll transition to working remotely for HOPE starting next May.
    • I check into email every few days on most trips to respond to any urgent items. Usually,I also offer to spend a few hours each day working remotely so it makes my extended absences more palatable to my boss.

*My salary and lack of PTO mean that my trips are around 3 weeks in duration, on a basic budget. Work is normally chaotic before and after I return, for a few weeks. I generally don’t work while I’m abroad, so this isn’t remote work.

suitcase six prison to world travel
Standing on Victoria’s Peak with Marie in Hong Kong.

How can you apply this?

Clearly this is not a situation most people find themselves in and it may not play out this way for everyone. However, I’ve taken advantage of a lot of situations that required a few nervous requests to my boss for more vacation time – I had to ask. If you’re working a job you love but want to travel more or are searching for a new career, here’s a few tips for maximizing your vacation time:

  1. Find a job with a lot of computer work or work that can be done remotely.
  2. Let your boss know early and often you want to see the world.
  3. Be willing to be flexible about hours, or make sacrifices other job perks to gain more travel time.
  4. Make it easy for your colleagues when you’re on vacation. (But not so easy that they don’t need you back…See tip five!)
  5. Kick ass at your job. Work hard enough that nobody could imagine replacing you.

Want more travel tips on working abroad? Get our freebie “30 Terrific Jobs for Women Who Love to Travel the World” when you join the mailing list.

You’ll get suggestions on thirty jobs from six different fields with opportunities for global travel. Each job in the downloadable PDF also links to an article on how to get started in that profession, or an example of where you might work!


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