After 13 months working in software engineering, Erin Osterfeld took a career gap to take back the reins on her life and find a true passion. She left her senior management job and set off on a campervan trip with her boyfriend through the USA, Nicaragua and the Dominican Republic.
The adventure has led Erin to pursue a new chapter in life. She is now embarking on a career change into money coaching and financial independence via her new business, Miss Financial Freedom.
In this interview, Erin talks about why she turned down an offer of sabbatical leave for the trip, how minimalistic travel methods have altered her life perspective, and the inspiration behind her new career venture.
What were you doing for a career before you took a travel break?
I worked in software engineering for 13 years at a Fortune 20 company. I carried out various roles, ultimately ending up in middle management.
Everything they say about middle management is true. The boss pushes down his directives for us to persuade the organisation to adopt. The engineers are unhappy with the directives, advocating for more freedom to do what they feel is right. Middle managers are very much caught in the middle, receiving complaints from both sides.
It’s a tough place to be, and it definitely wore on me.
What inspired you to take a travel career break, and what did you hope to get out of it?
Although I really enjoyed most of my tenure, the stress that came with a constant expectation of putting the company first really wore on me. Any notification from my phone put me into a mild panic. I took sleeping medication 4–5 nights a week, and when I did manage to sleep I grinded my teeth to the point I shaved off the top of six of them and got lockjaw.
I was earning a good income, but it came at the expense of my health. Finally I decided there is no point to retiring early if I’m not healthy enough to enjoy it. It was time to change my priorities.
I decided to take a minimum six months off work. Anything shorter than that and I would have just been thinking about my next job. My career gap was about getting back to living again.
I wanted to rid myself of all expectations and just be free for a while. It was my chance to get out from under the rock I’d been living and see what else is out there.
“I haven’t had a single moment of regret about my decision to leave.”
How did you approach the situation with your workplace?
I created my exit plan about nine months before I actually quit. I wanted to pay off my debt and build a slush fund for my career break, which I coined “Retirement 1.0”. When I finally told my boss I was resigning, he took the news well.
My reasons for leaving centred around the desire to travel more while still young and healthy, and getting to experience what other career options were out there. After all, I had only worked at Kroger, and I was there for all 13 years of my career.
After I shared my reasons for leaving, he offered a sabbatical as well as new roles that would allow me to travel more. I thought about these options for a day before deciding I was not interested in either of them.
Although the sabbatical sounded appealing, our company had not previously offered sabbaticals. For a large corporation with its share of red tape, I was skeptical it would come to fruition anytime soon, if at all. As far as the travel role, it too was only an idea, not a real position. Not to mention that travelling for work is a lot different to travelling wherever and whenever I wanted.
While each of these were good ideas in theory, I felt like they were too uncertain for me to deviate from my exit plan. I was ready to move on, and each of these were going to take weeks, if not months, to put into action. I politely declined, thanked the company for the growth, opportunity and support throughout my tenure, and stuck to a two-week notice.
When I shared this decision with my boss, he was shocked and disappointed, and further tried to entice me to stay. Our HR lead even called me after the conversation because it was so intense. Had I not been executing my exit plan for so long, I may have wavered under the pressure. But I am very happy to report I haven’t had a single moment of regret about my decision to leave.
How did you plan and save for the trip?
Although I wanted a shorter timeframe to leave my job, there were financial perks (bonus, stock vest) to stay a total of nine months from the point I decided I was going to quit. I also knew that if I still had debt during Retirement 1.0 or if I cashed out investments, that would stress me out. So I decided to use those nine months to tackle two financial goals: pay off mortgage ASAP, and save for Retirement 1.0.
I had been paying off my mortgage ahead of schedule, so I only needed about four months of salary to finish paying it off. The next five months were solely about creating a separate savings account that would be my Retirement 1.0 slush fund.
I didn’t know exactly how far these savings would take me, but I knew I’d be able to take at least six months off. How fast I spent the money would determine how long the break would be. Now, eight months later I’m still going strong. It looks like I’ll probably find my way back to work around the 12-month mark.
Aside from financial planning, I didn’t really make any travel plans. Because of the stress of work, I felt like I had no creative thought or energy to make any plans beyond what was absolutely necessary. I needed to leave before I could find enough space to think about what I wanted to do with this unique opportunity.
What preparations did you make at home and at work before leaving for the journey?
I have a longtime roommate, so I was very fortunate to get to leave my house without any major concerns. She would be there to alert me to anything out of the ordinary, and was also willing to help with basic home ownership tasks like mowing the lawn. This really helped me be able to spend a significant amount of time away from home.
What were the standout experiences of your travels?
My boyfriend and I had both dreamt about someday travelling the country in a campervan. Before buying one, we did a dry run spending a week in Iceland in a campervan. We both loved it and neither wanted to kill the other, so he bought one the month I quit my job. We named it Trusty Rusty and began our adventures through the US.
We got to enjoy autumn in the Great Smoky Mountains, and most of winter in Florida’s warm sunshine. We watched rockets launch at Kennedy Space Center, hiked gator-ridden trails, spotted bobcats, armadillos, dolphins, bears and manatees. We even stumbled upon a historic missile base in Everglades National Park, and skied the mountains of Big Sky, Montana.
The simplicity of campervan life created a much-needed mental reset. I didn’t need “all the things”, just an adventure and great company. The freedom to go where we wanted, always having our accommodation and bare necessities with us made each trip a delight.
“This experience reminded me that I don’t have to be in a big, important job to make an impact.”
Did you find any aspects of long-term travel difficult, and if so, how did you adapt?
I didn’t really do any long-term travel, but rather lots of short (~1 week) trips. Also, having the campervan as our accommodation wherever we went made it feel much less like we were away from home.
Our biggest learnings were about how to make the van become liveable. We had early floods in the interior of the sleeping quarters, nights so cold we could see our breath, and dealt with condensation on all inside surfaces. None of these were terribly miserable or difficult though, so they all ended up adding to the adventure.
What life lessons did you learn from your travels that you would never have learned otherwise?
One of our trips during Retirement 1.0 was a mission trip to the Dominican Republic. We joined a two-day house build led by Youth with a Mission and built a home for a family of five. Having the opportunity to provide something so basic yet life-changing sticks with me. I’m so incredibly fortunate to hail from a country, class and family that has never had such basic needs go unmet. Not one time in my life have I worried about where I would sleep at night or if it was safe.
This experience reminded me that I don’t have to be in a big, important job to make an impact. Sometimes all you have to do is be willing to get your hands dirty. Going on mission trips is something I’d like to incorporate into my life going forward.
Have you developed any particular skills on your travels?
While I definitely picked up a bunch of skills throughout Retirement 1.0, I think the most valuable lesson I learned is to remember that I am in the driver’s seat of my life. While working, things had slowly but surely gotten more stressful. Over time, I had forgotten how good life can be.
These last few months have been so enjoyable, I want to make sure I keep a better pulse on my happiness when I re-enter the working world, and adjust when it starts to get unbalanced again. This is a promise I’m making to myself, and I’m grateful that my time away from work has helped me uncover its importance.
How do expect your travel experiences will influence your lifestyle when you return home?
Travel has always been deeply impactful for me. Getting to experience new cultures, lifestyles and historically-rich places surpass my expectations every time. I have an appreciation for how others do things differently, and I strive to welcome differences in my everyday life.
The parts of my life that have been lived in a bubble of like-minded people have been predictable and uninspiring. Seeing and hearing firsthand how others live life their way is invigorating. Their energy is palpable.
When I return to my fairly routine life, these experiences remind me to embrace the uncertainty of living beyond our society’s checklist for life. In going off-script, which is where life actually happens.
What are your hopes and dreams for the future?
I’m getting to experiment with all kinds of new career prospects, and have found true areas of passion. I have both a financial independence blog and a travel blog, the former of which I’m looking to continue long-term.
Although I love travel, I’ve found that I really wanted to tell everyone how I could afford to travel, and help them make good money decisions to let them travel more. After all, travel has had such an enormous, positive impact on my life that I want everyone to get to experience the growth that can only come through immersing yourself in other cultures.
Additionally, the amount of people my country (USA) living beyond their means is appalling. Questions hover about the ability to retire or even pay for a minor unexpected bill. Living with a cloud of uncertainty hanging over one’s head creates so much stress. It’s a terrible way to live.
The feeling of not having to worry about money is the most freeing feeling in the world. I want to help everyone get to experience a life this free. That is the goal of my financial independence blog.
“Don’t quit on a whim and expect it to be amazing.”
What advice would you give to other people considering taking time off work to travel?
Create a plan to leave that suits you, then execute. Don’t quit on a whim and expect it to be amazing. It’s important to understand your motives for leaving, what you want to get out of your time off, and address the potential stressors that might prohibit you from fully enjoying yourself.
I knew that carrying debt through Retirement 1.0 would stress me out, and make me feel like I needed to get a job. And while I wasn’t sure how much I would spend while I wasn’t working, I wanted to be able to afford 6–12 months without an income. Anything shorter than six months would have me constantly thinking about job prospects and applications.
If you create an exit plan that’s centred around these three factors, you will have an incredible journey without regrets.
If this interview inspired you, read more career break stories in our series of interviews. Start planning your own adventure with our guide to taking a travel career break or sabbatical and read up on the career skills that travel can help you to develop.
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