My Career Break Trip: What I Did Right, What I Did Wrong and What I Wish I Would Have Known

Sergiev Posad, Russia

Hindsight is always 20/20, right?

The passage of time always seems to give you a new perspective and now that it has been more than two years since I first left to travel around the former Soviet Union, and a year since I returned, I feel like I can look back at my time on the road with more clarity than I had immediately after returning. As I reflect on all of it, there are definitely some things I think I did right, some things I did wrong and a few things I wish I had known beforehand.

Kiev, Ukraine

What I Did Right

I visited the places I wanted to. As challenging as it was at times, I am glad that I stuck to my guns and forged a unique path by spending my career break traveling through the former Soviet Union.  Many people suggested at one time or another that I switch it up and I’m glad I didn’t listen.  There are so many places that I would love to return to, I know I made the right decision in staying the course.

I brought 2 pairs of jeans. It’s the endless debate among backpackers – whether or not to travel with jeans. Well, I had two pairs with me at all times (and at one point even 3 pairs!) and I would not do it any differently. Even in the coldest, wettest places, they dried within 24 hours and with 2 pairs, I always had one pair to wear while I washed the other. Jeans were durable, fashionable and they allowed me to blend in much more than fancy travel pants or khakis would have.

I ate at McDonald’s. It may be taboo for many travelers, but McDonald’s just brought me much needed comfort and yummy French fries from time to time and I’m not ashamed at all that I probably visited a McDonald’s in every city I visited that had one.

I volunteered. Two of my best experiences were volunteering through the Armenian Volunteer Corps in Yerevan and teaching English in the Zerafshan Valley in Tajikistan. Both experiences gave me the chance to get to know the countries and the people much better than anywhere else I visited and provided an opportunity to enjoy a little stability and routine on the road.

I learned the language. Learning Russian made everything about my trip so much easier. Once I got comfortable with it, I was able to get around with confidence and I was able to connect with locals much more than I would have been able to if I didn’t speak the language.

Tatev, Armenia

What I Did Wrong

I went too fast. This is kind of giving in to all those voices who kept telling me to slow down, but in retrospect, I kind of wish I would have. Why kind of? Well, I still wanted to get through all 15 former Soviet republics and I wouldn’t change that at all, so going slower would have meant taking much longer altogether. I just didn’t feel like I had the luxury of time as I was traveling – the money was limited and I needed to return and look for a job again at some point. But as I think back, I know there are places I would have loved to have spent more time.

I rented out my condo instead of selling it. Unfortunately, my timing was not great and I simply wasn’t able to sell my condo before leaving on my trip. While I was able to pull in enough rent to cover most of my mortgage, I still had to cover my assessments each month and I always had in the back of my mind that I may need to deal with some sort of repair from thousands of miles away at any moment. I also returned home earlier this month to a condo that barely felt like home anymore; there is so much work to be done to bring it back to the condition it was in two years ago.

I didn’t pay off my student loans beforehand. Really, I should have just taken care of my student loans much earlier. I didn’t pay them down as much as I could when I was making an excellent salary, so they still lingered over my head as I left to travel.  Between the student loans and the mortgage, I had fixed expenses that I could only sustain for so long from my savings, so I never really felt free as I traveled.  If I was to do it all over again, I would have been 100% debt-free before leaving to travel.

I didn’t make enough effort to stay in touch with friends back home. One of my biggest frustrations during my trip was how little my friends back home seemed to care about my trip. And by the time I returned, I felt like I had almost no real friends left in Chicago. But, I really have to take part of the blame for that. At some point, I just became detached – I was so disappointed by the lack of response to my monthly update emails that I just stopped sending them and effectively gave up.

I didn’t take enough pictures. Actually, I think I just edited and deleted too many of the photos I took. I got into the habit of uploading my pictures each night to my netbook and then editing them and deleting the ones that I just didn’t like. I also resized them to save storage space. But now, as I go back and look for pictures to use in posts, I consistently think “didn’t I take more pictures than that?” or “why don’t I have a picture of that?” And then there was that time that the Royal Geographic Society wanted to buy one of my pictures from Turkmenistan but I didn’t have the original version and the size I had saved was too small for them.

I didn’t write enough. Yes, I wrote a lot of blog posts, but I neglected my journal. I didn’t capture a lot of my personal, in-the-moment feelings and I also didn’t take enough notes on specifics about things I did and places I visited. As I started trying to write an e-book relating to my trip, I realized how much I had forgotten not even a year later.

Seven Lakes, Tajikistan

What I Wish I Had Known

I wish I had known how easy it would be to find a job afterwards. I don’t mean to sound like I’m bragging, but as anyone who followed along with my journey knows, the fear of not being able to find a job again after my trip hung over me like a dark cloud throughout my trip. I definitely thought about it too much and if I had known I would end up with five job offers within three months of returning, I think I would have traveled a little looser.

I wish I had known how hard it would be to change careers afterwards. While I found a job again with relative ease, I did not fulfill my initial goal of using my travels to switch career paths. My year of travel didn’t hurt me when it came to applying for jobs, but it also didn’t help me the way I hoped it would and I ended up settling for a position back in my old field – something that I was determined not to do when I departed in August 2011.

I wish I had known to bring plastic hangers. I read this tip on a blog last month and just thought it was genius! Hangers take up very little space and can just be placed on the bottom of your backpack. And then you can take them out to hang laundry when it’s drying. I can’t tell you how many times I was in dire need of additional places to hang wet clothing and the clothesline with suction cups and hooks that I brought with me just didn’t do the trick. Next time? Hangers.

I wish I had known that Charles Schwab is better than Capital One. If you missed my post about all the issues I had with Capital One, you can read it here. The consensus among American travelers seems to be that Charles Schwab is the way to go.

I wish I had known how hard it would be to return. Seriously, if I had known how difficult it would be to adjust to life back in the United States and how quickly I would be itching to travel again, I may never have come back. While I was exhausted and ready to be home a year ago at this time, the thrill of being back in the United States soon wore off.

I wish I had known that things would work out. There’s really no way to ever know how something will turn out, but overall, I spent a lot of time on my trip worrying. It wasn’t until the very end that I started to have a little faith that things would work out ok – I wish I had been able to worry less and enjoy things more along the way.

18 thoughts on “My Career Break Trip: What I Did Right, What I Did Wrong and What I Wish I Would Have Known”

  1. Pingback: Weekend Reads | The Travel Hack

  2. Katie I love how much I can relate to this! The biggest obstacle while on the road, is the unknown back home. How will I pay for this back home, how will I get back in the game once home, why does no one from home seem interested in what I’m doing?

    Great Post!

  3. Love reading your blog.It’s ok if you had regrets.Life was not meant to be perfect.But it is really nice that you shared all of this so that we can learn from it and not make the same mistakes .thanks Katie.Great blog.

  4. Great article, Katie! I just resigned from my job last week and I can share the same fear of having to start over, like you had. I did sell my house this summer, so I am glad to hear that you thought that was a good idea. I leave on my one year trip on 20 January! I’m excited and scared…all rolled into one!

  5. thanks for sharing your great experiences. I travelled to Georgia last year and to Armenia and Georgia this year.I love these countries and their people. I always take inflatable hangers with me on trips.

  6. Great post Katie! As always, I love how completely honest you are with your writing. As someone who heads home next month after nearly 18 months away it’s really helpful to hear about what it’s been like for you.

  7. I almost always wish I had traveled slowly when I finish a trip. It’s a difficult balance: If I go too slow, I regret not seeing certain things, but if I go too fast I feel like I miss out on the nuances of the experience. My favourite is “I wish I had known that things would work out” – I tend to over-worry as well, but in the end, everything really does work out ok.

  8. What a great post! I especially love your last point, about how you wish you had known that everything would work out. I feel like traveling long-term and taking risks like this are great ways of teaching you that constantly, the trick is to remember that things don’t just work out on the road, they work out wherever you go. Sometimes that means things don’t go to plan, but at the end of the day, more things will be right than wrong and that’s the most important thing!

  9. Just came back from a 4 month trips myself and I can’t agree more on things you mentioned above. It’s not hard to get back in real life, it’s just hard to accept that I am no longer roaming like a free bird.

    I am thinking about doing a long ex-USSR trip as well in the near future and take the opportunity to learn Russian. Did you take any class or use any book/software to study before you head out?

    Thanks for writing Katie, love reading your blog.

  10. Although you have regrets, at least you will never regret NOT taking the trip of a lifetime 🙂 There are always things we want to change in hindsight, but you forged your own path in the end!

  11. I love everything about this. I love you for being a JEAN backpacker… I love you for eating McDonalds… & I do wish you had known about Charles Schwab, because they are amazing.

    Oh & don’t get me started on how hard it is to return home after travel. Still dealing with that today… it’s just not easy at all.

  12. I agree with the going too fast, I only traveled for about 3 months back in 2005, and I regret going so fast. I took a ton of pictures though! I want to travel again so badly but now I have a job, a boyfriend (who is not keen on long term travel, longer than a month) and a dog!

  13. Agreed with jeans and McDonalds! and boo to not taking enough photos, staying in touch with friends and the difficulty of returning.. I’ve been very guilty of these as well

  14. I can relate to the picture regret – and I haven’t heard anyone else say it. I managed my pictures the same way as you…downloading often, editing and deleting as I went…and now I wonder why I have so few! I’m sure that many that I deleted thinking they weren’t ‘good enough’ would now look spectacular with the passing of time and distance. Live and learn – I now take far more pictures and don’t get rid of many at all!

    Great round up Katie!

Comments are closed.

Scroll to Top