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Road Warrior

Saying 'yes' to solo travel

Many of us can relate to the idea of picking up everything and relocating to a different country—whether it be for work, for love, or for the sheer adventure. But it’s a decision that doesn’t come easily for everyone. Canadian Jennifer Holmes has been on five continents and over 50 countries, and for now, is calling Turkey “home.” Jennifer is a digital nomad who works in marketing consulting and as a certified professional empowerment life coach. She is also passionate about helping other women make their travel dreams a reality.

“With some exceptions, solo travel is a very different experience for women and men. For men, they are going to a destination to see something, to explore or discover something. For women, it is more of a self-discovery, to push their own limits and learn about themselves—it not about the destination, it is about the journey. So, the decisions we make to go are very different ones, Jennifer said. “Women have trouble putting themselves at the top of the priority list, they have trouble with the guilt factor, with the judgment factor and this notion that we are supposed to be doing it all—working full-time, raising children, paying the mortgage, and if we take two weeks off and are no longer doing what we are responsible for, it makes women feel irresponsible,” she added.

"So many people approached me and said ‘you are living my dream but I am afraid, how do you start, what do you do?’ I was afraid too, but I got to a point where I just had to move forward and go through with it, but some people need help to do that.”

Jennifer rapelling in Brazil, segwaying in Spain, and seeing the pyramids in Egypt (courtesy of Jennifer Holmes)

“Friends and family can be the worst people to get advice from because they have their own ulterior motives that will make some women decide that their own needs are not as important. In traditional life, everything feels competitive. With expats, and women travelling solo, they are all helping each other; if I meet other women on the road traveling solo, we help each other out without question—it is not a competition. What these women are going through to follow their dreams, or their hearts or to learn about themselves is very inspiring. I see it as an interesting dialogue, and if someone benefits as well, then that’s wonderful.”

Culture and upbringing play big roles in the decision to travel solo she says. "If you haven’t been taught to be independent, or to be very close-knit or co-dependent, it will change how you travel. In Turkey where family is everything, I might get the question ‘How can you leave your daughters?’ It shows you the difference in our societies. In western societies, you are considered a good parent if you get your kid off to university and if they move back in with you as adults, you are considered a bad parent or your children are lazy or that you are coddling them. Here, it is not like that at all. It is a contrast and at first, it made me think I was a bad mom. I have this conversation and explain the difference in our societies, and I think they understand. At the end of the day, I don’t need their approval, but it is nice to get that insight from other cultures and know more about theirs. 


How Jennifer came to her current status as a digital nomad was through combination of disposition, timing, and luck. Despite possessing all the trappings of a so-called happy life, Jennifer found herself disillusioned by it. “When I was a child and someone asked me what I wanted to be when I grew up, I said ‘a butterfly’ so I was always very curious, and wanted to flutter around. I was taught like many people in our society that happiness is achieved when you go to university, get married, buy a house, have kids get a corporate job and a dog—and the rest is taken care of. I didn’t find that to be the case for me; I had all those things but I hated my lifestyle. I was disenfranchised and realised this didn’t make me happy— that it was a lie.” Gradually, things deteriorated with her husband and they divorced. Her children got older and were not reliant on her, so she decided it was the right time to shed her material belongings and live a more minimalist lifestyle.

Eventually, an opportunity arose to leave her stressful corporate career with a nest egg, and she started consulting. “I realised that I could be doing this anywhere because the clients weren’t in my home city. I sold everything I had left. The day I made that decision, I thought, ‘How am I going to find someone to go into this apartment, how am I going to sell my car, how am I going to sell all my furniture,' these things are just logistics, but they are a lot of work. As soon as I made that decision, a friend of a friend was moving to my city, and they needed a furnished apartment; in one phone call, I was able to find someone to take over my lease and buy all my furniture. With one other phone call, I sold my car—then I just went.” 

Jennifer goes back to Canada every six months to visit her daughters. “When I do go back to Canada, we spend quality time and I feel I have a better connection to my daughters now than when I lived in the same city as them. All of my close friends are very supportive, and they miss me and wish they could do the same thing, but their circumstances don’t allow it.” 


The most important thing about travelling solo and full time is being present. “The thing I noticed when I was in Canada—we don’t pay attention to our surroundings—we are all zoned out. When you are travelling, you need to pay attention because you are not in your element.”

“When you are on your own—if you are a half-hermit like I am, you may turn into a full hermit, and that is not healthy. Typically what I do to take care of that issue is every time I get to a place, I find a public transportation pass, a gym where I can get a monthly pass, and go explore where my grocery is, the local pharmacy, what the local food delivery apps are within the first 24 hours of arriving. I go to sleep, and wake up and am happy to explore.” 

Managing expectations is a big thing, especially when you don’t have someone’s company to consult or comfort you. Loneliness can be an issue especially for people who are not naturally social. So, before you decide to sell all your things and travel the world for an indefinite period of time, define what kind of person you are, what your values and beliefs are, your strengths and limitations, otherwise you will slowly deteriorate. 

Self-awareness and analysis are important. If you aren’t comfortable, you have to be flexible to change plans or be prepared if your plans change unexpectedly, as they did for Jennifer. Initially, Jennifer was travelling with a company that catered to remote workers. The format was group travel where they changed locations every month, managed the logistics for transportation, room, and board for the travellers.  Part-way through their itinerary, the company went bankrupt, and Jennifer found herself having to fly solo and figure out where to go next. “It was a revolving 60 days, where I had the next two places figured out, and then I would just go with the flow - mostly it was geographical. Some people have a different method and only want to stay somewhere a couple of weeks. I find going somewhere for a month gives you a big discount on AirBnB, transport, gym passes, and gives you a chance to get to slow down and know a place.” 

Practically speaking, there is a certain list of criteria that Jennifer has when she selects where to go. Since she works remotely, she checks if there is consistent wi-fi, if there will be social opportunities, places to exercise and get fresh air, and whether she can find housing that she will be comfortable in, and is within her budget. If some places are outside of her budget, she has to make sure to balance it or trade-off for something else in the moment, or down the road. “Because of overcrowding and over-tourism, I’ll go off-season. I went to Split, Croatia in October—the weather is still beautiful. The local businesses make the most of their money during tourist season, so if more people travel during the shoulder season—just a few weeks, it would help local businesses, the environment and it would help give a better experience. You get to enjoy the sights without a big crowd or big wait, you get better discounts on airfare, lodging, tours.  If you are looking for a more immersive experience—avoid the bus tours, and anything with a microphone, and take a walking tour. Sometimes you’ll get the guide all to yourselves, and many of them are free. As a general life hack, for shopping, or dining, if you go first thing in the morning or just before the typical rush, you have the place to yourself, if you go later it can be a nightmare.” 

“I am really glad I’ve done this. It works out for some people, and for others, it doesn’t. Life can be difficult, and I’ve had a lot of tragedy in my life, but it led me to where I am now. I wouldn’t take any of it back. I’m glad that I am here and am grateful for all of it. Hopefully, other people will think about that and realise that not everything will be good all the time, but you have to appreciate the good as much as the bad, and not to think ‘I need to be happy all the time,’ because you won’t be. It comes in waves and that is one of the things I have learned the most, and what I’d like people to know the most. When something good is happening, we have a tendency to avoid bad things happening at all costs, so we won’t take risks, we won’t challenge ourselves or get out of our comfort zone, and then we box ourselves into this limbo. This is a problem that people should keep in mind – understand it may not be fun all the time, but there will be good times, and you need both to have a full experience.

For more information about how to prepare for solo travel, you can visit solotravelerworld.com, which is a great resource for solo travel tips, safety advice, stories and destination. If you would like to connect with Jennifer, you can do so at LinkedIn.