Caroline Keylock is a strategic consultant who specializes in luxury, fashion, and lifestyle. She also writes the blog Masters of Many, which chronicles individuals who are seeking alternatives to the traditional work-life balance. She is currently traveling the world with her husband and baby to find a life that works for them, and is writing a book on long-term family travel, to be released next year.

Caroline represents the New Adult Backpackers, one of twelve sub-types explored in our latest trend report, The New Adulthood. For more on the New Adults, the micro-generation that’s redefining growing up, download the full report.

On working abroad

We had discussed as a couple, prior to having kids, taking a stint off work and traveling. Once I was pregnant we talked about it again. It made me think: why are we waiting? We lived in two places at the time, London mid-week and Worthing on the south coast on the weekends. We’d already decided that we were going to move permanently to Worthing and sell the place in London, but originally we were thinking we would use that money to do more to our house, and save the rest of it.

When I was pregnant, it made me feel it was now or never. I’d seen a couple of other people traveling with really young babies and I thought that we could do the same. Even though lots of people said, “Your son is not going to remember anything,” we were both convinced it would be a huge influence on how he grows up. And he’d have two parents, 24/7. It shouldn’t have to be a restriction, having a young baby. It just makes you see things in a very different way.

Masters of Many.

On traveling

We began our travels in New Zealand. We had a car and we camped all around the north and south island. The first few weeks were definitely a big challenge, but more of it was as parents learning to coexist 24/7 together. Before, I was on maternity leave and doing my own freelancing, and Ben had gone back to work, so we had quite well-defined roles, and then suddenly you’re together all the time. That’s difficult in the beginning, but you get into a routine, and you realize quite quickly that kids are so adaptable. As long as you relax and are flexible and find your roles in doing things, it’s fine. In that respect, it’s easier than a lot of people perceive.

Since then we’ve been to Australia in a camper van, and Japan, Cambodia and Thailand living in hostels and Airbnbs. You realize that your baby works around your life. However, we still have a routine, like everyone else does at home. We have a bedtime process, we know the times of day he’s likely to have naps and plan what we do around it. If we have to do a big driving stint somewhere, we will time that around when we know he’s likely to sleep.

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On experiences versus things

When we were first away, it took such a small amount of time to be less focused on belongings. We realized how much we didn’t miss the things we had at home. We’re not staying in expensive places, we’re living in a pretty frugal way, and we’ve both always had strong beliefs about kids not requiring nurseries filled with toys, that they are better off playing outside.

On combining travel with work

After six months we sat down and talked, and said that we’d like to both freelance remotely so that we could be location-agnostic. We didn’t see ourselves traveling at the pace that we had been forever. We want to live for six months or a year in one place and then go somewhere else new.

The main driver for both of us is working flexibly, so that we can see Otis and not feel like we’re missing out on him growing up because we’re working five days a week, with a big commute.

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Instagram: @mastersofmany

I fell into freelancing five years ago, thinking it would be a temporary thing, and realized I really liked it, and that it was a great way to work that afforded me a lot more control. I do work I like and can work when and where I choose.

On entrepreneurialism

Our generation came out and said: “This isn’t quite marrying with the expectations we were brought up with.” We’re a generation that has technology integrated into our lives, and suddenly we realize it’s feasible to work remotely.

The make-up of families has changed so drastically that it’s forcing people to re-examine what used to be the set-up: 2.4 children, dad goes to work, mum stays at home. There’s been much more focus on women doing well at work, but those women having kids are not necessarily welcomed back at work at the same level, or with enough flexibility for them to do simple things like pick their kids up from school. That’s forcing a change—both genders want a career, but if that isn’t possible or compatible with seeing their family, it makes them think about doing things like starting their own business. For me, that is one of the biggest factors that forced a wave of entrepreneurialism among women in particular.

On the trend for adventurous travel

Some of the markers of adulthood are changing in cities like London because people are having kids and buying property later, because they can’t afford to do it earlier. When you put traveling in the mix, there is a wave of people who have seen their parents retire and maybe get a little bit screwed over on their pension, or they’ve put everything off until they were 65, and those people now wonder what they are waiting for.

The trend of the family sabbatical is a growing one, which is slightly different to what we’re doing because we are working now, but that idea—of just because you have kids doesn’t mean life has to be over—goes hand in hand with a lot of people having kids later in life. They’ve already been quite independent, probably have a decent amount of money, already love travel, so the idea of all that going out the window when you have a child is being questioned.

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I still think that it is at the niche end of behavior. Eighty or 90% of the people I know that have kids might have been very adventurous travelers in the past, but their family travel every summer now is a lakeside in France. That’s a lovely holiday—by no means am I saying that’s a bad thing. Traveling the way we are is quite hard work. That’s the reality, and it’s a reality that gets missed by a lot of the blogs that you see, which make it look very Instagram-friendly and beautiful. There’s no pictures of the fact that you reached four o’clock in the day and you’re tired and can’t move, because the baby is teething and you didn’t sleep, yet you got up and walked for 15 miles that day and have been on the go for 12 hours. That’s the reality, but seeing amazing new sights every day with your family is such an amazing experience, it’s all worth it.


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