Reinventing Your Life with Travel

I may have mentioned that I’m turning forty this year. For a decade and a half or so, I rolled my eyes at the “mid-life” crowd and their annoying propensity to over think everything, their inward focus on “the crisis,” and their apparent over emphasis of particular milestones.

Then I caught up to the curve. I had a bit of a mid-life crisis, looked back and realized the party was half over, looked forward and realized that I really am standing at the top of the hill, and all of a sudden, I got it. I got a two handed grip on the fleetingness of life, the precariousness of relationships, the difficulty of balance, the importance of feeding my own soul, and the all-fire, hell and high water, burning passionate need to make damned sure I’m not wasting this time I’ve been given. There’s nothing quite like reaching the potential half way mark to cause a girl to reevaluate, reassess, and recommit to living and breathing her dreams.

Apparently, I am not alone. The piece I wrote a few weeks ago, about your twenties and Setting Yourself Up For The Life You Want, resonated with the younger crowd, as I’d hoped it would. But then there was that guy on Twitter, @rafat:

So that got me thinking. Of course life goes best when lived intentionally from the outset, that’s obvious, but the reality is rarely that well orchestrated. I think it’s safe to say that the majority of folks hit the wall at some point, look up from their carefully crafted norm and think, “How in the hell did I get here, and what am I doing, anyway?”

And the most frustrating part of all is that everyone around us seems to accept this soul-sucking realization as par for the course and they just keep plodding.

We think we’re doing all of the “right things,” and then we turn 35, or 40, or 45, or 50, and we realize we’re not where we thought we’d be. We’re not happy. We’re not “living the dream.” We’re “stuck.” And the most frustrating part of all is that everyone around us seems to accept this soul-sucking realization as par for the course and they just keep plodding.

Is this life?

Is this all there is?

Is this what it means to be an adult and a responsible member of society?

I would submit that the answer is, “Yes,” to the vast majority, but a wild and resounding, “HELL NO!” to a growing minority to whom passion means more than security. Are you looking to make that left turn and really live the second half of your life? Rafat, my friend, this one is for you.

Taking back control

Taking control

The good news is that 40 is the new 20, or so they tell me. In so many ways, I’d rather be forty than twenty. Gone is the angst and the drama of trying to figure it all out. I no longer give a damned what anyone thinks. I know who I am. I like who I am. I understand how to play the games: I’ve won most of them, and I know which ones truly don’t matter.

The upside to forty is that we have resources we didn’t have at twenty: connections, relationships (both business and personal), experience, confidence, perspective, and money. Okay, not everyone has money, but the odds are good that at forty you have more than you did at twenty when all you had to work with was a high school education and only that evenings and weekends gas station job on your resume. At twenty you had the luxury of time and flexibility. At forty, you have the luxury of something to work with as you reinvent yourself.

When my husband quit a six figure job with a division of Apple six years ago, at thirty-seven-years-old, people thought he had lost his mind.

The conversation between his boss and the higher ups went something like this, “What do we have to do to get him to stay? How much is this going to cost?”

“Guys, this is not about the money, he’s following a dream.”

The boss was excited for us. We were reminded that he could come back within two years at the same benefits package, “if it didn’t work out.” We sold a four bedroom house, two cars, and most of what we owned. We packed up four school-aged kids and informed them that “home” was now defined by a big Hilleberg tent and transportation was the two wheeled variety as we set out to ride our bicycles through Europe and North Africa for a year.

That was six years ago. We’re still traveling full time.

Overcoming hurdles

Too much stuff

When we left, we were a mess. We’d spent two hard years planning and actively working on our launch plan, which was a little more complicated for a family of six than it is for your standard boots and a backpack gap year, for one. We were both working full time at our real life jobs and putting in another thirty hours a week to get the dream off the ground. It was exhausting.

Getting on that airplane was like breaking the surface after the deepest free dive you’ve ever made and filling your screaming lungs with air when you were sure you weren’t going to make it. The relief: I can’t even tell you. My husband is a creative. He appears to be a computer geek, but that’s just the outward expression of his puzzle loving soul.

I can’t even imagine what life would be if we hadn’t made that break, if we hadn’t flipped conventional expectations the bird and pursued our passions instead.

It wasn’t until well into the fifth month of just pushing pedals up and down with nothing more to life than camping, kids and the Euro Velo, that he grinned at me over lunch one day and announced, “I hear it. I hear music again. In my head, like when I was a kid; I have a whole symphony playing in here while we ride.”

It took five months for him to get his soul back. It was another four months before he started working again, this time on his own terms. I can’t even imagine what life would be if we hadn’t made that break; if we hadn’t flipped conventional expectations the bird and pursued our passions instead.

So how do you do it?


How do you go from stuck to pursuing your dreams?

How do you use travel to reset a life in your forties?

How do you let go of everything you thought you wanted to pursue with clarity what you’ve discovered matters most to you?

Great questions. Hard questions. How does anyone do anything? You just do it.

You’ll get to the point where the pain of not living your dream is greater than the comfort of your status quo. You’ll come to understand that every day you waste is gone forever. The fear of end of life regret will begin to wake you in the night. You’ll look at your kids and realize that they’re almost gone and that you can’t get them back. You’ll find your why and it will light a fire in your soul that will either kill you, or transform you like a phoenix from the ashes. You’ll be forced to the brink of a decision that will determine the course of the rest of your life, and you’ll have to make that choice.

Making the choice is the hardest part. Once you’ve decided, committed 100% to your dream, it’s a done deal. The details will work themselves out. The Universe will conspire to help you forward. You will do the necessary work, because you have to. Your world will change.

I can year you already: “I’ve got a great job, I’ve got a partner and a couple of kids, I’ve got responsibility, debt, commitments, family stuff.” I know. Me too. All of it. So here’s the question: are you going to keep trading your very breath for less than the passion of your heart? Are you going to put off the only thing you have: right now? Are you going to trade your soul for things less worthy than the life you were born for? Many will. Many do, every day. I cannot.

The responsibilities, the challenges, the relationships – all of those things are negotiable and manageable. They can be worked into the fabric of your dream. Family life and long term travel are not incompatible. Education and adventure are not mutually exclusive. Career advancement is not necessarily traded away when you choose to restructure your life in such a way that you work to live instead of live to work. We’re making more money now working approximately half the time that we used to. We know people who make far more than we do and work far less than we do as they travel. It can be done.

Can you drop it all like a hot rock at forty and just buy a plane ticket to somewhere? Well you could, but it might have catastrophic consequences. You have a career, a home, and a family. You have responsibilities and debts, perhaps. These are all things that you’ve chosen; they are things that you’ll have to work through and around and with as you redesign your life.

Grown-ups take responsibility. That’s what we do. For ourselves, for those around us, for what will come after us. Reinventing yourself at forty doesn’t mean that you destroy your family, declare bankruptcy, quit saving for retirement, and become a drain on society.

No. Reinventing at mid-life is all about finding more ways that you can give back, to yourself first, and then to those who matter most to you and the rest of the world. By cutting loose from the “stuck” places and creating freedom for yourself, you put yourself in a position of being able to change the world, internally and externally, in big and small ways.

Having the courage to really live your dreams is a gift to the world. It is a gift to your partner and your children. It is a gift to those who look up to you in your career world.

So where do we start?

Start them young


At forty it’s unlikely that you’re an island. Talk to the people in your life – friends, family, partner, children. Build a dream together. This requires risk taking, vulnerability, negotiation, and compromise. Take the risk of being known, of admitting that you’re feeling stuck, that you hate some aspects of the life you’ve chosen, and that your dreams are bigger than your status quo. Talk.

Get Real

Take stock in a serious way of what you have to work with and what your limitations are. How much will you have to save to take a year completely off and travel? It’s not just about what your basic budget for Europe vs. Southeast Asia should be, it’s about life insurance, schooling costs, investments, health care, debts and all of the difficult, under the hood financial realities that should not be cut loose like an old boat. Your realities will go with you when you travel, so plan for that.

Next, get real about what is possible in your individual situation. You might have aging parents, someone with a long term illness, children with special needs, or any number of other complicating factors. There are seasons of life for certain things, and if there is one lesson midlife is teaching me, it’s that embracing those seasons and the challenges they come with is the only path to happiness or dream building.

You have to work with what you’ve got.


My Uncle Dick is famous for the 7 P’s: Proper Prior Planning Prevents Piss Poor Performance. By forty you should be an expert at patience and perseverance (two more P’s, do I get extra points for alliteration?!) Take the time to plan, carefully and properly.

Odds are that following your dream does not affect just you. It took us two full years to prepare to take our leap, and we don’t regret a second of that time. We built our dream together, developed the skills we’d need, prepared our children to be excited and enthusiastic instead of feeling unsettled and displaced. We saved money. We invested money. We worked on developing other income streams. We downsized. In daily life we began practicing living our dream until one became the other. Don’t despise your planning time, embrace it.


It sounds completely hokey, but it’s 100% true: The moment you quit saying “if” and begin saying “when,” the game changes. Set a date for your dream. For us, it was April 1, 2008. We set that date in February of 2006, on an afternoon’s drive through the mountains of New Hampshire. We began talking (and acting) differently about our plans when we had a departure date set in stone. We told people. We designed our plans leading up to launch with that day in mind. It held our feet to the fire in a way that “someday” just doesn’t. We left March 24, 2008, a week ahead of schedule.

Build Community

This is a tough one sometimes. It is likely that most people you know now are going to think you’ve lost your mind. If you’re lucky, they won’t say it to your face. Why would someone quit a solid job, sell a “dream house” and wobble away on bicycles into the world, literally dragging four children behind them? Why indeed.

Community is key. It’s too easy to give up on your dream without other folks cheering you on, screaming at you to RUN and leading by example.

There are some people in your life that you’re never going to be able to explain it to. There will be others who get it instantly. Find those people. Build a tribe of dreamers around yourself and feed your soul, feed your dream, with their adventures and their input. You may feel like “the only one,” but I promise you, you are not.

Contact me, I’ll hook you up with a mind blowing array of forty-somethings who are rocking the world. They’re my friends, and they’ll inspire your socks off. Community is key. It’s too easy to give up on your dream without other folks cheering you on, screaming at you to RUN and leading by example.


Seriously: just go. If you’ve been talking about this for a decade, shut up and put your money where your mouth is. I’ve learned to ask, “What’s the worst case scenario?” Short of death, the worst case scenario is that we lose it all and have to start over flipping burgers at McDonald’s at forty. That would suck.

Could we do it? Yes. Would I rather have had my dream and an epic crash and burn story to start over with, or would I rather have safety and soul-sucking security? Everyone will answer that differently, but I suspect you know what my answer is. The reality, of course, is that you’re unlikely to be reduced to the absolute bottom because you’re forty, you’ve got brains, experience, grit, determination and a skill set that can be repurposed if you really need it. You’re not twenty with just “gas station” on your resume.

Would I rather have had my dream and an epic crash and burn story to start over with, or would I rather have safety and soul-sucking security?

You might wake up tomorrow with breast cancer, a brain tumor, or some other life path altering bump in the road. Don’t bet your dreams on unknown tomorrows. Take what you have right now in both hands, and run with it. There is not going to be a better time than now to build your dream, even if you have to wait a year or two to launch it.

You’ve got a limited number of days. Stop wasting them on less than your dream.

You’re forty; you’re younger and healthier at this moment than you ever will be on any future day. You’ve got a strong mind and a strong body. You’ve got the people you love. You’ve got a limited number of days. Stop wasting them on less than your dream. Take a deep, deep, cleansing breath; now dive deep, swim hard, and then harder, down to the very bottom, through all of the things that must be sorted, organized and restructured. Touch the bottom, feel the depth of what you’ve created in your life so far and then take that hard left turn toward the surface and kick with all of your might. Your lungs are going to burn. Your muscles are going to scream. Your head is going to feel like it’s exploding, but when you break the surface and you take that deep breath, it’s going to feel like morning, it’s going to feel like coming alive, because you’ll have broken free from the depths and you’ll be floating on the surface of the world.

Talk to me, people: Where are you at forty (ish)? Where do you want to be? What’s stopping you? How can I help?

Need more inspiration to get you out on the road? Check out the following articles and resources:

manifesto - value private transformation


Leave a Comment

  • Paul Elverstone said at 2014-02-05T16:03:15+0000: A great article of a subject very close to my heart. Basically: everyone does what they think is right instead of what they want because they've been given a model of 'life' from a place of authority - a teacher, a parent, a clergy and so on. And then they fear what they don't know and take comfort in what they do know, even if it is something that they don't want or like. Any utopian vision becomes blurred by materialism. Nowadays we call this 'society' How do you break out of that? Not easy. For me it was a life-changing event. For some perhaps something a little less dramatic but certainly an epiphany of some kind. It is a cliche but it holds (some) water: youth is wasted on the young. I got it at 35. I consider myself quite lucky. Now that I've found my place, I consider myself very lucky. Took the long way around though...
  • Amy Nixon McClure said at 2014-02-07T15:51:07+0000: “Come on, mom!” my 11 year old son yelled back to me, as I gingerly picked my way along the muddy creek bank. He was already scaling the side of the acclivity, which gave way to what appeared to be a vertical wall of mud, broken up by large vines which may or may not have been attached to solid ground. I had agreed to, or rather, pursued doing this after I heard him talk about “falling from a 70 foot cliff” when he was playing at a friends house. “Wow!” I said. “ A 70 foot cliff, and in the neighborhood just over from us?” I said. “This I gotta see”. So he and the friend eagerly helped me navigate as I drove to the point-of-entry. We crossed some City property, where we may or may not have been trespassing, and then made our way to what arguably did appear to be a rather large, maybe 30 foot ravine, although standing at the bottom looking up, my 40-plus year old legs said definitely 70, if not 80 feet. My son looked back at me again and said “It’s not as bad as it seems! You can do it! You are the coolest mom for doing this!” Well, there was no going back now. So up I went, following the two boys, praying no one fell, and especially that no one fell on me. When we reached the top, we were rewarded with a wide open space which may or may not have been someone in the neighborhood’s (very cool) backyard. A small pond covered in duckweed stood quietly in the middle and we tossed pieces of wood and stone in the murky water to guess the depth. We determined it was indeed very deep, likely containing remains of Cretaceous era mammals. It was a beautiful, sunny day in the mid-70‘s as we made our way out of the yard and back along the trail which lead to where our car was parked. I drove the kids back to my house where they continued to play outside. I had laundry to do, dinner to cook and of course, Facebook to check. This is when I read the article on travel and adventure. I was inspired by what it said, and I do like to travel, but I had to think about this one for a time. Packing up and leaving behind the life I have established just isn’t for me. For reasons that come from deep down, I value stability and community and my home. I don’t want to leave it. I think there is a vast amount of adventure in all the details around us. People are fascinating, so I like to learn their stories. I am blessed by books and art and experiences to the point where there just isn’t enough time in one life to take it in. I really don’t think you have to pack up and hit the road to find adventure. Just like the 70-foot canyon right across the road, there are fabulous things to be discovered within our reach, every day, if we have the presence of mind to see (and an 11 year old to guide us) :).
  • Jen McNab said at 2014-02-05T23:08:33+0000: Oh Jen I so needed to read this today! Thank You! xxx
  • Rachel Walmsley said at 2014-02-08T19:14:10+0000: I'm right there, right now, at 36, knowing this is my time to be brave and follow my heart not my head. I'm struggling to articulate exactly what it is this dream of mine, I can feel it, but I can't quite see it yet. Your article had me holding my breath for a few moments as I felt someone talk directly to me. Thank you for your inspiring words. I have just started getting to the 'talking' stage, but sadly for the first time in my life, I'm not really surrounded by the people that could help me make sense of this, i guess this shouldn't stop me, so I will begin talking about it, and hearing what it is that will sustain me when I take everything else away. I have some time on my hands as I have a contract to finish, but I'm encouraged by your words to enjoy the planning time and to build my dream now even if I have to wait a little time for the launch :) I am grateful that your article arrived in my inbox at the very moment I needed to read it. Thank you so much for a little push in the right direction.
  • Dawn Dugle said at 2014-05-01T00:35:42+0000: Thank you so much for this post. It certainly came along at the right time for me, as my wandering spirit has been nagging me in the past few months. There are so many people who don't understand someone who is completely "all in" on their dream. They can't understand how someone would travel solo, or move 3,000 miles away from home, to live on a tiny island. They get jealous when you talk about the amazing things you've seen and the amazing people you've met. I hope these friends find their own enlightenment, so they too can find their joy of adventure!
  • David Hutchison said at 2014-02-05T19:43:33+0000: Jennifer, we can so relate to this. Especially the exhaustion of getting to the launch date, ours was September 3rd, 2012. My wife and I took a similar leap and haven't looked back. I am am all the more impressed with your story as you brought kids, it's just the two of us mid-lifers. The hardest part is making the decision to go, but once committed you're in the flow. That's not to say that everything has been lovely sunsets and adventure, we've the same ups and downs in life, but we wouldn't trade the past 18 months for anything in our previous careers, lives, etc. We're writing about our experiences on our blog, read if you like. Cheers, Hutch
  • Stacey Ebert said at 2014-02-05T20:07:29+0000: Jennifer-what a fabulous article and even better story. We had a similar couple of experiences and are working towards a new adventure as we speak. I too will turn 40 this year and agree wholeheartedly with you-life can be reinvented and experiences are priceless. Would love to chat one of these days. Some of my story is on Thanks for sharing yours-your family is living an amazing life. Cheers.
  • Jordan Meredythe said at 2014-02-06T05:16:07+0000: Often those who you get it will be your fellow tribe of travelers! And these thoughts of yours, especially under GO, remain true with aging. Even more so. I would enjoy having more of an in- person community though I do have an online one. Don't plan overmuch, the unexpected can be awesome!
  • Kerry Ascione said at 2014-02-26T13:26:28+0000: I am way ahead of you, in age that is! I'm 50, but it feels more like 30, only much better. I have no regrets since finding a way to travel with my family six years ago. Right now we have only managed to travel internationally for 4 - 6 weeks every other summer, but I am motivated to do more. So, your article is very motivational and inpirations; I'll mull it over some more. I think you are phenomenal to do what you have done! Your kids are so lucky to have such unconventional and brave parents. I'm sure you know how valuable your kids global education is for them. Thanks for a great post. Kerry Ascione, The Trusting Traveler.
  • Lena Michals said at 2014-02-05T20:29:26+0000: Love, love, love your article. Thank you! I have been planning now, slowly but surely, a trip starting on July 1st, 2016 with my daughter (now 4) and my husband: first around the USA and Canada in a RV for a year and then slow travel all around the world starting with South America for another 3 to 4 years. I can't imagine myself waking up one day when I am older and have the regret of not have followed my dream.
  • Del Lloyd said at 2014-02-06T11:37:23+0000: Great article! My husband and I (45) are 5 months in to our RTW trip. I posted this on my FB page to inspire all those who are just getting through their lives..I feel like I am just getting my soul back and starting to feel like "me".. I have no idea where this is going to lead (or what I want to do when I grow up).
  • Julie Jane said at 2014-02-06T04:02:03+0000: Awesome article. My partner (51) and I (42) are heading off on our own 2+year adventure in 8 months. The countdown has taken a while due to family commitments but it is almost here and the excitement is building! Cannot wait to move from corporate life to long-term traveller.
  • Donna Petersen said at 2014-02-07T04:30:23+0000: Wow, all I can say is, I am turning 55 and I am at that wall, smashing it with bloody hands. Maybe I need to climb it instead of trying to break it!! Wish me luck.....and thanks
  • Barbara Hallanger said at 2014-02-06T05:23:08+0000: Well, I'm 62 now and I first came to China when I was 39 and began living my dream. I have been back and forth, but mostly China is where my heart is so here I stay, living my dream and loving it. Oh, I was born in America. You remind me of myself when I was your age.
  • Colburn Deb Shindell said at 2014-02-06T04:32:52+0000: Perfect timing - we are 7 months in to our adventure and just starting to discuss what our new life looks like. Fully agree that committing to he process was key for us to make the break - and so very happy we did.
  • Sherry Bonnell said at 2014-02-07T12:41:40+0000: Took the plunge in November. Freedom 55.