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How To Have A 10 Year Vacation (I’ve Had One!)

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I’m a solo travel expert, solopreneur and founder of Wanderful Company, a labour of love inspired by 15 glorious years of non-stop traveling alone. 

Equipped with nothing more than a suitcase, a one-way ticket and an incessant desire to be happy, I’ve gone from one solo travel adventure to the next for almost one third of my life to countries including Argentina, Brazil, Italy and France.
I'm Kirsteen!
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xo, kirsteen

A 10-year vacation or should I say workation (vacation while working) is possible. I’ve had one and I am now onto my next. Welcome to freedom.

Where do I sign up? How can I have one too? What do I do to begin you may be asking? I’m guessing those questions may have crossed your curious mind and is prodding it with a generous sprinkling of enthusiasm. Quite frankly, who wouldn’t love the idea. Freedom you must be thinking, 10 years to do what I want, OK I’m sold, am virtually packing my bags, got the flippy floppers on, and snorkeling mask on my head, ok, done…now tell me how…

Admittedly if I’d seen the same blog post years ago, too damn right I would have opened it. My world would have stopped like a factory line making white bunnies and out pops one that’s pink. I’d have pressed the pause button, cos pinky winky just got my undivided attention.

Well, lovely, I can’t give you a 10-year vacation personally, and gift it with some pretty bow and sparkles, or a cute pink bunny, but I can share how I’ve had my own decade of vacation bliss having created it with the help of my ever-inventive mind.

You see, travel (especially solo travel) is one of the most life-giving, energy-boosting, intellectually stimulating things you can do. Not only does it generate incredible levels of excitement but you feel alive. And I don’t just mean alive, I mean ALIVEEEEEEEEEEE. And on a little side note, isn’t that the point of life?!

It awakens every cell of your body as if in a nightclub soaking up boogie-woogie dance hits while stunt doubling Travolta high on a disco ball and never wanting to come down. Heck, you would stay up there for months if you could. We all know the feeling of planning and packing for a well-deserved vacation after months in the office with simply a coffee machine for the day’s entertainment. (That reminds me, gotta do a post on this lol).

What if you could trade that corporate life for 10 years of sun, sea, and satisfaction? (ps no coffee machines in sight but you can have a cutie Italian hand-deliver it with a smile lol). Oops sorry, am digressing, I blame those Italians for being too damn cute. Anyway back to my point, would you do it? Really do it? No pretending? Be honest, do you have that ‘I can do anything’ belief? Just sit for a few minutes and imagine someone had just handed you that opportunity? And said pack your bags, you’re leaving in a week? Would you have the guts to do it?

Well, lovely, if you are serious, the opportunity already exists, you just have to want it enough. That’s the choice you and only you can make for yourself. Are you a bubbly vivacious Miss In or a tame and same Miss’ing Out? And there’s nothing wrong should you opt for the easy exit. We all have our own personal paths to take and that’s ok. So calm those jets if you prefer vanilla to pistachio. Even a solo traveler has to partake in a scoop of vanilla on her wandering trail.

Fortunate are those who take the first steps

paul coelho

Why take a 10-year vacation?

Why not?! Who said in the rule book you couldn’t. You’re free to do what you want. With respect and some tough love my friend, you’ve ONE life, live it! Nobody is forcing anyone to work with a 60-minute office commute twice a day or be a bunny in headlights as you see the Monday morning never-ending emails pop up from the inbox like meerkats on speed.

And while we’re at it in tough love delivery, nobody said you couldn’t have a 10-hour lunch if you please. We all know the famous quote ‘Rome Wasn’t Built In A Day’, that’s because they were too busy enjoying life and having a 10-hour lunch lol. Smart cookies me thinks of those Italians. Oops am digressing again. Back to the point, if you don’t enjoy work, why are you wasting precious time doing it?

I wasn’t immune in the past btw. I had to move away from the daily grind myself to find balance and enjoyment and luckily and gratefully I found it. Or should I say destiny hand-delivered it to me and placed it into my happy little mitts. What I do have is an abundance of self-belief. Et voila ma petite chou, if you have that, you can do anything including the ‘right time right job’. (more on this in Module 3 of Solo Travel Masterclass). And does it matter what the job is as long as you enjoy it?!

May I add, don’t ever be thinking or let anyone else make you think you’re some kind of lazy loser Lucy just because you want 10 years me-time? You earned it babe. Don’t forget that all those who work their pretty little asses off are doing it mainly for the money to go traveling in the first place. Just saying. And besides, you’re just asking for a ‘pocket money advance’. lol.

So don’t defy fun gravity, and just fast-forward that hot little ass to the end goal. ie FUN NOW. Give up needing validation from others because they will try to stop you because secretly they want to do it too but can’t. And why? Because comfort zone is way too cozy and they feel better if you stay ‘in society’s sameness’.

Being on the receiving end of this myself the day I resigned, those same Debbie Downers who thought I was crazy and laughed have most likely been doing the same job all these years while I’ve been having the time of my life. So who is laughing now?! I cannot help but feel smug, they’ve had on average 60 weeks of vacation in the last 10 years versus my 520. lol. Joking aside, I wish them good luck, they just couldn’t see my vision and why would they. Nobody had done it before. And, that’s ok. It’s the life they wanted, and we all have the right to choose how we live.

So getting back to the how?

There are 2 options. Work doing something you love (workation) or throw caution to the wind, take some savings and just go.

I choose the latter but it’s not for the faint-hearted. Work if you wish while vacationing but if you don’t have a job, it will find you if it’s what you want. When I think back, I used to think it was miraculous how things just found me. But now, I believe that destiny simply knows what you want and is guiding you to it.

Take decisions from a clear head. THAT IS A MUST. (and in case you hadn’t seen, I coach on workation – click here. I also go into the real detail of job hunting and workation in Solo Travel Masterclass launching very soon). I couldn’t spill all my secrets now, could I. lol.

So lovely, just imagine waking up here in Tuscany on workation and having this as your office for a month (best start slimming now because they have 10-hour lunches and you’ll need another month to digest lol. But heh, Italian help’s at hand, there’s always Florence to sprint walk some shopping). Wtf are you waiting for my little tiramisu?

To realize one’s destiny is a person’s only obligation

paul coelho

The most important thing when financing a 10-year vacation is to find ways where you never feel you’re actually working. One such way is to teach English online. Many years ago, in the UK I had the chance to do my TEFL (Teach English as a foreign language) Certificate. Amusingly, this was years before I actually left the UK and in hindsight, it was one of the best things I did given how many language agencies want and expect it.

Teaching is a LOT of fun! Not only that, but some clients become friends. And of course, we can’t forget the humor and laughter at ‘the odd slip of a vowel’ and you realize they had fun by the ‘bitch’ when the beach would have sufficed. hahaha. And let’s soak up the idea of a cup of wine (copa), I’ve had a few cups in my time. lol. I can honestly say teaching has given me such freedom and flexibility to work and travel anywhere. Plus, having that daily contact with people you get to know is a boost.

If teaching isn’t your thing, you may want to think of learning a skill that’s in demand in preparation for leaving. With remote working easier than ever before and many companies being flexible to allow workation, there are a plethora of options online vying for your attention. PS Silicon Valley giants KNOW the incredible power of happiness in growing a successful business. If a happy person can attract a happy life, imagine the potential of a team of passionate people? Believe me, as time goes on, companies will be fighting to offer happy people workation jobs from anywhere they please.

As a little gift, click on this video by the talented Kylie Flavell for some Italian workation inspiration! To think that some have this as an office! Lucky peeps me thinks!

In my 16 years of nonstop solo traveling, nothing was planned and has worked out one small step at a time. So, you will have guessed by now, I do work too. You see, not a lazy Lucy badass. But crucially, I do a job I really enjoy with clients who make me laugh and I never have the feeling I’m working. All from the comfort of my workation laptop at a stone’s throw from the Med.

So, there you have it my friend, things to think about and a happy workation life to live. Nothing on this planet stays still. If you’re not moving towards more happiness, you move away from it and this planet won’t wait for anyone.

When all is said and done, I’ve accomplished something I never set out to and which broke the mold. One woman, one suitcase, and a whole lot of fun along the trail. And for that, I feel immense satisfaction and pride in what I’ve achieved. Nothing was handed to me. I manifested a life I could never have imagined and are the memories I will cherish forevermore. That is living wanderfully…


If you’re are asking how do I start workation and experience the benefits myself, please contact me to request a consultation. You can also click here on Solo Travel Masterclass to find out about this solo travel course which is one-of-a-kind and a lifetime of knowledge and wisdom in one easy-to-follow course.

If You Like This Post, Also Check Out:

Traveling Alone: Top Tips From A Solo Travel Expert

Is Solo Travel Lonely? No. Here’s Why

A Few ‘Wanderful’ Links…

Forbes: Why Traveling Is Good For Your Health

Aerial Views of Tuscany

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hi, i'm kirsteen


Your new BFF & Travel Coach.

I'm an ex-Corporate girl who gave up a very successful career in the UK for a dream life traveling alone. Why solo? To do what I wanted,  where I wanted, and when I wanted. That was 15 years ago when I left with nothing more than a suitcase and an incessant desire to be happy. I've never looked back...

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xo,kirsteen