I do a lot of crazy, risky things.
In my mid-twenties, despite a bad economy and an excess of nay-sayers, I quit my ad agency job and started a business.
A year or two later, I ditched my permanent address and hit the road with that fledgeling business and my small dog.
And about six months ago, I quit that lovely little business, which had supported over a year of full-time travel, and started a new kind of writing career.
The kind of writing career that let me tell soul stories instead of brand stories. One with editors and agents instead of clients. One where I’d be doing the thing that I had wanted to do since I can remember: write creative stories that change people’s lives. No advertising agenda. No client revisions.
Each of these changes felt enormous, life-altering.
And each of them came with an influx of hope and an undercurrent of fear.
I remember bursting into tears in my therapist’s office when I decided to start my business. Not because I was scared (even though I was), but because a faint hope glimmered in the distance. Hope that I wouldn’t have to trudge endlessly through 80-hour workweeks, making other people rich for the next 20 years. And, most importantly, hope that maybe I really could live a self-directed, balanced life.
Similarly, the thought of leaving Denver behind for a life of indefinite travel left me breathless with hope. Again, I was scared, but it wasn’t fear that leveled me. It was hope. Hope that maybe I could dig my way out of my depression. Hope that life maybe didn’t have as many rules, as much black-and-white/all-or-nothing as I thought. That maybe, just maybe, all those cliches about taking the road less traveled by and jumping off the edge before you see the net could be right.
And now here I am again, six months into a new career. Working hard. Hoping harder. Still not quite there yet, but not giving up.
Just like those other journeys, this one has been an emotional one.
The initial idea—that maybe I could make a living doing the thing I love most, that maybe I could live a more balanced life, work a little less hard, that maybe everything so far had led up to this beautiful moment—left me breathless with hope and gratitude. And, of course, fear.
When I talked about fear, I mostly talked about finances. I wasn’t breaking even yet. How much time could I give myself to start breaking even? What were my financial backup plans?
It’s funny that I was so obsessed with income, because losing income isn’t really what I was afraid of.
Brene Brown, in her book Daring Greatly, talks about how we feel most vulnerable when life is good, not bad. We look down at a sleeping child and think “Oh my god, something could happen to this precious, currently-peaceful person that I love.”
That’s the nature of vulnerability. When we love something, when we’ve got something worth fighting for in our lives, we subsequently start to fear losing it.
And here I was, allowed to live in my favorite place in the world (against all the odds), spending my days writing stories, having absolute freedom to set my own schedule, go where I will, and live how I like…and suddenly I was scared shitless.
It was easier when I quit my full-time job. I had so little to lose. I was working so hard and feeling so exhausted. And I quit slowly, gathering clients on the side before diving in full-time.
It was easier to start traveling too. I had a little more to lose: a growing, successful business. But still it was a simple matter of only planning a month ahead and being willing to come back if the business started to fail on the road. All I had to lose by leaving, really, was the depression and anxiety that had been dogging me for years.
This transition has been so much harder for me. So much scarier.
Because now I have something to lose. I have Switzerland and travel and freedom and joy. I had a growing freelance business that was, after three years, finally feeling easy and comfortable and like all the hard work had come together.
It felt like those game shows where you win $1,000 and have to decide whether to keep it or wager it. Then you wager it and now you have $10,000 and you have to decide whether to keep it or keep wagering it, working your way up toward the million.
Some people look at those shows (myself included so much of the time) and think, “Hey, you’ve got $10,000 more than you walked in with…walk away!” Others think “What have I got to lose? Either I walk away with the big prize or I walk away with the same thing I walked in with…nothing. It’s not a loss. It’s either better or the same.”
This transition was like that. I already had more than I’d dreamed of. In time. In freedom. In stores of joy.
Was I wagering all this happiness for a little more happiness?
All this fulfillment for a little more fulfillment?
Was this the beautiful secret of life—that if you are willing to keep taking bigger and bigger risks, you can eventually live exactly the life you want to live, do the work that makes your heart beat, change the world just a little bit, and pass away someday knowing that you did everything you could to live and love fully?
Or was I being foolish and ungrateful?
Still, I erred on the side of wanting more joy, of hoping that my life could have a bigger impact, of believing that it is possible to succeed yet again.
And so, with the exception of one very serendipitous copywriting project, the last six months have been about building something new. Approaching new publications. Pouring tears, sweat, and love into the book proposal for The Good Girl’s Guide to Living a Badass Life. And, most of all, pouring time and passion into my new, unconventional Italy guidebook—the current focus of my time and effort.
These are the kinds of projects that take scores of time up-front and hopefully pay for your efforts later, which makes them even scarier, but also endlessly hopeful.
Because I could fail spectacularly.
I could pour months of my life (not to mention my savings) into this Italy book with its beautiful, authentic, useful interviews and its classy design and its crazy marketing plan—and it could sell a handful of copies.
Or I could succeed spectacularly. I could watch my ability to create useful, beautiful things become a real livelihood. I could pour all that time and passion into it now and watch it pay off for months and years to come, changing the way people travel and funding my life as I take on my next passion project.
Even selling 1500 copies would feel like a wild success to me. Sometimes that number seems insurmountable. Sometimes it seems ridiculously simple.
And so this is the emotional story of my first six months as a full-time travel and inspirational writer. A story of taking big risks, working really hard, holding onto hope with both hands, and being scared shitless sometimes—but moving forward anyway.
In just a month or two, the book comes out. And with it comes a measurement of my ability to make this work, to be a full-time writer, to make my biggest dreams into realities, and to create something beautiful that helps people have fuller, richer lives as well.
I’m hopeful. I’m scared.
And I guess that’s how these things go.
The book is officially out! Want to buy a copy or just read more? Click here.