Greetings from Iceland! I’m writing these words from Reykjavík, in between my attempts to meet with as many people as possible to promote Tales of Iceland over my 5 days here.

My time in Iceland has been fantastic. I’ve had the honor of meeting the SEEDs staff (the organization we’re donating 5% of book profits to), visiting the Reykjavik Grapevine office (Iceland’s free, alternative English paper), having coffee with Alda Sigmundsdóttir (author of wildly popular The Little Book of the Icelanders), and meeting with a representative from Icelandair’s marketing department. I also found out that Eymundsson, Iceland’s largest bookstore, will start carrying Tales of Iceland this month!

Seeds Office
The lovely ladies at Seeds Iceland. We’ll donate 5% of book profits to their environmental projects.

Writing these words feels surreal. I’m sitting in the very same chair, in the very same cafe where Stephen (author of Tales of Iceland) and I first imagined working together. (The cafe is C is for Cookie, and it’s my absolute favorite place to grab a soup and a bottomless cup of coffee and get some work done.)

The specific idea for a book about Iceland had not yet been hatched, but there was this feeling that the two of us could do something interesting together if we combined Stephen’s writing magic and my ridiculous enthusiasm for entrepreneurship and building something at the intersection of travel, media, and technology.

It’s surreal to be here for more business than pleasure. While that would bum most people out, this is, to me, exactly how I’d prefer to spend my traveling days. I enjoy traveling as a means to explore, escape routine, and practice living in the present, but even more so than that, I love working with people all over the world to build something interesting. It’s all so surreal because this is exactly how I envisioned my ideal life to be. I have many, MANY miles to go, but in a way, I feel like I’ve met with a small degree of success unexpected in common hours. It’s exhilarating. And it reminds me of the resilience and power of the human spirit when one wants something badly enough.

Touching Down in London Town 

Before coming to Iceland, I had the opportunity to speak to about 55 people in London for an Escape the City event. The title of my talk was “How to Escape and Build a Life Traveling the World.”

While I’m no stranger to public speaking, this was a new experience for me. I’d never had to command a room full of people who paid money to see me ramble for two full hours. I was incredibly nervous (at least on the inside) for the few days leading up to the event. I had typed up a dissertation-length speech of everything I would say — all the wisdom and lessons learned over the past year — to the people dreaming of doing something different in their career and life. I wanted it to be perfect. I wanted it to be useful. I wanted to spew inspiration and brilliance.

I tend to over think things (blame my introspective nature), and I could tell I was doing the same in anticipating my talk. So while I wrote down a bunch of talking points and lessons learned, I decided it was more important to keep it casual and interactive. I’d tell my story from Consultant to Slow-Traveler to Book Publisher, but leave a majority of the time for Q&A and group discussion.

As I told my story, I tried to embed a simple take away: The first step is the toughest, and it’s mostly a mental one. And while I didn’t go over all my talking points in London, I think it’d still be useful to share them here. Below is everything I planned to say in London.

Escape talk

Everything (I Wish) I Said in London 

One of the most important things I want to stress tonight is that there is a paper-thin difference between you and me right now. The barrier between people who are dreaming of “escaping” their corporate jobs to pursue something more meaningful, and someone like me who’s decided to jump, and is in the midst of doing it, is mostly a mental one. The difference is decision. Deciding to do something, and then wanting it so badly that not achieving it then becomes the impossible notion in your mind.

I’m going to be very honest with you and tell you that while I’ve learned a lot, I’m still figuring this all out. I’m here tonight to offer a snapshot of where you may be in a year from now. That may inspire you; maybe it will scare you away from your travel dreams. Either way, tonight I hope to offer up a very real and honest example of someone not so unlike yourself, and to provide some tangible inspiration and a relatable story to help you find the confidence needed to make that first bold decision to break through that paper-thin barrier.

I believe the first step, that deliberate decision to do something, is the hardest. It’s also the most important step, because after that first step, several things happen to your advantage to help you along your journey:

You’ll be reminded of the resilience of the human spirit.

“One of the greatest discoveries a man makes, one of his greatest surprises, is to find he can do what he was afraid he couldn’t.” –Henry Ford.

You’ll reinvigorate and refuel your self-confidence.

“A determined soul will do more with a rusty monkey wrench than a loafer will accomplish with all the tools in a machine shop.” —Robert Hughes

You’ll attract like-minded people who will help pull you up.

“A great mission will attract like-minded individuals that want to go on the same journey.” –Aaron Levie

Someone who is marching confidently toward the direction of their dreams attracts other people who are on a similar journey.

Your next steps will become clearer.

“To get through the hardest journey we need take only one step at a time, but we must keep on stepping.” –Chinese Proverb

Imagine you’re driving at night with only your car headlights to guide you. You can see only several meters in front of you, but those several meters are all you need. While you can’t see the entire road, you believe you’ll eventually get there because you can see the next immediate steps front of you.

10 pieces of advice to help make that first bold step

Since I believe that first step is toughest, I’d like to offer up little nuggets of advice that continue to help me:

1. Think of your life in terms of potential regrets.

Project yourself into the future. What will you most regret in 10 years? 20 years? 50 years? I believe that the negative feeling of regret tends to compound over time, so it’s best to address it early. I’m less concerned about what will happen over the next year or two if you act on your dreams; I’m more concerned about what happens in the next 10-20-50 years if you don’t act today.

In 2012, The Guardian ran an article describing a nurse who documented the top regrets of her dying patients. The #1 regret of the dying? I wish I’d had the courage to live a life true to myself, not the life others expected of me. 

“This was the most common regret of all. When people realise that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realise, until they no longer have it.”

2. Write it down.

“The first step to becoming is to will it.” –Mother Theresa

What do you want most? Write it down like it’s a To-Do instead of a To-Dream. Put it on your list between “buy milk” and “go to the gym.”

Then put yourself there in that moment of you living your dream. Write down what you’re experiencing. Describe it as if you’re in the midst of your journey. What are you seeing, feeling, smelling, eating, drinking?

Keep this handy and reread it every time you find yourself slipping or forget your end goal.

3. Find your heroes.

I find most of mine through books and blogs. Surround yourself with these people, or if they’re unattainable or no longer alive, surround yourself with their words. Don’t try to imitate them necessarily, but emulate the way in which they’ve achieved their goals.

Regarding my goal of a lifestyle of travel, I read these blogs:

4. Surround yourself with like-minded peers (and like-minded ideas).

If you’re constantly surrounded by people who have no ambitions to leave “the city,” or worse, who want to leave but have given up, then you’ll forever feel crazy in your travel ambitions. You’ll never have the support network needed to make a big move.

Join Communities:

  • Escape the City
  • Meet Plan Go (global meet-ups for people interested in career breaks)
  • Form your own! (I started a business book club with friends in Chicago)

Read Books:

Watch TED Talks:

Attend more events like this. Find people who have similar ambitions as you, or who have done something you’d like to do, and become friends with them.

5. Share your dreams.

Only until you share your story and your dreams do people have the opportunity to help you. And I found that once you’re clear about what you want, and learn how to articulate your story, your world completely changes. People enter your life to help you achieve your dreams.

I’ve found that in general people want to help each other. But people who have a burning desire and big dreams, those are the people we want to help the most. Be one of those people.

My relationship with Escape the City began with me sharing my story with Adele. Now one year later, I’m an Escape the City speaker.

6. Dare to be vulnerable. 

Dreams are very personal things. I’m not naturally the most open person. My tendency is to keep things close to the hip to minimize opportunity for criticism. But since I started traveling and writing publicly, I’ve witnessed the power in opening up and letting people closer inside my heart and head by sharing the crazy/stupid stuff that excites me.

Watch Brené Brown’s TED talk, On Vulnerability:

7. Listen to your excitement. 

I have a hard time with the whole follow your passion thing. It’s too fluffy. I prefer listen to your excitement.

What specific thing gets you excited? What project or idea stirs your blood? Proceed confidently in that direction.

Why is it important to go after your excitement right now? Because the project/journey/business/thing that excites you right now, that’s an indicator of the path you should take. That path will lead you closer to where you need to be.

Slow-traveling excited me. Then, learning about publishing and book marketing excited me. Now, developing a brand of alternative, travel, anti-guidebooks excites me. I’m not sure where this will lead, but I believe that as long as I’m listening to what excites me, I’m heading in the right direction.

8. Embrace an experimental mindset.

I’m a perfectionist by nature, so I often over-calculate my every move. If I had waited for everything to be perfect before leaving on my sabbatical from IBM, I would have never left. I didn’t necessarily know what would come of my trip. I didn’t know if I would actually return to IBM. I certainly had no idea I’d turn GiveLiveExplore into a publishing company.

The single most important thing that’s kept my paralysis from analysis at bay is viewing every leg of my journey as an experiment.

This doesn’t mean you don’t care about the outcome — you still have to want to succeed. But you have to be willing to stand up and say “I’m trying this thing, and it may not work out.”

This doesn’t mean you do it half-assed. It just means that you honestly admit from the onset that you may make mistakes, you may trip and you may fall. But that’s OK. Because you’ll be learning along the way, so long as you continue to pick yourself up.

9. Be thankful for your discontent. Celebrate it.

Let us not forget that having a well-paying job that lacks meaning is a very privileged problem to have. We’re knocking at the door of the highest point in Maslow’s hierarchy of needs: Self-Realization. But instead of feeling ashamed or guilty, or worse, ignoring this desire to find meaning in our work, let’s be thankful this discontent exists. Shouldn’t it be celebrated? Finally, we’re admitting that we’re a little lost! It’s far better to wrestle with these tough questions than to ignore that they exist.

And now that we’re comfortable with this uncomfortable feeling of discontent, let’s do something about it.

10. Love yourself.

There’s a difference between being completely selfish, and loving the hell out of yourself. Love yourself enough to listen to your own dreams. Sometimes we’re more willing to help someone else achieve their dreams than we are our own. I believe we can help each other while still ensuring we’re moving closer to our dreams.

Love yourself unconditionally and don’t ignore the burning desires inside you.

In conclusion…

The main message I hope to convey is this: I’m out here, trying this. This is basically an experiment. Could I be doing things smarter? Yes. Am I always taking the best approach? Unlikely. But I’m here in front of you tonight to give you a tangible example of someone, not so unlike yourself, who is doing something unconventional. I’m also here also to tell you that I don’t have all the answers. But that’s OK. I’ve realized I don’t need to have all the answers to proceed.

In fact, you’ll never find all the answers sitting here, because the answers don’t live here. They live outside of this room. They’re sitting, waiting, lurking, and speckled around the hidden crevices of the world, hoping to be discovered. We just need to go out into the world and care enough to find them.

I hope that my story helps remind you of the resilience of the human spirit and gives you the simple confidence needed to proceed toward the life you imagine for yourself; to break through the mental barrier, make the decision to move forward, and proceed knowing full well that things will work out in the end, as long as you just keep on stepping.

Several people have asked if this talk was recorded. Unfortunately the only recorded evidence from the event in London is this 15 second Instagram video:

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