How Can I Take the First Bold Step Toward a More Fulfilling Life?

I’ve grown to believe there is one clear distinction between someone who is dreaming of “escaping” their unfulfilling job to pursue something more personally meaningful, and someone who has jumped in and is in the midst of doing it. The difference is subtle at first glance, but in reality it’s dire and drastic. It’s mostly a mental one and it’s a tool that’s available to mostly anyone.

The difference is decision.

Decision is the biggest, baddest, boldest step in any journey worth taking. Deliberately deciding to do something different; deciding to make a change; deciding to go on a big adventure — and then wanting it so badly that not achieving it then becomes the impossible notion in one’s 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’ve told pieces of my story here at The Escape School. I’ve told of my thought process in deciding to quit. I described how a life-changing Chicago book club led to me booking a oneway ticket to Iceland. I’ve also written about how I constantly wonder if I’m wandering the right path.

The reason I share my stories (and Adele and Rob share theirs, and our guest Essay writers theirs) is to deliver a unique perspective to anyone reading. We’re all at a certain stage in our journeys — be it ahead or behind yours — but we’re still in the middle of it. We certainly don’t claim to have all of the answers; but we do care enough to get closer to them. We attempt to explore the questions in these Essays. And in doing so, offer up a very real and honest example of someone, not so unlike yourself, who’s also fumbling through this thing called life.

The Escape Evening Talks we host in London aim to do the same. Whether it’s a panel of female entrepreneurs, a sage and irreverent spirits brand launcher, or a fiery, passion-filled leadership coach, we try to bring you tangible inspiration and relatable stories to help you find the confidence needed to make that decision and pursue whatever thing you’re aching to pursue. Or if you’re not sure what you want to pursue, give you the confidence to take the first step to discover it.

I’ve been lucky enough to give a couple talks to Escape members in London. (I’m giving another talk on Wednesday, August 18 and would love to see you there!). In these talks, I tend to focus on what I believe to be the most important step in the journey to pursue a more fulfilling life — the decision part. While the decision is mostly a mental one, it needs to be followed closely behind by something physical, real, tangible. Something that let’s us taste it. It needs to be followed by some sort of action.

Sometimes I call it Saying “Yes” to Your Adventure. Other times I call it Taking The First Bold Step.

Sometimes something nudges us to take this step. Sometimes it’s a slow churn that happens within us. Sometimes we just get tired of our own bullshit.

My decision to book a oneway ticket to Iceland was a combination of all of these things.

I learned two great lessons in booking that flight to Iceland.

The First Lesson: The single greatest motivator to Escaping the City (or an unfulfilling job, or anything really) is to have something you’re burning to escape into.

Until you know what that is, until you can define it, see it, taste it — your escape probably will not happen. I don’t mean you have to know the be-all end-all thing you’ll do for the rest of your days; you don’t have to pinpoint your passion and purpose in life. That’s way too daunting and debilitating. You just have to have something you’re dying to do. Something that excites you to no end. Something you would do if you didn’t have to work and if money were no object.

You need to be running toward something with a fury.

The Second Lesson: That first bold step or leap is the toughest, but by far the most important.

I believe the first step, that deliberate decision to do something fresh, bold, and different, is the hardest. Of course, it’s also the most important step, because after that first step, several things happen to your advantage to help you along your journey (with supporting quotes):

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

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

It essentially took me over two years to finally make that first bold step. And that first real, tangible step was booking a oneway ticket to Iceland. Which led me to building a website and a readership. Which led me to publishing a book about Iceland. Which led me to a TEDx talk. Which eventually led to working with the Escape team to help build The Escape School. Which is leading me closer and closer to building a life that’s more fulfilling and aligned with who I am and the gifts I have to offer the world.

Since that first step, whatever it ends up being for you, is toughest, I’d like to offer up little nuggets of wisdom and useful tools that continue to help me. This formula worked for me, and I hope pieces of it will work for you too. Here are 10 steps to help you take the first bold step toward a more fulfilling life.

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

In 2012, The Guardian ran an article describing a nurse who documented the top regrets of her dying patients. What was 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.

“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.”

Project yourself into the future. What will you most regret in 10 years? 20 years? 50 years? 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.

This is similar to Jeff Bezos’s Regret Minimization Framework. As Bezos was weighing his big decision to quit, he ultimately wished to “minimize the number of regrets” he’d have. He dubbed this thought process his Regret Minimization Framework:

“I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. And I knew that if I failed, I wouldn’t regret that. But I knew the one thing I might regret is not ever having tried. And I knew that that would haunt me everyday. So when I thought about it that way, it was an incredibly easy decision.”

[THINK: Project yourself into the future. What will you be kicking yourself for not doing right now?]

2. 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. Developing an alternative brand of travel, anti-guidebooks still excites me. Now building The Escape School is something that 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. And I’m open to listening to next thing that will excite me.

[THINK: What excites you right now? What are you running toward? Because you need to be running toward something. And this thing needs to burn brighter than the thing you’re running away from.]

3. Write it down.

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.

[DO: Write down a list of 100 things you want to do, for yourself and for the world (Thanks John Morgan for the exercise).]

4. 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 designing a lifestyle around things I care about, I read these blogs:

[DO: Who are your heroes? Go find them and read anything by them or about them you can get your hands on.]

5. 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 ambitions. You’ll never have the support network needed to make a big move.

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

[DO: Sign up for some event that speaks to you: Our Escape EventsMeetup.comCreative Mornings. ANYTHING. Meet and mingle.]

6. 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 the Escape Team. Now two years later, I’m working with the team to build The Escape School.

Similarly: Dare to be vulnerable. Dreams are very personal things. I’m not naturally the most open person and 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 The Power of Vulnerability]

7. Embrace an experimental mindset.

I’m somewhat of 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 my blog 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.

[READ: The Icarus Deception by Seth Godin]

8. Celebrate your discontent.

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-Actualization. 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.

Related: Develop an attitude of gratitude. When you’re struggling throughout life —because if it’s not wondering what to do about your job or your career, it’ll be something else — remembering to be grateful for all you have is like a life pack, an energy booster. You gain a certain swagger in your step that will help push you forward.

[DO: Make list of things you’re grateful for. Keep the list in your pocket and look at it anytime you’re feeling down.]

9. 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-like-your-life

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

[READ: Love Yourself Like Your Life Depends on It by Kamal Ravikant]

10. Repeat.

The harsh reality is that life is cyclical. Ups turns into downs turn into ups and downs all over again. Every end is another beginning. Which means keeping steps 1-9 close to the hip is important through every cycle.

The main message I hope to convey through all of this is this:

I’m out here, trying this. We’re out here, trying this. Could we be doing things smarter? Yes. Are we always taking the best approach? Unlikely. But I sit here today to offer up a tangible example of someone, not so unlike yourself, who is doing something. 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 beyond the perimeter of this screen. They live outside of this room. They’re sitting, waiting, lurking, 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. We find them by first deciding to step. And then stepping.


Doing something different with your life and career is hard… but you don’t have to do it alone. If you need help with your Escape and if you are ready to re-take control over your life, join our Tribe.

“No one can tell you what to do with your life and there is no “one-size-fits-all” escape that will lead you to happiness. What does work, however, is exposure to new ideas, likeminded people and a safe environment for you to figure out what it is you really want.”

– Rob Symington, Escape the City co-founder.

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