How Do The "Little Decisions" Lead to Big Changes?

There’s a story I’m known to tell, and it goes something like this:

In January 2012, I was working for IBM as a senior consultant in Chicago, making decent money and living comfortably, but doing work that felt mostly meaningless. There seemed to be a huge disconnect between the work I was doing and the work I wanted to be doing in my life. And while I wasn’t quite sure what exactly what that ideal work was, I knew what it should feel like… and what it didn’t feel like.

It may have looked one way…but it felt more like another way:

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I was stuck: where do I go from here?

Instead of pondering the fluffy what’s my passion? question over and again, I asked myself a more tangible question that cut through to my core and revealed hidden, unrealized dreams: What excites me? What would I do if I didn’t have to go into work tomorrow, the next week, the next month, or the next many months into the foreseeable future? If I could do anything in the world, what would I do?

I always wanted to travel long-term and explore the world at my own pace, to experience life in the most stripped-down and honest sense of the word.

Eventually, I made a rash decision: On a cold January day in Chicago, I decided to book a one-way ticket to Iceland departing six months later, on June 2, 2012.


Image: Iceland Naturally

I wasn’t sure what I would do about my job, my apartment in Chicago, my things, or my responsibilities. But I had the simple confidence that things would work out. Less important than the physical act of purchasing that plane ticket was the statement I made to myself and the universe with that decision. Instead of continuing to be a passive participant in my own life, I decided to deliberately take control. And in that moment, the world looked different to me.

I was graciously granted a 7-month sabbatical from my job. A part from regrettably missing one wedding, all other “important” responsibilities and commitments seemed to dissolve indifferently as I slow-traveled around Northern and Eastern Europe for the rest of 2012, meeting interesting people, reading, writing, living fully and openly, and generally just appreciating being alive.

I’d like to press pause on my story for a moment.


Let me be honest and say: this is a very sexy story to tell.

On the surface, I made a big decision — the oneway ticket to Iceland — and then went on a romantic and euphoric jaunt. For the most part, this is true. And I’ll also be honest and say that my decision to book that oneway ticket to Iceland has led to my proudest achievements over the past few years.

But in honor of keeping the story sexy, there’s a temptation to make it sound like that before booking that oneway ticket, I had made no bold and deliberate decisions. My life was boring and gray and I was sleepwalking through it. But that’s not entirely the truth.

Since my point isn’t to try and impress you with my story, I’d like to open the kimono and give you a peak at the reality of my story. And the reality is that my story looks more like an Iceberg.

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Let me explain. The tip of the Iceberg was my oneway ticket, the BIG DECISION. But, like an iceberg, if you go deeper beneath the surface, you’ll see that it’s actually stacked upon a foundation that’s much grander.

I’ll call these the little decisions.

The little decisions.

Yes, the oneway ticket was a crucial and important step. But the little decisions, the little experiments I made before that — those things at the base of the iceberg — were no less important. And without them, the oneway ticket wouldn’t have happened; without the base, the tip of the iceberg wouldn’t have been able to exist.

So what were those little decisions? There were many, but I’ll highlight 6:

  1. Creating the Chicago Business Book Club with a group of friends in Chicago as a forum to talk about books, business, but also the broader questions of what we wanted to get out of work and life.
  2. Surrounding myself with like-minded peers and like-minded ideas by attending “career break” & travel meetups; watching TED Talks; subscribing to websites and blogs like Escape the City, Chris Guillebeau’s The Art of Non-Conformity and Tim Ferriss’s Four Hour Workweek Blog.
  3. Forcing myself to craft and then succinctly define a set of values to become my life compass: Give, Live, Explore.
  4. Setting up a company around those values and teasing out some business ideas, including trying to become the North American distributor for a Peruvian luxury clothing brand on the side; trying to build an innovative mobile app with friends; trying to start an investment group to learn about personal finance and stock market investing. (notice the word trying.)
  5. Petitioning for myself to move practices within IBM from an area I didn’t enjoy to a new practice that I thought I might enjoy more.
  6. Going on mini-adventures with friends, family, or alone.

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These are the things I rarely talk about when I talk about my story. And the reason isn’t because I’m trying to hide them — it’s just that people’s attention is short and in trying to write my future story, I needed to focus more on the BIG DECISION — the jumping off point from which all future projects and endeavours were born.

Yet during that trip, instead of ending all little decisions and little experiments, I gave myself the permission to double down on the little experiments and focus my time entirely on them. I used my newfound time to make more decisions — more little experiments.

There were several, but again, I’ll highlight 6. I allowed myself to try things like:

  1. Writing about my travels, experiences, and the life philosophy I was developing.
  2. Designing and building a blog upon which I’d share my writing.
  3. Experimenting with photography.
  4. Experimenting with videography.
  5. Reading many books on my ‘to-read list’.
  6. Traveling slowly and diving deep into the cultures of each place I went.

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Because of that trip: the little decisions -> followed by a BIG DECISION -> followed by more little decisions, a series of things happened that I could never have predicted.

Leveraging the Little Decisions.

Because I let myself experiment with writing and spending time building my blog GiveLiveExplore, I had developed a platform upon which to share my story with anyone who cared. Because I started reading books that interested me and started writing about them, and because I felt a tremendous amount of gratitude on that trip (an example of me living out my value of Give), I gave myself permission to reach out and thank anyone who had inspired me in a certain way.

One of those people were Paulo Coelho, the famed author of the international bestseller The Alchemist. I decided to write a blog post about one of his new books and what it meant to me on my deliberate wandering. I then decided to share that blog post with Paulo Coelho on Twitter.

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I had given something to Paulo (a blog post, a piece of writing, a thank you) and apparently he appreciated it – so much so he shared it with his 5.8 million followers (update from the future: almost 10 million people follow him now):

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Which promptly crashed my website after 5 minutes. So much for my 15 minutes of fame!

Fame or not, I considered that to be a gentle (or aggressive, depending how you look at it) nudge from the universe: “Stick with this writing thing and see where it leads.”

So I did. And I continued to travel. I continued to write. I continued to try to build a following. It turns out my message was resonating with people who were also in my position. Eventually, I came home. When I did, I didn’t let the little experimenting stop. I kept kicking off more little experiments leveraged upon the experiments which seemed to be fruitful. Over the course of 2013, I tried a handful of more experiments. I made some more little decisions.

Again, here are 6:

  1. Applied to speak at blogging conferences, travel conferences, and other meet-ups.
  2. I tried my hand at self-publishing. Not of my own writing, but of my friend’s writing.
  3. I also kept writing, but this time petitioning to write on other people’s platforms — like Escape the City’s.
  4. I reached out to authors with forthcoming books and volunteered to write blog posts in exchange for free advance copies of their books.
  5. I picked up some freelance work building websites and publishing books.
  6. I tried to keep a location independent lifestyle, traveling throughout all of these things.

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Let me pause again to point something out.

What happened to the photography? The videography? The other little experiments?

Those experiments, while fun and intrinsically fruitful, didn’t seem to pan out to much. Take a look at this comment from only 3 weeks ago on a video I made in Croatia (which I only noticed when researching this post):

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The writing and the blog though — that had potential. So I kept leveraging the experiments that worked and kept going down those paths to see how far I could get. In doing so, a bunch of other things happened.

Again, here are 6:

  1. I was invited to speak at a TEDx conference at a university in Pennsylvania.
  2. The book I had published written by my friend, Tales of Iceland, became a #1 category bestseller on
  3. Some of my heroes and others I admired started to share my writing, including Tim Ferriss, Gary Vaynerchuk, the guys at Escape the City.
  4. The Huffington Post invited me to write for them.
  5. With my location independence, I spent months at a time traveling and living in places like San Francisco, Ecuador and Serbia.
  6. Through more of these long and winding series of events, Escape the City decided to sponsor me to live and work in the UK to help them launch The Escape School — where I’m now working to help unfulfilled professionals leave jobs they hate and pursue work they’ll love.

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Which brings us up to present day. I’m here because of these little bets, these little experiments, these little decisions I consistently and relentlessly made throughout the past few years.

A Great Chasm.

Let’s go back to the BIG DECISION for a moment — the oneway ticket to Iceland. What made me jump above water, from the base of the iceberg to the tip?

Unfortunately it’s a story of tragedy. Without going too deep into it — a friend of mine was killed in a car accident. As can be expected with any sudden death of a close one, it caused me to reflect upon the shortness of life and pressed me to consider the things that really mattered. In that moment, I realized what mattered the most — that I gave myself the permission to pursue the unrealized dreams I’d been quieting for so long. In this case, my long-time dream of long-term, slow-travel.

I’m not here to tell you to do something as rash as book a oneway ticket somewhere (although I do recommend carving out time to do something similar at some point in your life). But I am here to paint a picture of the importance of decision — both BIG and small. Of having burning desires to do something with your time, deliberately and by your choosing, and then actually letting yourself go and do those things.

I believe it’s important to make the little decisions now for two reasons;

1.  With every little decision, every little bet, every little experiment: you’re learning. Learning about yourself, about the things you like, about the things that matter to you, about your strengths, interests, gifts and passions.

2. In the event that the universe reaches out to you and asks you to take a big leap — make a BIG DECISION — you’ll be ready. You’ll be ready and willing to say “Yes” to your adventure because you’ve become more confident in yourself, your abilities, who you are and what you stand for. You’ll be ready because of the little deliberate actions you’ve been making along the way.

I guess the eternal question for me is this: Can you make a big change, take that first really bold BIG DECISION without a tragedy, without a rock bottom, without a certain suffering? I can’t say for sure. But I wouldn’t be writing to you today if I didn’t believe it was possible. I think it’s harder to make a really big move without tragedy. I believe that if you’re surrounded by a group of supportive people — a Tribe — it’s more than possible.

Whether tragedy gives you an opportunity to make a BIG DECISION, or the group of allies you’re forming this weekend helps you make a leap, I’d like to share some advice given to a young Native American at his initiation:

“As you go the way of life, you will see a great chasm. Jump. It is not as wide as you think.”

Leap of Faith

Great Leap by Jane Evershed

So, What’s Changed Inside?

I’m often asked, indirectly if not blatantly, “what’s changed on the inside since the BIG DECISION?” Because someone else has articulated it better than I ever could, I’d like to steal their words of wisdom.

From W.H. Murray’s The Scottish Himalayan Expedition:

“Until one is committed, there is hesitancy, the chance to draw back. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favour all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamed would have come his way. Whatever you can do, or dream you can do, begin it. Boldness has genius, power, and magic in it. Begin it now.”

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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