A year ago, I went to one of my first conferences I’ve ever attended—aptly titled, “The World Domination Summit. (Try telling your parents and your colleagues about this one. Bemused looks and strange faces ensued.) I went anyways. As a slightly more introverted than extroverted person who struggles a bit with social anxiety and large groups of people, I wasn’t sure about meeting all of these new faces, or being part of a crowd. (There’s a reason I spent the majority of my childhood swimming, gardening, or reading–all solo activities. While I’ve shifted in my twenties and become much more of an outgoing person over time, I still find the solace of writing and blogging to be much more rejuvenating than large crowds of people.) In short, I don’t always like going out in public. I was especially terrified because aside from one or two people, I didn’t know anyone, and I didn’t have a wingman.

At the conference, I met some of the most remarkable people I’ve encountered, from Nate, who was walking across America, to Nick, a fellow swimmer and comrade in adventures in New York, to JD, who has taught me so much: In one weekend, I made more friends and found kindred souls than the years spent in various jobs. The recap of the event took four separate posts (Day 1, Day 2, Day 3, and Photos) – and Chris joked that I should become the “scribe” of future conferences because of my note-taking obsession.

This weekend, I’ll be returning to round 2 of the World Domination Summit (#WDS), as both a participant and a workshop leader. But even more than that, I’m excited because a secret year-long race is now coming to a closing point …

Because a year ago, I met three people who joined me in a secret race, and we made a pact that by this time, this year, we would all take strides towards creating freedom and big changes in our lives.



After the conference, four of us made a secret pact. How could we take the magic of #WDS and propel it forward beyond the weekend? Together, we decided we would spend a year exploring our dreams and document our progress on a secret monthly blog– a space to share our fears, insecurities, and progress. We would use each other as accountability partners. We would share our goals for a year and see who “won” the race by year’s end.

The players were George, Kym, Mark and me. In June 2011, we put together a secret website called “The Race” and kicked off our adventures last June 2011. From the first post, aptly called “The Starting Point” we each illuminated some of our fears and wishes, our plans for the next year.

Central to each of us was an insatiable need for freedom: for a chance to roam the world, escape the singularity of our current jobs, build a financial base, or begin working on projects that were immensely satisfying to each of us.

Threaded through each of our posts was a nod to the need to build a financial base, to pay off previous debts (student loans), to outline what independence looked like for each of us, and to paint a picture of what WINNING would look like at the end. In the kick off post, we wrote to each other: What does independence mean to each of us? How will we know when we’ve finished a year, what we’re doing and have done has worked? What are our dreams and goals? What’s not going right at the moment? What is going right?

Looking back at our 2011 selves, here are some of the excerpts from our blog entries:

  • George: “Things are going really well, but still not quite what I want–although I think I have a good idea of what I want. Also, I’m trying to do too much, but I know that the payoffs in the future from spending time to build my side projects will be invaluable. I also want to do an ironman.”
  • Mark: “I am a drummer. I want more. I want the ability to choose when I study overseas, and do it for many months at a time. I also struggle with debt that I stupidly incurred. I’ve tasted what the world has to offer and I want more — is that wrong?”
  • Kym: “I want to eliminate my debts, and figure out a way to provide value and earn a living while also being able to engage in learning and self-discovery—admittedly, I’m not sure how to do this, and I’ll be slowly figuring this out through experimentation. I want to sustain a life abroad, experiment with different countries, and cut off certain tethers from New York (apartment, bills, etc.), but still be able to return every so often if I choose to. My dreams are to sustain a location independent lifestyle, publish a book, and work on a film or documentary.”
  • Sarah: “I want to be financially free to be able to choose what kind of work I do, and never feel the obligation to have to have a job. I have $100K in student loans and car loans, and it feels unbelievably oppressive. At some point, I want the choice to be able to walk away and do my own thing. I also adore writing. I want to be able to write, and be known for my writing, and publish. I sometimes dream of being a freelance writer. I also want to write several books, and become a professional storyteller. I would like to get involved in public speaking and teaching, too.”

“The most important kind of freedom is to be what you really are. There can’t be any large-scale revolution until there’s a personal revolution, on an individual level. It’s got to happen inside first.” ― Jim Morrison


And then, a year passes. When we stopped to look back this week, it’s incredible to realize how much we each did towards our goals and dreams. I can’t share everything that went on behind the closed doors, but I did get permission to daylight our group and share the experiences because of how important the group became. I am so incredibly impressed with each of these individuals and thankful for their honesty, integrity, spirit, and continued encouragement throughout the last year. Some of the highlights:

  • George has been training for multiple races in his transition to triathlon, getting better and better at swimming, built the pizza oven he’d been telling us about (see the time lapse of the entire thing!), and developed and launched his digital delivery app service which has grown exponentially in the last few months. In short, every single one of his goals he worked on or completed.
  • Mark, who I first met in a noise-making adventure through the streets of Portland, taught me how to drum on trashcans, stomp across intersections, and shake my body and make music with it. Sometime around 2AM in the morning I was ruckus-making with the pounding rhythms of percussion and finding a kindred spirit. Since the start of our journey, Mark left Portland, hit the road without a plan and went to see what the world had to offer. Each post we got from him came from a new place in the world, and is at this moment on a boat in the South Pacific getting paid to drum alongside of the world’s best musicians. In his last post, he wrote to us: “The realization that I can really go anywhere—and get paid to do what I absolutely love, which is drumming—is still blowing my mind.”
  • Kym shared with us her five major dreams for her LIFE. One year later, she wrote to us in amazement: “Guys, I’ve already done three of the dreams, and YEARS before I thought I ever would.” Of all of the things my amazing soul-sister has done, it was a joy to see her write and produce a short film while traveling in India; publish her first book, “The Art Of Embracing Life;” turn her life to focus on writing and learning full-time while living a location-independent lifestyle. She has since spent her year in Spain, India, Canada, New England, and New York after selling almost all of her possessions from her previous lifestyle. In short, she created a journey for herself, took a deep breath, and then embarked on the steps to make it happen.
  • And for me, as many of you have already witnessed on this blog—I started this blog, “it starts with,” to look at how and why we do things and how to make things happen, launched a second website on Landscape Urbanism in September 2011, wrote essays about swimming and about adventure, and surprised myself by seeing my words in print on websites like LifeHacker, Revolution Is, and ProBlogger just a couple months later. Perhaps even more exciting, for me at least, were my final steps towards financial independence. I am also incredibly proud to share that I am now “worth nothing.” Over the last four years, I went from a net worth of -$100K in debts to a net worth of zero: Specifically, I’ve saved the same amount in retirement accounts and personal savings ($75K) as I now have in debts (-$75K), and the tick mark beginning July of this year is back in the black for the first time in four years. The sense of relief and freedom from eliminating debts and knowing that I could do anything is worth fighting for.

“Freedom lies in being bold.”  ― Robert Frost


Looking back at our entries, Kym writes about where we first met:

“The World Domination Summit was not unlike the first day of school for me. I had done my summer reading—who was who, who taught what, who did what?, etc Meeting everyone was a joyful experience, but I admit, witnessing each person’s magnitude was daunting. Like the new kid who just moved into the neighborhood and is walking into the high school cafeteria for the first time!”

Today, a year later, I have a profound sense of gratitude for the network of individuals–at WDS and beyond–who are willing to live a bit differently, experiment with ideas and vulnerability, and encourage each other to make things happen.  It’s not about the destination, but about the journey, and the people you can find to share the experience with you. People you can talk to, trust, be vulnerable around, and who are willing to hold you accountable with love and compassion. I know that this year wouldn’t have been the same without the camaraderie and support of each other.

The lows. There were months—full months, back-to-back months, where we each struggled. We shared the worst of it, how we felt we weren’t making progress, how much we were trying to do and yet couldn’t seem to do, how it felt to feel like we were going in circles. We commented and shared with each other, and during the year I managed to see how much each person was willing to do to make their dreams happen. It’s not about doing it alone, although sometimes it’s a lonely adventure: sometimes you need to build a group to rally around you, to hold you up when you think you’re not getting anywhere, to help you out when you lose sight of your vision, to remind you of how much it’s worth to you.


The struggle that so many of us go through isn’t to become what someone else wants us to become. It’s deciding what we want, and what freedom looks like to each of us individually.

For some, that means the ability to define your own hours; for others, that’s living close to family. It’s not up to anyone else but you, and it can take the shape of $20,000 a year and a small house with no items, or it could mean the biggest banking job and CEO title you can possibly imagine. It’s your call, as long as it’s what you really want.

For me, freedom is not the absence of parameters. But it’s about parameters and structures that create the best possible self and the best possible world. And often freedom is difficult, frustrating, or hard. It’s not a pass to “easy,” or “comfortable.” It’s knowing what you want to fight for, and having the audacity and integrity to put in the time to fight.

For those of you in the  STREAKER challenge through July 4—do a quick check-in. Did it work? Did you do it? What did you do? When and how did the habit break?

What does freedom look like to you? Why is it worth it?

And what will you do to get there?


By our earliest definition, the winner is the one who accomplished the highest number of their five goals, and in the case of a tie-breaker—the person who completed their goals first. We’ve still got a bit of tallying to do, but we’ve all agreed to convene at some point in the next one-year mark, a six-pack of beer in hand, arriving at the destination chosen by the winner.

But the real win is figuring out what kind of life you want. And what you’re willing to do to get there.

Not a bad journey.

With love,