Stubborn Dreams

Getting out of my cube

An unexpected moment of brave honesty

with 2 comments

World Domination Summit 2013

WDS: The magic is in front of the curtain

I was not a follower of Chris Guillebeau. Last October, I greedily bought tickets for the World Domination Summit in Portland within 12 minutes of getting the email trumpeting the availability of the 1st batch of tickets because I was stuck in a job that I was very good at but not overly in love with. It is too early to tell the true impact and buying those tickets was a life-altering decision.

I am extremely fortunate to be able to do what I do: apply creativity and teamwork to solving technical problems. Sometimes the problem is defining the actual problem. The niche I am in right now happens to be software development. I am extremely fortunate to be able to work with talented and hardworking individuals with passion. But really, I have pregnant pauses where I am honestly bored. Same problems. Same Bat Channel. Fires in a new location. Different Day. As I am beta testing my mid-life crisis, I have to wonder: Do I really want to spend so much of my competitive drive on sitting in a chair in a climate-controlled office writing mobile apps for business?

The day before the World Domination Summit, at the Kennedy School meetup hosted by Sean Ogle, I met many people who I felt that I had more in common with than my co-workers. As someone who is still in the nascent stages of doing something different let alone remarkable, it was fascinating to meet actual people who were two/three years deep into JFDoing their own thing. I did feel like the proverbial clueless, wide-eyed Freshman – where the Seniors were all cool: full-time travelers, two very interesting individuals in the process of building a creative community in the wilds of beautiful Montana, productivity authors with devoted readers (and appliers), location-independent yoga teachers. I didn’t feel like I quite fit in – yet i was there – and not back in the climate-controlled and more importantly, expectation-controlled office.

As the night went on at the Kennedy School, I iterated on my answer for why I was at WDS/what I wanted to set out to do. I initially thought that I could stand out and build my “brand” by taking my OCD writing skills and detail-orientation and write a blog. A blog about what? I’m not really a traveler.

I’ve always been inspired and intimidated by the polish and beauty of the Apple Design Award winning apps. I’ve been thinking about a blog about how to build beautiful, native iOS apps – soup to nuts, napkin sketch to concepts to animations to working code. Building beautiful apps is all about the finish work, the details and the polish. As someone who is already a good plumber (building the stuff no one sees, the ugly but beautiful infrastructure supporting an app), I thought it would be interesting journey of learning, never mind that it would probably be much more difficult than I envisualized – and worth sharing. If I had one take away from the Kennedy School – it is you can build a digital community by sharing your experiences openly. A couple people there even said that I should not be afraid to charge for content – give away a taste but sell the detailed recipe – something I hadn’t really considered. Free has no value…

By the 3rd hour of World Domination Summit, my goal posts irrevocably changed. I was sitting up front in the aisle seat in the 3rd or 4th row from the stage because I had gotten in line at 7:30 (WDS protip: the line expands very quickly after 7:50).

There was a magic moment during ProBlogger Darren Rowse’s keynote in which he instructed us to turn to someone next to us and answer for them: “What is your dream?” and “What is the next action you are going to take towards that dream?”.

It was an unexpected moment of brave honesty. I immediately knew what my dream was. The beautiful woman from Seattle on my left said: “I want to be an actress. And I’m going to go to an audition.” I told her: “I’m going to start teaching problem solving (and maybe programming) to urban youth. And I’m going to follow up with someone I know to start doing that in the Fall”.

Nothing about mobile apps. One thing I did not mention about my job. I work with a lot of young whippersnappers. In the software development industry, youthful energy channeled correctly can trump almost all technical problems and hurdles and (sometimes) deadlines. I am not a young whippersnapper, and I still have that competitive drive – to outwork, to outlearn. Even though I am still competitive (and you have to be in the mobile app domain – where everything changes every six months), I can sense that my heart isn’t really into it. I’m still winning “fights” about how/why to do X in the mobile app code but I am not in the fight.

Writing a blog about building beautiful iOS apps was always an intermediary goal. The biggest success that I could have would be to become an established authority/consultant like Jeremy Olson of Tapity.

I could talk about education for days on end. And the problems in urban education are huge. In my brief forays into the education system here in Philly, meeting educators/teachers in schools and organizations like Teach for America, the problems are fractal. The farther down you go, the more problems will unfold. Yet, it is hard to actually become a teacher especially this late in the game (credentials).

As an obliger (thank you, Gretchen Rubin!), I’ve started putting out my goal of teaching problem solving/programming to urban youth out there, verbally, to friends and friends-at-large. My excited email to my first, strong lead (who I had met a few months prior) to get in front of a classroom of Philly high schoolers has not yet been answered. I will follow-up shortly with a phone call, and Jia Jiang (thank you, Jia!!!) – who was my personal overall heavyweight champion speaker – the way he put himself out there, a superb storyteller, a hero in the making, a superstar but not a “superstar” – will help immunize and inspire me as I trudge through inevitable rejections from teachers and students alike going forward.

As Chris Lehman of Science Leadership Academy (SLA), a premier magnet school, not just in Philly, nationwide said – “If you put a good kid in a bad system, the system wins.. every time”. The key is to not change the system – but start with a small group of students and work your way up. I don’t know what I will be able to do in the Fall – my goal is to be humble and learn more from the kids than I teach them – and WDS has given me, someone beta-testing their mid-life crisis, the courage to be accountable to start taking action on a Big Problem (how to give hope/opportunity to urban youth in this brave new information economy by teaching them how to solve problems).

I left WDS – not just as a follower of Chris Guillebeau but someone in love and awe with the idea of changing the world.

Thank you, World Domination Summit! And to Michael Ellsberg (via his e-mail list) from whom I found out about WDS. Good luck to the woman from Seattle on her first audition!

There are other stories that did not fit into the essence of this particular blog – for now thank you Chris Guillebeau, Jolie Guillebeau, all the ambassadors (especially Kaitlin Fisher, Katie & Tyler Hurst), Tyler Tervooren, the rest of the awesome WDS team (especially Don Matteo), Jean MacDonald, Thursday Bram, Brian, Morgan Day Cecil, the Pink Rose, Jen Lewis, Dave Sparks, Kevin Raulston, and my dream city – Portland.

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Written by kleeruby1

July 21, 2013 at 11:01 am

2 Responses

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  1. Great article Kevin! I’m really happy to read that you’ve broken a new barrier in life. Reading this made me proud of my recent adventures as well. I am more willing to take life changing risk now than I ever have before and it’s because of that decision, I’ve grown more personally AND professionally in the last 1.5 years than I have in the past 10 years.

    “We keep moving forward, opening new doors, and doing new things, because we’re curious and curiosity keeps leading us down new paths.” Walt Disney

  2. It was so wonderful to meet you. Portland and the Cecils are rooting for you, Friend!

    Morgan Day Cecil

    July 22, 2013 at 9:21 pm


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