Feb 14

There comes a time when you take all the skills you’ve acquired over a lifetime, all the connections you’ve made, all the unique vantage points you’ve had the good fortune to have and you go all-in on your Ikigai. For me, that time is now.

I read two books over the holidays: “The One Thing” by Gary Keller and “The Courage to Be Disliked” by Ichiro Kishimi. Both were profound in their own ways and the net result was that they tipped me to make the decision to leave an amazing job that has allowed me to work with incredible people doing interesting work from all over the world. By every stretch I had achieved the grail of employment and I’ve just decided to let it all go.

Pagely has been the best job I’ve ever held. Culture-wise it is bar none the best organization I’ve had the pleasure to be involved with. It has allowed me to live in 38 countries in the last four years and has given me a virtual family, stable income and purpose (they’re hiring BTW). But I realized over the holidays that a) my heart is now elsewhere and b) I am likely no longer what the company truly needs. It was not an easy decision but I’m taking a leap of faith here and committing all my energy to a cause that I believe is the highest and best use of me for generating maximum positive benefit for the world.

Charity Makeover is a project I started as an experiment way back in 2013 to test the idea that we could tap into the unique talents of knowledge workers and assemble temporary teams to help local charities overcome the main challenges that hold them back. Think of it like a virtual Habitat for Humanity, a “digital barn raising for non-profits” if you will (hence the barn logo). We get the right set of smart people in the room and build game-changing digital assets for the local charities of their area which are poised to have incredible impact but lacking the in-house resources to overcome their hurdles on their own.

This effort was back-burnered for a number of years but always lingered as being the one thing I felt I was born to bring to the world.

I was a participant of a conference at sea called Nomad Cruise back in April of last year and on a lark decided to pitch this idea at their “Piraña Tank” mini replica of Shark Tank. You can find my pitch here:

That led to me reviving the effort and organizing an event in Lisbon which then led to a friend I made on that cruise gaining interest in being involved at a core level. On a visit Ben Lakoff made to Lisbon over a series of conversations we decided to partner up and work together to advance the idea. We executed the next event in Barcelona successfully and we felt the momentum.

Fast forward to today on my last day for Pagely… I stand on the precipice of leaving the safety of the company I’ve known for my entire remote existence and am diving head-long into the uncertainty a project with no proven revenue model nor investors but represents the single greatest lever I can think of to move the world.

If you want to follow our journey with this our Instagram will have updates or join my bi-annual personal email update. For now we’re busy preparing for our next event in Bali, Indonesia on March 14th and laying the foundational platform and playbook so that this becomes essentially “wikipedia-like” in the ability for anyone to extend it to his/her town. I’m taking all that I’ve acquired from my 25-year career in the way of knowledge, connections and passion and assembling the crew and tech to turn this into a global movement.

There’s a quote by Tim O’Reilly I put on the T-shirts for the Lisbon event. And it is our mantra:

“Pursue something so important that even if you fail, the world is better off with you having tried.”
-Tim O’Reilly

I’m confident we’ll zigzag our way to a sustainable revenue model with the runway we have. We have a hypothesis now would love an intro to people who work in HR and Corporate Social Responsibility for Enterprises to validate or refine this. In the event of some catastrophic scenario where we fail to make this effort sustainable, it will still have changed many lives for the better in the process and therefore cannot ultimately be a failure.

Thanks to my parents, my friends who have encouraged me to make this leap, Pagely for being supportive and Ben for being the first follower as we morph this into a movement. To the charity founders in the trenches who are fighting the hard fight without reinforcements, air support is on the way. Hang in there.

-Sean

10 Responses to “When it’s time to go all-in”

  1. Susan Tierney says:

    I couldn’t be prouder of you Sean. Everyone I meet who knows you say how brilliant you are. I will always be there beside you as you travel on where ever that may lead you. Love and Happy Valentine’s Day MOM

  2. Isa says:

    Fantastic! Thrilled for you Sean!

  3. Dave Tierney says:

    Sean. A simple parting remarks post, concise and elegant. Dad

  4. Francine says:

    How can I help?

    • sean says:

      Francine, there’s a couple ways you could help us. Maybe easier to jump on a zoom call sometime soon? Can you suggest a few times in your early morning or late evening when you could talk? Or if it’s easier grab something on my cal here? -> Calendly.com/scrollinondubs

  5. Dylan Mouthaan says:

    What a great step. And well described how you came to this decision. Good luck!

  6. Wow Sean! Amazing posts. Amazing life experiences. I have enjoyed following you man. Good luck with Charity Makeover! Love to know how I can help.

    Andrew
    P.S. You coming back to Phoenix?

    • sean says:

      @Andrew – thanks man. No plans to return to Phoenix. Lisbon is home now but my folks and a bunch of friends are still there so I’ll for sure be back for a visit at some point. Connect on Instagram or FB if you’re on either so we can link up while i’m in town. cheers man

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