My journey started in 1998–1999 after my Microsoft Canada work term, where I served as Anti-Piracy Marketing Associate, managing their anti-piracy website and publishing licensing and guidebooks for all of Canada. Microsoft flew me across the country speaking at technology shows from Halifax to Calgary, Edmonton, and Vancouver. That year, Bill Gates came and talked to us; 1999 was also the year of a domain run — e.g., z.com sold for $6.8 million.

After that work-term, I wrote my first strategic plan — my target resume: Prime Minister, honorary doctorates, Nobel Peace Prize (future decades), and ownership of the Phree brand of domains, incorporated as Phree Shares Inc. to protect the idea.

Fast forward 23 years to the pandemic — I was let go from my tech job, so I hired myself. I created the world’s first 25-year legacy life strategy digital book-course, called You're Gifted So Think Phreely, featuring over 30 poems with reflective questions from 1996 (when I won 7 scholarships) to 2021 — all designed to teach how to think phreely, without limits.

In 2022, I completed a $220,000 renovation of an investment property purchased in 2016, sold it for $1M, and funded our first $25,000 Dream Decade Challenge Think Like A Principled Billionaire PhreedomAcademy.com Scholarship (1/4 of the $100,000 DreamDecadeChallenge.com retreat investment). That same year, I retired in Antigua at 45 (#Phreedom45), marking the beginning of a new chapter of Phreedom and legacy-building.

The scholarship was awarded to Vignesh Chavan, a gifted IT college student, who helped us design ThinkPhreely.net and our PensPowerClub.com office in Mumbai. Through this $25,000 scholarship and coaching program, Vignesh bought his first car and learned how to invest in real estate in Canada — already with a reference from a retired ex-Microsoft tech founder (#Phreedom45).

“Most people overestimate what they can do in one year and underestimate what they can do in ten.” — Bill Gates

“And we grossly underestimate what we can do in a lifetime.” — Jason Humphreys Kinte, Microsoft Canada (1998–1999, 2002–2004), founder of Toronto Poets (2002–2010), the Increase the Peace campaign (2002–life), the Dream Decade Challenge (2010–life), PensPowerClub.com (2011–Present), ThinkPhreely.net (2021–Present), Principal at PhreedomAcademy.com (2022–Present), and President of Dream Livers Club Inc. (2018–Present).

Barack Obama once said that most “men are either trying to live up to their father’s expectations or make up for their father’s mistakes.” My father, Bernard Humphreys, was a genius scholarship winner from Antigua who also completed his Bachelor of Commerce in Toronto, working in EdTech like me—he was an auditor at DeVry Institute of Technology. When he was in Antigua, he was such an academic star that people used to say they’d read about him in the newspapers, that he’d be prime minister of Canada one day. But he was not entrepreneurial. When he was laid off in his 40s, he intended to drive a taxi in between jobs, but he never landed another auditing job. He fell behind on computer skills and never hired himself. That led to 25 years of underemployment, depression, and eventually divorce. He tried to end his life twice and passed away on November 27, 2014, with me at his hospital bedside, due to pneumonia after signing a do-not-resuscitate order. Watching his decline burned into me the cost of not staying current with technology and not being able to hire yourself.

In 2002, while working at Microsoft Canada and campaigning for the 21st Prime Minister of Canada, Paul Martin, I started Toronto Poets and the Increase the Peace campaign. We hosted over 100 events of talent, talk, and teaching until 2010, registering Toronto Poets as a non-profit corporation in 2007. Three years later, on January 1, 2010, I wrote my Dream for the Decade: get our show, Saturday Night Love, on TV. Dreams require action—so we moved from partner restaurants to the George Ignatieff Theatre at the University of Toronto for bigger monthly shows.

By April—our 4th monthly show—an Asian program on Toronto’s multicultural station televised it for phree! A 120-month dream arrived in four. I realised I’d been dreaming too small, so I aimed to travel the world. With no funding or time, I sold my house—at 33 having to move back in with my mom. I paid off over $25,000 of Toronto Poets’ show debts, closed Toronto Poets, and in 2011 launched PensPowerClub.com as a for-prophet (for-profit company founded by a prophetic scholar, lol) sole proprietorship. I devoured books like Think and Grow Rich and Rich Dad Poor Dad (now two of 100 books on our “Who’s the Best” PensPowerClub book list).

In 2016, I bought the Phreehouse in my hometown of Pickering, Ontario, for $512,000, rented upstairs, and lived in the basement while working at Fleet Complete in Customer Success (2012–2018). I was paid to hire staff and train them in Jamaica as Senior Customer Success Specialist, among other initiatives, before I retired from there in 2018 after giving almost a month’s notice. During the pandemic, I hired myself and built the world’s first Phreedom 45 25-year legacy book-course, You’re Gifted So Think Phreely—The Course at ThinkPhreely.net, and the $25,000 program Think Like a Principled Billionaire at PhreedomAcademy.com—to earn the phreedom to travel, starting in Antigua in 2022. During those three years, one ministry I served online had over 15,000 Christian singles who publicly committed to waiting until marriage to make babies—Worth the Wait on Facebook. It’s hard to be in your twenties and launch a million-dollar company, pick the right co-founders, and pick the right spouse for life all by yourself. It’s highly unlikely to have the wisdom to do so in your twenties. So I waited and am still looking and preparing.

Learning from your parents’ mistakes and other high achievers’ mistakes is better than just learning from your own. I took to heart Bill Gates’ advice on what he’d do if he had to start over: he said he’d finish school and learn from CEOs rather than dropping out early, and he wouldn’t hire full-time workers. (When he was 48—like I am now the second time I worked at Microsoft—Microsoft had 50,000 full-time employees.) Instead, he said he’d build systems like a multi-level marketing model so motivated people would keep working under you instead of relying only on full-time employees. These principles shaped how I’ve scaled ventures and trained others, and been patient to achieve holistic success that lasts—like the only perfect CEO talks about in the only perfect business plan. Jesus says:

“You did not choose me, but I chose you and appointed you so that you might go and bear fruit—fruit that will last—and so that whatever you ask in my name the Father will give you.” (NIV)

I delayed writing a new decade dream in 2020, waiting for “official” decade boundaries when someone told me the decade actually begins on the 1s (e.g., 2021, 2011, 2001). So I started my Dream for this Decade in 2021. But I realised: you can start your Dream Decade any time you commit to planning ten years out—with Bill Gates’ quote in mind. Still, the decade “officially” beginning on the 1s means my 2010 Toronto Poets show on TV dream didn’t just come true in four months—it came “officially” true eight months before that decade even began!

That’s the power of the Dream Decade Challenge! Now I help CEOs prioritise health, phree time to travel with family, and time for legacy and succession planning—then finalise the 10-year operating plan and train teams for future-readiness to win the next decade. The impartial rankings below help ground the work.