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“Never put yourself in a position in which you regret what you didn’t do. - Futurist Jim Carroll

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Futurist Jim Carroll is writing a series, The Art of the Infinite Pivot, based on 36 lessons from his 36 years as a solo entrepreneur, working as a nomadic worker in the global freelance economy. The series is unfolding here, and at pivot.jimcarroll.com.
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Forty-one years ago today, I stepped onto a plane in Halifax, Nova Scotia, heading toward a national office in Toronto, Ontario, and a future that didn't yet have a name.

I was a Chartered Accountant by trade, but my heart was already in the "pipes"—the emerging, messy world of computer connectivity. For three years, I had already immersed myself deep into the opportunities that came from the online world, understanding the power of global collaboration, online research, knowledge acceleration, and disruptive ideas. In my heart and in my mind, I just knew that something big was on the way, and I wanted to be a part of it.

41 years on, I know I did the right thing.

Many times in your life, you will need to confront similar big decisions. Should you make the big, bold leap? Should you take the daring jump into the unknown? Can you really hold your breath, close your eyes, take the plunge into tomorrow, and hope for the best?

If you don't, you might end up regretting not doing the most important thing you should have done.

Never put yourself in that situation.

The greatest risk you will ever take is the risk of staying where you are when you know you were meant for what’s next.

Don't ask what happens if you fail.

Ask what happens if you never try at all.

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Futurist Jim Carroll has been in the online world since 1982. He's seen it go from its nascent beginnings to the massive global machine that it is today.

**#Regret** **#Leap** **#Decision** **#Courage** **#Risk** **#Future** **#Anniversary** **#Journey** **#Pivot** **#Bold** **#Unknown** **#Voice** **#Trust** **#Freelance** **#Lessons** **#Toronto** **#Halifax** **#Accounting** **#Internet** **#Plunge** **#Try** **#Failure** **#Choice** **#Destiny** **#Onwards**

Original post: https://jimcarroll.com/2026/05/decoding-tomorrow-the-infinite-pivot-series-26-never-put-yourself-in-a-position-in-which-you-regret-what-you-didnt-do/

“Never put yourself in a position in which you regret what you didn’t do. - Futurist Jim Carroll

--
Futurist Jim Carroll is writing a series, The Art of the Infinite Pivot, based on 36 lessons from his 36 years as a solo entrepreneur, working as a nomadic worker in the global freelance economy. The series is unfolding here, and at pivot.jimcarroll.com.
--

Forty-one years ago today, I stepped onto a plane in Halifax, Nova Scotia, heading toward a national office in Toronto, Ontario, and a future that didn't yet have a name.

I was a Chartered Accountant by trade, but my heart was already in the "pipes"—the emerging, messy world of computer connectivity. For three years, I had already immersed myself deep into the opportunities that came from the online world, understanding the power of global collaboration, online research, knowledge acceleration, and disruptive ideas. In my heart and in my mind, I just knew that something big was on the way, and I wanted to be a part of it.

The move came about because I had been identified by the national office as someone who could implement the opportunities of that 'something big on a nationwide basis. They offered me a position to chase my ideas, albeit in a bigger, well-funded way - and I accepted.

That moment in time was the final, terrifying step in my ultimate pivot. I wasn't just changing roles; I was abandoning "certainty" for a wild risk on what would eventually become the Internet. And yet, I've never looked back with regret at the decision I made to move forward. I often wonder what my world would be like today if I had let that regret define my future.

41 years on, I know I did the right thing.

Many times in your life, you will need to confront similar big decisions. Should you make the big, bold leap? Should you take the daring jump into the unknown? Can you really hold your breath, close your eyes, take the plunge into tomorrow, and hope for the best?

If you don't, you might end up regretting not doing the most important thing you should have done.

Never put yourself in that situation.

The greatest risk you will ever take is the risk of staying where you are when you know you were meant for what’s next.

Forty-one years later, my accounting title is an artifact, but the decision to chase a future without a name remains the smartest move I ever made.

Don't ask what happens if you fail.

Ask what happens if you never try at all.

---

Futurist Jim Carroll has been in the online world since 1982. He's seen it go from its nascent beginnings to the massive global machine that it is today.

**#Regret** **#Leap** **#Decision** **#Courage** **#Risk** **#Future** **#Anniversary** **#Journey** **#Pivot** **#Bold** **#Unknown** **#Voice** **#Trust** **#Freelance** **#Lessons** **#Toronto** **#Halifax** **#Accounting** **#Internet** **#Plunge** **#Try** **#Failure** **#Choice** **#Destiny** **#Onwards**

Original post: https://jimcarroll.com/2026/05/decoding-tomorrow-the-infinite-pivot-series-26-never-put-yourself-in-a-position-in-which-you-regret-what-you-didnt-do/

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