JimCarroll

“Pivots are often made years before they happen.” – 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.

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Every pivot you have ever admired looks like a single moment –  it’s a big decision, a sudden leap, a brave day.

It’s not.

It’s something you’ve been thinking about for a long time. But more important than that, it’s something that you were getting ready for long before you knew you were getting ready.

Why is that? Because every pivot worth making was paid for in advance, in the tiny experiments, side projects, abandoned hobbies, accidental curiosities, and detours that didn’t make sense at the time. Here’s the truth: people who appear to have made a sudden leap had been quietly preparing for it for years. They just didn’t know it.

I have a name for it: experiential capital.

It’s a topic that sits at the center of one of my books, Think Big, Start Small, Scale Fast! It’s also a phrase and concept that draws a LOT of attention in every keynote I do, because it offers up a concrete mindset pathway for moving forward.

What is it? Experiential capital is the deep, practical knowledge you can only acquire by doing something. By running small experiments, by tinkering, by playing with technologies and ideas before they matter. It cannot be bought. It cannot be downloaded. It is earned, slowly, through accumulated small bets.

And here’s why it matters – it’s getting you ready for a new trend, new opportunity, or new disruption, long before it happens. In that way, it accelerates your timing of adoption or aligning to a different future. That’s important because in an exponential world, the gap between when a trend appears and when it dominates your industry has collapsed from decades to months. You no longer have time to start learning about a major shift when it arrives. The only people who can pivot fast enough are the ones who were quietly playing with the new thing for years before anyone called it important. The ones who invested in it through ‘experiential capital.’

That is the entire argument of the “Start Small” part of the Think Big, Start Small, Scale Fast mantra that I share! People love Think Big. They love Scale Fast. They often skip past the middle, where the actual work happens. Start Small is the discipline of running tiny, low-stakes experiments without yet knowing which one will matter.

You don’t run experiments to be right.

You run them to be ready.

As I wrote in the book: “In the absence of clarity, taking initiative today is significantly better than finding a perfect plan tomorrow.” Starting small gets you there.

So here is the practical version: You don’t need to know what your next pivot is going to be. You need to make sure you have the experiential capital to fund it when it arrives.

Pick three things at the edge of your industry, your interest, or your imagination. Start playing with them this month. Not as a strategy. As experiments. A few hours a week. Tolerate the awkwardness. Waste frivolous time. Learn by doing. And as you do this, pay attention to which ones you find yourself coming back to.

Those are the ones that will fund your next leap.

Think Big. Start Small. Scale Fast.

Emphasize the small. It’s the fuel for your future.

“Never accept for a moment that you need permission to act.” – 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.

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Most people wait for permission to do anything. It’s the absolutely wrong thing to do.

And I’ve carried this belief into my keynotes and writing – for more than three decades, I have walked on stages and told audiences not to wait for permission.

Don’t wait for permission to innovate. Don’t wait for permission to launch the side project. Don’t wait for permission to chase the trend. Don’t wait for permission to bypass the committee, the budget cycle, the layers of approval, or the gatekeepers. I have told the same thing to Fortune 500 CEOs, to manufacturing executives, to healthcare leaders, to agricultural producers, to insurance boards, to startup founders.

Most of them have nodded and have then gone home and continued waiting for permission to change their own lives.

That’s the part you need to think about if you are on the cusp of your next pivot or reinvention. Telling yourself not to wait for permission to do it is much harder.

Here’s the quiet truth of every solo career, every freelance pivot, every reinvention I have ever made or watched anyone else make: if you wait for permission from someone else, you will be waiting a long time. Nobody is going to send you an email saying it’s okay, you can change now. No manager is going to walk into your office and announce that the time has arrived to reinvent yourself. No mentor is going to authorize your pivot for you.

The decision you are waiting for is your own, and often, yours alone.

I once wrote a post — part of a litany I published in a Daily Inspiration entry — that contained dozens of “Never accept for a moment that…” lines. Things like: never accept that progress is impossible; never accept that fear should guide your decisions; never accept that giving up is acceptable. Buried in that list was the one I think matters most. Never accept for a moment that you need permission to act.

I meant it then. I mean it more now.

In the introduction to my book Dancing in the Rain, I wrote about leaders waiting for “normal” to return after a downturn, and the gap that opens between their hesitation and the future’s advance. The future happens for them, but they miss out on it. The line that came to my mind as I was writing it was this:

The future does not pause for our comfort. It does not slow down when we feel overwhelmed.

And it certainly does not wait for permission to unfold.

Read that again.

Your pivot follows the same rule. The future you are aiming at is not waiting either. Every moment you delay because you haven’t been given the go-ahead is a moment the future moves further away from where you stand.

A few years ago, my wife and I attended the Celebration of Life for the father of one of our closest friends at our ski club, Cedric Gyles. We had only met him briefly, but the man’s life was remarkable. Ced started his career, like me, as a Chartered Accountant. Then he took a leave of absence from his accounting firm to play professional football for the Calgary Stampeders. He won a Canadian championship. He returned to business, eventually becoming CEO of a major insurance firm. He sailed competitively for 80 years, won multiple international yachting trophies, served as Commodore of his yacht club, and helped lead Canada’s first America’s Cup challenge in over a century. He took up golf. He took up curling.

Oh, and he learned the Red River Jig with Métis dancers in his living room with the carpet rolled back. That detail was in his obituary. He lived 96 years.

What I took away from his Celebration was this: Ced regularly permitted himself to try new things. That phrase has stayed with me. That single discipline, one of “self-permission,” seems to be something that he applied across decades, across categories, across reinventions. It’s what a life of not waiting for permission looks like.

So what can you take from all this? Stop waiting for someone to tell you it’s time. Make the decision. Take the step. Walk into the next thing. Most of the regret I have ever heard from people deep into their careers has been about the pivot they didn’t take because they were waiting for someone, somewhere, to say it was okay.

Nobody is coming to permit you.

Give it to yourself.

Then move.

“Your flaws are your most important assets.” – 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.

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We’re all talking about the importance of authenticity in an era of artificiality.

After all, in 2026, AI can generate almost anything. A photorealistic headshot of a CEO who doesn’t exist. A polished podcast in your voice, on a topic you’ve never thought about, in under five minutes. A speaker highlight reel with fake audiences and fake standing ovations. Perfection has become cheap, instant, and infinite.

Here’s the paradox of this new era: when perfection is everywhere, perfection stops counting. When everyone can be perfect, being perfect doesn’t matter anymore.

What stands out now is the opposite. The stumble, the scar, the story too weird to be invented, the detail too specific to be faked, the mistake too painful to be generated. In a world full of synthetic perfection, your flaws are the only authentication signal that proves you are real. It might become the most important signal for your future success.

And in that context, I must confess: I didn’t know I had been operating on this principle for most of my career! For 36 years, I’ve quietly leaned on my flaws without naming them as assets. It was just how I operated. Now, when everyone is talking about AI, I can see how important my flaws are.

An example? In 1995, I appeared on a VHS tape called The Family Guide to the Internet, presented by IBM. I billed myself as a “Global Internet Consultant” and walked a fictional family through the wonders of newsgroups and proper Internet etiquette. It is, hands down, the most embarrassing thing I have ever done. It still exists on YouTube. And get this – I often tell people about it and send them the link. Most people would have buried it, but don’t try to hide from it. It’s proof that I was actually there, in the room, at the moment the future was being figured out.

While not as interesting, there have been many other stumbles, errors, and foibles along the way. The keynotes where my delivery was off, or the message was muddied. The columns I wrote that missed the mark on some emerging trend. The media interview where I didn’t nail the most important issue. There have been organizations that did not want me back after a keynote because I said something they did not want to hear about their industry’s future – I was too honest. There have been engagements where I was handed a “no-go list” of competitors or topics I was not allowed to mention,  which, as I have written before, often turns out to be an unintentional summary of everything that is wrong with the organization. I keep those stories. I share them. They’re part of the receipt.

Earlier in this series, in Lesson #2, I opened a post with three words about my own career: “I was wrong.” Most people would not begin a 36-lesson reflection on a successful career by admitting they got something fundamental wrong. I led with it because it was true, was important to my overall career success, and because nothing builds trust faster than admitting a mistake before anyone asks you about it.

I’m not alone in figuring this out — though most of us only figured it out in the last few years. The Japanese had a head start. In one recent blog post, I wrote about Kintsugi – the art of repairing broken pottery with lacquer mixed with powdered gold, making the cracks the most valuable part of the object. The breaks are not hidden. They are celebrated. The pot is worth more because it was broken.

Flawfulness? Look at some of my recent posts as the rest of the world starts to catch up to:

• In 2016, Princeton professor Johannes Haushofer published a public CV of Failures listing every grant denied, every degree rejected, every invisible failure. It went viral. People could not stop reading it.
• Stewart Butterfield admitted publicly that his game company Glitch had failed, and pivoted what remained into Slack, a company eventually valued at $27 billion. He did not hide the corpse. He mined it.
• In 2009, Domino’s ran a national ad campaign whose opening line was, literally, “Our pizza sucks.” They used real focus group footage of customers bashing the product. Their stock outperformed Google and Amazon for the next decade.
• Bessemer Venture Partners maintains a public Anti-Portfolio. It’s a list of the great companies they refused to fund, including Apple, Google, and FedEx. They wear their misses on their homepage.

Every one of these stories is the same principle in different clothing: the flaw is the asset, the scar is the proof, the receipt is what makes the product real.

So here is the practical version and what this means for you: Stop trying to look polished. AI does polish better than you ever will. You’ll never be able to compete. And perhaps that means that the next round of competitive advantage in the freelance economy will not be earned by people who outperform AI in terms of perfection. It will be earned by people who do something AI literally cannot do: be unrepeatably, specifically, recognizably themselves, scars and all.

Tell the embarrassing story. Quote the bad review. List the failed venture. Publish the rejected pitch. Show the wreckage. Let the cracks show.

These scars are your watermark. They are the most valuable thing you carry is the one thing the algorithms cannot fake: your specific, weird, painful, unrepeatable history.

These types of things are not a liability anymore – and might be your superpower.

“Yesterday’s expertise can easily become tomorrow’s obstacle.” – 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.

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Here’s something most successful people don’t want to hear: the deeper your expertise, the more it can quietly hold you back.

It’s a paradox, actually. The thing that got you here is the same thing that can make you blind to what’s coming next. The hard-won knowledge, the pattern recognition, the muscle memory of how things work in your industry can become the very things that buttonhole you as someone who is too narrow to take on wide challenges.

This is related to, but distinct from, two earlier ideas in this series. Lesson #2 made the case that expertise is perishable: your knowledge has a shelf life. Lesson #28 was about obsolescence: the external signals that tell you the world is about to move past you. Both are about your expertise running out.

This one is different. It’s about what happens before your expertise expires: when it’s still technically valid, still earning you a living, still making you the smartest person in most rooms. Why is that? Because it might lead you to become blind to the need to pivot faster.

I learned this several times by learning how to learn. I’m a huge fan of the phrase “learning is what most adults will do for a living in the 21st century,” because that literally defines my career.

In the late 1980s, I was a Chartered Accountant (I still am, but now known as a CPA). Auditing, finance, and taxes. A solid, respectable career. Then I started watching what was happening with personal computers and corporate networking, and I knew the future wasn’t in ledgers. So I retired the accountant idea, and taught myself enough about technology to become an IT and email consultant when most people in business hadn’t yet sent their first email!

By 1991, I was going deeper. I’d been doing online research since 1984 (that’s not a typo), and I realized that the skill had become a profession. I built a service offering specialized online research to companies, law firms, and private investigators. At one point, Air Canada was a client, hiring me to do detailed research related to M&A activity. The label for that work eventually emerged: “competitive intelligence professional.” I was doing it before the category had a name. Full circle: in 2003, I headlined the Society of Competitive Intelligence Professionals, the very industry that emerged from what I was doing almost 20 years earlier.

By the mid-1990s, I’d retired that role too, and was going deep into the Internet itself, eventually writing the first of many books about the technology, and becoming a recognized voice on the disruptive impact of early Web trends. That earned me a healthy living as a speaker advising companies and associations on how this would change their world. I became an e-commerce expert at the nascent birth of the technology, writing a book about what it meant – and having VISA feel comfortable enough to place their logo on the cover.

Yet by the early 2000s, I retired that expertise as well. The dot-com collapse made the “Internet expert” label feel dated. So I rebuilt myself as a “Futurist, Trends and Innovation Expert,” which required learning something else entirely: how to do deep, fast, industry-specific trend research. That last skill is the one I’ve leaned on hardest in the years since, but which went back to the skills I first started picking up in 1984. It’s what allows me to walk on stage in front of an audience of manufacturers, healthcare executives, agricultural producers, automotive dealers, or insurance leaders, and tell them something useful and very specific about their future that is very specific to their industry. I’m not an expert on their industry. I’m an expert on how to rapidly become useful to it. I know how to go deep on the trends that matter. The ultimate compliment? One fellow came up to me after a keynote and asked how long I had been a farmer.

I have also gone deep on the technical complexities of networking and infrastructure when keynoting some of the world’s largest tech security conferences. You can’t stand in front of a room full of cybersecurity professionals and wave your hands. You have to know what you’re talking about, at a level that earns the room’s respect. That comes from the fact that I have probably about a dozen computers in my home, as well as many online servers, all of which I tinker with for video production, home automation, and other activities.

Every one of these moments started with me not knowing what I was doing.

So what does all of this mean? Learn to learn. Don’t let your expertise box you in. Go wide. When you’re an expert, your reflex is to defend what you know. When you’re a beginner, your reflex is to ask. You see the gaps. You notice the strange edges. You don’t yet have a worldview to protect, so you can absorb the new one whole.

That puts you in the mindset in which you are continuously learning.

Learning to learn.

Because that’s what we are all doing in the 21st century.

 

“You don’t pivot back to who you were. You pivot to who you’ve become.”– 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.

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Most failed pivots aren’t pivots to the wrong future.

They’re pivots to a future that no longer exists.

I’ve been writing about this idea for years, in one form or another. Back in 2022, I framed it this way: “Confront today as it is, not as you want it to be, but face tomorrow as you want it to be, rather than just accepting it for what it might be!” In another post, I put it more bluntly: “Don’t chase the reality you want. Create the reality you can pursue.” I’ve long recognized that when it comes to reinvent yuorself for the next opportunity, you need to adapt to new realities, not existing ones.

Earlier this year, when Mark Carney stood up at Davos and said, “We actively take on the world as it is, not wait around for a world we wish to be,” he was saying the same thing. I knew immediately why that line landed globally and drew so much attention. He’s repeating this idea everywhere he goes, stating it again pretty clearly at a global summit in Armenia. The dude must be following me. (-;

And yet, it captured something most leaders, most companies, and most individuals quietly refuse to do.

They want to pivot, but only to a future they already imagined.

They want the past to come back, just rearranged.

They want their old career, with a fresh coat of paint.

That’s not a pivot.

That’s nostalgia in a different outfit.

Here’s what I’ve learned the hard way: the future will not negotiate with your desires and wants. It doesn’t care about your plans, your nostalgia, your investment in who you used to be. The future shows up as it is, sometimes brutal, sometimes accelerated, and often inconvenient.

You either align with it, or you don’t.

I learned this most clearly through my own recent recovery. When I fractured my spine in three places, I had a choice. I could spend my recovery fighting reality, mourning the activities I’d lost, comparing every day to the day before the injury, trying to engineer my way back to who I used to be. Or I could accept the body I actually had, the timeline I’d actually been given, and the recovery that was actually possible, and engineer toward the version of me that existed on the other side.

I chose the latter. Daily cardio, even on the bad days. Heavy lifting at the gym once cleared. AI-assisted analysis of my recovery curve.

Slowly, methodically, building the strength required for what came next, not chasing the strength I had before. When I stood on Swilcan Bridge in St. Andrews this past April, I wasn’t the person who had stepped off a chairlift in February. I was someone new.

That’s the principle, the idea, the method.

In a fast-evolving future, keep in mind you can rarely pivot back to who you were. You pivot to who you’ve become.

Here’s the test: when you imagine your pivot, does the destination look a lot like a slightly improved version of your past? If yes, you’re not pivoting. You’re hoping, and hope is not a strategy.

The hardest part of any reinvention isn’t the work. It’s letting go of the version of yourself that no longer fits the world you’re in. The injury you’re recovering from. The career that’s no longer there. The industry that’s been rewritten. The skills that have become obsolete.

You can’t pivot toward a future you refuse to acknowledge. You can’t recover from a body that no longer exists. You can’t reinvent a market that’s already gone.

Take on the future as it is. Work towards the outcome from where you actually are. Build the strength required for what’s next, not the strength you used to have.

Because the only pivot that ever works is the one made from reality.

“Every ‘no’ is a vote for a future ‘yes.'”– 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.

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In the global freelance economy, the pressure is relentless: take everything that comes through the door. Chase every lead. Never leave money on the table. Never turn down an opportunity.

Hustle.

I get it.

I’ve lived that reality since 1990.

Here’s the thing – the tone for the hustle is set right out of the gate. When you’re in year one of running your own thing, every email feels like the difference between making it or not. You say yes to almost anything because the alternative of an empty calendar is terrifying. I’ve lived that reality for a long time. My early years on my own were a frantic hustle of saying yes to anything that looked like it might pay the bills.

But here is what I’ve learned in the 36 years since: the pivots that worked weren’t built on the things I said yes to; sometimes, they were built on the things I said no to.

Every no is a vote for a future yes.

Think about that. Any time you take on the wrong client, the wrong topic, or the wrong project, you don’t just lose that day or that week. You risk losing that time for something that could have been used for something better. You fill your calendar with mediocrity, and then you wonder why the perfect opportunity passed you by. It passed you by because you were too busy doing something else.

From 1998 to 2001, I was doing, perhaps, 80 to 100 events per year. 4 keynotes in 4 days in 4 different cities all across North America. Travel, a full schedule, prep time. It was exhilarating, but at the same time, I was raising a young family with my wife, writing even more books about the Internet, participating in book tours, and so much more. And when the dot.com collapse happened in 2001, I was not quite prepared to reinvent – to pivot – at the speed the future demanded. It wasn’t until 2004 that I finished writing my book, What I Learned from Frogs in Texas: How to Save Your Skin with Forward Thinking Innovation, that I was able to escape the tech lable nd move into the innovation/futurist branding.

I look back sometimes and realize I lost three years that might have made my pivot to a new future easier. I didn’t – because I didn’t make time for the necessary pivot, because I was too busy saying yes.

I learned a very powerful lesson.

It’s hard to think about, but ultimately, saying YES to everything will eventually get in the way of your success.  You can’t move toward a new future if your calendar is jammed with last year’s commitments to this year’s wrong opportunities. The freelance economy doesn’t reward those who say YES most often. It rewards those who say YES most carefully.

It’s not just that – sometimes, you just should not do the things you might otherwise do, and need to say NO – not to make time, but to protect your brand, reputation, and personal outlook.

A few weeks ago, I turned down a tobacco company inquiry. NO. Years back, a client wanted me to take on a topic around cryptocurrency that involved making promises about the technology I knew were unrealistic. NO. (I turned out to be right; the plans the company had involved an area of crypto hype that has flatlined.) Various healthcare events with topics that bordered on fraud? NO.

Then there are the opportunities that border the edge of reality – people putting together a shady conference, a proposal that is clearly on shaky ground, or a business initiative that just doesn’t smell right. After 36 years on my own, I can usually spot a hustler in the first email: within three sentences, sometimes within the subject line. The radar develops only after you’ve been wrong enough times to learn what wrong looks like. And once you’ve got it, you don’t ignore it. You say NO.

Last but not least, saying NO is critical to manage burnout, which puts you in far worse circumstances. Later in my career, when things were crazy hot, I was turning down 5 to 10 keynote requests a week – or rather, my wife was trying to convince me the schedule was simply too full. How did I learn to finally say no? I burned out. I hit the edge. I paid a price. And yet that was a hard lesson to learn, because for a little while, I didn’t listen – I lived for the hustle. The result? For a time, I was a direct casualty of the hustle. (More on that story one day.)

In all of this, I haven’t even mentioned the importance of saying NO to focus on your health, wellness, fitness, and family. The importance of that should be obvious.

Think about all of this this way: in our increasingly complex world, we all need to make time in the hustle to pivot. To prepare for a different future. To reinvent ourselves. To get ready for the next thing. That means you need space to grow, learn, and reskill yourself. This needs a gap in your schedule, a clear hour in your week, an open file in your mind. Every yes you give to the wrong opportunity is a quiet no to the time you should be making in your life.

The Infinite Pivot requires you to be ruthless about what you decline.

That feels uncomfortable, especially when the inquiry comes with money attached. But here’s the test I use: if I say yes to this, what am I quietly saying no to? Because every yes has a hidden cost — the future opportunity you won’t have time for, the rest you won’t take, the deeper work you won’t do, the family time you won’t get back.

Saying no isn’t refusal.

It’s intelligence.

It’s the most underrated discipline in the freelance economy.

Stop chasing every opportunity.

Start protecting your future ones.

The time you guard today is the time you will have tomorrow to pivot when you need to.