“You should never wait for the world to catch up to your obsolescence." - Futurist Jim Carroll

Here's a truth to consider: your gut feels the pivot long before your head admits it.

Sometimes we are forced into a career change or pivot. Other times, we need to make the decision on our own.

Either way, it's a gut-wrenching moment.

I know that when I was thinking about leaving the corporate world behind back in 1990, I was pretty miserable. My career track had changed due to a merger; my opportunities vanished; my successful path forward was now in doubt. And yet, I struggled mightily with the idea of moving from career certainty to becoming a self-employed unknown chasing a future that didn't yet exist.

But I went through with it, and it turned out to be the right thing to do.

Here's what I've learned in the decades since: when a pivot is forced on you, you go through something a lot like the stages of grief: shock, denial, anger, and eventually acceptance. When the pivot is your own choice, the same thing happens, just in slow motion. You sit in denial that things have to change. You get angry that they have to. And eventually, hopefully, you accept it.

As I wrote in my book Now What? Reinvention and the Role of Optimism in Finding Your New Future, the faster you get to acceptance, the quicker you can reinvent.

So how do you get to acceptance? You learn to recognize the signals. Some triggers will tell you when it's time:

The expiry of your relevance

The "soul-crushing" signal

The need for reinvention velocity

The "Sunday night" signal

Read about them in the full post.

And one trigger that sits apart from the rest: if you are drowning your career misery in substance abuse, the pivot question has already answered itself. The first move isn't a career change. It's getting help, from yourself or from someone trained to give it. The pivot comes after.

Here's the filter, though: not every bad week is a signal. Burnout, a difficult client, a rough quarter — those are weather, not climate. The triggers above only matter when they become persistent, structural, and patterned. If a vacation fixes it, it wasn't a pivot signal.

You should never find yourself thinking "I should have jumped sooner."

Because when you wonder if it's time to pivot, it probably already is.

---
Futurist Jim Carroll is writing this series, The Art of the Infinite Pivot, because he thinks he has mastered the art of the pivot!

**#Obsolescence** **#Pivot** **#Gut** **#Signals** **#Acceptance** **#Change** **#Reinvention** **#Relevance** **#Triggers** **#Career** **#Freelance** **#Lessons** **#Denial** **#Grief** **#Movement** **#NowWhat** **#Optimism** **#Soul** **#AI** **#Recognition**

Original post: https://jimcarroll.com/2026/05/decoding-tomorrow-the-infinite-pivot-series-28-you-should-never-wait-for-the-world-to-catch-up-to-your-obsolescence/

Intent for the Week -- Steady Work, Steady Rest: https://devonellington.wordpress.com/2026/05/04/intent-for-the-week-steady-work-steady-rest/

#Writing #WritingCommunity #Freelance

“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.

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.

---

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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Of Shakespeare and Strikes: https://devonellington.wordpress.com/2026/05/01/fri-may-1-2026-of-shakespeare-and-strikes/

#Writing #WritingCommunity #Freelance #Theatre

Fri. May 1, 2026: Of Shakespeare and Strikes

Friday, May 1, 2026

Full Moon

Beltane

General Strike

Cloudy/rainy and cool

Happy Friday!

I’m honoring the General Strike today, which means no client work, no shopping, no marketing posts, and as little time spent online as possible. And no trip to the laundromat!

Online meditation group was good, and made Charlotte happy. Our group leader loves writing and poetry. She read Mary Oliver to us (which she often does, Mary is one of her favorite poets). She also encouraged us to read a poem every morning as a meditative practice. I’ve been reading one every morning for April’s poetry month, and often read RATTLE’s daily poem, but I like the idea of doing it more mindfully each day beyond the month. Maybe as part of my morning 30-minute meditation? I’ll play with it. Maybe it would be a better way to wind down the workday?

SELF magazine closed after 47 years, because Condé Nast is greedier and more bootlicking than ever. I was a subscriber back in the 90’s, and then got tired of it around the time I moved from NY because it got repetitive. I still have some of the recipes and information I pulled from old issues in a binder. I stopped being their target audience a long time ago, but there were years when some of their information was useful.

My life has changed enough so I could drop publications I used to subscribe to because I felt I had to for professional reasons. I used to be a magazine junkie (especially when I traveled in the UK), but the voices have been so flattened over the years that most of them aren’t worth it. Plus, a lot of the ones I enjoyed have closed. As a freelancer, monthly subscriptions for things don’t work for me. I am not paid on specific days. It fluctuates. I have enough monthly expenses with rent, utilities, etc. If I really like something, I’ll buy a year when I can afford it, but ONLY if there’s no auto-renew. Which I why I prefer to pay by check. Many publications just don’t fulfill my reading needs anymore, for a huge variety of reasons. And I won’t read anything on Substack because the company is very far out of alignment with my values, so a lot of the journalists that scuttled over there don’t get my time, attention, and certainly not my dollars, even if I respect them.

After breakfast, I grabbed the bags and headed out. It was sprinkling rather than raining, and I made the most of it. Picked up a prescription for my mom at the pharmacy, and did the grocery shopping. I didn’t shop much for the apocalypse, but I did score a gorgeous piece of tuna steak my fishmonger had just cut. Forgot the oranges I need for Tuesday’s crockpot citrus chicken, so I will swing by and pick those up after Saturday’s Farmers’ Market. Dropped off some mail at the post office, stopped by the liquor store, ended at the library to drop off/pick up books. Headed home, navigating around the road construction, which had the bottom of our street blocked off (again, with no advance notification), so I came in the top, went down another one way, and cut through the parking lot backing up to ours.

Home, hauled everything up the stairs, put it away. It started raining harder by then. Did the day’s marketing, and went through some email.

Joined the Freelance Friends chat. We talked food and drink, so it was even more fun than usual.

I had trouble settling into work. I wanted to take a nap. Now, I’m not a napper. If I nap in the afternoon, I usually don’t sleep that night. I didn’t get as much ghostwriting work done as I hoped, but again, I’m happy with the quality of it.

I got some information and questions from the Clark liaison about the event mid-month down at Shakespeare & Co. I asked my guest, got answers, and will make the arrangements with them today. The Clark is so good about stuff like that.

Pizza for dinner (Thursday has become pizza night lately). I wavered about whether or not to go to the show or go back into the work, but realized I really wanted to see the show, so I put on Real People Clothes and some makeup, got in the car, and headed over to Studio 9.

Studio 9 is an impressive venue. Intimate, but high ceilings and built for sound (it was constructed primarily for music). Parking would be an issue further into the season, but it was okay for that night. It’s just a little too far for me to comfortably walk, so driving was a necessity. My friend/colleague was happy to see me. I met the woman who runs the venue, and we got into a lively tech discussion. I sat with one of my friends from A4A, and we talked about projects. She showed me the bookcase her partner recently built in their house – amazing! They both have lots of books, too. Waved to some other people I recognized, who were seated across the room, including the neighbor I met at Monday’s event, and one of the poets from Monday’s event was on my other side.

The show itself, SHAKESPARE DUETS, was amazing. It was created by two actors, Andrew Codispoti and Ariana Karp. I’ve seen Andrew’s work in other Elsewhere Shakespeare productions and really like it. Ariana lives in California, and came out to do the show. They did Shakespearean scenes involving two characters, in this show from JULIUS CASEAR, HAMLET, TWELFTH NIGHT, MACBETH, and ROMEO AND JULIET. The total connection and focus and the way they can switch roles (as they did in HAMLET) with completely fresh interpretations that also built on each other was gorgeous. They know the whole canon inside out, and know how to make it immediate. It’s not the sonorous, presentational technique one sees so often. They embodied the text and brought it alive in beautiful ways. I especially loved the character choices in the TWELFTH NIGHT scene, and got to talk to them about it after. The precision and detail and flow of their work is stunning.

Ariana reminds me of what Susanna Centlivre is like in my imagination, as I write about her.

It was pretty dark by the time I had to drive home, but I managed it, without too much stress. It made me realize what a good choice it was to book a hotel the night after my reading, though.

Came home and took a while to settle, but so happy that I showed up and had that beautiful experience. My friend did such a good job producing the festival. It’s the second one – the first was last year. It’s so much work, I know, but I hope it continues, and I hope he gets the support he needs for it to continue.

Slept well until just before 5, when someone tossed up a furball, and then Tessa and Charlotte started fussing. I told them, “hey, I’m on strike today” and they said, “not with us” and then Willa crashed over a table with pictures and books and other stuff in my office, so that was that and I was up.

The morning routine was fine. Since I’m honoring the strike today, I’m not doing client work. I am, however, switching over curtains and furniture coverings and fabrics to the summer fabrics (even though it’s still in the 30’s at night). I’m going to celebrate Beltane, and tonight, the next show opens at FutureLabs during First Friday, so I’ll nip down to that for a bit.

Tomorrow is the Farmers’ Market, and I have to pick up the things at the grocery store I forgot, and wrap up the contest entries. Sunday is the opening of ROOTED down in Lenox. Busy again, but good busy!

Have a great weekend!

“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/