Hi everyone! Summer is here and, as the kids say, it’s fire. Literally. It’s hot hot hot! I’d say it’s time to move to northern Michigan, but it’s hot (and smoky) there, too! Maybe to southern Tasmania. ;)

I could do a whole series on how a century or two of ‘no buts’ thinking got us here, but today, something much less cataclysmic called…

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Evolution of the ButHead

This morning, I was looking back over the past year of The Two But Rule. I started writing it …

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The following is fiction…until it isn’t.

Easter

A few years after the pandemic, I woke up on a warm and sunny Easter Sunday. I got my coffee and sat looking out the window watching people drive by on the way to their various Sunday morning activities. And it struck me then that I knew hardly a soul for miles in any direction of my front doo…

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My dear friend, Jim Spohrer, sent me a caption from a book he was reading that he thought made an interesting counterpoint to my book, The Two But Rule.

Oh! That reminds me to nag you…if you haven’t read The Two But Rule yet…nag nag nag! Or…if, having read it, you haven’t reviewed it yet…more nags! ;)

Get Your Copy Now

The book J…

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The great Jonathan Todd Ross, veteran narrator of more audiobooks than you can count, and also -- yeah -- voice of Marik Ishtar in the Yu-Gi-Oh! anime series, narrated “The Two But Rule: Turn Negative Thinking Into Positive Solutions." (Wiley, Recorded Books).

I had a chance to talk with Jonathan after the audiobook released, and here …

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We’ve Lost Our Shared Sense Of Humor

Groups crumble under the anxiety of working on really hard problems when they don’t have a common sense of humor, when they don’t know how to relax and play together.

This was always a tall order for teams, particularly diverse and geographically dispersed ones. But it has grown incredibly challengin…

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What a week, fellow but-heads!

I had a wonderful time taping the first Two But Rule Live event at the Boyd Innovation Center last week, sponsored by the McNair Institute for Entrepreneurism and Free Enterprise in Columbia, South Carolina. And now it’s off to Washington, DC. Busy Busy Busy! Keep track of events at jwolpert.com/events.

So this week is both a short story and a big drop of exclusive content for subscribers.

Special thanks to Professors Dirk Brown and Marc van Essen of The University of South Carolina, Caroline Crowder and Taylor Kane Brown of GrowCo, Breanna Spaulding, Bill Grant and all the wonderful SC innovators that came out to be in our ‘live studio audience.’

Here’s a short clip for folks who don’t yet have a subscription.

(If you are a subscriber, I’ll just ask that you don’t send the full footage to others without permission. For now, this is just for us but-heads.)

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Two But Rule Live — This Week!

This is a big week, fellow but-heads. The first Two But Rule Live show is happening in Columbia, South Carolina. I’m really grateful to the team at the Boyd Innovation Center and the McNair Institute for Entrepreneurialism and Free Enterprise at the University of South Carolina for standing up …

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2BGPT — First Of A Kind?

I’m making the claim until disproven: "The Two But Rule: Turn Negative Thinking Into Positive Solutions" is the first personal development/business/technology book to launch with a companion GPT on OpenAI.

I did a brief search, and so far I have not found another book published …

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Here’s the private link to today’s livestream of the super-fun podcast, “Joseph Jaffe Is Not Famous.”

https://josephjaffe.com/

I’ll join him in conversation about tomorrow’s launch of “The Two But Rule”.

Join the fun today, if you aren’t…you know…working or something…

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Review

If you preordered The Two But Rule, it’s either on its way or has already arrived. Hurray!! I can’t wait to hear what you think about it.

And in fact, that’s the subject of this week’s post:

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Today, Right Now: Teamraderie

Today is the first day you can book me on Teamraderie, the “Masterclass”-meets-online-team-building platform used by companies such as IBM, Google, Pfizer, Accenture, Spotify, Pinterest, Deloitte, Dell, Bayer, Apple, Applied Materials, Twilio, Amazon, Cisco, and…the list goes o…

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Wow! Here we are in 2024, and there are just 16 days left until “The Two But Rule” hits bookstores…including both independent booksellers like Quail Ridge, all the online vendors, AND 300 Barnes and Nobles across North America! Not a bad landmark in a years-long journey to learn all about…yeah, Buts.

By the wa…

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Happy New Year, everyone! I’m really looking forward to 2024, and I hope you are as well. In spite of the uncertainty and trouble in the world today, I’m feeling positive about the future. Why? Here are a few thoughts about that on this last day of 2023.

The Joy of Purpose

I have a good friend who is a true con…

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Hi friends! This is the last issue of 2023 for The Two But Rule…and it’s one with a ton of exciting news! (Hint…look closely at the picture above.)

Early Access to the full Kindle Version of The Two But Rule!!

My editor at Wiley, the publisher of “The Two But Rule: Turn Negative Thinking In…

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Last week, I was thinking about what story to feature in the 50th issue of The Two But Rule — Yes! We made it to 50! — when I got a call from an old friend…and then another call from a different friend…then another.

They were calling to see what I knew about job prospects for senior product executives. These were folks over 50 with decades of experience who suddenly needed to find a new job. These calls have been coming in all year.

I can’t think of a more fitting subject for this issue.

The Winter of Senior Product Managers?

While some fields are bleeding jobs more rapidly than others, the dilemma facing experienced workers seems to be happening across sectors, at least in high-tech. And senior technical product managers, in particular, are having a tough time finding and keeping suitable jobs these days.

A rough survey of literature from 2023 paints a confusing picture. In general, employment in countries like the US remain at historic highs, and while some suggest that the over-50 segment is more likely to lose their job and take longer to find another, others suggest that Gen X leaders are doing just fine filling the roles left by Boomer retirees. There’s also some rosy news coming out of the AI sector. We’ll get to that in a minute.

High Stakes, Fewer Options

Regardless of what the statistics say, the product managers I’ve been talking with are feeling the pinch. They’re worried about losing their job. Or they’re spending months finding a new one. Or they’re taking positions that pay less, offer less advancement, and are less interesting than the roles they filled in their 30s and 40s. None of them seem to be getting calls from the recruiters that used to hover like seagulls at a picnic. And filling out online applications is, by all accounts, a waste of time.

Add to this the fact that many Gen X-ers started families later in life. That means they’re still covering the cost of education and groceries for ravenous teenagers.

This is happening just as many are starting to support aging parents that are living longer, running out of savings, and racking up epic medical bills.

Out To Pasture? Really?

I was talking about this with my buddy, ChatGPT, who had this to add:

“These are individuals on the cusp of what should be their golden years. They're looking ahead to retirement, dreaming of finally slowing down, embracing leisure, and enjoying the fruits of their lifelong labor. Yet, the reality is often starkly different. Instead of planning retirement parties, they're strategizing on how to stay relevant in their careers, grappling with the fear of becoming obsolete in a field that's rapidly evolving.”

Full disclaimer — ChatGPT’s stereotyping is definitely ‘not okay.’ Do better, GPT.

That said, GPT’s facile generalization of the 50+ cohort as a bunch of tired, golf-obsessed has-beens is the clue, literally, to a silver lining. And the juxtaposition is all the more sweet given that the point was delivered by AI. I’m going to argue that our saggy old buts have just received a fresh new BUT.

We’re Just Getting Started

Ok, so let’s get one thing straight. While there is nothing wrong with looking forward to retirement, I know very few 50+ product people who are winding down and preparing for a life of leisure. The folks that I know are more curious and engaged than ever. In a sane world, it’s our age group that would be going back to school to get our PhDs while our children support us with the revenue from their TikTok-influencer endorsements.

We’re also benefitting from significant advances in medical science, nutrition and wellness. Most of us in my circle are in pretty good shape. In fact, I dare say that we’re in better shape than previous generations were in their late 30s.

So we’re feeling good, we’re sharp, we have the experience to know a good plan from a bad one, and on a lucid day, we can even embrace a brand new hair-brained idea without shooting it down prematurely. In fact, on a very good day, we can turn a crazy idea into an even crazier idea — but one with a chance of actually working. (If you need to work on the latter, be sure to reserve your copy of The Two But Rule today. That’s what it’s all about.)

But, for all this, times are changing. Ladder climbing and ladder-hopping (where you secure a hefty raise by doing your old job for a new company) are not the sure fire strategies they used to be. It’s time to consider new ways to leverage our experience to build wealth.

Old Dogs Just Got A New Trick

Something happened in 2023 that changed everything. Yes, of course, it’s AI. (I told you we’d get back to that.) And you might be rolling your eyes right now as you anticipate yet another gushy story about how AI is a panacea for everything from climate change to curing gout. And you know what? That’s exactly what you’re in for. Seriously. Lots of gush and rainbow unicorns ahead. You’ve been warned.

Lightning Strikes While Waiting For A Meeting

Recently, I joined a Zoom meeting, and the other attendee was late. Twenty minutes late. After three or four minutes, I got bored.

Earlier that day I learned that I finally got off the wait list for GitHub’s AI coding assistant, Copilot, and its integration with Microsoft VS Code, a popular software development environment.

Now, I should say that as a technical product exec, I haven’t been paid to write any kind of code in decades, and frankly I was never very good at it. But, for some reason I never lost interest in what you could do with code. And I believe that:

1. Every line of code has an impact on the business, and;

2. Every business decision in software that doesn’t understand the code risks being a bad one.

So, after a few minutes of waiting in the meeting, I started having a conversation with Copilot. But before I get into what happened, here’s the backstory.

But For Money And Time

In 2000, I had a pretty good idea for a new venture I wanted to build. In those days, the cost of building and bringing this new Web service to market was $10-15 million. I didn’t have that kind of money, and I relied on my steady paycheck to pay the bills. So I told the story to some other people who offered to pay me if I left my job to start this thing. They took a big chunk of equity, and we went to raise money from other people, who would have taken another big chunk of equity. And then, just as we were getting close to a termsheet, the ‘dot-bomb’ of 2000 began. No termsheet. No money.

Years later, I had another pretty good idea, and we raised about $1 million to start that. Once again I gave away a ton of equity, and it took us a year to develop the product. In that time, another company that had a lot more money blew right past us.

Then, several years after that, I had another pretty good idea, and at that point I just wrote an article hoping somebody with up-to-date development skills and a lot of free time would build it. Four years passed. Nothing.

This has been the pattern for my whole career. And it turns out that I’m not alone. Nearly every good technical product person I know has at least one worthy idea in their back pocket. The problem is that until now, doing something serious about that idea has been a game for one of three types of people:

1. The young and hungry with little to lose, a friend with a couch to surf, and willingness to dine mainly on ramen while starting a business;

2. Older people who were lucky enough to have had a nice exit in the past, giving them the reputation and personal wealth to trade sweat equity for time and a big stake in the business;

3. Addicts who will re-mortgage the house and raid the kids’ college funds to take another run at entrepreneurship.

I don’t fall into any of these categories, and most of the creative product people I know don’t either.

Refer a friend

Mind…Blown!

Ok, so back to my conversation with Copilot.

As my mind wandered waiting for the Zoom meeting to start, I found myself telling Copilot about the article I wrote. The conversation evolved into one that could have been easily mistaken for me talking with a friend…one with software architecture and development chops.

You might have heard similar stories recently, but here’s the thing: It wasn’t just that Copilot wrote some code I told it to write. No…it had opinions about what components to use, questions about my priorities, and ideas for how to best architect the application for scalability, maintainability, security and performance. Um…wow!

Oh! And at the end I asked it to write in-line comments describing what every line of code was doing and why it was there. Voila — best…documented…code…ever!

Then suddenly my tardy colleague joined the Zoom call, and we were off.

Later That Night

I returned to the code after the kids went to bed, and before midnight Copilot and I deployed the code to the cloud, integrated it with three different services, and debugged a dozen deployment issues.

This is where things got really crazy. I had never tried to create this kind of application, and the APIs and integration issues involved with the platforms we chose were previously unknown to me. Copilot held my hand through every step. More to the point: it told me what steps I needed to be aware of, walked me through each one, and solved every problem that popped up. (Whether a software project is written with AI or humans, there are always unexpected issues when you try to get it to run reliably.)

In one case, we were running into an issue that was preventing information from being written to the database. I pointed out the problem, and this is where I knew that everything about my life as a product person had changed.

It said, “Show me the logs.” So I pasted the error logs from the cloud provider into Copilot and it replied, “Oh, I see that some APIs have changed. We need to handle events differently. Here’s what we can do.” It then refactored the entire codebase. After that, everything worked perfectly.

Along the way, Copilot also deftly handled incompatibilities with different versions of various libraries we were using, helped me locate settings I needed to tweak in the service providers’ control panels, and fixed several issues encountered during compile.

I was just along for the ride, though I’ll tell you that in the process I learned more about modern software frameworks — including what can go wrong and how to approach using them — than I could have picked up from taking a dozen courses.

The Value Of Knowing What You Don’t Know

It’s true that there are “no-code” platforms out there that make it easy to deploy a website or even a simple mobile app without having to get into writing code and setting up development environments. But for truly creative apps and Web services that aim to be the basis of a real business, I think you often need to ‘bake from scratch.’

The key, at least for me, was knowing roughly what questions to ask. I had basic awareness, through years of experience, of what needed to be done, even if I didn’t know how to do it myself. That’s a big advantage. It would have taken me weeks or months to learn or brush-up on database options, front and back-end frameworks, and the endless tools and libraries in a modern developer’s toolkit. But what I had was the knowledge about what I could expect an expert technical team to be able to figure out, if I gave them the requirements. That’s what informed my conversation with Copilot.

The Opportunity for Tech Execs

Here’s what I think. The future isn’t coming…it’s here. If you are a seasoned technical product manager with ideas about how to serve the needs of real people, and you happen to be laid off, you can probably build the software product you’ve been imagining and get it into the hands of real users in a matter of days or weeks. You might even be able to take a few swings at making something that people might pay for before even a meagre severance package runs out.

And if you don’t strike gold, at least the thing you build will demonstrate creativity, problem solving, and initiative that should blow your next prospective employer away.

Phantom Friction

For those of us in our 50s, we’ve been through this kind of shift in basic capability a few times. The personal computer. The Web. Search. Mobile. Streaming.

Each time, we had to learn to throw out our old mental models. Some of us still have to work hard to remember deep-down that we don’t need to go to the library or find an encyclopedia to get the information we need. I still sometimes have to overcome the phantom friction that makes me forget that YouTube has a video on just about anything I need to figure out, and all I need to do is pull my phone out of my pocket to find it.

Right now, that phantom friction is in thinking that loading up VS Code and setting up a development environment is a big scary time-suck. I know. I felt it…then I pushed through.

That phantom friction is, at least in software, the only remaining barrier between you and building something that a few years ago would have required finding a technical co-founder, raising millions, and devoting a lot of time just to learn whether your idea was truly worth pursuing.

What Did I Build, You Ask?

The 20-minute project that Copilot and I built is a Slack plugin that helps teams build up pro-rata equity in shared projects organically over time. No, I had never built or deployed a Slack plugin before and didn’t know the first thing about how to do it…but now I do!

Now, Copilot and I are building an application that I’m hoping to deploy with the launch of The Two But Rule on January 24, 2024.

If you’re a paid subscriber to 2Buts.com, I’m happy to:

1. Do a live session with you and show how I approached these projects;

2. Share the open source code with you;

3. Help you think through your idea.

So reach out on LinkedIn, add a comment here, or go to jwolpert.com and we’ll get some time together. If enough of you are interested, maybe we can do a group session.

Ok, that’s a wrap on the 50th issue. I hope you liked it. Please tell your friends and community about it, and encourage them to join our community of but-heads. With the book launch almost here, things are really going to heat up. Stay tuned!

Happy December 4, 2Buts friends!

I had a terrific time last week at the Carolina Connect AI conference. Many thanks to the organizers and to Dr. Dirk Brown, who took time to interview me about The Two But Rule. (I’ll post the video when they make it available.)

I’m happy to say that when I got back from the conference, I spent the weekend with family. So …

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Hello, hello! Here we are, coming out of a holiday week in the US. I spent it with family, grateful for the friends and colleagues who mean so much to me. I also finished the first dry run of the Two But Rule workshop that I’ve been writing and rehearsing.

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Hello again, fellow But-Heads! It’s Thanksgiving week here in the US, and you know what that means. Yes, millions of parents terrified at the prospect of a week without school…and also turkey.

Turkey Fight

At this time of year, you might imagine enjoying a meal with family and friends, coupled with a rousing argument about politics between Grandpa and your sister’s kid that just graduated from college. Good times.

This year, if you dare, take the opportunity to help the Thanksgiving debate club with a little instruction in the Two But Rule. Seriously…if you can pull it off without bloodshed, see if you can get the family adding 2Buts to their 1Buts and see what happens.

“But what you are saying makes no sense to me, because…”
“BUT it would if…”

or

“Your Boomer logic is sus, bruh, because…”
”But I’d think your point-of-view was fire, if…”

There’s a lot to argue about this year…a lot. The lesson of the Two But Rule is to find the human needs behind what’s being said, honor the needs behind our own objections, and try to square them to meet everyone’s needs.

Unfortunately, you won’t be able to consult your personal copy of “The Two But Rule: Turn Negative Thinking Into Positive Solutions” to help until January 24, when it hits bookstores.

But in the meantime, if you’re a subscriber, below is an excerpt from Chapter 1 — Embracing Your But — that should help with your holiday interventions.

Refer a friend

Updates From Last Week

Praise for The Two But Rule

It was such a pleasure to announce the people that took time out of their very busy schedules to read the early copy of the book and review it. Here are the four that Wiley selected for inclusion on the back cover:

“Your Daily But” Launched (With YouTube Playlist)

Last week, I started writing the ‘Your Daily But’ series on LinkedIn, and I think it went pretty well. Folks seemed to like it, and it’s a good rhythm for me leading up to the book launch on January 24 and the speaking/workshop tour to come.

By the way, if you know of an event or company activity that could use a 2Buts speaker, moderator or coach to help kick things off on the right foot, reach out or book me at jwolpert.com. (I do weddings and bar mitzvahs.) ;)

What made the Daily Buts especially fun for me was generating the associated videos with ai.invideo.io. Here’s the playlist on the new Two But Rule YouTube Channel. Crazy right? Let me know what you think and whether you’d like to see these summarized each week here in the Substack.

Join Us In Raleigh for the First Book Signing

The Two But Rule will be available in both print, Kindle and audio versions online. It will also be available at your local Barnes & Noble.

We’d also like to take this opportunity to support independent bookstores. So we invite you to join us at 7 pm on Thursday, January 25th at Quail Ridge Books in Raleigh. Tickets include a signed copy of The Two But Rule and a seat in the reserved section. I’ll sign and personalize books after the program. Reserve your seat here:

John Wolpert | The Two But Rule (IN STORE) | Quail Ridge Books

And now…Your Exclusive Excerpt

If you’re not a subscriber and can’t see the content below, preorder the book to get a free subscription or use this special link to break out of the normal Substack pricing and get your subscription for whatever you can afford.

[If you are able to see the content below, please do not copy or send to others. This is a special early preview just for subscribers of 2buts.com.]

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1. Telling your favorite But-Heads to join us here at 2buts.com

2. Preordering your copy of The…

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