Rishad Tobaccowala's Blog, page 2

Forever Young.

In Colombo, Sri Lanka, lies a cemetery containing the grave of Arthur Charles Clarke who wrote 2001: A Space Odyssey.

The gravestone has this phrase inscribed on it:

“He never grew up, but he never stopped growing”

Arthur C Clarke remained forever young.

By ensuring a growth mindset our companies and ourselves can also attempt to remain forever young.

Our mobile operating system has upgraded itself 18 times in the past 18 years (Apple) or 16 times (Android)

All around us software is constantly updating itself.

How many times have we upgraded our mental operating system in the past 18 years?

Rethought our internal architecture and our API’s on how we connect and perceive and adapt?

After all keeping our bodies in shape is not the same as ensuring our minds are constantly upgrading themselves.

By upgrading our mental operating systems we can remain forever young long after our bodies stop being so.

The lyrics of Forever Young are by Bob Dylan but the best renditions of this song have tended to be by Joan Baez.

Today some of the very powerful and wealthy might benefit from finding ways to rekindle the younger person in them that their older selves may be suppressing.

To remember when idealism, youthful courage and the vivacity of the new idea enabled the possibilities of anything.

Forever Young by Bob Dylan.

May God bless and keep you always
May your wishes all come true
May you always do for others
And let others do for you
May you build a ladder to the stars
And climb on every rung
May you stay forever young
May you stay forever young

May you grow up to be righteous
May you grow up to be true
May you always know the truth
And see the light surrounding you
May you always be courageous
Stand upright and be strong
May you stay forever young
May you stay forever young

May your hands always be busy
May your feet always be swift
May you have a strong foundation
When the winds of changes shift
May your heart always be joyful
May your song always be sung
And may you stay forever young
May you stay forever young

But in many ways we do not remain forever young.

Our bodies give way, our minds lose a step, raw intelligence is replaced by crystalized intelligence and wisdom.

There comes a time to let go, to move on, to climb a second mountain, to pass the baton to a newer generation.

From the main stage to an encore career or a new life.

A different type of growing.

To find a fit where one’s current state of youth is aligned with reality.

Every career and role has a midnight hour and the smart people leave at five to twelve.

When still seen as a prince or princess and not yet a pumpkin.

There are limits to forever young.

And understanding that one can remain forever young, constantly upgrading and having a growth mindset but understanding that is not the same as youth is what the truly forever young understand.

By not overstaying in a role, a point of view, a belief as the world changes is the we we stay…

Forever Young.

Creativity in an Age of AI.

In an article for The Verge, Nilay Patel its editor in chief, noted that in an interview with Ben Thompson Mark Zuckerberg described a vision where a client comes to Meta and says “I want customers for my product,” and Meta does everything else. It generates photos and videos of those products using AI, writes copy about those products with AI, assembles that into an infinite number of ads with AI, targets those ads to all the people on its platforms with AI, measures which ads perform best and iterates on them with AI, and then has those customers buy the actual products on its platforms using its systems.

At the recently concluded Cannes International Festival of Creativity, the dominant theme according to all reports was AI. And one of the worries apparently was what AI would do to creativity in a tech infused, data driven, highly measured eco-system dominated by Meta, Google, Amazon and others.

So I thought it would make sense to turn to a gentleman who may know a little about the topic.

His name is Sir John Hegarty and for those not familiar with him here is a little bit to establish his credentials to speak to the subject:

Founder BBH: In 1982, with partners John Bartle and Nigel Bogle, he started Bartle Bogle Hegarty one of the most iconic agencies that helped build brands such as Audi, Levi’s and Johnnie Walker among others.

Awards and Recognition: Sir John has received numerous accolades throughout his career, including the D&AD President's Award, the Cannes Lions Advertising Festival Lifetime Achievement Award, and a knighthood for services to advertising in 2007.

Authored Books: He has written two influential books:

Hegarty on Advertising: Turning Intelligence into Magic

Hegarty on Creativity: There Are No Rules

The Garage Soho: In 2014, he co-founded The Garage Soho, an incubator for disruptive business ideas where he invested in dozens of young companies.

The Business of Creativity: Sir John believes creativity is key to business growth and everyone can nurture creativity. A few years ago he co-founded The Business of Creativity working with companies and leaders all over the world.

You can listen to the entire conversation here and the links at the end of the post.

Here are 4 of many many insights and perspectives Sir Hegarty shared including the single best definition of creativity I have ever heard:

1. Sir John loves and has embraced AI.

He believes AI is going to be incredible and profound. It will be a significant democratizing opportunity allowing the unleashing of new forms of creativity.

Sir John suggests we should not view AI as a tool but as collaborator that allows all of us to be creative directors. No longer is there an art director or copy writer but the fusion of the two.

The big challenge of AI are the copyright issues and ownership of IP laws.

2. Creativity is a key to Brands but he is worried that many of today’s brands will fail to endure and are being actively destroyed !

Marketers have become so data driven and so hooked to lower funnel promotion measurable outcomes that significant brand destruction is underway as we have seen with Nike among others.

Brands are not built by promotion but also by persuasion and with the exception of personal brands like influencers very few enduring brands are built online.

Online Brands such as Dollar Shave Club come and go quickly sold to bigger companies who have FOMO. Direct to Consumer brands that depend on metrics and measurement and narrow targeting are mostly eroding because tech companies keep focusing on people who buy the brand or people who look like those who bought the brand which is too narrow and due to competitive bidding for the same people are very expensive to reach.

It is very critical for a brand to be known by those who do not know about it and this is source of growth for most companies. Convincing these folks is not about utility, features and performance but telling a story of what the brand stands for, how it makes one feel, how it resonates with culture, how it fits into a person’s life.

Today brands are being milked and not fed with a focus on the short run.

What is measurable may not be all that matters.

Increasingly smart brands are not only fixating only on online media but are thinking about experience stacks including real world experiences from stores to out of home, immersive media and much more. Out of home grew 8 percent last year !

3. The Definition of Creativity and why there are two types of Creativity.

One day someone told Sir John that the greatest art of all might be music.

Sir John believed it might be the second greatest art for and the greatest of all art is human life.

Human life is an act of creativity.

Sir John defines creativity as follows: Creativity is an expression of self.

Listen to the greatest creative people and you will hear them saying:

“Here is what I wanted to say”

“This is what I wanted to show”

“What I am trying to build”

There are two types of creativity one is pure and the other is applied.

Pure creativity is a spark that leads to the iPhone, creating the Simpsons or designing the Guggenheim in Bilboa. and also drives the greatest iconic works of art, product design and brand building.

Applied creativity is creating the next version of the iPhone, a new episode of The Simpsons or designing the stairs inside the Guggenheim.

Pure creativity is the greatest wealth creator and generator of growth ever.

Creativity drives innovation and the best creativity does not come from A/B testing, mathematics or focus groups.

It feeds on curiosity, instinct, exposure to differing perspectives, feelings and things that do not compute.

This AI versioning is not creativity that builds brands and growth but a smart way to get variations of a theme cost effectively get the lower funnel sale of a Brand that was which was built due to a different form of creativity.

A human creativity of self expression and not a machine variation of optimization and data co-relation.

AI will unleash human creativity but will not replace human creativity.

4. Advice to established leaders and young people

Sir John has suggested that too many leaders fail to lead.

Lots of arrogance and hubris but basically followers, data clutchers, herd like buzz word bingo chanters.

Leadership is about having courage.

The big leaders step ahead, march to different drummers, take risks on intuition, ideas and instinct.

While Sir John did not mention that they should zig vs others zag I could not mentioning this since the symbol of BBH is the black sheep. If you have not seen what this means check out these ads that defined an era and established valuable profitable brands including Audi, Levi’s, Johnnie Walker and many more.

For young people his advice is to find and do something one loves. Do not just follow the data. Play more. Play is stepping forth with the the lack of rules.

A master class on creativity and thriving as a human in an AI age. Take a listen and you will be moved. Here are Apple and Spotify links but all on podcast platforms globally.

More on Creativity.

In the latest The Rethinking Work show an artist and musician turned architect who founded a design firm called FYOOG which is now part of IA one of the world’s largest architectural firm on how to re-imagine space to create meaning, inspire ideas and true interaction. If you want to unleash your team and firms creativity take a look and see spaces that soar and much more. You can watch on YouTube or listen on Spotify or Apple.

And a call for Creative Works!

The art work for this issue comes from Britton Bloch who is an artist, studying for her PhD and is Vice President, Global Talent Acquisition Strategy & Head of Recruiting at Navy Federal Credit Union. Britton also reads this thought letter very much like Karin Onsager-Birch another reader whose work was featured last week and Susan Swinand a few months ago. Do you have art, music, video or photography you would like me to feature in this thought letter? If so please send me a note.

Trust & Integrity

Most long term successful careers, relationships and lives are built not just on hard work, perseverance, discipline, forgiveness and resilience but also trust and integrity.

Trust enables speed and enables people to take risks on those they trust.

Integrity allows one to gain trust and live in internal and external harmony.

They may not result in fame and fortune but often result in contentment, calmness and comfort in one’s own self.

Gaining trust and living with integrity is difficult since human frailty leads to lapses and mishaps. But it is possible to put into practice habits and approaches that engender trust and allow one to live a life of integrity.

And best of all neither requires money or permission, allowing one to thrive anywhere and at all times by living authentically and with candor.

Earning Trust

To earn trust one must be a) clear about intentions, b) show the data, c) be transparent and d) self-correct.

Intentions: If one is not clear about what one is trying to achieve or what our goals are then many people begin to get suspicious. They wonder if there is a hidden agenda or there is some multi-dimensional chess game underway. If we wonder what someone is really trying to achieve it is hard to trust them

Data: In a data driven world how many people are willing to share and show the data on which they are making their decisions or drawing their conclusions? People talk about data but how often do they reveal the facts and figures which how they are coming to conclusions? Show the data versus asking belief in some hidden black box.

Transparency: In addition to clarity of intentions and the access to data it is necessary to be transparent on the process which leads to a recommendation or perspective. One needs to share not just the dish (goal) being prepared and the ingredients (data) but the process (recipe) of combining and turning the ingredients into the dish. This allows people to interrogate and also correct wrong recommendations by identifying where one’s goals, or one’s data or one’s thinking can be enhanced or improved.

Self-Correction: To be human is to err. So often one makes mistakes. A key part of keeping and gaining trust is correcting mistakes, clarifying miscommunications and adjusting one’s behaviors. Often it is how one reacts to something that goes wrong that earns trust than if things did not go wrong.

Achieving Integrity

Integrity is achieved when what one says, one believes and one does are aligned and also consistent with the realities of science and economics.

Clearly there are many times that what we say, what we believe and what we do may not be consistent.

Words, thoughts and actions may not align all the time.

It could be as simple as a white lie where not to hurt another’s feelings we hold our tongue.

Or it could be that we cannot afford to lose our job or endanger a relationship that we end up saying one thing while believing another or doing things not aligned with belief.

But over time a disparity between thought, belief and action leads to an internal corrosion, a draining of agency and is rarely the recipe for long term success.

It makes one insecure, hesitant and reduces the likelihood of success.

We end up living in other people’s minds where external aspirations are disconnected from an internal motivations. By following the wrong star home we our lose the way.

But aligning words, belief and action is not enough to live a life of integrity since life occurs in the real world where the rules of science and economics prevail in the long run.

We can say you we not believe in gravity and we can jump out of the window of a high floor. This aligns words, beliefs and actions but it also leaves us dead.

Or we can truly want to provide help to people, say so and do so but soon we or our companies will grow broke since someone has to create value and build resources before we allocate them away. Supply and demand, incentives of self interest and market economics always end up prevailing.

Words, beliefs and actions aligned with reality of science and economics is the way to achieve integrity.

Art by Karin Onsager-Birch a reader of this thought letter. More about Karin here .

The Rethinking Work Show

Work is central to the human experience and along with health and relationships is a key to happiness.

Work is in the midst of the greatest change in decades and is expected to change more between 2020 and 2029 than it has in the past five decades,

This change is driven by five intertwined forces including 1) demographic shifts of declining and aging populations as well as multiple generations with different mindsets, 2) technological changes including AI, 3) the rise of marketplaces such as Shopify, 4) new types of working where free-lance employment is overtaking full-time employment and 5) the long term implications of Covid on not just where one works but who one works for and why one works.

Four months ago my book Rethinking Work was published in the US and India and is now available in the UK and a few other countries in print and everywhere also as an Audible or Kindle download. The book is filled with blueprints and frameworks and steps every individual, leader and team can utilize anywhere in the world to thrive rather than be surprised with what is coming.

The book has resonated not just with individuals trying to prepare and be forewarned and forearmed as jobs decline but work opportunities rise but also by CEO’s who realize that as every aspect of work shifts the strategies and organizational designs of their have to reinvented in a hurry.

Universities have taken to the book to prepare students for the new work places, and HR societies including SHRM have had me discuss how this is the best and worst time for HR and Learning and Development teams. The best of times because training, organizational design and leadership rethinking will be central but the worst of times because it will require HR to reinvent itself first and fast for a world where employees will both be human and ai, where most workers will not be full time employees and in fact most of the work force will not just work from anywhere but in completely new ways.

Recently I spoke with the leadership of a major company and they asked that since it had been a year since I last edited the book what had I got wrong?

One thing.

Things are moving much faster than I anticipated.

The last five chapters of my book describe what companies will look like in 2029 and the specific changes every individual and firm should prepare for. Because of AI doubling in capability every 7 months vs 12 months when I wrote the book, as well as other shifts, I expect the new world order to happen by the end of 2027.

To better illuminate, illustrate and inspire people to re-imagine the incredible world of work I launched a YouTube show earlier this week ( also available as a podcast on Apple and Spotify) called The Rethinking Work Show where the best people in the world from CEO’s to Academics to HR leaders to Architects to Technologists to Entrepreneurs will share their best learnings from all over the world.

Ria Tobaccowala our elder daughter who is an accomplished film maker is side-gigging a project for her dad and has plans to make this far more visually and well produced but we had to get started and then begin refining.

If you watch (or listen) to the first episode where I speak with Raj Choudhury of Harvard Business School and the author of the recently released book “The World is Your Office” you will see what we are aiming at. Basically amazing people with data backed perspectives to help each of us completely rethink where work is going.

Like this Substack and my podcast What Next? the show is a gift with no cost and no advertising.

Episode 1: Work From Anywhere.

Here are some of the key points made by Dr Choudhury:

1. The future will be work from anywhere (where one chooses where one want to live ) which is even more flexible than remote and hybrid. Data shows that it is allowing companies to hire the best talent, replace fixed costs with variable costs, and align with the AI age where digital twinning and generative AI will turbocharge knowledge sharing, asynchronous work and bring work and factory to the person versus the person to the work.

2. Despite the headlines of companies insisting people return to work the real flow is in the opposite direction. Research does not prove that RTO changes a companies success metrics but it does result in a 10 percent attrition which is probably what most companies are trying to do ( reduce head count without severance). In fact there is data that the more flexible companies are growing faster and more flexibly!

3. In the episode Dr Choudhury shares case after case all over the world from Unilever in Brazil, to Power Companies in Turkey to Hospitals in New York where digital twinning is separating location from expertise as well as companies.

4. We discuss the three pushbacks that work from anywhere enthusiasts need to deal with which are knowledge sharing, communication and culture and every one of these are turned on their head. For instance research shows that unless you work within 75 feet of somebody all this serendipity of water cooler conversations will not happen. Today with generative AI knowledge sharing is no longer an issue and we will all have little Yoda’s and ET’s to talk with. Also in most cases communication that is asynchronous allows for more diverse perspectives, better ideas and deep thinking. Just take a listen and you will forever think differently.

5. Most importantly Dr Choudhury shows how firms do not have to go all in on a new way of working but shows how companies can phase in different ways of working which need to be customized for different teams. The key is a one size fits all model that many companies are trying is probably the worst of all worlds.

In less than 40 minutes you will come away different. Take a listen to Episode 1. Subscribe and every week there will be another world class person providing you ways to truly grow and transform and rethink work.

The Rethinking Work Show can also be streamed as a podcast on Apple or Spotify

Here is Apple:

Here Spotify:

All the ways and places you can get the book: https://rethinking-work.io/whats-inside-2

Ruptures in the Mediascape: What Next?

Photography by Reuben Wu

Over four years ago, I published a post called Ruptures in the Mediascape which correctly anticipated 1) the rising importance of commerce media like Walmart.Com and Amazon, 2) The massive influence and rising impact of podcasts, 3) TikTok’s exponential growth, 4) the renaissance in Out of Home Media 5) the likelihood that Meta would find a way around Apple’s privacy initiatives and 6) how creator and influencer media would eclipse traditional media.

The one thing I got wrong was the belief that the major streaming platforms would remain ad-free by failing to anticipate how expensive they would get without ads due to multiple price increases and the crack down on sharing passwords. Today the ad supported tiers are the same price as the ad free tiers were four years ago!

So What Next?

I believe we are now going to see ruptures that are far more significant and deeper happening between now and the end of next year, which will require every business not just those in the media and marketing space to re-imagine many aspects of their products, services and go to market strategies.

Photography by Reuben Wu

Here are 6 shifts in the mediascape already underway and their implications:

1. The Rise of Poetry versus Plumbing: For the past two decades digital media has primarily been built on advances in infrastructure or plumbing to find the right person at the right person at the right time. The point of contact has been enhanced but the content which is the interaction, creative or messaging has not been as customized or personalized due to the high cost of doing so.

Today, with a plethora of new tools like Veo 3, Sora, Runway ML, Suno, Mid-Journey and others we will see a renaissance of customized creativity. The Poetry that builds brands and resonates with hearts and minds will now match the Plumbing that enhances relevance by finding the right eyes and ears at the most appropriate time.

For many years media was a second class citizen and then came to dominate agencies and service providers. Media will continue to remain critical but creativity and story-telling will move from the caboose to the front of the train too.

2. Conversation the third Interface: Today, two interfaces dominate media particularly digital media: Search and Streams. These will be joined by a third which is Conversations. Whether it be the back and forth with Chat, next generation messaging or Agents interrogating and driving outcomes we will see conversations become a key interface which will also further the rise of voice as an input device besides typing and finger swiping.

Some of these conversations will be about relationships ( today the most popular AI apps are where people look to AI for relationships or growth) and the next CRM will use variations of these conversation interfaces while many conversations will be about getting answers.

One of the reasons Search Engine Marketing works is because Search does not.

If we got the answer we were looking for would we hunt and peck across a sea of links? Companies and interfaces are going to have to be answer optimized.

My friend Pete Blackshaw, the founder and CEO of Brandrank.Ai posits that SEO ( Search Engine Optimization ) will be replaced with AEO ( Answer Engine Optimization)

3. Anticipation the step beyond Personalization: Combine the ability to customize creativity and messaging with the ability to surface answers in real time and the persona based research enabled by AI and the best marketing will not just personalize but anticipate what one needs when one needs it.

In addition to the first moment of truth and then the zero moment of truth movements in marketing we are now going to hear about the minus one moment of truth where the best anticipator will win over the best personalizer.

Photography by Reuben Wu

4. The rise of the Experience Stack: The new marketing stack will combine real, digital, immersive, virtual and mixed experiences to anticipate needs and create impactful storytelling, commerce and services. The real will be the physical world including events, concerts, out of home and physical stores, the immersive will incorporate gaming and interactions such as the Sphere in Las Vegas, the digital will incorporate the next generation of today’s open and closed web and apps, while the virtual will include VR and spatial computing such as Oculus and Vision Pro and mixed experiences will be built around AR glasses from Meta, and AI/XR glasses and Project Astra from Google.

The trick will be to combine these experiences in ways that anticipate, allow for conversations and answers while delivering interactions that win hearts and minds.

5. Platforms become Outcome Engines: In a recent conversation with Ben Thompson which is worth a read Mark Zuckerberg spells out one of his visions for Meta as follows:

A client comes to Meta and says “I want customers for my product,” and Meta does everything else. It generates photos and videos of those products using AI, writes copy about those products with AI, assembles that into an infinite number of ads with AI, targets those ads to all the people on its platforms with AI, measures which ads perform best and iterates on them with AI, and then has those customers buy the actual products on its platforms using its systems.

Mark said the quiet part loud but that is the model with which the supposed decline in search engine marketing revenue for Google is offset. Google combines You-Tube, AI mode of search, Google Lens, Gemini, Project Astra, Project Mariner, Flow and more to drive outcomes not just search results or contextual advertising. Play around at Google Labs and you can imagine these great tools leveraged by the marketing and engineering talent they have collected over the years to drive outcomes: https://labs.google/

It will not just be Google and Meta but also Amazon and Walmart and many others that will morph from platforms to outcome engines.

6. Brands will continue to matter but will be built and sustained in new ways through a fusion of carbon based humanity driven emotional levers combined with next generation mathematics and technology: People choose with their hearts and use numbers to justify what they just did.

Without a person’s need to belong, stand out, aspire, be inspired and story tell there would be no brands. If all that was needed was a superior product at a fair price there would really be no need for brand marketing. A brand is far more than the utility of the product but also involves desire, provenance, design, storytelling and much more.

A brand has been a trust mark that stands for a promise. A brand is about integrity where what the brand delivers, what a brand says and what a brand believes are aligned. A brand is about a story of the product, the buyer, the culture around it and more.

In an AI age Trust, Integrity, Story-telling, Cultural resonance will matter but will be architected, honed and sculpted using conversations, anticipation, experience stacks, outcome engines and most importantly poetry and not just plumbing.

And it will not just be the tech but the talent, the taste, the voice, the touch and the not yet imagined that will create and sustain the next generation of great brands.

But every company needs to interrogate themselves on the products and services they can create or sustain which complements or supplements outcome engines. What value can we add in addition to those of outcome engines?

We should ask if we have the right talent, urgency, partners and organizational structure to navigate experience stacks and remain relevant in a world where every product will also be a service due to conversation and agent technologies.

The future while uncertain is coming fast and definitely will not fit in the containers most incumbent companies have designed for today…

This is the 251st edition of The Future does Not Fit Into the Containers of the Past Substack. Here is a single page with access to the 100 best pieces written over 12 different subject areas including The Future, Managing Change, Upgrading Our Mental Operating System, Selling Better, Building Cultures, Managing Careers, Wisdom and much more. All completely free and read by 30,000 executives. https://Rishadtobaccowala.com/100

The Future Fits on One Page.

This is the 250th edition of “The Future Does Not Fit in The Containers of the Past”

Published every single Sunday morning for 250 weeks at around 8 am Chicago time.

The first edition of this thought letter was published on August 16, 2020 began like this…

Welcome to my first issue of “The Future Does Not Fit in The Containers of the Past” newsletter. Thank you for subscribing.

What I hope you will get from this newsletter

The idea behind this newsletter is that of a gift.

Like a gift it is free (no subscription fee, no up-charges to access special content, no advertising, no affiliate links, your email will not be shared or sold, and no algorithm is running in the background mining your behavior)

Like a gift I hope it will be of some value in helping you see, feel and think differently about how to grow yourself, your team and/or your company in the future.

Like a gift, I hope it will generate goodwill for the giver. Your attention and time which is so valuable. Good karma. Stronger relationships.

This newsletter will be bohemian and eclectic in that it will mix art and science, it will have a certain wanderlust and will roam into different areas…

Today nearly five years later more than 350,000 words or nearly 7 books of content have been written and shared. Subscribers have grown from 500 to nearly 30,000. The thought letter has remained completely free of monetization. And the range of topics have wandered far and wide with the writing steering away from only from politics and news.

In keeping with the gifting orientation that drives this thought letter I have curated the best 100 pieces of writing and organized them into 12 areas which are now all accessible from a single page here or at https://rishadtobaccowala.com/100

I provide an overview of the sections and the best pieces below. But first here are the five most popular pieces over the past five years listed in order which indicate the range of the writing.

Re-thinking Presentations. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 55.

Read on Substack

Small Things. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 195.

Read on Substack

A Company of One. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 155.

Read on Substack

Re-Invented Marketing: 5 Shifts. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past.Edition 241.

Read on Substack

Avoiding Career Irrelevance. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 223.

Read on Substack The 12 Areas of Writing

1. The Future: Here are articles on The Four Shifts that are driving the future, a series of pieces on Why AI is Under-hyped, How to remain relevant in an AI age and How to Upgrade our AI quotient as well as Ten Forecasts for the Next Decade and how to avoid Strategic Myopia.

2. Managing Change: To manage change in ways that suck less we need to follow the 6 Keys to Change while curing ourselves of Inner Dinosaur Disease and learn to Think Like an Immigrant.

3. Upgrading our Mental Operating Systems: Our phones have upgraded their operating systems in the last 18 years how many time have we? This section shares how to be better at Learning to Learn, How to Think Better, and how it is key to think from Both Sides Now.

4. Enhancing Effectiveness: So much of our lives our spent attending meetings. What if everything we have been told about how to be effective in these areas are wrong? Rethinking Meetings shows how we do not attend meetings but stare-a-thons and most of given advice on how to run meetings are wrong! Understand the importance of Tattoo Moments and why Fewer is better.

5. Becoming A Leader: In an Age of De-bossification here are Four Keys to Leading Today and 8 Management Lessons from some great leaders.

6. Rethinking Media, Marketing and Creativity: In a single graphic the last four decades of change in marketing and where it is going are shared in Re-Invented Marketing: Five Shifts. A very popular piece was on why the Future of Marketing is People and how we are entering an Age of Creativity.

7. Selling Better: To close more sales it is key to understand the 8 Things Customers Want, why one must spend time Rethinking Presentations and how Small Things matter and every time one wants to sell one must frame and filter using S.A.V.E.

8. The Future of Work: A series of articles which foresaw the world we live in today including why we are living in Career Bending Times and how most companies could get Returning to the Office right.

9. Creating Great Cultures and Future Forward Organizations: What are the key components of Cultures. Why it is important to call out The Turd on the Table, to combine Roots and Wings and recognize that Generosity is a Strategy.

10. Managing Careers: How do we thrive in a world of Fifty Year Careers where we are going to see the Decline of Jobs. The Rise of Work. The key exercise for Career Turbocharging and all the lessons of a Career Revisited and why everyone must learn to work like a Company of One.

11. Personal Growth: We become who we are through Chances, Changes and Choices, learning the importance of Repairing Ourselves, finding times to go Vagabonding and learning the limits of things in On Stuff

12. Wisdom: We chase after it but what can we learn about Architecting Joy, find Grace, the importance of Appreciation and how life is about Loss, Love and Learning.

You can find all these pieces and much more available completely free to use and leverage as you like all accessible from a single page here or at https://rishadtobaccowala.com/100

Thank you for being a reader.

Your time is rare and therefore your attention is a gift.

If you ever wanted to introduce this writing to others this might be the ideal post to share.

...

This is the 250th edition of “The Future Does Not Fit in The Containers of the Past”

Published every single Sunday morning for 250 weeks at around 8 am Chicago time.

The first edition of this thought letter was published on August 16, 2020 began like this…

Welcome to my first issue of “The Future Does Not Fit in The Containers of the Past” newsletter. Thank you for subscribing.

What I hope you will get from this newsletter

The idea behind this newsletter is that of a gift.

Like a gift it is free (no subscription fee, no up-charges to access special content, no advertising, no affiliate links, your email will not be shared or sold, and no algorithm is running in the background mining your behavior)

Like a gift I hope it will be of some value in helping you see, feel and think differently about how to grow yourself, your team and/or your company in the future.

Like a gift, I hope it will generate goodwill for the giver. Your attention and time which is so valuable. Good karma. Stronger relationships.

This newsletter will be bohemian and eclectic in that it will mix art and science, it will have a certain wanderlust and will roam into different areas…

Today nearly five years later more than 350,000 words or nearly 7 books of content have been written and shared. Subscribers have grown from 500 to nearly 30,000. The thought letter has remained completely free of monetization. And the range of topics have wandered far and wide with the writing steering away from only from politics and news.

In keeping with the gifting orientation that drives this thought letter I have curated the best 100 pieces of writing and organized them into 12 areas which are now all accessible from a single page here or at https://rishadtobaccowala.com/100

I provide an overview of the sections and the best pieces below. But first here are the five most popular pieces over the past five years listed in order which indicate the range of the writing.

Re-thinking Presentations. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 55.

Read on Substack

Small Things. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 195.

Read on Substack

A Company of One. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 155.

Read on Substack

Re-Invented Marketing: 5 Shifts. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past.Edition 241.

Read on Substack

Avoiding Career Irrelevance. by Rishad Tobaccowala

The Future Does Not Fit in the Containers of the Past. Edition 223.

Read on Substack The 12 Areas of Writing

1. The Future: Here are articles on The Four Shifts that are driving the future, a series of pieces on Why AI is Under-hyped, How to remain relevant in an AI age and How to Upgrade our AI quotient as well as Ten Forecasts for the Next Decade and how to avoid Strategic Myopia.

2. Managing Change: To manage change in ways that suck less we need to follow the 6 Keys to Change while curing ourselves of Inner Dinosaur Disease and learn to Think Like an Immigrant.

3. Upgrading our Mental Operating Systems: Our phones have upgraded their operating systems in the last 18 years how many time have we? This section shares how to be better at Learning to Learn, How to Think Better, and how it is key to think from Both Sides Now.

4. Enhancing Effectiveness: So much of our lives our spent attending meetings. What if everything we have been told about how to be effective in these areas are wrong? Rethinking Meetings shows how we do not attend meetings but stare-a-thons and most of given advice on how to run meetings are wrong! Understand the importance of Tattoo Moments and why Fewer is better.

5. Becoming A Leader: In an Age of De-bossification here are Four Keys to Leading Today and 8 Management Lessons from some great leaders.

6. Rethinking Media, Marketing and Creativity: In a single graphic the last four decades of change in marketing and where it is going are shared in Re-Invented Marketing: Five Shifts. A very popular piece was on why the Future of Marketing is People and how we are entering an Age of Creativity.

7. Selling Better: To close more sales it is key to understand the 8 Things Customers Want, why one must spend time Rethinking Presentations and how Small Things matter and every time one wants to sell one must frame and filter using S.A.V.E.

8. The Future of Work: A series of articles which foresaw the world we live in today including why we are living in Career Bending Times and how most companies could get Returning to the Office right.

9. Creating Great Cultures and Future Forward Organizations: What are the key components of Cultures. Why it is important to call out The Turd on the Table, to combine Roots and Wings and recognize that Generosity is a Strategy.

10. Managing Careers: How do we thrive in a world of Fifty Year Careers where we are going to see the Decline of Jobs. The Rise of Work. The key exercise for Career Turbocharging and all the lessons of a Career Revisited and why everyone must learn to work like a Company of One.

11. Personal Growth: We become who we are through Chances, Changes and Choices, learning the importance of Repairing Ourselves, finding times to go Vagabonding and learning the limits of things in On Stuff

12. Wisdom: We chase after it but what can we learn about Architecting Joy, find Grace, the importance of Appreciation and how life is about Loss, Love and Learning.

You can find all these pieces and much more available completely free to use and leverage as you like all accessible from a single page here or at https://rishadtobaccowala.com/100

Thank you for being a reader.

Your time is rare and therefore your attention is a gift.

If you ever wanted to introduce this writing to others this might be the ideal post to share.

The Decline of Jobs. The Rise of Work.

This past week I had the great opportunity to speak with 60 of the most senior leaders at a major financial firm whose heads of Data and AI had bought 150 copies of my new book, Rethinking Work for their teams and asked me to do a Q and A webinar.

One of the questions was what had changed in the time since I finished writing the book ( July of 2024) and today nearly a year later?

My answer was that the shifts I was predicting which would require us to rethink work were happening faster, in more places and with greater impact than I anticipated. What I predicted for 2028 /2029 were likely to scale in 2026/2027 but the suggestions, ideas and blue prints on how each individual and firm could adapt remained the same.

Companies have been built around the concept of jobs as a way of getting work done but increasingly jobs will be disconnected from work.

The big transition underway is from employment that is full time and done by employees who have jobs working in an office to a world where work will be done by fewer people who will mostly be away from an office who will not have full time jobs.

Unless companies rethink everything from strategy to organizational design to financial metrics to training from the ground up for where the future of work is going they will find themselves increasingly replaced by new entrants who a) source talent from anywhere in the world in highly agile and flexible ways, b)are AI first, c) invest deeply in learning and d) have talent programs reflecting the realities that reflect the different mindsets of multiple generations and an aging and declining population.

From a recent Fortune Article

In a pilot project, McKinsey built an AI agent using Microsoft’s Copilot Studio software that can monitor an email address for incoming project proposals from potential clients. When one arrives in the inbox, the agent automatically assesses the job, estimating the staffing requirements, time to completion, and budget.

It even suggests which available consultants should do the job. A human still must check what the agent produces, of course, but the technology has cut the time required to scope out a project from 20 days on average to just two days.

What impact will AI agents have on workers? “I think it will be really disruptive,” says Craig Le Clair, an analyst at research firm Forrester and the author of Random Acts of Automation.

He knows of one Netherlands-based insurance company that had 15 contractors in Bulgaria helping to process claims-related emails. The contractors determined whether an email was about a new claim or an existing one, and made sure any information, including attachments, was uploaded to the appropriate databases. AI agents now do this work—and the company fired all the Bulgarian contractors.

Read Tobi Lutke the CEO of Shopify’s memo on why he expects no additional headcount will be approved at Shopify unless it can be proved that AI cannot do it and how the entire company is going to be rewired for a new age. Whether you are a CEO or an intern it is a must read.

Recently for an AI council for marketers which I chair I sent them this article from Ethan Mollick’s substack One Useful Thing ( an absolute must subscribe) and asked them to put in the same prompt( which is in the next paragraph) but for their category or brand.

Here is the prompt Ethan put in to ChatGPT o3 model:

“ Come up with 20 clever ideas for marketing slogans for a new mail-order cheese shop. Develop criteria and select the best one. Then build a financial and marketing plan for the shop, revising as needed and analyzing competition. Then generate an appropriate logo using image generator and build a website for the shop as a mockup, making sure to carry 5-10 cheeses that fit the marketing plan.”

Here is what Ethan found:

With that single prompt, in less than two minutes, the AI not only provided a list of slogans, but ranked and selected an option, did web research, developed a logo, built marketing and financial plans, and launched a demo website for me to react to. The fact that my instructions were vague, and that common sense was required to make decisions about how to address them, was not a barrier.

The question I then asked them is that if their CEO and CFO has done the same exercise and come to ask them to justify their head count and the way they currently work what would they say?

In the past 10 days I have been in two different meetings where the next revision of the multi-modal capabilities of the next version of Gemini by Google have been previewed and they far surpass (at least for the time being) the capabilities of Open AI models.

This is not the time for task forces but to align with the force of change with a sense of urgency and scale to reinvent companies

It is not just AI but many other things that are going to create the most dramatic shift in the loss of jobs but the rise of work.

I asked the same ChatGPT o3 Model to answer the prompt “why might we being see the decline of jobs but the rise of work? “

After 41 seconds of analysis here is what I got:

“Jobs” ≠ “Work”

Official payroll jobs are a narrow concept: a single employer, a W‑2, a slot in the BLS counts. Work is everything people do to create value, paid or not, whether it shows up on a company’s head‑count or not. Once you separate the two, the paradox becomes clearer:

Why payroll jobs can flatten or fall…

Automation & AI: Firms can keep revenue rising while head‑counts stay flat. U.S. job openings slid from 8.1 million in March 2024 to 7.2 million in March 2025 even though output kept growing. Bureau of Labor Statistics

Demographics: Retirements outpace new entrants in every rich economy; a smaller workforce limits the absolute number of jobs that can exist.

Risk off‑loading:Companies re‑label employees as contractors or outsource entire functions, removing positions from the payroll tally without killing the underlying tasks.

Capital‑first business models: Software, cloud services and robotics make it cheaper to buy capacity than hire people, so fewer traditional roles are created per dollar of GDP.

While work is exploding (but often invisible to job statistics)

Gig & platform labor: At least 70 million Americans will freelance in 2025, on track to pass 86 million by 2027—meaning a majority of workers will earn income outside a W‑2 at least part‑time. Fortunly

The creator / micro‑entrepreneur economy: YouTube, TikTok, Substack and Shopify have spawned a $250 billion creator economy where millions earn revenue shares, sponsorships, or merch sales—none of which count as “employment.” Forbes

Solo & very‑small businesses: Record formation of 5.5 million new business applications in 2023 shows a surge of one‑person LLCs and side‑hustle ventures. These founders are working—sometimes 70 hours a week—but they don’t appear as employees. U.S. Chamber of Commerce

Unpaid but indispensable care work: Family caregivers now provide labor valued at ~$874 billion a year in the U.S.—bigger than the pharmaceutical industry—yet it is entirely off the payroll radar. Axios

Open‑source coding, online tutoring, volunteer crisis mapping, fan‑translation, DAO moderation—all productive, often time‑intensive work outside formal employment.

AI leverage: One skilled person plus copilots or low‑cost bots can do the output of a small team, so head‑counts shrink even as the task volume—and value—expands.

Its time to rethink work

6 Ways to Lead Today.

We have entered an age of De-bossification

There is a rise in the need for leaders, guides, coaches, mentors, role-models, creators, and builders who manage through a zone of influence.

Less of a clamoring for bosses, managers, monitors, evaluators, and paper pushers who manage through a zone of control.

Every one can be a leader whether we manage people or not.

Six ways to lead today:

1. Be Distinctive

Companies, brands, and individuals which succeed are ones that differentiate themselves.

Stand for something.

Have a distinct point of view.

Provide a different perspective.

Craft a culture and a way of working.

Build a network and teams of diverse and the different and let them be them and free to speak out if you want to have a truly different product or service or grow your own skills.

2. Be realistic but also a source of enlightenment and inspiration.

All businesses can be tough.

A leader must face and accept reality.

But also enlighten and inspire.

It is very easy to get down and be negative given all the challenges that come with great velocity every day having to deal with persnickety customers, technology shifts and aggressive competitors.

We can all be caught in a frenzy of urgency, twisting, and twitching with cyclonic vigor in attending to the matters at hand.

But never forget that people are looking to leaders to show the way forward.

Try to end every meeting and interaction with a sense of clarity (what to do next), belief ( the team believes in the cause and themselves) and energy ( they leave motivated and filled with gusto to tackle the challenges and opportunities)

3. Look over the horizon for what is next.

Be besotted with what lies ahead.

Tomorrow is where we and our companies will spend the rest of our lives and we need to look over the horizon.

Whenever we are surprised as leaders or companies it’s because somebody made tomorrow tangible today first while we were solving yesterday’s problems.

4. Renew. Refresh. Re-invent.

In a complicated world filled with hurly burly speed and messy things called people things often go wrong.

Snafus of communication and differences in expectations, incentives or approaches will lead to wires crossed and hurt feelings that can sever ties and relationships.

We sometimes need to renew and restore and repair relationships even if it means eating humble pie sometimes when we do not have to or want to.

We constantly change as people, and we need to see each other from time to time with new eyes.Do not put people in a box and think you have them figured out. They change.

5. Combine roots and wings.

Peoples past beats like a second heart within them just like the roots and history of brand and companies have twisted them into their current shapes.

Every successful individual, brand, and company is fed by their roots, but they aspire to change, grow, and adapt and fly with wings.

Wings without roots often get blown away.

Roots without wings wither and die.

Fusing roots and wings is the way.

6. Protect, guide and build people.

In the end as leaders our first and foremost job is to protect and guide and help grow and transform people since we scale through our people. Companies do not grow or transform, people do.

The most talented will sometimes lose their way or come to a fork in the road and begin to question themselves, where they are and where they are going.

By protecting, guiding and building not only would we do the right thing, but it is this behavior that will attract and retain talent for the long run.

...

What is strategy?

Strategy is Future Competitive Advantage.

What will the future look like? What will people need and expect? How will demographics, technology and other global shifts create new competitors or recharge current competitors and how will categories blur, blend and maybe even disappear?

Amidst these new expectations and changing competitive dynamics what advantage will your company offer? A differentiated or better product? A competitive moat of network effects, scale or some other dynamic? A better experience? Speed and value?

While Strategy firms can be amazingly helpful in guiding companies through these questions, most leaders already have a gut instinct on what needs to be done. The deep dive documents, the chanting strategists and the long march of meetings are to bring others along and to provide an intellectual and analytical framework for a decision that clearly had to be made.

If you work for a firm and you have an idea of where the future is going and how changing people’s expectations and emerging technology are going to create challenges or opportunities, you should go to your management and share your thinking.

All you need to talk about is future competitive advantage.

Why strategies often fail in implementation.

Companies often allocate large swaths of senior management time and budgets for outside specialists to help them sculpt and then move the strategy forward.

A cavalcade of consultants convey and communicate with countless charts and creative conjuring to the C-Suite.

A flurry of futurists frame, focus, and filter the way forward with the finesse of fortune tellers.

Masters of the Universe market M&A moves that might make multiples move upwards and mean many more millions in market-cap.

PR professionals produce and promote points of view that provoke the press to perceive with pristine perspectives.

These efforts when successful result in the first three key steps to strategy implementation

1) A simple and differentiated strategic blueprint.

2) An M&A plan to acquire skills, markets and technology.

3) A re-organization since the future does not fit in the containers of the past.

These are essential ingredients to a recipe of change and growth none of these will work without helping grow and change the people in the organization.

Because while firms are a collection of ideas, technologies, patents, brands, ecosystems and people, it is people who are the key since they create the ideas, technologies, patents, brands and eco-systems!

Michael Tyson said, “Everyone has a plan till they get punched in the face”.

Boards and leadership of firms come quickly to the realization that everything is easy until people get in the way.

Telling people that change is good, threatening them with job loss if they do not change or creating communication materials and slogans to goad them into a cult like devotion to the new dear leader or the way forward rarely works in the short run and will likely fail after the threat of flagellation fades.

Because if there is nothing in it for them, people will out-wit, out-wait, out-pretend, and out-maneuver “management”. Until then they will fill the time genuflecting and bowing and going through the monitored motions of attending the right meetings, muttering the motivational mantras and stating the slogans required.

The keys to implementing strategy.

If a strategy is to be leveraged in ways that transform an organization, it is key to remember that the only true transformation happens is when the mindsets, skillsets and behaviors of the people working for the firm transform.

If you want your organization or team to grow and change you will need to ask your team to initiate a) a three-question exercise while leadership b) delivers three clear answers to employees.

The Three Question Exercise every team should consider doing so they can both understand, get aligned with and contribute to strategy.

1) How do we expect peoples as well as our customers/consumers/members needs and expectations to change in the future?

2) What are our key strengths and weaknesses in meeting and aligning with these shifts?

3) I3) If we had no constraints except that we had to ensure that what we did was legal, that it was technologically possible and financially broke even in 3 years or less what products and services would we design? Alternatively if we gamed ourselves as a new entrant in attack mode how would we take market share away from ourselves on a particular product or customer segment?

This exercise makes people look up from their day to day and understand risks and opportunities and helps them realize the need for doing things differently. As importantly it gets them to contribute and activate the strategy in their areas of competence and expertise. It also allows leaders to go into attack mode versus thinking only defensively.

The Three Clear Answers management needs to deliver to company staff in order for them to align with and implement the strategy:

1) Why are the recommended changes good for their personal career growth?

2) What are the monetary or other incentives to change?

3) When and where will training be provided to help them learn the new skills needed?

Change does not happen because of M&A, press releases, re-organizations or a new leader, all of which undoubtedly play a role.

An organization changes and grows when the people in the organization change and grow.

Images created using Mid-Journey