"Guide Yourself By The Stars And Not The Passing Ships"
What would it be like to get some career advice from someone who has mentored over 30 CEO’s of billion dollar companies?
David Kenny has had a four decade long career beginning as a consultant at Bain to co-founding and leading Digitas which he sold to the Publicis Groupe where he was part of the Directoire+ . David then went on to leadership roles at Akamai, The Weather Company, IBM Watson and Nielsen. Today David is a director at Nielsen and Best Buy (he was a former Chairman of both) as well as Flutter. David recently stepped down as the Chairman of the Board for Teach for America due to term limits.
David joined Drew Ianni and myself on the latest Unbossing Podcast and in just 30 minutes provided a master class of how to lead and thrive in changing times by not just learning but unlearning and not just leading but unbossing.
The links to the show are below but here are some highlights:
1. It is important to remember what has not changed.
Much is shifting in a world of uncertainty. The big changes are not just AI, but also shifting consumer behavior, new employee expectations, and the changing perception of the US globally.
In a world of change it important to keep in mind what has not changed which include that we all have limited time and resources. We are all limited in how much we have. We can be more productive but we cannot create more time.
Another thing that has not changed is most humans are kind and decent and want to do the right thing.
2. Guide ourselves and our companies by the stars and not passing ships.
Too many companies are focusing on the next shiny object including launching dozens of AI pilots to show that they are doing things to mollify financial markets or Boards of Directors.
This is the equivalent of guiding companies by vibe or news release. Technology should be subservient to the goals and values of a company.
3. Expertise will matter less while curiosity and particularly resilience will matter more.
Expertise will matter less in an AI age. Knowledge is becoming free and expertise is often easily accessible in many areas. What will matter more is the ability to ask questions and learn.
David reminds us that even the best talent will make a lot of mistakes and suffer set backs. It is those who learn to overcome mistakes that thrive. The ability to practice resurrection will be key.
4. Diversity is a competitive advantage and it is about meritocracy.
Inclusion is the best way to unleash all the talent in an organization. It allows a company to get the most out of people.
It is critical that inclusion is aligned with business outcomes and meaningful results and not for just the sake of inclusion.
DEI creates much more of a meritocracy by providing an opportunity for all talent to compete and the lack of it is what is non meritocratic!
5. Two Things to Unlearn
Among the many things we need to unlearn are the following beliefs:
a) That Humans are better than Machines: Increasingly this is not true and in many areas machines will do much better job than humans. We should be outcome focused versus input obsessed.
b) Hierarchical Organizations : Increasingly defunct. AI is changing organizational design and the reality is that those those on the front lines with connection and relationships with customers have more real time information and ability to solve problems and leverage opportunities.
6. Speed without direction can kill a company.
Velocity is speed with direction. Today so many AI pilots are about speed without any connection to the direction of the company. It is not how fast but how aligned the direction of travel is with the north star of a company.
7. A little fear is good but managing by fear should be eliminated.
A little fear is motivating. Especially the fear of a person or a company becoming irrelevant.
To manage our own fear swe should ask what we fear and what is the worst that can happen? Often trial and error overcomes fear versus being frozen because of fear.
On the other hand, managing through fear demotivates a company and can be very corrosive. Managers who leverage fear hurt a culture much more than the supposed success they may deliver.
Companies must weed the garden by removing those who manage by fear.
8. Companies are making a mistake by not hiring youth because of AI.
Generation Alpha today uses AI as an operating system while Gen-Z uses it as search and the rest of us are figuring it out.
The young can teach us a lot about how to run things in an AI age and it is a mistake not hiring them if a company truly wants to become AI first.
9. Management is very different than being on a Board.
Boards are keeper of values of a company. To ensure that the company does not lose its true north.
Boards are a team sport and the Chair of a Board is like a coach.
Boards should never manage but be a back stop and gut check for management.
Much much more on the podcast:
Unbossing guests have included Reed Hastings the co-founder of Netflix, Tariq Hassan the former CMO of McDonalds, and Jim Lesser the Chief Brand Officer of Service Now. Future guests include Janet Foutty the decade long CEO of Deloitte Consulting, Ann Mukherjee the former CEO of Pernod Ricard and a leader at SC Johnson and Pepsi, Jim McCann the founder and CEO of 1-800 Flowers, Sarah Personette the CEO of Puck and leader at Twitter and Meta among many others.
Listen to Reed, David and others on Unbossing wherever you listen to Podcasts. Here are Apple, Spotify and YouTube links:
Apple:
Spotify:
YouTube:
One Single Thing
Last week one Pulitzer Prize winners was a story titled: He’s Dying. She’s Pregnant. It won for feature photography and is a must read.
Here is the link: https://www.washingtonpost.com/health/interactive/2025/tanner-shay-martin-baby-colon-cancer-end-of-life-planning/
Anti-Internet Writing.
Image by MidJourney
This is the 300th edition of “The Future Does Not Fit in The Containers of the Past”.
400,000+ words published 300 Sundays in a row, covering 12 different themes, subscribed to by 32,000 individuals.
For this 300th issue, ChatGPT, Claude and Gemini accessed all 299 prior posts and provided a critique and analysis of the entire body of work over the past six years.
Below is a synthesis from the 3 engines:
1) Four Lenses.
All the writing can be viewed through four lenses:
The World. The Firm. The Craft. The Self.
A curated selections of posts from each theme organized by lense is accessible here:
https://rishadtobaccowala.com/100
2) An Operating System for Modern Leadership.
Google Gemini took a bird’s-eye view, analyzing the connection between these 299 posts into a larger whole:
“Rishad Tobaccowala’s Substack, “The Future Does Not Fit in the Containers of the Past,” is a high-frequency (weekly) masterclass in navigating the intersection of technology, humanity, and business.
Reaching its 299th edition as of May 2026, the archive functions less like a series of blog posts and more like a modular book on “Modern Wisdom.”
If you zoom out: This is not just a Substack. It’s a serialized operating system for modern professionals. Each post = small upgrade. Entire archive = full system. Leverages framework thinking: “5 shifts,” “6 keys,” “10 lessons”.
Actionable inspiration. Not just insight but what to do next. Very operator-focused.
3) “Anti-Internet” Writing.
ChatGPT calls it “ anti-internet writing” because:
a) It has a distinctive quality in its tone and voice: Calm, reflective and non-urgent. Authority without aggression. It blends a CEO memo, a philosophy essay and a personal letter while avoiding hot takes, outrage or trend-chasing.
b) The content is evergreen as it is not tied to news cycles.
c) It distills half a century of learning and makes it available without any monetization.
Instead of analyzing on tone of voice and style, Claude did a meta take on how the thinking has evolved over the past six years:
4) Tectonic Times
Most companies and leaders today are rightly fixated on AI. But technology including AI is but one of five shifts underway. One of the shifts is the need for leaders to reinvent how they lead to remain relevant in these tectonic times.
5) A Distillation of the Four Lenses.
Here are four slides which distill each of the four lenses (World, Firm, Craft and Self) that my writing covers:
Every single key piece that comprises the themes and makes up the lense is available to access on this one page: https://rishadtobaccowala.com/100
6) The Key Frameworks and Takeaways.
The best way to learn and remember is via frameworks and summarized takeaways.
The writing has included dozens of usable frameworks to help people think differently including how to solve problems leveraging photography.
Here is a sampling of 9 frameworks and 5 takeaways:
7) Tensions/Blindspots
Four key weaknesses are identified including: 1) a macro optimism that may overwhelm micro disruption; 2) the writing is for white collar knowledge workers who are middle to senior leaders and top of organization; 3) little original research; and 4) some key themes repeat.
With the exception of original research, future writing will work to address the blindspots and tensions.
In these 300 posts written over 6 years, the internet has rapidly transformed and the use of generative AI engines is changing the way we work, how we interact, and lead our lives. However, despite the tectonic times and Third Connected Age, staying human will also include “anti-internet” writing like this Substack.
One Single Thing.
If asked to distill learnings into one single slide it is the one below:
Thank you for being a reader. If you believe this writing and thinking can be useful to others please share this post and encourage people to subscribe. It has been free and will remain free and continue to be issued just once a week every Sunday morning.
Asymmetrical Interconnectedness.
Image: MidJourney
There is another AI we need to be thinking of as we plan our futures.
Asymmetrical Interconnectedness.
Scale and size while important are not enough and often can be a disadvantage.
Our societies may be polarized and our leaders more parochial but the world is growing more interconnected.
No strategy can remain relevant if it does not align with or is prepared to defend against competitors who leverage asymmetrical interconnectedness.
Here are three examples of this “other AI”:
1) The Middle East: Iran’s conventional army has been decimated but that has not prevented a combination of their drone and speedboat forces from creating havoc in Strait of Hormuz and also attacking key refineries of oil and data in the UAE.
With 20 percent of the world’s oil and much more of LNG and fertilizer supplies going through the strait it is a chokehold which is causing havoc world wide.
Modern asymmetrical weapons combined with critical connection points can offset armadas of scaled weapons.
The ripple effects have just begun to spread. For instance, the need to allocate more funds on defense and repair due the war might lead to less capital investment in AI data centers from Saudi and UAE wealth funds which will slow the global AI build out.
A poetic reminder of our interconnectedness…
2) The Rise of Influencers: Google Search in AI Mode responding to the question “Please compare Mr Beast vs the Super Bowl”.
“The comparison between MrBeast and the Super Bowl depends on how you measure “traffic”—whether it is a single video’s views, total monthly reach, or instantaneous viewership. [1]
While the Super Bowl remains the largest single-day televised event in the U.S., reaching roughly 124.9 million viewers in 2026, MrBeast generates significantly higher total monthly traffic, with his videos averaging 3 billion views per month across his entire catalog as of 2025. [1, 2]
Viewership Comparison
Single Video vs. Single Game: A new MrBeast video often racks up 50 to 100 million views within the first 48 to 72 hours. His “Squid Game” video has surpassed 354 million views, more than double the audience of any single Super Bowl telecast.
First-Day Traffic: MrBeast holds records for the most-viewed non-music video in 24 hours, reaching 52 million views in a single day.
Total Reach: The Super Bowl’s reach is almost entirely American. MrBeast, however, has a global audience, claiming a unique monthly reach of roughly 1 billion people across all platforms. [1, 2, 3, 4, 5]”
Today individuals scale faster than most television networks using hyper connected platforms like YouTube, TikTok, and Instagram.
Companies like Unilever have over 300,000 influencers aligned with their brand.
From a recent Forbes Article:
Unilever CEO Fernando Fernandez recently disclosed that the company has scaled its direct creator network from 10,000 to 300,000 in just two years, with roughly half of its digital budget now flowing into social-first, creator-led content.
Most of the coverage framed it as a marketing milestone, perhaps the death knell for agencies. Actually, it is something bigger: a structural signal that the creator economy has crossed from a content industry into an acquirable asset class.
The underlying numbers support the shift. Goldman Sachs projects the creator economy will reach $480 billion by 2027, up from roughly $250 billion today. The 2026 Creator Economy M&A Report from Quartermast Advisors documented 81 closed transactions in 2025, a 17.4% year-over-year increase, led by landmark deals including Bending Spoons’ $1.38 billion acquisition of Vimeo,Later’s $250 million purchase of Mavely, and Publicis Groupe’s $175 million acquisition of Captiv8.
A case can be made that Influencers in addition to building their own personal brands and helping companies market their brands are also the true builders of new brands which they then sell to the larger marketers.
Increasingly large companies but have outsourced innovation and cultural resonance to the individual.
Here is a Anthropic Claude chart to the query: “I would like a chart to show the value of recent acquisitions by big companies of influencer brands”
3) New competitors leveraging asymmetry and connectedness to change the rules of the game on many established competitors.
Today, AI allows companies to plug into metered intelligence and capabilities irrespective of their size. While it takes billions to be a Hyper-scaler or a Foundational LLM model builder, it requires a few hundred to a few thousand dollars for any company or individual to leverage these amazing technologies. They then marry this technology with connection platforms such as Amazon, Shopify, Etsy, YouTube, Fiver, Upwork and others to access supply, demand, talent, expertise and capital globally and in real time.
There are some that believe we will one day have a one HUMAN person billion dollar company. ( These companies may have lots of lots of AGENTIC employees).
The chart below shows new companies are leveraging Asymmetric Interconnectedness to drive millions of dollars of revenue per employee. This is matching and exceeding the revenue per employee number of companies like Google and Meta ( in the advertising services business the number is less $200,000 in the US for comparison.)
Implications
Rethink Scale: Scale can still be an advantage in some areas but a disadvantage in others. Today most individuals have better AI capability at home than they have at work. A home they use multiple models and the latest versions of each versus being limited to one pre-approved sand boxed version in the office.
Look at the edge and look below: The next competitors will come from outside one’s categories such as Waymo, Tesla and Uber came from outside the Auto Industry or it will come from the slime which is below where most are looking. The future rarely comes from the heavens. It comes from the slime. Microsoft from MS-DOS when everyone was paying attention to IBM, Google from helping small advertisers who did not advertise to find customers when everyone was looking at the television networks and the Conde Nast and Time magazines of the world.
Question the status quo: First party data will continue to remain important it may matter less and be leveraged very differently in the future. This is because conversational interactions with AI agents and engines are better at revealing preferences and needs of people than todays interfaces of search, scrolling and streaming. Combine this depth of understanding with the ability to provide highly interactive and adaptive solutions or offers in real time and the entire interface of marketing is likely to change.
One Single Thing.
Howard Hawks once said that a good movie is three good scenes and no bad scenes.
Casablanca is a movie with at least 7 great scenes each resulting in a line that millions use every day including:
“Play it Sam. Play As Time Goes By”.
“Of all the gin joints in all the towns in all the world, she walks into mine.”
“ We will always have Paris”
“ Here’s looking at you kid”
“Round up the Usual Suspects”
“Louis, I think this is the start of a beautiful friendship”
“ Play the Marseille”
Casablanca is as relevant today as it was 85 years ago.
It is available globally on every platform ( usually with a subscription) or search for the quotes above and access some of the most famous scenes for free.
Casablanca remains my favorite movie and is ranked #63 in the BFI list of 250 best movies. Here is the BFI list…https://www.bfi.org.uk/sight-and-sound/greatest-films-all-time
Above is a trailer for Casablanca.
And here is “ Play it Sam. Play As Time Goes By”
Reducing Career Anxiety.
Image via ChatGPT
Many of us are anxious about our careers.
We may feel overwhelmed by the velocity of change.
We might wonder whether our skills and experiences are still relevant.
We fear that our jobs will be eradicated by AI.
Our anxiety is natural and human.
Work provides us with not just income, but also identity, community, purpose and growth.
Here is a distillation of perspectives, insights and exercises shared in this Substack over the past six years to help one gain agency over our careers and to anticipate and prepare for a rapidly changing work environment.
Images by MidJourney to the prompt “Pioneering the Future of Work”
1) Understand and align with the three major shifts changing the contours of work.
a. Work and Jobs are uncoupling: 200 years ago most people worked without having a job. A full time job as a primary way to earn an income has already begun to decline and this will accelerate over the next three years in part due to AI and in part due changing demographics and emerging mindsets. We may be at peak full time jobs but not necessarily peak income or opportunity. Companies are often arranged around jobs versus work which may not make sense in a world where “jobs” are just a phase work is going through.
b. A significant percentage if not the majority of a company’s employees in less than three years will be two types of employees that barely existed a year ago. These are agentic employees who will have their own email addresses, own logins and will be managed by newly trained HR and Talent teams. Another group will be fractionalized employees who have all the benefits, including health care but work 3 or 4 days a week as a result of AI replacing some work. This move to fractionalized employees will also be turbo-charged by new marketplaces that are allowing people to have a salary and health care augmented by other forms of income. The fractionalized employee will be a necessity that companies will have to adjust to given the demographic reality of aging populations who may need to keep working to augment savings or to just to keep connected and challenged. Finally the rising need for care-giving for both elders and children will make full-time jobs a smaller and smaller share of how work gets done.
c. Everybody will need to re-skill and up-skill on a constant basis: A world with five types of employees ( Full-time, Contract, Free-lance, Fractionalized and Agentic) , plus talent spread across locations and AI increasingly handling significant work will require new leadership skills and training of different expertise. We have entered an age of “Debossification” where managing, checking in, allocating and monitoring will be seen to be of little value. This combined with the decline of the value of knowledge will require a transformation of the work force.
To learn more and hear from dozens of talented people pioneering the future of work consider reading Pioneering the Future of Workwhich also lays out the key four themes driving the future of work and listen toThe Rethinking Work Showto hear from pioneers and Unbossing.where Reed Hastings of Netflix and others speak of new approaches to modern leadership.
2) Plan for the long term. Even if we are 50 we have 15 to 20 years of work ahead of us.
a. Aging is a “prejudice against our future selves”. Avoiding thinking about or thinking negatively about aging or our future selves. It is a form of self-discrimination.
b. Many of us will “fail” retirement. A lot of retirement planning is about making sure one has the financial means to retire and how to remain healthy, but that is not enough. Most people who can stop working soon find themselves without purpose or meaning or even identity since work is so central to identity, community, purpose and growth. The question of “Why am I waking up in the morning?” is rarely answered day after day after day with “To play golf” or “To travel”. If income was all that mattered why are all the tech bros in Silicon Valley with their billions continuing to work given their belief that universal basic income will be all we need when AI impacts our job?
c. AI, Time and the rapidly declining half-life of Knowledge: Just as careers are getting longer, the half-life of knowledge is declining faster and faster. Even if we are 30 our skills may lead to a forced retirement at 35 or 40 unless we upgrade and reinvent our skills.
Seth Green, Dean of the University of Chicago Graham School of Continuing Education distills decades of insights and learning in a conversation where he also shares many free resources at the University available to everyone globally to keep learning and growing.
Take a read and a listen to What Next? 50 Year Careers.
Photo: “Dawn’s Whispers: Graceful Hoopoe Silhouette at Sunrise” by Hermis Valiyandiyil
3) Recognize that the 50 years involve very different seasons: Careers have at least 3 seasons and to each season there is a particular approach and focus.
One of the three most popular posts of all time is Career Lessons Revisitedwhich distills my observations and learning over a 45 year career including:
The importance of finding the least sucky job possible at the start of of one’s career. Or these days why we may want to look for work first and then a job next.
The key to the middle years is that we build skills, relationships and reputation that belong to us and not just the company we work for. Too many people conflate the budgets they control and the Brand name of the company they work for with their own popularity. Another key in middle years is to focus on who we work for more than the company we work at. People build people. Companies do not.
Three decades into a career one still has two decades ahead and now is the time to learn, unlearn and relearn versus believing retirement, even if affordable, is approaching. It is also an era to practice letting go since every career has a midnight hour and the smart people leave at five to twelve.
Graphic: The Nine Word Exercise by Rishad Tobaccowala.
4) Architect, hone and sculpt our reputation.
In order to maximize optionality we need to position ourselves and then build a reputation via credibility and a body of work.
In Career Architecting I share a nine word exercise that helps define our niche, our voice and our story.
It then takes our positioning and illustrates how to link it to market needs and develop the credibility and platforms to build a reputation.
This works for any age group, any industry and any country.
Photo by Rishad Tobaccowala
5) Keep a job for a long time in a firm by thinking like a Company of One.
The best way to keep a job or work you like for a long time ( even decades) in a firm of any size is to learn how to operate like a Company of One. A Company of One is not about I, me or mine but about:
a) Be known for expertise in specific skills, have a reputation for being collaborative and being a person of integrity.
b) Continuously keeping one’s skills up to tomorrow and not just up to date.
c) Maximizing optionality in many ways as possible.
When one has skills, reputation and choice one will always be in demand not just in the marketplace but at one’s current place of work.
The Company of One series are six posts filled with actionable exercises that will set anyone doing them free from anxiety.
One Single Thing.
Ben Thompson is one of the best strategic thinkers about technology and its impact on firms, societies and more. Almost everybody in technology, including the CEO’s of major firms reads him. He has an ability to clarify, illuminate, extrapolate and ruminate in ways that will leaves readers and listeners ( his writings are also available as a podcast) enlightened.
Here is a piece entitled Tim Cook’s impeccable timing which is a must read because through the lens of a retirement announcement, Ben takes us on a strategic romp across great horizons! It is free to read.
https://stratechery.com/2026/tim-cooks-impeccable-timing/
Three Keys To Engagement.
Gallup just released its 2026 Global Employee Engagement Survey which indicates that globally only 20% of employees are engaged at work. In the US the number is 31%.
Best practice organizations however have 70 percent employee engagement.
Managers who are supposed to motivate teams have suffered the greatest decline in engagement.
There are many reasons ascribed for the low engagement from a) too much work spread across too few people b) a forced return to the office placing pressure on juggling myriad personal and professional responsibilities c) the speed of change and d) the threat of AI to jobs.
When people are engaged they feel challenged by the work, connected to each other, aligned with the purpose of their company and see a path way to growth.
Another critical factor is to have a manager or leader who is highly capable and who treats them with respect and understanding.
In the end disengagement has a lot to do with the person one is reporting to more than anything else. A feeling that one is not heard or seen. A belief that one is treated as replaceable cog in the wheel.
The solution is not bringing in a bevy of consultants or training but upping three human traits that any of us can do at any time without permission or budgets.
We can enhance engagement with our own teams with :
1) Curiosity
2) Empathy
3) Generosity
Curiosity
One simple way to get people engaged is to ask about them and by doing so, also get them curious about others.
If someone asks you questions about yourself that are not tricky or puts you in a vulnerable place, it is very likely that you will be engaged.
One simple question that few people ask but significantly boosts the ability to connect is this one:
What three decisions or events have made or shaped who you are? (These really two different questions depending on whether you chose events or decisions)
This makes the person who you are asking the question to have to think a bit and in that way is difficult.
However, there is no right or wrong answer and everyone can come up with an answer, so no one is on the spot.
Their answer helps build a conversation because the person who is asked the question may then ask the questioner for their answer to the same question.
Try it on yourself and people you wish to engage with.
Empathy
Today a mixture of polarization, generational differences, work pressure and speed give us very little time to figure out what we are doing, let alone getting to see people from their perspectives and understand where they are coming from.
To engage one needs to be empathetic.
Asking others about the events and decisions that made them, which is being curious about them, is one way to generate empathy.
In addition, a simple question can let you be more empathetic.
How can I be of help to you?
A very simple question that few people ask.
People find it hard to ask for help (though we all should) but we should find it easier to ask people how we could help them.
This question can be refined in many ways to better telegraph understanding of a situation or elicit a particular type of answer.
For instance.
How can I help you more to manage X (X might be a client, an employee, a situation) which signals you understand the situation and ensure that you can provide the help.
How can I do things differently in the way I work or manage to help you become more effective? This signals empathy by understanding that sometimes helping someone is not changing what they do but what you do.
Generosity
Whenever you give someone a non-monetary gift of time, kindness, help, or a monetary reward of a special bonus or one time award which is unexpected and goes above and beyond they will be deeply engaged.
Give first.
Give more than you get.
Give without strings.
And you will find that you will get attention, time and much more at a multiple of what you give.
In a world of transactions and negotiations try not being transactional or a negotiator.
Today people get taken aback when people help people with no strings attached.
When one is generous there are two amazing rewards:
First one earns goodwill which lasts a long time.
Second one feels good about oneself.
Generosity is a great strategy.
Curiosity. Empathy. Generosity.
Always works. And will work really well in an AI Age.
One Single Thing.
Beginning last week, I plan to end every post linking to one single thing to listen, watch or read that might make you see, think or feel differently.
Last week I shared a short video called Retirement Plan.
This week is a recent post by Om Malik.
Om is a San Francisco-based writer, photographer, and investor who has spent three decades in the trenches of Silicon Valley as a journalist, entrepreneur, and, more recently, as a venture capitalist. Om has been writing about the commercial Internet since its birth.
Om has an incredible free blog from where I share a post called Velocity is the New Authority. It begins like this…
“Why does everyone feel overwhelmed by information? Why does it feel impossible to trust what passes through our streams? We tend to blame individual publications, specific platforms, or bad actors. The real answer has less to do with any single media entity and more with structural changes in the information ecosystem.”
Take five minutes to read it and it will give you a new perspective on why and how we consume content: Velocity is the New Authority.