Career Fitness: 3 Critical Exercises.
All Images via MidJourney
In these tectonic times, our career planning may need to build new muscles so we can remain relevant.
Here are three critical exercises to upgrade our mental operating systems:
1. Prepare for a very long marathon and not a sprint.
Most of us will work for five decades from our early twenties to our late sixties or early seventies.
We need to plan and plot for fifty year careers where over the decades we may pursue completely different vocations.
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. Continuous learning will be the only path to constant earning.
We should not price ourselves out of our dreams: Too many people find themselves doing a job they do not truly enjoy or love, much longer than they need to because the job creates the ability to fund a certain lifestyle. One’s lifestyle is rarely the dream that nourishes or fulfills. The way we spend our time is the way we live our lives and work is central not just to income, but also to identity, community, purpose and growth. Funding the lifestyle often prices us out of the careers and vocations that truly resonate with us, but we now cannot afford to pursue.
Aging is a “prejudice against our future selves”. Avoiding thinking about or thinking negatively about aging . Ageism is a form of self-discrimination since we will all age. We are never too old to reinvent ourselves, build fresh skills and pursue new dreams.
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”.
2. “Jobs” ≠ “Work” . Get fit for periods where we have work but not a full-time job.
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:
We are at peak full-time jobs but not peak work or wealth creation opportunities.
The faster we delink work and jobs in our minds and the way companies are run the better off we will be.
Too many leaders fixate around jobs, classical organization design and place as critical when a new generation of companies focus on work to be done to deliver outcomes with different types of talent ( full time, freelance, fractional, contract and agentic) wherever they are to maximize agility and minimize costs. The age of conducting talent with a baton is cool for a classical age but is useless in a jazz age of improvisation.
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. Capital invests in “tireless” agents vs “tiresome” people.
While work opportunities can keep 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. Recently McKinsey reduced head count by 5,000 people while adding 12,000 agents.
3. Sculpting a “Company of One” mindset is critical to keep a career fit.
Whether it is finding work post-retirement, working a side-hustle or passion project to make ends meet or build an expertise or create an off-ramp, or filling the gaps between full-time employment at firms which are often trigger-happy in adding and removing talent from their payrolls, the smart professional prepares to be a company of one.
But even if you do not fit any of these categories be aware that companies are creating internal marketplaces where opportunities can be identified and applied for and teams of experts can form and dissolve around projects.
As a result, for an individual to thrive in a company they will need to learn how to operate as a company of one. The combined power of the Avengers is because each of the Avengers is powerful on their own and not just because they learn to work as one.
Think of yourself as a better paid Uber driver with benefits if you work for a company.
If your expertise is needed at that time or in a particular market and location, and your collaboration and ability to work in teams is highly rated you will be in demand.
If not, as companies manage and monitor costs and increasingly find ways to plug into resources all the time everywhere you will find yourself parked permanently.
Or consider the Hollywood model where expertise come together on tv or movie projects and then the people disband and move on. Very few people work at a studio. Most people work in teams where they bring their skill whether it be casting, directing, catering or make up etc. The future of business will be similar as companies begin re-aggregating expertise around projects versus having hordes of generalists or people hanging around for a project. McKinsey and Bain have done this for years.
Nor everyone will be a freelancer going from gig to gig but if we build our career with the mindset of continually honing expertise, working well with other people in teams and being flexible, we will succeed in our company of tens of thousands versus thinking of ourselves as a cog in big machine waiting for someone to care for or build our career.
Think of our main as job as venture capital to fund the side gig or the next job.
We must plan for a very long career where work will involve both full time jobs and many other types of gigs and through it all we need to keep upgrading skills, reputation and collaborative skills by thinking of ourselves as a Company of One and never delegating our future to anyone else.
This allows us to be true to the only mantras worth following:
Keep skills up to tomorrow not just up to date .
Maximize Optionality.
All Images via MidJourney
On Education.
The Power of Education.
Three of the most powerful forces in the world are a) gravity b) compound interest and c) the bond between a mother and a child.
They have always existed driven by the power of science, math and nature.
An even more powerful force than these is education.
Education lifts us up while gravity holds us down.
Education compounds even more than compound interest in that it increases not just returns to money but returns to living.
Education is seen as crucial by mothers and fathers who invest and sacrifice for it.
Education has never been more important.
Today in a world of change it is critical to upgrade our mental and emotional operating systems.
Transformation of lives and companies happen when talent transforms and the only way to do so is through education.
Education can be academic and in institutions and classrooms but a lot of education comes from the school of life, risk taking and experience.
While credentials may be important, education is less about degrees and more about learning new skills. It is about the building of new insights by connecting dots in new ways. The growth that comes from reflecting and building on failure and mistakes. The layers of experience that transform a body of knowledge into craft and expertise.
Education has never been easier.
While certain schools in countries continue to be highly expensive and deeply selective (often for no other reason than to constrain supply to allow graduates to earn high incomes) they are forgetting that education is about abundance versus scarcity. This mindset and way of teaching has now begun a rapid decline.
Today, a new world order and range of learning is increasingly available and will soon completely disrupt the old ways. Low cost resources from online courses, YouTube, AI tools and a series of credential courses from guilds and companies are making learning, training and skill development easier and easier. These skill sets can be monetized in a range of ways that does not require having credentials to get a job. World class tools including compute are available in the cloud on a just in time basis, AI agents to staff teams, and global marketplaces to access talent and inputs and sell services and products are a click away on the mobile device 24 hours a day.
The key is not to think of education as a signal to get us into a place but a way of building life long skills and learning that enables us to find meaningful, purposeful and rewarding work.
Education has never been more challenged.
Most professional education establishments are imparting irrelevant skills, concentrated in the first 25 years of life, using out of date approaches, for a job market that no longer exists.
Education in the traditional way is being deeply disrupted and the people in charge of learning are now going to have to go about unlearning their pedagogy!
The new educators will be a combination of reinvented outfits and self-educators, who enable and access new skills, across fifty year working careers, leveraging the latest methods and technologies , with a recognition that the majority of us will find meaningful purposeful work outside of jobs in a company.
The disparity between what is needed and where the future is going is a wide chasm.
How to self-educate.
Education is also not just about constant life-long learning but also unlearning.
The future does not fit in the mindsets of the past.
Five keys to self-educate when one has highly limited budgets and little to no time:
1. Set an hour a day to learn. This builds cognition which is the ability to think.
2. Build a case once in a while for the opposite of what you believe is true. This enables curiosity which is about asking what if? And why not?
3. Pay attention to what gives you flow and fit. This allows one to be creative which is best described as an expression of oneself.
4. Start with AI tools not search. Converse with other humans and machines. This will build skills of the choreographer allowing us to connect alien (eg. agentic AI ) and human life forms to drive outcomes.
5. Practice story telling in a multitude of forms from oral to visual to verbal. This will help us be communicators who can convince and move people.
Architecting, building, honing skills of cognition, creativity, curiosity, choreography and communication is the key to our future.
And educating ourselves in these is the best way to find purpose, meaning and rewards.
All images via prompts to MidJourney
Rethinking …
The most popular edition of the 268 posts of this Substack so far is Rethinking Presentations on how to put together powerful presentations with only 9 slides!
The third most popular post is A Company of One on a way to ensure one remains relevant in a world of changing work.
This post combines a second approach to rethinking presentations and then illustrates how the format is used to get people to start rethinking work.
Rethinking Presentations 2
Rethinking Presentations 1 showed how to put together a presentation to make a sale or get an order and remains a very impactful way to do so.
Over the past few years as I have worked for myself rather than a company. I spend less time selling and more time advising, explaining the tectonic shifts we are experiencing and trying to inspire new behavior. Here is a very simple approach anyone can use when one is trying to educate, explain or inspire change.
The three key outcomes this new format seeks to deliver are:
a) Accessible explanations that are simple, focused and identify all the key issues. People are overwhelmed.
b) Actionable inspiration that leaves people not just feeling inspired but armed with a way to take action right away.
c) Personalized relevance in that every single person finds relevance to their personal situation. It must resonate to help them solve a problem or take advantage of an opportunity.
This approach also requires only 9 key slides:
Slide 1: Title Slide (Action oriented)
Slide 2: Agenda (A simple, impactful way to telegraph what is to follow)
Slide 3: Shifts (What are the forces driving the changing situation and future)
Slide 4: Implications (What are the implications of these key shifts on the audience)
Slide 5: Realities (The hard truths and key challenges we need to face)
Slide 6: Approaches (What steps should one take right now)
Slide 7: Mindset (How to frame and address the situation moving forward)
Slide 8: Questions (Interaction and Q&A key when trying to explain/inspire)
Slide 9: Resources (Ways people can learn more and upgrade themselves)
Rethinking Work
The Rethinking Work presentation below uses this 9 slide approach to explain to management why work will change more this decade than the previous 50 years and what leaders and companies need to understand and address right now.
But this same approach can be used by anybody who wants to educate, explain and inspire on any subject or topic. It is totally modular. Just change topic and put in the relevant shifts, implications, realities, exercises and mindsets!
Five interconnected shifts will change work more this decade than the past 50 years.
Demographics of declining & aging population. Different mindsets across generations.
Technology (AI, Blockchain & Media Landscape where everyone is a media company).
Marketplaces that allow individuals and companies to access talent and opportunities.
More people will work part time or free-lance than full-time in the USA starting 2026.
Covid did not just change where we work but why we work and who we work for.
Four implications that organizations and leaders must address.
More and more work will be done without filling jobs. Until 200 years ago there was lots of work and few jobs. We are now going to have more and more work and income/wealth opportunities than ever but fewer jobs. We are past peak jobs.
Full-time, freelance & contract employees will be joined by fractionalized employees and agentic workers.
Current structures of most companies are often built around jobs rather than how to get work done by attracting and retaining the best talent with the greatest agility and affordability.
Debossification is the only way forward where leaders focus on zones of influence vs zones of control. Where leaders spend the majority of their time selling, building, inspiring, servicing and mentoring vs. monitoring, measuring, processing, and checking in, all of which will be done better by AI.
Three realities every company must face.
Companies do not transform people do. Change never happens without a talent plan.
Talent/L&D more critical than ever but must reinvent themselves and be less fearful.
Leadership is the critical element more than technology or strategy or partnerships.
Two Exercises.
Most management is world class but often self oppress and limit themselves by imagining constraints that only exist in their minds. These two exercises suggest starting with a fresh sheet on both the organizational and talent front.
Why is the current organizational structure which was probably out of date pre-Covid, pre-AI, pre-distributed work, still relevant for the tectonic changes coming? Without the right spinal architecture it makes no difference what AI or other organs are added.
The only thing a company has is talent. If the game changes and the playing field changes, talent needs to be rethought via a combination of upgrading skills, new ways of working and accessing of enhanced expertise both inside and outside the firm.
One Mindset.
We are all migrating to a new country, a new world, an unknown zone called the future which will not look like the place we are today.
So why have an immigrant mindset?
We need to think like outsiders since the new risks and opportunities will come from outside our existing competitive set.
We need to think like underdogs since AI is the slingshot that allows David to bring down Goliath. Moats might be used as sources of water to flood our castle!
We need to take the hard painful decisions and make the sacrifices now so we and our company can thrive in the future.
Questions and Resources to Keep Learning.
Education, Learning and Reinventing are constant.
Here are three completely free resources to upgrade one’s mental operating system:
This Substack (The Future Does Not Fit in the Containers of the Past)
A weekly podcast (What Next?) where every week people who are forging the future share their best insights, provocations, perspectives and points of view.
And The Rethinking Work Show a show on YouTube but also on Spotify and Apple where every week a discussion with people reinventing work from CEO’s and architects wrestling with back to the office, technologists introducing agentic employees into the work place, academics with data that put a lie to so much fuzzy thinking about the future of work, pioneers designing new firms which are AI first, different generations speaking about companies and work and much more…
You can download the extended (18 slide version of this presentation which goes deeper into the 5 shifts and the 4 implications) here by clicking on the presentation and you may use it in anyway you want.
Also at Rethinking Work check out the resources section where there is career advice and lots of stuff to help every one become better and more effective. If you or someone you know is rethinking your career these four articles might completely change the way you plan the rest of your working life.
On Leadership and Culture.
Companies and organizations that thrive excel in two areas:
Leadership and Culture.
They are both key and closely intertwined.
A. Leadership.
Leadership can be distilled down to this:
Leaders acknowledge, face and communicate reality.
People follow people and not titles since titles are bestowed while leadership is earned.
The six characteristics of great leaders are capability, integrity, empathy, vulnerability, courage and inspiration.
Reality.
A key to leadership is to solve challenges and address problems. This requires confronting issues versus looking away or hoping some form of magical thinking will make them go away.
People will follow a person if they suspect they are not addressing real issues and challenges however difficult they may be.
Followership.
Without the hearts and minds of the team one is not a leader but a ruler.
Rulers leverage fear, project power and exploit insecurity.
Employees genuflect, fall in line, salute and pander to the hollow and bloated boss, while they silently seethe, plot insurrection or practice defection.
Six Characteristics.
a) Capability: To be a leader one must be capable in one’s field of work or craft and to keep improving and honing one’s skill with a dedication to a growth mindset. Doctors will not listen to doctors who are not great at medicine. A creative will not respect someone whose body of work they do not admire.
b) Integrity: Can one be trusted? Does what one says, what one does and how one behaves aligned and also resonate with the rules of science and economics ?
c) Empathy: Leaders can see from other points of view and they understand that employees are people and work is a very important part but all of their being. They understand and they listen. They care. They do this both for employees and for customers.
d) Vulnerability: Great leaders acknowledge mistakes. They know they do not have all the answers. This means they are open to criticism and correction and they surround themselves with skills sets that offset and balance their areas of weakness.
e) Inspiration: How do leaders face and acknowledge reality and hard truth but still get people to unite, align and take the challenges head on? They do so by recognizing that people choose with their hearts and not their minds. They inspire through a combination of personal example and storytelling.
f) Courage: The courage to make the hard decisions. The courage to take calculated risks. To understand that sticking to principles often comes with a price.
B. Culture
It has been said that “culture eats strategy for breakfast’ and often when companies decay ( Sears) or resurrect (Microsoft) or have distinctly different outcomes in the same industry (Delta vs American) a key determinant is the culture. What it is like, how it is improving or how it is getting worse.
Next Wednesday on The Rethinking Work Show we will hear from Alastair Creamer and Doug Milliken who co-founded Creamer and Milliken which help some of the best companies in the world on cultural change.
Once I read that the culture of an organization is revealed in how people behave when no one is looking or monitoring their behavior.
It is not just heard or seen but felt as my guests so eloquently stated.
Culture is about people. Yes, it requires leaders to set, correct and support the culture but it is how they treat people and how people feel about themselves, their company and their colleagues that is the fabric of culture.
Companies with great cultures tend to have talent who feel most of the following about their jobs and companies:
Excellence: One cannot have a great culture without excellent financial results, products/services and superior talent. People. Product. Profit. At least two of these need to be firing on all cylinders most times. Companies sometimes reduce the emphasis on one to invest in one of the other areas such as reducing profit to invest in new products.
Good Compensation and Aligned Incentives: If people are not paid adequately or fairly it really hard to attract and retain the best people to have a good culture. Companies do not need to have the highest compensation but they need to ensure the gap between them and their competitors is managed. But it is not just individual compensation but ensuring that incentives are aligned with the behavior that is expected. If team work is key there should be a greater focus on rewarding team results versus individual results ( though both are important)
Recognition : Great cultures recognize contributors and key players ( “difference makers”). They ensure people are heard.
Autonomy: People are trusted to deliver with limited monitoring and can access resources to do so. Freedom within a framework versus rule books and overly regimented “play books”.
Purpose: Talent believes in the purpose and values of the company and see the role of their company beyond that of just profit but ensuring their customers thrive and giving back to society or community.
Growth: The company is growing, has a plan for growth or even if static, the individual is growing and teams are growing by being given opportunities to learn and build new skills.
Connectedness: People feel connected to each other and to their leadership. They feel free to speak up and share and even joke. They express themselves without fear.
Solving for and focusing on these seven drivers of culture is one way smart leaders are working to ensure that in a distributed world with different types of employees including AI agents the fabric of culture is not torn.
They and their talent/people leaders will all have different approaches to get there but they all recognize it is key to ensure that each of these seven seeds of culture are watered.
Leadership and Culture and not technology or strategy or size that are they keys.
Photos by Roger Fishman.
Fear…
Image by Midjourney to the prompt "fear"
If there is one emotion that is increasingly widespread across the world it is that of fear.
It is particularly acute in the world of business at every level and in every industry.
Fear beats like a second heart beneath an outward veneer of confidence.
What we fear at work is multi-faceted and multi-modal. Here are just a few factors:
a) Will our jobs be automated away by AI ? A very senior person who I respect in the world of tech wondered if the new tech they are creating is the wood chipper that they will be fed into? Are they architecting their own obsolescence? In other industries all of us wonder if AI will create a hunger games environment inside each company as they launch efficiency drives forcing us to compete for fewer and fewer opportunities.
b) Are we still relevant as leaders? As younger generations look with great dubiousness at their seniors, wondering what they do and the price they paid to get their roles, the senior folks also are grappling with change coming so fast that they no longer have the option to wait it out. With many financial obligations, the increasing insecurity of of one’s job and need to reinvent oneself make us fearful.
c) Where are the opportunities to grow? The great flattening is removing many middle management opportunities and roles while a combination of AI and uncertainty is making companies delay hiring even if they are growing. Companies worry both about business softness but also suddenly finding themselves with too many people if the new technology truly increases productivity.
d) Can we say anything that does not get us into trouble? Despite all the statements about fearless environments, risk-taking, the freedom and growth that comes from the clash of ideas, and the emphasis on experimentation happy talk, there is a dark cloud lurking. One of sinister monitoring and pressure to align, conform, and comply that invisibly defangs attitude , depersonalizes individuality , devalues provocation and dismisses those who walk another path.
e) Do we have a pretend job? Alex McCann who I will have as guest on The Rethinking Work show next week has an amazing series called “The Death of the Corporate Job” that begins like this:
Last week, I had coffee with someone who works at a big consulting firm. She spent twenty minutes explaining her role to me. Not because it was complex, but because she was trying to convince herself it existed. "I facilitate stakeholder alignment across cross-functional workstreams," she said. Then laughed. "I genuinely don't know what that means anymore."
She's not alone. I keep meeting people who describe their jobs using words they'd never use in normal conversation. They attend meetings about meetings. They create PowerPoints that no one reads, which get shared in emails no one opens, which generate tasks that don't need doing.
The strangest part: everyone knows. When you get people alone, after work, maybe after they've had time to decompress, they'll admit it. Their job is basically elaborate performance art. They're professional email forwards. They're human middleware between systems that could probably talk directly to each other.
f) We fear the death of leadership: So many “leaders” seem to have weather vane minds and squishy spines that are quick to align. Fleshy things who have a tropism that bends towards money and power. They tremble like leaves shivering with fear, rootless without any principles, but put on the show of florid orchids.
Fear leads many of us to go through the motions. We need the job. So we repeat the new mantra. Espouse the updated values. Chant the company slogan. We go along and get along. Hail the new leader! Hail the visionary Board! Hail the re-organization! Hail yet another re-organization!
Some keep their heads low and save all their passions for the side job. Others filled with hot air conflate title and the power that comes with the title as ones own power though deep down they know differently.
Overcoming Fear
We should not give into fear.
Because when we do, we lose everything including our ability to think for ourselves.
Frank Herbert wrote in Dune: "Fear is the mind-killer."
And when we are ruled by fear we are defeating ourselves.
We are practicing self-oppression.
Ralph Waldo Emerson wrote : “Fear defeats more people than any other one thing in the world."
Fear is natural but it is also the fuel that often can ignite courage.
"Fear is a reaction. Courage is a decision." — Unknown
"Courage is not the absence of fear, but the triumph over it." — Nelson Mandela
If we are fearful of someone we should know this:
The fearsome are often fear filled: An outward shows of great confidence is often co-related with deep anxiety. The folks who are the most arrogant, the most sure of themselves, the least approachable are usually the most insecure. Other wise why all the drama?
First comes confidence. Then comes humility.
Many of the really accomplished people are gracious, generous, and kind. They know they are good. And that is enough.
And so the first way of overcoming fear of others is by recognizing that usually the ones who fill one with fear are usually fretful themselves.
Do not fear them. Instead take pity. Do not tremble. Put out a hand in friendship. They are not bad people but just isolated and worried with many challenges and difficulties of their own.
Stay true to an internal compass: The thing to fear is not others but when one we let ourselves down. When we lose our internal sense of bearing and the trueness of things. The point about principles is often one has to pay a price to stay true to them.
If we are fearful of being replaced or becoming obsolete we should do this:
Upgrade our skills: It is easier than it looks and often does not take much money. Today there is a world of online and offline capabilities ( including people in our organization willing to help us). All we need to do is to allocate an hour a day to learn new things. Very soon we will realize that the new technologies are not that difficult. When we invest $60 to get the paid version of Open AI, Gemini and Claude we have better AI than the company we work for will ever have since they sandbox the most recent version and tend to scale on just one foundational model.
Maximize our Optionality: When we lack choice we feel cornered. Everyone should put a plan of action to enable options right away even if it takes a year or two or three to manifest itself. Build a reputation. Launch a side hustle. Feed a network. Reduce spend. Save a little nest egg. The more options we have the less we can be controlled by anyone or any firm and the less we are fearful. Too many people start looking for the next opportunity when the current gig becomes untenable. Do it now. Sooner or later, through choice or circumstances we all need to leave. Every career has a midnight hour and the smart people leave at five to twelve. The more options one has the longer one can stay in a difficult role and the less likely we will fear other people.
Fear is natural. It is a signal that we are alive. But it is also the catalyst to courage, the driver of decisions, the igniter of revolutions.
We have nothing to lose but our fear.
Soul. Human. My first book is even more relevant today as recent circumstances have people recognize we truly need to restore the soul of business and remain human in an age of AI…learn more here…https://rishadtobaccowala.com/restoring-the-soul-of-business
