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