The Career Revolution, Part IV

The Invisible Workload of Modern Careers

Beyond headlines about remote work, AI disruptions, and the gig economy, there's a more profound change: the decline of traditional career paths. The modern workforce is undergoing a gradual transformation that began in the 1960s. Old career routes, once led by HR, annual reviews, and clear promotions, are now fragmented, nonlinear, and often hidden. Workers must manage complexity, demonstrate their value, and adapt quickly, all while coping with the emotional toll of uncertainty.

Freelancers, founders, and entrepreneurs have always faced this, but now the shift is more widespread. Employees, consultants, creatives, and specialists are being asked to think differently, like strategists, storytellers, and systems designers. The responsibility for demonstrating impact, growth, and relevance has clearly moved from organizations to individuals.

I’m deep into the details of writing my next book, Get Beyond the Grind: Work journaling with The Grind Diary. This led me—well, “pushed” is a better word—to take a long look back to better understand how we got to this point, a place where everyone in the workforce must navigate the Marketplace on their own. This wasn’t always the case. I wanted to try to put things into perspective.

These are unsettling and challenging times where success depends on building a personal career infrastructure that includes a flexible mindset, a forward-looking perspective, and the best tools and hacks to stay competitive in an ever-changing work landscape. It’s about being a vigilant, thoughtful, independent Free Agent out of necessity. We’ve arrived here gradually over the last 70 or so years, but in this millennium, there have been unique shocks and jolts, adding an edge to the ongoing change.

A Confluence of Forces

Four major economic and social crises of the 21st century served as compounded catalysts, each one amplifying the next and accelerating the move toward greater individual agency in the American workforce. Collectively, they reshaped the labor market through economic shocks, psychological shifts, and technological advances.

It all began with the Dot-com Crash. That downturn pushed many highly skilled professionals into the open market, revealing the false sense of security in corporations—even in fast-growing sectors. It established a new standard: specialized talent could no longer depend only on traditional employment models.

Then came 9/11, a psychological shock that undermined workplaces and shattered the sense of safety inside the office. In response, companies adopted more transactional, risk-averse policies, such as conducting background checks, developing disaster recovery plans, and moving away from loyalty-based cultures. Workers absorbed the message: trust less, rely on yourself more.

The Great Recession intensified these trends nationwide. As mass layoffs forced millions out of work, the labor market was flooded with skilled workers seeking new opportunities. Meanwhile, companies increasingly depended on temporary and freelance workers to stay nimble and cut costs. This two-sided pressure, workers being pushed out while businesses hire flexible talent, has caused a lasting shift. Non-employer companies expanded faster than traditional firms during this time, indicating that gig work is no longer just a trend but a new economic reality.

COVID-19 served as the ultimate proof of concept. It demonstrated that productivity isn’t dependent on physical offices. Remote work became necessary, something many found they preferred. This led to a prioritization of autonomy, and the Great Resignation of 2021-22, which coincided with the frenzied post-COVID-19 startup investing and a reality check in 2022 when it all came to a screeching halt.

Then, on November 30, 2022, OpenAI debuted ChatGPT, and we are all still reeling.

Each crisis, along with recent developments in AI, has further undermined the traditional model and bolstered the free agent alternative. What started as disruptions has turned into a self-perpetuating series of mini-cycles, driven by technology and changing social values.

The Underlying Enablers

Technology has been the constant driver. From the rise of the internet in the late ’90s to the explosion of smartphones, online marketplaces, cloud platforms, and AI tools, the infrastructure for independent work has become seamless. Job matching, project management, invoicing, and payments are now efficient and scalable.

At the same time, generational values have shifted. Millennials and Gen Z entered the workforce during a period of instability. They are tech-savvy, want independence, and are skeptical of traditional systems. They prioritize flexibility, ongoing learning, and purpose. Having seen the breakdown of the conventional agreement, they are cautious yet open to alternative paths, which they may need to pursue.

The Free Agent Outlook

Freelancing is now a vital part of the economy and is no longer seen as just a niche. This year, over 76.4 million Americans will identify as freelancers, accounting for 38% of the workforce. That’s a 4 million increase since 2022, with forecasts suggesting it will surpass 50% by 2027. This group contributes roughly $1.27 trillion to the U.S. economy and is becoming an increasingly important part of the GDP.

The shift toward greater free agency will likely continue. It is not impossible to imagine contingent workers becoming THE workforce of the future supported by AI and automation. These technologies will enable both workers and organizations to operate efficiently within decentralized and flexible systems. Furthermore, I expect generational momentum to propel and hopefully enhance the trend. Younger workers, affected by disruption, are comfortable with flexible arrangements and actively seek work-life balance. The free agent model offers both.

Success in this landscape requires an entrepreneurial mindset. Freelancers must take matters into their own hands—developing in-demand skills, managing finances, and cultivating overall business savvy. Being “agented” means doing the work and also managing one’s own supporting systems. Those who develop a mindset of creative persistence and strategic ownership will succeed in a world where careers are created, rather than in years past, where they were maintained.

The Shift Continues Toward Radical Responsibility

This steady drift to ever greater degrees of free agency amounts to a fundamental change that’s now baked into the cake of how work is structured. While flexibility, autonomy, and decentralization bring new freedoms, they also create new challenges. The imperative for maintaining a career, developing skills, and strategic planning now falls squarely on each individual.

Change of this magnitude affects everyone, not just those who have always been at the forefront. Now, full-time workers, managers, and specialists across various industries must consider what it means to take charge of their journey, finding ways to demonstrate their worth while remaining flexible and open to new ways to square the circle.

This is where personal infrastructure tools and methods come into the picture. Free agency will remain with us, and it will morph. Workers of all types will need systems that help them track progress, measure impact, and leverage their experience into a competitive advantage. From career coaching and financial planning to documentation and self-assessment, the future of work will be shaped by those who build their own support systems.

In the best-case scenario, someone will see themselves as a self-managed, independent Free Agent. They will have a collection of personal infrastructure tools ready to deploy, although rarely used, as they advance within an organization or industry, similar to those in previous generations. This still occurs, but less frequently.

Therefore, my message is clear for everyone in the workforce, especially younger workers: do not expect the best-case scenario; instead, focus on making best-case preparations.

I see the need, and my upcoming book and app, Get Beyond the Grind: Work Journaling with The Grind Diary, are designed to meet it - a tool to help workers and professionals document their journeys, clarify their value, and gain strategic momentum. Quite honestly, I see it as part of a larger movement: one where individuals take radical responsibility for their careers, supported by a variety of similar tools and frameworks that turn effort into evidence and experience into advantage.

In a world where no institution tracks your growth, those who thrive will be those who do.

Please share this post, follow, and subscribe.

And, stay tuned for my post next week.

Onward.

The Career Revolution, Part III

When the Rules Changed Forever (1980–1999)

In 1982, AT&T employed over a million people. By 1995, that number had been halved. The message was clear: permanence was an illusion, and the rules of work had quietly and irreversibly shifted.

This wasn’t just a single disruption. It was a slow breakdown of the postwar social contract. The workplace stopped being a fixed destination and became a proving ground. Institutions that once provided stability through pensions, mentorship, and internal mobility began to fade away. Meanwhile, the average worker, once supported by structure, was left to navigate a new landscape—one that required strategy, adaptability, and self-reliance.

For many, this era is remembered not by headlines but by moments: the first time a colleague was laid off unexpectedly. The day a manager said, “You’re lucky to have a job.” The shift from “career ladder” to “career jungle gym.” These subtle, personal, cumulative memories marked the start of a new reality.

The Perfect Storm

The unraveling started with energy shocks. The oil crises of 1973 and 1979 ended the postwar boom and revealed the fragility of growth models based on cheap energy and domestic dominance. Japanese automakers and electronics companies began outperforming established US enterprises. Toyota, Sony, and Panasonic redefined quality and efficiency, forcing American companies to reassess their approach.

The first shock directly touched me. I was laid off, along with all other untenured teachers, in a small school district in southern Minnesota. Overnight, fuel oil costs skyrocketed (a significant consideration given Minnesota winters), and budgets had to be adjusted accordingly. It was back to the drawing board and free agency, although my perspective on this had yet to develop fully.

Wall Street, too, shifted its focus. Quarterly earnings became the new standard, replacing long-term stability with short-term results. The S&L crisis and the 1991–92 recession gave corporate leaders cover to break implicit contracts. Lifetime employment, pensions, and loyalty were quietly abandoned.

Globalization, driven by policy changes and deregulation, opened new international markets, accompanied by a rapid wave of technological advances, which increased pressure on industries. Manufacturing shifted overseas, and the Rust Belt experienced a steady decline. Eastern Airlines went bankrupt. Pan Am disappeared. Steel towns shrank, while the Sun Belt expanded with hope and uncertainty. The phrase “job security” became nostalgic.

Technology as Job Killer

Personal computers arrived as productivity tools in the mid-80s and quietly became silent enforcers. Spreadsheets, macros, and early internal messaging replaced secretaries, clerks, and middle managers. Internet use grew steadily despite lagging connectivity, allowing information to flow laterally, undermining gatekeepers, and flattening organizational charts.

In manufacturing, advanced automation gradually gained momentum. By the late 1980s and into the 1990s, robotics had made significant advancements. What started as simple, pre-programmed movements developed into machines capable of performing complex, multi-step tasks with higher accuracy. This shift was driven by increased computing power, more intelligent sensors, and more responsive control systems, marking a crucial turning point.

Automation moved beyond the factory floor, reshaping consumer electronics, assembly lines, and everyday products. The computing revolution improved efficiency, changing what machines could do and where they could operate. As a result, many blue-collar jobs morphed or disappeared. New terms emerged: “rightsizing,” “reengineering,” “lean operations,” euphemisms for workforce reduction.

Typing (keyboard skills) on the factory floor, in the warehouse, and at headquarters became essential for success. Workers who once dictated memos now had to learn and use WordPerfect. Ergonomics became a concern as computer use increased, and repetitive strain injuries and eye fatigue became part of daily life as hard drives replaced filing cabinets and the sound of dot-matrix printers overtook the hum of typewriters. Office layouts evolved with an increase in open-plan designs and a decrease in private offices.

The promise of technology was efficiency. However, for many, the reality involved change and even displacement. Workers who previously depended on institutional memory and structure found they had to start building their own. The idea of Free Agency in this era suddenly became a reality for those laid off or downsized. Meanwhile, for others, a form of digital emancipation opened wide. Barriers to creativity and entrepreneurship, both internal and external, melted away via the rise of digital tools and the invention of entirely new jobs.

The Jack Welch Era

Jack Welch was Chairman and CEO of General Electric from 1981 to 2001. His presence and his ideas left a big footprint on this era. He didn’t invent ruthless efficiency, but he branded it. “Rank and yank,” cutting the bottom 10%, rewarding the top, became gospel. Stock options began replacing pensions, shifting risk from employer to employee. Loyalty became a liability.

Welch’s GE was the blueprint. Others followed. The message was clear: adapt or disappear. The rules had changed, and they weren’t coming back. McKinsey and its consulting peers followed, emerging as corporate surgeons who prescribed outsourcing as a competitive necessity. The implicit contracts—job security, internal mobility, mentorship—were broken by the very companies that once defined them.

The Jack Walsh persona is, in many ways, the perfect representation of this period of significant political, economic, and geopolitical change, marked by the breakup of the Soviet Union. The stagnation of the 1970s was replaced by energy and a strong sense of action in the 80s, mainly driven by digitization and software development. Workers not directly impacted by the harshness of the Walsh-era corporate overhaul also experienced change, albeit gradually, as businesses and individuals adopted the new technology emerging around them. Meanwhile, seeds were planted that would soon shape a working landscape increasingly bent toward Free Agency.

One of my favorite reads about this period is "Barbarians at the Gate." It chronicles the leveraged buyout of RJR Nabisco, a modest undertaking by today’s financial standards, yet a big deal in its time: excellent writing, a riveting account, a true peek behind the deal-making curtain.

Worker Adaptation

During this period, especially in the 1990s, career self-management evolved from simply advice to a guiding principle. “Portable skills” became a popular phrase with significant real-world implications. Between 1980 and 1999, the share of people working multiple jobs increased from 5.8% to 7.8%. Dual-income households went from being a luxury to a necessity.

New industries, such as career counseling, resume services, and job placement firms, emerged to address the opportunities as the world of work moved further away from the company-centric era of the past. The market for “What Color Is Your Parachute?” rapidly expanded. “Dress for Success” became a cultural mantra.

Early iterations for the individual as a brand emerged, setting the stage 10 years later for Tom Peters’ “The Brand Called You.” For those with an entrepreneurial spirit, this economic and societal shift landed right in their wheelhouse. Others, however, responded differently to the changes happening around them.

The Day-to-Day Shift

The shifts in work life during the late 1980s and 1990s were both structural and personal in nature. Cubicles replaced offices. Commutes lengthened. Casual Fridays emerged, but expectations remained high. Office politics grew more intense, and “workplace toxicity” became common vocabulary. Email had taken over memos, and software skills, such as knowing Excel, WordPerfect, or Lotus 1-2-3, were no longer about getting ahead; they were about staying afloat.

Then came a quiet shift: someone stayed late not to finish work, but to be seen working. It wasn’t just about output; there was now an element of optics. Visibility became a proxy for commitment. The work hadn’t changed much, but the stakes had. The grind extended beyond tasks into reputational management.

This shift was subtle, driven by survival instinct and ambition. Mass layoffs, flattened hierarchies, and constant restructuring created a low-grade unease, even among those untouched. A new internal logic took hold: things are changing, my career isn’t secure, and self-promotion might be necessary. Standing out became as important as fitting in. The emotional contract between employer and employee began to fray.

That’s when “work-life balance” turned into a punchline. Not because people stopped caring, but because the system stopped rewarding it. Flexibility entered the language, but not the culture. You could leave early, yet risk being seen as less committed. Take a mental health day, and your manager might quietly mark you as unreliable. The freedom was performative. The pressure was real.

This wasn’t entirely new; earlier times had their own issues. But something basic had changed. The restrictions on careers were lifted. New tools and rules allowed people to work independently. For some, that was freeing; for others, unsettling. Choosing between old-school loyalty and new-school flexibility wasn’t always simple or clear.

The transformation was both cultural and infrastructural. With the prevalence of email, mobile phones, and remote access, the boundaries between work and personal life have begun to blur. The office followed you home. The inbox became a 24-hour gateway. And success quietly shifted from “What did you achieve?” to “How constantly are you reachable?”

Why This Era Still Shapes Us

This period marked the shift from institutional loyalty to personal agency, from linear progress to modular reinvention. It was the moment the social contract started to unravel – AND – the origin story of today’s career landscape.

In the 1980s and 1990s, Americans faced declining pensions, less job security, and lifelong careers transforming into “at-will” arrangements. The corporate ladder changed shape, twisted, and in some cases broke apart. Workers were told to be adaptable, entrepreneurial, and self-reliant, but they weren’t provided with the necessary tools to succeed.

A new type of cognitive load emerged: managing not only your role within an organization but also your outward image—your brand and value proposition. Email, the early internet, and performance metrics blurred boundaries, making visibility and accessibility essential for effective communication. That pressure only increased as the new Millennium began.

It also fostered the freelance mindset. When companies ceased investing in long-term careers, workers had to prioritize their own careers. Portable skills, personal branding, and strategic pivots moved from buzzwords to vital survival strategies. What began as a reaction evolved into a guiding principle: own your path or risk being invisible.

This marked the end of the traditional career path. College no longer delivered guaranteed stability. Promotions became political. Entire industries were disrupted. In response, Americans began building careers from fragments, adding side gigs, certifications, contract roles, and creative projects. The ladder disappeared. The portfolio was born.

This era also sheds light on the contradictions of today. Autonomy feels empowering and exhausting. Flexibility is sought after, yet pressure continues to rise. We inherited freedom without support, choice without guidance, and responsibility without recognition.

The 1980s and 1990s were a pivotal time. They laid the blueprint for today’s hustle. Understanding how we got here is the first step toward reclaiming control in a system that still expects us to manage it on our own.

In the next post, we’ll explore what happened when that blueprint became reality. Between 2000 and 2025, the concept of a portfolio career shifted from a niche idea to a mainstream necessity. Job tenure decreased, income streams increased, and technology enabled new ways of working. Economic volatility required constant reinvention.

The result is a generation of working Americans who build careers like ecosystems—fluid, decentralized, and self-directed. In a world where no institution tracks your value, personal infrastructure becomes essential. Because in this new reality, success belongs not just to the skilled, but to those who are self-directed, informed, and keep track.

Onward.

The Career Revolution, Part II

When Companies Were Forever (1945–1979)

In 1969, IBM had a “full employment” policy. They explicitly guaranteed they would never lay you off. Try explaining that to a Gen Z worker today. 😗

It may sound like fiction now, but for a generation of Americans, corporate permanence was truly just that — permanent. From the end of World War II until the late 1970s, the American workplace was built on stability rather than volatility. The economy thrived. The GI Bill opened doors to education and homeownership. Union membership stayed around 35%, providing a second layer of protection. And the path was clear: education → job → house → family → pension. It was game on for the American Dream.

During this period, companies were more than just employers; they were immersive ecosystems that shaped identity, community, and daily life. Work offered stability, a sense of belonging, and a broad social infrastructure that went well beyond the job itself. IBM’s “full employment” philosophy meant no layoffs ever. AT&T operated like a quasi-government agency with clear promotion schedules and extensive benefits. General Motors built entire towns around its plants, complete with bowling leagues, annual picnics, and company-sponsored recreation. You worked for and belonged to a company.

This was a time when a person's work and career identity were strongly tied to their corporate affiliation. You weren’t just an engineer; you were an IBM engineer. You weren’t just a manager; you were Ma Bell. The company provided everything: training, development, and career guidance. Your path was laid out, your loyalty was acknowledged, and your future was secured.

Organizations served as custodians of institutional memory, maintaining documentation internally, including yours. Annual reviews were stored in personnel files, and your supervisor knew you personally and understood your work, so there was little need (or tolerance) for self-promotion or tracking achievements. Advancement within the organization was based on loyalty and consistent performance, not on personal branding. Career growth depended on tenure and trust, not visibility.

Retirement was viewed as a clear endpoint. Skills were deliberately company-specific, designed to boost your value within the organization rather than, like today, to make you appealing on the open job market. Families built their lives around the company headquarters. Entire towns were shaped by corporate influence. It was common for multiple generations to work for the same employer, passing down not just jobs but also identities.

I experienced this firsthand growing up on the Iron Range in Northern Minnesota, where company towns, called Locations, were common. I spent a lot of time in one, Fraser, MN, which no longer exists. The city began in 1923 and was shut down in 1973; all the houses were moved or bulldozed, and what remained was eventually swallowed up by the Sherman open-pit mine. I think about it often, a place where I hung out with friends playing pickup basketball and scrap hockey, now vanished, part of the economic change in the '70s.

Economically, this period “worked.” Real wages increased. Homeownership rose. Pension coverage expanded. Socially, single-income households became common, supported by suburban growth and Cold War-era manufacturing strength. Internationally, America remained unparalleled with an industrial base powering both domestic prosperity and global influence.

And yet, beneath the surface, this system had limitations.

It was exclusionary, rigid, and often paternalistic, growing “fat and happy” and largely unaffected by the social and cultural issues of the 60s. However, the chickens came home to roost with the 1973 oil shock and the subsequent energy crisis, triggered by the oil embargo imposed by Arab members of OPEC.

There were problems during this time, and I don’t want to downplay any of them. However, that’s not what I’m focusing on here. I’m comparing then and now because this period, with its many flaws, offered something that today’s workers rarely experience: a sense of psychological security. It wasn't just about a paycheck; it was about a shared understanding that your role had continuity, your contributions were recognized, and your future was planned. You weren’t merely employed; you were part of a system that guaranteed acknowledgment, protection, and growth. The belief that your work would be valued, your career supported, and your identity upheld was built into the system.

But that scaffolding has disappeared. The rise of lean organizations, gig work, remote teams, and algorithmic oversight has stripped away the infrastructure that once supported long-term career viability and visibility. Quarterly metrics have replaced annual reviews. Tenure has given way to churn. Managers rotate faster than their reports. And in many cases, there is no manager, just a dashboard.

I’ll talk more about this in my next post, focusing on the 80s and 90s, when jobs and employment shifted away from the post-World War II system I’ve discussed here. For workers, it’s been a slow move from permanent positions to “flexibility.” This change, despite shocks and setbacks like the Oil Embargo, the hollowing out of the Rust Belt, Japanese competition, globalization, the dot-com bubble, 9/11, and others since, has happened gradually over more than 40 years as pieces of the old system fell away.

The days when organizations actively tracked and shaped an employee’s career path are mostly behind us. Today, that responsibility has shifted to the individual, who must now create, manage, and share their own professional story. This shift is a fundamental change, and the “sense of psychological security” has disappeared, regardless of whether it was ever truly there or just an illusion. Planning, documentation, and strategic framing now rest on the shoulders of everyday American workers. Despite all kinds of tools, tips, and digital hacks, many navigate this new landscape with little grounding or clear guidance, as if hoping the old systems will somehow return. It’s like a cultural sleepwalk—waiting for a kind of career stability that belonged to the mid-20th century, a time most of today’s workforce never knew. The truth is, that era isn’t coming back. The sooner we accept this, the better we can create systems that fit the world we’re working in.

This shift toward greater levels of Free Agency continues. I am deeply concerned about this from a civic and social perspective, as things are out of balance and worsening. This, in turn, increases the responsibility on each person to do what they can to function and hopefully progress as we approach our 250th American anniversary.

In my book, Getting Beyond Your Troubled Past, I aimed to emphasize to job seekers with troubled backgrounds that they are truly Free Agents. To help them see that once they are out and away from any form of institutional support, they are on their own, which can be a harsh realization for many who have grown accustomed to institutionalization, regardless of how negative it might have been. Still, they need to wake up and adopt a mindset shift to prepare for a challenging Marketplace that couldn’t care less whether they sink or swim.

Well, the same mindset shift applies to the average American worker. Instead of building silos and moats, the path to success requires individual effort and strategic self-management within the existing systems. There are many things I would like to see changed in our system, but it will take time and more people taking action for this to happen. Meanwhile, I’m here to deliver a few tools to help make successful self-management a reality.

If you’re having trouble overcoming a background obstacle that hinders your progress in work or life (or know someone who is), pick up a copy of Get Beyond Your Troubled Past.

If that’s not you (thankfully), stay tuned for the release of my next book later this year, *Get Beyond the Grind: Work Journaling with The Grind Dairy.*

For now, follow me here or on LinkedIn and “the socials” for more updates on being a heads-up Free Agent. And check back next week for Career Revolution, Part III.

Onward!

The Career Revolution, Part I

I grew up in Northern Minnesota, in mining country. There were some office environments similar to the pic (circa 1965), but mostly, this happened in metro areas like Duluth or, of course, the Twin Cities. Still, the work culture MO fits—ties, typewriters, and uniformity. You worked for one company, rarely switching jobs, and the idea of having a 'side hustle' would have seemed as foreign as carrying a computer in your pocket.

Today, we watch reruns of Mad Men to see what life was like back in the day. Things have changed. Now, the average job lasts 2.8 years, and 36% of the workforce is involved in gig work. And white shirts with narrow dark ties in the office?… come on.

In my upcoming posts, I’ll explore the last 80 years of work in America. I’ve experienced most of it firsthand and observed the differences between these periods. But this isn’t just a walk down memory lane; it’s what I need to do to understand how we got to where we are today, on the verge of major economic change driven by technology, especially AI.

Connecting the dots, era by era helps me, and I hope you, see where we came from and how we reached this point today. I’ll examine:

• Organization Era (1945-1979): "When your company was your career"

  • Quick snapshot: lifetime employment, predictable ladders, institutional identity

• Transition Era (1980-1999): "When the rules changed overnight"

  • Quick snapshot: downsizing, technology disruption, survival mode

• Portfolio Era (2000-2025): "When everyone became an entrepreneur"

  • Quick snapshot: gig economy, personal branding, individual responsibility

Popular culture has become a spectacle of wealth, celebrity, and curated lifestyles that seem increasingly disconnected from the real experiences of most Americans. We’re bombarded with highlight reels—private jets, brand deals, and “quiet luxury”—while most people face very different realities, working hard just to keep things afloat. The cultural narrative cheers for the few who aren’t involved in everyday work, while ignoring the millions who keep everything running. I’m not very interested in the former. That side of the story already gets too much attention. I’m focused on the latter. The true story belongs to the people who show up every day, solve problems, build systems, and carry emotional weight without recognition.

What we call “ordinary” work is anything but. It’s strategic, adaptable, and deeply human. Yet, it’s rarely documented, celebrated, or preserved. The nurse who charts patient care between emergencies, the warehouse manager who motivates a team through chaos, the freelancer stitching together income streams with no safety net—these are the essential players of modern life. Their contributions are foundational, but their visibility is often limited. I’ll discuss this and how to improve it.

I am fascinated by what comes next work-wise here in the USA. It’s on my mind now and most days, and I believe it should be on most people’s minds as well. As AI reshapes industries and automates tasks, the value of human work will shift from execution to insight. The average worker won’t just need new hard skills; they’ll need to see themselves in a new light—as the Free Agent they truly are. Furthermore, to succeed moving forward, workers will need to position themselves to compete in a marketplace with new rules. Adaptability, strategic thinking, and lived experience all matter, but if they aren’t captured and tracked, they vanish into space.

The future will be shaped not by influencers but by those who know how to work, adapt, and lead from the ground up. And they’ll need tools that make their contributions visible and usable—and to this end, a page or two from the Self-Promotional Influencer Manual. We’ll explore this further, too.

In the meantime, for those digital natives out there, imagine a time before smartphones, streaming, social media, flip phones, the internet, personal computers, and even fax machines. How did people manage back then? What was it like to work in those days? We’ll take a look.

One thing, though, is crystal clear: we as people haven’t changed much, but technology has. Since back in the day, housing, transportation, food, clothes, recreation, and most other things have been upgraded, tweaked, and improved, sometimes in significant ways, but not to a paradigm-shifting extent. Not so for tech and the digital world. Here, especially now with the race to AGI, words like sea change, disruption, (radical) transformation, and even revolution do not seem out of place.

Digital technology has profoundly affected our lives culturally, socially, and politically, leading to polarization and discord. While this has been challenging, it is minor compared to the potential impact if jobs and employment are heavily affected. I’m not only talking about job losses; AI could eliminate the core of many well-paying jobs as more output is produced at continuously lower costs.

The train has left the station. There’s no stopping it now. So what’s the plan? Firstly, people—specifically, American workers—need to get on board. There’s no option. The good news is that the same technology causing disruption is also the one that can help us improve. We’ll cover this further as well.

Stay tuned.

Next up:

Organization Era (1945-1979): "When your company was your career."

Onward!

Authenticity

If writing my new book were a journey down the Mississippi, I’d position myself somewhere between Hannibal and St. Louis, not quite cruising under I-55 in Memphis as planned, but not stuck on the riverbank either. The current’s flowing, and so am I, just slower than expected. New goal: rough draft by the end of August. I’ll keep you updated.

Although the main point of the book is about tracking your work experiences with my Grind Diary method, authenticity remains a significant concern—and it continues to occupy much of my thoughts as I write. I’m considering authenticity in the context of digital, AI, and Web 3, related to content that either stays true to its original form and intent or becomes manipulated or altered. Overall, this kind of authenticity is a hot topic right now because of how fast and widespread AI technologies are evolving.

The LLM locomotives are racing across the landscape, unstoppable, in pursuit of the Holy Grail of AGI. Society and most individuals are unprepared for what lies ahead on many levels, including the ability to easily and accurately tell reality from illusion or to distinguish the genuine from the fake. It’s becoming harder to tell now; imagine what we’ll face in 5 to 10 years.

I foresee a near future where people will seek ways to “authenticate” themselves, to show, demonstrate, and prove their identity because all the traditional methods (IDs, documents, multi-factor and knowledge-based authentication, even biometrics) will become malleable or easily manipulated. When AI can mimic tone, style, and biometric patterns, the burden of proof shifts. It’s no longer enough to say ‘I did this’; you’ll need a trail that confirms you.

I am not attracted to techno-conspiracy theories, perhaps because I grew up near the headwaters of the Mississippi in Minnesota, or maybe not. In any case, I’m an AI user and follower, and I believe we, as a society, are no longer drifting down a gentle river; we’re heading toward Cherry Creek, the Upper Tuolumne River. The Mississippi meanders, but the Upper Tuolumne requires precision, agility, and preparation. That’s the kind of current we’re about to face.

Three core concepts explored and developed in my first book, Get Beyond Your Troubled Past, are: Free Agency, being a Seller of Service, and operating in the Marketplace. These ideas continue to apply to job seekers facing background challenges, but now resonate with larger portions of the general population. More Americans are experiencing Free Agency as job tenure decreases and portfolio careers become common. They are forced to see themselves as sellers of something, possibly as a commoditized brand in an unexpected way. In a synthetic economy, being a Seller of Service means proving you’re not synthetic yourself. Meanwhile, the Marketplace is constantly changing with one economic reset after another. This is where we’re at now, and I fear the big rapids are still ahead.

The primary focus of my upcoming book is documenting your work experience. I discuss the many benefits of doing so, one of which directly relates to authenticity—the ability to prove, through your (own) records, that you are who you say you are and have accomplished what you claim. Historically, tracking your work has been helpful, even as a simple reference. But now, a new element has appeared—authenticity itself—which is no longer guaranteed in today’s rapidly changing digital landscape.

Stay tuned for updates on my Grind Diary progress as I metaphorically cruise past St. Louis on my way to a rough draft near Memphis. In a world where proof becomes currency and authenticity can no longer be taken for granted, the Grind Diary isn’t just a tool; it’s your ledger of legitimacy.

Meanwhile, the river is stirring. Record what matters. The rapids won’t wait. Game on.

John

PS - Hey, a leisurely trip down Big Muddy sounds pretty good as I spend another morning tapping the keys.

PSS - Take a peek at the Upper Tuolumne River.

Onward!

July 4, 2037

This year is the 10th anniversary of my book Get Beyond Your Troubled Past. Included in it are three core principles that I believe are critical for reentering citizens to understand: Free Agency, Selling Your Services, and Operating in the Marketplace. The successful incorporation of these begins with a mindset shift. It progresses to identification, which means seeing oneself as a Free Agent, a Seller of Services, and someone able to navigate the Marketplace.

Little has changed in ten years; if anything, these concepts have become even more fitting for those reentering. However, there’s a new twist: they now apply to a growing percentage of the rest of the population, those not encumbered by background issues.

We are experiencing a profound shift in societal perspective, one that holds the potential to redefine fundamental frameworks. There is a strong argument that this marks a true paradigm transformation. For the sake of discussion, let’s refer to it as the 4th Radical Change, listed below with the previous three that roughly coincide with the existence of the USA:

First Industrial Revolution

1760-1840

Second Industrial Revolution

1870-1914

New Deal Era of Big Government

1933-2016 (+/-)

4th Radical Change (to be named)

20XX-XXXX

We are in transition, both societally and economically, as well as politically. There will be a name for this new period, and future historians will likely assign it a start date, perhaps sometime between 2030 and 2045, based on past transitional timeframes. However, the name and date are for later; what’s important now is recognizing what’s happening all around us—change.

The drivers are numerous: globalization, technology, climate change, demographic shifts, and others. The way things were in the New Deal Big Government era is giving way to something else, exactly what, it’s too early to tell, but it will be new and different. One trend that’s clear to me, essentially born out of my work a decade back, is that we are all becoming Free Agents.

Before delving into this, I want to make two points regarding change and transition, era-wise: The first is that we’re not yet at the next epoch (not just here in the US, globally). The second is that cataclysmic events are intertwined with past transition periods (for example, 1860-1865, 1914-1932, & 1939-1945 associated with the 2nd to 3rd transition). Somber stuff, to be sure, so please take a look for yourself if these “dates in history” don’t stand out to you.

What this boils down to is change and disruption, something that, despite our fragmented and polarized current state, most people might agree we are experiencing in new and disquieting ways. This makes reentry more challenging to write about, not because I have any reservations about my approach, which emphasizes sustainable self-sufficiency, personal responsibility, and client ownership of the reentry process, not in the least, as my Get Beyond It All approach fits well with the current DC MO.

Instead, I see the status quo support structure melting away (in itself, not a bad thing) with little to replace it (which is indeed very bad). The example that comes to mind is the reduction and/or elimination of the Affordable Care Act/program with nothing, which is to say, N O T H I N G, to replace it except, of course, private for-profit options stealthfully waiting in the wings. For a glimpse, take a look at how things are progressing in the rural hospital space if you’re unsure. Not a perfect example, but you’ll get a sense of it.

All of this will take years to unfold. For now, each of us is tasked with doing our best work given the current circumstances. To this end, I am working on a new book and related project, Get Beyond the Grind: Work Journaling with The Grind Diary. I’ll have more to say about The Grind Diary Approach and how it can help not only those reentering the workforce with background challenges, but everyone navigating the Marketplace as a Free Agent.

In the meantime, consider the transition we are all experiencing now and ask yourself: Where will I be, and what will I be doing on July 4, 2037? Be specific, give yourself an exact date. Dwell on it, connecting the dots in reverse to the present. We should have some idea about this next era and perhaps even possible names for it. There are many possibilities; however, I’m convinced that Free Agency will be fully baked in the cake by then, but I can’t say how... hopefully for the better.

More soon.

Onward!

Managing The Gap

An inevitable step in reentering is putting together your resume, which is based on your work history. But there’s a gap, maybe more than one. Yikes. Now what? It’s going to be a problem. Someone’s going to spot it.

Exactly.

And sure enough, if you submit your resume along with applications to random jobs, it will be noticed, and it will be a problem. And you won’t move forward.

Here’s how to manage the gap using the Get Beyond It All approach.

But first, a few things need to be in place. You need a Plan, a Job Search Objective, and you must have your Delivering the Mail statement (in essence, your elevator pitch) ready on a moment’s notice. I write about these essential precursors frequently, links attached.

Here’s the setup.

You will go out and meet potential employers in person, onsite, whenever possible. They will not be random. You have an Objective (a point of entry) based on your plan, and you’re working it. Time for an aside: If you are not going out and introducing yourself to selected individuals or businesses (and instead blasting out resumes and apps online), you’re swimming upstream, at best. Digits are not your friend. Get this!

Okay, back to it. You're out and intend to meet people face-to-face. To be clear, this does not mean “dropping off resumes.” If you can’t meet someone directly, find out who (if you don’t know beforehand) and go back. Another aside: If your reaction is, “Well, that was a waste of time…” Your attitude needs a check. You picked the place and had the opportunity to see it up close, learning something you can use when you return. Period. You “win” every time because you come away knowing more than you did going in.

Let’s return. You do have an opportunity to meet…Bob. Good. One more aside: You’re ready to meet Bob, which is to say, you’re dressed right and smell good. Game suit and game face.

You introduce yourself to Bob. You tell him you're looking for work and are ready to go. Bob may say any number of things, most of which you’re prepared for. In this case, Bob says, “Well, we’re short a couple of positions in the warehouse…” You say, “Okay, great. I brought a copy of my resume.” You hand it to Bob and wait. Bob looks it over and pauses (at the gap). - PERFECT - You say, “You’ll notice a gap in my work history, let me explain that.”

And here is where you Deliver The Mail. Then wait for Bob to respond. Aside: Your DTM is a succinct and well-practiced statement about your background issue.

Bob will say one of three things:

• 1) Yes/maybe

• 2) No

• 3) It depends

“Yes/maybe” means you are making progress—you’re not anywhere yet, but there’s a possibility. “No” means Bob can’t hire you, but he might be able to help. You say, “I understand. Is there someone you’d recommend I reach out to that might be in a position to hire me?” Just asking the question means you’ve chalked up a “win” with a chance to move yourself forward. As for getting an “It depends” reply from Bob…You say, “Okay, I’m ready to take the next step. What should I do?”

If you take the initiative to prepare, show up, be presentable and polite, most “Bobs” will treat you right. They may not be able to assist you outright, but they may give you a handoff.

And the gap in your resume? It becomes a tool. Something you use and move into, not away from. You wanted Bob to see it, and you wanted it to happen right there, on the spot, in front of you. What you don’t want is for someone who is screening apps (Bob or otherwise) to reject you, digitally or on paper, without ever meeting you.

The subtitle to my book, Get Beyond Your Trouble Past, is: You’re Not Looking for a Job, You’re Looking for a Person. And you are.

You’re looking for Bob or Roberta. They are humans, and they can help, but only if you meet them in an orchestrated way.

• Your Plan

• Your Objective

• Your DTM statement

• Your effort

It is NEVER random. Do the work.

Onward.

Preparing To Win

For someone hampered by a significant background issue, such as a felony, there are three possible outcomes when pursuing employment: green light (the employer accepts it, move forward), red light (they will not, full stop), or yellow light (maybe, case-by-case review). The challenged job seeker must prepare for each scenario; however, the third deserves particular attention because this category can produce opportunity and (significant) disappointment.

Evaluating on a case-by-case basis means, as a practical matter, some offenses will be out-of-bounds and quickly judged as a no-go, and some will be judged as less severe and perhaps familiar to the employer, they’ll receive a green light. The rest will be in the gray area, and various factors will be considered, such as work history, education and training, recommendations, and references—and, in no small measure, a candidate’s presentation and likability.

Regardless of the specifics of the process and the “other” things weighed, the formal background check will be the tail that wags the dog, the Mondo Factor influencing the final decision. With so much riding on the background check, you would think every background-challenged job seeker would secure a copy of their criminal history.

But no, many don’t. The result? They aren’t prepared. They fly blind.

Reentry and searching for the all-important First Job should begin by getting one’s background/criminal history report. In the best of all situations, this would happen before someone is formally released from incarceration, completes a substance abuse treatment program, or officially comes off the street via a reintegration program.

However, based on my experience (past and present), this rarely occurs because organizations and programs are balkanized, doing this but not that, mandated one way with little leeway to stray from their designated lane. Furthermore, the handoff from one organization to another frequently sucks. My apologies to those few that excel in this area, but they know that, on the whole, program coordination (if there is any) is abysmal.

In general, background reporting takes three forms: criminal history reports from the FBI and the states, and private vendors’ reports that cover criminal history and other areas. The how-to-get-it information for all these options is readily available, although selecting a vendor for the private route can be confusing. For this reason, I recommend starting with a state-issued criminal history report if all offenses occurred in one state.

In any case, the point I am making here is that getting your report is NOT DIFFICULT. What is difficult is recognizing the importance of taking steps to proactively get your report without someone else leading you by the hand to do so.

So why should you? There are numerous reasons, here’s my top three:

• Preparation. You can’t plan your search and fully prepare for what’s ahead until you know what prospective employers will find when they check your background. Not knowing means you are indeed flying blind. You need this info, and you need to get it directly. No copies of what other people found. No. Get it yourself. Moreover, doing this is very proactive and gets you started with the right mindset.

• Verify Accuracy. Errors are not uncommon, so check your report, line by line. Other people can make errors, certainly, but you can too. Often, reentering people forget minor charges and details of how the charges were filed, such as if there’s been some back-and-forth before or in court. But know this, until an official report is changed, it stands. Even though there may be inaccuracies, employers will see what’s listed when they run the check.

• Control the Narrative. How can you explain your background situation to anyone else if you’re uncertain what they will see when they eventually check? What you say up front must match what they will find. How you introduce yourself and your background issue can determine the eventual employment outcome, especially when there’s a case-by-case situation in play.

There’s a lot more I could say about background checks and criminal records, but I’ll sum it up here: You need to get your report(s) and do it yourself because the success you experience (or don't) will depend in large part on what other parties find out about you. Knowing helps you prepare and you are not likely to succeed if you try to wing it.

Okay, so why don’t people who reenter do it independently? First, some do, which is excellent, but many (most) don’t, which is not so good.

• No bandwidth. Reentry starts as other stuff ends. Too many puzzle parts fly around, leaving precious little time to focus on any one thing. Many such things become lost in the tornado, like the image above.

• No money. Even though the cost is minimal, there’s still an associated cost and hassle, so some things lag while others take precedence.

• No interest. Angry at everything with no desire to be proactive in the planning sense. This, of course, is counterproductive, but it happens.

• No awareness. The importance of doing this and obtaining this information is unseen. It’s not top-of-mind or anywhere else. It’s just not on the radar for whatever reason.

There is no plan. Reactivity rules the day. It continues. Wants and desires may be there, perhaps in a big way, but there’s no roadmap or game plan for achieving them.

Reentry success requires a Free Agent mindset where you see yourself driving the bus, being proactive, and as someone who prepares. Knowing everything you can about the one big thing that separates you from the other 70-odd percent of the US adult population (your record) is on you.

You are competing with them. They have the advantage.

So take yourself seriously. Plan, strategize, and use everything in your playbook to take on the fight in the Marketplace. Why are you any different from any other competitor? You aren’t. The Marketplace takes each participant as they come. Be prepared to win regardless if you lose. Challenge yourself to take something of value from every situation and encounter.

Learn, adapt, go at it again. Prepare.

Task #1

Get your background report. Get it yourself. Get it today.

Onward!

Don’t Mess With Digits

I wonder what increasing digitization means for reentering citizens and others with background baggage. This “wondering” is hardly new; it’s been underway for seventeen years since the early notes for my book, Get Beyond Your Troubled Past, first came together. And now, here we are with AI (digits on roids) seeping into every nook and cranny of our 21st-century lives.

In yes-or-no terms, does ever-increasing digitization help or hurt the background-challenged job seeker? I ask this rhetorically because there’s a continual Spy vs. Spy (yes, right out of the old Mad magazine) contest regarding background checks. Vendors of checking tools (platforms and apps) regularly add new technology features and twists, only to see them countered in some way by situations in the Marketplace. This is serious business, to be sure, and yet this cat-and-mouseness is intriguing to watch, with occasional unexpected consequences, like the social media discussion below.

But I’ll cut to the chase and say that in my view, despite the ebb and flow of action and reaction, adding more digits and specifically AI to the fray DOES NOT benefit the challenged job seeker—which is to say (continue to say…) the digit is no friend to the reentering person.

According to vendor data, businesses are NOT pushing back on using AI in various ways to conduct and record background data. I accept that if for no better reason than the regulatory framework around AI is so…what? Behind, non-existent? Anyway, I can see very little regulation, and given the political climate in DC these days, well, game on, AI. We can expect more and more AI-embedded features in checking products, not less.

AI-enhanced background-checking products push the bar higher in three areas: work history, education, and social media checks. Work history (employment checks) is not without its challenges, but overall, more APIs and data integration mean more information that can be accessed more quickly. No real surprise, but there is one regarding social media checking.

Over the years, employers and HR staffers have done their own social media research on candidates, finding all sorts of protected information (age, race, religion, gender). Possessing this information, not to mention using it in hiring, can be problematic, to say the least. Yikes. Nonetheless, interest in a candidate's social media profile isn’t going away (ever).

So, the question for businesses is: How can we get the goods without liability?

Hire third-party specialists to do the research. This reduces bias issues and protects the business/HR department. It’s better to proceed with specialists who know the rules rather than digging around without guardrails. And so, the bar goes up. Social media checking (a menu item already on the options list) becomes increasingly more effective and a “must-have.”

So, in the ebb and flow of things, what does this mean for the background-challenged reentering person? Simply put, there’s less and less margin for error—or “discrepancies” from the background checker’s point of view. And here’s where I stop the bus and clarify that I am not referring to lies or flat-out misrepresentations. No way. There is no place for this, regardless of the situation. That said, digital background-checking bars that continue to move higher create a perfect storm for errors.

For many reentering people, not all the details are available. They have been lost in the shuffle of a collapsed life and a new one under construction. I don’t know, or I don’t recall—they are for real. They can be actual unknowns. But digital applications don’t like “I’m not sure.” Thus, things are left out or best guessed. Most of the time, it works out if the effort is genuine or if there’s an opportunity to include additional information elsewhere on the application. However (back to background checks), what happens when a more detailed check is done later, for a big promotion, or when tools and features have been added to the standard check between getting hired initially and being promoted? Discrepancies may pop up.

As for social media, it can be a theme park of problems, complicated and thorny. My advice for the reentering person hasn't changed. If your Job Search Objective is in a professional or niche arena, you may have to have some social media presence to be considered. If so, present yourself thoughtfully and carefully. If you do not need a social media profile for the type of job you are going after, have none or one that’s minimal and uncontroversial.

This all boils down to the following recommendations for anyone reentering or helping someone who is:

• Be straight up, honest, and genuine - always, full stop.

• Do your best to represent yourself and your situation when dealing with digits accurately.

• Build relationships with people (People Links, as I call them) who get to know you personally and how you work.

• Develop a plan, subdivided into defined action steps, that will guide your job search and help you move forward once you start looking for your first job.

Searching for a job and, even more importantly, moving up to a new job without work-related human relationships (professional People Links) is like skating on thin ice. You might make it, but why chance it? The background issue is not likely to disappear, especially in our digital world. Genuine relationships, developed through effort and consistency, can act like an extra layer of ice, supporting you across the frozen lake.

Onward!

You Too, Will Tranistion

By definition, people with background challenges who reenter the workforce are in transition. Of course, they go from being unemployed to working, but most will also move from one system to another—from the social service economy to the free-enterprise capitalistic economy.

Returning to the workforce requires many steps and a great deal of effort. Think about the last time you needed to search for a new position, presumably without the limitations of background baggage. Most people hate looking for a new job; imagine starting over after addiction, homelessness, or incarceration. It’s a big undertaking with many moving parts.

One critical area often overlooked is the mental adjustments needed to transition to the new system successfully. The physical part of this is easy to understand (new clothes, new ID, new people to meet, new processes to manage). Dealing with all that is a lot, but it can pale compared to the unwritten and assumed rules of the road that require understanding to achieve a positive outcome.

Changing from a system where dependency (in part or whole) is the MO to one where accomplishment rests solely on one's shoulders can make or break someone's reentry, mainly if they’ve been off the market for a long time. I call this adjusting to the Marketplace. It usually entails heavy lifting and a tough road to succeed in our capitalistic system.

So why are the intangibles of this transition skipped or overlooked? Okay, I’m sure I’ll ruffle a few feathers here, but so be it. The program administrators are part of the system that supports and then launches the reentering client into the other system. They “live” in a system 180 degrees from the one their reentering clients must navigate to find success. Look, nobody’s acting bad or doing the wrong thing here. But when programs and staff don’t venture into the other world, they do not fully prepare their clients for what’s ahead. Indeed, some do, and that’s great, but many are OTL regarding real-world prep.

Okay, here’s my real message: The transition that most of your clients must make is coming to you and your program. It may take a while, but your current funding sources will eventually need to be re-upped, and that’s when the change in wind direction will be felt full-on.

So here’s my suggestion to help your program with this transition. Think of your reentry program as if it were a client. Imagine moving your social service program (as all reentry programs are) to the “other” system, the one that’s for-profit, free-enterprise, and capitalistic. Shrink your entire program down to one persona. Slip into the client’s shoes and walk from one environment to the other, adjusting just like them, physically and mentally. Picture competing with everything you can imagine in an environment that’s a foreign land of ideas, beliefs, and processes. Imagine playing by their rules and competing on their turf.

So, what exactly is coming down the pike? No one knows, but a worse outcome scenario is that your program will be eliminated. That’s an unacceptable disaster. The need continues, and given the potential outcome of connecting the dots, it will most likely grow. So, your mission is still your mission; nothing’s changed. The question is, can you adapt to a new environment if needed?

Can you transition just as your clients must from a social service system to something different?

To be clear and transparent, I believe the social service world needs many updates. I don’t have any philosophical or political axe to grind, but I worry about how things might turn out. I am active in both worlds: as a reentry advocate and educator and a recruiter specializing in acquiring talent for startups and early-stage companies. I can see and appreciate both perspectives. In a sense, I sit on both sides of the interview desk. It’s clear that change is coming, and I implore program operators to be proactive so you are ahead of the curve and making the necessary decisions before they are made for you.

Onward!