I spent 12 years, then 5 years at companies doing executive support training people to use industry specific CRMs.
Then went out on my own as a copywriter (totally different skill set). The majority of my income has been from agencies. Very much a "free agent" feeling.
This last year I started looking for something more consistent. So I went back to looking for what I did for 17 years.
Nothing.
Even applied for jobs I was massively overqualified for and couldn't even get a response.
You’re not alone Adam, the market is really strange right now. As companies figure out the new shape of the workforce in the world of AI, they’re moving in slow motion. It’s gonna get worse before it gets better. I believe everyone needs to embrace the free agent mindset.
This is a great take and I feel like you just explained my recent situation. Your line "Work hard, deliver, and stay loyal. The company will do the same…so long as it’s in their best interest." seems to be a very outdated concept. I began with a startup, was offered phantom units for my early unpaid work, and earned a decent paycheck as a chief officer. But when times got tough, there were no cost of living increases. No bonuses. No anything. And a CEO who mismanaged money to a potentially criminal level. Luckily, I'm decided to start picking up new skills in the AI world about 12 months ago and was able to resign (before getting laid off) and have a job within minutes to cushion the fall while working to start up my own endeavor so that I'm not reliant on someone else in the future. Thank you for sharing your story.
Sorry you went through that, Todd. To your point, it’s outdated, but it’s the most defensible option a leader has when times are tough. “Fewer people, do more with less, save the company some money.” They believe if they do it that way, they’ll be saved. (Many are not). On the flip side, I hear Dana White go on Diary of a CEO and talks about a leadership style of leaning into the hard times and protecting his people. Both types of leaders get CEO titles. That’s the game. Appreciate you sharing your story here, thanks for investing the time.
This is a really good article. I think for people who have been impacted by lay offs, the hardest part is to allow ourselves to feel confident again to begin something new and on our own. People always go back to finding another job to a) get bills paid and b) feel that secure cushion again. When in reality, a job is more risky cushion than ever. Thanks for sharing!
It’s tough to build that confidence in the beginning, because you don’t have the usual guardrails to measure how you’re doing. In a job, you have targets, KPIs, QBRs, reviews…but on your own, nobody’s telling you if you’re doing a good job or not. Especially in those early days when you’re figuring it out and spending too much time doing all the wrong things. Thanks for reading and taking a minute to share your POV!
This framing describes exactly what I've been seeing and feeling over the last few years. As a fellow early 40s millennial with an 18 years career in various companies, I can see the split between those who are embracing AI and how to position themselves and others who continue to just show up.
Also there is this current narrative online that the w-2 job is a dead end and you must "burn the boats" and go all-in for yourself. I disagree and think many people are not cut out for building their own thing that will fully support them, and instead should take your Free Agent mentality to their career.
Couldn’t agree more, Judd - solopreneurship / entrepreneurship is not for everybody. It’s a hard road. I’m exhausted all the time. But staying in the W-2 job (which, also agree, is not a dead end) means staying in the system. And as long as you’re in the system, you’re at the mercy of its behaviors. So the ups and downs of rapid growth demanding crazy hours, the company plateauing, regressing downsizing, RIF’s/layoffs, finding something new (either before or after the axe falls), that’s your reality. It’s an acceptable life, as long as you’re accepting it with eyes wide open, knowing what it means.
Yeah it has its big downsides for sure. I think more people could do better at understanding them and optimizing to minimize the negatives while acknowledging and recognizing the positives.
Haha I write this after taking most of the day off because I feel ill. My wife is swamped in client work for her firm and just has to work around any sickness she encounters!
Being a free agent sounds good and having income outside your job is certainly appealing, but it's somewhat ignoring that the job takes up not only 40+ hours a week, but 40 of the best hours of the week. Where is the extra time coming from?
The truth most people don’t want to hear - you have to make them, you’ve gotta fucking scratch and claw for them. They’re small increments when you’re working a 40-hour-a-week (which is usually more for high performers in corporate). You wake up an hour earlier and work before the house wakes up. You stay up an hour late and shave off some of your sleep. You sit in the car at soccer games and write notes and go back and forth with Claude. You build in the margins of your already full life. The alternative is just accepting whatever that 40+ hour a week job gives you. Because nobody’s coming to build the thing for you, or me, or any of us. It’s on us. So we have to steal the time from somewhere else. Can’t do it from home life because you don’t want to implode your family. So you sacrifice something - sleep, TV time, whatever it takes. If you want the thing bad enough, you’ll make the time. You’ll start accepting really small progress as wins. You’ll learn to be more efficient with your time than you’ve ever been. It’s a process.
Thanks Fran! I know, I have friends and former teammates all around the world, and it's impacting everyone. On the one hand, there's nowhere to hide. But on the other, we're all in this together, just trying to figure it out.
Keeping your head down and staying invisible leaves your career entirely at the mercy of internal spreadsheets. Building visible proof of your thinking gives you options before a sudden reorg forces your hand.
It's a little bit of insurance. I've also found untangling problems in public actually ends up helping other people, too. And you get help from unexpected sources. Assuming you're not violating your employment agreement, beyond being tired a lot, there's not much of a downside to building something of your own.
This is such a reality check kind of message. I am at the other end of your spectrum (an aged Boomer). I am a twin girl dad (32) and a father of a special-needs adult son (34). I have bridged the life you described as your parents, plus the new social contract of the next generations. I say my career has spanned three different epochs - corporate life to start-up life to solopreneur life.
I have evolved into designing narratives for corporations (as brand narratives), executives (two versions - complete transformation (ShiftStory) and Executive Sprint (CEO/Founder Narratives) as well as movements (reuse and rethink wine). I have worked with a 1/2 dozen or more future-of-work clients (people analytics, organizational intelligence, Outplacement, recruiting, TA, Presence Management, Organizational Network Analysis, AI-based versions of HR and WorkTech - all names you would know). I also guest lecture at leading universities, speaking with the next gen of hopeful talent.
As someone who is still a practitioner in the trenches, I see the fear and acknowledge that the great disruption is scrambling everyone's ability to navigate with an outdated compass. The reality I see is based on living through four significant inflection points. When I graduated in 1983, I was thrust into a "we only hire MBAs world". Inflation was insane (17%) and getting a job was as good as your ability to hustle and leverage your network. Cable TV and the beginnings of the software revolution were the emerging tech. The first inflection point.
Fast forward to the 90's and the great internet explosion happened. I was on the launch team of Pathfinder (at Time Inc). The writing was on the wall for the traditional media world I lived in. I was in the thick of this new technology. The second inflection point. I jumped from the corner office with a little parachute to Silicon Valley (with three toddlers in tow). I landed with a thud eleven months later (during the great .com washout). My wealth on paper vanished overnight.
I washed ashore at AOL (which merged with Time Warner three days after I left to pursue the great start-up migration). I was fortunate to have a network that brought me back into the mix. I lived through seven years of the "AOL Time Warner" story that you all know. A lot of scars and learnings...but I did get to work with some of the smartest people of my career over those years (still a vibrant network to this day).
COVID is the third inflection point. It was not the typical slowly then suddenly impact of a technology advancing along; it was a "Full Stop" for everyone all at once (like the movie). It jarred all of us from "compartmentalizing our lives" into "sharing our lives like never before". All of those future-of-work companies that I worked for were racing to figure out how we would work again (not in the office), but in a distributed manner. A lot of people moved to a "dream location" or became a digital nomad. The reality is: we will never go back, regardless of the RTO demands. Hence, the social contract broke. The economics of people, work, and workflows changed. Human capital shifted to Human Capital Supply Chain (where an FTE is merely an option for a unit of work today, not THE unit of work). Note: I learned this concept working with a worktech company and the CEO - who saw this vision 20 years ago. Technology has now enabled it to be a reality.
I believe we are now in the fourth inflection point - AI. It, like the technology inflection points before it, will create winners and losers. I do believe the possibilities of AI will cut deep both ways - into good and bad outcomes. The fear will drive CEO's to make dramatic cuts because other CEO's do it and Wall Street rewards it.
I believe we need to reimagine our rewards and incentives for this new era. Behaviors follow the incentives. Rewards fall into two incentive camps: intrinsic vs. extrinsic motivations. The human race has toggled between those motivations forever. Companies have toggled between those motivations. Individuals (you and me) have wrestled with those motivations as part of our career and life choices. If I learned anything over my career, it is this simple concept. The entire gaming industry knows this...hence how and why you play the game. The social network companies know this - hence attention is the currency, and you are either the product (they control) or you pay for the product (you have majority control).
Trust. Certainty. Joy. I see these as key pillars going forward. Each is an individual choice and carries weight that only you can own. Consider your conditions, constraints, and environment. What do you control? What is man (person) made? Who do you trust? Nothing is certain, so how do you deal with uncertainty? How do you measure risk? And, ultimately, what brings you joy? What is the worth of joy to you?
I hope you will view this as a lived experience response and not a Dadsplaining post.
This is the best article I have read in a while.
Thanks Saloni, glad it landed with you!
Love this free agent concept!
I spent 12 years, then 5 years at companies doing executive support training people to use industry specific CRMs.
Then went out on my own as a copywriter (totally different skill set). The majority of my income has been from agencies. Very much a "free agent" feeling.
This last year I started looking for something more consistent. So I went back to looking for what I did for 17 years.
Nothing.
Even applied for jobs I was massively overqualified for and couldn't even get a response.
Job market feels crazy right now.
So I guess I just keep building my portfolio. Lol
You’re not alone Adam, the market is really strange right now. As companies figure out the new shape of the workforce in the world of AI, they’re moving in slow motion. It’s gonna get worse before it gets better. I believe everyone needs to embrace the free agent mindset.
executive support **and** training on CRMs.
Not "executive support training people"
2 different things. 😁
This is a great take and I feel like you just explained my recent situation. Your line "Work hard, deliver, and stay loyal. The company will do the same…so long as it’s in their best interest." seems to be a very outdated concept. I began with a startup, was offered phantom units for my early unpaid work, and earned a decent paycheck as a chief officer. But when times got tough, there were no cost of living increases. No bonuses. No anything. And a CEO who mismanaged money to a potentially criminal level. Luckily, I'm decided to start picking up new skills in the AI world about 12 months ago and was able to resign (before getting laid off) and have a job within minutes to cushion the fall while working to start up my own endeavor so that I'm not reliant on someone else in the future. Thank you for sharing your story.
Sorry you went through that, Todd. To your point, it’s outdated, but it’s the most defensible option a leader has when times are tough. “Fewer people, do more with less, save the company some money.” They believe if they do it that way, they’ll be saved. (Many are not). On the flip side, I hear Dana White go on Diary of a CEO and talks about a leadership style of leaning into the hard times and protecting his people. Both types of leaders get CEO titles. That’s the game. Appreciate you sharing your story here, thanks for investing the time.
This is a really good article. I think for people who have been impacted by lay offs, the hardest part is to allow ourselves to feel confident again to begin something new and on our own. People always go back to finding another job to a) get bills paid and b) feel that secure cushion again. When in reality, a job is more risky cushion than ever. Thanks for sharing!
It’s tough to build that confidence in the beginning, because you don’t have the usual guardrails to measure how you’re doing. In a job, you have targets, KPIs, QBRs, reviews…but on your own, nobody’s telling you if you’re doing a good job or not. Especially in those early days when you’re figuring it out and spending too much time doing all the wrong things. Thanks for reading and taking a minute to share your POV!
This framing describes exactly what I've been seeing and feeling over the last few years. As a fellow early 40s millennial with an 18 years career in various companies, I can see the split between those who are embracing AI and how to position themselves and others who continue to just show up.
Also there is this current narrative online that the w-2 job is a dead end and you must "burn the boats" and go all-in for yourself. I disagree and think many people are not cut out for building their own thing that will fully support them, and instead should take your Free Agent mentality to their career.
Couldn’t agree more, Judd - solopreneurship / entrepreneurship is not for everybody. It’s a hard road. I’m exhausted all the time. But staying in the W-2 job (which, also agree, is not a dead end) means staying in the system. And as long as you’re in the system, you’re at the mercy of its behaviors. So the ups and downs of rapid growth demanding crazy hours, the company plateauing, regressing downsizing, RIF’s/layoffs, finding something new (either before or after the axe falls), that’s your reality. It’s an acceptable life, as long as you’re accepting it with eyes wide open, knowing what it means.
Yeah it has its big downsides for sure. I think more people could do better at understanding them and optimizing to minimize the negatives while acknowledging and recognizing the positives.
Haha I write this after taking most of the day off because I feel ill. My wife is swamped in client work for her firm and just has to work around any sickness she encounters!
Looking forward to reading more of your work.
Cheers
Same here, man. Thanks for taking a minute to share your thoughts.
Being a free agent sounds good and having income outside your job is certainly appealing, but it's somewhat ignoring that the job takes up not only 40+ hours a week, but 40 of the best hours of the week. Where is the extra time coming from?
The truth most people don’t want to hear - you have to make them, you’ve gotta fucking scratch and claw for them. They’re small increments when you’re working a 40-hour-a-week (which is usually more for high performers in corporate). You wake up an hour earlier and work before the house wakes up. You stay up an hour late and shave off some of your sleep. You sit in the car at soccer games and write notes and go back and forth with Claude. You build in the margins of your already full life. The alternative is just accepting whatever that 40+ hour a week job gives you. Because nobody’s coming to build the thing for you, or me, or any of us. It’s on us. So we have to steal the time from somewhere else. Can’t do it from home life because you don’t want to implode your family. So you sacrifice something - sleep, TV time, whatever it takes. If you want the thing bad enough, you’ll make the time. You’ll start accepting really small progress as wins. You’ll learn to be more efficient with your time than you’ve ever been. It’s a process.
Great post Mike! Unfortunately this isn’t only happening in corporate America but globally x
Thanks Fran! I know, I have friends and former teammates all around the world, and it's impacting everyone. On the one hand, there's nowhere to hide. But on the other, we're all in this together, just trying to figure it out.
That’s right, we’re all trying to figure out what’s next xx
Keeping your head down and staying invisible leaves your career entirely at the mercy of internal spreadsheets. Building visible proof of your thinking gives you options before a sudden reorg forces your hand.
It's a little bit of insurance. I've also found untangling problems in public actually ends up helping other people, too. And you get help from unexpected sources. Assuming you're not violating your employment agreement, beyond being tired a lot, there's not much of a downside to building something of your own.
This is such a reality check kind of message. I am at the other end of your spectrum (an aged Boomer). I am a twin girl dad (32) and a father of a special-needs adult son (34). I have bridged the life you described as your parents, plus the new social contract of the next generations. I say my career has spanned three different epochs - corporate life to start-up life to solopreneur life.
I have evolved into designing narratives for corporations (as brand narratives), executives (two versions - complete transformation (ShiftStory) and Executive Sprint (CEO/Founder Narratives) as well as movements (reuse and rethink wine). I have worked with a 1/2 dozen or more future-of-work clients (people analytics, organizational intelligence, Outplacement, recruiting, TA, Presence Management, Organizational Network Analysis, AI-based versions of HR and WorkTech - all names you would know). I also guest lecture at leading universities, speaking with the next gen of hopeful talent.
As someone who is still a practitioner in the trenches, I see the fear and acknowledge that the great disruption is scrambling everyone's ability to navigate with an outdated compass. The reality I see is based on living through four significant inflection points. When I graduated in 1983, I was thrust into a "we only hire MBAs world". Inflation was insane (17%) and getting a job was as good as your ability to hustle and leverage your network. Cable TV and the beginnings of the software revolution were the emerging tech. The first inflection point.
Fast forward to the 90's and the great internet explosion happened. I was on the launch team of Pathfinder (at Time Inc). The writing was on the wall for the traditional media world I lived in. I was in the thick of this new technology. The second inflection point. I jumped from the corner office with a little parachute to Silicon Valley (with three toddlers in tow). I landed with a thud eleven months later (during the great .com washout). My wealth on paper vanished overnight.
I washed ashore at AOL (which merged with Time Warner three days after I left to pursue the great start-up migration). I was fortunate to have a network that brought me back into the mix. I lived through seven years of the "AOL Time Warner" story that you all know. A lot of scars and learnings...but I did get to work with some of the smartest people of my career over those years (still a vibrant network to this day).
COVID is the third inflection point. It was not the typical slowly then suddenly impact of a technology advancing along; it was a "Full Stop" for everyone all at once (like the movie). It jarred all of us from "compartmentalizing our lives" into "sharing our lives like never before". All of those future-of-work companies that I worked for were racing to figure out how we would work again (not in the office), but in a distributed manner. A lot of people moved to a "dream location" or became a digital nomad. The reality is: we will never go back, regardless of the RTO demands. Hence, the social contract broke. The economics of people, work, and workflows changed. Human capital shifted to Human Capital Supply Chain (where an FTE is merely an option for a unit of work today, not THE unit of work). Note: I learned this concept working with a worktech company and the CEO - who saw this vision 20 years ago. Technology has now enabled it to be a reality.
I believe we are now in the fourth inflection point - AI. It, like the technology inflection points before it, will create winners and losers. I do believe the possibilities of AI will cut deep both ways - into good and bad outcomes. The fear will drive CEO's to make dramatic cuts because other CEO's do it and Wall Street rewards it.
I believe we need to reimagine our rewards and incentives for this new era. Behaviors follow the incentives. Rewards fall into two incentive camps: intrinsic vs. extrinsic motivations. The human race has toggled between those motivations forever. Companies have toggled between those motivations. Individuals (you and me) have wrestled with those motivations as part of our career and life choices. If I learned anything over my career, it is this simple concept. The entire gaming industry knows this...hence how and why you play the game. The social network companies know this - hence attention is the currency, and you are either the product (they control) or you pay for the product (you have majority control).
Trust. Certainty. Joy. I see these as key pillars going forward. Each is an individual choice and carries weight that only you can own. Consider your conditions, constraints, and environment. What do you control? What is man (person) made? Who do you trust? Nothing is certain, so how do you deal with uncertainty? How do you measure risk? And, ultimately, what brings you joy? What is the worth of joy to you?
I hope you will view this as a lived experience response and not a Dadsplaining post.