Midlife Crises & Changing Work: Gen-X, Once Again, Must Adapt to Survive

Midlife crises during a pandemic are no picnic. Neither is returning to a workplace that has forever changed.

These days, I’m being more intentional about trimming the weeds out of my inbox. Too many emails is tantamount to too much noise, and when its noisy, the voices actually I want to hear are drowned out by the others.

The ones I want to hear are those who help me on my quest for meaning, purpose, and the unseen truth.

There are a lot of really interesting email newsletters out there, and these are the gems I’ve sought to rescue from the email swamp. If you make space for them, you’ll find that they can help to refocus your thinking in delightful ways. Speaking of, have you subscribed to The Skojec File yet? It’s only $5 a month, and its more satisfying than a…Taco Bell Cravings Box…which according to the internet is also $5.

Today, my train of thought began with one of these newsletters. It’s called Further, and it’s a “weekly email with the top hand-picked health, wealth, and personal growth advice for people in their 40s and 50s.” The headline of the piece — “Welcome to Your Multistage Career” — was interesting, and I want to come back to it in a minute, but it was the first sentence of the piece that really grabbed me: “What a time to be at midlife, right?”

Ain’t that the truth.

The Not-So-Mythical Midlife Crisis

I’ve been thinking a lot about this lately. It’s pretty safe to say I’m at least hip deep in my own midlife crisis, which undoubtedly has fueled my recent, more deeply inquisitive mission to uncover truth, even if I have to look in places I wasn’t comfortable with before. The motivation for this is a multifaceted thing, but one of the primary catalysts is a deep sense of dissatisfaction with the way things are, the way I’ve done them, and so much that I have taken for granted as true or unavoidable without ever having really thought it through.

As I mentioned in my first piece about fulfillment, I had reached a point where I was more “successful,” in conventional terms, than I’d ever been before, but I was no longer deriving fulfilment from it, and was instead quite miserable. Some of this was undoubtedly due to my own bad habits, and how these damaged my relationships with loved ones. But some of it was connected to a deep sense that everything I was doing was repetitive and pointless.

In a piece at Aeon, Kieran Setiya, a professor of philosophy at MIT, zeroes in on this phenomenon when he eloquently and succinctly describes the mid-life crisis as “an emptiness in the pursuit of worthy goals.”

He paints a picture of his own success as an academic, the busyness of his life, and also the “sense of repetition and futility of projects completed just to be replaced by more. I would finish this article, teach this class, and then I would do it all again.”

There are certainly times when the thought comes, oppressive and daunting, that even the things I truly enjoy, like writing, will become perpetual necessities that will bleed me dry, demanding a bottomless well of creativity and production I’m not capable of delivering on, stretching out for the rest of my days.

Setiya does not sugarcoat the paradox we face:

Life needs direction: desires, projects, goals that are so far unachieved. And yet this, too, is fatal. Because wanting what you do not have is suffering. In staving off the void by finding things to do, you have condemned yourself to misery. Life ‘swings like a pendulum to and fro between pain and boredom, and these two are in fact its ultimate constituents’.

He continues, probing insightfully into the mysterious trap we seem to have found ourselves in:

Taking up new projects, after all, simply obscures the problem. When you aim at a future goal, satisfaction is deferred: success has yet to come. But the moment you succeed, your achievement is in the past. Meanwhile, your engagement with projects subverts itself. In pursuing a goal, you either fail or, in succeeding, end its power to guide your life. No doubt you can formulate other plans. The problem is not that you will run out of projects (the aimless state of Schopenhauer’s boredom), it’s that your way of engaging with the ones that matter most to you is by trying to complete them and thus expel them from your life. When you pursue a goal, you exhaust your interaction with something good, as if you were to make friends for the sake of saying goodbye.

Hence one common figure of the midlife crisis: the striving high-achiever, obsessed with getting things done, who is haunted by the hollowness of everyday life. When you are obsessed with projects, ceaselessly replacing old with new, satisfaction is always in the future. Or the past. It is mortgaged, then archived, but never possessed. In pursuing goals, you aim at outcomes that preclude the possibility of that pursuit, extinguishing the sparks of meaning in your life.

So what are we to do?

Setiya says that we “need to draw distinctions among the activities we value: between ones that aim at completion, and ones that don’t”:

Adapting terminology from linguistics, we can say that ‘telic’ activities – from ‘telos’, the Greek word for purpose – are ones that aim at terminal states of completion and exhaustion. You teach a class, get married, start a family, earn a raise. Not all activities are like this, however. Others are ‘atelic’: there is no point of termination at which they aim, or final state in which they have been achieved and there is no more to do. Think of listening to music, parenting, or spending time with friends. They are things you can stop doing, but you cannot finish or complete them. Their temporality is not that of a project with an ultimate goal, but of a limitless process.

If the crisis diagnosed by Schopenhauer turns on excessive investment in projects, then the solution is to invest more fully in the process, giving meaning to your life through activities that have no terminal point: since they cannot be completed, your engagement with them is not exhaustive. It will not subvert itself. Nor does it invite the sense of frustration that Schopenhauer scorns in unsatisfied desire – the sense of being at a distance from one’s goal, so that fulfilment is always in the future or the past.

Investing more fully in the process sounds a great deal like what we discovered in the second part of the series on fulfilment. Remember this, from Cortland Dahl?

Over the past few decades, a growing body of scientific research has shown that we may be looking in the wrong places to find meaning and purpose. The picture that is emerging from all this research suggests that having a sense of purpose is not something that we only discover when we are free from our struggles and the mundane details of life. To the contrary, purpose is precisely what helps us deal with adversity. It gives us the strength to persevere when we start to lose hope, and to find meaning in the seemingly meaningless details of our daily routines.

It’s a particularly lousy time to be working through a midlife crisis. The Pandemic and Politics have been the twin pillars of an unusual amount of societal madness over the past year, and trying to re-discover meaning in the middle of this massive wave of surrealism and displacement is even harder than it might otherwise be.

And yet, these are the cards we were dealt. Even if it weren’t for the suspension of life as we knew it and all the ripple effects that has caused, we were already looking at a very different landscape moving forward for those of us who still have more practical things — like jobs — to worry about.

The Workplace Was Already Changing - Now It’ll Never Be The Same

The debate is ongoing about just how many people, having become accustomed to working from home since the pandemic began, will actually be returning to their offices. Companies like Google, Amazon, and Goldman Sachs have indicated that they absolutely intend to return to, as Amazon put it, “An office-centric culture.”

But however this shakes out, the workplace was already transforming, as James Altucher wrote compellingly about in his 2013 book, Choose Yourself!. Altucher tells the story of a big time New York investor whose office was in a skyscraper in New York City, surrounded by windows:

He brought me over to one of them. “What do you see?” he said. I don’t know, I thought. Buildings. “Empty floors!” he said. “Look at that one. Some bank. All empty.” He pointed at another building. His fingers scraping across his window like…I don’t know…whatever a spider uses to weave its web. “And that one: an ad agency or a law firm or an accounting firm. Look at all the empty desks. They used to be full, with full-time employees. Now they’re empty and they will never fill up again.”

I spoke with several CEOs around that time and asked them point-blank, “Did you fire people simply because this [the 2008 economic crisis] was a good excuse to get rid of the people who were no longer useful?”

Universally, the response was a nervous laugh and a “Yeah, I guess that’s right!”

And because of the constant economic uncertainty, they told me, they are never going to hire those people again.

All those spaces. All that office space. All those jobs. Gone, because everything is changing. That’s not necessarily a bad thing, but we’re going to have to adapt. Altucher continues:

ZERO sectors in the economy are moving toward more full-time workers. Everything is either being cut back, moved toward outsourcing out of the country, or hiring temp workers. And this goes not just for low-paid industrial workers, but middle managers, computer programmers, programmers, accountants, lawyers, and even senior executives.


Across every industry, technology has replaced not only paper (“the paperless office”), but people. Companies simply don’t need the same amount of people anymore to be as productive as they’ve always been. We are moving toward a society without employees. It’s not here yet. But it will be. And that’s okay. We’re already seeing more startups than ever get funded, get customers, and pull business from the corporate monoliths, which have slept for too long. This isn’t just about money, though. If it were, it would be boring. It’s also not about being a great entrepreneur. I’m an entrepreneur, a writer, and an investor. Not everyone is an entrepreneur. Not everyone wants to be one.

This is about a new phase in history where art, science, business, and spirit will join together, both externally and internally, in the pursuit of true wealth. It’s a phase where ideas are more important than people and everyone will have to choose themselves for happiness, just like I did.


You no longer have to wait for the gods of corporate America, or universities, or media, or investors, to come down from the clouds and choose you for success. In every single industry, the middleman is being taken out of the picture, causing more disruption in employment but also greater efficiencies and more opportunities for unique ideas to generate real wealth. You can develop those ideas, execute on them, and choose yourself for success.

Brian Clark, in his “Multistage Career” piece I mentioned at the top of this post, comes out of the gate swinging on the inevitability of turmoil facing Gen X on the career front. Like Altucher, he touches on the technological shift, but he also focuses on changing career-length expectations:

We’re facing a big double whammy of change — emerging technology that will shake up the very concept of traditional employment, plus the prospect of a work life that will likely stretch well into our 70s.

That’s the topic of The New Long Life: A Framework for Flourishing in a Changing World, by Andrew Scott and Lynda Gratton. An economist and psychologist, respectively, Scott and Gratton argue that the twin realities of radical new technology and extended longevity will require both personal adaptability and a re-working of society.

All of this is leading us to a re-evaluation of work-as-we-knew-it:

While our generation has never had the luxury of the status quo remaining in place, we’ve been conditioned to think of life as three stages — school, career, retirement. Now in our 40s and 50s, we’ll need to adapt to a multistage work life that will be more fluid as technology constantly eliminates tasks and entire jobs.

Add to that a longer work life (and life in general), and your career is going to start looking more like a series of projects than a standard career arc. If anyone can adapt, it’s us … but we need to be clear eyed about what’s coming.

I wonder how many people my age have already been experiencing this.

I graduated from college 20 years ago next month. It’s hard to believe it’s been that long. When I look back over my career — if you could call such a disjointed string of jobs a career — it was a crazy, erratic ride. I went from one workplace to another, sometimes switching positions in as little as six months, working temp jobs during lulls, dabbling in many different things trying to find my path. In just my first four years out of college, I worked in a call center, as a content jockey at a management consultancy, an art production assistant, a government technology bid analyst, a temp receptionist, an administrative assistant, a Humvee desert tour guide, and a Realtor.

I remember more than one interview where I faced puzzlement from the interviewer, usually with at least 20 years on me, looking over their glasses at my choppy resume.

“Why do you move around so much? You’re not staying at any of your jobs for very long.”

It wasn’t as though I could simply tell them, “Because work is nothing but a commercial transaction, there’s little to nothing available in my field, and I’m looking for the best options for me. I am essentially a mercenary. I sell my skills to those willing to pay the requisite coin, and many of my previous employers were not. Worse, they underutilized my abilities.”

I was under no illusion that this corporate fidelity they searched for in vain on my CV was going to be returned if they were displeased with my work. Loyalty was not a two way street, we both knew it, and the expectation of it chafed as I went begging, hat in hand, for a job. Little did I know that this job-hopping habit of mine, which was frowned upon just ten or fifteen years ago, would become fairly standard.

As the jobs I managed to land got better, my tenure did tend to get a bit longer. Instead of six months or a year I’d make it 3 years at a job before desperately reaching for the next rung of the ladder. It wasn’t until I started my own business that actually made use of most of my core skills that I watched the better part of a decade on the job whizz by in the blink of an eye.

Clark argues that the “entrepreneurial life is the path to greater economic security than a traditional job has provided for many decades.”

I agree. But I think an additional piece that’s essential for success, especially if you’re doing a mid-life career shift: actually liking what you do.

For me, success via entrepreneurship was less about my own entrepreneurial gifts (I don’t really have any) than about proper utilization: I didn’t get to do the work I was best at until I started working for myself.

In my twenties, I could put up with a lot more stuff I didn’t care for, or do work only tangentially related to my areas of skill and interest. The future was wide open, and I knew I was collecting know-how along the way.

But for those of us in our 40s and 50s, it’s a different story. We may not ever be able to quit working unless we learned to be wise investors — I did not, but my wife is trying to make up for my lack of foresight. So it’s possible we’ll never get to quit working. That said, we’ve got a cultivated skillset and known talents. Doing work that we find meaningful and enjoyable is critical to our long-term success.

In an essay at The Atlantic — 4 Rules For Identifying Your Life’s Work — social scientist Arthur C. Brooks tells the story of “The Marshmallow Experiment”:

In 1972, the Stanford University social psychologist Walter Mischel undertook a psychology experiment involving preschool kids and a bag of marshmallows. He would sit across the table from each child, take out a marshmallow, and ask, “Do you want it?” Obviously, they did. He told them it was theirs—but there was a catch. He was going to leave the room for 15 minutes. The child could eat the marshmallow while he was gone, if he or she wanted. But when the researcher came back in, if the first marshmallow was still there, the child would get a second one.

Mischel found that a majority of the kids couldn’t wait, and gobbled up the marshmallow when he left the room. He followed up on the children in the study, and found that those who were able to delay their gratification found greater success as they grew up: They were healthier, happier, and scored higher on their SATs than the kids who had eaten the marshmallow.

The upshot, Brooks says, is that “Good things come to those who wait—and work, and sacrifice, and maybe even suffer.” And so, he asks, when it comes to career satisfaction:

What exactly is your marshmallow? Do you know what you sacrificed and suffered for? Do you have a professional calling that is worth having deferred your consumption and gratification all these years?

Brooks lays out 4 rules for figuring out what your Marshmallow is. They are:

Rule 1. The work has to be the reward

Rule 2. An interesting career is better than a fun career.

Rule 3. A career doesn’t have to be a straight line.

Rule 4. Beware of unhealthy passions.

Space will not permit me to summarize his explanations in depth, so I hope you’ll head over and read the whole piece. But I want to zero in on a couple of things.

The first rule means, essentially, that if you’re working at a job because of the money or the prestige but not because you find meaning in the work, you’re probably going to be miserable. Doing a job you hate, even if it’s for better pay, is going to have diminishing returns before long. Doing a job you love, even if it doesn’t pay as well as you’d like, is much more likely to lead to financial success. Why? Because you’re going to be putting a lot of effort and care into it, not working just hard enough not to get fired.

But that brings me to the interesting distinction Brooks makes in Rule 2, which is one I haven’t heard before: some people prefer jobs they’d categorize as “fun” or “enjoyable”; others seek jobs they’d consider “meaningful.” But failing to find a balance of both will still diminish one’s sense of fulfilment in their work. “At the nexus of enjoyable and meaningful,” writes Brooks, “is interesting.

Interest is considered by many neuroscientists to be a positive primary emotion, processed in the limbic system of the brain. Something that truly interests you is intensely pleasurable; it also must have meaning in order to hold your interest. Thus, “Is this work deeply interesting to me?” is a helpful litmus test of whether a job could be or could lead to your marshmallow.

His fourth rule about avoiding “unhealthy passions” has to do with being too wrapped up in your work:

In 2003, Canadian researchers studied 900 people engaged in different activities about which they were passionate, including their jobs. Those with what they called “harmonious passion” for their activity experienced positive mood, good concentration, and a “flow state” while doing it. But they also felt fine when they weren’t engaged in the activity. In contrast, “obsessive passion,” while also characterized by intense interest, featured negative mood and poor concentration during the activity, as well as unhappiness when not engaged in the activity.

Work is kind of like romantic love in this way. Almost everyone reading these words has had an unhealthy relationship or two. What many unhealthy relationships have in common is obsessive passion: a need to be together, but unhappily so. Obsessive passion brings out the worst in us. In contrast, healthy relationships generate harmonious passion, characterized by happiness and mutual improvement as people.

I experienced this with 1P5: my work ended up eating its way into every area of my life. And because my work was about religion, going to church felt like work, too. Those were the conversations people would want to have with me after Mass, or at barbecues or cigar nights. The things I experienced at my parish or in my spiritual life became part of the work. And the crisis in the Church loomed over me day and night, with me feeling like I had to go all in to fight it. My boundaries were blurred.

My whole life, I’d been taught to prioritize God and my Catholic Faith above all else. When I worked other jobs, I felt like I was missing my true calling. When I made it my (more-than) full-time job, everything about it was imbued with this same sense of importance; and thus, it knocked everything else — including my family, in many important respects — off my plate. My dynamic with the Church lacked the requisite balance of a healthy relationship. But backing off meant feeling like I was falling short, too.

Re-focusing some of my efforts on other projects, like this one, has been a huge help. Pulling back from work fraught with those ideas and focusing on broader topics of interest feels almost like a vacation. For the first time in my life, I’m beginning to give myself enough time to work on things, even if it means other stuff gets dropped. I also am walking away from work when I need to, spending more time with my people, and getting more sleep. I likely wouldn’t have done any of this, though, if I hadn’t hit a personal wall. Sometimes, crises are catalysts in disguise.

Even without a big turning point, making changes like this sounds easy on the surface, but they aren’t. The confidence we might feel at the end of reading an article about how to make Big Things Happen tends to fizzle and fade as the familiar ebb and flow of our daily lives re-asserts itself. Old habits take over. Another dinner to make. Another project due at work. Another bill to pay. And the next thing we know, we’re doing the same old same old, going through that cycle Keiran Setiya described as “a sense of repetition and futility of projects completed, just to be replaced by more.”

We’ve got to short circuit our entrenched, repetitive thought patterns and behavior, and for that, we’re going to need a bit of mental kryptonite.

On the next installment, I’m going to dig into the growing body of information on “unlearning” - the process of getting rid of some of our old, limiting thoughts and beliefs to open the door for new information and perspectives. It’ll be interesting to see what we can discover.