Life After Quitting a Full-Time Job

Exactly two years ago today I quit my job. My work life since then has not been a roller coaster, an adventure, a disaster, a triumph, a barrel of laughs, or a bucket of tears. It is what it is: Change — necessary, gradual, the fabric of existence.

I quit, in part, to rediscover the joy and the mission of teaching, and I continue to work in publishing as a freelancer. It’s great to be back in the classroom, and I value the opportunity to keep my hand — and my brain — in the various editing and writing domains where I manage to find (usually stimulating) work for pay.

Since I quit, I’ve been blogging about that decision, about freelance life, and about various other topics that relate to working independently. With just a few exceptions, the most widely read of my posts continue to be those specifically about quitting. Around some of the early ones, a still-ongoing online conversation sprang up. Perhaps you’ve been a part of it and have had a chance, like me, to learn from the stories of people who decided to deliberately change course, sometimes for the worse but usually for the better.

Indeed, there’s a lot of psychic energy out there around issues of job frustration, “starting over” professionally, and remaking oneself. The search terms that people use to find my blog provide anecdotal evidence. Phrases like these pop up frequently on my WordPress dashboard: “quit and reinvent myself”; “can’t take this job anymore”; “talented and want to quit”; “must quit to be free”; “can I quit and become famous”; “how to quit and be successful”.

Then there are the rarer, even more revealing phrases: “want to quit wife won’t let me”; “if I quit will my kids eat”; “leave this job and conquer the world”; “too talented to have a boss”; and (my favorite) “my job sucks a fat gorilla”.

Perhaps these two sets of search terms don’t fairly represent the sensibilities of folks who desire to quit. Google can, for some who are alone in a cubicle at work or on a laptop in bed late at night, serve as a therapist’s office or a confessional booth, where emotions are expressed raw and in rare form. But even in contexts that are not anonymous and impulsive, I have met recent and would-be quitters who express sentiments similar to those shared with the mighty search engine. To many, quitting seems like a ticket to liberation — an American dream of bursting forth by tearing down the fence that cages you in, in ironic contrast with the type you build with white pickets. In the spooky world of the American dream lurk the strangest contradictions.

There are, of course, a few folks for whom quitting is the ticket to great, previously unimagined material and spiritual success. But nearly always, life just doesn’t work that way. Quitting may be the right thing to do in a given set of circumstances, as it was for me. So my tepidness is not meant to sound like an endorsement of inaction. But if when you think about quitting, you find yourself intoxicated by the fantasy of your own uniqueness or by the delusion of your manifest destiny, do yourself a favor: Take a deep breath (and at least a few weeks, maybe months) before you do something rash.

After all, change borne of anger or euphoria is likely to deliver a sting — and to leave you no better off than you were before. The best kind of transition is the mundane sort that isn’t fully palpable while it’s happening, but only in retrospect. Change that feels heady is more likely to end with a letdown, perhaps a sobering realization that the opportunity you thought you’d grabbed by the throat was never even real.

Gee, what a wet rag to throw on this sexy topic of quitting your job! Maybe so. I don’t mean to say that life-altering career decisions don’t have moments of inspiration. They undoubtedly do, and I have written about my own. But what I read and hear so often in discussions about whether someone should quit a job are silly promises about uncharted waters on the one hand and dire warnings not to rock the boat on the other. There’s nothing more likely to cause seasickness than a ship of fools. Don’t listen to the yammering crew or, worse, become one of them.

With that strained metaphor, I take my leave of this topic of quitting a job. I’ve said all I have to say about it, at least in blog-post form. I’ll continue to write about the other topics that have been featured here and will probably add new ones that change the direction of this self-indulgent little enterprise. I’m not sure precisely where I may digress, but ideas are brewing. “Working for Yourself” is ready to boil off its excess.

For those interested in the history of the now two-year-old “Quitting a Job” subseries in this blog (which was born on HBR.org), here is a list of all the posts on that topic, in chronological order. Have a happy troll through the archive, if you’re so inclined. Regardless, I hope to hear from you on other topics in the near future. And, of course, feel free to offer some final thoughts and stories about quitting.

I Just Quit My Job. Am I Crazy?

Leaving Your Job in Tough Times: Swim, Sink, Swim

When Not to Quit Your Job

Quiz: Does Your Work Matter to You?

How Are You Coping with Uncertainty?

How to Quit Your Job with Style

Don’t Quit the Way Sarah Palin Did

Was Quitting My Job the Right Decision?

The Quitter’s Playlist

You’ve Quit Your Job. Now What?

Going Solo: One Year Later

A Career — and Now a Blog — in Transition

So You Want to Quit Your Job and “Start Over”?

Why Talented People Quit

Does Quitting Your Job Seem Sexy?

Quitting a Job: An Act of . . . Poetry?

When Focus Becomes Monotony

Where Freelancing Meets Independence

People who work for themselves often cite independence as the most appealing element of their work lives. They praise the flexible schedule, the lack of a boss, and the ability to select the work they do. I certainly value those concrete benefits, but what matters to me more is the freedom to assess quality as I see it, without the burden of internal politics or the sometimes senseless rules, both written and unwritten, of organizational culture. Despite not being bound by those strictures, some freelancers censor themselves, fearing to tread into territory that might displease a client. But that usually diminishes the value of their own work and denies them the sense of satisfaction that only calling things on the merits can provide.

Merits are relative, to be sure, especially in the worlds of editing and writing, where I spend about half my work life. But people with keen, analytical minds who try to honestly assess everything they encounter usually end up agreeing quite a lot with one another about what the merits are — even if it takes a lot of debate and deliberation, not all of it pleasant, to get there. Some organizations have managed to make room for this kind of honesty internally, but they are relatively rare.

Much more often, I have found, work environments function in one of two ways: a moaning and groaning culture, in which people routinely make things more burdensome than they need to be, or an “everything’s great” culture, in which people are pathologically positive and reflexively ignore flaws in the interest of preserving equanimity. Of course, most workplaces have a mix of those characteristics, in part because of the diversity of personalities, work styles, and subcultures in any one institution. But I must say that I have very rarely encountered a workplace climate that simultaneously (1) challenged chronic complainers directly on the substance of their exaggerations and (2) unmasked the type of self-censoring, Stepford Wives–style optimism that, by tacit agreement, keeps everyone creepily content and uncritical. Fear, self-interest, and willful ignorance are usually what entrench these mind-sets, but brute force is not the way to break their strangleholds. Dispassionate leadership-by-example does a much better job, though that can be hard to execute when you’re on the outside.

If you happen to be pretty good at influencing insiders, the outside perspective that freelancing enables still does not entitle you to preside like a robed judge over poor petitioners who seek your counsel, even if you’re explicitly being paid as a consultant. Loftiness is not what this freedom is about. Quite the contrary, it’s about allowing yourself to explore and question with the enthusiasm of a curious scientist, then negotiate the practical value of what you find with the deftness of a skilled diplomat. It’s, in short, the thrill of discovery and the craft of persuasion all wrapped into one. But plainspoken critique is sometimes required, and, yes, that could cause you to lose a client.

In my work life, an independent point of view is what I’ve always valued more than anything else, whether that perspective is mine or that of the people with whom I collaborate. Freelancing has allowed me a bit more breathing room as I try to do the best job of this that I can. And, frankly, it has given me the wherewithal to do some of my own writing, this blog included. Finding time for such independent expression still remains a huge challenge, especially for someone like me who struggles with saying no to people. But independence of mind is, after all, more about space than it is about time. And there’s more of that on the outside than there is within one institution’s four walls.

When Focus Becomes Monotony

I’m lucky to have a long attention span — to be able to concentrate for many hours on one task without being distracted. What makes me bored is not working for too long a stretch but rather, over the course of months or years, discovering that all of the things I’m doing serve the same mission. That realization was one of the factors in my decision to leave my full-time job in late 2008.

In some sense, despite my long attention span, I have become a multitasker. Not of the sort who does many things in the same moment, but the kind who craves a diversity of purpose. I feel an acute need to spend my time in a wide variety of domains yet to inhabit each with singular intensity. This kind of multitasking is best understood not in the usual way, as simultaneity, but rather as multidimensionality. It’s spatial rather than temporal.

Case in point. I spend a significant portion of my work life teaching adult immigrants. I believe in what I’m doing, and I feel that in the classroom every day. Yet, as both a math teacher and an English teacher, I must be flexible enough to differ in those two roles, approaching each in the way that the specific merits of the discipline — and the particular needs of the students — demand. In effect, I have two main missions within my role as a teacher, and many smaller missions within those.

But that isn’t enough for me. I do freelance writing and editing in an array of disciplines (business, medicine, the humanities, and others). In each one, I become what the discipline asks of me — on its own terms. And I play different editorial and authorial roles within the various domains. When I contemplate my work identity, I feel like a dodecahedron, and I’m happy to be one. My need for this many-sidedness is fundamental. Without it, I would become flat and voiceless — the thin skin of a drum without its deep barrel.

Some wonder, of course, whether I actually needed to quit my full-time job to achieve multidimensionality. People, some calling themselves researchers, now instead advocate transforming the job you have into the one you want. Sure, that’s better than making no change at all. But if the different niches you manage to carve for yourself within your present job ultimately have you serving the same mission, corporate or otherwise, are you just doctoring your perceptions about your work life or actually changing your reality? A loaf of bread looks different if you reshape the dough — but it’s still a loaf of bread.

That said, each person must grapple with these questions of self-fulfillment in his or her own way. My own conclusions might be wildly off base for someone else. The key is to make sure you’re reflecting on your situation honestly, not navigating a conveniently circuitous path to a foregone conclusion. Only you can make the assessment. If someone else (like me) does, you probably won’t buy it.

If in the end you do decide that serving one mission simply isn’t enough, the practical obstacles to change are enormous, unfortunately. The U.S. economy isn’t set up to make diversity of purpose easy to achieve, at least when it comes to work. Health care, for starters, is not something to which we all have common access — split your time among employers and you usually pay through the nose. It’s dangerously easy, therefore, for freelancers and others who diversify their obligations to slip into the trap of becoming mercenaries, who by definition don’t have a mission other than to earn money. That’s where the line between multidimensionality and fragmentation starts to blur. The former is whole; the latter is a mess.

Still, monotony that masquerades as focus is a frightening prospect to me, despite the risks inherent in trying to avoid it. For now, my long attention span and my acute need for diversity are managing to coexist comfortably. The drumbeat of my heart remains steady. If it starts to flutter, I’ll let you know.

Quitting a Job: An Act of . . . Poetry?

I’ve heard people say that quitting a job is having the courage to admit that work is not the most important thing in life. For some, that’s true — quitting can be about placing value on things other than earning a living or, more to the point, other than earning respect for earning a living in a certain way. In short, they resolve not to give work more of their time and energy than it truly deserves. It’s a perfectly legitimate point of view, and it leads many to make decisions that improve their lives greatly. These practical choices are acts of necessity.

For other people, the need to quit a job emerges from a deeply held belief that work really matters — matters too much to be done in the ways that the institutions they inhabit at the moment demand. They find it hard to watch the potential of human labor — especially their own — strangled by narrow aims that don’t amount to much in the end. These folks, who are often the most talented, don’t merely redefine their priorities and slot work in the proper place. They seek to redefine work itself and to restructure their “working selves,” not just their work schedules, accordingly. Their decisions are acts of conviction.

Whatever the reason someone quits, quitting is indeed an act. Even the most level-headed, drama-free exit from a job (the best kind) puts a person in a contemplative zone, not so much as the decision is being made but in the aftermath — in that curious, breathless void that only big transitions expose. It’s then, just as the lungs begin to fill anew, that it’s most valuable to give yourself the room to speak. That speech can take many forms, not all of them verbal. But I believe it’s important to articulate something while you’re in that space, to loosen the ties around the neck, some of which you may not even have felt before the untying. There’s something about the gesture — about the expressive act itself — that allows you to stretch and grow more fully than you would have otherwise.

For me, that act was writing a blog post about my decision to quit, and then the subsequent serial blog that, by twist of fortune, ensued on hbr.org and now resides here. A much more compelling act on the subject is an evocative poem by the late Robin Blaser, called simply “Quitting a Job.” You can watch and listen to him read it at an event in late 2008, just six months before his death and, strangely, just one week after I decided to quit, by clicking here (start at 17:50).

It’s in witnessing acts like Blaser’s that, I believe, you can begin to discover the poetry of your own act — to hear in your mind’s ear, and then articulate, the voice of what’s possible so that, as Blaser writes so pointedly, “You won’t die strangled.”

Thanks to Cheryl Clark Vermeulen, who introduced me to Blaser’s poem.

I Ain’t the Boss of Me

I don’t have a home office. There’s no room or cordoned-off area where I retreat to do my work, prepare my invoices, and rule over my freelance roost. Technically, I’m called a “sole proprietor,” yet I own almost nothing that’s exclusively work-related. Sure, I have a laptop, but it migrates from room to room, even sometimes from town to town, as I piece together my living.

Freelancers vary, of course, in how they define the boundaries of their work spaces, both physically and psychologically. On the opposite end of the spectrum from me is my soon-to-be landlord. I recently went to his home office to sign a lease on a new apartment. His professional domain was a mini-empire, with all the machines, tools, shelves, cabinets, and other trappings that make a freelance entrepreneur feel like the king of his castle. Sure, the dividing line between professional and personal was not absolute (his wife was changing the baby’s diaper mere steps away), but this man made clear that he enjoys lording over his territory. If I hadn’t seen his infant son pee in his wife’s face with my own eyes, I might have assumed the odor of urine was from the father’s scent-marking. In short, he is a businessman, and I am his client.

In my relationships with the people who pay me, “clients” is definitely the wrong word. What I do for them feels like work I took home from the office, not tasks I am “contracted” to perform. I treat these folks like colleagues rather than customers, whether or not I have previously worked with them face-to-face. There’s some risk in that approach in the short run, but in the long run everyone wins.

My non-proprietary attitude, odd as it may strike you, is also essential to my psychological well-being as a freelancer. You see, I’m really a full-timer in my soul, in the sense that I prefer an elbow-rubbing informality as I collaborate with people and create things of value. Overly prescribed professional niceties tend to inhibit my work. And a rigid proprietor/customer mind-set gets in the way of producing high-quality results, at least in editing and writing, where the bulk of my freelance activities lie.

So why in the world did I quit my full-time publishing job a year and a half ago if I’m not really a freelancer at heart? Without rehashing my many blog posts on the subject, I would boil it down to a desire to feel unencumbered in a variety of domains, not just one. I teach English and math part-time, for example, and I need the dynamism of the classroom and the give-and-take I get from fellow educators to sustain me. Yet I also want to have the time and the opportunity to be stimulated by an array of professional activities in publishing, where my impact is much less immediate but where I feel connected, albeit indirectly, to larger audiences.

Where that leaves me as a freelancer, though, is without a single domain that I can claim as mine. I have no urge to hang out my shingle, lay down a welcome mat, and fill a little plastic rack with crisp business cards. I don’t even want to be my own boss. Indeed, I’ve come to accept that my bosses are many — but they don’t own me either. Ownership, in the business sense, is not what I’m after, no matter who holds the purse strings. My professional philosophy is strongly independent, yet my day-to-day actions quietly serve others, and that in turn serves me.

Territories are hard to mark on this sort of landscape, and that may seem frustrating to those who prefer to know precisely where they stand in the professional world. I guess I’m more interested in the topography.

Why Talented People Quit

What you can learn from Senator Evan Bayh’s decision not to seek re-election

Since I quit my full-time job in late 2008, I’ve found myself in many ad hoc conversations about the pros and cons of quitting, very few them initiated by me. I’m still amazed by the number of people whose brains are bubbling with a strong desire to quit — and who, at times, need to let it burst out for someone willing to lend an ear. Not surprisingly, dissatisfaction of one sort or another is usually at the root of an urge to quit. I’m most intrigued by the folks who are exceptionally good at their jobs but are still dissatisfied enough to want to bolt.

Talented people tend to be bothered by an inability to effect change, at least in a tangible enough way that their day-to-day jobs feel rewarding. The nature of the desired reward varies considerably, from making a real difference within the walls of the organization to witnessing the greater social influence of the work. Whatever the scope of their mission, many of these quit-minded people have a clear vision and good leadership skills but find themselves confronted with institutional obstacles, often in the workplace culture, that can’t be surmounted within a reasonable time frame. So the personal choice becomes: Get out now, or run the risk of languishing so long that I end up internalizing and reinforcing the culture.

A scenario like that recently played out in the U.S. Senate with Evan Bayh’s announcement that he would not seek re-election. Bayh is a former two-term governor of Indiana whose leadership skills are obvious to anyone who has followed his career and, by all accounts, to those who know him personally. Yet in the face of now much-discussed institutional and cultural obstacles in the Senate, Bayh says he found himself unable to make enough of a daily difference in people’s lives to justify another six-year term. Whatever your view of Bayh’s politics, the authenticity of his statements on this point, both written and in interviews, is clear. You can hear it plainly in his recent conversation with Charlie Rose (start at minute 16).

Despite the peculiarities of the U.S. Senate, Bayh’s personal dilemma seems remarkably universal to me. Institutional progress is necessarily slow, but sometimes too slow for talented people to withstand. A particular high performer might have the skills to lead change but hasn’t yet reached a leadership position, as Bayh (in only his second Senate term) has not. And leading without authority, though possible in the right context, has very real limits. Probably too many limits for someone who’s already governed a state, or even for someone who has previously led effectively on a much smaller scale. For many talented would-be quitters, there’s comfort to be found in Bayh’s example.

The senator’s situation also offers a useful reminder about the best way, if you do decide to leave an institution, to make your decision known — namely, with grace, equanimity, and an eye toward the future. That doesn’t necessarily mean having another job lined up (Bayh doesn’t at this juncture, and I didn’t when I quit). But it does mean appreciating the continuity between one chapter of your life and the next, as I’ve discussed in “How to Quit Your Job with Style” and other posts. Feeling centered in that way makes the grace part easier. Of course, even with a bright future in sight, the temptation to grandstand can still be strong — witness Sarah Palin’s resignation from the governorship of Alaska. In short, if you find you can’t explain your decision to other people without sounding confused, beleaguered, or vengeful, you may not be ready to take the plunge.

That all said, there’s no credible rulebook for how to quit the right way. You’ll find information out there that masquerades as “research,” even with the names of revered institutions attached to it. But besides reflecting honestly on your own situation (that’s the vital piece), the best you can probably do is to read about and observe others who have thought critically about their own dilemmas. Tips can be a tyranny, as I (a sometimes tip writer) have admitted. It’s the indirect stuff — what you glean intuitively from the space between the lines of explicit advice — that offers the best guidance. In that respect, Evan Bayh’s account is just one point of departure. Listen to his story, between the words, and give yourself a chance to brew before you bubble over.

So You Want to Quit Your Job and “Start Over”?

In the fall of 2008, soon after the global financial crisis took hold, I quit my full-time job, returned part-time to teaching, and started editing and writing on a freelance basis. The decision was the right one for me for a variety of reasons, and I’m very happy to be back in the classroom. But the move wasn’t the wildly liberating rebirth that people often assume a voluntary career transition to be. It simply marked a new phase in a continuous personal evolution. No fireworks went off. No balloons soared. I didn’t speak in tongues.

That humdrum reality is at odds with a template in the American psyche about the nature of self-renewal. Its features include casting off the shackles of the past, reinventing yourself, and realizing a full potential that only “starting over” supposedly permits. The deceptive allure of Jay Gatsby’s “orgastic future” is alive and well 85 years after F. Scott Fitzgerald’s novel was published.

The American corporate workplace is the perfect breeding ground for this fantasy, with its almost pathological preoccupation with invention and innovation as metaphors for progress. Don’t get me wrong, these concepts are extremely useful when it comes to developing products and services, as the history of business proves in spades. But their psychological reach extends far beyond the domains where they have practical value. Indeed, the conceptual power of invention and innovation has been swallowed whole by many people who, naturally, feel the itch to change their lives from time to time, whether professionally or personally.

It’s just plain misguided to view that itch as evidence of a fundamental product flaw that requires you, as self-engineer, to go back to the drawing board and come up with a new design. Nor is it a malady in need of a cure or an evil from which to seek deliverance. The itch simply comes with having skin and flesh and blood and bone. As you walk through the world and its underbrush, you’re bound to get thorns in your side. No need to undergo a major surgical procedure to extract them — or to self-righteously cast blame elsewhere for being pricked. Save the stinging resignation sermon for the pulpit in your head.

Yes, I feel a bit uncomfortable when I listen to folks evangelize about reinventing themselves by quitting a job — or when they ask me to evangelize about my own quitting experience. It’s not that I get offended (I rarely do about anything), but I can’t help but be disturbed when I witness people playing tricks on their own minds, perhaps because I have done it myself. As I’ve written before, hyperbole about new-found freedom gets old fast, setting you up for a big letdown or even a crash and burn.

But perhaps this, too, sounds like evangelizing — by someone who’s written one too many blog posts about quitting a job. Call me a hypocrite. I won’t be offended.