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.

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