Don’t Quit Your Day Job 
Take risks, ignore the doubters, and prove the haters wrong.
Fun fact: You wouldn’t be reading this persuasive ode to personal empowerment if I had not actually quit my actual day job a couple of years ago. I know—so meta you can hardly stand it, right? Samesies. But it’s true, and it’s a positively textbook example of the knowledge I’m about to drop.
However, the story behind that Big Life Decision is one I’ve already told twice in two books, focusing first on why I quit (to give fewer, better fucks) and second on how I quit (by getting my shit together). So if you want to read about those aspects of my “personal journey”—and yes, I just threw up in my mouth as I typed those words—you know where to find ’em.
What I’m exploring here is a little different. I want to talk about taking risks, whether or not they are specifically related to your employment situation.
Sure, you might hear “Don’t quit your day job” when you tell people you’re ditching your nine-to-five gig, pouring your meager savings into Mime College, and moving to Paris with only a beret and a dream (though you will emphatically NOT hear it from any mimes). But even if spooning with your employer-matched 401(k) keeps you sleeping peacefully at night, someday you’re liable to catch those five little words thrown at you, under different circumstances, by someone who feels the need to knock you down a peg.
Whatever the case—if you’re contemplating a big audition, a big purchase, or a big haircut—when Judgy McJudgerson sneers, scoffs, or jokes “Don’t quit your day job,” he’s really saying, “That sounds risky. I wouldn’t.” Perhaps with a subtle note of “I don’t believe in you, so you probably shouldn’t believe in you either.” (Or just “I don’t believe you have the cheekbones to pull that off.”)
Why Judgy gotta be like that?
Well, I’m going to hold back my slappin’ hand for a sec and give everyone’s favorite killjoy a smidge of leeway on this topic. Because although making snarky comments about other people’s life choices is frowned upon, the social contract is heavy on maintaining a shared sense of security—so if YOU start fucking around with norms and going off the grid of safe, sensible, conservative decision-making, where does that leave Judgy?
Afraid, that’s where.
And fear is a BITCH. (More on that later…)
Of course, watching people take risks can be exhilarating. Especially if it’s from the comfort and safety of your couch, as when I watched tightrope artist Nik Wallenda walk live over the Grand Canyon. He had a 6,000-foot-deep yawning chasm; I had a box of White Cheddar Cheez-Its. Exciting stuff. But sometimes—or at the same time—bearing witness to risk can be scary and unsettling. It begs one to imagine being in the other person’s shoes (in the case of Nik Wallenda, handmade, ankle-height, elkskin shoes), and one (like our pal Judgy) reacts by not only taking a big step away from the rim of the rock formation, but trying to drag you back with him.
So yeah, Judgy’s got some shit to deal with, and I don’t envy him for it. But just because he doesn’t like being too close to the edge doesn’t mean it’s no place for a nice girl like you to hang out.
And hey, risks aren’t just for Flying Wallendas—I have plenty of friends who look stable on résumés and bank statements but, on weekends, can be found with their head in a shark’s mouth or taking fire-eating classes. Even naturally risk-averse people like yours truly who stay the hell away from motorcycles and hot air balloons will someday be tempted by the road less traveled.
Taking it doesn’t have to be as scary as Judgy (or you) might think.
Risky business
You Do You is as much a self-help book as it is a postmortem on my own midlife renaissance,* which has involved taking a few big risks in the last few years.
In addition to exiting the rat race, starting my own business, and convincing a publisher I was capable of writing not one but three postmortems on my midlife renaissance disguised as self-help books, in 2016 my husband and I uprooted our entire life to move from Brooklyn, New York, to a tiny fishing village in the Dominican Republic.
And if you had told sixteen-or twenty-six-year-old me that thirty-six-year-old me would jettison not only a thriving career but also a lovely apartment and a stable, comfortable existence for a complete 180-degree turn toward a life of unknowns, adventure, and snakes in her roof*—she would have lobbied to have thirty-six-year-old me preemptively committed.
All of this is to say, I know a little something about risk, so if you feel like you’re ready to ditch your real or metaphorical day job, and if you’re looking for a wee push off of the cliff, it would be my pleasure to provide one. Metaphorically.
5 types of risks you could take and how to approach them
Changing your look: Shaving your head, getting a tattoo, going Goth, or just going blond—a makeover can be subtle or bold, and none of it has to be forever. Hair grows back, wardrobes can be retrofitted, and lasers are very sophisticated these days. So why not experiment? These are the best kinds of risks to take—fun and semipermanent. Barely counts at all, frankly. Risk level: Get thee to a tattoo parlor!
Auditioning for something: Whether it’s community theater or an internationally syndicated talent competition, the worst thing that can happen—after strutting your stuff under the watchful eye of Post Office Joan (who’s directing this year’s outer space–set Sweeney Todd) or warbling before your secret man crush Adam Levine—is that Joan or Adam tells you “Sorry, it’s a no from me.” So go polish up that monologue, get your octaves in order, and give it a shot. Risk level: Deep breaths.
Making a big purchase: If you have a bunch of bank in the tank, then buying a house or a car isn’t necessarily a risk; it’s just a thing you do every five to ten years. Congratulations, that’s a nice way to be able to go through life! But for most of us, deciding to use our limited resources to buy a big-ticket item or pay for grad school is more than a little daunting. These are upward-mobility risks. They could improve your life more, even, than a star turn in outer space–set Sweeney Todd, but the upfront cost is a lot greater than a case of the jitters. True, the scariest thing I ever did was sign my name to a mortgage, but I steeled my nerves with math. Figure out what you can afford, either in a lump sum or monthly loan payments, and don’t overextend yourself. Risk level: Calculated.
Wearing your heart on your sleeve: Are you itching to say those three little words? Maybe gearing up to get down on one knee? Or just hoping your cute study buddy will check the “Yes” box next to “Do you like me like me?” with a big, fat flourish? It may seem like a big deal in the moment, but look at it this way: In each case, the outcome is binary. I know, SUPER-ROMANTIC, SARAH. But she either loves you back, or she doesn’t. He’ll either say yes, or he won’t. One box will get checked and the other will remain as cold and empty as your bed on a winter’s night. Whatevs. The potential for heartache is real, but doing nothing just so you can’t possibly be disappointed is its own form of self-torture. Who are you, the Marquis de Sade? Risk level: Zeroes and ones.
Starting a side hustle: Totally intimidating, no arguments there. Booting up a new business—whether it’s web design or an Etsy store—can bring great reward or complete and utter failure, plus, potentially, a lot of useless candle-making equipment in your apartment. The key to getting anything like this up and running is a combination of strategy, focus, and commitment. I go over all of that stuff in Get Your Shit Together, but it comes AFTER you decide to start the business. In terms of taking the risk in the first place, I can tell you that fortuna audaces iuvat. That’s a Latin proverb that means it takes balls to make money. Risk level: Grow a pair.
And once you decide to take a risk (Bravo! I knew you had it in ya!), how do you keep walking the walk while other people are talking the shit-talk?
Top 3 ways to silence the haters
Fly under the radar: When my husband and I were planning our move to the DR, we told virtually no one. Why? Because we didn’t want to have to field questions, explain ourselves, or entertain naysayers. What other people don’t know won’t hurt them, and you won’t have to talk about it at brunch.
Screen your calls: If it’s not feasible to hide your risk under a bushel, you can limit your exposure to negative energy the same way I limit my exposure to street vendors, phishing scams, and telemarketers—don’t engage. If someone wants to pooh-pooh your life choices in person, make an excuse and walk away. (“Sorry, I’m late!” is a good one.) If they email you, don’t respond. And if they call you up, just “accidentally” switch off your ringer. Oops.
Clap back: If you’re feeling sassy, just say, “Thanks but no thanks for your unsolicited opinion. I’ll be sure to return the favor someday when you are on the verge of making a well-thought-out, nerve-wracking decision that you were nonetheless quite confident in before I opened my yap.”
Ultimately, if other people doubt your potential for greatness, that’s one thing. Other people can be kept in the dark, ignored, and put in their place.
But what do you do when the voices are coming from inside your own head?
I wish I knew how to quit you*
At fifteen years old, I tried to quit my summer job at a local surf and turf restaurant. I was really unhappy for a lot of reasons and it was the tail end of the season. I thought I could quit and at least enjoy my Labor Day weekend, far from buckets of dirty mop water and the scallop-scented fry batter that clung like barnacles to my Gap slacks.
I rehearsed my quitting speech only slightly fewer times than I rehearsed that TEDx talk I mentioned earlier, then mustered my cojones and went into the owner’s office to ask him to take me off the schedule.
Permanently.
When the four-minute conversation was over I was near tears and shaking with what I now recognize as panic but at the time felt like imminent death. To add insult to injury, my mother was waiting in the parking lot to pick me up from my shift. Heaving my cojones wordlessly into her minivan, I couldn’t bring myself to tell her right away what I’d done.
Somehow I instinctively felt as if quitting had been wrong, even though my reasons felt absolutely right.
The next morning, my boss called to inform my parents of my “rash” decision and asked them to intervene, saying I was too important to the successful operation of the restaurant to lose at this critical juncture. (Let me be clear: This is like saying that a single fifteen-year-old in the Zhengzhou factory is critical to Apple making its quarterly numbers.)
My boss knew that my presence or absence was not likely to alter the fate of his glorified-Applebee’s establishment during the dog days of August, but he also knew he could ruin the paltry remains of my summer by pulling “parent rank.” And given my anxiety-laced speech the night before, he probably also suspected that he’d be outing me before I’d had a chance to let Mom and Dad know I was not the future valedictorian they thought they’d raised, but rather a sniveling little quitter.
True, I wasn’t leaving for a better gig or more money. I wasn’t building a career in food service that necessitated a move up the ladder to Mike’s Clam Shack, nor had I been diagnosed with a severe shellfish allergy. (I also wasn’t feeding my family on my $2.30 an hour—it was just a summer job.) I simply wasn’t happy, and I didn’t want to show up. Another. Single. Fucking. Day.
But of course I went back, apron strings between my legs. Guilt and shame can be powerful motivators. Quitters never win, and all that.
Anyway, that whole incident set off a little audio loop in my brain that went something like: Quitting is a bad thing. It’s a personal failure. It’s not only a cultural no-no, but a rejection of the masochistic Puritan work ethic this country was built on, goddammit.
That voice piped up quite a few more times over the next twenty years, like when I worked at a bookstore where I was routinely derided by my manager, Wendy-Ann, for “being a know-it-all” (also known as “having read the books I was recommending to the customers”). But I had signed on during the fall rush—students at the nearby college bought their textbooks from this shop—so I kept my commitment even when I got a career-track offer to work for a prestigious literary agent. I pulled sixteen-hour weekends at the store while starting my new gig as an agent’s assistant during the week.
Wouldn’t want Wendy-Ann to think I was a know-it-all and a welcher.
Nearly a year into the agent’s assistant job, I was developing secondhand emphysema from being confined to an office all day with a two-pack-a-day smoker who also turned out to be verbally abusive, pickled in Chardonnay, and very, very cheap. Did I want to quit suddenly and spectacularly with no safety net? Almost every day. But did I responsibly seek out new employment and then magnanimously offer my soon-to-be-ex-boss a full month’s notice—during the holidays—before leaving? Yes to that, too.
(And still, when I showed up a couple of months later to pay my respects at her mother’s wake, she introduced me to the gathered crowd as “the assistant who abandoned me when my mother was dying,” ensuring that even after doing everything aboveboard, I now felt retroactively bad about quitting.)
After that, I held a series of jobs in publishing that I only quit for the sake of a raise, a promotion, or upward mobility in the form of slightly less jankity office furniture and a company BlackBerry. This kind of quitting seemed—per the social contract—to be the only acceptable way to do it.
That’s how I operated until two years ago, when I quit my most recent day job for the same reasons that I tried to walk out of the Bull & Claw in the summer of 1995. I didn’t have a better offer. I hadn’t won the lottery. I simply wanted to be HAPPIER, and the only way to accomplish that was:
1. Face my fear of being judged, criticized, and looked down upon for being “a quitter.”
2. Step off the motherfucking ledge.
For some people, step 2 might be the hardest. For me, the risks of leaving behind a salary and benefits and facing the challenges of starting my own freelance business were daunting, but I had plans to account for them. (In case you don’t know this about me: I’m big on plans.)
It was step 1 that had been keeping me up at night. I could hear Judgy, firing a warning shot across my pillow.
If you do this and it doesn’t work out, they’ll never take you back, you know. You’ll have proven you didn’t deserve your day job to begin with, and then where will you be? This sounds risky. I wouldn’t. Oh and PS, I don’t believe in you, so you probably shouldn’t believe in you either. PPS Now is probably NOT the time for a drastic haircut.
Fast-forward a couple of years and I think I can safely say quitting was the right choice for me. (I can also nominate that last sentence for Understatement of the Millennium.) And at some point while I was falling asleep for the first time in a long time without dreading my morning commute, I realized it hadn’t been Judgy whispering sweet nothings in my ear after all.
Much as I’d like to—and a bit of a theme in this chapter—I can’t blame him for this one.
Midnight in the garden of obligation, guilt, and fear
When it comes to taking risks, the seed of doubt can often be found growing out of YOUR VERY OWN BRAIN. It was planted there by a culture that values stability, and it thrives on obligation, guilt, and fear.
Much like marigolds get planted in real gardens to keep insects away from the more useful stuff (at least, that’s what I think marigolds are for), doubt is there for a reason—to preserve stability—which is often a very good thing, in work, finances, relationships, and the like.
You just can’t give the marigolds of doubt unlimited access to obligation, guilt, and fear, or they take over the whole joint.
It’s absolutely fine to tend the seeds. Acknowledge their purpose. Let them know that you know that they know that you know they’re there, and let them blossom just enough to do their job, but not so they smother everything in the vicinity.
Here are three questions you can ask yourself to keep the marigolds of doubt in check:
• Do you have an OBLIGATION to anyone else that factors into that risk you’ve been mulling?
You might think, Yes, yes I do! But is it a true obligation—like to people who depend on you financially? Legitimate obligations are beneficial weeds, like oh, I don’t know, pennycress or clover.* Those are there to help you balance out your whole garden. Doesn’t mean you can’t yank them at some point, just don’t be too hasty. However, if it’s an imagined obligation—like, that people might be disappointed in your choice even though it doesn’t affect them at all—then it’s just a regular weed, like crabgrass. Yank away.
Do you feel GUILTY about whatever risk you’re about to take?
Perhaps you want to run for president of your sorority even though your best friend has already declared her candidacy. That might get messy, and you’re not wrong to feel a little conflicted. But if it’s important to you and you’re not doing it just to spite her, you don’t have anything to feel guilty about. On the other hand, if you’re about to risk a friendship over something stupid—like shagging your buddy’s ex and hoping he doesn’t find out about it—stand down, Casanova. Some guilt is called for and some isn’t. Just be vigilant, or it will eat up ALL of your plants like a green hornworm caterpillar. Have you Google-imaged one of those lately? (Don’t.)
Do you FEAR what might happen after you take that risk?
Some fear is healthy—like, eating poison blowfish and barebacking may not be the risks you want to stake your crop on. (Far be it from me to judge, but in cases like these I’d say the marigolds of doubt are doing their job; fear is keeping them suitably vibrant.) Again though, it’s all about balance. If you sow constant, unrelenting fear in your mind-garden, you might as well drop a big blue tarp over the whole thing and let the weeds and caterpillars duke it out for supremacy. My money’s on the caterpillars.
BONUS QUESTION
• Do you FEAR being judged and criticized just for considering this risk in the first place?
Ah, and just like that, we’ve come full circle. Fear: IT’S A BITCH. You’ll remember that the biggest fear I had when I was weighing the risks of quitting my day job was “what other people would think,” and that fear—a big blue tarp decades in the weaving—kept me, for a very long time, from making what turned out to be one of the best decisions of my LIFE.
In the end, my only regret wasn’t over the risk I took, but the fact that I didn’t take it sooner. (But that quote sounds like it belongs on another cheesy motivational poster, superimposed over a photo of Eleanor Roosevelt or, like, Mark Twain’s mustache, and we can’t have that, people. I’ve got standards to maintain.)
It’s like I said at the beginning of this chapter: “Don’t quit your day job” is a stand-in for all kinds of reasons not to take all kinds of risks. And whether it’s running for office, getting a perm, or moving to a foreign country famous for its jungle fauna, don’t let anybody—be it Judgy McJudgerson or your own irrational brain—tell you that you CAN’T take it.
Or for that matter, that you WON’T succeed, it WON’T look good, or you WILL regret it.
Coincidentally, this brings us to Part III. Funny how that works.