Quitting Up

Why leaving a job without a plan may be the best career move a person can make.

I did it again. I quit a job—one I loved in many ways and I know many would be eager to have. But there were plenty of problems, as well. As I grew increasingly unhappy, sleep-deprived, and frustrated, I kept trying to make it work. Until one day I just couldn’t any more.

When I say I quit, I don’t mean I left one full-time job to take another. That’s the assumption, right? When you announce you’re leaving, people automatically ask where you’re going, because it’s very hard for most people to imagine leaving for the sake of leaving. But that’s the step I’ve taken several times throughout my career. And while in some instances, I could have quit a bit more politely, strategically, or stylishly, I have never once regretted leaving. In fact, I’m pretty sure quitting has been among the best career decisions I’ve ever made.

Walking away from a clearly defined path, reliable salary, and paid time off takes courage. It is a risk, and I don’t want to minimize that. But taking that step in the “wrong” direction, or leaning sideways as I sometimes call it, has exposed me to more experiences and people than I ever would have encountered while ascending that ladder one rung at a time. Increasingly it’s a way of working that businesses are embracing, too, which in some cases makes quitting a real win-win.

From Fear to Fuck It
According to a 2015 Gallup Poll, 70 percent of U.S. workers either hate their job or are disengaged at work. Most of these people won’t quit. Or if they do, it will likely be to take another job at another company, essentially trading one set of problems for another. Surely big change is needed.

The rise of contingent workers may be that change, or it may be evidence that change is needed. Regardless, more and more people are jumping ship only to re-board through the side door. I find myself among them. Even if it’s not quite a revolution, it offers benefits for both sides. A friend of mine quit her job only to be contracted by the same company for three days a week, which allowed her time to comfortably pursue a new career writing for television. Her former employer was able to retain her expertise, which it was loath to give up, albeit on a different basis; she can now pick and choose which projects she’ll work on.

At a job, your progress can be tripped up by any number of factors beyond your control: lack of turnover, reorgs, layoffs, politics. On your own you have numerous paths for advancement, reversal, reinvention, education, and more. That’s true whether you’re a consultant or a temp, a sole proprietor or serial contractor or entrepreneur. So while quitting doesn’t mean the sky’s the limit, it does open you up to a greater variety of options — and more of them. And, hey, one of those options may be a much better job somewhere else. I’ve spent about half my career earning a salary and the other half as a sole proprietor. In a long and varied career, there’s a good time for just about everything.

After you quit, you’ll sometimes make less money, or even no money; most of the time I’ve made more. I suspect the same is true of anyone who’s truly good at what they do, because exceptional people are always in demand. (So, strive to be exceptional.) A salary may be stable, but it can also stagnate. When you’re independent you can ramp up or down depending on your needs. For businesses, a flexible workforce enables them to staff for immediate needs without making a long-term commitment, which everyone knows can be terminated at any time for almost any reason. A bad economy will hit both full-time and self-employed workers equally, though if you’re already used to the hustle and juggle of freelance life, you might be quicker to adapt to your new circumstances.

Companies these days all like to tout their commitment to “life-work integration.” How often is it true? When you quit, you are reclaiming that responsibility for yourself. It’s hard, if not impossible, for anyone to sustain the perfect mix of obligation and pleasure that life requires. But wouldn’t you rather handle it yourself than trusting your employer to provide the workload that works for you?

In my experience, consultancies are among the few work arrangements where experience, and therefore maturity, are still considered assets. Businesses don’t want to train a freelancer, and developing expertise internally takes time they may not have. So even as hiring seems to incline ever younger, the need for knowledgeable talent remains, but often in increments rather than full time.

Additionally, services like Airbnb, Etsy, TaskRabbit, and Uber, among others, are creating new ways for people to earn income. These companies aren’t without criticism, but nobody can deny that they’re providing opportunities and marketplaces, where none existed.

All of which is to say there’s never been a better time to quit, if quitting is indeed right for you.

Smart, not Sorry
Not everyone can quit, of course. My friend who’s a curator relays that her career success is contingent on being affiliated with a respected institution. In her field, freelancing is career suicide. In other industries, it’s simply not an option due to the need for special infrastructure or training. Some types of work doesn’t pay enough no matter if you hold one job or several. Health insurance is another thing that keeps people pinned to their jobs. While “Obamacare” has extended coverage to more Americans, it hasn’t quite managed to make it affordable for most people.

To thrive after quitting, you’ll want to give yourself a strong safety net in the form of a thriving professional network, the equivalent of 3–6 months expenses in savings (something less than 50% of Americans have), and a marketable skill or product. You’ll need to get health insurance one way or another, and you’ll be asked to cough up the portion of social security tax that employers traditionally pay. You may have to be your own IT person, accountant, and marketing evangelist. The more compromised you are in terms of your safety net, the more compromises you’ll have to make to make ends meet. At the same time, fear can be a powerful motivator and failing is among the fastest ways to learn. There may never be a perfect time to leap, but that doesn’t mean you don’t do it anyway.

It’s also good to remember that not everyone who works in a full-time salaried job is miserable. They are in the minority, but there are some people out there who truly love their jobs. You may be one of them, or at least remember a time when you woke up eager to start the day. The office needs more happy people. After all, who wants to work with someone who’s miserable? Not me, nor do I want to be among the miserable myself.

Do What You Really Want To Do
For as long as I can remember, my philosophy has been: in order to do the things you want to do in life, you have to actually do those things. Conversely, the best way to get stuck doing something you don’t enjoy is to consent to doing something you don’t enjoy. So if I find pleasure in writing, I should look for chances to do more writing. But if I don’t enjoy writing commercials, then I should say no to every ad agency that approaches me with a tempting offer.

Hopefully within any job there will be opportunities to do more of the things you enjoy, and wiggle room to avoid the things you don’t. Truly there are few greater pleasures than getting paid to get good at something you’ve always wanted to do. But if you find that the majority of your time is being spent on things you don’t want to be doing, or working under conditions you wouldn’t wish on your worse enemy (who may or may not be your boss), then it’s definitely time to leave. The longer you stay in a rut, the more entrenched you become.

Quitting sends the message that it is we who are in control. That we don’t have to do something that makes us unhappy anymore. That we no longer will support a status quo that clearly isn’t supporting us. If more people just up and quit, perhaps some of these places will start to listen.

In quitting my job, I positioned myself to accept a new project that pays comfortably, but comes without the nasty politics, constant travel, and unmanageable workload that were making me so unhappy. And it’s going to challenge me in precisely the areas I want to grow in. While I set things up with my new client, I’m taking some time off to think, take care of myself, focus on things I love. Not a vacation day, not a sick day. Just time. There’s not a job in the world that can offer me this.