How to quit your job without any regrets

What I did wrong when I quit my job

Whether it’s prompted by burnout or buyout, leaving a job can be tricky. While you’re trying to wrap up all that last-minute work and say your tearful goodbyes to coworkers, there are practical considerations you’ll also need to attend to. And you don’t want to drop the ball, or your financial life can fall apart. Vera, 39, knows from experience. She reveals why she fled a longtime job she loved, what happened in the aftermath, and what she’d do—and say—differently if she had it to do all over again.

Why did you decide to quit your job?

I’d worked for the same place, a publication in New York, for over a decade. Prior to the Great Recession, we had plenty of resources and a large staff, and then almost overnight we had to let go of a third of our team. Over the next few years we felt aftershocks of fairly regular layoffs, as the landscape of our business kept changing (or eroding, really). I was an editor close to the top of the masthead, so I was involved in management through these fractious times. Then, my boss, who I was very fond of, decided to leave. The stress finally led to me getting a debilitating autoimmune condition that resulted in a very literal head-to-toe breakout that made me look like a pink leopard, as well as severe nerve damage. All signs pointed to me closing out this chapter of my work life, and taking time off to get restored and figure out a job change for the future.

Wow. That sounds like a difficult time. Was it a hard decision to make?

For sure. I loved my job and the people I worked with. But I also felt as if I was white-knuckling my existence to some degree. There was a lot of back and forth between my boss and me about my decision—“Are you 100% sure you’re ready for this?”—and I found myself having second thoughts many times over those three months until my eventual last day, literally until I walked out the door that final time.

What other kinds of conversations were you having, to help you decide on and plan your exit?

Well, the first conversations were with my family and friends, who knew how much this job required in terms of time and energy, but also how much it meant to me. Most of them were supportive. Then came the conversation with my boss, of course, which led to tough conversations with my peers and staff, which led to more conversations with my family and friends about whether I was making the right decision. There were some tears. I will say, though, my experience in having these conversations did come in handy later with my sister, when she found herself wanting to leave her job. She’s married with two young kids. I was able to counsel her a bit, and encouraged her to talk with as many people as possible, because obviously losing a paycheck weighs more heavily when you have a family to support. I don’t have a kid or a spouse who depends on me, so I had a little less pressure than others in that area.

Had you prepared financially for life after quitting?

Pretty much, yeah. I had more than a year’s worth of salary banked, and a decent amount (about twice that) set aside for retirement. I knew I’d have health coverage for a bit. And I’d arranged for a buyout, which gave me some severance. But the reality when I quit my job was far different than the reality a year or two later.

How so?

My time off—my break, if you will—ended up being a little longer than I’d thought. I found myself going from feeling pretty financially secure to very suddenly feeling like I was burning through my savings at a much faster rate than I’d anticipated. My health coverage ran out, so then I was on the hook for almost $600 a month in expenses I hadn’t ever really had to think about. I had to start budgeting differently—hello Obamacare, goodbye personal trainer!

Did you figure out a new direction for your career?

I tried out some new things freelancing, which was great, but my work was primarily on a project-to-project basis, and I was making a lot less money. You can leave a job on your own terms, but you oftentimes have to seek out and return to work on other people’s terms, and depending on their needs. I went from the driver’s seat in my financial well-being and job security to the back seat. I also found out later that there were some things I wish I’d done that I hadn’t.

Like what?

Well, for one, I didn’t get a few things in writing that I should have. For instance, I stuck around until a certain date to lock in a bonus for the following year; when I went back to human resources to see about it all those months later, they told me the company had discontinued that particular bonus plan for former employees. I agreed to these terms on a handshake with my boss (who was now gone), which is as bad an idea when dealing with a large corporation as it is when loaning money to a friend. My lawyer told me there was not much I could do, since I never had them put pen to paper. So I would say: Ask questions about anything you think you’re leaving with, from your health care coverage to any possible bonus, and get it all in writing.

I would also be very clear with yourself as to not only what you want to do next, but how you’re going to do it. I had some rather vague notions of transitioning into consulting, and wish I’d used my considerable platform at the time to set up more meetings with people in that line of work. I would take out that pen again and actually write down my goals. If you can’t articulate in writing what you’d like to do next, it’s no better than daydreaming. It’s a good exercise, too, in order to see how you’d like to have your résumé positioned going forward, which I also wish I had fully updated and circulated before I pulled my office door closed that one last time. I feel like now, to some degree, I am playing catch-up, and it’s a little harder to make some of those inroads. An honest conversation with yourself using a pen and a canary pad about not only what’s next but how you’ll get there is essential. Might be painful, might be annoying, but it’s necessary.

Look, I still don’t regret the decision to quit my job, but I do regret some of the choices I did or did not make in preparing for it. However, I don’t regret traveling to Europe for seven weeks once I had healed a bit—that was a great decision.

(Quotes have been edited for style and length.)

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