How to ask for your old job back

No need to play it cool.
No need to play it cool.
Image: Reuters/Yuya Shino
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When I was in my late 20s, I left a good job for a new position in a different city where I thought I wanted to be. Within the first week at my new gig, I looked around the windowless office where my cubicle was located, stared down the bursting binders full of paperwork that I was expected to organize and track, and realized I had made a big mistake.

That day, I knew I wanted to do something that was also scary and deeply embarrassing: ask for my old job back.

Why the Great Resignation may spark more boomerang employees

Asking to return to an old job is common enough. But the plight of the regretful ex-employee may become even more widespread in the wake of the Great Resignation. As Aaron Klotz, an associate professor of management at Texas A&M University, told Bloomberg back in May, “We’re going to see lots of ‘boomerang’ employees, who a year from now miss their jobs and decide their novel isn’t going as well as expected.”.

There are plenty of reasons why someone might want to return to a former job besides a bad case of writer’s block or an attempt at freelancing gone awry. With burnout a contributing factor in some workers’ decisions to leave, they may find that they’re eager to come back (with firmer work-life boundaries) once they’ve had some time to rest and recover. Or they might realize, as Aki Ito observes for Insider, that “during the pandemic, some people blamed their misery on their jobs when, in fact, we were all miserable, regardless of our employer.” And then there’s the risk that always accompanies switching jobs: It’s impossible to know exactly what we’re signing up for, and the reality of a new position can make our old one look dreamy by comparison.

Whatever the cause, it can feel humiliating to go to your old boss and admit that you made the wrong decision and you’d like to come back after all. What if they say no? What if they think you’re flaky and irresponsible? It’s easy to understand why Seinfeld’s George Costanza, second-guessing his decision to leave his job as a realtor, opted to simply go back to the office and pretend he never quit—a scenario drawn from the real-life experience of the show’s co-creator Larry David, who successfully pulled off the same move while working in the Saturday Night Live writers’ room.

Most of us probably aren’t able to slink back into our previous jobs unnoticed. But my experience asking for my old job back taught me some important lessons about shame, forgiveness, and being a boomerang employee.

Quitting a new job for another offer

What led me to my unfortunate apex of professional regret in that windowless office was this: The summer I was 28, I had an internship at an economic research institute and was preparing to drop out of graduate school in Oregon. I sent out a flurry of job applications, and didn’t hear back from any of them.

The good news was that, toward the end of the summer, the economic institute offered me a full-time position as an editor. I went back to Oregon to collect my things, drove cross-country with a friend, and spent a few weeks settling into my new life in the mountains of western Massachusetts, known as the Berkshires. Then the unexpected happened: One of my job applications came through.

The role was an editorial assistant position at an academic publisher in Boston. The title was lower-level than I would have liked. I’d already worked as an editorial assistant and then been promoted to associate editor in my early 20s. But having spent three years out of the job market while in grad school, and now attempting to return to the decimated media landscape in the aftermath of the Great Recession, I felt I didn’t have a lot of room to be picky.

Besides, when I’d worked as an editorial assistant in the past, it had been a fun, creative job. I had tracked payments for magazine contributors, sure, but I’d also chosen book excerpts and edited articles and written for the magazine. Surely I would have such opportunities at the new publisher, dazzle them with my talent, and quickly be promoted! And as a single person in my 20s, the lifestyle aspect of living in Boston had a lot going for it compared to the rural Berkshires.

So even though I’d only been a full-time employee at the Berkshires job for about a month, I accepted the Boston job and put in my resignation. The higher-ups were understanding about why I’d want to work for a large publisher and live in a place where downtown didn’t shut down by 6 pm. I packed my bags and moved again, for the second time in about two months.

My suitcases and I were getting very tired, but we had an even rockier road ahead.

When your new job is a bad fit

As it turned out, Boston was quite fun. I found a bedroom available on Craigslist in an apartment with a big fireplace and jewel-toned woven rugs. I bopped around my new neighborhood of Somerville, replenishing my wardrobe at thrift shops and catching indie movies at the local theater.

But I’d been very wrong about taking the new job.

It was by no means objectively terrible. The other editorial assistants were a friendly bunch, organizing group trips to the coffee shop mid-day and inviting me along for karaoke night. I had three bosses, all of whom were perfectly reasonable people.

The problem lay in my job responsibilities and how I felt about them, both of which I’d drastically miscalculated. Unlike my former experience with being an editorial assistant, this was a truly, entirely administrative job. I’d had fantasies of being able to quickly prove myself and work up the ladder, but it was clear now that at a publisher so big, there was a lot of process involved with such decisions. As the most recent addition to the lineup of highly qualified assistants, I was at the end of the line. Also, the salary was very low, while my student loan payments were high.

At my old job, by contrast, I’d been doing the work I wanted to do and believed I was ready for: editing and writing. What’s more, I’d had a better salary and more exposure to the sun, from which the editorial assistants in Boston were cut off due to office design.

I cried silently in my cubicle as I rifled through contributors’ tax paperwork and sent new contributors more forms to sign. I cried on the T to and from work. I’d been so stupid, so short-sighted, so financially irresponsible! I felt that I couldn’t trust my own ability to make good decisions, or even to know what I wanted out of life.

A template for asking for your old job back

My friends and family told me if I wanted to ask for my old job back, I should. After all, they argued, the worst they could do was say no. I knew they were right, but I was still shaken up. The upheavals of the past few months were taking a toll on me; so many big decisions, all compressed together in one short amount of time. I was judging myself for making a mistake, and I felt sure my former employer would judge me harshly, too.

Still, I’d left on good terms with my old job. Even though I’d only been there a short while in a full-time capacity, I’d worked there for two summers while in grad school, so they knew me pretty well. I finally took a deep breath and wrote an email to my former manager.

Here’s what I wrote, in case anyone in a similar position could use a template:

Hi [Name],

I hope your week is going well! I wanted to write to see if it might be possible for us to talk about [name of employer]. I’ve been giving it a lot of thought, and if there is any possibility that I might be able to return to my position at [employer], I would love to talk to you.

I know this is unorthodox, but my time here in Boston has really allowed me to see what a unique opportunity I have at [employer]. There I can do work that I’m truly interested in: contribute in substantial ways to the organization through both print and new media; develop my knowledge of writing, editing, and economics; and work with an amazing group of brilliant, committed people. This position at [other job] isn’t what I was expecting in terms of both responsibilities and future possibilities, and it’s only made me more aware of how much I appreciate the opportunities I had at [employer].

If returning were an option, I would do whatever I needed to make it happen (including, for example, signing a contract committing to being there for at least a year or two). If not, of course I absolutely understand. But if you think it would be worth discussing, I would definitely appreciate the chance to talk with you about it.

Thanks so much,


Advice for would-be boomerang employees

This is hardly the only way to ask for an old job back—but I did inadvertently wind up following a couple tips from career experts. Here’s some of the best advice from around the web:

  • Email is better than a phone call. “If I were your manager, I’d appreciate getting an email about it instead—because there’s a decent chance that she’s going to be taken off-guard and that she’ll want to put her thoughts together—and maybe talk to others there—before responding,” Alison Green writes in her column Ask a Manager
  • Be sure you’re ready to stick things out. “If you go back to this company, you need to be committed to staying for a good long time,” Green adds.
  • Emphasize how the employer will benefit, too. “Keep the focus of your story on the benefits of hiring you the second time around, since this is now what separates you from other candidates,” Don Raskin, a senior partner at ad agency MME, advises in Fast Company. “Include new skills you’ve acquired in the meantime, plus your extensive knowledge of the company and the way it operates. Talk up the fact that you have relationships already in place with employees in the company, and emphasize how quickly you’ll be able to hit the ground running and get back up to speed.”
  • Rein in the shame. “Whether it’s a week or a month or a few days in, someone saying [their new job] isn’t looking like it’s a great fit isn’t something to be embarrassed about,” Brendan Browne, then the VP of global talent acquisition at LinkedIn, told Refinery29 back in 2018. “At least in tech, where the supply-and-demand ratio makes it an employee market in that it’s hard to find great talent, most companies that prioritize recruiting, hiring, and talent would welcome that call, especially if it’s someone they didn’t want to lose.”

Mistakes are inevitable

That last point from Browne is the message that I most needed to hear during my own job crisis. It’s so easy to beat ourselves up when we make a mistake or fail to accurately predict the future.

It is, of course, important to do your homework before accepting a new job or striking off on your own to start a business. It’s a good idea to talk to people who’ve held similar roles, or who’ve worked at the same company or with the same boss, or who’ve tried their hand at the entrepreneurial life.

But the reality is that we can’t always predict how we’ll feel about anything before we’re actually doing it. Sometimes we don’t consider how our own dispositions will influence the way we feel about a role, whether it’s managerial or a job with little human contact—a phenomenon psychologists refer to as “personality neglect.” Sometimes we suffer from what Harvard psychologist Dan Gilbert calls “impact bias,” or the tendency to overestimate how strongly we’ll feel about a new situation and how long we’ll feel that way. (Maybe we only think we’d feel happier working at a prestigious company, but once the initial glory fades, we find we miss the freedom we had at our old no-name gig.)

And more broadly, there are some aspects of a new job that we just can’t know in advance, such as: how team dynamics will play out, what the workload will be like on a day-to-day basis, whether a new boss gets testy under pressure, and if the company will wind up pivoting in a new direction in just a few months.

Often, it’s only through experience that we find out whether we’ll like a new endeavor or not. But that shouldn’t prevent us from making changes and taking risks. And if you’re good at your job and left your former employer on a positive note, chances are your former employer won’t look down on you for knocking on their door again. So long as there’s an open position, it’s often in their best interests to welcome you back, as you’ve already been vetted and trained.

In my own case, everything worked out in the end. My old employer hadn’t hired a replacement yet, and the higher-ups were sure we could work something out. No one at my old job was as hard on me as I’d been on myself. I returned, and wound up staying there for two years.

I’ve always been grateful for the compassion they demonstrated, and in the years since I’ve done my best to adopt a similarly nonjudgmental attitude toward myself and others as we navigate our career paths—often through trial and error. While writing this article, I came across the email the top boss wrote when my manager asked him if I could come back, which she then forwarded to me. If I’m ever in a position to re-hire someone, I hope to extend them the same grace.

“When she wanted to leave, I could understand that she wanted to pursue what she saw as her dream job,” he wrote. “I can equally well understand that things aren’t always what you think they will be. Better to figure this out early in your life, and early in the experience.”