We all heard about the Great Resignation, where millions of professionals quit their job during the pandemic in order to find balance and pursue fulfillment. Well, today, among those who took the leap, 80% regret ever quitting in the first place. Sometimes we have to actually make a move before finding out it’s the wrong one, and that’s okay.
If you’re experiencing a bit of quitter’s remorse, here are a few tips on how to ask for your job back with your pride intact:
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1. Be sure you’ve weighed the pros and cons of going back to a former employer.
Maybe the new job you quit the old one for just didn’t stand up to the interview hype, or you just miss your old gig and coworkers. Write down all the benefits and possible pitfalls of going back. Will you have to settle for less money? Did you leave the company on good terms? Is this something that will advance your career? Do you just need the money to pay your bills? (In that case, you might want to just consider applying for a whole new job elsewhere.) Before asking for that job back, be sure you’re aware of all outcomes of your decision.
I once considered going back to an old job after hitting a slump early in my self-employment journey. After talking with a few friends I still had in the industry, they highly recommended that I push through and find other ways to bring in money while boosting my client roster. Looking back, it was the best decision not to return to an old job because I would not have the flexibility or job satisfaction I have today as a digital nomad, nor would I be earning the money I am today.
2. Reframe the ask.
To ensure you’re not coming off desperate, be sure to start off by emailing your former employer or HR department, briefly detailing what you loved about the position or company, and expressing that, after some reflection, you’d be interested in reconnecting to be rehired.
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3. Request a meeting to discuss your options.
This is a good idea since you can better pitch yourself to get back into the fold with an in-person or phone conversation. It’s much more personal, and you can really let your former manager or HR rep know the details of why you want to come back and why you would be an asset to the company if you did. This is especially important if your position hasn’t already been filled, if you took major contacts or connections with you when you left, or to leverage better pay or benefits this time around.
4. Be authentic and honest.
Oftentimes, people respect honesty, especially company leaders, with integrity. I once resigned from a job, thinking I was going to pursue higher education full-time. I didn’t want to have to juggle my studies with holding down a job that I really loved and wanted to give my all to. After a bit of thought, I decided that missing out on the opportunity to really thrive in that role and continue the work I’d been doing just wasn’t worth quitting to go back to school full-time, so I was honest, and I got the job back. My manager was very encouraging and actually was happy I’d asked to rejoin the team. If you left the job due to what you thought would be a good life pivot or for reasons that are positive, just keep it real with your former manager and allow them the chance to offer understanding and grace.
5. If the position has been filled, apply for another one.
Many companies keep employee files in their systems for quite some time after someone resigns, and there may be other opportunities for you to get your foot back in the door. If you find that your position has already been filled, apply for another position with your former department or another department altogether, either through your former company’s HR portal or via a recruiter. Talk to your former colleagues or industry friends and find out about what’s available. They might even be able to give you a heads-up when a position is opening that’s perfect for your comeback.
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Skylar sees things differently. At the time, she was shooting content on her iPhone. Temi came into the picture with a new perspective, an understanding of tech, and, eventually, a camera. “He doesn't give himself enough credit,” Skylar says. “He wasn't just my tripod. He wasn't just standing behind the camera and going ‘click.’ He was giving advice. He was giving me insight to how I could look at things from a different perspective. And I was like, 'Oh, he’s an artist.' I think it was maybe a heartbeat of that kind of energy of like, ‘Baby, can you take this picture?’ And it turned so quickly into, we're partners. We can work together in a way where we're advancing each other's creative thinking.”
The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Temi and SkylarCj Hart @hartbreakToday, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak