From Salary Guilt To Imposter Syndrome: Here’s What It’s Really Like To Work With Your Best Friend

The friendships forged in the fire of capitalism are some that I look back on most fondly. As a teenager, I worked at a major toy store, where shifts were passed trading gossip from local schools and catching up on the love lives of my fellow retail workers. Graduating into office jobs has proven to be essentially the same, but with an added distaste for the endless drudgery of copy-and-paste emails. The relationships formed — and which predominantly stay — inside the four walls of employment, can be vastly different to the other friends we make, and that’s something to celebrate.

There’s a reason people don’t like mixing friendship groups. On the rare full moon when your childhood friends, family friends, colleagues, school buddies, and even internet friends meet, it can feel like a blip in the space-time continuum. Consciously or otherwise, we tweak our personality depending on who we’re around. So when worlds begin to collide, it can be overwhelming trying to keep your nicely compartmentalised identities in order. 

But here, five people chat to Refinery29 Australia about the times when these friendship boundaries have been crossed, and their best friend has become their coworker. While visions of clinking champagne glasses in the fashion closet à la The Bold Type may come to mind, the reality can sometimes be a bit more challenging. 

Working in similar levels of seniority is one thing, but becoming your best friend's boss is another. Emily* found herself in this position when a close friend started working in her company, on the same team. While many friends appreciate a bit of distance at work, Emily wasn’t afforded the same luxury when she became her friend’s direct manager.

“The dynamic for me is just making sure I am giving her everything she needs to be able to grow and build confidence [in this] new job, but also giving her space to figure things out on her own and not suffocating her through that process,” Emily tells me. “But I get anxious about how I come across. I think we both communicate much better via phone calls [and being in-person],” she continues, explaining that tone can be misconstrued over emails and written messages.

When asked about the hardest thing about being her best friend's manager, Emily says that it’s the pay discrepancy. “Coming into [the job], she knew how much I was making, and then I knew how much she was offered. So that is hard… I definitely feel guilty about that,” she says.

One boundary that Emily has implemented is making sure that her friend doesn’t receive special treatment on account of their personal relationship. “You don't need to tell them about what's happen[ing] on a higher level or in the company just because they’re your best friend.”

For a growing number of entrepreneurs and freelancers, friendship can actually be a pivotal part of a business's success. Best friends, podcasters, writers, and business partners Grace O’Neill and Isabelle Truman are a testament to this — their pop culture podcast After Work Drinks is a cocktail of their candid camaraderie and witty commentary. 

The pair met in 2016 while working at Harper’s BAZAAR. In 2017, they started the podcast and had monetised it in their first month. “I mean, it's one of the best jobs you could imagine, being paid to drink a nice bottle of wine with your best friend and talk about all the things you'd be talking about off-mic anyway,” says Grace. 

“Plus, we have each other's backs always, which means if someone's having an 'off' week, the other person will pick up the slack and vice versa… I don't think [running After Work Drinks] would have been possible if it weren't for how close we are and how much we care about each other,” adds Isabelle. 

After Work Drinks began as a hobby, and therefore lacked the typical structure that traditional businesses depend on. “Everything has been learned by osmosis,” says Grace. “In some ways, it's harder than regular work because the things that make a working partnership good — directness, logic etc. — tend to not work so well in a friendship.”

“Getting the balance right between work and play is something that took us quite a long time. Frank conversations about what each of us needs… really helped us to preserve the most important thing, which is our friendship,” Isabelle echoes, pointing out the many times they’ve gotten sick of each other after a hefty recording schedule with social crossover.

“It’s a strange thing to commodify your friendship. Suddenly you yourselves become the 'product' and there's a certain pressure on the friendship that comes with that,” says Grace.

For best friends Aaron and Dana, their meet-cute actually does read like something out of The Bold Type. They were both studying fashion part-time, which led them to work at the same media company, where they officially became acquainted through lift rides. 25-year-old Dana, who is now a state partnerships manager, was first drawn to Aaron’s outlandish outfits.  

“Aaron used to wear these crazy Zorro capes and cowboy outfits,” Dana tells me. “It was just such a vibe that I was like, 'Who is this amazing human and how do I make him my friend?’. One day I just ambushed him and was like, ‘Let's do lunch’. And from then we've been inseparable.”

“As someone from Adelaide who didn't know anyone in Sydney, and who was already feeling like an imposter in a new city and industry, this particular moment felt like something out of a movie,” Aaron recalls. A few years later, Dana put him forward for a job at the media company she was working at, and the pair has been working together ever since. 

Now 29, Aaron relishes having a friend that gets what you do. “There's a special comfort in that,” he says, pointing to the trust, mutual respect and similar energy that he and Dana bring to their professional lives.

It wasn’t an easy onboarding though, with Aaron grappling with issues of imposter syndrome. “The hardest thing for me was the fear of not living up to expectations of the team who already knew me outside of work or letting my friend down if I didn't deliver on the role,” he says. “I later realised these were my own insecurities playing out and a mindset I could control [and] shift.”

For the duo, setting strict work and friendship boundaries has been crucial to cultivating their relationship. “It’s almost like dating someone and just making sure that you have quality time together,” says Dana. 

Living in different states has meant a measly number of proper coffee dates, but as a trade-off, the pair has been able to see each other grow in their careers and otherwise.

“The best thing has been getting to witness her brilliant mind in action and see her succeed in real-time after years of hearing about the work she was doing… Getting to see her work from ideation to execution just makes me even more proud of her,” gushes Aaron.

“I legitimately might not be where I am today had she not said hello in that elevator.”