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  • Writer's pictureKarla Ray

Social Savvy 'Boss Girl' Leaves Corporate Grind To Chase 'Moss Girl' Lifestyle

Somewhere on the internet, there’s a Myspace page with the most emo-curated song lyrics, background music, and top 8 you could imagine—one I’ll never be able to recover it because it’s attached to my .edu email address from college that I lost access to before I could ever change it.

Being on the forefront of social media- and the internet, really- is just one part of the millennial experience that is hard for the generations before and after us to understand.

Elder millennials, in particular, were coming of age as Facebook was being rolled out one higher-ed institution at a time. We Asked Jeeves before we ever Googled. Before Reddit, we had Yahoo Chatrooms (Which… ew. SHOCKING what we would tell strangers in those forums!) And before TikTok, we Vined (well, some of us. It was ahead of its time and really a flash in the pan).

I was lucky enough to be paired as a freshman with a roommate who had her own computer, which meant WE had our own computer in our dorm room. I didn’t have a laptop until maybe junior year? I would either check my email and send a few ‘pokes’ on Facebook (what a wild feature, Zuck) once or twice a week at the tech lab or on my sorority’s community desktop. Smartphones weren’t a thing… I remember when my sorority sister, Tess, first got an iPhone and we would all take turns using it to listen to music… the rest of us would be pushing buttons frantically to text on our Razrs. There were no Bluetooth speakers to listen to as we got ready to go out; we would throw a mix-cd we ripped from Limewire and put up with the random shoutouts mid-song for the teen DJ who was putting the songs on the internet illegally from his mom’s basement.

This is the perfect example of the type of photo I would upload from my pink digital camera to Myspace after a night out in college:

I actually remember one of my classmates getting written up by the University and having his internet access blocked for streaming movies from Napster.

The kids that grew up begging to have their own landline phones in their rooms and can still remember the days before internet were also fully immersed in it by the time we entered the workforce. As a young journalist, I remember creating my first Facebook page and then after about 6 months on the job, after being basically forced to by our web manager, creating my Twitter account on the eve of the 2008 election.

Something else happened in 2008 that shaped the millennial experience as much as the internet; a nationwide recession. Almost as soon as we entered the workforce, it was flipped on its head as companies carried out mass layoffs, people lost their homes, and markets crashed.

For fellow elder millennial Lindsey Pesch, it was the start of what would become more than 15 years of straight hustle to try to prove her worth—and it all revolved around an online space that grew up with her.

“I came into the professional world right when social media was becoming a thing,” Pesch said of her early days working in a public relations agency. “Facebook was still just for edu accounts. MySpace was really popular.”

In fact, it was creating a client’s MySpace account that started the trajectory that would afford her 9 years of working her way up through that agency and then landing a corporate gig with one of the biggest, best-known brands in the world—Darden Restaurants.

As in, Olive Garden. LongHorn Steakhouse. Bahama Breeze. At the time, Red Lobster.

The list goes on and continues growing, with Darden just acquiring my favorite upscale chain, Ruth’s Chris. Drooling just thinking about their sizzling steaks…

Any city in America has a Darden Restaurant. You’ve no doubt eaten at one at some point in your life, and it may just be part of your regular rotation (unlimited soup, salad and breadsticks is pretty tough to beat).

With its headquarters in Orlando, it is still considered one of the top corporations in town- key to the hospitality core that keeps families traveling to our theme parks and hotels year after year.

After nearly a decade helping other brands build out their social media, Pesch knew she had the secret sauce to amplify restaurants that were already household names to younger audiences.

“I went to the interview completely chill. I was like, if you find another person more suited for this job, go for it,” Pesch said. “They needed someone to come in and build social for Olive Garden. It was a step up for me, and it ultimately it worked out.”

The move to Darden wasn’t made without trepidation. Going from an agency to a publicly-traded corporation, even to do something as fun as social media, forced Pesch to question whether she was giving up a certain lifestyle client-based PR work afforded her.

“I remember in my interview asking the person who was going to be my boss- do you guys have fun? Because an agency is so rooted on fun, and happy hour Fridays, and parties, and it’s a lot of hard work, but there’s so much fun that’s intertwined with it,” Pesch said. “Ultimately, it still was a fun atmosphere, but it was just a lot more grown up. There was a much more diverse group of people, some who have worked there for a very long time that had all this wonderful knowledge, and a lot of people that were new just coming in with new ideas.”

That synergy was coupled with better compensation and more resources; a win win win for a young adult on the forefront of a rapidly-changing social media landscape.

There was also the quiet part that Pesch is willing to say out loud—the instant brand awareness that would come from her explaining her job to strangers at parties fed her ego in a way that an agency just couldn’t.

“It feels cool. It feels cool for people to know what you do, and that you work for this big company and that you're in charge of this really sexy piece of it,” Pesch said. “That felt so fun and so cool. I would go to parties and I would really hope someone asked me like about my job. Like, I would think about that.”

For those of us who experienced our coming of age in the Boss Girl Era, ego and attachment to your job title is a real thing. Our work experience and professional accolades are so intertwined with the value we allow ourselves to feel. Being raised by a generation that would spend decades in one place until retirement- entering the workforce amid a recession which taught us we had to be the hardest working person in the room or risk losing it all- it created a hustle culture that only now are we starting to see unwind.

But back to 2014, when Lindsey was the first social media hire for the Fortune 500 company.

“Darden was really behind the times when I joined,” Pesch said. “They didn’t have a real social strategy, they didn’t have agencies that were managing it for them. It was just so wild to come in and be like- you guys are grown… what is this?”

She started with Darden’s biggest brand, the real OG (Olive Garden) and eventually helped build social teams for the other restaurants in the portfolio. Soon, as one of the youngest managers in the corporate structure, she was leading teams of her peers and creating a social media command center on what she described as the main street of the corporate complex.

“It was pretty impactful, because everybody sees that the second they come into that building,” Pesch said.

Eventually, her title would match her experience and oversight of the teams of her peers, becoming Director of Social Media for Darden’s 9 full-service restaurant brands. She led a team of nearly two dozen people pre-pandemic, and oversaw the creation of thousands of pieces of content per year, including work that would earn her honors and accolades within the company and national write-ups when Taylor Swift herself set off the Twitterverse with a mention of Olive Garden in her song No Body, No Crime in 2020.

And though she was able to be corporate-edgy from time to time… it’s still corporate.

“They’re a really good restaurant company. They know how to run restaurants. And it’s a business. So at some point you decide, do we want to be like Wendy’s or Taco Bell on social? Do we want to be known for cutting edge social? Or do we want to deliver to our stakeholders and on Wall Street and run really, really good restaurants,” Pesch said. “Sometimes, you can do both. But I think we decided as a company who we wanted to be and who we wanted to be seen as, and I just don’t know that over the years that they really wanted to be cutting edge or current. They wanted to be good at social, but it just started to feel different after a while.”

Those feelings got even stronger when the world shut down during COVID. Remember the formative experience of millennials entering the workforce during the time of a recession? Well now we were hitting the midpoints of our careers and the entire world changed. We were forced into a hard stop and pivot from the hustle culture that raised us.

“It was a really challenging time to lead a team,” Pesch said. “We lost about a third of the people- not from layoffs- but contractors and agencies that we worked with, resources that we didn’t have anymore. And it got very hard.”

Tough times at work seem even more insurmountable when you’ve seen just how good things can be. Lindsey started at Darden on the same year as the Pasta Pass- as in, never-ending-pasta.

“What we had in 2014, it was lightning in a bottle. And after a certain point in time, when you’re at a company for so long, you think back and say- how can we get it to be like that again? But you’re never going to get it to be like that again,” Pesch said.

She didn’t know it at the time, but it set a ball in motion that would have her reevaluating all aspects of her life, not just work.

“It almost happened overnight,” Pesch said. “I woke up and it just started to feel like, this job just feels hard. It had never felt hard before. It was always hot button and it felt exciting, it felt challenging, and now it felt hard, but not in a challenging way. It just felt hard to show up, and it felt inauthentic, which is not me.”

“I am known for being transparent to a fault… and feeling like I was faking it, and faking the fun, and faking the excitement- it felt wrong. It did not feel good,” Pesch said. “It took me almost a year to realize what I had to do.”

She described that year as dark- a depression-filled summer of 2022 that was only made brighter when she adopted her dog, Bru.

It’s true that dogs change lives. Hard stop.

“I was feeling depressed and anxious and just these really negative feelings, it was hard to go into work… everything felt hard, nothing felt authentic,” Pesch said. “And then I got a dog. I got a puppy… and that breathed life into me. The serotonin, the endorphins, literally shook me and made me realize that I had lost myself in this job.”

There’s a saying that I’ll botch if I try to rehash it that means something along the lines of an employee quits in their mind well before they submit their resignation. But even when you resolve to do something- the decision is made- when so much of your self-worth is tied to your job (as most of ours are) it is hard to untether yourself from it.

“I started to realize this might not be my forever, which, in the first five years I could not ever imagine… why would I go anywhere else if it’s comfortable? I’m having these great opportunities, I'm respected, I have influence, this is great,” Pesch said.

The pandemic’s impacts on the job market made it even more difficult to leave her comfort zone. She’d been a Director for five years, putting her desired compensation far out of reach of other companies that had made cuts during COVID.

“There weren't a lot of jobs, especially in Orlando. I wasn't really trying to relocate, but I was willing to if it was the right job and it was amazing,” Pesch said. “So I started looking outside of Orlando… and it became very evident that the jobs that I was looking for weren't restaurant companies; they were things that were passions of mine, my real passions.”

Pesch loves a good bowl of pasta like anyone else, but she’s into fitness, wellness, and community. She started applying places like Nike and Mattel; brands that aligned with the best version of herself- the version we were all forced to reckon with during the isolation of the pandemic.

She was immediately humbled.

“I didn't get the callbacks. I didn't get the phone call. I didn't get the interviews,” Pesch said. “It really opened up my eyes of, well, maybe I'm in the wrong industry, or maybe I need to pivot. If I do want these jobs one day, I need to get some of this experience.”

“I realized I needed to make a real pivot to either set myself up for a more authentic corporate career or just something different.”

I believe most people who experience this type of rejection, who have the option to stay put in a Director-level job, would simply do that.

Pesch isn’t like most people.

“I think the compensation and the benefits and the comfort of this company that isn't going anywhere, it’s really solid… it’s scary. It’s scary to leave comfort, right?” Pesch said. “I think one of my superpowers is, as much as I have imposter syndrome, I'm just kind of naturally confident… I just really went in confident, made my resume as strong as it could be, and just kind of let the universe take the wheel.”

But in social media and life, you won’t get anywhere without strategy or engagement. In January 2023, during a conversation with a trusted friend about the battlefield of LinkedIn and Indeed, Pesch created an LLC.

During more conversations through the spring, the pull to actually create something out of that LLC got stronger.

“I started getting these signs from the universe, and really positive feedback… everybody was so supportive. They're like, Yeah, why don't you do that? That would be really cool. Like, you should. You should live your life and you should be happy,” Pesch said. “Being happy is so much more important than money. I know it sounds ridiculous. Most people are probably rolling their eyes. But I was at a point of- if not now, when?”

If you believe in the power of attraction theory or the idea that you should befriend your future self, you already know that what you speak into the world will become your reality; a future version of you has already done the thing you’re stopping yourself from pursuing. The hype squad behind Lindsey started to drown out her self-doubt. She started to believe them.

In the summer of 2023, she walked away from her Director role at Darden to launch 110 Cadence, a social media consultancy that allows her the freedom to sleep in until she’s ready to get up, daily pickleball and hot girl walks, unlimited time with her dog, Bru—she’s truly living her most authentic life.

And without the parameters of a corporate workplace, Pesch isn’t limiting herself or her endeavors.

“I tell people this is my f*** around and find out era in my life,” Pesch said. “I’m going to sound like a psycho because I want to do social media consulting, and maybe I want to do voiceover work, and I'm building my fitness business… I'm teaching yoga, and I want to teach dog yoga, and I'm getting my personal training certificate, and I'm also doing crafting, and I want to teach cross-stitch classes…”

This went on until I jokingly (half jokingly?) asked if anyone thought she was having a manic episode.

“I was so sheltered in this very corporate world for so long… I would go to parties waiting for people to ask me about my job so we could talk about work, and we would go out with coworkers and all we do is talk about work… and I lost myself,” Pesch said. “So now I'm just coming to find truly what gets me excited, what makes me happy.”

“If I'm my own boss, why can't I do it all? If it all works, and it all is fun, and it feels rewarding, then I'll do it all.”

It’s hard to believe that going from one job to multiple hustles is actually a slower life, but when you’re the one in the driver’s seat, it’s a totally different game. Lindsey jokes that she went from being a Boss Girl, to a Moss Girl.

“They would call me Boss Girl Barbie. And it was just so very cute and wonderful… I'm so glad I have that experience. But when I was transitioning into making this new decision, I needed to let all that go and be responsible for me. And if that means rolling around in the grass, or sleeping in until ten, or going to the gym for 3 hours if I want; whatever my body, the weather, the universe is telling me to do, I'm trying to just lean into those feelings,” Pesch said.

As a forever Type-A, natural leader, it’s tough to cut off the hustle at the root. Lindsey has had to resist her natural tendencies of trying to develop leads and do outreach nonstop. Instead, she’s trying to spend more time with her dog, Bru, and in nature (with… the moss).

“You’re rewarded for that behavior. You get kudos, you get recognition, you get awards, you get raises for being that boss girl… why aren't we rewarding moss girl?” Pesch joked. “Moss girls deserve a trophy for just being so authentic and chill.”

Though Bru and the pandemic were definitely on the list of Lindsey’s reasons to leave the corporate rat race, there is something to be said for leading a department made up of a lot of Gen Z colleagues. Seeing how another generation approaches work/life balance is a disruptor that can completely change your mindset.

“We were all raised by boomers who have a very linear view of what career looks like, where you go to school- you get a good education- you work for a good company- there’s loyalty, and this is how people are mentally trained to enter the workforce,” Pesch said. “And then years of hustle culture and grinding… and then Gen Z comes and looks at us like, what is wrong with you? You guys are absolutely wild.”

“I think it broke us all out of this fog, this kind of trance that we were in... and it made us start thinking, maybe it could look like something else. I think someone, somewhere, will do a dissertation on the older millennial generation and what’s happened and why we all abandoned, and essentially changed, the corporate workforce in five or ten years.”

Over the last decade, I’ve worked closely with a lot more Gen Z colleagues. The news industry has changed so much, and though Orlando is now the 16th largest market in the country, many of our producing candidates are coming straight out of college or *maybe* have one job before coming to our newsroom. The way we have to structure our communication with each other, the expectations for how to dress at work, it all has to be tailored with the mindset that Gen Z is simply there to get paid (which… is what we’re all there to do, right?)- certainly not to climb the corporate ladder that so many of us are ingrained to believe we should.

“They have boundaries,” Pesch said. “They don’t check their email on the weekends. These are just things that we were conditioned to do… especially working in social media, right?”

I’ve checked my email, Instagram, Facebook and TikTok at least 189234721 times since sitting down to write this blog. In my second newsroom, the expectation was to be on email all.the.time and even now, 11 years after leaving that place, it is still very hard for me to disconnect. But I do feel like the more time I spend with my Gen Z buddies, the boundaries are rubbing off via osmosis. I think boundaries are a sign of strength- a sign you’re willing to choose yourself instead of being railroaded into taking on more than you have capacity to handle.

“No matter what generation you are, you have to set boundaries. If you are working for a company you need to have a real conversation with your leader and say, hey, I know I’ve been working really hard for you, and I don’t want to stop working for you, but I need to set boundaries,” Pesch said. “Get the mindset that it is a job, and they pay you, and you deliver X, Y, and Z… and then use that time outside of it to try to do the self-searching, to do the meditation, to do whatever it is that brings you true joy doing these things.”

Those joy-drivers are helping bridge the gap between clients, too. The yoga classes that would get Lindsey out of bed during her depression are now helping to pay the bills, and keeping her busy.

“I realize that as I build this business, the more that I can embrace doing what I love, and what I'm very good at, which is social media with brands and businesses that align with my core values of moving your body and fitness and wellness and health, it will be really amazing,” Pesch said. “I thought this was a perfect opportunity for me to truly get back to teaching more consistent yoga classes… I find joy in teaching and giving that to people, making them sweat, building playlists and bringing my creativity out in that way. I’m very excited to be able to have more time and space to do that.”

Never one to fully sit still, Pesch is also studying to be a certified personal trainer. She’s also not opposed to bartending or dog walking to make extra cash.

“One of my favorite bartenders [pointed out] that people ask you what do you do for a job, but they don’t ask you- are you happy? Are you fulfilled? Do you have a good time? People don’t ask those questions at parties,” Pesch said.

So has she gotten over the ego-buzz of being asked what she does for work at parties?

“It's day by day. I'm not so aware about what people think. That was definitely something went away quickly. I had to make the decision and stand firm in this is what I'm doing,” Pesch said. “And actually, people have often said they’re so proud of me. So, the ego is still getting fed. Just in a different way.”

Her best advice?

“Get a dog,” Pesch laughed. “And your network is your net worth. I wouldn’t have felt so confident to do this if I hadn’t been able to go back in time to when I was younger, and I was really active in the community in different organizations, different companies, just putting yourself out there.”

Making connections in real life, and being truly social.

“It brought to life what was already there,” Pesch said. “It was lost, but it wasn’t gone.”

Connect with Lindsey @SewSweatSocial on Instagram!

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