Keara Callahan thought she was doing everything right. She went to college, earned a degree in economics, and landed a well-paying government job as a tech consultant.
But she still felt something was missing. Watching endless TikTok videos of young people traveling and living freely only deepened that feeling.
In 2024, after breaking up with her longtime boyfriend and moving back in with her parents, Callahan quit her corporate job — a decision she wasn’t too sure about at the time.
“I’m very risk-averse, but I put in my notice and decided to pursue social media full-time,” Callahan, 28, told Business Insider. “It was probably the riskiest move I’ve ever made.”
Nearly three years after leaving her job, Callahan is now a full-time content creator with more than 300,000 followers across TikTok, Instagram, and YouTube. Her content, along with her newsletter and podcast, is geared mostly toward women and focuses on traveling and self-improvement.
Callahan said becoming her own boss was challenging, but worth it. While she’s putting in more hours than at her last job, she’s making more money and feels fulfilled.
Here are five things she’s learned since leaving the corporate world and starting over.
Always have a backup plan
Although Callahan was doing well in her corporate career, she knew better than to get too comfortable.
“We talk about corporate jobs almost as if they’re a guarantee that you’re going to be OK, but that might not always be true,” she said. “There are layoffs, reorganizations, changes in structure, and shifts in the economy.”
Before leaving her corporate job, Callahan had already begun building her social media following and making money from brand deals. She said that extra income made the jump more possible.
“Is it risky to do my own thing? 110%,” she added. “But one of the biggest lessons I’ve learned is that I’d rather have something on the side, like I did when I was working in corporate. It’s important not to rely entirely on things outside your control.”
Don’t fear failure or judgment
Callahan said fear of failure had long held her back, both professionally and personally.
“I was pretty young when I entered the corporate world, as most of us are, and I was fearful that if I did anything wrong, I was going to get kicked out or fired,” she said. “Fear held me back on both ends: fear of failure at work and fear of judgment outside work for doing something outside the norm.”
However, since quitting her corporate job, Callahan said she has found a new confidence in her decision-making.
“Our brains are wired to protect us from scary things, even when those scary things can be fruitful or lead to something better on the other side,” she said. “Regardless of fear, just take a step.”
Being your own boss takes discipline
While it’s nice to imagine not having a boss breathing down your neck to get your tasks done on time, working for yourself requires building your own structure and holding yourself accountable.
“In a job, you have a certain role and certain tasks you have to do on a daily or weekly basis,” Callahan said. “When you’re working for yourself, you have those same things, but there’s no boss above you telling you what to do or checking in to make sure the work has been done.”
Callahan admitted she struggled to balance work and free time after she first left her full-time job.
“I had all this time in the world, so I’d tell myself, ‘I’ll do it later,'” she said. “Then later came, and a week went by, then two weeks.”
To get herself back on track, Callahan leaned on her corporate experience to create a more structured daily scheduled.
Now, her days follow a routine: From about 6:30 to 9:30 or 10 a.m., Callahan focuses on herself, doing things like working out, before sitting down to work. Each day of the week is also designated for a specific task. Mondays are for recording content and working on her podcast, client calls happen Tuesdays through Thursdays, and Fridays are usually reserved for time off or half days.
There’s no shame in asking for help
Callahan said she struggled to ask for help or raise concerns while working in corporate.
“I felt like I always had to put on an act in corporate,” she said. “Depending on where you work in your organization, you might not feel comfortable asking for help because you might be judged or seen as less than.”
Now that she works for herself, Callahan has become less focused on titles and hierarchy and more focused on learning from others.
“I’ve been able to open up 10,000 times more and get the help I need for my business, and learning how to grow and create,” she said.
Have faith in yourself
Deciding when to walk away from her job was something Callahan contemplated for a long time. Looking back, she said she wishes she had made the move sooner.
“My biggest thing is timing,” she said. “There’s never going to be a right time for anything. I know that’s so cliché and so annoying, but I’d rather just bite the bullet now and figure it out along the way.”
While she used to worry about what her friends, family, and colleagues thought of her, Callahan now knows the only person she has to please is herself.
“I don’t care what other people think about me, my journey, or my trajectory,” she said. “I’m afloat and making a more livable wage than I had been. It’s all working out, and it’s going to continue working out from here on out.”
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