Episode #048 · Rebecca Teaff
Girlboss Culture, Seven Figures, And The Freedom To Change Your Mind
Back in the height of Girlboss culture, success seemed to have a clear formula: grow bigger, earn more, scale faster, and keep moving the goalposts.
Those communities opened doors. They created spaces where ambition wasn't something to hide. But what happens when you achieve the thing you once worked so hard for—and realize you don't want it anymore?
Rebecca Teaff explores what it means to outgrow a version of success that once fit, the difference between building a business and building a life, and why more isn't always the answer. She shares the realities of stepping away from a thriving business, redefining ambition, and learning to make decisions based on what she wants now.
This conversation is about responsiveness, reinvention, and giving yourself permission to want something different—even when your life looks great on paper. It's also a reminder that success isn't a destination. It's a moving target, and sometimes the bravest thing you can do is stop chasing someone else's definition of it.
When Growing the Business Stops Being the Goal
When Rebecca and I first talked in 2019, Redstart Creative had a team of eight, an office, and a clear sense of the clients they wanted to serve. She was about to enter the Goldman Sachs 10,000 Small Businesses program, and growth was very much part of the plan.
Then came COVID. The team went virtual, eventually moved back into an office, expanded that office, and hired again. Rebecca describes those years as a constant cycle of meeting the next challenge and continuing to build.
“Grow, grow, grow,” is how she remembers the broader message to business owners at the time.
Eventually, though, the challenges stopped feeling like problems she wanted to keep solving. A state grant the company had been awarded was rescinded over a clerical error. Hiring and managing people had become increasingly difficult. And after years of meeting one obstacle only to encounter another, Rebecca was tired.
“I am tired of being a woman business owner being told that I need to carry the economy on my back,” she remembers thinking.
By then, she'd spent more than a decade building a profitable company doing work she cared deeply about. The question was becoming whether she still wanted to be the person responsible for taking it where it could go next.
Deciding to Sell a Successful Business
From the outside, Rebecca's business was approaching one of entrepreneurship's biggest milestones: seven figures in revenue.
Inside it, she was coming to a very different conclusion.
In May 2022, Rebecca was away on a work trip with her husband, sitting in a beautiful hotel room instead of attending an event because she was trying to determine whether enough receivables would come in to cover payroll.
“I think I'm done,” she remembers realizing.
Her son was 10, and the demands of the business were taking time away from her family. She could still see enormous potential in the company. In fact, she had spent years being good at exactly that—visioning, planning, projecting, and identifying what could come next.
The problem wasn't a lack of opportunity.
“I've grown this and this is really beautiful,” Rebecca says. “I'm not the person to take it into its next phase.”
That distinction mattered. She could be proud of what she'd built without volunteering to build the next version of it.
And she made that decision without knowing what she would do instead. First, she had to determine what leaving could actually look like: shut the company down, shrink it back to herself, or sell it.
She ultimately pursued a sale, talking with three potential organizations and receiving two offers. Months passed between making the decision privately and being able to tell her team and clients what was happening.
Going Back to Work After Entrepreneurship
Once the business was acquired, Rebecca stayed on for a period in business development. For the first time, she got to do the part of the work she enjoyed without carrying responsibility for everything else.
When she began considering her next move, she was certain about one thing: she wasn't going back into marketing.
She considered operations for a nonprofit, business development, customer support, and other roles that could use the skills she'd developed without recreating the career she'd just left.
Then she saw a marketing position at a university on LinkedIn.
The university had been part of Rebecca's life for years. Her mom had attended. So had her aunt, and her brother had done graduate work there. It was two miles from her house and rooted in values that aligned with her own.
She applied and eventually became its director of marketing.
Rather than seeing employment as a step backward after entrepreneurship, Rebecca began thinking about her career in phases. She was in her mid-40s with plenty of working life ahead of her. The business had been one phase. She could go somewhere else and make an impact during the next one.
There were practical benefits, too. After years of paying herself as a business owner and barely contributing to retirement, one of the first things Rebecca and her husband decided when she returned to employment was that she would max out her retirement contributions.
Her new job also gave her something she had specifically been looking for: work that mattered without requiring work to be the first priority in her life.
The Unwinding That Happens After a Major Career Change
Leaving the business didn't instantly make Rebecca feel like someone who no longer owned it.
When she started her new job, she remembers telling herself that she needed somewhere she could feel safe for two years. She pulled back from the networking, coffees, and online visibility that had been part of her life as a business owner.
“There needed to be a really hard line,” she says. “You're not the owner anymore. You're doing something else.”
She expected there would be unwinding. She didn't necessarily expect how long it would take.
Rebecca estimates it was about 18 months before she felt fully comfortable in her new life. Looking back, she can also see how mentally and physically exhausted she'd been. The transition gave her more room to take care of herself and to be present for a stage of parenting she hadn't fully anticipated.
Her son was entering the preteen and teenage years. After years of building her life around what the business needed next, Rebecca wanted to be available for what this stage of family life required.
And now another question is beginning to take up space.
Her son will leave for college in a few years. Rebecca has started wondering what she and her husband might want after that. A beach town? Learning to surf? Traveling through Europe?
Rebecca Teaff
Rebecca Teaff is a seasoned marketing professional with a career of 25+ years. She founded Redstart Creative with the mission of creating clear communications for those who drive positive change in the world. After running Redstart Creative for 13 years, Rebecca sold Redstart Creative and moved on to work as a Director of Marketing in the higher education space. She has crafted marketing strategy and design for a variety of non-profits, small businesses and higher education institutions. She is now the Director of Marketing at Notre Dame of Maryland University. Rebecca teaches marketing with the goal to make it accessible and actionable for all. She has taught via conferences, webinars, roundtables, podcasts and universities. Rebecca has been the recipient of The Daily Record’s Maryland’s Top 100 Women Award – Circle of Excellence, The Daily Record’s Successful Under 40 VIP List, The Daily Record’s Leading Women Award, 2015 and 2016 Smart CEO Corporate Culture Award, NAWBO-BRC’s Rising Star Award and the Top 100 MBE Award. She is currently on the advisory committee for Arrow - Maryland. Her past volunteer positions include board member of Maryland Nonprofits, a member of the Go Red for Women Campaign, chair of the B’more Creatives Mentoring Program, Marketing Chair for AFP Maryland, Marketing Chair for NAWBO-BRC, Parish Council at Church of the Nativity, and the Marketing Chair for her college’s Class Leadership Team.
