by Gabby Sobieski
Careers are supposed to be linear.
Pick a field.
Climb the ladder.
Stay in your lane.
But if you look around Kickstand, that’s… not really how things worked out.
We have former teachers managing client accounts.
Healthcare professionals leading digital strategy.
And a founder who built a company partly from a long list of things she’d seen in other workplaces and thought: yeah, we’re not doing it that way.
This Women’s History Month, we wanted to share a few of those stories about career pivots, impostor syndrome, and what happens when someone decides to bet on themselves.
Kara’s Story: Career Pivots Aren’t Starting Over
Before joining Kickstand, Senior Account Manager Kara Kothmann spent more than a decade in education teaching high school Latin.
Teaching is one of those professions where you give it everything. Years of schooling. Long hours. Emotional investment in students who may or may not care about the lesson you spent hours preparing.
Kara describes it as, “using the top 1% of your personality every single day.”
Which is exactly why leaving that kind of career can mess with your head.
When you’ve invested that much time and energy into something, changing directions doesn’t feel like a pivot. It feels like abandoning ten+ years of work. And it’s usually accompanied by a pretty loud voice in your head asking:
Do I even have the right skills for something else?
Turns out, yes.
A decade in the classroom built skills that translate almost anywhere… even if it wasn’t immediately obvious.
- Managing people and personalities
- Handling constant time pressure
- Leading a room full of people who don’t always want to be there
Those are the kinds of skills good leaders rely on every day.
The turning point for Kara wasn’t suddenly gaining new abilities, it was realizing the ones she already had were valuable in more places than she’d assumed.
Her advice now for anyone considering a career shift:
Don’t sell yourself short.
You’re probably not starting from scratch. You’re just applying the same skills in a new environment.
As a Senior Account Manager, Kara now leads Kickstand’s edtech vertical, giving her clients a very hard-to-find leader who knows PR and the insides of a classroom.
Nycole’s Story: Sometimes the Plan Is Just “Figure It Out”
Nycole Walsh (Head of Digital Services) didn’t start her career in marketing. She started in healthcare, working as a nurse on a high-acuity neurological unit in a busy downtown hospital.
If you’ve ever worked in a hospital or know someone who has, you know what that means: long shifts, physically demanding work, and a constant stream of decisions that really matter.
Then life changed direction.
After several years at home raising her kids, Nycole decided she wanted to return to the workforce. But re-entering the job market after six years away is… not easy.
No recent experience.
No strong professional network.
And a job market that doesn’t always know what to do with nonlinear careers.
She started applying everywhere, even for roles she was wildly overqualified for, just to get back in. Eventually she joined Kickstand as a contractor on the digital team doing entry-level work.
It wasn’t the most glamorous role, but Nycole had already made an important decision: she wasn’t waiting for the perfect job. She was getting in the door and figuring things out from there.
Then things accelerated.
Shortly after she joined, the person managing the digital team left the company. Instead of hiring someone above her, COO Kristina Kennedy, promoted Nycole into the role.
At the time, Nycole had never worked in marketing… cue a very real case of impostor syndrome.
But she stepped into the role anyway, with a simple philosophy:
Don’t wait until you feel ready. Just jump in and figure it out.
She supplemented her on-the-job learning with external accreditation, including Analytics courses from Harvard Business School Online, market research certifications, and the CRE “certified research expert” designation through IIPMR. The dedication paid off not just for the company’s bottom line, but for client relationships as well…client outcomes improved, and longtime clients were even happier.
In her first year helping lead the digital program, revenue grew by more than 200%.
Five years later, the digital team has become a major pillar of Kickstand’s client work. Nycole credits a lot of that growth to something simple: being willing to sit in the discomfort long enough to learn.
Not everyone loves that feeling, but it’s often where the opportunity is.
Today, Nycole leads Kickstand’s digital team and her background in caring for people translates into an unparalleled level of client service for our clients.
Kristina’s Perspective: Build the Company You Wish Existed
Kickstand COO Kristina Kennedy didn’t aspire to be an entrepreneur. Growing up, her parents owned very small businesses and she observed the stresses of being an owner.
But years in high-growth roles inside high-pressure start ups, began to build observations. And yes, while many of these were filled with great mentors and well-run operations, Kristina will tell you, “Kickstand was built because of all the things we wanted to do better.”
Workplaces where burnout was treated like a badge of honor.
Companies where great people weren’t valued the way they should be.
Leadership cultures that confused toughness with effectiveness.
Those experiences led to a lot of internal decisions that started with the same mindset:
Not on my watch.
Kickstand became a culture that learned to perfectly balanced flexibility with accountability. It put the walk behind its talk with meaningful benefits that include:
- Design-what-you-need Bereavement Leave: Kickstand’s bereavement policy ensures employees have the time they need to grieve. With no familial requirements, employees can take up to 15 days off following the loss of a loved one, and they have a year to use it, allowing them time to grieve along with practical time to manage estates and other realities that need to be managed when a close loved one passes.
- Design-your-own Parental Leave: Starting with the premise of 18 weeks of full pay, balanced out as 12 weeks fully off and six weeks ½ time at full pay, Kickstander’s have one year from a birth or adoption event to design their leave to fit their family. Men and women receive equal leave.
- Working Parent Stipends: 80% of Kickstand employees are the dominant earners in their household. We know this means that if they choose to start a family, they need to be fully successful at work and growing their career. A $500 per month stipend can be used to help working parents get help at home to ensure they can continue to focus at work. It’s used at the employee’s discretion with many using it for meal services, laundry service, home cleaning, and more.
- Care Giver Sick Days: Kickstand observed many employees often needed to take a few hours or a day to care for a loved one, whether child, parent, grandparent, etc. In talking to employees, it was clear that many hold important roles in their families and want to be able to help and support during times of need. So employees no longer had to hedge, working from waiting rooms, or taking calls from the car while they took loved ones to appointments, or holding sick babies on their lap during zooms, Kickstand created caregiver days, where every employee is free to take time off to care for others (including pets!)
- Alt Fridays: A marquee benefit at Kickstand is our alt Fridays program. Every employee receives every other Friday off, reducing burnout and providing more time to pursue passions, travel, hobbies, and just time with friends and family.
Today, Kickstand is well-recognized for its culture and specifically it’s programs that benefit women in the workplace. You can read more in articles such as: Forbes Magazine, and ScaryMommy. Kickstand has been recognized as a top employer for parents by Digiday. In the past year, Kickstand has won Achievement in Equal Pay at the Stevie awards, and a Top Agency Workplace by Ragan, and was recently named one of the Best U.S. Agencies to Work For from PRovoke Media. You can also read more about Kickstand’s approach to culture and part of its founding story in co-founder Kristina Kennedy’s medium post here.
The Real Thread Between These Stories
At first glance, these stories look pretty different.
Teacher → PR
Nurse → Digital Marketing
Operator → Founder
But they have something important in common: none of these careers were linear.
Which is worth calling out, because marketing (and agency work especially) has a funny way of rewarding people who didn’t originally plan to be here.
Teachers. Journalists. Analysts. Healthcare professionals. Researchers. The skill sets are surprisingly transferable.
The real barrier usually isn’t capability.
It’s confidence.
Impostor syndrome shows up whether you’re changing careers, returning to the workforce, or stepping into leadership for the first time.
The difference is who keeps moving in spite of that discomfort.
A Final Thought for Women’s History Month
Owning a company (or helping lead one) is a privilege and a responsibility.
If you’re lucky enough to be in a position where you influence culture, hiring, or leadership decisions, the real question becomes:
What kind of workplace are you building for the people who come next?
At Kickstand, that question shows up in a lot of small decisions. It’s what drives our focus on creating a flexible culture that supports career switchers, especially those with caregiving responsibilities. Given that women disproportionately serve as primary caregivers for children and elderly family members, this flexibility is a critical component of their success and growth within the company.
That intentionality around culture and benefits is one of the reasons our workplace has been recognized in publications like Forbes and Scary Mommy.
How we hire.
How we support career pivots.
How we think about growth.
Not perfectly. But intentionally.
And if there’s one theme running through these stories, it’s this:
Sometimes the biggest career move you can make is simply deciding to try something new and trusting you’ll figure it out along the way.
