Way Out #19: From Being Told What to Make to Building a $1M Agency with Marianne Kaiser
Marianne shared a piece of advice in this episode, which I think many of you will find helpful. If you want to know when to quit your job, you should track the days you wake up feeling miserable using Post-It notes. Once you hit 30 consecutive days, you resign.
For Marianne Kaiser, she gave it about three times that long. She was working at an agency that had promised her carte blanche to build out their creative department, but they completely failed to align their actions with their words. On top of that, she was navigating the intense pressure of raising a sick infant who constantly battled ear infections, while working in an environment where mothers did not last long.
When the agency unexpectedly eliminated its healthcare arm, the sector Marianne was most passionate about, she made a bold move. She asked to be seen as a creative leader on par with the account managers and to help craft the strategic direction of the agency. She was met with silence.
A week later, Marianne told her husband she was going to quit. With his full support, she walked away from a perfectly good-paying salary to build a life on her own terms. Today, she is the founder of Contrary Collective, a marketing and branding agency that operates on a completely different model than the corporate giants.
The Foundation of Independence
To understand how Marianne built the courage to leap into entrepreneurship with two toddlers at home, you have to look at the "village" that raised her.
Growing up as a latchkey kid an hour outside of New York City, Marianne was surrounded by examples of grit. Her mother went to college later in life and eventually became a PA working in the ER. Her father took a massive risk by accepting a 100% commission job selling commercial brick in Manhattan. He waited nearly a year to see his first paycheck, while his family relied on neighbors and godparents to help raise Marianne. Meanwhile, her grandmother ran small shops and worked into her 60s, showing Marianne what a savvy businesswoman looked like.
Her father instilled in her the power of making her own choices. When Marianne was an eighth grader and decided she wanted to go to a boarding school in Connecticut just to take more art classes and play ice hockey, her extended family thought the idea was ridiculous. But her father supported her, telling her, "I'm going to let you make that decision... Because if I make you make a decision, you're going to resent me for it."
Finding Her Path (and Weird Toilets)
That independent streak guided her into her career, though not without some turbulence. In college, Marianne landed an interview for an art internship at a pharmaceutical advertising agency. The recruiter initially rejected her because she didn't know how to use design software like Quark or Adobe, but an Art Director saw her portfolio, bypassed the recruiter, and hired her anyway, promising to teach her everything.
Her very first project? Researching the weirdest toilets in the world so artists could render them for a 13-month calendar promoting a prostate medication. Marianne was instantly hooked, realizing she had found a career where she could get paid to be wildly creative every single day.
This mentor also gave her management experience within her first year, teaching her a crucial lesson: if you manage the work early on, you learn not to hold client feedback too personally.
Escaping the Traditional Agency Model
Over the next 12 years, Marianne climbed the ranks in Manhattan, eventually landing at an incredible agency in California. The four founders valued work-life balance and encouraged her to prioritize her family. But when that company was eventually sold, the culture shifted, leading her to a toxic culture where she began her 30-day Post-It note countdown.
When she finally quit, she decided to build the exact opposite of the traditional agency model.
With Contrary Collective, Marianne operates on a fractional model using 1099 contractors. Instead of forcing full-time employees to work uncompensated weekends on projects they hate, she asks her creative team how much time they want to work and what kinds of projects they are passionate about (like women's health or rare diseases). Then, she goes out and finds clients who perfectly fit their skills. Her ultimate vision is to run the business like a hair salon for creatives—a space where talented people can come in, use the agency's infrastructure, partner directly with clients, and avoid corporate burnout.
Surviving the "Tariff Season"
Entrepreneurship is rarely a straight line. Shortly after launching, Contrary Collective hit a massive dry spell around election time.
During this slow period, she landed a prospect call, only for the client to demand she slash her budget to one-third and accept an hourly rate. Marianne spiraled in a panic for two weeks, thinking she had made a terrible mistake. But after seeking advice from another agency owner, she learned a vital lesson in boundary setting. She realized she needed to confidently say, "It sounds like what you're looking for is a freelancer. And we're actually an agency."
Instead of letting the slow period defeat her, Marianne used the downtime to build her infrastructure, setting up AI programs, organizing project management tools like ClickUp, and designing a capability deck. When the market picked back up, she was completely ready to scale.
Redefining Success and Embracing Help
Early in her career, Marianne thought success meant becoming a Creative Director by the time she was 30. She eventually earned the title at 35, only to realize she hated it.
"I got there, and I was like, well, this isn't that cool. Like I go to meetings all the time... I don't do the craft anymore."
After reading an article about a woman at National Geographic who designed her perfect job and then made up a title for it, Marianne realized she didn't have to fit into a corporate box. Today, she lives in Kansas City, and her definition of success is much simpler: liking who she is and liking the people she works with.
She has also completely rejected the societal pressure that mothers must do it all. To build her business, Marianne leans heavily on her husband (who manages the after-school activities and handles her IT support) and is unapologetic about outsourcing domestic tasks.
"There come times where I look around and I say, if I need to build this business and focus on that... folding the laundry right now is not a thing that I can be doing," she explains.
By letting go of guilt, she has built a career that fulfills her, ultimately making her a better mother. She now has the total freedom to pack up her kids, drive to Texas for two weeks to visit family (her parents retired there), and work remotely without asking a boss for permission. And financially, when we spoke, she was on track to match her former corporate salary by year two. When I followed up with her recently, she shared that the outlook is even rosier. She is expecting to book $1M in revenue this year.
Marianne’s Advice for Wayfinders
For anyone feeling stuck and contemplating their own leap, Marianne offers three powerful pieces of wisdom:
Don't wait for the "perfect time" to leap.
It is easy to tell yourself that you will start your business when things calm down, but Marianne advises against waiting. "If you do it when you first feel like you wanna do it, then you can say you've done it," she says. "If you wake up every morning and you hate your job and you don't want to get out of bed and you don't feel supported... get out. Do your own thing."When business gets slow, be of service to others.
Every entrepreneur faces a terrifying dry spell. When Marianne hit hers, she stopped obsessively emailing prospects and started volunteering with a local organization called Veterans Without Orders. "The more you're doing for others, the less you're worrying about your own life. And when I don't worry about things, it's like the universe just shows up," she shares.Borrow self-confidence if you have to.
Imposter syndrome holds so many brilliant people back, but Marianne has a great reminder for anyone doubting their abilities: "...a lot of people run on self-confidence only. So jump into it. And if someone else trusts you to do the job, you're probably underselling yourself."
Follow Marianne
This post is part of the 101 Ways Out series: stories of people who found the courage to exit the status quo and build a life of purpose, freedom, and joy.
