Way Out #34: From the Rat Race to 3:30 Pickups: The Fractional COO Blueprint with Courtney Cook
In corporate America, we are trained to measure our worth by performance reviews, salary bands, and titles. For Courtney Cook, who was an e-commerce operations manager at Hallmark before becoming a startup COO, the breaking point didn't come from a dramatic layoff. But the feeling is universal.
Courtney was at her employer’s conference in Austin when AC/DC’s "Thunderstruck" blasted over the speakers. She immediately felt grossed out, like she’d walked into a frat house. The feeling that was lurking in the back of her mind was confirmed: “I just don't feel like I fit in here.”
"I went back to the hotel room and told my husband: I can't do this. I cannot work in the corporate world. I can't play the game. I need to find my own path," Courtney shares.
Today, Courtney is the founder of Monarch COO, where she serves as a fractional COO for visionary founders. Now that she’s her own boss, she’s become crystal clear about her priorities. She never misses a school pick-up, she serves as PTO president, and she no longer feels stressed and drained at the end of the day.
Here is how Courtney stepped off the corporate hamster wheel and built a profitable business on her own terms.
It’s in Her Roots: Work Ethic and Community
Courtney’s parents were always entrepreneurial—from running an electrical contracting firm and sign shop to a hunting lodge and rental properties.
"They always had so many irons in the fire," Courtney recalls. “If we had a snow day, we had a list of chores. Our snow days were not fun. They had really high expectations. If the garage wasn't done good enough, well, you got to do it again. So one of the things I like to say is, 'Why not do it once when you can do it twice?' Because we learned that if it's not good enough the first time around, my dad was definitely going to make us redo it."
Her upbringing helped her leap into entrepreneurship later on. She was always tending to things, whether her 4-H animals or plumbing problems at home. Challenges do not intimidate her. She learned early on that she could figure out anything. She also grew up in a small community with a graduating class of 60. Everyone was supportive, and she had a deep sense of psychological safety. Several of her teachers and her basketball coach all attended her wedding!
When she entered the corporate world, everything she knew about human connection and honest transparency was challenged.
The Illusion of Corporate Safety
With a background in finance and supply chain management, Courtney built her early career in Kansas City’s fast-moving e-commerce sector. She mastered complex backend inventory systems across thousands of SKUs, coordinating supply chains across major retail partnerships, Amazon channels, and direct-to-consumer platforms.
She scaled and led a high-performing operations team, steering logistics through the unprecedented demand surges of online retail during COVID-19. Yet as she advanced into management, direct execution was replaced by bureaucracy. As she explained:
"You've hired me to be the expert, but yet I still have to convince you seven times, seven ways of what I think we should do. That lack of transparency gives me the ick. If you can't be transparent, I can't trust you—and why do we want to do business with people we can't trust? If we all see that something is broken, why are we pretending it's not? And if you say it, you are in trouble."
Ready for a change, Courtney serendipitously wound up with an opportunity to work at a scaling startup. You see, she’d purchased a goal planner from Cultivate What Matters. A few weeks later, an email arrived announcing an opening for a Chief Operating Officer to work alongside founder Lara Casey Isaacson. Courtney applied that night and ended up joining the company. She streamlined cross-channel operations, expanded operating margins, and helped steer the company through a successful acquisition by a major publisher.
Through this experience, Courtney realized a few things that would begin to shape her offerings through Monarch COO.
Founders are often visionaries with no business experience. They need help with execution and making smart, profitable business decisions.
Founders rarely need full-time executives. Even multi-million-dollar brands may only need part-time (fractional) COO support.
Following the acquisition of Cultivate What Matters, Courtney transitioned with the brand into its new parent company, a major publisher. But once she got there, she didn’t see a career path. She decided to take matters into her own hands again.
At Hallmark, she had been a power user of an enterprise SaaS platform that aggregated messy Amazon data to automate decision-making. She loved the software so much that she had previously tried (and failed) to replicate it in Tableau. When she looked for her next step, she reached out to the customer success manager who had managed her account and ended up joining his team. While she thrived working directly with clients and learning the service side, the broader corporate culture and executive leadership soon proved to be an entirely different story—cue the CEO dropping F-Bombs and AC/DC walk-on music!
Exit Strategy: Maternity Leave, Daycare Math, and Structural Autonomy
Once Courtney decided to leave, she didn’t immediately pull the trigger. She is an operations expert, after all, so she mapped her exit systematically. She brainstormed names with her husband in January 2023, registered the LLC for Monarch Co. in March 2023, and stuck around for her signing bonus, which paid out in the fall.
When her son arrived in January 2024, she started aggressively applying for other jobs.
"I went on maternity leave [and] was applying for every job under the sun. My resume is great, I have a lot of experience... Surely I have three months to find a job. And apparently, no—the sign from the Lord was, 'No, Courtney, you are not gonna go work for another corporate job.' I am telling you, it was crickets from every single company. It was so silent. It was deafening... It was so obvious to me: 'Okay, I guess because this isn't working, I have to get something going with my business. I just have to.'"
Then came the childcare friction. Courtney’s local daycare center said that an infant placement would not open until late summer. At the same time, a colleague of hers sent two referrals her way for corporate advisory work. In the blink of an eye, she’d replaced 50% of her income.
Courtney took a step back and audited her situation:
Returning to her normal schedule without full-time child care was unsustainable.
Designing her own fractional schedule removed the need for 50 hours of paid childcare.
Two anchor clients served as proof that this could work and provided a predictable baseline cash flow.
She gave her manager her notice and stepped into full-time self-employment in Spring 2024.
Redefining Daily Rhythm: The 3:30 PM Anchor and the Weekly Cockpit
Instead of bracing for Sunday-night scaries or absorbing reactive calendar requests, Courtney runs her advisory firm around her schedule:
The 3:30 PM Non-Negotiable: "I want to have the flexibility to pick her up... I get to be the first person that greets her after her school day and to hear how it was. [It's] being able to say, 'This is what I'm going to do, and sorry, I can't meet with you at 3:00.' The ability to make that space in my calendar for volunteering, like being able to be PTO president and work... that is the best."
Evening Presence: "I remember feeling like my parents... were really tired a lot, and that did leave a mark on me of like, I don't want to be snappy with my children in the evening because I'm so tired from work... We don't have to be dog-tired. [The other night] my daughter is opening up a Bluey book reading to our 18-month-old, and he's just so into it. Little moments like that—those are what I'm living for, not all the work."
The Asana Weekly Cockpit: To prevent client scope creep, Courtney runs her business through her Asana dashboard. Every Monday morning, this "cockpit" maps active client milestones, key deliverables, and protected family blocks, ensuring she is on top of things with room to breathe.
Financially, her fractional practice out-earns her previous corporate salaries. She no longer has to commute or travel for work. And now her family can invest more intentionally, including funding private education for their kiddos.
Courtney’s Tips for Wayfinders
For corporate leaders and working parents assessing their own paths out of corporate, Courtney highlights three core principles:
Clarify the Non-Negotiables on Paper: Do the reflective work before you leap. Open a goal planner or a notebook and audit your energy: What fires you up? What gets excited? What do you want to say yes to? What do you want to say no to? What are your dreams... get them on paper.
Sever Your Identity from Corporate Metrics: Corporate institutions incentivize you to tie your value to your title, salary, and performance review. We have to deconstruct that. As Courtney says, "My identity was fully wrapped up in my success in my career: what my performance review said, what my salary was, did I get the performance review bonus... [You need] a place to put your identity that's not in success or failure... There is so much more to life."
Small Actions Are Enough: "Make little steps every day to cultivate those things and try to learn more about yourself. It can be so simple. It doesn't have to be these grand things. We can just live in our little homes, our little neighborhoods, and it can still be really special," Courtney reminds us.
Listen to Courtney Cook's complete story on 101 Ways Out (Episode 35) to learn how she structured her fractional pricing, structured client onboarding, and established her operational model.
Follow Courtney Cook
🌐 Website: Monarch COO
✉️ Email: Courtney @ Monarch COO
💼 LinkedIn: Connect with Courtney Cook
📸 Instagram: Follow @monarch_coo
Corporate culture says that flexibility is a perk and we need to always ask for permission to do what we want. And of course, choosing family over corporate politics comes with a penalty. Courtney rejected that script, prioritizing her family and her own agency. She now runs a thriving fractional business built around 3:30 PM school pick-ups and evening presence.
You don’t have to wait for burnout or a crisis to claim control over your time. The 101 Ways Out 30-Day Program gives you the structured framework, companion workbook, and step-by-step roadmap to transition from employee to sovereign operator.
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.
