Lessons, Challenges, and Wins of Leaving Corporate America
Dec 12, 2024
Lessons, Challenges, and Wins of Leaving Corporate America
As the year winds down, I find myself reflecting on a pivotal moment in my life—the last week of November 2022. It’s been two years since I set up that fateful meeting with my boss to put in my notice and pursue my business full-time. I can remember it so clearly, down to the hour. In honor of this anniversary, I want to share my journey as an entrepreneur, highlighting the fears I faced, the lessons I learned, and the wins I’ve celebrated along the way.
Facing Initial Fears and Doubts
Leaving a 22-year corporate career wasn’t a decision I made lightly. The idea of building a business that could replace my salary felt impossible at first. My mindset needed a complete overhaul, and surprisingly, it wasn’t my mindset that shifted first—it was my husband’s.
As I started sharing the details of my plans, like why I wanted to build a particular workshop or create a specific funnel, he became more involved. He even joined me in watching training sessions and attending a mastermind retreat. Seeing others who had successfully made the leap gave him the confidence to ask me a life-changing question: “Why are you still working?”
His belief in me was the catalyst I needed. Together, we mapped out what it would take to support our family of four for one year—including tackling the elephant in the room: health insurance.
Biggest Challenges as an Entrepreneurial Family
1. Navigating Health Insurance:
Health insurance has been, and continues to be, our biggest challenge as an entrepreneurial family. The costs are astronomical, and finding adequate coverage has required meticulous planning. Even today, it’s our largest family expense, and I could easily dedicate an entire blog post to this topic alone.
2. Balancing Income and Expenses:
We approached this challenge with a dual strategy: increase income while reducing unnecessary expenses. For instance, we set boundaries on what we would spend personally and reinvest in the business. It wasn’t just about making more money; it was about being intentional with how we used our resources.
3. The Corporate Unraveling:
After 22 years in a system where more work equated to more success, detaching my self-worth from my output was one of the hardest adjustments. I had to shift my mindset to measure success by impact rather than hours worked. This has been a two-year journey and remains a work in progress.
Unexpected Lessons
1. Slowing Down to Heal:
After leaving the corporate grind, my body rebelled. The stress I had been carrying for years manifested in health issues—frequent illnesses, loss of voice, and general burnout. For the first time in two decades, I prioritized self-care:
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Eating regular meals
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Getting 8 hours of sleep
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Taking weekends completely off
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Reducing screen time
These small changes made a monumental difference in my health and productivity.
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2. Understanding Myself:
The free space in my schedule allowed me to dive deep into self-discovery. From exploring my human design to therapy, I began uncovering layers of my identity that had been buried under years of busyness. Questions like “Who am I when I’m not working?” and “What do I value?” became central to my journey.
3. Building a New Rhythm:
Creating a business that aligned with my life priorities meant redefining success. For me, it’s now about being present for my family, traveling, and enjoying the flexibility that entrepreneurship offers.
Biggest Wins
Over the last two years, the wins have been both personal and professional:
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Family Time: I rarely miss a bus stop drop-off or pick-up. These moments are priceless.
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Travel Adventures: We’ve visited over 15 countries as a family and maintain a goal of traveling once a quarter.
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Personal Growth: I’ve invested in therapy, yoga, and other self-care practices, which have helped me shed the “corporate skin” and lean into my true self.
What I Would Do Differently
Looking back, there’s only one thing I wish I had done differently: I wish I had started sooner. Having a supportive community and mentors earlier in my journey would have been invaluable. I also wish I had invested more in myself—both in terms of skills and mindset—from the very beginning.
Celebrating the Journey
As I prepare for 2025, I’m entering this next chapter with more confidence and clarity than ever before. This journey hasn’t just been about building a business; it’s been about creating a life I’m proud of. My hope in sharing this is to inspire you to believe in the possibilities ahead, even when they seem out of reach.
So, as we close out the year, I encourage you to celebrate your wins—big and small. Dream bigger. Take the leap. And remember, the path less traveled is often the most rewarding.
About the author
Holly Haynes is a business strategist who loves a good plan and flow chart. She is crazy passionate about teaching women like you how to build your dream job and scale to 6-figures without sacrificing your weekends or priorities.
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