The Moment Everything Changed
About 13 years ago, I had to make a decision—one that would change the trajectory of my career and my life. Should I continue in my almost two-decade-long corporate retail career, or was it time to take the leap into entrepreneurship full-time?
It wasn’t the first time I had faced this crossroad. A year earlier, the company I worked for was going out of business, and being laid off forced me to rethink my next move. But at that time, I chose to stay on the corporate path. It felt safer. More predictable.
But this time, something was different.
🔹 I felt a deep pull to do more… to think bigger. Corporate life was comfortable, but it didn’t give me the space I needed to explore, test, and truly see what I could do. I knew I had so much more to offer, and so much potential to do something "big", but I was working within systems, processes, and decisions that were often out of my control.
🔹 I was exhausted. Climbing the corporate ladder had been a great learning experience, but it was draining. The higher I climbed, the fewer opportunities there were. I had always envisioned myself as a Chief Merchant Officer at a major retail company, but let’s be real—there are only so many Fortune 500 retailers, and each one has just one CMO. The odds weren’t impossible, but they weren’t exactly inspiring either.
🔹 Job security wasn’t so secure. After being laid off, I spoke with older family members about what job security used to look like—back when companies and employees had long-term relationships. But times had changed. The idea that "hard work guarantees stability" wasn’t necessarily the case anymore.
Experiencing mass layoffs, company restructuring, economic uncertainty, slower growth, and unfulfilled professional potential has led me—along with many other professionals—to rethink my career path.
Welcome To This Blog Series: Making the Leap
Rethinking may lead to a big decision that has to be made. Maybe you keep working for a company. Maybe you consider entrepreneurship. Maybe you do both. Maybe you’ve already started exploring your own business on the side but aren’t sure if it’s the right time to make that full-time move. Maybe you’re unsure.
As you are weighing your options, consider these realities relative to entrepreneurship...
Entrepreneurship is different from corporate. It’s a different type of process and investment. And it’s not always easy.
Entrepreneurship isn’t for everyone. And that’s okay.
Through my company, 37 Oaks, I’ve coached, trained, and mentored business owners who have considered entrepreneurship or recently made the shift from corporate to entrepreneurship. I’ve spoken at conferences, led workshops, and developed programs designed to help these newly transitioned entrepreneurs break out of the “stuck” phase and turn their skills and passions into profits.
I won’t sugarcoat it—there will be challenges. There will be late nights, self-doubt, financial ups and downs, and moments where you question if you made the right decision. But there will also be freedom, growth, and a level of control over your career and income that is tough to get in a corporate environment.
I can’t make this decision for you. But what I can do is share the unspoken realities of entrepreneurship—the things I wish I had known when I was making that shift from employee to entrepreneur. There’s nothing wrong with keeping your business a hobby. There’s nothing wrong with waiting for the right time. But if you’re serious about making this shift, I want to give you practical, real-world insights to help you make an informed decision.
A few years ago, I wrote Prepare to Shift: The Workbook—a quick guide to turning your hobby or side hustle into a growing business. This workbook is built around 14 key principles: 7 MindSHIFT and 7 WorkSHIFT.
🔹 MindSHIFT focuses on the ways you need to think differently to transition into business growth.
🔹 WorkSHIFT highlights the actions you need to take to build a profitable and scalable business.
Each principle has an exercise to help you apply these shifts in real-time. Since this workbook is designed to help entrepreneurs move from stuck to scaling, you’ll see a few references to it throughout this blog series as it overlaps with key principles one needs to know before propelling a business into growth mode. It’s a quick but powerful read, so if you haven’t grabbed a copy yet, I highly recommend checking it out.
Looking back, there’s one game-changing realization I wish I had before making the leap—something that could have made my transition smoother and my success faster. In the second post of this Employee to Entrepreneur blog series, we’ll uncover one key factor that most aspiring entrepreneurs overlook. See you there.
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Who is 37 Oaks?
37 Oaks is an education company that prepares small business owners for growth in wholesale, e-commerce, storefront, and pop-up markets.
37 Oaks Offers...
Over 50 courses + study halls
Group + 1:1 coaching
Over 30 assignments, assessments, checklists, resource guides, and templates
Custom cohorts and boot camps
Small business support services
Monthly membership program
A community of like-minded
Learn more at 37oaks.com.
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