It’s a familiar idea that shows up often in movies and TV shows: the corporate employee who decides in the spur of the moment to quit their job and chase a dream. In reality, the process is often a lot more complicated. I see it a lot with my franchise candidates, and I experienced it myself.
Especially when you’ve poured 20 years of your life into a company, you make a good income, and you have great benefits, leaving the corporate world can seem rash at best and stupid at worst. What changed my mind? A series of moments that stacked up until staying felt harder than going. Part of what did it: five specific conversations I had with the people around me. Keep reading to see if any of these feel familiar, and what they can tell you about whether you’re on the right track.
The Conversation With My Boss
I met with my boss one day to talk about my career trajectory. I had worked my way up to the first rungs of the executive ladder, and I’d been given the impression that I was on track for the C-suite. With a particularly good year behind me and a few years under my belt in my role, I wanted to know what the timeline was for my next step.
My boss’s answer? “You’re doing great work, Dave. But the promotion timeline is…fluid.”
What he really meant: keep grinding, and we’ll see. The company wasn’t prepared to commit to my success or really invest in my future. In other words, I needed to take care of those things myself. As the yellow flags piled up and I looked back on this conversation, I realized that I had been waiting for permission to build my own future.
The Conversation With My Laid-Off Friend
I got a phone call one afternoon from a good friend who’d been at the same company for 22 years. He’d worked his way to a corner office and was an incredible contributor to the company’s bottom line. Always met or exceeded his KPIs, deep institutional knowledge, excellent rapport with his team and with the C-suite.
And he was gone in 15 minutes. The times, they were a-changing, and the company just didn’t have a place for him anymore. He called from his car, still holding his security badge that didn’t work anymore. “I thought I was different,” he said.
That was a real wake-up call for me. I realized that, despite all the wins I’d notched for my employer, it could all become irrelevant in an instant. A simple change of leadership or a bad economic downturn, and it would be just as easy for those above me to decide it made strategic or financial sense to kick me to the curb.
The Conversation With My Wife
My successful corporate career would not have been possible without my wife, Lauri. She kept our home and family running smoothly as I climbed the ladder and moved us around the world. Her support was key to my confidence and ability to focus. But even as she supported me, she could see the toll from those 60-hour weeks and constant moves – both on me and on our family.
So one night at dinner, she asked me a simple question: “If you work this hard for another 10 years, what will you actually own?”
I didn’t have a good answer. In fact, at first, I didn’t really understand why she was asking me that. I made an excellent income. Had a retirement account with a hefty balance. My salary and benefits provided excellent financial security for our family – or that’s how I thought about it at the time.
But the more I replayed that conversation in my head, the more I realized she was thinking about real financial security. She was also thinking about fulfillment and freedom. She knows me better than anyone, and she knew I would be happier building something I owned, with the full benefit coming to our family.
The Conversation With Myself
It was 3am, and I was wide awake, staring at the ceiling. I couldn’t escape any longer from the internal dialogue I’d been avoiding. For a while, I’d been thinking about the possibility of leaving the corporate world to be my own boss. But I was scared. Scared of giving up that good salary and benefits, scared I might fail and have to go back to the corporate world with defeat on my shoulders.
That night, I finally asked myself the question I should have asked the first time I felt that twinge of panic: “Is this fear protecting me or trapping me?”
Our brains are wired to feel fear at anything new. It’s an evolutionary response from the days when “new” might mean a wild animal about to attack or a hostile tribe moving in our territory. Most threats today aren’t existential, so our fear response is often overblown.
Once I had this conversation with myself, I realized I could rationally answer my fears. Yes, I might lose some money on a failed business. But it would be a survivable loss. Yes, I might not know just what I was doing at the start. But I had decades of successful leadership and operational experience – I could figure it out. Fear was not helping me in this situation. It was holding me back from a better future.
The Conversation About AI
At the time, we called it “automation.” Especially working in the automotive industry, I heard the term often. Historically, it was about the switch from craftsman-style construction to assembly-line manufacturing. Then it was about bringing in robots to do some of the mechanical labor. Finally, it became about super-smart software that used algorithms and deep learning to handle white-collar tasks.
I was talking with a colleague one day when he mentioned that his team was being “restructured” because automation could handle 60% of the workflow. He was going to have to lay off a significant portion of his team, and he wasn’t completely confident about the future of his own job.
Walking away from that conversation, I had a lightbulb moment. No one can automate ownership. You can’t “restructure” equity. The only true job security left in our economy is to own the asset.
Taken on their own, none of these conversations told me everything I needed to do. I didn’t even realize the true significance of some of them right away. But over time, the cumulative lessons were impossible to ignore. And ultimately, they became pieces in the puzzle that came together in my mind. I realized I could keep building someone else’s empire, or I could start building my own.
Now, I help other corporate executives who wrestling with the same questions and conversations. What do you really want for yourself? For your family? Is the corporate world really providing the freedom and financial security you crave? Do you feel able to fully tap into your skills and possibility where you are?
I can help you answer all these questions, and more – and my services are completely free. Let’s the get the conversation started with a 20-minute call. Book some time on my calendar today.
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