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Business Leadership Lessons from the Worst (and “Best”) Valentine’s Day Ever

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By: John Boggs
Updated: February 26, 2021

In the Face Embarrassing Failure, I Made a Difficult Choice & Unlocked a New Level of Business Leadership

On Valentine’s Day 27 years ago, I experienced both one of the lowest points in my life, as well as one of the highest highs! The business leadership lesson I learned in the aftermath of that experience has served my success for the past 27 years – and the biggest takeaway from that day’s emotional roller coaster can serve you, as well.

On that February 14, I walked into my boss’s office and received devastating news. “John, today is your last day as the sales manager of this team,” he said. “We’re going to let you go.”

Heartbroken scarcely describes how devastated and embarrassed I felt. It was Valentine’s Day, a day that should be exciting and full of fun and joy — and I’d just been fired from my job.

On one hand, it wasn’t a surprise. The job was a hot seat — challenging, demanding, with high expectations and the clear understanding that if you couldn’t produce, you wouldn’t be in the job for long. 

The previous four sales managers had lasted six months each. I had been on the job for — you guessed it — six months.

I was a new, young leader, and I just could not figure out how to succeed, no matter what I tried. Most of the people on the team were older than me. As a young leader, my level of influence with my team and my ability to diagnose what was going on and how to succeed were minimal. I hadn’t cracked the code in the six months I had been in the hot seat, so they were firing me.

To his credit, the owner of the company — my boss — offered me some hope. “We do appreciate your talent and skill,” he said. “We’re going to relieve you from your position as the lead, and you can stay on as one of the people working here.” 

I told him I appreciated the offer and that I’d give it some thought. Then I left the office.

In that particular moment, from a career standpoint, I was sad. My heart was breaking. I had wanted to succeed, yet I had failed in a fairly noticeable way.

But from a personal standpoint, however, there was a life-changing moment of clarity. 

As I was leaving the office, part of my mind was fixated on the loss I had just suffered. Yet a bigger part of my mind was focused on something more important — the woman I was dating, with whom I was madly in love. 

In that moment of heartbreak and loss, something hopeful shone through the darkness. I realized that I wanted to spend the rest of my life with her.

Has that ever happened for you? 

Have you ever been in a position where something that appeared to be devastating happened, yet it provided clarity about what was truly most important to you? 

I immediately drove to where she was — playing golf, which was one of the things I Ioved (and still love) most about her. She had just finished playing, and I said two things to her: “Babe, I just got fired from my job, and I’ve got a question that I want to ask you.” I got down on one knee and asked, “Will you marry me?”

Now, I’ll admit it’s not the most romantic way to get engaged, but it was my heartfelt, inspired way of doing it. To my delight, she said yes.

At the time, we were living in Cabo San Lucas. So we hopped on a plane and flew to Los Angeles to shop for an engagement ring. We had a wonderful, romantic, and fun weekend celebrating our engagement and thinking about our future together.

Top of my mind, of course, was the offer my boss had made. We spent a lot of time discussing what I was going to do. Could I really walk back into the office on Monday morning — to join the team that I had been leading?

My ego was screaming that I would be horribly embarrassed to be “just” a salesperson. I felt absolutely sick to my stomach at the thought.

My intuition had other ideas. As I thought about leaving the company to get a fresh start at another job, I recognized something important. I knew that I deeply wanted to lead. I recognized that leadership was my true calling.

This is where my intuition piped up. It whispered the suggestion that I stay and watch what the new leader did when he came in. If I could stay and observe, I might learn something that would make the difference for my future and long-term growth.

Think about that for yourself: What can you do to continue to grow and learn, so you get better every day?

I was more interested in getting better than I was in protecting my ego. That was a key lesson for me.

I decided to go back. I watched the next leader who came in very closely. I watched the moves he made that were different than the moves I made. I watch the way he influenced the team in ways I didn’t influence the team. I watched as his strategies worked, and he masterfully led our team to success. I picked up the lessons and tucked them away for future use.

Less than two years later, my replacement decided to move back to the United States. Once again, they tapped me with a new opportunity to lead that team. I led that team successfully — for the next 20 years. 

I had learned important lessons by watching my replacement, and I grew. As I applied what I had learned, I got promoted and ended up becoming a very successful leader in that company. It was all due to being willing to swallow my ego and put a greater value on learning and growing than on looking good.

The best part of the story isn’t my success as a leader with that company. It’s that this year, my wife and I celebrated an amazing Valentine’s Day. I recounted the story of the day I got fired and asked her to marry me, the day I hit an awful low and an incredible high within hours of each other. We’re in our 26th year of marriage now, and our relationship has grown stronger every year.

My hope and encouragement for you is that you’ll find love for yourself — and that you’ll practice love for yourself by staying connected to your intuition. Transformational leaders understand that their intuition is the voice of their inner wisdom and higher power. They learn to put their egos aside and make intuitive moves. I hope that you’ll adopt this powerful practice.

Have you ever made a tough move based solely on your intuition? I’d love to hear about it, so please tell me about it in the chat below. Intuition is powerful, and more we pay attention, the better we get at letting this wise inner voice guide us in making the right moves. 

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About John Boggs

John Boggs

John Boggs is an international award-winning executive with a passion for helping businesses develop tangible strategies for greater clarity, increased revenues and real success. Thousands of business professionals have benefited from his training and motivation. He has personally coached and consulted for executives with the World Bank, Johnson & Johnson, Toyota Motors, The Marriott Corporation, CitiGroup, and Century 21. Known by many as the ‘Action Man’, John helps us do what we know we need to do, no matter what challenges stand in our way.

Learn More About John Boggs

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