Entrepreneurs

How (and Why) I Make Grown Men Cry

Is the legacy you're building the legacy you want to be remembered?
How (and Why) I Make Grown Men Cry
Image credit: shironosov | Getty Images
Guest Writer
Reputation management and personal branding expert
5 min read
Opinions expressed by Entrepreneur contributors are their own.

I remember the first time it happened. I met with my client in a coffee shop because he didn't want to meet at his office for this conversation. I’d prepared for the healthy and hearty discussion about his career and personal goals, and dove right in.

He’d engaged me to help structure and direct his personal brand and reputation, so I began with a series of career-focused questions. What do you perceive are your greatest strengths? How do you differ from your competitors? What has helped you succeed? These basic questions help establish a reputational baseline from which we could build his personal brand.

Related: 5 Powerful Branding Lessons From 'Fuller House' Star Candace Cameron Bure

Then came the harder questions: How do you want others to remember you at the end of your life? What would you like your legacy to be? How will you have impacted those around you? What do you see as your purpose for being here, now?

And his tears started to flow.

Perhaps it was my upbringing or my societal conditioning, but I didn’t expect to see this grown man cry before me. His tears and raw emotion took my breath away -- and slightly worried me. What if I’d embarrassed him, here in this coffee shop while customers worked and chatted and baristas foamed hot milk behind their counter? Would he be mad?

But the opposite happened. My client shared his deep feelings and then pulled himself together. We concluded the session and followed up with ongoing monthly sessions. And here’s the interesting thing. This heartfelt response from my client didn’t remain unique. As my client list grew and I helped business leaders and professionals with their reputation and brand, I’ve found almost everyone wells up with tears to the questions around their legacy -- especially men.

In the same way, when I coach transitioning military on repositioning their brand in the civilian world, I see brave and experienced men who fought for our nation well up with emotion in the same way the CEO did at the cafe. I’ve seen this response in all kinds of professions and across industries and geographies. Even when hosting workshops on building brands and personal reputation, once I touch on how others will remember us, participants sometimes become overwhelmed with tears and leave the room. “I’m not ready to go there,” one attendee wrote to me after. “I’m not ready to think how I want others to think of me when I’m gone.”

Related: How to Build Your Confidence and Create the Reputation You Want

Why the tears?

So what’s going on? Why does thinking about our legacy -- and the finality of our time on Earth and how we can make an impact -- cause grown men to cry?

I suspect it’s two-fold. First, thinking of your legacy means thinking about how people will remember you after you’re gone. No one really wants to think about the morbid finality of that. It’s tough. Even if you feel happy with how people will remember you and are content with your personal brand and reputation, it’s hard not to get a little weepy when that topic surfaces. No one really likes to think about it.

The second part of the tears, I believe, comes, in larger part, from when the legacy you’ll likely leave misaligns with the one you want to leave. That disconnect becomes a tough pill to swallow, especially if you’re older. Maybe your wife and kids will remember you as a workaholic. Maybe your team won’t view you as charitable or the most understanding manager or just not an overall good person. Or, maybe you feel solid about your leadership and character; but you never pursued your childhood dreams -- your true calling. And now, I’m asking this person to think about how people will remember them when they’re gone, and the reality of that suddenly hits them. Pretty sobering.

But here I can happily tell them: It’s not too late. It’s never too late to work on changing the legacy you want to leave, your personal brand and your reputation. You can chang how you will be remembered once you’re gone.

Related: These 5 Entrepreneurs Can Show You the Way Personal Branding Should Be Done

How focusing on legacy helps us succeed.

From these encounters, I’ve gained powerful insight into what drives us to succeed. To build a personal brand that is significant, sustainable and scalable, it must come from a place of authentic and meaningful passion. Tears reflect this depth of authenticity. In the 10 years I’ve consulted leaders on reputation and brand, I can point to when the branding hasn’t been as scalable. The level of emotion simply isn’t there.

Even today, I still ask about legacy in that first session with a new client, but I insist we meet somewhere private with no spouse, PR team or lawyer present. That way, if the tears overwhelm, the privacy offers dignity and comfort.

I see results from this approach. Many describe the first session of my process as "absolutely amazing." Many feel inspired with revelations and ideas. Then, together we build a meaningful strategy to attain the legacy they seek. I still get taken aback when the tears come, but I feel honored someone trusts me enough to be real and vulnerable. They’re thinking about something that makes them feel exposed. Having a vision for the end gives you power today. Determining your legacy changes business models, the people you surround yourself with, sometimes even the work you do. Legacy changes everything.

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