The Gift of Struggle (perseverance interview with Bobby Herrera)

Riley Smith
Content Contributor
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How the hardest times of our lives teach us how to persevere

Bobby Herrera is President of the Populus Group and author of The Gift of Struggle. He believes everyone deserves an opportunity to succeed, and he’s dedicated his life to bringing that philosophy into practice.

Bobby sat down with the hosts of REACH to talk about perseverance, grit, and what really matters when leading a community.

We hope his insights will fuel you, as they did us, to persevere in life, business, and your marketing efforts.

What does perseverance mean to you?

Beyond the technical definition, when I think about perseverance, I tend to reflect on the question …

When something is meaningful and important to me, what am I doing to make sure I have more grit than quit?

When we look around the world right now, I don’t believe there’s enough self-reflection on that important question. Do I have more grit than quit for the things that really matter for me?

It shows up in many ways for many people. For me, it’s a call-to-action. If this really matters to me, I must have perseverance. I must have more grit than quit to get to where I need to go and do whatever I’m trying to accomplish.

What motivates you to have more grit than quit? When you are struggling, what gets you to continue through it?

First off, let’s all agree, you’d have to be crazy to want to struggle. I don’t go around inviting it into my life. I’m like any other person. The flip side of that is, as much as you’d have to be crazy to enjoy struggling, you’d have to be even crazier to think it’s not going to happen. So over the years, I’ve embraced the struggle and become a student of it.

One moment in my life that still motivates me today happened when I was seventeen. It’s the first chapter of my book. I had an unexpected moment with a very kind, wise man. He did something simple for me that helped me reframe my story and look at my past differently.

That one kind act changed my life. It became something that over time gave me the hope that I’ve needed in moments of despair. Those moments when I’m thinking, “I don’t have it in me,” that one memory became my North star.

It’s helped me, because it gives me hope that one day I can check the Ultimate Box. The ultimate box for me is, “Will my story matter?”

In those moments where I have to dig deep, that’s a major force that drives me to find the will and motivation I don’t think I have.

What circumstances in your life today require that quality of perseverance to get you through?

I have a term that I use pretty frequently from my days in the army: VUCA. It’s an acronym for Volatility, Uncertainty, Complexity, and Ambiguity.

We can all agree that the last three years have been a bizarre chapter in our lives, and that it’s challenged us in ways that many of us would never have imagined experiencing. It required a lot of managing VUCA.

At any time in our lives, we’re going to have a certain amount of VUCA. Things that are volatile, uncertain, complex, or ambiguous to us. The way I respond to them is the way I was taught in the military, and it’s been reinforced throughout my life.

Slow the game down. That’s my biggest responsibility. Not only for myself, but for those around me that I’m serving.

When I’m faced with challenges these days, that’s what I try to do. I ask myself, “How can I slow the game down?” and that leads to locking in on what’s most important, and what can I edit out of my life that isn’t aligned to what’s important?

It also makes me look at the order that I need to do things. And it makes me ask the big question, “What can I control?”

We tend to spend our thinking on a lot of things that are out of our control, and most of the time, that leads to disappointment.

2022 is VUCA. Many business leaders are seeing a talent war out there that’s like nothing we’ve ever experienced. There’s a number of other challenges in the business landscape that’s like nothing we’ve ever experienced, not to mention all the things that are happening socially are impacting everything we do in business.

I’ve never faced this particular set of challenges before. So now is when managing VUCA really comes into play. I have to figure out how to slow the game down for myself and other people around me.

I have to ask those important questions, “What can I control? What order should I do it in? What else can I reasonably do?” And I need to simplify everything so I feel like I have a grip on my life and on the story that I’m trying to narrate for my business.

As a leader, you take responsibility for insulating your people from VUCA. Many folks do the opposite. What keeps people from taking on that role as leaders?

I heard this term from a really wise and well-known therapist, Laurie Gottlieb. She uses this term, “unreliable narrators.”

We, the human animal, are unreliable narrators of our own story. I think the biggest contributor to unrest within the business and social landscapes is the story we tell ourselves. We run a horror movie in our minds. The emotions may be real, but the facts probably aren’t.

My responsibility from a leadership perspective is to make sure that we’re all performing with the same group of facts within the same story. When I manage VUCA, I slow it down enough to make sure we’re all looking at the right elements of the story, and editing out what isn’t true, what isn’t relevant, and making sure we keep what is relevant and what we should focus on.

It’s super hard to do. It’s exhausting! It’s easier to let the horror movie run.

The horror movie is real, but the other more inspirational story is also real. So sometimes, leadership is introducing elements of the story that are being left out or are unintentionally not being considered.

Can you think of a time when you had a potential horror story running through your mind, when you thought things weren’t going to work out, but you persevered and it did work out?

I can think of countless times! But I’ll share a recent business experience.

When we were introduced to this bizarre chapter in our lives, everybody had to quarantine for the first time due to COVID. In a period of two months, my organization took almost a 40% drop in revenue.

To watch something that you’ve been building for eighteen years all of a sudden go into what you think is a G4 tail spin is very unsettling. It was a horror movie marathon!

But I went back to what I outlined about managing VUCA. The very first thing I did was introduce that term to my team and my community. Ever since, I’ve been a broken record: Let’s manage VUCA, manage VUCA, manage VUCA!

I think every business leader in America who faced a similar challenge and came through it, in their own way, was probably intuitively responding using this idea. I consider myself blessed that it was a lesson imparted to me many years ago that I was able to tap into.

Marketers often work as consultants, and in that capacity, there just isn’t time to learn all about, much less change, a client company’s culture. How do we make sure we’re doing the right thing for our clients, what they really want, even if we’re not totally aligned culture-wise?

When I engage the wisdom of someone external, someone outside my community, several things are important to me.

I ask myself, “How well do they understand the story that I’m narrating? Do they understand what it took to get where I’m at now? Do they understand the story now? Most importantly, do they understand the story that I want to continue to narrate for the next five to ten years?”

I want someone to approach me with a desire to understand every element of that story. Every entrepreneur is taught to use big words in business school. I simplify it. All we’re doing is narrating a story.

You have to do everything in your power to figure out how to get that story from here to the place you imagine. That’s one of the reasons I frequently use a mountain metaphor. There’s a summit that we imagine that looks and feels better than where we are today.

So I want whoever I’m working with to understand what it took to get me to this point on the mountain, and I want them to understand the peak that I’m going to.

Without knowing those two things, it’s really hard to guide someone. The only way to guide someone is to tell them the kind truth. That is, what they need to hear now, not what they want to hear.

I appreciate someone who is incredibly persistent in making sure I hear that kind truth. Quite frankly, I appreciate being told where I’m wrong. But do it in a way that helps me understand what about it will prevent me from getting to that summit.

Every business leader is not only writing a story, but they’re trying to guide their organization through some sort of transformation. As a consultant, if you don’t know what those two storylines are, you really can’t help.

How important are shared goals to persevering? And what is the role of community in that?

We all share three basic desires: to stand out, to fit in, and to be part of something bigger than ourselves. We have to be able to hit those three desires by understanding one another.

My purpose is also the core belief of my organization. We exist because I believe everyone deserves an opportunity to succeed.

That stems from that life-defining moment I mentioned earlier that happened when I was seventeen, and it’s a deeply embedded core belief.

Everyone that joins my community has to share that value. They have to believe in that core belief, but it doesn’t mean their passions need to be the same as mine.

They don’t have to be focused on paying it forward, giving back to other kids who were born on the wrong side of the opportunity divide, and assisting veterans. These are my passions.

They can have their own passions, do whatever they want to do with their generosity, but we have to share that same belief.

As for community, community frees us from the gravity of having to do something totally on your own. And it keeps us grounded.

If you surround yourself with the right people, they’ll tell you what you need to hear, and what you need to do to behave appropriately and remain a member of that community.

A community should allow different mindsets, different thought processes, different ways of thinking and seeing things, but it should be absolutely unwavering in their commitment to the same values.

So for example, our community’s three pillars that guide our culture are:

  1. We give more than we take.
  2. We speak from the heart.
  3. We go off the beaten path.

If you want to be a member of our community, you must do those three things consistently. If you can, you’re going to do great here. If you’re not willing to do those three things, you’re going to be miserable, and we’ll let you know that you’re going to be happier somewhere else.

We don’t try to be all things to all people. We tell them, “This is what it takes to be part of our community, to be successful here, so we can do some good together. But if that’s not of interest to you, it doesn’t mean that you’re a bad person. It just means you’re not the right fit for our community.”

How do your beliefs about perseverance change the way you manage your team?

I call my employees “climbers,” because of that mountain metaphor we talked about earlier. I have a climbing theme in my community.

As part of that, and I have this conversation a lot with my kids, too, but we think we want easy. We don’t really want easy.

We think we don’t want to struggle, but if we didn’t have it, we’d be bored out of our minds.

So we’re a contradiction. That’s right in the heart of perseverance. It’s that tug-of-war between thinking we want easy, and really wanting the right kind of challenge.You have to make a choice: “I don’t want easy. I need to participate in my own rescue here. Let me do it.”

When I coach CEOs or have a conversation with fellow CEOs, one of the first questions I always ask is, “What does the E in CEO stand for?”

They’ll kind of look at me like a puppy, with their head cocked to the side. They know it’s a trick question so they give me a few creative answers.

Then I tell them, “In my opinion, it stands for Chief Editing Officer and Chief Encouragement Officer.”

So in other words, every conversation you have with a member of your community, how are you encouraging them? How are you helping them to “edit,” or simplify their life? It’s our responsibility to help people through their struggles.

In any conversation I’m having with a member of my executive team, I am in intense editing and encouragement mode. I think that’s applicable regardless of what title you hold. Whatever leadership role you have, you should be looking to edit, and looking to encourage.

Often, when we trust an employee, good intentions get in the way, and the opposite happens. You either ratchet up accountability and standards or you’re putting more on their plate. The last thing they need is more.

If you want your people to persevere, ask yourself, “How am I editing? How am I encouraging them? Am I doing that well and as a regular part of the process?”

Anyone can do this self-assessment, and that’s leadership.

I enjoyed meeting you guys, I’m grateful I got to be a part of your journey with this.

All hail the underdogs!

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We’re diving even deeper into Perseverance on our podcast, REACH, where we explore the mindsets of high achievers and then seek to apply the lessons to life, business and marketing.

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