318: How to Make Life One Big Game Show with Rich Bracken

What does “killing it” actually look like behind the scenes? Because sometimes it’s a huge stage and an incredible opportunity. And sometimes it’s a soggy airport sandwich, a missed flight, or admitting that something just isn’t working.

In this episode, Erin sits down with speaker, author, and emotional intelligence expert Rich Bracken for a chat about the side of success we don’t always talk about (or get to hear). They dig into why we’re so quick to measure accomplishments but ignore how we actually feel, the power of being honest about failure, and why vulnerability matters more than maintaining the appearance that everything is fine.

Rich also shares his “Theory of Why Not,” the mindset that has led him to take some pretty wild chances throughout his career, and why meaningful progress usually comes from consistent effort rather than trying to knock it out of the park every single day.

Here’s what you’ll hear:

• Why your feelings deserve as much attention as your metrics
• What the polished version of “killing it” leaves out
• How asking “Why not?” can lead to unexpected opportunities
• Why small, consistent effort is more powerful than perfection
• How vulnerability, curiosity, and genuine care make us better leaders

Connect with Rich on LinkedIn

Learn more at richbracken.com.

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DISCLAIMER: This episode is not explicit, though contains mild swearing that may be unsuitable for younger audiences.

Tweetable Comments

“The feeling is data, too.”

“We all want to feel seen and heard and respected, so show that and you’ll get it back.”

“If you put the other person first, everything else unfolds the way it should.”

“The best leaders I ever worked for or worked with were human beings. They were vulnerable, they were honest, and they cared.”

Editor’s note: This transcript has been edited for clarity and length while preserving the substance and conversational tone of the original discussion.

Erin Hatzikostas sits down with speaker, author, coach, and emotional intelligence expert Rich Bracken to talk about what success really looks like behind the scenes. They explore emotional intelligence, vulnerability, failure, leadership, consistent effort, Rich’s “Theory of Why Not,” and why some of the biggest opportunities in your career can start with simply being willing to take a chance.

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Success Is More Than a Metric

Erin: I want to start by reading something from your book because this took my breath away. You wrote, “The most dangerous blind spot in change management isn’t a missed metric. It’s individual and group satisfaction. That’s the left hook nobody sees coming. We get so obsessed with what we can measure that we stop paying attention to what we can’t. The feeling is data, too.”

You talk about how we want everyone to believe everything is fine. We hit the number. It worked. We never heard no. Admitting that we came up short or something didn’t work can feel like weakness, so we skip past it. We’re much quicker to share our wins than our failures.

And that instinct doesn’t just apply to metrics. It applies to how we feel. We hide emotional shortcomings the same way we hide missed targets because vulnerability in either form feels like exposure.

Rich: I think we need to chip away at this idea of perfection because, number one, it doesn’t exist. Nobody is going to be perfect. Nothing is ever going to be perfect.

The more people admit their failures, admit their shortcomings, or admit that something went wrong, the more honest we can be.

I lost a contract the other day that was devastating to me. It was going to be huge for me. And the first thing I thought was, “I’ve got to talk to somebody about the failure.”

It’s one thing to say everything is great and trucking along, but when those left hooks come, sometimes you need somebody to grab you and lift you off the ground. It’s tough.

Erin: I think this applies to people at every level of their careers. We get asked all these metric-driven questions. How many talks did you do? How much business did you bring in? What did you accomplish?

My goal is two or three talks a month. That translates to around 30 talks a year, and I freaking love that. I don’t necessarily want 100 talks a year.

And when people ask how things are going, in general I’m like, “My life’s fucking awesome.” Not just because I’m hitting a number. My life in totality is great.

We spend so much time talking about how many. Maybe we need to talk more about how it actually feels.

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What “Killing It” Really Looks Like

Erin: Let’s talk about “killing it,” because when we met, we immediately started laughing about what people think success looks like versus what it actually looks like.

What’s an example of “killing it” for you?

Rich: There are so many.

If killing it looks like sorting through which airport sandwich is the least soggy because everything else is closed and I’ve missed three flights, then yes, I’m killing it.

Does killing it look like sitting in front of my computer cursing because I can’t find the last version of a presentation I worked on?

Is killing it putting your PowerPoint into Google only to have your client download it and suddenly the font looks like Wingdings?

That’s the part people don’t see.

I love what I do. I wouldn’t trade it for the world. But I think the closest comparison to a professional speaker’s life is a touring musician. It’s exhausting. You’re traveling constantly. You’re dealing with airports, weather, schedules, flights, hotels, and all of these things happening around the glamorous part people see.

Erin: The facade is cool, though.

Rich: Absolutely. And sometimes it really is cool.

I’m about to speak in front of nearly 10,000 people. I have custom lighting. I have a walk-up video. There are going to be glow sticks, music, singing, dancing. It’s going to look like I’m a rock star.

But somebody asked me, “What are you going to do for the rest of the day?”

I said, “I’m going back to my room, curling up in a ball, and not talking to anyone.”

That’s what killing it looks like too.

I know I’ll walk off that stage on cloud nine, but I’ll also be completely empty. I’ll need to refuel.

Erin: I have plenty of those stories too.

Killing it was somebody reaching out to ask me to endorse a book, and then realizing they had confused me with the author of a completely different book.

Killing it was getting what I thought was fan mail asking for my autograph six months after starting the podcast, then realizing somebody was probably trying to get my signature for fraud.

Killing it was putting together footage for my speaker reel and discovering you could see my underwear when I turned around onstage.

That’s the behind-the-scenes version.

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Small Steps Can Change Your Entire Life

Erin: One of the foundational stories in your life is losing more than 100 pounds. Tell us about that.

Rich: I was a rail-thin kid and played sports year-round. Then I was diagnosed with exercise-induced asthma. I’m my parents’ only child, so my mom basically said, “Stay inside, eat whatever you want, and play video games.”

I went from being outside constantly to being inside constantly, and I started putting on weight.

By middle school I was the heavier kid, and I got teased quite a bit. Football became a saving grace because being bigger suddenly gave me an identity. I was an offensive lineman. I was the protector. I opened opportunities for the running backs and helped keep my friends safe.

I eventually played a year of college football. Then I quit, and that identity disappeared.

The eating habits stayed, but the workout habits went away.

I got up to about 260 pounds. I fell into this really low self-esteem mindset. I didn’t like what I saw in the mirror. I was miserable.

Erin: Was there a specific moment that made you decide to change?

Rich: It sounds silly, but I got tired of pulling my shirt away from my body.

I was constantly adjusting it because I was afraid of my body showing. I was exhausted. I didn’t have energy. I was depressed. I didn’t want to do anything. I wasn’t social.

I finally had my diet analyzed, and everything was off the charts. Cholesterol, calories, fat, everything.

My health instructor gave me something incredibly simple. He told me to replace certain foods with better options, eliminate fast food and carbonated drinks, and walk one mile a day.

That was it.

I didn’t need to change everything overnight. I didn’t need three hours of cardio or two hours in the gym.

I just needed to do something small and see progress.

Eventually I went from a 40-inch waist to trying on a pair of 34-inch pants in an Old Navy dressing room and screaming because they actually fit.

Those moments taught me that I could change something huge by consistently doing small things.

It transformed my life because I started to believe I could take on other things too.

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The Theory of Why Not

Erin: That leads really naturally into something you call your “Theory of Why Not.” What is it?

Rich: I tell people all the time that I have the most ridiculous life résumé of anybody I’ve ever met.

The things I’ve done, the people I’ve met, the situations I’ve put myself in, all of those experiences come back to the theory of why not.

Why not give it a shot?

Why not me?

Why not try it?

The worst you’re going to hear is no.

I don’t ever want to die with all these ideas that might have been great, but I never acted on them.

So many people are afraid to try because the possibility of failure exists.

They don’t want to say, “I want to do this thing,” because what if it doesn’t work?

The Theory of Why Not is about getting out of your own head and getting out of your own way.

I’ve been on several game shows. I’ve also missed several other ones because I took a chance on them and didn’t get picked.

I’ve had speaking opportunities, business opportunities, media opportunities, and all kinds of experiences. The ones people see are great.

What we don’t talk about are the dozens that didn’t happen. The dozens of no’s. The dozens of, “You’re nice, but...”

Those are the things we’re terrified of.

But I can say I’ve lived a very full life. If I went away tomorrow, I went for it.

If you continually talk yourself out of opportunities, dreams, lofty goals, or ridiculous ideas, you’ll never know what could have happened.

Sometimes you have to ask, “Why not? What’s the worst that could happen?”

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Taking a Chance With a Mix CD

Erin: What’s an early example of you living this way?

Rich: When I was in graduate school, I had the opportunity to study in England. I was also DJing, and one of the top radio stations in the country happened to be about two blocks from where I lived.

For those of you under 40, brace yourself.

I took my mix CD to the radio station.

I basically said, “I’ve loved the English music scene for years. It’s one of the reasons I’m a DJ. I just want to know what you think. Am I any good? How do I stack up?”

I told them, “If you hate it and never want to talk to me again, that’s fine. At least I took the shot.”

Three days later, the station’s marketing manager called me.

She said, “You told me you have half-day Fridays and a rail pass, right?”

I said yes.

She said, “Great. We’ve booked you for six opening slots at different clubs around the country, opening for some huge DJs.”

All because I walked in and handed somebody a CD.

I wasn’t expecting that. I just wanted feedback.

If I had never raised my hand, I never would have known.

Some of the coolest things I’ve ever gotten to do happened because I was willing to take that kind of chance.

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Opening for Avicii and Going on Game Shows

Rich: Another great example was auditioning to open for Avicii when he was one of the biggest DJs in the world.

I was competing against people who were DJing regularly. I had a corporate job and was DJing on the side for fun.

But I believed in my style. I believed in my energy. I believed I could earn that spot.

So I auditioned.

I got picked.

I ended up opening for Avicii in Kansas City in front of thousands of people. It was phenomenal.

That same mindset has led me to game shows, television, speaking, and writing a book.

I was on $100,000 Pyramid. My partner was Von Miller, who had just won the Super Bowl and was the Super Bowl MVP.

Usher was also there. He was a terrible game show teammate.

Erin: Was he?

Rich: Terrible.

I was also on a reality show on ESPN, and I competed to host another television show. I made it to the final four and didn’t get the job.

But it was still an incredible experience.

My ridiculous dream job is to host The Price Is Right someday.

And the funny part is, because of one of the shows I was on, I’m now one degree of separation from that job.

That alone is the Theory of Why Not.

Erin: You’re making me think I need to go on a game show.

Rich: Why not?

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The Biggest Lesson Rich Learned From Being a DJ

Erin: You DJed for a long time. Now you speak and coach executives, speakers, and professional athletes. What did being a DJ teach you that translates into what you do now?

Rich: Two things.

The first is self-awareness and self-confidence.

People think DJing is just standing there pushing buttons and playing music, but there’s an art to it. You’re exposing yourself creatively.

And if something goes wrong with the music, sound, or song choice, you can’t hide. You’re the person standing there controlling everything.

Confidence, self-awareness, and believing in what you’re creating matter.

The second lesson is that it’s not about you.

One of my favorite pieces of advice is, “You’re not more important than coffee.”

If an event has to choose between having coffee or having a keynote speaker, you’re probably gone. They’re picking coffee.

Erin: They’re definitely picking coffee.

Rich: But the bigger point is this: whether you’re a speaker, leader, salesperson, attorney, professional service provider, or anyone else, if you put the other person first, everything else unfolds the way it should.

I’ve seen speakers go onstage and make the entire thing about themselves, their show, and their ego.

It bombs.

When somebody gets up there to truly engage the audience, help them, and serve them, people feel it.

The same thing happens with DJs.

And the same thing happens if you’re pitching a client or running a team meeting. That’s an audience too.

If you show up with confidence in what you’re doing, but your number-one priority is helping the people in front of you, that energy speaks for itself.

You’ll build better relationships and connect with people differently.

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Every Meeting Is a Stage

Erin: That translates directly to people in traditional corporate roles too.

You can walk into a board meeting, staff meeting, presentation, or one-on-one and feel that same stage fright.

You start believing perfection is the game.

But even if you’re the person leading the meeting or walking everyone through the PowerPoint, it’s not about you.

How do you make the other people feel?

How do you make sure they’re engaged?

Rich: Exactly.

And it’s hard to fake.

People need to spend time off the stage thinking about what they do, why they do it, and how they help people.

Your “stage” could be a boardroom. It could be a speaker stage. It could be a DJ booth. It could be whatever auditorium your profession puts you in.

When you’re serving people and helping people, you make them feel good, but you also feel better because there’s meaning behind what you’re doing.

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Behind the Successful Face

Erin: You’ve coached CEOs, speakers, professional athletes, and even celebrities. What trips people up behind closed doors that might surprise us?

Rich: Deep down, we’re all a little insecure.

We all second-guess ourselves.

We all deal with some level of, “I don’t know. I’m not sure. Why me? Can I do this?”

People put their successful face on for the world, and we forget they’re human.

People get hurt. They fail. They get scared.

I’ll coach somebody who looks incredibly successful from the outside, and then behind the scenes they’ll say, “I don’t know,” or, “I tried this and it didn’t work, and it really hurt.”

I think one of the reasons I connect with people is that I treat everybody like a human being I care about.

When you do that, you connect differently.

When a relationship is transactional and you’re clearly after something, people can smell it like a shark smells blood in the water.

Serve people first.

Reach out genuinely. Ask questions that show you actually give a damn about who they are as people.

We all want to feel seen and heard and respected, so show that and you’ll get it back.

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Consistency Beats Trying to Knock It Out of the Park

Erin: You’ve kept the weight off for 27 years, so obviously consistency has been a huge part of your life.

What do people misunderstand about consistent effort?

Rich: We have this idea that every time we do something it has to be some knock-it-out-of-the-park experience.

That’s not accurate.

Let’s say you want to get back into working out.

If you go stretch for three minutes, that’s something.

If you do a one-minute plank, that’s something.

If you walk for five minutes, that’s success.

That is consistency of effort.

There are days I feel great. I’m working out, I’m listening to music, and everything clicks.

There are other days when the last effing thing I want to do is lift a weight.

If I do 10 minutes on one of those days, I can call it a success.

At my level of energy and care in that moment, doing something is a win.

I don’t slay every workout.

Sometimes I get up intending to work out and realize I’m not going to do it well. So instead of beating myself up, I shift my mindset and say, “Today I’m going to deal with whatever garbage is holding me back, and tomorrow I’m going to show up better.”

Erin: I think the other part of consistency is choosing the thing you’re actually likely to do.

People ask, “Should I ride a bike? Should I run? Should I walk? Should I lift weights?”

Pick the thing you’re most likely to keep doing.

I was just talking to my son, who is trying to grow his speaking platform. He said he needed to figure out the marketing stuff.

I gave him a bunch of options and then told him, “You have to pick the thing that actually excites you.”

All of these things can work, and all of them can fail.

Pick the thing you’re most likely to consistently do.

The same applies to leadership.

Leadership can feel like you’re supposed to read 72 books and do 80 things every day.

What if you picked one thing you were going to consistently do instead?

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The Best Leaders Are Still Human

Rich: As people move up in organizations and take on more responsibility, they often become more visible, more guarded, and more concerned about the impact of their decisions.

At the same time, there are so many corporate experts and thought leaders telling people how they’re supposed to lead that we start thinking we need to show up like Simon Sinek, Mel Robbins, or somebody else every day.

The best leaders I ever worked for or worked with were human beings.

They were vulnerable.

They were honest.

And they cared.

I’ve worked for great bosses, and I’ve worked for dumpster-fire bosses.

The stark difference is that the great ones cared and stayed human.

Read the books. Listen to the podcasts. Go to the seminars.

But don’t lose track of why you’re doing what you’re doing or what makes it meaningful and fun for you.

Erin: I’ve joked that from a traditional Leadership 101 perspective, I’m probably a B-minus.

I’m not a great planner. I might walk into a meeting without an agenda. I don’t always package feedback perfectly.

But I always felt like authenticity was this trump card.

It didn’t wipe away every mistake, but if you can set aside your ego, be honest, show humility, and genuinely care about people, that covers a lot.

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Being Good at the Job Does Not Automatically Make You a Good Leader

Rich: One mistake organizations make is assuming, “This person is really good at the thing, so we should make them the leader of the thing.”

You’re a great salesperson, so we make you a regional sales director.

You’re a great marketer, so we make you the chief marketing officer.

That doesn’t automatically mean you’re going to be a great leader.

Sometimes people don’t even want the leadership job, but they feel guilty saying no because it comes with more money, credibility, or status.

Organizations need to become better at identifying who actually wants to lead and who has the potential to do it well.

And once you become a leader, the job changes.

If you’re a regional director of sales, you aren’t primarily selling anymore.

You’re guiding and coaching other people to become better salespeople.

It’s literally a people job, not a thing job.

I coached somebody once who kept saying, “I don’t understand why they don’t do this. I don’t understand why they complain about that.”

And I said, “Ask them.”

Ask them why they’re not motivated.

Ask them what they need.

You’re their coach.

The coach of a football team isn’t running onto the field and playing with the seventh graders. The coach prepares them to play.

That’s what leaders do.

It’s about serving your people.

And you have to remember that what worked for you may not work for everybody.

Different people require different communication, different motivation, and different support.

As a leader, you need to ask questions, become more socially aware, develop trust, and understand the nuance of each person on your team.

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When “Why Not?” Means Trusting Your Judgment

Erin: We ask every guest about their “Buck That” moment. What’s a time when you went against what was expected, felt a little uncomfortable doing it, but good things happened because of it?

Rich: I was working at a law firm doing business development, and one of the attorneys and I identified a huge business opportunity.

It was going to require some extra work and a little thinking outside the box, but we mapped out a path to make it happen.

I went to my CMO and explained the idea.

She said, “Absolutely not.”

She didn’t ask a single question.

Not, “Tell me more.” Not, “What could we gain?” Not, “What would this take?”

Just no.

I was pissed because I felt like the idea had been dismissed without any curiosity.

Now, I’ll do crazy things and take chances, but I’m also calculated about it. I’m not reckless.

I had really thought through this opportunity, and I believed it would work.

So I did it anyway.

I recruited a few people who were willing to help me after hours. We got the project finished ahead of the deadline and launched it.

Eventually my CMO appeared in my doorway holding a printed copy of the email announcing the initiative I had been told not to do.

She said, “What is this?”

On the outside I was very apologetic.

On the inside, I was thinking, “Ha.”

She was absolutely livid.

But two things happened.

The attorney I partnered with ended up getting national recognition in The Wall Street Journal and Bloomberg and became a recognized expert on the subject.

Later, after I had left the firm, he called me.

He had just signed the biggest deal in the firm’s history.

He told me, “I just want to thank you for sticking your neck out. You believed in me and you believed in this project.”

I’ll never forget that.

I’m not advocating complete rebellion.

But sometimes you have to trust yourself enough to recognize that you’ve thought something through and you know what the right move is.

Sometimes you need to do what’s right for the business, but do it your way.

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Make Work Suck Less by Finding a Way to Have Fun

Erin: Last question. What’s one thing people can do to make work suck less?

Rich: Find a way to have fun.

Even if you’re sitting there thinking, “I’m an accountant. How?”

One of the things I do with audiences is build playlists together. Everybody scans a QR code and submits a song that makes them happy.

The playlists are hilarious and amazing.

Then I send the playlist back to the company and tell everybody to keep the link.

When you need five minutes of happiness, five minutes of energy, or five minutes to shift your mood, go to the playlist and pick a song.

It may not even be your song, but somebody you work with chose it because it makes them happy.

Try something new.

Take five minutes.

Have the ridiculous singing and dancing party in your office or cubicle if that’s what makes the day better.

There is always a way to have more fun.

You just have to figure out what that looks like for you.

Erin: Why not?

Rich: Exactly. Why not?