Ep. #36: How to Do Big Scary Things

Everyone wants to succeed, but few people achieve it because they’re not willing to do the big scary thing. The only thing standing between you and success is the ability to do the big scary things. Listen to this episode to learn how to do them.


Welcome to Rich & Thin™ Radio, the only podcast that helps you get more bank with less bulk. Today’s episode is for every listener who is struggling with that age old dilemma of going big or staying small. I’m Kelly Hollingsworth and if this is something you’re wrestling with, I’m glad you’re here because today we’re going to talk about some tools for getting past it.

I’m thinking about big vs. small this week because I was working with a client who is poised on the brink of business success. We’ve developed her offer, and we wrote a compelling message that describes it. And now it’s time to get out there and deliver the message. It’s time to contact people and see if she can speak in front of their groups and organizations.

But she feels paralyzed. She feels terrified. Why? It’s not because she’s afraid the message won’t land. We know it will, because when she tells people about what she’s doing in casual conversation, they are effusive in their praise on what a great idea it is. New acquaintances are volunteering all the time to introduce her around so that more people can learn about it. People who hear about this are telling their that they need her and they want to hire her. You can always tell when something truly resonates vs. when you’re just getting a polite response, and we know that her message is dialed in, so what’s the problem?

The problem is that it just feels too big. It feels like she’s poised on the brink of too much money. Too much responsibility. Too much success. Too much of everything. And when it feels this way, the way she describes this is by saying, “This is just so big.”

She’s at a very common place. It’s one thing when the work is in our heads or it’s happening in private. It feels contained then. It feels manageable. But when we think about actually taking the message out in front of others, that’s when things start to get real. That’s when it can start to feel too big and too scary, and that’s when we often get stuck.

Whenever you’re stuck, that’s a sign you’re in a coaching opportunity. At every stage of achieving a successful business, we must manage our minds around the thing that’s tripping us up, around the next obstacle. When we’re developing the offer, we have to manage our minds. When we’re writing the message, we have to manage our minds. And when it’s time to go out and deliver the message, we really must manage our minds because this is when we leave the theoretical and bring the business out into the real world. This is when things get real and it can feel like things are loom too large. It’s when we begin stepping out of what we see as the smaller role, and into the bigger role.

What I want to offer to everyone who’s feeling paralysis at this stage is to go and see the movie A Star is Born. The current, 2018 version. Not one of the prior films. This year’s version stars Bradley Cooper and Lady Gaga, with Bradley Cooper also directing. In the movie, he plays Jackson Maine, an aging rock star who’s swimming around in a bottle of booze. He’s being chauffeured away from a concert of his one night when the bottle runs dry. He’s desperate for more alcohol so he ducks into the nearest neighborhood watering hole to get it. It turns out to be a drag bar, and Lady Gaga is there. Her character is named Ally, and she’s a waitress who’s all but given up on her dream of becoming a singer/songwriter. She’s been told that her songs are good, but her nose isn’t right and she’s not beautiful enough to perform for big audiences. So when we first encounter her in the film, her career is confined to singing once a week at this drag bar where she used to waitress, and Jackson Maine enters the bar just in time to be mesmerized by her performance of La Vie en Rose, which is a French song about a woman who finds new love after going through a trying time.

The two of them collide in a cataclysm of chemistry and artistry. The energy between them just crackles in this film, and if you see no other movie for the rest of your life, go see this one. It’s pure art. I saw it this weekend and when it was over, everyone in the theater just sat there in the dark. We were silent, motionless, just watching the credits roll. I don’t think anyone even knew what to do, until finally one man in the audience swore out loud, so loud everyone in the theater could all hear it. He said something that I won’t repeat on the podcast, but he was basically conveying, Wow, that was amazing, and everyone else started laughing and applauding. It is such a powerful film, for I think everyone who sees it, but I think it’s an especially powerful film for entrepreneurs who are struggling with the mental debate of going big vs. staying small.

One scene I’d suggest for all struggling entrepreneurs to pay particular attention to is the one where Ally is standing backstage at one of Jackson’s concerts. They’ve just met, and he’s performing to thousands of screaming fans, and then, completely without her knowledge or permission, he announces to the audience that she’s going to come out and sing one of the songs that she wrote. Initially she refuses, so he goes out on stage and sings the first verse by himself, and as he’s singing, we see her backstage wrestling with the decision: should I stand here and stay small, or should I go out there and embrace big?

This is a movie, so of course she joins him on stage just in time to sing her part. If she didn’t step out on stage, there would be no movie, because there would be no story. Why? Because there would be no decision to do the heroic thing, and every story has that decision, the decision to do the thing that most other people would find too big and too scary to actually do. They might wish for it. They might talk about doing it. But when push comes to shove, they won’t actually step out from the old and into the new.

In screenplay parlance, we call the moment of this decision “the point of no return.” It’s the moment when the hero crosses a threshold and steps into a new world, into what we view as a bigger role, and it’s an essential part of the hero’s journey in every story, in every movie. The point of no return in the movie The Blind Side, for example, is when Michael Oher crosses beneath the gates of Wingate School where he embarks on the education that sets him up for his NFL career. In the Godfather, the threshold is when Michael Corleone, who previously sat on the sidelines and didn’t participate in the “family business,” kills a rival who put out a hit on his father, and the police chief who was protecting that rival. In Legally Blonde, it’s when Elle Woods drives across the bridge to arrive at Harvard Law School.

If you look, you’ll see this “crossing of a threshold” in every movie, and I think it’s a good idea to look for this in fiction, because I think that watching it on the screen helps us get comfortable with doing it in real life.

How does it help? I think it helps because we notice a few things about what’s really going on in these scenes. We can glean things from them that can help us in real life.

So now let’s look at exactly why the heroic thing feels heroic and how you can put these moments to work in your own life.

Consider the scene when Ally, Lady Gaga’s character in A Star is Born, steps out on stage to sing the song she wrote with Jackson Maine. It feels like a big moment. It feels like a heroic triumph over fear that few of us would dare to .do.  It feels huge. But exactly what is so big about it?

It’s not the action that she takes. When you watch it, you see her walking up to the mic. Singing words that she knows she can sing. She wrote the words, for Pete’s sake. She’s doing something that she can do in her sleep. On so many levels, what she’s doing on stage in that scene, after crossing the big scary threshold, is no different than what she was doing in the drag bar. It’s a performance that she’s totally capable of delivering. So it’s not the actions. That’s not the heroic part.

It’s not the circumstances either. It’s no longer a performance in the small bar that’s occupied by her friends. This is a giant stadium filled with strangers. But what do we know about circumstances? They’re neutral. She feels comfortable in the small bar and scared in the stadium, but others might feel differently. Some might feel mortified to perform in a tiny venue because they think it’s too intimate. For them, a nameless, faceless crowd might feel a lot better. It’s all about the thoughts you think. It’s the meaning that a person attaches to the circumstance that determines if an action will feel too big to take, or if it will feel like something they can totally do. My client who’s struggling this week can talk about her business all day long, if it comes up in casual conversation. But if she sets out to have that conversation, if she deliberately tries to steer that conversation into a discussion about her business, then the discussion means something else entirely. That’s when it feels too big.

So the first thing to notice here is that big and small are mental constructs. Our brains are meaning-making machines, and if something feels too big, if a step feels too huge to take or even contemplate, it’s because of the meaning we’re attaching to it in our minds. Even the step out onto the moon was just one step. It felt huge when Neil Armstrong took it, but that’s because of what we were thinking about it.

So if it’s not the circumstance, and I can promise you, it never is, what is it, exactly, that makes a moment feel heroic? Is it the result? When Ally stepped out on stage and sang the song with Jackson, the crowd went wild. Is this response what made it heroic? No. We see movies all the time where the hero doesn’t get the intended result. A failed hero is someone who is swallowed by overwhelming force, but they are no less a hero when they do something heroic.

So exactly what is the heroic thing? What makes something heroic? It’s the inner shift, my friends. The step feels big because the hero is stepping into a new type of wisdom. If you do your mental work and that enables you to do something you’ve never done before, we just witnessed an act of heroics, because now you’re wise about something other people don’t know. They want to do it, but they don’t know how, and they admire when you do it. We love to see these acts of heroism. Why? Because that inner shift that allows the hero to do what previously felt too big, too scary, is what moves us forward as a species. Human growth on a micro level, person by person, is how we get big improvements for the human race on a macro level.

So now let’s talk about 3 tools that can help you achieve these heroic inner shifts, so you can start doing things that few others would dare to do, but that everyone wants to do.

The first tool is deconstructing the circumstance. When something feels too big, it’s because you’ve built it up in your mind. If you want it to feel smaller, more manageable, tear it down to its essential activities. If you’re Ally on stage with Jackson Maine, all you’re doing is approaching a microphone and singing a song. You’ve done it a million times. If you’re my client who’s seeking places to deliver your keynote presentation, all you’re doing is speaking words about your business to someone who is hearing those words and speaking words back. Viewed in this way, it’s very much like ordering takeout from an unfamiliar restaurant. You might have a strange interaction, but if you do, all you have to do is call someone else.

This is what you do when something feels too big. Make it smaller, by removing the meaning you’re attaching to it and just focusing on the essential actions of it.

The second tool I have for you today is to redefine the risk. I wish that in film we didn’t call these big moments, or rather, these moments that “feel” big, the point of no return, because that makes them seem risky when often they are not. Occasionally you’ll see a movie where to take the beach, the army decides to burn their boats. In those situations, there really is no going back, and that’s a true risk.

But mostly, there’s no real risk in the moments we perceive as fraught with peril, because even though the moment feels scary, you can always go back. You’re not jumping off a building where things can permanently change for you. In most or almost all cases, nothing permanently changes when we try for the thing that feels big, because the boat-burning situations are rare. We can always go back. Even if we can’t go back to the identical place we were in before, we can always find a similar replacement that’s basically the same. There’s always another crappy job. Another substandard relationship. Another opportunity to do the thing that isn’t really our dream.

So why do these moments feel so risky? It’s only because we fear the feelings that can come up. When Ally steps out onto that stage, it feels risky. I was sitting next to my friend Payge in the theater last night, the second time I saw A Star is Born in as many days, and she put her hand to her mouth and said, “Oh,” as in “Oh my word is she really going to do it?”

Here, what I’d like to offer is that if the worst thing that can happen is a feeling, you haven’t encountered a risk. All you have encountered is an opportunity to manage your mind. We’ve talked about this before, but it’s worth going over again. If Ally sings or if my client asks to make a presentation, and either of them are rejected, all that means is that someone said no. We can make that mean everything, or we can make it mean nothing.

The truth is that we hear no all the time. We can ask in a restaurant, “Do you have cherry pie?” Answer: no. It’s no big deal because we don’t make it mean anything. We can ask a friend, “Do you want to go see A Star is Born with me for the third time this week?” If the answer: “No.” I can make that mean that my friend is busy, or I can make it meant that they think I’m nuts. The meaning I attach to it, the thoughts I think about, determines if I will experience the rejection as painful or as something else.

And similarly, if we’re trying for something in our business, if we’re Ally stepping out on stage or if we’re my client asking for an opportunity to deliver her keynote, we can make a no mean something negative about us, or we can make it mean that they just don’t need the thing that we’re offering, or that we need to sharpen or improve the message.

So that’s the second tool for this week. Remove the risk from a step that you’re contemplating taking, remove the risk that isn’t really there, and it will feel smaller and easier to take.

The last tool I have is how to answer the question, who do you think you are? At one point in A Star is Born, Ally is lying in a dry bathtub, fully clothed and all made up to go out onto a stage for another performance, and she says to her friend, “Who do I think I am?”

This is such a common question, and as you move forward with your big goals you’re going to encounter it.

When you’re about to step into something that feels scary-big and you’re confronted with this question, answer it. I don’t care who’s asking. It can be your mother, God, the universe, or a voice inside your own head. When you hear the question, “who do you think you are?” Just answer. Sometimes when I sit down to record the podcast, I hear this question, “Who do you think you are?” And for a second I feel pretty terrible, and then I just answer the question. The answer I give is, “I’m the person who’s recording the podcast.” And then I feel better. It seems silly, but it really works.

So I hope you try these things. When something feels too big, too risky, too scary to do or even to contemplate, deconstruct it. Remove the risk. And decide that you’re the person who does these things.

This is the way you become a rock star in your own life, my friends. I promise, it will help if you give it a go. I want to thank you for joining me today. It’s been fun having you here, and I look forward to talking with you next time.

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