DON'T BE AFRAID OF LOOKING DUMB WHEN ASKING QUESTIONS! w/ Sean Whalen | Cigars and Coffee

A short conversational YouTube interview (Mark Evans DM with guest Sean Whalen) arguing that people should not fear looking "dumb" when asking questions. Key points: schooling discourages collaborative questioning; entrepreneurs frequently experience insecurity but should ask questions to accelerate learning; fear of judgment—not failure—is the main barrier; asking questions to act on answers (vs performative questioning) differentiates productive people; anecdotes include a paid mastermind where many couldn't solve a Stripe integration and Sean's gym/health experiences used to illustrate judgment dynamics.
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Dude, I don't think people. I don't think people are trained to ask questions. In high school, I remember if I was asked a question, it's called cheating, because I'm asking the person beside me what the answer is. You know, like, it's like, there's no collaboration. There's no thought processing. There's no, like, hey, you're better at math than I am. I'm better at English than you are. We should probably come together and work together and be bigger together. Instead, they're like, no, this is your lane. Stay in it. Don't talk, don't look, just go. And it's like, well, where's the opportunity for collaboration here? And what I'm seeing, too, Sean, is like, a lot of people, insecurities have risen to the top at the highest level right now. People are constrained. They're freaking out. They don't know what else to do except to attack. Their insecurities are like, I mean, it's getting really bad. It's, like, going to take over. And I think as business owners, and it's not that business owners are better than anybody, but we have real insecure conversations with ourselves all the time. You know, you've worked with a lot of business guys, and again, I don't care if they're making a lot of money or low money, you're still insecure. You're still having these anxiety attacks. You're like, oh, my God, this is the one that's taking me down. Your heart's beating 100 miles per hour. You know, so I think we do have a little bit more. What just comes down to awareness, right? Like, why am I feeling this way? What did I do? Like, again, questions, you know, being.
Being aware. But I also think, and this is something that I know that you'll echo, and any entrepreneur that's listening, you're okay to fuck up because you've done it before. Like, this is a lot of people. Like, oh, I'm afraid to fail. No one's afraid to fail. Here's why. How many of you listening to this have failed before everybody? How many of you are like, me? And you failed a ton of times. Like, you double fist this one, right?
Yeah.
Like, people aren't afraid to fail. What we're afraid of is being judged. And so it goes back to that reality. Like, you. And I realized, like, I was in a mastermind last year, paid 25k for it. Digital mastermind. Whole bunch of really smart digital people, whole thing. I couldn't figure this one thing out. I couldn't sum it. I couldn't get my. My. My Stripe account to connect to this portal that we had put up. And I was, like, racking my brain. I couldn't get it figured out. And here I was part of this group with all these smart. And I felt. I was like, D. I didn't want to ask. I was like, oh, shit, I'm gonna be D. Supposed to be simple, right? And I was googling. I couldn't find it. I go into the group and I finally asked the question, and people are like, oh, I've tried to do that too. I don't know. There were like 50 people that didn't know either. So I'm not the only one. You and I are not afraid to ask dumb questions.
Yeah.
And that's the difference, Right. Real difference is people stop and they're like, I'll just keep trying and trying and trying and trying. And the definition of insanity is banging your head against the wall.
That's right. Different result.
I'm not afraid to look dumb, if you will. You're not afraid to look dumb. So as an entrepreneur, I think what we have found is, like, if we want this result, we're going to ask the question. If I'm at the gym and I'm telling my trainer, this is this or this is that, you know, and he gives me a solution, I'm going to get a different place. And the guy who's like, I'm not going to say anything because I'm going to look dumb. So you have to understand, like, when you're an entrepreneur and you're a business owner, the.
The.
The time frame that you spend not asking questions, not getting the answers that you need, it's insanity. It's what's keeping you back from being successful, from having. Having that, from having whatever you've got. I mean, you and I are way more prone to look dumb to get the answer that we want. Yeah.
I mean, and not only that, define what dumb looks like. Right. I think. Here's the truth is, guys, we're getting judged no matter what. You know, if you're failing, what does failing mean? If you're. Here's a. Here's what's interesting about. You're going to get judged. If you're failing, which doesn't serve you, and you're going to get judged. When you're rich and you're winning, that serves you. You're getting judged no matter what. It's just we put different weight on each one. Is it a negative weight or Positive weight. The truth is, most people hate us just because we live in America. Most people hate us because we're white. Most people hate us because we have a beard. Like, who knows why they hate us? It's not. That's them judging us, not me judging them. Like, I don't have that judgment thing in my head. The only thing I do judge is people that ask questions. Sean, that don't do anything with the answ, that's an asshole, right? They're just asking questions to sound cool and be in front of people. You know the difference? As you're growing and developing, like, some people just want to ask questions to be heard without doing anything to do it, to take the action behind it. So when Sean and I are asking questions or people like you and I, we're asking quite. We genuinely want to know the answer so we can actually go execute and get a result. And I think that's the vast difference.
Totally agree. You know, and what you just said is dead on. Is something that I talk about all the time. No matter where you go, no matter what you do, you're going to be judged. People are terrified of being judged. You're not afraid of failing. Most people listening to this have lost money before, right? So you're not really afraid of losing money because you've already done it, right? Most people have struggled with some sort of being down or depression in some way, shape or form. You're not afraid that you're afraid of being judged by. For talking about it. But people don't realize is exactly what you just said. If you're fat, it's because you're a lazy piece of.
Right?
If you're ripped because you're on steroids, he's got. You got to be taking steroids, right? If you're poor, you're lazy, you're undisciplined, and if you're rich, you're selling snake oil, you're totally ripping people off. It's like, no matter where you go on this spectrum of life, no matter where you're playing the game, somebody's gonna judge you, period. They're gonna judge you. Oh, he's ripped. You know how many times last year I had spine surgery? You know this. I got ripped. I did 75 hard. I took the challenge of my body, and for the first time in my life, I have a six pack ever. He's taking steroids. He's preferred taking serious. Every time I post a picture, steroids, territories. And I'm like, I figured out an answer for this. You Wanna hear my answer next time? Like, yo, you're ripped. It's because of steroids. If that was the case, if that was true, if steroids got you ripped, why are you still fat, bro? I asked this guy this question, like, if all it takes is sticking a needle in my ass to get my six pack, then why are you still fat? Yeah, every man in America would take that shot.
That's all it took.
So is it possible it's not just steroids? You start throwing logic back at him, like, man, yeah, not that true.
Right?
But people are terrified of being judged. Yeah, we judged no matter what. You roll up in a Bentley, you roll up in a Ferrari, you roll up in a Ford pickup truck, people are gonna judge the out of you.
Yep. Period.
Once you pass that and realize that and really wrap your head around that, because I was stuck in that after I lost millions of dollars when the market crashed and the whole deal, I was terrified because I was getting, you know, being judged in the whole thing. Then I realized, like, matter what I do, everybody, people are going to judge me anyways, so I might as well do the I want to do. Voila. Somehow I found happiness that way versus, like, trying to live this life where I'm living it based off of all these other people's rules and judgments, What I know and how I did it to discover freedom. There ain't no question mark. Kevin's. When he stepped in the doubt, he's closing deal.










