The #1 Skill to Develop is the Ability to Not Judge Yourself

Summary

Podcast Summary: The GaryVee Audio Experience Episode: The #1 Skill to Develop is the Ability to Not Judge Yourself Date: July 16, 2026 Host: Gary Vaynerchuk

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Episode Overview

In this candid and high-energy episode, Gary Vaynerchuk explores the single most important skill for entrepreneurs and business leaders: the ability to not judge yourself. Gary dives into the practical impact of self-judgment on business decisions, moving fast versus overanalyzing, and how liberating it is to operate without second-guessing. Using anecdotes, real-world examples, and trademark GaryVee analogies, he demonstrates how this mindset fuels his success, decision-making, and company culture.

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Key Discussion Points & Insights

1. How Gary Spends His Time (00:05 – 03:05)

• Gary asserts that his ability to avoid self-judgment is foundational to how he manages time and makes critical decisions.
• He rejects rigid scheduling: “I’m extremely thoughtful about cutting times in meetings. A seven minute meeting is real and not just making it a 30 minute meeting.” (00:48)
• Major decisions are made with the information available at the time—there’s no perfect call, and you’ll never know the true alternative outcome.
• He balances focusing on what’s working ("offense") and shoring up vulnerabilities ("defense"), avoiding the trap of splitting time on “the middle.”
• “The second I get new data a week later, I might have to completely change what I thought was right the week before.” (01:57)

2. Avoiding Paralysis & Embracing Speed (03:05 – 06:00)

• Gary does frequent, iterative audits of his calendar but doesn't dwell on possibly “wasting” time—speed is more important than perfection.
• “I easily spend 25% of my day on things that end up being dumb shit. That is where the speed comes in.” (03:37)
• Judging oneself over past decisions is a productivity killer; Gary stresses learning as you go is more efficient than excessive reflection or pontification.
• He prefers present-focused, action-oriented learning to retrospective analysis: “Just the doing is actually more efficient than the thinking about it.” (04:30)
• Humorous anecdote: a critique comparing VaynerMedia’s action bias to “running through a glass panel” instead of opening the door—he celebrates the bias for action: “Yeah, but which one was cooler?” (05:02)

3. Why Self-Judgment is a Trap (06:00 – 09:24)

• Gary highlights how crippling self-judgment prevents momentum and drains “mind time.”
• Developing a habit of not beating yourself up over mistakes compounds into real confidence and the freedom to experiment.
• “You don't beat yourself up over a mistake. No, because everyone else is doing it for me.” (08:36)
• He draws parallels between business and sports: it’s about how quickly you move on to the next play after a mistake rather than dwelling on it.

4. The Power of Speed and Decisive Action (09:24 – 11:04)

• “Speed becomes your ally when you’re able to move, bro.” (09:28)
• In both business and sports, speed is often the ultimate differentiator: “There’s a reason the Chiefs are good right now. Draft speed. It’s not teachable.” (09:38)
• Most of his decisions are snap calls based on the day’s data—not endless “homework.”
• He challenges over-valuation of process: “You know how many more decisions you can make when you’re not in the process of one?” (10:52)
• Mistakes are part of the ratio—success comes from making more decisions, not just avoiding errors.

5. Entrepreneurship vs. Operator Mindset (12:05 – 13:22)

• Entrepreneurship is a distinct talent, embracing risk and intuition; being an operator is more teachable and focused on execution.
• “There’s a very big difference between being an entrepreneur and being an operator ... the entrepreneurial part is where the real hyper upside actually lives.” (12:17)
• Gary likens his approach to the Kansas City Chiefs’ offense, favoring high-velocity innovation over defensiveness.

6. Building Businesses under VaynerX & Learning from Losses (13:22 – 15:10)

• The VaynerX umbrella is structured for communication speed and adaptability; expansion decisions are driven by gaps Gary sees and people he wants to support.
• Gary is open about failed ventures (Vayner Experience, Vayner Live) and sees them as learning steps, not reasons for self-critique.
• “I love losing as much as I love [success] because I know the fifth time I'm gonna get it.” (14:24)
• When he makes a call that doesn’t work, he openly acknowledges it to his team—integrity in leadership.

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Notable Quotes & Memorable Moments

• On Decision-Making:
  • “You will never even come close to making the right decision. I mean it. You just don’t know what the alternative would be.” (01:23)
• On Avoiding Self-Judgment:
  • “It starts with the ability not to overjudge yourself, because that is the liberator of the model I just broke down for you.” (02:45)
• On Speed Over Perfection:
  • “If you’re not spending half your time judging yourself if you’re getting it right ... just even in the mind. There’s no way I do this. That’s not how I learn.” (04:12)
  • “You know how many more decisions you can make when you’re not in the process of one.” (10:52)
• On Mistakes:
  • “As long as I don’t put us out of business, I’m like, yeah, I hate that I made that call, you know, I prefer not to. I wish it didn’t happen, but it did. And spending ... I’ve learned from it. I don’t need to, like, beat myself up to learn from it.” (08:51)
• On Entrepreneurship:
  • “Entrepreneurship is crazy hard and talent oriented. It is truly a skill.” (12:09)
  • “The entrepreneurial part is where the real hyper upside actually lives. The operating part is commoditized.” (12:19)
• On Losses:
  • “I love losing as much as I love [success] ... because I know the fifth time I’m gonna get it.” (14:24)

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Timestamps for Major Segments

• 00:05 — How Gary allocates time and avoids self-judgment
• 03:05 — Auditing the calendar, embracing fast action, learning by doing
• 06:00 — Why self-judgment kills entrepreneurial performance
• 09:24 — The irreplaceable value of speed in business and sports
• 12:05 — Distinguishing entrepreneurs from operators
• 13:22 — The logic behind VaynerX’s structure and embracing failed attempts

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Tone & Delivery

Gary Vaynerchuk’s tone is direct, passionate, and relatable, loaded with actionable insights and colorful storytelling. He combines humor, honesty, and intensity, creating a “tough-love” mentoring session that challenges listeners to act, fail fast, and stop spending time overthinking past decisions.

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Takeaways

• The primary skill for business success is NOT judging yourself—momentum matters more than perfection.
• Embrace rapid action and iterative improvement; speed trumps process.
• Mistakes are learning tools—not emotional liabilities.
• Structure your business and time for adaptability, communication, and continual offense.
• Own your calls—right or wrong—and keep building without looking back.

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For anyone looking to move faster in business or life, Gary’s message is clear—stop judging yourself and start doing. That’s the cheat code.

Transcript

[A]

This is the GaryVee audio experience.

[B]

How do you make determinations on where and how you spend your time, knowing how valuable and how limited your time is?

[A]

I'm really happy you're asking this question because if you can internalize what I'm about to say, you will not believe what it's about to do for you. The answer is the ability not to judge myself by, you know, how a lot of times there's a lot of people in. There's a really dirty secret in the strategy world of like Bain and McKenzie where if you really get them drunk, they admit that the actions lead to the strategy, not the other way around. That's my answer to you, how I make decisions. And then I try to look at my calendar the week ahead and see if any decisions I made four weeks earlier that made me think this was a good use of time. Am I able to move something, cut something down? I. I'm extremely thoughtful about cutting times in meetings. So one of the things I think that really make me successful is understanding a seven minute meeting is real and not just making it a 30 minute meeting, but the real reason is cause I don't overthink it. I'm operating my business, I'm in it. How do I decide between going to dinner with Kevin Hart because I can and I want to build top of the funnel brand, or do I go take a mid level client that I'm trying to build a relationship with? It's, you know, you ask every normal person, it seems like those aren't super close, but I can touch the pulse and be like, I'm going to LA four more times in the next three months. You know, the biggest mistakes I make are the ones of missed opportunities, of the things by being crippled by opportunity. When you actually level that all up, my friend, it really is liberating. You will never even come close to making the right decision. I mean it. You just don't know what the alternative would be. People think that there's a right answer. You as an operator of your business make the right call that feels right at that moment and just move. And people spend all this time and money on trying to think that there's a proper answer. I play on the extremes. I spend as much time as possible on the things that are showing me the most offense. Right. However you're doing your customer acquisition to get to a hundo on a product like that, like whether it's Facebook, whether it's brand, and then I spend the amount of time on my biggest vulnerability, you know, putting My finger in the holes to make sure the boat doesn't sink. And building a bigger fucking boat and nothing in the middle. And knowing that I'm making that judgment at all times. And the second I get new data a week later, I might have to completely change what I thought was right the week before. It's also why I spend a ton of time with my employees. The reason I'm an HR driven CEO is if you really understand this, both your biggest growth and your biggest vulnerabilities are actually your own team. So I think it's a lack of. It starts with the ability not to overjudge yourself, because that is the liberator of the model I just broke down for you.

[B]

But even the items that you may have scheduled out four weeks in advance, you still sit down at the beginning of that week to reevaluate at our best.

[A]

Which I don't do all the time. My admins and I are doing some sort of version of an audit on Friday. Mm.

[B]

Because. Yeah. You find yourself in that paralysis of where are you spending your time on the most valuable activities.

[A]

I don't think that way. And nobody. I mean, listen, I'm in the mix for top busy people. I'm in the conversation. You know, I go hard for 15 hours a day. I do seven minute meetings. I'm fucking in the conversation. And I easily spend 25% of my day on things that end up being dumb shit. That is where the speed comes in. Got it. If I spent time looking back at my calendar for the last month, I'd be devastatingly sad. People judge themselves. If you're an operator and you're in the mix on your business, you made the best decision you could at that moment with the data that you had. The end, was it to go to a Kroger's meeting or was it to go meet a supplier of milk? Or to go meet an influencer who was destined to be the one that broke you out. All three sounds bright to me. And they all could end up being right or could end up being wrong. My thing is, if you go super fast and go super hard and super efficient, you might be able to do all three. If you're not spending half your time judging yourself if you're getting it right. Got it. You see where I'm going? You wouldn't be here. Maybe that's what you needed today. Like you would have this whole day back. Just even in the mind. There's no way I do this. That's not how I learn. Now you may learn this way. But there's never a chance in hell that I'd ever be at a 4Ds because I learned from so much doing. That's why my data is so clean. That's why I'm an innovator. It's why I'm fast. It's why a lot of good things happen for me. Because I realized just the doing is actually more efficient than the thinking about it. Somebody said something really funny to me once, and it was like the dig of this version, and it's a really funny conversation. He was talking about VaynerMedia at the time. This was maybe five or six years ago. He said, you know, Gary, I gotta tell you, I love your company, but I gotta take a little bit of a knock on you. He was trying to set it up. I'm like, okay, what is it? He goes, if I was sitting in this room and you guys were standing outside and I said, vaynermedia, I need you to sit right next to me. I know you guys would do it. He goes, where? I think you need to be more thoughtful. Gary is. I have a feeling, though, that you might run through that glass panel and sit with us when you could have just opened the fucking door. And I said, yeah, but which one was cooler? You know? And so the answer to that is like, I think what, you know, what that gentleman didn't understand in his analogy as a critique was he was trying to have an intellectual conversation about something that all of our businesses will be super fun to talk about in a Harvard business study or around a campfire and 40 years with our grandkids when we can pontificate. But we're operating right now. That got will work. Hey, everybody. Hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy. You can't imagine how much mind time is actually being wasted if you're thinking about that question. It's crippling. I mean, it. I have a lot of empathy for it. And I'm really like. That's why, you know, I don't normally pause before my answer. I was super pumped you asked that because it's one of the biggest answers I've gotten in my repertoire. And if I can, you know. Cause I'm a good communicator. If this is the moment and you get momentum on this, you will fucking. You'll be back in a year and be like, it was just that I didn't realize how much that was affecting me. And that makes you then faster. Then all of a sudden you can see where this goes, right? All of a sudden because you know you're doing this thing that's foreign to you. Fuck it. Gary said, let me try this week. All of a sudden you're like, fuck. But I want to get this up. And all of a sudden that 30 minute meeting becomes 16. All of a sudden that meeting, you just cancel and you do it the next day, you turn it into a call on the way. I'm the manifestation at this point of being in my prime of something I've now done for 22 years. Tomorrow I turn 44. So I'm right there. 22 years of not running a business and 22 years of now running businesses completely always. And now I'm in, you know, in this state where like, oof. I feel really, you know, unstoppable because it's like you're just at the extreme version of. It's like working out every day for 20. You're in a different place. I'm in a real crescendo of like this model. And it really works. You don't beat yourself up over a mistake. No, because everyone else is doing it for me. You know what I mean? We just can't. I really do think business is much more like sport, you know, it's really funny, I used to always think that it always made sense that I like both. Now I hear things back to being in the prime. You hear things of like a quarterback saying, you know, I just gotta go to the next play. I know I threw two picks in a row. And he's right, you know, I used to hear it as a fan. I'm like, fuck you, you fucking threw two picks. I'm pissed. You know, like I thought about now I'm like, that's exactly right. Like I can make seven bad decisions as long as I don't put us out of business. No, really, I really, it's that binary. It's a funny thing to say, but to your point and to like mine, as long as I don't put us out of business, I'm like, yeah, I hate that I made that call, you know, I prefer not to. I wish it didn't happen, but it did. And spending. I've learned from it. I don't need to like beat myself up to learn from it. I learned from it. I understand that I over when I over leveraged our ice cream business to too much retail and gave them too much leverage. And now when they kicked me out, I'm in trouble and I should have built my direct to consumer business. Right? It's not super complicated.

[B]

Yeah. And speed becomes your ally when you're able to move, bro.

[A]

And you'll love this one thing that business and fucking sports share that nobody talks about speed over everything. There's a reason the Chiefs are good right now. They figured it out. Draft speed. It's not teachable.

[B]

To your point though. You find often you're in situations where you have to make. You have to make snap decisions. I can choose to do this or I can choose to. And you're only basing it on the available data.

[A]

Correct. I don't even need to do any homework. That's why I'm always improv. I'm fucking operating my business. I can make a decision right now. It's the lack of judgment, right? See how that's kind of frothy? But you're like, oh right. That makes sense. Cause if you choose and then it was super obvious six months later that you should have went triple retail instead of doing diet milk making up shit now. Well, okay, but I didn't. But like what? I don't. I don't think. I think people think they're gonna do some they value process when you're dealing with the actual consumer. They're moving as fast as you are faster. Not with me. That's why I'm win. Right? Like I feel like I'm with them. I'm day trading. My decisions are in day trade mode. And people think that they overvalue what they were taught in school. The process. You know how many more decisions you can make when you're not in the process of one. And then what ends up happening is you net win because that mistake you made was offset by four other good decisions you made.

[C]

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[D]

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[A]

It's so cool to, like, even, like. Like I'm listening to myself almost right now, and I'm like, God, it makes so much fucking sense. But it speaks to why entrepreneurship is crazy hard and talent oriented. It is truly a skill. Like, there's a very big difference between being an entrepreneur and being an operator. And some entrepreneurs can be operators and they tend to do well. And some people can be operators and they build very nice businesses. But getting good at those two things, and the entrepreneurial part is where the real hyper upside actually lives. The operating part is commoditized. It's a more teachable skill than leaning into intuition, leaning into listening to the end consumer, leaning into, you know, nuances of innovation. Enjoying risk, not being fearful. I think that what I just talked about is being the Chiefs, and I think most people are trying to build the 85 bears. People are defense oriented, which is great. Both. Both can be good, right? In the way that I just said it. But, like, there are way more teams that have won because they were the best offense. Defense wins championships is a very, very misleading, very misleading statement.

[B]

Hall of Fame defensive linemen or linebackers that disrupt the offense. Sure,

[A]

go ahead. We have enough time to balance. If you got something on the tip of your tongue, please feel free.

[B]

One of the things I'm really impressed by is, is the Vaynerx umbrella, right? You've got different distinct businesses. We met today, different folks across those. Gary, what's driving that structure as opposed to. Oh, okay.

[A]

It's the speed you can move that, you know, I'm tired of paying a big commission on my speaking fee. The kid who's been doing it for nine years is becoming a grownup. I really genuinely like him. I'm building one massive communications framework. Part of communications is humans that communicate. We should start a speaking bureau. That's the success. I don't talk about Vayner Experience and Vayner Live. I've had two failed attempts now at doing event marketing.

[B]

He was in the hallways today.

[A]

I know. I was with him. I love losing as much as I love the Sasha group is as much as I love Vayner Live and Vayner Experience. Because I know the fifth time I'm gonna get it. Because live events matter in today's world. Definitely matters in your world. It's a place to think about. So, like, you know. So do you move fast when you decide if something's not working? Yes, but where my team thinks I move slow is it might not manifest as quickly as they thought. It's because I haven't decided that's not working. I'm okay being down 31 nothing at halftime if I truly believe I'm gonna win. 35. 31. As you can imagine, if you've got executives, consumers, business partners, they're like, you're down 31 nothing. You know, And I'm like, mm. But I was at the Monday night miracle. We were down 30 to 7 with 10 minutes left. We won. It sure was. I wish social media existed so I can prove I was there. Cause every Jeff Fam claims they were there, but there was only fucking 4,4000 people there. So, you know, I think that. I do. I do. But that is singular decision by me, not my experts rallying around. But when my experts rally around and I hold the line and the final comes in 48 to 17, I look at them and say, I was wrong. So if you're gonna do it to keep credibility with your teammates, you have to acknowledge when you're wrong. So, yes, I do. And sometimes that goes the other way, you know, sometimes, I mean, there's a story I reference a lot of hiring somebody and literally knowing within 24 hours of them being in a building that I fucked up big. Everybody, if you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention, and thanks for being part of this journey. See you later.