23 Oct 2026 · 13 min
In this solo episode of The $100 MBA Show, host Omar Zenhom tackles the pervasive issue of self‑doubt for entrepreneurs. He frames self‑doubt as an expected, recurring condition that appears whenever a risk is taken—launching a product, hiring, raising capital, or trying a new platform. Omar outlines a four‑step framework: (1) anticipate self‑doubt; (2) build confidence through daily micro‑promises and consistent action; (3) reframe failure as practice by intentionally seeking small losses and learning from them; and (4) act immediately when doubt surfaces, never waiting for perfect readiness. Throughout, he illustrates each point with personal stories (Bill Russell’s pre‑game anxiety, Phil Knight’s 20‑year struggle in "Shoe Dog," his own failed DIY Webinar Guide that led to the successful Webinar Ninja) and concrete habits (morning gym routine, micro‑goals, rapid recovery after a broken promise). He also contrasts a "play‑to‑win" mindset with a "play‑not‑to‑lose" approach, emphasizing tolerance for rejection as a numbers‑game skill. The episode ends with a call to action: subscribe, set small commitments, and keep moving forward despite doubt. Interspersed sponsor reads (LinkedIn, Dell, Square, Mazda) are present but not central to the instructional content.
Chapters
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Your laptop will help keep you locked in even when it's bring your dog to work day. Built for those who stay in the flow. The Dell Pro, built for you. dell.com/dell-pro. You don't become confident, then take action. You take action, then you become confident. Every entrepreneur feels self-doubt and it really never goes away because you keep taking on bigger and bigger challenges in life. If you wanna be confident, you gotta take action daily, but most people don't because they're afraid to fail. If you want success though, you must get good at failing. You need to make it part of the process, not proof that you should quit. Today, I'm gonna teach you how to normalize self-doubt and use it to move forward despite your fear. Let's go. Welcome back to the $100 MBA Show. I'm your host, Omar Zenhom, where I deliver practical business lessons 3 times a week, Monday, Wednesday, and Friday to help you start, grow, and scale your business. I think people forget that anyone that does anything significant is scared. In the business world, self-doubt tends to hit entrepreneurs the hardest when a decision becomes public or real. Many people stay in prep mode or delay launching. They do what I call playing business. It feels like a safe option because you've never actually launched and exposed yourself, but self-doubt reoccurs Every time you hit a new stage in business, hiring for the first time, raising capital, starting a YouTube channel, it's okay to feel nervous. It's okay to be scared. Even high performers experience this. I remember a story by Bill Russell, who is one of the most popular and most winning basketball players of all time. He won 11 championships. Before every game, he still went to the bathroom and threw up out of anxiety. I'm no Bill Russell, but of course I still feel self-doubt before every episode I record. But the truth is, is that every big failure I've had in my life resulted in a huge success. My first podcast failed, which led to this podcast, which succeeded. So how do you handle self-doubt? Let's start with step 1. Self-doubt needs to be expected. Self-doubt is not a problem that you can solve once and you're done. It shows up wherever you take a risk, wherever you enter a new stage in business. Launching, hiring, raising money, trying a new platform, trying a new strategy. You can feel like a beginner all over again at every stage of business. The goal here is not to become fearless. The goal is to recognize self-doubt and choose to move forward anyway. Step 2 is to build confidence. And here's the truth. Confidence is built through action, not something that you either have or you don't. Okay. There's no way around this. You have to take action so that you can start to feel confident. One of the hacks that I highly recommend is to start by keeping small promises to yourself. Okay? So for example, I wake up in the morning. I know that I need to wake up at a certain time so I can get to the gym by 7:00 AM. If I wake up in time to have breakfast and go to the gym and I rock up to the gym at 7:00 AM and I do my workout, I tick that box in my head where it's, I plan something, I say I'm going to do something and I do it. I didn't break the promises to myself. I don't break promises to myself because I know it's a fast way to erode your confidence. But if you want to build your confidence, just create these micro goals and fulfill those goals on a daily basis. Every time you do that, you build a brick of confidence in the wall of confidence in your life. If you want to go on vacation, start saving money, start planning the vacation, start pricing it out. If you want to finish a task, keep yourself accountable and finish it. Every time you follow through, you prove to yourself, I'm someone who does what I say I'm going to do. And every little commitment you keep is another brick in that confidence wall I'm talking about. So don't neglect the small things. The small things actually make you feel the most confident because you're getting so much repetition. You're doing it over and over and over and over. You have a track record. You have a library of evidence that you do what you say. So when doubt hits, you can remind yourself, I do hard things. I accomplish things on a regular basis. The key to this is that you can't control outcomes, but you can control your action, the inputs you put in. So say, for example, you wanna launch a successful podcast. By the way, we just did an episode on this topic. 2 episodes ago, so go check it out. But if you want to launch a successful podcast, you really don't have full control of being the number one podcast in your niche. But you do have control over showing up and recording episode after episode consistently and never missing an episode. This is what I love about this show that I run, The 100 Day MBA Show. We've recorded over 2,800 episodes. In fact, this is episode 2,850. But the reality is I have 2,850 Pieces of evidence that I show up consistently and I put in the work. And as long as I put in the work, the results will eventually show. Support for today's episode comes from Square. You probably know Square as the thing you tap your card on at your favorite coffee shop, restaurant, salon, or local store. But for the person running that business, Square is a whole lot more than a way to get paid. Square brings the tools you need to run and grow your business together in one system. From payments and appointments to staff, inventory, sales, and customer relationships. Whether you're selling lattes, cutting hair, detailing cars, running a restaurant, or starting something new, Square keeps your business tools working together so you can focus less on managing the moving parts and more on what's next. Whether you're starting something new or looking for a better way to run the business you already have, Square gives you the tools to take payments, manage your day-to-day, and keep growing. And right now you can get up to $200 off Square hardware at square.com/go/MBA. That's square.com/go/MBA. Run your business your way with Square. Get started today. When you're at work, you never know when you'll be interrupted. But with the Dell Pro powered by Intel Core Ultra with vPro, no matter what distracts you, Your laptop won't. It's battery optimized for the way you work with built-in intelligence that quiets distractions when you need to focus. Your laptop will help keep you locked in, even when it's bring your dog to work day. Built for those who stay in the flow. The Dell Pro, built for you. dell.com/dell-pro. Step three is to reframe failure as practice. Failure is a rite of passage, not a signal to stop. Here's the thing about losing: when you lose, you reflect. I play basketball for the North Bears, the club I play for, and last Sunday we lost. It was a really close game, but when I lost, it wasn't just like all depression and sadness. The first thing I think about is what went wrong? What can I improve next time? What can our team do? the next time around so that we get that win, not only against that team, but next week as well when we play another team. Sure, success feels good and winning is amazing, but failure is where all the teaching happens. One of my favorite biographies is Shoe Dog by Phil Knight, who is the founder of Nike. And if you read this book, it's basically 20 years of failure, right? The guy's eating glass and failing and on the edge of going out of business For nearly 20 years. And the book kind of ends when he starts winning, meaning when he signs Michael Jordan for the big deal, uh, where he wears Nike shoes on the basketball court. And you don't see anything past that. The whole book is all the stuff that came before that. And the reason why he did this is because you don't really learn anything from the wins, from the successes, from all the things that they do after when business is kind of easy for them. You really learn from the struggles, from the hardships, from how they got out of a jam. Right. And this is why I love that biography so much, cuz it's so real and honest. If you wanna get better at failure, if you're somebody that just like hates losing and you really get angry when this happens and it makes you wanna quit, then here's an exercise I really recommend you do. Intentionally fail. Yeah, I'm serious. Actually try to lose at something. Do something new. Normalize failure. If you've never played pickleball, go play pickleball this weekend. And see how it feels to be a beginner again. If you've never ice skated before, go ice skating. 2 years ago, somebody introduced the game of poker to me. I was horrible at it. I was really bad. But when you start something new, you can't expect to be good at it. You're going to stink, but it's okay. You're going to learn a ton and you're going to just be okay with the fact that you're not so good at it. And I recommend doing this over and over. Like once you get good at it, like now I'm pretty good at poker and I'm winning a few tournaments. But now I got to choose something new to try so I can fail and learn and be comfortable with losing. Here's a secret about successful entrepreneurs. They're successful because they can tolerate more rejection than anyone else. That's really it. They're just willing to lose enough to learn and win. For example, before I created and launched my webinar software, Webinar Ninja, we had a product called the DIY Webinar Guide that totally flopped, that failed. That was a big waste of time and money and energy. We spent 4 months building this product. That got 2 sales, which one of them was a chargeback, which is fraud. The second one was like a sympathy sale from a friend. But that failure did something incredible. It reminded me of a quote from a book called The Hard Thing About Hard Things by Ben Horowitz. And he says, sometimes you got to create a bad product to create a great one. That failure taught me no one wants to learn how to do webinars. They want a tool that helps them do it for them. And that's where Webinar Ninja was born as a webinar software. We launched it, we built it over 10 years, we grew it over 30,000 users. And then we got acquired. That would never happen if I didn't fall on my face, fail, and learn from that failure. Been open to learning from that failure so that I can launch the next thing more effectively and more successfully. Step 4, you got to take action. The cure to self-doubt is action. As soon as you start feeling doubt, just take any small action forward. Never wait until you feel ready because you'll never feel completely ready. Confidence comes after you take action. Whatever the next step is, take that next move. Publish, launch, pitch, ask, apply, make a phone call, whatever it takes. Take that next micro step so that you are not in your head and you're in the world doing it. We got a lot more to cover to get you through, so you make sure that you are in control of your self-confidence and you keep self-doubt at bay. But before that, I want you to subscribe to the show. Why? Because we have an upcoming episode I don't want you to miss. It's titled Treat Your Business Like a Game and Get Rich. I really believe that business is like a video game. It has levels and different bosses that you have to fight, and it teaches you that not only is winning important, but how you win and the journey you go on is really what it's all about. I'm going to show you exactly how you actually relieve yourself of the pressure of being successful by having fun in the process. Hit subscribe so you don't miss that episode. One of the things I learned by playing competitive sports is that in order for you to consistently win, you need to play to win and not play not to lose. There's a big difference. When you're playing to win, you're not afraid to lose. You're just going all out and whatever happens happens. It's— you're okay with it. But when you're playing not to lose, you play tentative. You try not to make mistakes. You're thinking about how you're being perceived by other people that are watching. You're letting your fear of embarrassment and failure control you rather than your desire to win. Always play to win. Don't play to avoid losing. Okay? You can't build confidence that way. You build confidence by giving 100% and not worrying about the result. If you fail, learn from it. If you don't fail, great. Move on to the next level. But you can't build confidence by staying on the sidelines. It just doesn't happen. The more you act, the more familiar you are with fear. And that feeling of self-doubt, the more you're going to have power, the more you're going to be able to recognize it and say, I know this old friend, I'm used to this. I'm going to move forward despite it. Listen, self-doubt is normal. Confidence comes from keeping the promises to yourself, especially the small ones. Don't neglect this. Most people feel down on themselves because they have a history of breaking promises to themselves and to others. It's time for you to start living your promised life, right? The life that you always wanted. And the only way to do that is to keep your promises. And if for any reason you break a promise, you don't stay consistent, you don't do what you're supposed to do, you gotta immediately get back on the horse. You can't just dwell on it. You can't just say, oh, I'm not consistent. Maybe I'm not cut out for this. No, immediately get back to it. If you didn't do it, do it now. Do whatever you're supposed to do. Like if I missed the gym this morning, go in the afternoon. Doesn't mean it's over for today. You can make up for it by just getting back on track as soon as possible. If you want to be a successful entrepreneur, the key is really just to be comfortable with rejection at scale, because in business, it's a numbers game. You just have to endure a certain number of nos to get a yes. And as long as you're able to endure those failures, you'll be ready for the success when it appears. Self-doubt never disappears, by the way. So the question is whether you're gonna let it stop you or not. It's gonna be there. So recognize it. Say, hey, I know it's gonna come. I'm expecting it. I'm gonna move forward despite it. All right, that's enough listening to me. It's time for you to take action. Start making some commitments to yourself, some goals, and fulfill those commitments on a consistent basis. If you wanna see an example of somebody who moves forward despite their doubts and is just comfortable being themselves, Go and check out my conversation with Taki Moore. He shows you how to build your own lifestyle empire using your own personal advantage. It was recently published on the podcast, so just scroll up on whatever app you're using right now. If you found today's episode helpful and you want more practical business lessons to help start, grow, and scale your business, subscribe to the podcast. All you got to do is hit subscribe or follow on your favorite podcast app, the one that you're using right now. By hitting subscribe, you get our next episode automatically. It's absolutely free, and it's a way for you to commit to growing your business. I'll check you in the next episode.
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