MBA1905 Q&A Wednesday: How do I not second guess myself and make a decision?
2 Feb 2026 · 15 min
Farida asks Omar how to stop second-guessing herself as a new entrepreneur. Omar says decision-making is a skill that improves with practice, like surfing or basketball. He recommends setting timelines, listing pros and cons, imagining worst-case outcomes, and reviewing decisions afterward to build the muscle.
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Farida, who asked today's Q and A Wednesday's question is new to entrepreneurship, but even if you're not new to entrepreneurship, you might be going through the same thing. You're second guessing your decisions, whether it's during the decision making process or even after. When I started entrepreneurship back in 2001, I was side hustling building businesses on the side while I was teaching and that was my career. I was a teacher. I was a full time teacher in the classroom. But I might as well, have been a professional surfer. What do I mean by that? Like, I don't know how to surf at all. So my muscles, my skills, my balance, all those things are very weak for the sport of surfing. If I try to get on a surfboard today, I probably wouldn't be even able to get on my knees. I don't know how to do it. I haven't tried it. Even if I was shown, it would take me some time to build the muscles to be able to get on the board on my knees and then slowly stand up while the waves are going on and get my balance. I just don't have the skills yet. Right. I'm just so new to this. And this is exactly what's happening with entrepreneurship. What I realized is that when I was side hustling building businesses on the side when I was teaching, my decision making muscles as an entrepreneur are completely weak. Like I can't use them because I haven't used them. Imagine tying your arm to the side of your body for a day to a week, years. Your arm would have to be amputated because you're not using it right. Your arm would be very weak after even just one day. So the point I'm making is, is that a lot of us forget that there are different skills that we are not used to deploying or using in entrepreneurship that we don't use day to day in our normal life. And one of those is decision making. Decision making is something that you have to remember, is a skill that you have to build. It's a muscle you have to grow. I mean, if I look at my life as a teacher versus entrepreneurship, I was told what to do every step of the way. Every minute of the day is prescribed for me. So I know exactly what I'm doing. Right. They tell me exactly when to show up to work, when's first period, when I have to show up to the class, which classroom I have to go to, the curriculum is laid out. I know exactly what I have to teach that day. I know exactly what the exam is like. I know who the students are and their names and everything. They're giving me a desk, they're giving me a smart board, they're giving me a laptop. Like the whole thing is set up for me and I don't have to make any decisions along the way. I just have to go and implement. I'm employed to do that. Just go and teach. That's all I had to do. I didn't realize how little decisions I made every day at work until I Started building businesses. Right. Started becoming an entrepreneur. Wow. I don't really make a lot of decisions. I'm not used to making decisions. I'm not used to weighing out my options and doing maybe a pros and cons list or realizing the worst case scenario is not that bad. And all these different things we'll talk about in a moment. But the point here is that I was not used to making decisions. And this is just a reality a lot of us have to just come to terms with. If you're coming from a job or even if you're coming as a student, everything is given to you, and you don't need to decide anything. You just do. Now we enter entrepreneurship. Now, it's interesting because Farida said, I'm new to entrepreneurship, so there's a lot of decisions I got to make because I'm new. Well, I'm here to tell you, Farida, that yes, it may feel like you have to make a lot of decisions as a new entrepreneur, but you're going to have to make even more decisions, and decisions themselves become bigger and bigger. The impact those decisions have will have greater consequences as your business gets bigger. So this doesn't go away. What does happen, though, is that you just get better at it. And this is the mindset I want to pass on to everybody who's listening. Decision making is a skill, okay? It's just like any other skill. Whether it's playing the piano or shooting a basketball or writing or drawing or public speaking, whatever, it's a skill that you can build. That is the key here. The better decision maker you become, the better the quality of your decisions. Many people think that, you know, it's just binary. Either I made the right decision or the wrong decision, or they think I'm just gonna get lucky for somehow and choose the right decision, or I'm gonna be able to make the best decision for me with zero practice or skill, I'm just gonna happen to make that decision, and that's that. No. Decisions have a lot of nuances. There's different ways you can implement things. There's different ways you can decide things. The outcome of your decisions will vary. But the point here is that if you want to make better decisions, if you want to get making decisions, make more decisions, okay? So this is what I mean. It's an opportunity. The fact that you are making decisions in the beginning of your business, this is good because you need to get your reps. You need to get a lot of decisions under your belt to feel comfortable with the process of you making decisions as painful as that sounds like, oh my gosh, I'm gonna have to go through this over and over until it starts to feel easier. Yes, that's really what it is. It's just like if you're learning how to ski, you're gonna fall down a lot in the beginning before you start to get used to it. But rarely anybody gets on a pair of skis for the first time and never falls and never goes through a little bit of pain. Same thing with decision making. You're gonna make some bad decisions. Just accept it, learn from those bad decisions. And the best way I can illustrate this is with the game of basketball. Right. As you may know, I love basketball. But one of the pieces of advice that the great basketball player, the great Laker Kareem Abdul Jabbar gives to young basketball players is when you shoot the baske ball and you miss, don't worry about it so much. Don't beat up on yourself when you miss. Instead, ask yourself what went wrong? And with basketball, it's one of four things. Too long, too short, too much to the right, too much to the left. That's it. And just correct yourself. So when you make a decision that's not that great or maybe didn't get you the result you're looking for, take a beat, take a minute and just say, hey, okay, this didn't turn out the way I wanted it. That's okay, don't beat yourself up. Let's learn from it. What can I take away? What went wrong? Well, I made this decision and this is what happened. And what's great about decisions is that it's very clear why it's a good decision or a bad decision in hindsight. And you can evaluate what went wrong and how it went wrong so that the next time you're going to make a decision, you can factor in some of these things. Now, many people use different strategies when making a decision. One of them is having a timeline so you don't keep delaying the decision saying, hey, I gotta make a decision by the end of the week. A lot of people do pros and cons lists, like I mentioned, to kind of evaluate what's the best decision for you or your business. Many people go with the what's the worst that can happen? Type of decision making. This often makes them understand what is the risk involved here with the, with the actual decision, if something really bad could happen as the worst case scenario, then you're going to be a little bit more conservative with your decision making or with the risks you're going to take with this decision. If the worst thing that can happen is not that bad, then maybe you'll be a little bit more riskier, take a bigger leap of faith or push yourself a little bit in that decision making. So my advice is, if you're second guessing yourself and that's stopping you from making a decision, remind yourself, I got to make decisions. I got to make a decision so I can make better decisions. And a lot of people, when they don't make a decision, when they take a long time to make a decision, that kind of stops them from other opportunities and other chances to make the next decision and the next decision and the next decision which will allow them to build their muscles. It's like somebody who is learning how to ski and they're at the top of the slope and they're just looking down the slope and they're like, should I go down or should I not go down? Which way should I go? Right? Should I go left? Should I go behind that person over there? Maybe I should wait until the wind dies down and they're going through all this. And in the meantime, they could have been down the mountain and up back again, doing another rep, doing another run to build their muscles on the skis. Instead, in this example with skiing, you're on top of the mountain, you might say, should I make a left? Should I make a right? Okay, let me go left this time. Next time I'll go right. What's the worst that can happen? Well, I can fall. And luckily I know how to control my speed so I can slow down before it gets out of control and I get really hurt. But I can just literally just slow down and fall to my side. I'll be all right. So even if right is steeper than left, I'm going to be fine and I'll learn. And then next time around, I'll go left and it'll be more of an enjoyable run. Done. Let's go and have some fun. There you go. This is just an example, but this shows you that you need to get the reps in to make better decisions. Here's something that not a lot of people are going to tell you. This gets harder as your business grows, as you get more employees, as you make more money, as you have more clients and more customers and more responsibility. Every decision matters even more. And the pressure to make a good decision, and I say good, not the right decision, is really, really prevalent. It's really in the back of your mind. But luckily, it's like a Mercy. You don't get to that level of business without making a lot of decisions, so you feel comfortable making those bigger decisions. Now, I mentioned good versus the right decision. There's no right or wrong in decision making. There's levels, there's degrees, so to speak, on the scale of decision making. You can make a mad decision, but it's not the worst decision ever. You can make a good decision, but it probably is not the best decision. And what I've been trying to do in my career as an entrepreneur is I just want to have as many good decisions as possible. I'm not so worried about best decision. I want to average more good decisions than bad decisions because bad decisions can really hurt your business, especially as you get bigger. So I try to avoid bad decisions as much as I can, but if it does happen, I try to learn from it because I know I have made bad decisions and I've made bad decisions recently. And that's just part of doing business. I learn from it, I look back and I say, hey, you know what? I've made more good decisions than bad ones. I'll probably be all right.
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To wrap up today's question from Farida. How does she stop second guessing herself and make a decision already? Well, I offered a few strategies today. Understand that you have to change your mindset and understand that decision making is a muscle. Make more decisions and you will find it easier to make decisions and be confident with your decision. After you make a decision, you might feel like, oh, did I make the right decision? Was this the best decision? You start second guessing even after you make the decision. What I like to do is I just like to have a quick, short review. Just like if I had a bad decision, I want to learn from it. Even if it's a good decision, I just review. Okay, how does this affect the business? This decision? Okay, this was good. Is there anything I could have done better in that decision making process or in what I implemented? Well, I could have done this, this, this. Can I still do it? Maybe I can do it now. Okay, let me do it now. If not, next time around, I have to make a similar decision, I need to remember this. If you're not good with remembering things like this, create a system, create a document, put it on your Google Drive so you can find it on your phone easily and you know, have titles of types of decisions and write down your notes. It's okay to do this. If you are still kind of nervous about making decisions, I encourage you to make as many decisions as you can even outside of business or work. For example, if you're going out to eat and your party does not know what to order, be the one to make a decision. Take it on yourself. Say, hey, what do you guys think about? Let's have this, this, this and this. Get comfortable being a decision maker. If you and your family are going on holiday and you're trying to decide should you stay at this hotel or this hotel, say hey, can I make that decision? If you're not normally the person that makes the decision, put your hand up. Get used to making decisions on things that are non business. Even again, decision making is a muscle. Let's work on that muscle. Let's pump it out so that way, hey, we feel more and more comfortable making decisions in the future. Thanks so much for listening to the $100 MBA show. Again. If you got a question you want to ask, I'll answer it right here on Q and A Wednesday. Just email me@omar00mba.net I'll make sure to answer right here on Q and A Wednesday. Before I go, I want to leave you with this. A friend of mine once said something really profound when it comes to decisions and it's that the more decisions you make, the more experiences you have, the more enriched your life is. And that's really true because when you're making decisions, you're actually going to take action. The more action you take, the more experiences you're going to have. The more experiences you have, the more informed and enriched your life is going to be. So that's a good thing. You want to have a full life. You want to look back at your life when you're old and gray and sitting on your rocking chair and saying, hey, you know what? I had a pretty good run. I had a lot of great experiences. I don't regret it. Rarely do people regret making too many decisions. Instead, it's not enough decisions. Thanks so much for listening and I'll check you in tomorrow's episode. I'll see you then. Take care. Introducing Fidelity Trader plus the next generation of advanced trading from Fidelity. Customize your tools and charts and access them seamlessly across desktop, web and mobile. For faster trades anywhere you go, try the all new Fidelity Trader Plus. Learn more about our most powerful trading platform yet@fidelity.com TraderPlus investing involves risk, including risk of loss. Fidelity Brokerage Services, LLC Member NYSE SIPC.
