MBA2474 Q&A Wednesday: Do I need to be more pessimistic as a business owner?
2 Feb 2026 · 18 min
Omar Zenhom tells Kathy that entrepreneurs don't need pessimism, just paired optimism and contingency planning. Run a "how could this go wrong?" exercise, verify trust in people, and replace underperforming team members when necessary.
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Hey oh. Welcome to the hundred dollar RBA show. Practical business lessons you can count on from the real world. I'm your host, your coach, your teacher, Omar Zenholm and today's lesson is Q and A Wednesday where we answer a question from one of you, one of our listeners. Today's question is from Kathy and Kathy asks am I too optimistic? Do I need to be more pessimistic? As a business owner I see the good in people and maybe trust them too much. I also see the big picture and dream big for our business. I often only see the bright side in the situation. Am I too optimistic? Do I need to be more pessimistic to be successful? Very interesting question from Kathy and I have an answer for her. I definitely resonate with you Kathy, because I am more of an optimistic person. I am more of a kind of person that tries to see the good in people, hope for the best and loves to dream big. But over the last 20 years in business I learned a few lessons on how to calibrate that and understand you could be optimistic but also have a contingency plan if things don't go to plan, if people do disappoint you, if things go sideways. And that doesn't mean being more pessimistic, just means being more prepared. I'm going to get into the details of this, what this exactly means, and how to prepare, how to approach trusting team members or colleagues or partners in business without getting burnt. Let's get into it. Let's get down to business. One of my favorite quotes and something that I've learned over the years in business is trust but verify, okay? It's okay to trust people, especially if they have a good reputation, if they've given you no reason not to trust them, but you have to verify that you actually can do what they're saying they can do, or they're going to to fulfill their end of the bargain or whatever it might be. The thing about entrepreneurship is that you have to balance this idea of being delusional that you can start a business in the first place, implement an idea from thin air, see it happen in the world, create it, sell it, scale it. You have to be delusional enough to believe you could do this, but at the same time, you have to be practical enough to understand what's possible, what's not, and to have contingency plans for things just in case they don't work out. This is what makes business so challenging, because you have to play both roles at the same time. There is no doubt that your optimism is helping you and your business. But lack of preparation, lack of contingency, lack of a battle plan just in case things fall through or don't work out will hurt you. You'll get stung a few times in your entrepreneurial career, and sometimes you get stung so bad you never recover. So this is why it's important to have your optimism, but to also be prepared. So let's talk a little bit about being prepared. What does that mean? Well, one of the exercises, thought experiments, I like to do, anytime I take on a project, I start a new idea, I'm creating something new in my business. Let's say, for example, you decide to start a new YouTube channel or create a new product or whatever it might be. But let's go with the YouTube example. The first thing I like to do is, is kind of flesh out the idea, write down how it could be successful. What does winning look like, how it's going to help the business, how it's going to help me, all that kind of stuff, all the positive stuff, all the things that I really want to get out of it. But then I ask the question, how can this go wrong? Okay, this is not pessimism. This is not being negative. This is not being a hater, okay? This is being smart. This is being strategic. And understanding that there are challenges, there are things that are going to prevent you from being successful. So having that moment and taking, you know, 30 minutes to brainstorm and take notes and ask yourself, how could this go wrong? How could this be not successful? Why is this a bad idea? Oof. That's a good one. Why? Because when you answer those questions, when you brainstorm and jot notes down, you now know what you're dealing with. You can then say, okay, I see all the negatives of it. I see the challenges that could come about. I see how this could be difficult. I can see how this could not work. And it's worth it. It's worth the hard work. It's worth the sacrifice. It's worth the risk of it not working for me to try it or not. It's not worth it. This exercise is highly effective, highly useful, and it just allows you to be honest with yourself. Okay? Honest with your business, your limitations, your budget. Everybody's dealing with constraints. It's okay to just be real about it and say, hey, this might not work because I might not have enough money to market it. Are there other ways I can make it work? This might not work because it might take more time than I expected. I might get burnt out, I might get stressed out. Whatever it is, put it all down. Be your own devil's advocate. Be your own person. That's going to be the opposing argument so that you know the positives and the negatives and what you'll have to deal with. So that's working with yourself. That's working with your business, with your ideas, with your implementation. What about people? What about the people on your team? What are the people you're working with? A lot of us, we're very optimistic about the people we hire and we hope for the best. And when they don't do their best or they fall short or they screw up, even we get disappointed. We feel like, oh, you know, I really believe in this person. Why didn't they, you know, fulfill my dream of them? Why didn't they do what I expected them to do? And that makes us feel bad. It makes us feel like business sucks. I don't want to do this anymore. People are always disappointing me. This is a really bad cycle to get in. You have to understand that if you're going to build a business of significance, you're going to have to work with other people. You're going to have to do it with other people. You're going to have to have a team around you so that you are not stressed. And you are building something great. And that means you're going to have to deal with this dynamic of making sure there is constant communication with your team members. I'm not going to lie to you. In the past 20 years of building businesses, I've had people that disappointed me. I had people that fell short. And they fall into two categories. Okay? The first category is they are falling short. They're not fulfilling their obligations, they're not doing what I'm expecting because they're incapable. They don't have the skills yet. They need training, they need time, they need advice, they need to be shown how to do something. And sometimes you can train them and you can work with them and improve their skills. And sometimes, you know, the results you're looking for are not going to come in time for when you need them. Meaning, you know, it's going to take them maybe six months to a year to get to the point where you need them to produce the work that you need right now. Right? And in that case, you're going to have to find somebody else. And that's just the reality. That's one camp people are incapable. But there are people that will disappoint you, that are capable but are just falling short. This is because they're distracted, they're busy, they have problems, maybe at home they're taking advantage, right? They are unmotivated. They don't really feel. Why should they give a hundred percent when maybe 60% is enough? This is another camp people that are falling short, disappointing you. They are capable of doing what you want them to do, but they are just falling short for all these various reasons. Here's the truth. Both situations are problematic. Both of them need fixing, right? The bottom line is that you need to get results. You need to get the work done. You need to produce for your customers. Your customer is the ultimate stakeholder. If they're not being served properly, if they're not getting provided excellence through your business, you're not doing your job. You need to make sure that happens. So in these two scenarios, you need to figure out one, Do I need to replace the person that's incapable? Do I need to find somebody else? Do I have time to train them and make them, you know, skill them up so they can get to where they need to be so that we can be able to deliver that kind of work? If so, get to work, figure out what skills they need, train them up, getting them courses they need, get them to read the books they need to read. You train them yourself, whatever you need to do, start moving towards that. Because if you're not working towards a solution, you're just going to fall into that cycle again. Disappointment. Oh, they didn't do it again. Why are they not that great? What's happening here? I'm getting frustrated. If you're not working towards a solution, doing something, you're just going to get more and more frustrated. What's going to happen really is that as you're training them, they're going to surprise you. You're going to get less disappointed. Not completely undisappointed, but you're going to get less disappointed. You're going to start to feel like, okay, that's a little bit better than the last time. Okay, it's not perfect, but you know, and that's a good pattern to be in the second camp of people that are capable but are just falling short. In my opinion. You do not waste time. Cut them loose. You have to fire this person immediately. Why? Because the problem is not in your control to solve. What do I mean by that? They have a problem at home. They have an attitude problem within themselves. They're all. These are all things that you can't change. They have to decide to change themselves. The problems at home have to go away. You can't do that for them. Right? You can't help them out in that way. They're not willing to change. They don't have the solution themselves or they would have solved it before. So it's really a waste of time and money for you to continue and hope that they're going to actually provide and do their job. Cut them loose immediately. Say, hey, thanks. You know, give them what they need to do to say goodbye, you know, whatever you agreed on in your contract. The point here is that it's time for you to find a new person. This is, in my experience, the last 20 years, the only way to deal with this situation because you're really risking your business and the results for your customers on the fact that they can solve the problem that is out of your control.
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So, to go back to the original question, do I need to be more pessimistic? No, you just need to be more strategic. You just need to be a little bit more prepared for when things go wrong. And this is why I'm giving you these plans of action just in case they do go wrong. And also, you know the methodology like that, brainstorming, where you can figure out how can go things go wrong and you can come up with some solutions before they go wrong. Right. The last most common way people get disappointed and feel like maybe they need to be a bit more pessimistic, quote, unquote, is when they get disappointed by their customers. The customer is disappointed, they're complaining, they're flooding your inboxes, or they're killing your customer support team with, you know, support tickets. In this situation, you can't really change your customers. You can't really change these customers, the people that are disappointing you. The best thing you can do is find a better audience. This means that whatever you're offering is not a good fit for these people. The people that you are selling to. You have a mismatch here, okay? They're being disappointed, you're being disappointed by them because they're disappointed. It's a real mess. And in my experience, sometimes you just get it wrong. You have the wrong audience. You think you're pitching to certain people, and you realize, oh, these people actually don't value what I have. And in this case, you need to start thinking about who are the people that have the problem that I solve, are really eager to solve this problem and have some energy, have some motivation to make it happen. That means they're willing to spend money on it. And this means you're changing your target market, getting more aligned customers than the ones that you have right now. There's another thing you need to consider, and we got to be honest ourselves. Am I actually providing the best value possible through my products and services? Maybe you need to get better. Maybe the customers are fine that you have, but your products and services are not actually solving their problem completely. Okay, Maybe it's leaving them hanging, maybe it's not leaving them satisfied, maybe it needs something else. And by the way, that's okay. You can improve your product, you can raise your prices and absorb the cost of improving your product and people will be happy to pay if it solves a problem completely. For example, I've been on different calls with a lot of different agencies, marketing agencies, because we want to run some paid ads for the hundred dollar mba. And I've spoken to a lot of agencies over the years and in this period and one of the reasons why I don't sign up with an agency is because they don't solve my problem completely. They do one part of the equation, but they don't do the whole thing. And I then have to find somebody else to, you know, write my copy or I have to find somebody else to create the creative or I have to find somebody else in my team to write, create the landing page. I want somebody to do the whole A to Z, the whole process of converting my customers. And when I found that agency, that was a no brainer for me. It was like, yes, this is exactly what I'm looking for. Somebody who's gonna do the whole job, solve my whole problem. Sign me up. So there you have it, Kathy, you don't need to be more pessimistic. You just gotta be more prepared. Okay? Keep that optimism that you have. The optimism that thinks big picture, that wants great things, that wants to achieve fantastic things, wants to have a brilliant product out in the marketplace that wants to compete and be number one. That's great. You need to keep that alive. Your team needs that motivation. That team needs that vision, okay? Don't lose that flame, okay? But you have to marry that. You couple that with a contingency plan when things go wrong, when things don't go well. And I know how to deal with that, whether it's my product or business or service or idea or people or my customers. Thanks so much for listening to the $100 MBA show. If you got a question you want to ask, go ahead and email me over@omar00mba.net I answer all those emails myself. Actually it takes me a little bit of time, but I still do that because I like to stay in touch with our audience, help people directly. Because I was where you are right now. At some point in my journey as an entrepreneur, I know how it feels. I know the problems that you go through. I've probably gone through them several times, so I want to help you get through them. I've built my businesses, I've made my money and I want to give back now. And this is the whole purpose of the $100 MBA. So go ahead and email me Omar MBA net. I'll make sure to answer it via email. And if you like, I can share the coaching and the advice on a Q and A Wednesday episode before I go. I want to leave you with this Optimism is fantastic. You need it because it's going to help drive you through the hard times in business. But you can't shun away feedback or criticism because that stuff is important to listen to. You don't have to implement everything, but take it in in your knowledge bank. Filter it the way you want to filter it because feedback is power. Anytime somebody's talking and giving you information or giving their opinion about your business, your customers, your whatever it is, this is free advice. This is free information. This is free data. Okay? Take it on. Even if you think that 90% of it is rubbish, there might be something there that you can use, or it might trigger a thought that can allow you to improve your business in some way. Be open to feedback. It's not hate, okay, because it's going to help you tremendously. Thanks so much for listening and I'll check in the next episode. I'll see you then. Take care. Of. Hey Fidelity. How can I remember to invest every month?
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