MBA2346 Must Read: Stumbling on Happiness by Daniel Gilbert
2 Feb 2026 · 13 min
Omar Zenhom breaks down Daniel Gilbert's Stumbling on Happiness, exploring how we predict what will make us happy and why we're often wrong. The book argues that experiences matter more than possessions, and that simplicity beats complexity in the pursuit of contentment.
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This episode of the Hundred Dollar MBA show is brought to you by this Is Small Business Next Generation, a new docu series from Amazon. Hosts Andrea Marquez and Mitch Gilbert are a dynamic duo who host the show. I listened to episode one and it was refreshingly honest. I'll share a little bit about episode one later in the episode. This is Small Business Next Generation is out now. Go listen to it wherever you listen to podcasts. Hey, welcome to the $100 MBA Show. Powerful business lessons you can count on. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of Web and Arninja, an independent software company I started back in 2014 and today's episode is a must read episode on our Must Read Episodes. I share with you a book that has influenced me as an entrepreneur. I share with you its takeaways, its insights and why you should read it too. Today's must read is Stumbling Upon Happiness by Daniel Gilbert. I first read this book a little over 10 years ago. It was a pivotal time in my life. I was unhappy in my career as a teacher and educator. I was looking for a change. I was doing this business thing on the side for a while and I was trying to look for the answer to this question. What is happiness anyway? If I make this change, will I be happy? All I knew is I wasn't happy and I didn't know why. This book, Stumbling Upon Happiness helped me find those answers. It gave me a fresh perspective that I really needed and it stuck with me for years to come. And I want to share with you its takeaways in today's episode. Let's why this book really is not like any other self help book I've ever read and why it's one of those books that everybody recommends. Let's get into it. Let's get down to business. The author of Stumbling Upon Happiness, Daniel Gilbert, is a Harvard psychology Professor. He's known for breaking down the science of happiness. In fact, he has a very popular TED talk. You should check out. Just YouTube it. In the book and in the talk, he explains that as human beings, we have an extraordinary ability to simulate the future, to imagine what if, if I only had this in my life, I would be happy. If I only did this, it would make me feel joyful and ecstatic in life. And we'll play it out in our minds. We'll imagine what it would be to be rich or have more time or be healthy or look great. It's so clear to us. And therefore our mind plays this little trick where it thinks that if we do these things for sure we will be happy. And that's where the problems start. Our ability to kind of imagine the future is a double edged sword because we make decisions based on that. We think for sure it's gonna pan out that way, when in reality it doesn't. And then we get disappointed. We think that the next thing will make us happy. The next thing will make us happy. This book, Stumbling Upon Happiness. Its main job is for us to be aware of these tricks our minds play on us so that we can avoid these tricks and create our own happiness in life. There's a few kind of major insights in this book I want to share with you because they're pretty incredible. Now he goes into detail about these. I don't want to kind of ruin it for you. I want you to read the book and enjoy all the things that go with these kind of takeaways. But here it goes. The first thing is that our minds are built to fill in the gaps. The thought crosses your mind, what if I won the lottery? Our mind automatically fills in the gaps and starts imagining what your life would be, right? What house you'd be in, what are the things you would buy, what kind of admiration your friends and family would have for you. The problem is our brains are really bad at this. It's actually very, very bad at filling in the blanks. But our brains just keep on trying. The second big takeaway talks about like when you're making decisions and choices, especially when you're making purchases in life, vacations, homes, cars, whatever it might be. You should always base these decisions based on value and not on previous price. Our minds sometimes like to refer back to previous experiences. Let's say you're looking to buy a car and the car's price is a similar price to the price you bought your previous car maybe 10 years ago. And you might be thinking oh, this car is going to be just as good as my car when I bought it 10 years ago. I'm going to have the same kind of experience is going to be great. Instead of saying, well, what's the value of that price in today's day and age? What am I getting for this car? Actually, the reverse could be true too, where we think that just because we're paying more, we're gonna get more. Now, often that is true. You get what you pay for, but sometimes it's not, especially when you're paying for things you don't really care about. Focus on the value of what you're buying versus the price. And the third one I really loved is all experiences good and bad are better than no experiences at all. I know that sounds odd or strange, but having a bad experience te you something and it's an experience. It builds character. It makes you who you are today. This is why a lot of people will regret what they don't do more than what they do. So remember, bad experiences better than no experiences at all. This episode of the Hundred Dollar MBA show is brought to you by this is Small Business Next Generation, a new docu series from Amazon. I've jumped in and listened to a bunch of these episodes of this series and I want to share with you a bit about episode one, where host Andrea Marquez meets her new host, Mitch Gilbert, who is the founder of Oya Femtech Apparel, who's also a former winner of the Rice University Business Plan Competition and is one of the first 200 black women to raise a million dollars in venture capital. Andrea and Mitch walk you through the journey of raising capital, pitching to investors, and how to polish up your business plan so that you can get the best value for for your business. This is Small Business. Next Generation is out now. Go listen to it wherever you get your podcasts.
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Might be listening to this episode and thinking, what does this have to do with happiness? Well, it actually has a lot to do with it, because happiness is really just a state of mind. It's what you tell yourself. So, for example, if happiness to you is being ecstatic all the time, having no problems, having no challenges, no drama every day, being sunshine and rainbows, you will never be happy. Because this is not reality. Life is ups and downs. You always have challenges. People with money have problems. People without money have problems. People with great health have problems. People without great health have problems. I can go on and on. So how you define happiness is basically like the goalpost. It's like, this is what happiness equals. And the more simple your definition of happiness is, the better. You should always keep it simple. This is why when I was reading this book, it was like so many eureka moments. I was like, this is why when we were kids, when we're playing in the backyard, when we're having fun with our friends, when we look back at our memories, we think, man, those days were so, so fun and happy. Because it was simple. Happiness to us was not driving a Lamborghini. It was, for me, playing basketball with my friends on a nice summer day, coming home, mom, having dinner already eating and watching TV with my family. Very simple, very inexpensive. And I just accepted the fact that, hey, I'm not an adult. I don't get all these choices. I have limited choices. But there's happiness in these choices. There's happiness in playing with my friends. There's happiness in enjoying the weather and the cool breeze on a hot day. There's happiness of not having so many material things as a child that you have to worry about protecting these things and not losing them. Simplicity is happiness. Another thing that this book really reminded me is that experiences are everything. Memories are everything. When you look back at a memory, psychologists say that the memory, experiencing the memory in your head gives you the same amount of happiness as when you actually experience it in real life, in the moment. So you can relive that happiness over and over when you have an experience. And the reason really why experiences are so valuable and give you so much happiness is because our most valuable thing in life is our time. And when we spend our time doing amazing things When I say amazing, they don't have to be extravagant. They could just be things that give us joy and put a smile on our face. It could be going for a walk with a loved one. It could be having dinner with an old friend. You could be watching the game by yourself and cheering your team on. Seek out experiences. This is why I always tell entrepreneurs, if you have an opportunity to do something fun, interesting, go to an event, go to a conference, go to a meetup, go to some sort of retreat or something like that, you should sign up as soon as possible. The fact that somebody's made the effort to carve out an experience for you and present it to you and sell it to you, that is a gift. Should hop all over. Because those are the memories, those are the days, those are the moments that make up our life, that make a happy life filled with experiences. I highly recommend this book, Stumbling Upon Happiness. It's such an easy read. It's well researched. It's so convincing and I really left out a lot of the meat. I just wanted to give you my major takeaways. You might find a lot of different takeaways for yourself. It's very personal in a lot of ways. So go ahead, pick it up. Stumbling Upon Happiness by Daniel Gilbert. The paperback version is one I read. Fantastic, fantastic book. That wraps up today's episode. Thank you so much for listening to the $100 NBA show. Don't forget to hit, follow, or subscribe on your favorite podc, Apple podcast, Spotify, Overcast, it doesn't matter, we're on them all. But make sure you hit, subscribe or follow so you don't miss an episode and you get our next episode automatically. You also get access to over 2,300 business lessons in our archives. Go ahead and do that right now. Before I go, I want to leave you with this. Why did I talk about this book, Stumbling Upon Happiness? Because your contentment, your happiness is really essential to any success in life. If you're not happy, everybody will know, okay? Everybody will feel it. Your customers, your employees, your loved ones, your family, your friends. What's the point of all this? What's the point of starting a business and being successful and going after it if it doesn't result in happiness? We have one life on this earth. Let's make it count, right? Let's make it enjoyable. Let's make it rewarding. This podcast is about building and growing your business, but it's also about building and growing you. So it's good to mix it up with a book like this to put things in perspective. Thanks so much for listening, and I'll check you in Wednesday's episode Q& A. Wednesday I'll see you then. Take care.
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