Entrepreneurs ask impossible questions. They want certainty, to know that their idea will work, if their price will resonate, and if their strategy will be successful.
Are you wasting time looking for an answer that no one can give you?
A student came to my office hours for the sixth time this semester. Punctual as a clock, he sat down at my desk and asked my opinion on another iteration of his startup idea. This time, I wanted to know what I thought about a new feature I’d been thinking up. Last time, it was a question about your pricing model. Before that, he was looking for feedback on his presentation.
“Do you think this will work?”he asked me, showing me some slides and eagerly awaiting my “expert opinion.”
But I couldn’t give it to him. And not because I don’t have experience giving advice on startups; Literally, it’s my job. In fact, I have enough experience to know when an entrepreneur is asking me to answer an impossible question.
Simply put, there are three impossible questions in entrepreneurship that no one—not a mentor, investor, client, or teacher—can answer for you. These are questions that can only be answered through action. They require trying, experimenting, failing and learning.
The three impossible questions are:
The first, and perhaps most common, is whether someone will be interested in what you are creating. Is there a market for it? Will people want it? Will they be willing to pay for it?
Unfortunately, no amount of brainstorming, strategizing, or Googling will answer this question. I can’t answer it either, nor can your investors or your mentors.
Because? Because customers do not behave as we expect.
For example, think about a company like Airbnb. If the founders of Airbnb had sat in my office in 2007 asking me for advice on their business idea, I probably would have laughed them off. Renting beds in strangers’ houses? Letting strangers stay at your house? It sounded absurd, until it wasn’t.
Airbnb didn’t succeed because some mentor or investor thought its idea was brilliant. They were successful because they launched it, tested it, and learned from their first users. They discovered that, yes, people would rent extra rooms—who would have thought! That validation came not from an “expert” who thought it was a good idea, but from real-world experiments.
The same goes for you. If you want to know if customers will want what you’re creating, there’s only one way to find out: do it! Put it in front of people and let them tell you, through their actions, not their words, if they want.
Another common question is: “How much should I charge?” Entrepreneurs become obsessed with the idea that there is a magic formula that guarantees success. Spoiler: there isn’t.
Price is not something you decide in isolation; It is something that the market decides for you.
Think about this: if you set the price too high and no one buys, the market is telling you something. If you set it too low and people buy but you don’t make a profit, the market is also telling you something.
The market is much better able to tell you if you’ve set the right price than anyone, because price is not a static decision, but rather an ongoing conversation with your customers. It’s something you learn through trial and error and it constantly evolves along with your product, the market, and the world.
Opinions don’t matter. The only thing that matters is whether your target customers see value in your product at the price you set. And the only way to find out is—you guessed it—put a price on it and see if people are willing to pay it.
The third impossible question that entrepreneurs always ask me is whether their strategy—whether marketing, sales, or product—is the right one.
Questions about strategy are complicated because they depend on many variables: the market, the competition, the moment, not to mention the specific objectives of the entrepreneur executing it. Strategy, like pricing and product-market fit, is not something you discover in advance. It’s something that evolves over time and that you constantly adjust.
It’s just as important to remember that no one starts with a perfect strategy. They start with their best guess, collect data, and adjust as they go.
I often have to remind entrepreneurs: “There is no perfect strategy. The best strategy is the one that gets you going, because once you get moving, you can start learning.”
I understand why entrepreneurs ask impossible questions. They want certainty. They want to know that their idea will work, that their price will resonate, and that their strategy will be successful before they start, to make sure they’re not wasting their time.
But that kind of certainty does not exist in entrepreneurship. More importantly, if you spend too much time searching for certainties, like the student who kept coming to my office hours looking for impossible answers, you will never get your startup off the ground.
In the startup world, the answers aren’t found by talking to mentors, reading books, or analyzing case studies. Answers are only revealed through action.
In other words, if you’re still wondering, “Will this work?” or “What should I do now?”, it’s time to stop. You’re wasting your time trying to find the perfect answer. Instead, start testing. Launch your product, talk to your customers and let the market give you the answer. After all, the market is the only thing that can tell you with certainty if your startup is on the right path.
