Chapter 35, Part 4: 3 Things I Ask Entrepreneurs in Their First 3 Years

After working with entrepreneurs through the Small Business Development Center and building businesses of my own, I've noticed that the biggest challenges in the first few years aren't always what people think they are. Most entrepreneurs don't simply need another marketing tactic. They need clarity. They need to understand what's actually happening in the business, what's happening inside themselves, and what deserves their attention next. So when I'm working with an entrepreneur in those early years, there are three questions I come back to again and again.

First: What is actually working? This sounds simple, but entrepreneurs are often so focused on what isn't working that they overlook the evidence sitting right in front of them. Where are your customers coming from? What are they buying? What do they keep asking for? What do people rave about? What comes naturally to you? What generates revenue without requiring an enormous amount of energy? Before you completely reinvent your business, I want to understand what already has traction. Strategy isn't about constantly creating something new. Sometimes it's about noticing the thing that's already working and doing more of it.

Second: What are you doing because you think you “should”? This is one of my favorite questions because there are so many invisible rules in entrepreneurship. You should be on Instagram. You should have a podcast. You should offer a course. You should charge more. You should hire a team. You should scale. You should wake up at 5 a.m. You should work seven days a week. But “should” isn't a business strategy. Your strategy needs to make sense for your goals, capacity, values, personality, resources, and season of life.

Third: What kind of business are you actually trying to build? Not what does the internet tell you to build. Not what would impress people. Not what sounds successful on a podcast. What do you want your Tuesday afternoon to look like? Do you want a seven-figure company with employees? A six-figure solo business with lots of freedom? A creative practice that supports your lifestyle? A business that lets you travel? Your answer changes your strategy. I've learned that entrepreneurship becomes much easier when you stop asking, “How do I build a successful business?” and start asking, “What does success mean to me?”