Are You Ready to Start a Business? The Questions Every Entrepreneur Must Answer First

People ask me for advice all the time, especially when they’re new to entrepreneurship. One of the most common questions I get is...

"I have this idea—do you think I can turn it into a business?"

My first response is always,

"How long have you been thinking about this?"

That question helps me figure out if it’s just a passing thought or something they’ve really been mulling over and answer imnmediately.

"Just now, actually" — Don’t do it. "

For years" — Tell me more.

Then, I usually ask if they’re happy with their current lifestyle and if they’re really ready to give it all up to dive into the uncertainty of starting a business. This helps me see if they’ve really thought it through or if they’re just being overly optimistic.

"Sure, if I can quickly get to a point where I can take home the same wages" - Don’t do it.

"Well, I’ve talked it over with my partner, and we think we can make it work" - Tell me more.

"Yeah, no problem—I’ve seen others do it, so I’m confident I can too" - Don’t do it.

In my experience, the answers to these questions quickly show who’s serious about making the leap and who’s just toying with the idea of entrepreneurship. It’s not just about having a good idea; it’s about understanding the sacrifices, risks, and long-term commitment it takes to turn that idea into a real business.

Then after they tell me more about their idea and if it looks like it could be a goer I suggest they go away and with their partner answer these questions together, honestly.

Why do I want to start this business? What’s really driving me here? Is it something I’m passionate about, a market gap I’ve spotted, or something else entirely?

Am I solving a real problem? Does my idea actually fix something that matters to people? Who would be my customers, and why should they care about what I’m offering?

Do I have the skills and knowledge needed? What am I good at, and where do I fall short? Do I know enough to pull this off, or will I need to learn new things or bring in others who can help?

Am I financially prepared? How long can I go without a regular paycheck? Do I have the money, or access to money, to get this business off the ground?

How much am I willing to sacrifice? Am I ready to make big changes in my lifestyle, give up time, and maybe even strain relationships? How much uncertainty and stress can I handle?

What’s my backup plan? If things don’t go as planned, what’s my Plan B? How will I pivot, and when will I know it’s time to call it quits?

How will I measure success? What are my goals, both in the short and long term? How will I track progress and know if I’m headed in the right direction?

Who is my competition? Who else is out there trying to solve the same problem? What makes my idea stand out, and why would people choose me over them?

Do I have a support system? Who can I turn to for advice and support? Do I have mentors, a co-founder, or a network to help me navigate this journey?

Am I ready for the long haul? Do I understand that success isn’t going to happen overnight? Am I prepared for the ups and downs and willing to stick with it, even when things get tough?

Then after all that, if they’re still okay to make the leap from a secure paycheck to the uncertain world of startups, I wish them well and say,

“Let me know if I can help in any way.”

Because no matter how prepared they think they are, the journey ahead will be full of challenges. Starting a business is tough, but with the right mindset, a willingness to ask the hard questions upfront and some solid support, they’ll be better equipped to handle whatever comes their way.