Three Unhelpful Questions You’ll Hear When You Start a Business

And How to Turn Them Into Something Productive

Photo by Ekkasit Jokthong

Starting a new venture, whether it’s a side hustle, self-employment, or any role that ties your income to performance, stirs up plenty of anxieties. And one of the first places you’ll see this is in the questions people ask you when you share your plans. These questions, though well-meaning, often reflect more of the other person’s fears than your reality.

This post explores three common, unhelpful questions people ask when you're on the cusp of starting something new and uncertain. We’ll look at how to internalize those questions in a way that protects your dignity and mental health and how to enlist others to support your goals.

1. How will you get customers?

This is often the first thing you’ll hear when you tell people you’re starting a business or a revenue-driving role. “How will you get customers?” It’s a valid question, but more often than not, it’s really someone projecting their own fear of the unknown. Sales and client acquisition can feel like a mystical art when you’ve spent your career in a stable role where money and clients flow predictably.

What they’re really saying is: I’m afraid of putting myself out there and taking on the responsibility for bringing in money.

Instead of getting rattled, take a breath. The truth is, finding customers or clients isn’t magic; it’s just work. Like any other skill, sales and marketing are things you can learn and improve over time. Start with this response: I’ll observe how others in my field attract customers, and I’ll try those methods. If they don’t work, I’ll adjust until they do.

It may not feel like a particularly satisfying answer, but it's realistic—and it acknowledges that business-building is iterative. You learn, adapt, and keep trying. If you can shift the conversation with your well-intentioned questioner, you might even say: I’d love to hear any ideas you have for getting the word out.

What’s important is not to let someone else’s anxiety feed your own. Instead, ask yourself how you’re going to define success and keep moving toward it.

2. What if it doesn’t work out?

No one wants to give too much attention to this question, but it’s almost always on people’s minds. What if it doesn’t work? What if you fail? The real question they’re asking is: How can you handle uncertainty?

A perfectly valid response is: If it doesn’t work, I’ll try something else. This may sound overly simple, but it’s the truth. When you break it down, there’s no shame in walking away from something that isn’t working. Entrepreneurship, like any career, comes with risk, and sometimes the risk doesn’t pay off.

But the more valuable question to ask yourself is: How will I know when it’s not working?

The hardest part of working for yourself isn’t necessarily the work itself—it’s knowing when to stay the course and when to pivot. A professional service business or freelance career can take time to gain traction. It’s helpful to set some financial parameters for yourself, like: How much of my savings am I willing to invest in the business before I expect it to pay for itself?

Be cautious about hard deadlines or revenue targets, though. In some cases, these can be more demoralizing than helpful. If you tell yourself, I need to earn $100,000 by the end of two years, and you’re only at $99,000, does that mean the business is a failure? Instead, consider creating guidelines for your financial comfort: how much you’re willing to take from savings, how much debt (if any) you’re willing to incur, and when you’ll check in with yourself to reassess.

Another layer to this is understanding what personal sacrifices you’re willing to make. For instance, Are we okay cutting back on vacations this year to fund the business? or Will we reduce retirement contributions while the business grows? These are values-based decisions, and the answer will be unique to your situation.

3. Why don’t you just get a “normal” job?

When you’re working for yourself or in a sales-driven role, some people may wonder why you would take on so much uncertainty. In their eyes, a traditional job with a steady paycheck seems like the safer, more reasonable choice. What they’re really saying is: I value security over autonomy.

The reality, however, is that security in traditional roles is often an illusion. Jobs that seem stable can disappear overnight, whether through layoffs, company buyouts, or organizational shifts. So, instead of letting this question eat away at your confidence, focus on why you’re making this choice.

The appeal of self-employment or a revenue-driven role lies in the control it offers—you’re in charge of your income and your future. Yes, it’s riskier, but the payoff can be higher, not just financially but in personal satisfaction. So, how do you respond to someone who questions your decision? You might say: I want the freedom and flexibility to grow something on my own terms.

This is also a good time to remind yourself of your why. Maybe it’s about creating a life that aligns more closely with your values or a desire for more control over your work-life balance. Whatever it is, keep that front and center when the doubts creep in.

Turning Anxiety Into Action

While these questions can spark discomfort, they can also offer valuable opportunities to reflect. People who ask these things are often trying to help, even if it doesn’t feel that way. Instead of getting defensive, you can use these questions to clarify your own values, financial boundaries, and vision for success.

When someone asks what if it doesn’t work out?, use that as an invitation to articulate your contingency plans. When someone asks how will you get customers?, let it prompt a conversation about marketing strategies. And when they say why don’t you just get a normal job?, use that as a chance to solidify your reasons for pursuing this path.

By taking these anxieties and reframing them, you gain a clearer sense of your own goals and boundaries, making it easier to weather the uncertainties of entrepreneurship or revenue-driven roles. After all, the key person who truly needs to believe in your business’s potential is you.