Before Starting That Business, Ask Yourself These Essential Questions

Starting a new business is exhilarating. The rush of possibilities, the vision of success, and the potential for financial freedom are enough to make any entrepreneur dive in headfirst. But before you take the leap, it's crucial to ask yourself three essential questions. These questions will help you determine if your new venture is worth the investment of your time, energy, and resources.

As a serial entrepreneur, I constantly have to check myself. My brain is wired to spot opportunities everywhere—"I could do that!" or "Ooh, that would be a great business!" But I’ve learned the hard way that not every idea is worth pursuing. Let’s dive into these three questions that will help you make a strategic and informed decision.

1. Is the Potential Return Worth the Risks and Sacrifices?

Every business idea comes with a cost—time, energy, money, and even personal sacrifices. The question is: are the rewards worth the price you’ll have to pay?

For example, I recently toyed with the idea of starting an at-home bakery. It seemed simple enough: low overhead, flexible schedule, and a creative outlet. But when I really broke it down, I realized the reality meant waking up at 3 AM to bake, delivering products before dawn, and cutting into my already limited time with my child, my partner, and my personal life. Suddenly, the idea didn’t seem so appealing.

Before committing to a business, consider how much time it will demand, the financial investment required, and the emotional toll it may take. Will it pull you away from things that matter most? If the sacrifices outweigh the benefits, it’s time to reconsider.

2. Does This Business Align with My Long-Term Goals?

One of the biggest traps entrepreneurs fall into is getting distracted by shiny objects—new opportunities that seem exciting but don’t actually move them toward their ultimate vision.

I see this all the time with my coaching clients. They set ambitious financial goals, like buying 10 properties a year or setting up a trust for generational wealth. Then, a few months later, they invest in something that doesn’t align with that plan, like a long-term syndication deal that won’t pay out for years. When I ask, "How does this help you achieve your original goal?" the answer is often a sheepish "It doesn’t."

I’ve been guilty of this myself. At one point, I seriously considered going back to school for a master’s in women’s and gender studies. I was excited about the idea, but when I sat down with my financial coach, he asked me, "Does this help you reach your goals of building Audacious Founder and acquiring real estate?" The answer was a hard no. The degree wasn’t necessary for my business success—it was a distraction.

When evaluating a new business idea, ask yourself: Does this move me closer to my long-term vision? If not, it’s likely a detour rather than a stepping stone.

3. Do I Have (or Can I Acquire) the Resources and Support Needed for Success?

Many entrepreneurs underestimate both the costs of starting a business and their ability to acquire resources. It’s essential to take a realistic look at what’s needed to get your venture off the ground.

Some businesses require significant capital, like when I purchased a property that required an $80K down payment. I managed to come up with the funds by leveraging equity from another property, but the ongoing investment ended up totaling over $200K. While I made it work, I wouldn’t recommend that approach to everyone—it was stressful and financially draining.

On the flip side, many businesses can be started with minimal investment if you’re resourceful. But you must be honest about what’s required. For example, with my at-home bakery idea, I initially thought, "I already buy flour and apples—it won’t cost much to start!" But when I really analyzed it, I realized I’d need commercial-grade equipment, packaging, and possibly a delivery service. The costs quickly added up.

If your idea requires significant resources, consider whether you have the means to secure them. If you don’t, can you find a mentor, secure funding, or take a phased approach to growth? If acquiring what you need feels impossible, it may not be the right time to move forward.

Final Thoughts: Make Informed, Strategic Decisions

As entrepreneurs, we love new ideas. But not every idea is worth pursuing. Before starting a business, ask yourself:

1. Is the potential return worth the risks and sacrifices?

2. Does this business align with my long-term goals?

3. Do I have (or can I acquire) the resources and support needed for success?

If you can confidently answer these questions and still feel excited about your idea, go for it! But if you find yourself hesitating or realizing that a venture may compromise your bigger goals, it’s okay to walk away.

Entrepreneurship is a long game. Make sure you’re playing it wisely.

Are you ready to make bold, strategic moves in your business journey? Join the Audacious Founder Community for expert guidance, resources, and a network of like-minded entrepreneurs. Let’s build something extraordinary—together!