10 Questions That Will Help You Decide if You Have What it Takes to be an Entrepreneur

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Elisabeth Thomas28

I became an entrepreneur by mistake. No, seriously! I was a new mom. We had moved to a new town when I began searching for a corporate marketing position. With a nine-month-old on my hip, the job hunt was harder than I expected. While trying to figure it out, a friend asked if I would do social media and writing freelancing, and before I knew it, I’d launched a social media business. I would never have thought it would be a success, but it grew and grew.

Before long, I had an office space, employees, and more responsibilities than I had bargained for – it was overwhelming, but also fun! I had to learn many lessons in those first few years as an entrepreneur the hard way. 

Whether you come into entrepreneurship by chance, or on purpose, here are the ten questions I wish I had asked myself before launching my first full-fledged entrepreneurial venture.

1. Are you self-motivated?

It’s easy to daydream about becoming your own boss; the freedom, the lifestyle, etc. Still, the truth is entrepreneurship is not just coffee shops and in beautiful remote locations. It’s a lot of self-driven planning and effort to stay motivated when things seem to be falling apart, and stick with it through the tough spots. If you have a personality that flourishes as a self-starter without a roadmap, then you will make an A+ entrepreneur. 

2. Does your idea excite you?

This might seem like a no-brainer, but you would be shocked at the number of startups I’ve worked with that when asked, “do you use your product or service yourself,” they don’t, and when probed with, “how do you know people will buy it or use it?”, can’t actually give a sound reason. If you don’t need, want, or get inspired by your product, service, or business idea, you will likely have trouble making it a success. 

3. Is there a market?

“A market” doesn’t mean you need to know everything about who will purchase from you, but if there is no evidence of a market for your business, then you may want to rethink your idea. A good way to gauge this, according to Forbes, is to measure customer satisfaction, or if you haven’t launched yet, survey your network, family and friends for anonymous feedback. A good rule of thumb is that if one in three people say, “yeah, I’d use that or buy it,” then you probably have a market for your entrepreneurial idea.

4. Are you okay with uncertainty?

Really. Are you? Because if you take the leap into your dream entrepreneurial venture, you will be continually confronted with uncertainty. But that isn’t necessarily a bad thing! If you can focus on the small pieces of progress while staying focused on the big picture (remember, self-driven), then uncertainty can become your friend. It gives you flexibility and the ability to pivot, change and adjust as you go. You get to make the roadmap, and that is so rewarding.

5. Do you like being ‘the boss?’

Whether you are the boss of yourself or launch a team-driven company, leadership and decision-making will be essential to your success. If being the boss thrills you, great! If you struggle with this kind of responsibility or decision-making, you might want to reconsider whether entrepreneurship is right for you.

6. Do you have a business plan?

For my first business, I literally Googled “how to write a business plan” and then followed the steps! My business plan gave me much-needed direction, action items, and a timeline. Once it was completed, I could just run with it! Read this list of 22 Best Business Plans from HubSpot for more.

7. Know your deficiencies?

You might be a financial wiz, or maybe creativity is your strength; regardless of what your strengths are, it’s far more important, in my experience, to know your weaknesses so that you can quickly hire either vendors or employees to fill those voids. You don’t need to be good at everything to create a thriving business, but you do need to fill in the deficiencies so that your venture can grow!

8. What’s your brand story?

If you’re an entrepreneur looking to find investors, funding, or clients, your branding is going to be critical to your success. It is never too early to start thinking through and documenting the story behind your brand. Here’s a great blog post from Forbes on the importance of brand storytelling. It doesn’t need to be complicated, but it needs to make people feel something.

9. What’s your short-term mission?

It’s okay as an entrepreneur to build your business as you take flight. But creating a short-term mission can be extremely helpful in the beginning stages to keep you on track, and make sure you land on your feet. A short-term vision can be as simple as, “I want to bring in five clients at $1,000 per month in six months so I can quit my day job.” That’s it.

10. Long-term vision?

As you build your business plan, be sure to give significant time to your long-term vision. The short term is important to get you off the ground, but in order to thrive over time, you will need to have a vision that is about more. Nothing is too grand here, and it’s good to dream big so you have some time to strive for and look forward to attaining.


This article reflects the views of the author and not necessarily those of Fairygodboss.

Elisabeth Thomas is the founder of Womanhood Unwrapped and a Content Strategist at Godfrey Social PR. Thomas is an unashamed branding nerd, and writer for hire, and coffee addict. She's been a writer and marketer for over 15 years, with a natural affinity for all things digital. She loves helping clients tell their story, create digital marketing strategies, and build lasting relationships with target audience groups. Elisabeth is also a doting mom of two fabulous kiddos, a devoted wife, and an avid outdoor enthusiast. You'll find her hiking, boating, and camping in the Pacific Northwest with her family and two dogs in her off time!

What's your no. 1 piece of advice for someone hoping to step out on their own? Share your answer in the comments to help other Fairygodboss members!