5 Questions You Need to Ask Before You Become an Entrepreneur

This post includes adult language. Reader discretion is advised. 

As someone who loves and appreciates her full time job, but has a major entrepreneurial itch, I’m a huge fan of side hustles. Side hustles can take very many different forms: you take your existing career expertise and turn it into an online course, you start a blog, you start a business from scratch, you sell on Etsy, you join a multilevel marketing company or direct selling company like Beachbody or LulaRoe or Stella & Dot… All of these are legitimate side hustles, and if you think you might want to follow this path, I challenge you to answer (and write down the answers to) the following questions.

1. Why are you doing this?

Is it for the challenge? Is it for the income? Is it for some other reason? Make no mistake, starting a business is tough – the highs are incredible high, and the lows are incredibly low. When you have moments of self doubt and start to question why you’re doing this, the answer to this question will keep you going.

2. How much time are you willing to invest? 

If you believe your Instagram feed, you might think that people start a business and success falls into their lap, and life is glamorous photo shoots and vacations. This is a lie. It take a tremendous amount of work to start and grow a business – I’ll be honest with you, I work ALL. THE. TIME. Every evening, every weekend, sometimes over lunch, and even in the mornings on occasion. It is a no-joke commitment, and this is not exclusive to me. At some point your business will become a finely tuned machine and you will grow your team and outsource and you can then adopt a 4-hour workweek and all that good stuff, but the beginning is a hard slog.

3. How much capital are you willing to invest? 

Every business, even a blog, involves some sort of capital investment. You may be going, “whoa wait, but blogs are free.” And you’re right, but you still need to buy a domain name. And if you’re using a site like squarespace (which I do), then there’s a hosting fee. Unless you are a graphic designer or a web guru, you may need some help creating your online space too. You probably also want a photoshoot so you have great photos for your launch. And what about business cards or social media ads? If you’re selling a product there’s an inventory cost. Your totals investment may be as low as $20/year for your domain name, or as much as $3000, which is what I invested in my business to start up. Since then, my investment and my business have grown, so my capital needs are an ongoing. Now you could also get outside capital, but that’s another story for another time. But the bottom line is, how much can you invest personally, and how much do you need to raise?

4. How do you feel about failure? 

Most start-ups fail. This is a fact. And while it is entirely possible that you are not one of those stories, it is still highly likely that you will fail in some aspect of your business. Perhaps it will be a launch that doesn’t go as planned, or a product that you love that ends up being a total dud (this happened to me). Perhaps you might struggle growing your social media following, or your email list — there are endless number of things that you can and will fuck up. How do you feel about that? Do you fear failure? Do you take them in stride? Do you linger over them? Can you get back up and keep going? How long will you allow yourself to fail before you walk away? There are no right or wrong answers to these questions, but you need to know it might happen.

5. How do you feel about success? 

What does success mean to you? What will it look like? How will it make you feel? What happens once you reach a success measure? Do you reset? Will you give up control? How do you feel about hiring? And firing? Will you want to exit a successful business? How will you decide when you exit?

This one is even more challenging for me personally than failure. I’m 100% ok with failure, but success could really complicate things for me in the sense that I don’t want to give up my day job, but a certain level of success will change how I approach it. Again, there are no right or wrong answers, and frankly, they will probably change with time, but sometimes success can be harder to deal with than failure – you may grow faster than you’re prepared to, and its good to have some barometer for your next steps.

To be honest with you, I didn’t answer any of these question (besides the one about capital) when I first started Bombay Taxi Boutique, and honestly I wish I had. My first six months were definitely a struggle, and I considered quitting more than once, but I’m glad I stuck it out – I had my first taste of success, and now I want more! I can’t wait to see where this journey takes me. Where will yours take you?

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Shibani Faehnle

Shibani is a banker by day, and an entrepreneur, lifestyle blogger, spin instructor, wife, and mom to three rescue pups by night. She started her online jewelry boutique bombaytaxiboutique.com in 2015. She has a weakness for ice cream, loud pop music, 90s hip hop, and texting in ALL CAPS. She secretly wants Andy Cohen and Bravo to hire her to be on Real Housewives of Cleveland.

1 CommentLeave a comment

  • Yes! I was just listening to a podcast this morning that said, “what you put in, you’ll get out” referring to both financial and good ol fashion hard work. Also, failure is a part of the process, I like to think of failure a information gathering. “Failing forward” is something I live by! Thanks for sharing, Shibani.

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