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7 Questions I Wish I'd Asked Myself Before Starting My Own Business

By Taylor Wilkinson
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Before I dive into this list, I feel the need to give my fellow mom entrepreneurs out there a heads up that some of these questions are brutally honest.

Sure, there are the generic questions you should ask yourself before starting a business, like "should I hire a team?" Or "how do I file taxes on my new income?" But in hindsight, there are several, more personal questions that I wish I'd asked myself before I started my own jewelry company, Taylor Wilkinson Designs.

In the interest of being honest about my experience, I'll admit my journey was paved with countless panic attacks — in carpool lines, in grocery stores, at parties — but also with thrilling triumphs. I've loved seeing my pieces worn on the red carpet and I've had people whom I've never met send me messages saying how much they love what I'm doing, and how proud they are of me. There's no question that starting your own business is fraught with challenges, but the twists and turns are what entrepreneurship is all about.

Of all the things I wish I'd asked myself before starting a business, most of them had to do with ensuring that my personal priorities were in order prior to taking on such a big project. And while some of them were answered by the time Taylor Wilkinson Designs launched, there are many others that I'm still working through.

Here are seven questions that I wish I'd asked myself before starting my own business.

How Important Is This Business To Me?

Ilya Pavlov/Unsplash

I've always loved jewelry, but I never thought that I could actually become a designer. I was busy. I was distracted. I was raising children. But when, at 38 years old, I had that famous "ah ha" moment, I knew it was time to launch my brand. I thought through what type of jewelry I wanted to design, and I knew I wanted my pieces to be edgy and geometrical, but... that's pretty much all I had.

So I Have My Concept, But Now What?

This is the least sexy part of the entire entrepreneurship journey, at least to me. It's the trial and error, the meetings with an attorney, and the search for a business consultant. These people are all vital to the success of your dream, so don't be afraid to leverage their experience and expertise.

How Am I Going To Pay For All Of This?

Truth time: Figuring out your business plan can be a huge headache and might feel completely overwhelming, but doing your research at the onset will pay off in the long run. I was able to find and apply for grants for women-owned businesses, which helped get me off the ground. There are also plenty of available loans to help small business owners get started.

Make the time to do some digging, and be sure you know all your financial options before you decide which path is best for you.

Am I Ready For All Of The Personal Changes That Will Unfold?

Ashley Batz/Romper

Some days I'm riddled with crushing mom and wife guilt, and I've asked myself more than once whether this is all worth it. I've been through weeks-long stretches of not seeing my friends, tuning out during conversations with my husband, and rushing my kids off to bed.

It's normal to make your business your top priority, but we all need to take time for ourselves and for our families. I try to take an hour of personal time everyday, and I try my best to clock out when I'm having dinner with my kids and my husband — but sometimes I fail, which brings me to...

Am I Prepared For Failure?

As confident as I was that my business would be successful, the possibility of failure was still something that I needed to prepare for. I harnessed my fear and turned it into the driving force that motivated me to bust out my sketch book, call members of my network, and actually consider the notion that sometimes, failure could be a positive thing.

Failure is deeply personal and while it does hurt, it's important to remember that it's not always an ending, and often can be an opportunity to learn and grow.

Am I Prepared To Succeed?

My definition of success changes from week to week. One week it means sending out 20 press kits, and the next it means getting 30 new orders or landing an amazing retail opportunity.

Don't be afraid to set one main goal that defines your ultimate success and keep chipping away at it, but don't let that stop you from patting yourself on the back when you achieve smaller milestones along the way.

Am I Prepared To Have Other People Question My Choice?

Hannah Burton/Bustle

I've had so many others question my choice to start my own business at this point in my life. Some people simply don't understand my need to achieve something more, and to be honest, that's OK.

Remember: This is your dream, not theirs. You hold the keys to your own success and at the end of the day, that's the only thing that matters.