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1323 6th Ave N.
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The Skillery is a Nashville coworking space with resources and programming for freelancers, entrepreneurs, small teams and independent professionals, all aimed at making work meaningful, satisfying and unabashedly fun.

Starting a Business: 5 questions to ask yourself before launching

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Welcome to our blog, where we share stories and profiles of the entrepreneurs and events that call The Skillery home.

Starting a Business: 5 questions to ask yourself before launching

Matt Dudley

CO.STARTERS at The Skillery

We’ve entered week two of our current CO.STARTERS at The Skillery cohort, and while those entrepreneurs are working, testing and tweaking, we’re sharing a weekly blog series focused on what they’re focused on: Starting a Business.

This week’s installment: pondering some of the questions we need to ask ourselves before diving into launching that creative business idea. 

Your business idea might be a brilliant one, but any seasoned entrepreneur will tell you: It’s not the lack of a good idea that holds most hopeful entrepreneurs back, it’s execution. Giving your business its best chance for success means nailing the execution part — which takes time, resources, the help of strategic partners and/or mentors and a really good understanding of your own strengths and weaknesses. Before you leap, give some thought to these five questions:

5 questions to ask yourself before starting a business

What kind of time do you have available to dedicate to your business? 

Take honest stock of your day. How many hours do you spend sleeping? Eating? Working? Preparing meals? Watching Netflix? And how many hours do you have left to work on your business? (Hint: It’s less than you think.)

Before you dive in, be honest with yourself: Do you really want to spend that free time slaving away at an endeavor that may never bear fruit? And if you need more hours in your day, are you willing to sacrifice your free time, your recreation time, your family time, to make room for the business? 

Saying “no” to that question doesn’t mean that you’re a failure before you start, or that you’ll never get that business off the ground. It might just mean that the timing isn’t right yet. If you keep feeling drawn to exploring your business idea, keep asking yourself this question, and keep thinking about how you can carve out the time you need. You might find that with some focus and some shuffling, the timing lines up.

What are you truly great at?

In the early days, particularly if you’re launching your business solo, you’re going to need to rely on and leverage your unique strengths. What are they? Are you a fabulous designer or craftsman? Are you a terrific connector, capable of getting groups of people together in perfect harmony? Where do you truly excel? Taking real, honest stock of where your strengths lie will help you dig into the next question, which is a key part of getting over the early-days hump.

What do you truly suck at? 

Everyone is bad at something, and even though early entrepreneurship does ask you to wear a jumble of different hats, it’s important to grasp which ones really don’t fit. Maybe you’re too uncomfortable to excel at sales. Maybe public speaking makes you itch, or organization has been a lifelong struggle. Think long and hard about where your personal entrepreneurial hurdles lie. Make a list. And use that list to inform the next question.

Who do you need on your team?

 Photo by Chris Creed

Photo by Chris Creed

You have a sense of what you have locked down, and where you’re going to falter. So what can you do to shore up those holes? When you’re just starting a business, hiring people to fulfill those needs can be a little tricky, financially, so can you get creative with your thinking? Do you have an uncle who’s a CPA who might be willing to help you get started? Do you have some supportive and social media-savvy friends who are game to help you spread the word? Do you already have some happy early customers willing to share feedback about your work or your products?

As your business builds, you’ll eventually need to hire an accounting firm, a bookkeeper, maybe an office manager or a designer and PR rep. But in the meantime, think about your team broadly: You’ve distilled your own strengths; who around you has strengths they might be willing to put toward the cause as a favor or at a friends-and-family rate?

Are there mentors in your midst?

As a budding entrepreneur, there are few more valuable things than the guidance/advice of someone who’s been in your place, and moved on to where you’re trying to go. Is there a local entrepreneur you really admire? Ask if you can shadow. If shadowing isn’t an option, see if they might be willing to let you buy them a coffee and pick their brain. You might be surprised by how willing established entrepreneurs are to share experiences — they know what you’re up against, financially, physically and emotionally, and that tends to breed a ton of empathy and generosity. 

If you don’t have a specific mentor in mind, keep an eye on our Office Hours sessions — we invite entrepreneurs and independent professionals into our space weekly to share their experiences and advice. And if you’d like to dig deeper than that, our CO.STARTERS program is built on interaction with a variety of local entrepreneurs/potential mentors, and our grads also have access to a nationwide network of other CO.STARTERS alumni who know exactly what you’re working through and what it takes to move past those first entrepreneurial steps.

While you’re thinking about these questions, a little reading we recommend to help fire you up, too:

Got some ideas of your own? Share your thoughts in the comments, or holler at us on Twitter (@theskillery). Next week, we’ll look at getting to know your ideal customers.