The 5 Questions Every Creativepreneur Should Be Asking Themselves

If I had a room full of creativepreneurs and asked them to raise their hands if they’ve ever felt insecure or question the value of their work, how many hands do you think would shoot up in the air? I’m thinking quite a few! I feel like self-doubt emerges so easily and so quickly when you’re trying to create a business that allows you to pay your bills while also fulfilling what you’re passionate about. Doubt enters our minds without permission and it pops up when we least expect it.


Small business ownership is a whirlwind of excitement and nerves, victories and hard-learned lessons, pushing ourselves and finding ways to grow. Think what would happen if we could retrain our minds to only focus on asking ourselves questions that will work toward building our businesses up rather than tearing our confidence and self-worth down? I think pretty awesome stuff could happen.

Instead of spending our time asking questions like, “Am I good enough to run a successful business?” “Why am I not booking more clients?” “She has so many engaged followers, why can’t I be more like her?”, let’s focus on asking ourselves questions that garner actionable answers that will help us build our businesses. Here are the five questions you really need to be asking yourself to help get focused on getting your business on the right path. The most important questions you should be asking yourself are actually super simple. (Simple is always best!) But don’t let these basic questions fool you. They’re going to help you hone in on the ways you can be growing your business. The key is working from general to specific, so let’s get started!


“Knowing Your Why” is a topic you’ll see floating around on a lot of blogs speaking to creative entrepreneurs and bloggers, and for good reason! It’s an important question to ask yourself, and it can apply to every phase of your business, from planning to launching products to growing your business or blog. Asking yourself “why” while planning and building your business behind-the-scenes starts you off on the right foot and gives you a strong vision for the future. When you know your why, it’ll help you determine your mission and vision, and it will act as the thermostat for your business. It should control the purpose behind every action you take and things you create, just as a thermostat controls the temperature of a house.


You know you’re why, but now you need to know your audience, which may be influenced by the mission and vision of your business. Think of your business or blog’s purpose, who is an ideal client who would be drawn to the work and content you’re producing? I’ll use myself as an example. I’m a graphic designer, and the “why” of my business is to create hand-crafted and heartfelt design for small business owners. The content I write on this blog is geared toward other creativepreneurs who need some insight about design, running a business, or who may just need some inspiration. All the work I do and the content I create points back to who my ideal client is: a small business owner (ideally creativepreneurs), who values design. 

So, who is your target audience? Your dreamiest of dream clients? Get as specific as possible. Are they male or female? What’s their lifestyle? What stage of life are they in? What’s their niche? What sort of challenges do they face daily? If you want, you can even create a persona or avatar of your ideal client.


I like to think that the answer to “what” is the combination of the questions “why” and “who”. When you know the purpose—the why—of your business and who you’re trying to reach, then you can more accurately determine what services or products (or both!) will help accomplish that purpose and reach that audience. Everything works together in a way that makes sense, and helps give you clarity.

So when you’re thinking of creating a new product, writing a blog post, or launching a new product, measure it up against these two questions:

  1. Does is line up with my business’s purpose?

  2. Would your ideal client find it valuable and be willing to make the investment?

Tips + Ideas + Suggestions:

  • Niche-specific services*

  • E-book

  • Webinars

  • Printables

  • E-courses

  • Video tutorials

  • Content upgrades

  • Informative blog posts

  • Resource lists

  • How-to guides

*In order to properly marry you’re "why" and "who" to make you’re "what", you need to get quite specific. Don’t just say you’re a business coach. Say you’re a business coach for creative mompreneurs. You have a specific audience, so it’s in your best interest to offer a specific service in order to effectively reach them and establish yourself as an expert.


Now that you know your purpose, your people, and your offerings/services, you just need to find where they’re hanging out! With so many social media platforms available, it’s easy to spread yourself too thin. Narrow down the platforms you’re using to the ones that you most enjoy, complements your content best, and makes it easy to engage with your ideal audience.

Tips + Ideas + Suggestions:


  • Find people in your niche, and get social! Comment (and be genuine!) to engage with people in your community and build relationships.

  • Find hashtags that are popular (aka a lot of people looking through those photos) and fit in with your niche

  • Participate in Instagram photo challenges. They’re fun and will connect you with a new group of people


  • Share more than just your content and what you’re selling. Share resources that you feel are genuinely helpful, entertaining, or interesting for your ideal audience.

  • Participate in Twitter chats. You’ll connect with people and be able to share your opinions and expertise on topics that are within your area of interest.


  • Join business groups that aren’t all about promotion. This opens up ample opportunities to network, find jobs, share helpful resources, and show your knowledge when people ask for help.

  • Since there’s not a limited word count like there is on Twitter, you can share longer stories and posts with your audience. Ask for people’s opinions and feedback to encourage engagement.


  • Join group boards to share your content with a much broader audience

  • Only pin high-quality images that link to reliable sites

  • Create secret boards for the types of pins your ideal audience wouldn’t be interested in

  • Make sure your site allows for rich pins


After answering all those questions, now all that’s left is to figure out how you’re going to attract your dream clients, tell them about your business, and then get them to purchase your products or services. No big deal, right? It sounds like it could be overwhelming, but it’s totally do-able! Remember, this process is all about working from general to specific. The “how” is where it gets super specific and these questions get actionable answers. Here’s some ways to make “how” happen:

Consistent branding

Consistency is the key to unlocking the “how” door. Be consistent in everything you do from the tone you write in, to the quality of content you share, to the design of your blog post graphics. Your branding should be present in everything you do involving your business. You want to leave your mark on things around the web so that people immediately recognize it as yours. Brand recognition is a beautiful thing! Trust me, you want it. Consistency in your branding will help keep things in line with your purpose and with the audience you’re reaching. Plus it'll help you create the best products and services, and keep people following along with what you’re doing.

Social butterfly

Like I addressed in the “where” section above, find your favorite and most successful social media platforms. Share high-quality content and engage with your ideal clients and others in your community. Building relationships is a great way to build a following and eventually bring in sales. People are more willing to purchase things from someone they like and trust.

Drop some knowledge bombs

If you want people to read your content and trust your expertise, then give them something that will benefit them, whether it’s teaching them how to do something, encouraging them, or entertaining them. Don’t keep all your hard-learned lessons for yourself. Give most of that knowledge away for free, and then build products and services using that knowledge and experience.

Make it easy for people to figure out what you do and how they can hire you

I’m stunned by how many websites I’ve visited and end up leaving not feeling 100% confident that I know what that person does. THAT’S NOT GOOD! Sorry for the all caps, but it’s absolutely crucial that people know what you do. It should clearly state it on your website and on your social media channels. And then the content you share on your blog and on social media channels should help show what field you work in and what you're knowledgeable about.

You also need to make it clear what services you offer, and have a clearly marked way for people to get in touch with you. Don't hide your contact page; keep in a visible and predictable place. If you make things too difficult, people may decide it's not worth the effort to try and get in touch with you.

While all of these questions and their answers work together to help you shift your focus to forming a plan and a guide for your business, they can also be used to get to the heart of other problems.

If you're feeling insecure in your success, ask yourself why that is. Is it because you're following someone on Instagram who seems to have the perfect life and the perfect business? If so, unfollow them and realize that you shouldn't compare your journey to someone else's. Are you feeling frustrated because your website's traffic and engagement is low? Ask yourself "why" to get to the heart of the matter. You'll soon find out what you should change, who you really need to be targeting and how to make it all happen. 

When your mind isn't in the best place, sometimes it takes going back to the basics and asking the most simple and significant questions. These questions put you in a positive and proactive mindset, unlike those other icky questions that make you doubt yourself.

If you’re feeling stuck on something, go back to the basics of why, who, what, where, and how. They’ll get you back on track to building your business and realizing that you're doing just fine.

This infographic sums up the 5 most important questions to ask yourself as a business owner. Go ahead and pin it to save it for later!