Small Business Tips: 5 Questions to Ask Yourself to Build a Business That Fits You

women's leadership coach

When I first started my business, I wanted a template: a guide, a set of rules that, if followed, would guarantee success.

Basically, I was insecure, so I desperately wanted someone to tell me what to do because I believed that external advice would insulate me from failure.

Fast forward. Now, I know that as powerful as a business model can be, the real magic happens when you base your business on your biggest asset: you!

For a long time, I felt ashamed or embarrassed if my business looked and felt different from others in my industry, especially if they were “above” me. All the comparison-itis left me feeling drained, burned out, and wondering why I started the business in the first place.

If you’ve ever felt exhausted, overwhelmed, or lost in your business, it’s probably not because you’re doing it wrong. It’s probably because you’re doing it like an employee, not a boss. For so many entrepreneurs, the entire point of working for yourself is the ability to do things your way, to enjoy creative freedom, and finally be in charge of your day, but we get swept up wanting to “get it right” or fit in.

Why is that so many entrepreneurs struggle to do things their way?

I think it comes down to mindset: specifically the employee mindset versus the entrepreneur mindset.


In an employee mindset, you follow the rules, wait for the higher ups to hand you instructions, and largely let others control the direction of your goals (comparison shame, anyone?). In an entrepreneur mindset, you don’t follow the rules—you make the rules. And that can be scary. Because most entrepreneurs start as employees, sometimes we accidentally carry the employee mentality with us into our businesses.

When it comes to making rules in your business, alignment is key. Even if you have a traditional career, making sure it’s closely aligned with your “big picture” vision for your life is essential to feeling good about your day-to-day. So how do you get this alignment?  

Here are 5 questions to ask yourself so you can build a business that authentically fits you.


#1: Why am I doing this whole business thing in the first place?

This is probably the most important question to ask yourself before starting a business, pivoting into a new direction, doing an alignment checkup, or even figuring out where to focus your efforts: What’s the point? What are you attempting to accomplish with this this whole business thing? Are you looking to support yourself, to make extra income for your family, to feel fulfilled, to make a difference, to bring about world peace? Do you see an unmet need in the marketplace or a problem that can only be solved by your product? There’s no wrong answer here. The point is to get clear on the immediate goals of your business, your long term vision, and the point of all your hard work. 

For example, my lofty business vision is raise the consciousness of humanity through the rebalancing of masculine and feminine energy on the planet. Helping creative ladies start feminist businesses that make the world a better place is simply my vehicle. The immediate goals of my business is simply to support myself and my family with something I enjoy and am good at.

Again, there’s no right answer. The only right answer is the one that works for your life. What’s your business raison d’être?

#2: How big do you want your business to be?

Now that you know why your business exists, let’s start fleshing out the parameters of the perfect business for you. For example, if you escaped a miserable corporate behemoth to start and nourish a small business, the last thing you want to do is build the same type of company you hated. 

Marie Forleo, a business mentor of mine, defines three different business sizes: micro business, small business, and big ass business. 

She defines a micro business as, “ a one woman show or freelancer with an assistant, though it’s basically a business with 5 or fewer people.”

A small business has “less than 100 employees and less than $50 million in revenue” and a big ass business is basically what it sounds like. Think Apple or Whole Foods.  

So when it comes to the size of your business, what feels right, and what’s the amount of work you’re willing to put in? Do you want to be managing a team? Working with a board of investors? Alone with your laptop in a coffee shop? When you think about the differences between a micro biz, a small biz, and a big ass biz, which one fills you with excitement and energy? Which feels totally overwhelming?

#3: What do you want your typical day to look like?

Entrepreneurial overwhelm is a very real thing, and most of the burnout I see in clients is not because running a business is so hard-it’s because they are setting up their days in ways that leave them frazzled, exhausted, and empty. While you may have certain tasks that need to be done at a particular time, a good bit of how you structure time and productivity for you and your team is dependent on, well, you! So think about how you most naturally spend your time and energy, and ask yourself: What does my ideal work day look like?

Do you want to be able to roll out of bed at 10 and work on whatever inspires you at your own pace, or do you want clearly defined time blocks dedicated to each task? What time of day are you at your best? What time-bound responsibilities do you have on a daily or weekly basis, like getting the kids to school or taking Grandma to the doctor? If you had all the time and support in the world, how would you structure your day?


#4: What season of life are you in?

In different seasons of life, we have different responsibilities, access to resources, and levels of time and energy at our disposal. For example, a married homeowner with 3 children has a very different set of responsibilities than a 22 year-old recent grad who’s footloose and fancy free. Neither one is likely to be more successful than the other, but if they try to go about building their businesses the same exact way, one or both of them is going to struggle. The mom of 3 may be super short on time, but flush on cash from saving for years; whereas the recent grad may be scraping by financially, but has time to waste.

The point here is to understand and make peace with the season of life you are in, rather than resenting that day job that pays for your kids’ health insurance or feeling lost and overwhelmed because your journey is slower than someone else’s. Trust that the season of life you are in is perfect for your growth as a human being, and trust that successful businesses can be built in any life season. Basically, own it. Don’t waste energy resisting it. 

What season of life are you in? What does this unique season give you access to? What supports do you need to put in place for this season’s challenges?

#5: What business model best fits your products and services?

A business model is basically a proven strategy for how your business makes money, like selling products, services, memberships, etc. While you are certainly welcome to make up your own creative business model from scratch, it is way quicker and easier to get started with an already-proven business model and then customize as you go. Instead of reinventing the wheel, let’s use one of the models that other people have pioneered.

First, let’s start with what’s out there: When you think about the leaders in your industry, which business models come to mind? Which business models seem to dominate your field?

Next, let’s personalize. Of the models that exist, which are easiest to utilize for your specific products or services? Which feel confusing or arduous? Which business models feel exciting to explore? Which do you need more research on?


In a nutshell: your business, your rules.

And the beautiful part is that your business doesn’t have to look like any one else’s. The goal is simply to be so in love with your decisions that it doesn’t matter if anyone else is. So which of these questions do you need to focus on to come more into alignment with a business that’s all about you? Leave a comment below to let the community know.


And don’t forget to download the free creative business plan workbook and template below to jumpstart your biz journey!


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startup coaching for women
startup coaching for women
startup coaching for women
startup coaching for women