I don’t know about you, but summer always makes me want to reorganize everything. Maybe it’s the longer days or the fact that my kids are out of school disrupting my usual routine, but something about this time of year screams “figure your stuff out.”

And honestly? Your business could probably use some of that same energy. I’ve been doing midyear check-ins with clients for years now, and there’s something magical about summer timing—you’re either finally getting a breather to think big picture, or you’re knee-deep in chaos and need to make sure your systems can handle it.

I’ve been talking about midyear business reviews for years through my “What We’d Be Working on If I Were Your COO” series, and the themes remain consistent because they work. This isn’t about making knee-jerk changes or pivoting just because you’re not perfectly on track. Instead, it’s about taking an honest, comprehensive look at where you are and making thoughtful adjustments that will support your long-term success.

Here are the 10 essential areas every creative business owner should evaluate at midyear to ensure their business remains sustainable, profitable, and aligned with their bigger vision.

Your Foundation: Vision, Goals, Capacity & Calendar

Before diving into numbers and systems, you need to check in with your foundation. Think of these as your business temperature check.

1. Your Vision

Your vision is the big picture of what you want your business and life to look like—the impact you want to make, the lifestyle you want to create, the legacy you want to build. Is your vision still up to date? Does it need to be adapted in any way? Your vision should remain aligned with both your business goals and your life goals. Life changes, we grow, we see new opportunities, and sometimes our vision needs to evolve with us.

2. Your Goals

This doesn’t mean changing your goals because you’re not on track (I actually highly discourage that), but circumstances do change. Goals are different from vision: they’re the specific, measurable outcomes you’re working toward. Your goals are the stepping stones to your vision. They guide the way and keep you on the right track as you work towards that big vision. While your vision might shift as you grow personally, your goals should be evaluated based on whether they still make strategic sense. Are they still the right milestones to get you where you want to go? Have new opportunities emerged that require different targets?

3. Your Capacity

We’re moving through summer, and many people’s capacity is shifting. Are you clear on what your new capacity looks like? Is it more or less than before?  Are you traveling more and need to batch work in larger chunks? Are your kids off school, and now you’re juggling work and the kids (and all their snack requests) during your normal office hours? Are the longer days opening up more space for you, and you’re pouring more time and energy into your business in this season? Understanding your true capacity prevents over-commitment and burnout.

4. Your Calendar

This one I’m especially highlighting because it’s what I’ve been working on myself: pruning a calendar that had become bogged down with over-commitments. As the saying goes, “show me your calendar, and you’re showing me your priorities.” Look at your calendar honestly and with fresh eyes. Is it what you want it to be? Are the events that are taking up space reflective of and aligned with your vision, goals, and current capacity? If not, that’s often a major red flag that something needs to shift around how you’re spending your time and energy. 

The Alignment Check

After evaluating each of these individually, here’s the crucial step: check how they align with your definition of success. While these four foundational elements offer direction and guidance, your definition of success is the ultimate measuring stick, your North Star. It’s what determines whether you’re truly on or off track as you pursue your own version of success. 

Your definition of success tends to be more evergreen and long-term (it’s NOT something that should be overhauled multiple times per year), but it’s worth reviewing, especially if you’ve experienced any major life changes. Everything else should flow from and align with this core definition.

Your Numbers: Finances and Offers

Once you know where you’re headed personally and professionally, it’s time to dive into the nitty-gritty numbers that drive your business.

5. Your Finances

Get really comfortable with where you’re at financially. Know your KPIs, your revenue numbers, your sales numbers. Are you hitting your “Enough Point,” that baseline number you need to cover your expenses and feel financially secure? If you’re not covering your Enough Point, you need to make changes sooner rather than later.

6. Your Offers

I encourage my coaching clients to evaluate their offers at least twice a year. Ideally this happens at year-end/beginning and at midyear. Don’t sit on offers that aren’t performing too long. Look at what is and isn’t working right now, what is and isn’t feeling good to fulfill, and whether your price points are where they need to be.

The Progress Check

Evaluate both your finances and your offers against the progress you’ve made since the beginning of the year. Are you on track to hit your goals? Most importantly, are you covering your Enough Point? We’re in this for both sustainability and profitability!

Your Operations: Systems and Software

Now that you know how your business is doing, let’s look at how it’s running.

7. Your Systems

Take a look at your business systems (think: sales, marketing, and operations). Are they still supportive of where you’re at? Are they working with each other? Pay special attention to your software. Integrations break, new features are added, systems evolve. Is everything still working the way it should? Now’s the time for a tune-up.

Your People: Client Experience

With your business running like a well-oiled machine, it’s time to focus on the people you serve.

8. Client Experience

Do a deep dive here. Look at all the feedback forms from clients you’ve worked with this year. Get a temperature check on how people are feeling about your business. Examine your client retention rates. Are they where you want them to be? Think about conversations you’ve been having with current and past clients lately. What are they asking for? Are you still meeting their needs, or are they outgrowing you and moving on? 

Are the clients coming in your ideal clients? Are you delivering solutions to their problems and making their lives better? Do they want what you’re selling? Are they sending referrals your way?

Consider both client satisfaction and the client experience itself. Are your clients feeling appreciated, supported, and acknowledged throughout their journey with you?

Creative Inspiration and Development

Finally, with your business on track and running smoothly, check back in with yourself.

9. Creative Inspiration

Are you feeling creatively fulfilled? Are you keeping up with your creative rhythms? Are you continuing to innovate and grow as a creative? This is about keeping that spark alive that drew you to your work in the first place.

10. Personal and Professional Development

Are you continuing to grow as a business owner and as a human being? Are you still excited about things? If not, what can you do to encourage continued growth or get inspired again?

Being aware of early signs of burnout (whether creative, professional, or personal) and actively working on continued development, excitement, and growth, will help ensure the longevity of your business.

Making It Actionable

This midyear should not overwhelm you with changes. Instead, it gets to be an opportunity to objectively assess where you are so you can make strategic adjustments that support your long-term success.

As you move into summer, consider whether this is a slower season that allows for working on your business instead of just in it. Or maybe it’s a busier season, and you need to ensure your business is set up to run smoothly while you’re focused elsewhere.

The beauty of this midyear check-in is that it’s not about perfection, it’s about progress and alignment. Your business should serve your life, not the other way around. By regularly checking in with these 10 areas, you make sure that your business remains sustainable, profitable, and fulfilling for years to come.

Take some time this summer to look at your business with fresh eyes. You might be surprised by what you discover and excited by the adjustments that will move you forward.

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This midyear evaluation builds on concepts I’ve been sharing for years in my “What We’d Be Working on If I Were Your COO” series. For deeper dives into any of these topics, you can explore the full series here, including the original post and quarterly editions that cover the entire business year.