August 2025
Mid-year reflection and check-in for business owners
The middle of the year is such a powerful moment to pause and reconnect to the bigger picture that can be pretty blurred by day-to-day demands.
It is so easy for business owners to get caught in the momentum, the hustle-and-grind, the doing of all the things.
And, I mean, usually it’s a good thing.
Most of us would go out of business pretty quickly if we didn’t know how to ride those big waves when they come to us, right?
But sometimes momentum makes you blind.
You can’t really tell whether what you’re doing is still aligned with your goals, energy, or purpose when you’re in the thick of it.
That’s why I love a solid mid-year reflection and check-in.
The middle of the year is such a powerful moment to pause and reconnect to the bigger picture that can be pretty blurred by day-to-day demands.
While I still love a year-end reflection moment, I always see the mid-year reflection as a chance to realign my focus, shed tasks or strategies that no longer serve me, and make intentional decisions about where to go next.
I think for creatives especially, this kind of reflection helps reignite your spark, and bring renewed energy, fresh ideas, and a deeper sense of purpose into the second half of the year.
This kind of reflection helps reignite your spark, and bring renewed energy, fresh ideas, and a deeper sense of purpose into the second half of the year.
How to do an effective mid-year reflection and check in
This doesn’t have to be complicated at all.
As long as you’ve committed to being honest with yourself, all you need now is some quiet time to grab your journal or a fresh Google Doc, and work through my favorite prompts.
Feel free to swap out any/all of these for whatever prompts you prefer. You can go through them in one sitting or take your time across a few days.
Let it be a conversation with yourself, not a performance for anyone else. There are no right or wrong answers and no one is grading your work!
1. Take a temperature check
Start by rating how you’re feeling (on a scale of 1 to 10) in these key areas of your business:
- Marketing + Visibility
- Work-Life Balance
- Personal Growth
- Creative Energy
- Client Projects
- Finances
The idea is that this will be a quick gut check on where things are working and where you may need to devote a little attention.
You don’t need to fix anything at this point, just notice what’s asking for your attention to set the stage for the rest of your reflection.
2. Check in on your lessons
The past six months have likely taught you something about your rhythms, your needs, or your strengths. (Or maybe all three. We’ve all had those kinds of years, haven’t we?)
Reflect on one core lesson you’ve learned about yourself as a business owner or creative.
Here are some of my examples from over the years:
- 1. I do my best work when I give myself more creative space. Rushing kills inspiration!
- 2. I don’t want to scale a big agency because I thrive in deep, intimate client relationships.
- 3. I’m more strategic than I give myself credit for. Clients trust me not just for my brand insights as much as for my design techniques.
3. Celebrate your wins
As a business owner, I bet you’re really good at beating yourself up for the missed opportunity and missteps along the way.
But when is the last time you appreciated – let alone celebrated – your wins?
That’s what I thought 😉
Look back and list a few things you’re genuinely proud of from the first half of the year. (And obviously, these could be external achievements or internal shifts.)
Here are some of my examples:
- 1. Fully booked my design calendar for Q1 and Q2
- 2. Launched a new website for a dream client (and they saw a 2x increase in inquiries!)
- 3. Raised my prices and had zero resistance
Remember when I said you didn’t have to do anything about your temperature check?
Well, you have to do something about these wins.
Go celebrate them!
You earned it and you’ll be more likely to reach successful milestones in the future when you celebrate those from your past.
4. List the endings you’re grateful for
Growth isn’t just about what you’re doing, it’s also about what you’ve let go of. (It’s okay if you really had to fight yourself to let go of them, the point is that you did it, right?)
So what are you relieved to be done with?
Here are some of my examples (I am beyond grateful I’ve let go of my tendencies to):
- 1. Take on low-budget projects out of fear of slow months
- 2. Over-customize everything (I’ve embraced more streamlined, strategic systems)
- 3. People-please in discovery calls (I’m more confident saying “this isn’t a fit” now)
These endings tell you as much about how far you’ve come as your wins do, so make sure you celebrate them, too!
5. Give yourself mid-year advice
If you could go back to January and whisper something to your past self, what would it be?
This is your chance to distill what you’ve learned into something actionable or encouraging.
Here are some of my examples:
- “Trust that the right clients will come if you show up as your full self.”
- 2. “Don’t be afraid to simplify. Everything doesn’t have to be bespoke to be valuable.”
- 3. “Let your brand evolve publicly. You don’t need to hide until it’s perfect.”
You’re wiser now so let that wisdom shape how you move forward.
6. Track what energized you
What gave you life over the past six months?
What were the things that lit you up on the inside and made you think, “If I could just do THIS forever, I’d be in heaven”?
These are the things you want more of in your business moving forward.
Here are some of my examples:
- 1. Working on visual identities outside of my usual aesthetic
- 2. Co-working days with fellow creatives (even virtually)
- 3. Designing my own newsletter and turning it into a creative outlet
Your joy is a compass. Never be afraid to let it guide you.
7. Be honest about what drained you
Remember those things you let go of? I’d bet anything those were energy drainers, and you and I both know you’ve got more of them just waiting to jump up and bite you in the backside.
So ask yourself now: What left you feeling depleted, scattered, or uninspired?
These are the areas that may need restructuring or new boundaries.
Here are some of my examples:
- 1. Back-to-back launch timelines with no buffer in between
- 2. Endless revision rounds with unclear feedback
- 3. Trying to do all the content marketing (Threads, Instagram, email, blog)
What can you shift or release in the second half of the year that will give you energy and/or time back?
8. Practice gratitude
Take a moment to name what you’re thankful for in your business life. Gratitude can be a wonderful tool to ground you and remind you how far you’ve come.
Here are some of my examples:
- 1. Referrals from past clients who believed in my work
- 2. Quiet mornings to work on my own creative projects
- 3. Creative clarity. I’m finally feeling aligned with my niche
You don’t have to have a gratitude journal or anything fancy to say thank you for the little (or big) moments that make everything else worth it.
9. Dream about the future
What would you love to add to your work life in the coming months?
These things can be creative, strategic, or even personal.
Here are some of my examples:
- 1. A slower, seasonal launch model with real downtime
- 2. More passive income through templates or educational content
- 3. One or two creative collaborations with other designers or photographers
Just let these be the seeds of possibility, okay? Once again you don’t have to do anything about these if you’re not ready.
We’re not trying to add more pressure or expectations to your life.
A judgment-free way to pause, breathe, and listen to yourself with curiosity instead of criticism.
Look back to move forward
I hope you see this mid-year reflection as what it’s meant to be: A judgment-free way to pause, breathe, and listen to yourself with curiosity instead of criticism.
Whether the first half of your year felt expansive or messy (or both), this is your invitation to honor what’s true, celebrate what’s working, and gently shift what’s not.
I’m a firm believer that growth starts with awareness and clarity comes from looking inward before rushing forward.
And the beauty of being a small business owner, isn’t it?
Especially if you’re a creative or in service-based work – you have the power to evolve your business in a way that supports you.
So take what you’ve learned, hold it with care, and step into the next season of your business with intention, energy, and self-trust.
You’ve already grown more than you think and the best part is that you get to decide what comes next.