When I packed for my 40-hour offsite quarterly planning retreat, I brought a full stack of journal prompts to help me process the past 90 days and plan the next. Some were exactly what I needed. Others? Yeah those weren’t helpful at all.
I don’t believe in journaling just for the sake of it. If you know me at all, you know I believe in high-impact activities that actually accomplish something in our small businesses! So I use prompts that lead to real strategy, clarity, and decisions. Not navel-gazing.
In this post, I’m sharing a few journal prompts that helped me do exactly that, plus a few I’ll skip when I take my next quarterly planning retreat.
Most of the prompts I used are reserved exclusively for my membership girls, but I’m giving you a peek here to help you make your next planning day more powerful.
Prompts That Helped Me Think Clearly
These were simple but effective for my quarterly planning retreat. They helped me reflect on the right things, focus on what was working in my business, and see where changes needed to happen. As a busy entrepreneur, clarity is one of the best gifts. So here’s what worked:
1. What are three things that went really well last quarter?
Start with the wins. This one helped me focus on what worked before diving into what needed fixing. I have a tendency to over-focus on what needs to be changed in my small business and this was honestly a really great prompt to start the weekend with. I realized quickly that 3 wasn’t even enough! There were so many good things that happened, so many blessings from God in Q1 of 2025.
2. What felt harder than it should have?
This question helped me spot misalignment in my business. Usually this reveals a missing system or something I shouldn’t be doing at all. I am in a season of growth and need to delegate more. I was able to see, with this prompt, that I am maxed out in certain areas, as is my VA. So this led to some helpful mapping on what the next step needs to be when it comes to the team and who we hire next..
3. What is one BOLD thing I’m going to do this quarter in my business?
This one challenged me to stop playing it safe. Those who follow me on Instagram know that I am all about shooting your shot in business – to just go BIG and see what happens.
But I was fresh on the heels of recovering from a major surgery and I’d been in a safe cocoon in the business as I reacclimated to working more hours and gaining back my strength and energy. That said, this prompt reminded me that some of the biggest successes with Walk Like Warriors this past year were because I did something BOLD. I was thankful for this prompt because, as female entrepreneurs, we need to get out of our comfort zones and make big moves sometimes. Even if it doesn’t pan out.
So I left the retreat with one decision I would not have made otherwise. I’m all about taking (calculated) risks in business and I realized because we’re scaling, it’s really easy to be in the “just trying to stay caught up” mode instead of the “go out and do BIG, BRAVE things” mode.
With this prompt: I set one goal and am running hard after this big, scary thing this quarter.
Prompts I Loved
These were my favorites. I’ll use them every quarter moving forward.
4. What was the biggest lesson I learned last quarter? The biggest takeaway I want to remember?
This helped me see the bigger picture and gave me a sense of reflection before jumping into the next season in my business. After all, what are the painful lessons for if not to learn, change, and also to REMEMBER the lesson? What a gift. Because I want to be able to look back over these quarterly “big lessons” during future offsite quarterly planning retreats in my small business.
5. What’s working right now that I need to double down on?
This led directly into strategy. I used it to figure out where to put more energy and money in the upcoming three months.
Can I give you some coaching real quick? This is where A LOT of entrepreneurs – but most especially female entrepreneurs – get into trouble. They chase new, new, new when they really need to figure out what’s working and do more of that one thing.
After coaching hundreds of women in the last 15 months, I can say this: chasing shiny objects kills more small businesses than a lack of sales did over the past year. It feels good in the moment, but it takes our eyes off the ball.
Want to be successful? DRILL DOWN into what’s already working. Taking some time with this journal prompt will help you run your small business more effectively.
6. What do I feel most energized to deliver?
This helped me get additional clarity on what I’m selling and what I’m doing. When I was recovering from a major medical episode in the fall of 2024, I came to the realization that while 1:1 business coaching was bringing in the lion’s share of revenue, it was the thing I liked the least.
Now, sweet one reading this blog, it’s easy to read this and skim on past. But I need you to know this:
It was hard – reallyyyyyy hard – to come to that realization. Because the women? I LOVED THEM. And the revenue? It was the MAJORITY of the money that came in that year.
But the ongoing coaching was just not an area that I felt I was the best at. And it was slowly draining me.
What I LOVE to do is teach live to groups, coach inside The Success Squad, coach my membership girls, and jump on one-time strategy calls (90 minute calls where a business owner can come to me with any problem no matter how big and we solve it in 90 minutes.)
There was nothing I wanted more than to end 1:1 coaching back then. So I did. It was scary because SO much of my revenue was coming from that. I mean, it was honestly a very scary decision.
But in figuring out what I am energized to offer, it changed everything.
When I coach female business owners, I tell them this: If there is something you are selling/offering that absolutely drains you or fills you with dread, stop doing it. Over the course of months or years, it will be the reason you quit your business.
So this quarterly retreat, I realized teaching live is my favorite thing in the world. I do that inside The Success Squad and in my monthly membership and that’s pretty much it.
So I want to lean into those even more and lean out of what is not bringing that same energy to my life.
Prompts I Didn’t Love
These weren’t bad questions. They just didn’t help me get where I wanted to go during this retreat.
7. What do I need to surrender?
This felt too abstract for a strategy-focused retreat. It pulled me into mindset work when I needed traction and decisions. And I couldn’t come up with anything that needed to be surrendered.
8. Where am I holding back or living in fear?
This one felt like a rabbit hole. It didn’t lead to clarity. This is one that might be helpful to some people but I am not someone who worries or lives in fear. I’m actually pretty brave and not averse to tasks.
So, when I read this prompt, I just sat there staring at my notebook, unsure of what to write. I probably wasted 20 minutes trying to think about this before I just ditched it. What a waste of time this one was. I shouldn’t have allowed myself to be stuck for so long.
How to Tailor Your Prompts to Your Business Season
Not every prompt fits every quarter. If you’re hiring or scaling, focus on team, leadership, and systems. If you’re launching or restructuring, ask what felt chaotic and what could be simplified.
Choose prompts that get you unstuck and into motion. I don’t believe mindset prompts and introspection work is particularly helpful for most business owners trying to take strategic action and set big goals for a quarter.
If a question leads you to spiral or shut down, skip it.
If you get stuck for more than a couple of minutes, ditch it.
Want a list of journal prompts to use at your next quarterly planning retreat for your small business? Click here to get your hands on it!
In Case You Missed It:
- Read Blog 1: Why I Took a 40-Hour Quarterly Planning Retreat and How I Structured It
- Read Blog 2: What I Packed for My Solo Quarterly Planning Retreat (with a free list of my favorite items you need for your next quarterly planning retreat!)
Coming Up Next:
In the next post, I’ll share what worked beautifully during the retreat and what I’ll absolutely do differently next time.
Click here to read Blog 4: What I Loved and What I’ll Do Differently Next Time
