Journal Prompts for Small Business Owners Looking to Reflect this Autumn
There’s just something about autumn that makes reflection feel natural – the slowing down, the softer light, the urge to start fresh (and the perfect excuse for a new notebook). We know that being a small business owner is much more than simply doing the work. It’s not just about what you do, it’s also about who you’re becoming as you do it. That’s why every Monday morning at Wild, we host Jump Start – a journalling session to reconnect with ourselves as the humans behind our businesses.
Below you’ll find 20 prompts to guide your own reflections this season. You could start from the top and work your way down the list one at time, or you might choose one that you feel called to explore in the moment. Just remember to set some time aside, grab a big drink…and if this inspires you to buy up a new notebook, we promise we won’t tell anyone.
20 Reflective Journal Prompts
What kind of growth feels good to me this season?
What would a successful week look and feel like for me? Not just in outcomes, but in how I show up and move through my days?
How can I welcome inspiration, support, and opportunities while also giving myself space to rest and recharge?
What would it look like for me to move through the next few days with both focus and gentleness? Which priorities truly matter, and what can I release to create more ease?
How can I honour that rhythm in my business while still moving forward with clarity?
If I treat this week as a fresh start, what do I want to carry forward and what can I gently leave behind?
Where in my business or life have I held back, shrunk, or apologised for taking up space? What would it look like, and feel like, to step fully into those moments with confidence, trust, and self-belief instead?
What would a successful week look and feel like for me, not by anyone else’s standards, but by my own?
What feels exciting or hopeful about the week ahead, no matter how small? How can I bring more of that energy into the way I approach my work?
If I only had energy for one or two things this week, what would I want to move forward most?
What do I know, without a doubt, about my own strengths as a business owner?
How does my business reflect the truest parts of me, and how can I lean into that more this week?
When have I come through quiet or uncertain times in the past? And what helped me stay grounded?
Where in my body or business am I holding tension that’s not mine to carry? What could I let go of or ask for help with?
What parts of my business still feel aligned and exciting? And what feels like it’s ready to shift or soften?
What do I want more of, not just in work, but in my day-to-day life?
What have I already built that proves I'm capable?
What would it look like to lead myself through this week with calm and trust, instead of urgency or fear?
Name one small, joy-filled action you can take into this week that aligns with your bigger vision (or you can just focus on the joyful thing if the bigger vision feels too much).
How might my business shift if I allowed myself to belong, without question, in every room I enter?
Keep an eye on our Instagram for more thoughts on running an aligned business and to connect with our brilliant community of likeminded business-owners. Wild members, don’t forget you can join us every Monday morning for our journalling in Jump Start – link is in your dashboard.