Ready to Grow? Ask Yourself These Hard Questions Before You Plan 2026

By December, most founders aren’t planning… they’re unravelling.

The adrenaline that carried you through the final quarter starts to fade. Your mind is crowded with board packs, client commitments, team emotions, family logistics, and the low hum of “I should really plan next year…”

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But this is exactly the moment when the truth has the best chance of breaking through.

Not through a five-hour goal-setting sprint.

Not through a colour-coded annual review.

But through a few sharp, honest questions that cut through the noise and show you what’s really going on - in your business and in your leadership.

This is your pause.

Your exhale.

Your reset before you race into 2026.

🧘‍♀️ How to Approach This (Gently)

You don’t need clarity.
You don’t need the perfect notebook.
You don’t even need to “feel ready.”

You just need an hour, and a little bit of honesty.

Here are three ways founders tell me this reflection actually works:

1. The Hour Alone

Take yourself somewhere quiet - a café, a corner, a train seat.
Pick a handful of questions from each list and write freely.
No editing. No polishing.

2. The Voice-Note Walk

Put the questions in your notes app. Take a long walk.
Talk out your answers as they come.
Let movement become momentum.

3. The Founder-to-Founder Debrief

Choose someone who gets it.
Swap questions.
No advice - just truth.

Simple. Human. Powerful.

✨ My 2025 in Five Honest Moments

Modelling the kind of reflection this exercise invites.
(Drawn from my own notes this year.)

1. I did things I once thought were out of reach.
I made two direct angel investments into mission-driven, female-founder-led businesses - something I couldn’t have imagined doing a year ago.

2. I backed myself to build something new.
I returned to early-stage venture creation and remembered just how energising it is to build from scratch.

3. I honoured a boundary I’d been avoiding.
I stepped away from a toxic board situation instead of forcing it to “work.” That choice restored more energy than I expected.

4. I challenged a habit that’s been quietly holding me back.
I finally faced the truth that I’m still not articulating my value strongly enough at board level, and it’s time to change that.

5. I noticed the patterns I’m ready to leave behind.
From revenue uncertainty to saying yes to unpaid speaking out of FOMO - certain dynamics kept repeating, and I’m ready to shift them.

Not polished. Not packaged. Just honest.

Now it’s your turn.

🥂 Part 1: What’s Worth Celebrating?

Not the Instagram wins.
Not the investor-update victories.

The real growth.
The inner shifts.
The courage that didn’t make it into your metrics.

Ask yourself:

1. What did I do this year that felt impossible a year ago?
2. What’s the bravest decision I made - even if no one saw it?
3. Where did I back myself, and what did that unlock?
4. What would the January 2025 version of me be proud of?
5. What boundary did I finally honour?
6. What do I now do with ease that used to drain me?
7. What am I deeply proud of that no one clapped for?
8. What would my future self thank me for?

Sit with these.

This is where your real progress lives.

🚧 Part 2: Where Did I Get Stuck?

These aren’t failures.

They’re the clearest signposts you’ll get all year.

1. What decisions did I delay - and what did that cost me?
2. Where did I say yes out of fear, not clarity?
3. What uncomfortable truth did I avoid?
4. What role or task am I holding that someone else should own?
5. What repeated pattern am I tired of seeing?
6. What feedback did I quietly ignore?
7. What boundary did I keep breaking - even though I knew better?
8. What am I still carrying into December that I should have put down months ago?

These questions sting for a reason.

That’s where the insight hides.

🧠 And Then… Something Shifts

When you stop and actually answer these, you start to see differently.

You stop explaining.
You stop justifying.
You start noticing.

And once you see something clearly, it’s impossible to unsee it.
That’s the start of real change.

If one of these questions made you pause - or wince - that’s the one to begin with.

And if you want help turning these reflections into a sharp, confident strategy for 2026, that’s exactly the work I do.

🎯 Book a Strategy Reset Session for early January

Let’s build a plan that fits who you are now, not who you were a year ago.

PS. You don’t need to answer all 16 questions.
Start with the one you least want to.
That’s where the truth is.