Most small business owners jump into planning with a notebook full of ideas, a great sense of urgency, and the pressure to “start strong” in the new year.

But real planning doesn’t start with ideas or action steps. It starts with clarity.

And clarity comes from asking yourself the right questions before you even touch a calendar.

If planning has felt overwhelming in the past, or if you’ve made plans that looked great on paper but were hard to follow in real life, you’re not alone. Most business owners skip the step that makes everything else easier. They rush ahead instead of pausing to make sure their decisions are rooted in what matters most.

Before you build a strategy for 2026, take a breath and walk through these three simple, grounding questions.

Behind the Strategy: Why Your Planning Doesn’t Stick

If you’ve ever made a beautiful plan and then never followed it, you didn’t fail. Your plan simply wasn’t built on the clarity you needed.

Here’s what I see often in my coaching and strategy sessions:

• You set goals based on pressure, not capacity.

• You create plans based on what you think you should do.

• You skip over what’s already working.

• You forget how much time and energy certain tasks actually take.

• You plan for the “ideal week,” not the real one.

This is why planning feels heavy. You’re planning without understanding the foundation you're standing on.

That foundation is your clarity.

And clarity comes from three simple questions.

Question 1: What actually worked well for you last year?

This question matters more than most people realize. We spend so much time thinking about what didn’t work that we forget to celebrate or build around the things that did.

Think about:

• Where your best clients really came from

• What content or marketing created engagement

• What systems made your life easier

• What gave you momentum

• What tasks felt natural instead of forced

When you start planning from what worked, you create a strategy that plays to your strengths and removes unnecessary stress.

Most business owners plan as if they’re starting from nothing.
You’re not. You already have wins. Use them.

Question 2: What created friction or frustration last year?

Friction is one of your biggest teachers.

Friction shows up as:

• repeating the same problems

• spending too much time on certain tasks

• feeling confused or stuck

• bottlenecks in your client experience

• content that takes forever to create

• tools you pay for but don’t use

• systems that are halfway set up

• being reactive instead of proactive

When you recognize where the friction is, you can simplify instead of stacking more tasks on a shaky foundation.

You don’t need to overhaul your whole business in January.
You just need to understand what kept you from moving forward last year.

Question 3: What do you want your business to feel like in 2026?

This is the question most people skip, but it’s the one that changes everything.

Your business should support your life, not leave you feeling exhausted, behind, or overwhelmed. When I ask clients this question, their answers are usually emotional before they are strategic:

• “I want things to feel easier.”

• “I want to feel organized.”

• “I want more predictable weeks.”

• “I want to feel supported.”

• “I want to enjoy my business again.”

How you want your business to feel determines how you should plan, what you should focus on, and what you should let go.

If you want a calmer business in 2026, your plan needs more simplicity.
If you want more visibility, your plan needs more consistency.
If you want more ease, your plan needs better systems.

When you choose the feeling first, the actions become clearer.

Bringing Your Answers Together

Once you’ve answered these three questions, planning becomes easier and more aligned. You’re no longer guessing. You’re no longer building a plan based on pressure or comparison. You’re building it based on:

• What’s working

• What needs to change

• What supports the life you want

This is the foundation that makes a yearly strategy feel doable, not overwhelming.

You deserve a plan that fits your business and your life.

FAQs About Planning for 2026

Q: Why should I reflect on last year before planning for 2026?

A: Reflecting on last year helps you identify what worked, what felt easy, and what generated results. Without this clarity, you may create a plan based on assumptions instead of reality. Starting with reflection ensures your 2026 strategy is grounded, focused, and less overwhelming.

Q: How do I know what to focus on when planning a new year?

A: Look at three things: what worked well, where you experienced friction, and how you want the year to feel. These answers help you prioritize what truly matters so you can build a plan that is aligned with your goals and capacity instead of trying to tackle everything at once.

Q: What if I feel behind or unprepared for 2026?

A: You’re not behind. Many business owners feel rushed at the start of the year. The best place to begin is with clarity, not pressure. Answering these three questions will help you reset, gain direction, and make decisions that support your business without adding stress.

If You Want Support Getting Clear on Your 2026 Plan…

This type of clarity work is exactly what we do in my strategy sessions. We simplify your systems, look at where friction is happening, and build a plan you feel confident about.

If you’d like to talk through your answers or explore the right next steps for your business, you’re always welcome to book a free 15-minute call.

Let’s make 2026 the year your business finally feels aligned, grounded, and clear.

Message Kristina directly: