How to Make Yearly Planning More Meaningful and Effective with Laura Posey

Stephanie Wasylyk
4 min readDec 6, 2023


What do you think of when you think of planning your business for the year?

Do you think of SMART goals? Do you think of the failures you’ve had in the past? Do you think about the plan you made but then promptly lost somewhere? Or do you think of nothing because you avoid planning at all costs?

We all have different relationships to planning. I happen to love it and look forward to it every year, which is why I find working with Laura Posey of Simple Success Plans so fun. Laura teaches business owners how to plan their year on one sheet of paper, and I’ve been at her side helping it evolve over the past 5 years.

In this video Laura and I talk about the pitfalls of planning, and what aligned planning actually looks like.

At the end we invite you to join us on an upcoming (free) workshop Laura is hosting called “How To Plan Your Year On a Single Sheet of Paper”. She’ll talk about what to put in your plan, and how you can join us for Plan to Win 2024. I’ll be there, so make sure to say hi!

This is my affiliate link to sign up for the free workshop. If you go on to join Plan to Win then I will get a commission (and I will be able to gift you some bonuses as a thank-you).

This is the direct link to sign up for the workshop without it being tracked back to me.

Watch the full video here (49 mins) and see the takeaways below.

Key Takeaways:

  • The essence of planning is deciding where you want to go, what you want to experience (when you get there and along the way) and making decisions about the fastest and easiest way to do that
  • Planning has to start with your vision and values so you know where you want your business to take you.
  • A good reframe is to not just think of yourself as the business owner, but like you also have a job. You would want to know what the company vision is and their plan, so you know if it’s the kind of place you want to work. What kind of company do you want to work for, and what kind of role do you want in that company?
  • SMART goals feel stressful and rigid, so think of goals more as milestones along the journey
  • Getting things on paper and into a plan helps you get it out of your head

We had three questions submitted ahead of time, and we address them one at a time:

I prefer to go with the flow so I find planning hard

  • Planning does not mean you have to have a boring business that is the same every day
  • Business is what helps us go with the flow in the rest of our lives, so we have to be intentional about what our business does for us
  • Keeping the plan really simple means you can still be flexible throughout the year and know you’re on track with your vision. A good plan is a framework that helps you make decisions that move you closer to what you want instead of further away.

How can I plan if I don’t know what’s going to happen?

  • Planning helps avoid distractions and that steer you off your path
  • Typically, it’s not your goal that changes, it’s the tactics to get there that can shift. And that’s okay!
  • A plan can help you filter any opportunities that come your way and help you decide what to do with them — it helps you know what to say yes to and what to say no to

I hate planning because I always feel behind or I can’t stick to my plan

  • A good plan has structure and some milestones you’d like to reach, but it’s not filled with all the little details
  • Your plan needs enough structure to keep you focused, but enough slack to adjust to daily life. This helps you make and see progress without feeling behind
  • Your plan should be unique to you and your business. It won’t work if you’re trying to run your business or make a plan that isn’t meant for you specifically.

Next Steps:

  1. Start with thinking about your ideal lifestyle. Get clear on that first before you dive into the business stuff.
  2. Calculate how much money and time you need to achieve that ideal lifestyle
  3. Think about what has to change in your business so you can achieve that ideal lifestyle
  4. Start taking notes on what you’d like in your plan for the year to get your creative juices flowing