Planning Retreat - No. 5 - Main Planning Day


Backstep Forward

by Kyle Mast, CFP®


A short, to-the-point, weekly thoughtletter.

One challenge to take a step back.

One idea to propel you forward.


“What do I want my life to look like one year from now.” (Share this on Twitter)


It’s time for the main planning day of your planning retreat. This post will be longer than normal to get all of the information in for this great day. Here we go!


Backstep - The First Session

This session will last until mid-afternoon.

Your goal here is to think very big and broad. Don’t hold back. Don’t limit yourself. Take a break for lunch. Come back and brainstorm. Take a walk on the beach (you are at the beach, right?) to think about your goals and the possibilities. Come back to the sticky notes or whiteboard. Take more breaks. Go for a hike. All the while, think and let your mind really explore what you want your life to look like and what you would like to accomplish. Pray that God would be a part of the process and show you how to use the gifts he has given you. If you don’t know God, pray anyway. What would it hurt? :)

Don’t think too much about the “how.” That will come later. Think more about the “what” you want to accomplish and “why” you want to accomplish it. There is always a “how” that can be crafted later. Thinking too much about how you will accomplish your goals too early can discourage you from thinking big and broad enough.

Here are some questions to help prompt your thinking. As ideas come to mind, throw them onto sticky notes on the wall or a whiteboard (or mirror or window in your hotel room). The goal is to plaster your accommodations' walls with ideas and thoughts.

It can be helpful to write some of the following questions down on a small piece of paper to carry throughout the day.

  • What does my ideal persona look like?

  • What does my ideal day look like? Work, play, learning, family, etc.

  • What does my ideal year look like? Work, play, vacation, etc.

  • How many hours per week do I want to work?

  • What are my ideal working hours, and what do I want to be doing?

  • If money were not a concern, what would I do with my life?

  • How can I remove money as a concern in my life?

  • How can I accomplish my ten-year goals in the next six months?

  • Am I currently using my gifts and expertise to my fullest potential?

  • What needs to be removed from my life so that I can use my gifts to their fullest potential?

  • What excuses am I making for not growing and pursuing my fullest potential?

  • What do I want my life to look like one quarter/year from now?

By the end of this session, you should have several big ideas and or goals, either for your life, this year, this quarter, or all of the above. You may have many sticky notes and ideas written all over. That’s great! We will distill them down next.

Throughout this day, take breaks to walk or grab a snack. Moving to a different location (coffee shop, restaurant, etc.) every 90 minutes or so will help when your mind starts to feel tired. I am a huge fan of 15-minute power naps.

Forward - Second Session

This session should go from mid-afternoon until dinner or a bit into the evening.

Looking at all of your potential goals and ideas you’ve written down, begin organizing them by similar categories and goals, reducing them down as much as possible. This is where it is nice to have everything on sticky notes so that you can rearrange them on the wall and throw away ones that are similar or duplicates.

Spend thoughtful time slowly curating your ideas and thoughts down to your most important and essential goals. We will work on the next steps and actions for achieving the goals tomorrow morning. For now, just work to clearly identify your most essential goals.

Enjoy a nice dinner and a quiet evening.

After dinner, you are free to just relax for the rest of the evening. You may feel mentally exhausted and want to just rest from all the heavy thinking. That is a good thing. Allowing yourself to rest after such deep thought will help you process it all tomorrow.

On the other hand, after eating something and a little walk, you may feel re-energized and want to begin working on your action plan. You can jump to tomorrow’s morning agenda (in the next post) and begin that process and do as much as you want until you begin to feel fatigue set in. Don’t push it though. Rest is very powerful in providing you with clarity and helping you make the best decisions.

“What do I want my life to look like one year from now.” (Share this on Twitter)

Kyle Mast, CFP®

My Why. What’s Yours?

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Kyle Mast