Transcript – Episode 57 – Josh Caucutt – Planning to Plan

On episode 57 of Shit We Don’t Talk About, Mia is joined by financial planner Josh Caucutt. Josh is here to share tips and tricks on … well … how to get your shit together!


  • Josh is a huge fan of having a drama-free life. One of the best ways to achieve that is to have a plan. Figure out who you want to be, then have a plan to get there. Sounds simple, doesn’t it?
  • Having a plan starts with understanding where you are now. Know the condition of your flocks. If you’re oblivious to what’s going on around you in any aspect of your life, it will be difficult to know where to go or what to do next.
  • A bad plan is better than no plan. Most of us need to experience a busted or broken plan now and then so we can see when we’re going down the wrong path. It’s better to have a plan with bugs in it than to have no plan and drift aimlessly. A plan with flaws can show us when its time to change the plan!
  • The best plans are the plans that fit your life.
  • There are more than one ways to skin a cat, but if you’ve considered no ways, then it’s going to be difficult to get that cat skinned.
  • Having a plan can actually enhance creativity. Imagine that? But when we have a plan to follow, our brains are free to work on other things. Steve Jobs wore the same outfit every day because he didn’t want to waste any brainpower on his clothing. He made plans for the mundane and repetitive stuff, freeing his brain to focus on more creative and impactful issues.

“Structure allows you to be creative.”

  • In an organizational setting, leaders that have a plan and clearly communicate that plan and its parameters give members of the tribe a strong foundation to stand on. This is a prerequisite for creativity for many people. You can love your boss on a personal level, but if they are freewheeling it every day and providing no basic structure, that person can be very difficult to work with.
  • Sometimes the process of talking through the broad strokes of a plan can show us that we’re planning for the wrong thing. Before you try to fill in all the nooks and crannies, look at the big picture first. That will help you fill things in later, or it may show you that you’re going in the wrong direction before you waste all that time on nooks and crannies!
  • In some aspects of life, planning can be VERY distasteful. Talking to aging parents about healthcare and financial plans is difficult so we often avoid it. Planning for death and final arrangements isn’t something any of us wants to do. Life emergencies and disasters are things we do not want to acknowledge so we don’t plan for them. Planning a way to get your children out of your house because at some point they have to become independent is not an easy thing to do. Nonetheless, plan we must!
  • Being at least a basic planner makes you a good steward for the rest of the people in your life. Refusing to plan can make things difficult for the people we live and work with. Having a plan is a way of showing respect for the people you care about personally and professionally.
  • Sometimes we refuse to plan because not having a plan gives us a way to wiggle out of accountability when things don’t go well. Think about it.

About Josh Caucutt

Josh is a financial advisor in Lakewood, Colorado. Originally from Wisconsin, Josh spent 15 years as a college soccer coach and then transitioned through several opportunities as a sales professional until finally becoming a financial advisor.


John’s website

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Music Credits:

Inspiring Experience by Rafael Krux


Inspirational Infinity Of Space by WinnieTheMoog