Life planning

and applying some Disney movie lessons

We’ve been listening to the Moana soundtrack on repeat for the past month. It was playing in the background as I started writing this. Thankfully, my kids go to bed before 8 pm, or I’m sure our downstairs neighbors would complain about the amount of bouncing around that has been happening to ‘You’re Welcome’.

If you don’t have young children or aren’t well-versed in Disney characters of recent years, I’d highly recommend the movie and soundtrack (featuring songs written by Lin-Manuel Miranda). Moana is the daughter of the village chief and is expected to take over the leadership of her island village. But she has a different calling. A dream. A longing to explore the ocean. There is what she ought to do and then what drives her and brings joy to her life.

She chooses to honor her mission in life and goes on an epic adventure that (I won’t ruin the plot line) ends up better than she could imagine (but we all could because this is a Disney movie, after all).

Life planning sounds serious but it’s really about channeling the same energy Moana does. It’s about discovering what adventure you are going to go on. It’s asking - what is your optimal life? Are you living it? Are you creating it?

It starts with suspending reality for a moment and letting go of perfect logical reasoning to dream and brainstorm. Forget about the financials - you often have more options than you think, and we’ll get there.

Cynicism, skepticism and doubt are checked at the door. If we censor what we want, whether it’s a revitalized relationship with our family, a sensible tax and saving program, or our lowest possible handicap at golf, our Life Plan will be incomplete and full of hidden obstacles and subterfuges. - Life Planning for You, George Kinder

While there are a lot of people thinking and writing about life planning/lifestyle design* I take most from George Kinder’s approach. He has three famous questions he uses to initiate life planning that I think are worth taking the time to consider.

They are meant to be contemplated one at a time, only moving on to the next question when you have fully engaged with the last. Try it for yourself.

1. Imagine that you are financially secure and that you have all the money you need for the rest of your life. How would you live your life? Would you change anything? What would you do?

   Let yourself go. Don't hold back on your dreams. Will you change your life and how will you do it?

2. This time you visit your doctor who tells you that you have only 5 – 10 years left to live. The good news is that you won’t ever feel sick. The bad news is that you will have no notice of the moment of your death. What will you do in the years you have remaining?

   Will you change your life and how will you do it?

3. This time your doctor shocks you with the news that you have only one day left to live. Notice what feelings arise as you confront your very real mortality. Reflecting on your life, on all your accomplishments as well as on all the things that will remain undone, ask yourself:

   What did I miss?

   Who did I not get to be?

   What did I not get to do?

A lot of times, these are big lofty ideas. I would quit my job. I would travel. I didn’t get to see the pyramids. I didn’t spend enough time with my family. The next step is organizing and refining these ideas.

One exercise I like that I’ve seen numerous iterations of is to sketch out your ideal schedule.

What does an ideal day look like? I liked Chris Guillebeau’s idea of imagining an 8th day and Tim Urban’s idea of the mundane Wednesday (what does a mundane Wednesday look like matters because “in fact the mundane Wednesday is the experience of [your] actual life.”

What would an ideal week look like? How about an ideal year?

How do your current days and weeks compare?

Over the next week, add your shower thoughts and details as they arise. Where do you want to travel? What are you going to do? Who is going to be there with you? When is this going to happen?

What did and what didn’t work today? What do you want to cultivate more of? What energized you? What engaged you? What left you feeling drained? Are you living your values? Try things. Each day is a living iteration.

Give yourself plenty of time to live in this space, for at least a day, preferably a couple of weeks, before you begin to address the obstacles. Make your dream richer and richer as you live into it. Make it alive. Your passion will change the world – this is the life you were meant to live and this is the person the world most needs you to be. It is your brilliance, your genius, your authenticity. It is what sets the world on fire. - Life Planning for You, George Kinder

It all sounds a bit woo-woo, but too often, financial planning starts with optimizing money. However, optimal money is not always optimal life. We have to know what we are optimizing for, though, because what you want to optimize for will be radically different from what I want to optimize for. 

Resources

*I realized that every single one of the life planning/lifestyle design thinkers I know of are men. If you know any women writing about life planning, please share! Not to say that they don’t have good ideas and aren’t worth checking out:

George Kinder’s ‘Life Planning for You’ interactive website walks through his questions and other exercises to help you discover your life plan

Ramit Sethi's ‘Design Your Rich Life’ is designed as a course (it’s free) that has videos, text, and exercises that are meant to guide you in creating your own ‘Rich Life’

A short article by Cal Newport on lifestyle design is a classic

If you want to read a whole book I enjoyed:

Designing Your Life & Die with Zero