My Unplanned Year

I am a planner. I have been goal-setting since elementary school.  I write down “shower” on my to-do list so I can check it off.  I make day planners FOR FUN.

But this year, I am trying something different. This will be my unplanned year.


As I start this year-long experiment, I am 29 years old. I’m pretty sure that when I turn 30 I won’t immediately have 3 kids and a mortgage, but given that I’m eager to have babies and only plan to live in LA for the next year, I feel like it’s a unique time to take a leap of faith. I’ve had a clearly defined plan for as long as I can remember, but now I’m ready to take my own version of a ‘gap year.’

I started to dream about making a shift like this almost a year ago. Those close to me know it wasn’t an easy decision. I was working in a school that I absolutely loved, with the most wonderful kids, getting full-time experience as a teacher, and I had a nice stable income with benefits. It was the path I’d been actively setting myself up for since high schooland yet, I wanted off the path.

The thing is, I absolutely love teaching. Being with kids makes my heart happy and it’s very possible that teaching is what I’ll return to after this experiment, but for some reason, there is a voice inside me saying, “Now is the time to make space in your life for the unexpected”- and I’m listening.


Some people have been shocked when they hear what I’m doing and have referred to it as a life crisis. I looked up the definition of “crisis” to see if it relates with how I feel; I found the most beautiful word listed as its antonym: “heartease,” defined as rest, repose, serenity, and peace of mind. Now that resonates with how I feel.

I read several books that helped me gain the confidence I needed to make this change:

  • Big Magic by Elizabeth Gilbert
  • Daring Greatly/Rising Strong by Brene Brown
  • The 4-Hour Workweek by Timothy Ferriss

Two of the questions in Timothy Ferriss’s book really opened my mind:

1) What is the worst case scenario and what would you do if that happened? 

It shifted my perspective when I realized that the scenarios I came up with were either preventable or could be easily dealt with. The risk was actually pretty small.

2) If you had $100 million in the bank, what would your days look like?

Here is what I wrote:

  • Wake with no alarm
  • Read!
  • Exercise when I feel like it
  • Make good food
  • Meditate
  • Have time to create
  • Spend time near the water/the ocean
  • Feel helpful to others
  • Be with kids
  • Connect with people I love
  • Be generous to others

I realized I wouldn’t need very much money to facilitate a life that looked like that.

And I felt free.


This is a year about creating space and seeing what comes up. This will involve being alone with myself much more than I’m used to. I’m currently working through The Artist’s Way. One of the weekly assignments is to take yourself on an “Artist’s date,” and it says:

“You are likely to find yourself avoiding your artist dates. Recognize this resistance as a fear of intimacy – self-intimacy. Often in troubled relationships, we settle into an avoidance pattern with our significant others. We don’t want to hear what they are thinking because it just might hurt.”

In other words, it isn’t always easy to be alone with ourselves. If any discomfort arises, I want to lean into it.

I don’t know what is going to happen this year. It’s possible at the end of this experiment I will say, “That’s why I need a 9-to-5 job!” It’s also possible that this year will mark a dramatic pivot from the path I was headed on. Either way, I am open to any and all outcomes.

I am noticing my desire to structure this experiment, to list what you can expect from me this year – in other words, a desire to plan my unplanned year.

It is hard to allow this to be what it needs to be, but thank you for being with me as it unfolds.

❤ Kailea

2 thoughts on “My Unplanned Year

  1. Kailea! As I think you know, I am so thrilled for you! Following your inner calling is a very courageous and amazing thing to do. I am very certain that this year will hold HUGE growth and love for you!! I’ll be cheering you along each step of the way!


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