Reflections: My Unplanned Year

It’s hard to believe, but a year and a half has passed since the beginning of my “unplanned year” experiment.

To recap, despite having an amazing job, one that I had been dreaming about and working towards for years, I felt compelled to make a big change.  I wanted to press pause on my life – to intentionally create space, and see what would come of it. I honestly didn’t know what the end result would be.  Had I been asked to bet on it, my money would have been on me returning to teaching with a deeper appreciation for the stability it provides; I have been so surprised by what has emerged instead.


The scariest part of making the leap to self-employment was the “should I/shouldn’t I” limbo beforehand. I am someone who likes to chart a clear path from A to B before acting.  This was a case where I had to leap first, and upon landing, look around and see where to go next.  I had to trust, trust, trust (in myself).

I discovered that thinking about doing stuff is scarier than actually doing it. And that saying, “I’d do it if I had more time” often isn’t true (ex: I told myself I would meditate every day if I wasn’t so exhausted from working, but after leaving that job, I STILL didn’t make time to meditate – it wasn’t until nearly a year after Vipassana that I developed a steady practice). I also learned that my ambition is a stable part of me, and that slowing down doesn’t make me less driven (which I had been afraid of).

At the start of the experiment, I set 12 goals, so here is a quick update:

Step Outside Comfort Zone

  1. Do Something New Every Month READ MORE HERE. Intentionally challenging myself is a fast-track to increased happiness.
  2. Go on 10 New Hikes READ MORE HERE
  3. Make 100 New Recipes READ MORE HERE

Creative Health

  1. Do The Artist’s Way (12-week course to help “discover and recover your creative self.”) READ MORE HERE
  2. Start a Writer’s Group (Using a shared prompt, write for 20 minutes, then read pieces out loud.)
  3. Take Acting Lessons  READ MORE HERE

Mental Health

  1. Develop a Gratitude Practice I’ve experimented a lot with this, but simply including it when I meditate has been the easiest. I am using this book for 2018.
  2. Attend a 10-Day Vipassana Silent Meditation Course READ MORE HERE. This is the best thing I did all year.
  3. Quit Shopping for a Year READ MORE HERE. This was the toughest one for me. I fell off the wagon in the spring, but I did cut down my personal spending by at least half, and was more conscious while make purchases.

Travel Priorities

  1. Go to Country #30 (Read this for more about my “30 by 30” goal.) Japan Trip: READ MORE HERE
  2. Weekend Getaway to Portland, Oregon READ MORE HERE
  3. Visit Corinne in Vancouver, B.C.  READ MORE HERE


This year has been wonderful, but it has also been hard. I have stretched and grown and tore myself open. I have created more time in my life – time to find the shadows and get to know myself and the many ways I look outward to find the things I should give myself.  To recognize that being alone can be soul-achingly painful… and revealing… and a gift. To learn that the antidote to loneliness is actually increased time alone. To sit uncomfortably with the realization that much of my busy-ness and commitments were shields, distractions, and protective devices keeping ‘me’ from knowing ‘me.’

I have been getting to know the corners of my heart and where it’s raw and covered in scar tissue. Going to the edges of that pain has been messy, extreme, and very disruptive. I’ve made mistakes along the way, some of which resulted in loss. I am slowly learning to soften and release instead of resisting and controlling, but it has not been easy.

I am now halfway into “Year 2” of this, and it’s no longer an experiment but just the way my life is designed. I love waking with no alarm clock, having control over my time, and working for myself. I have learned to move away from dread and toward expansion. I am more open and less guarded. I am more relaxed and spontaneous. I am happier. I am lighter. I am also ok knowing that my work situation could change and at some point, I might be happier going back to a traditional job. I am ok with being a moving target and adapting to the seasons of my life.

In starting my “Unplanned Year,” I had no map or destination. This leap of faith took me places I didn’t even know I wanted to go. I don’t know what the next year will bring, but I do know that I want to keep leaping, because I trust that wherever I land, I’ll be there, and am able to help myself figure it out.

Thank you for reading and for being with me on this journey.

❤ Kailea

2 thoughts on “Reflections: My Unplanned Year

  1. Hello, I am also a Harvard grad. I came across your post on Facebook. I wish you luck with your new venture.

    I couldn’t help but browse through a few posts, partly because those blog posts’ titles discussed things I am going through myself. I came across the site I’m linking to below a few years ago. It’s quite an Eastern thing really as most Americans don’t buy the influence of factors like one’s name on one’s life. I am not sure why I’m sending it to you now except that as I went on my journey like you recently did and perhaps still are, I found an analysis of my name to not only be accurate but also quite helpful. Take it for what it’s worth to you. Everyone’s mileage is different. Best wishes.


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