Design Your Life using The Odyssey Plan
July 7, 2017

If you want to build your ideal life it has to begin with you.  No one is going to sit you down and tell you it’s time to start planning.  No one is going to show you your path.

It’s up to you to decide when to start and which direction to choose. 

To be honest, it’s going to take a lot of work.  It’s going to force you to look within yourself like you never have before.  

And it’s for these reasons that the majority of people never start the process in the first place.  The process is hard.  It’s much easier to float through life by avoiding these deeper questions.  

But what if you wake up 20 years from now realizing you were in the wrong career?  What if your innate talents had gone unused and your greater purpose undiscovered?

Luckily, this doesn’t have to happen to you.  It’s not too late.  You can designing your ideal life and you can start NOW.  


One of the most influential books I read in the last year, Designing Your Life by Bill Burnett & Dave Evans, taught me how to start thinking like a lifestyle designer.  In this book these two Stanford professors talk about how to build a career that you love by shifting the focus away from resumes and job boards and back onto you!  They provide countless success stories from their students and a plethora of resources.  

These resources (which can be found on their website) include exercises that help you reflect on your own skill set, passions, and values.   One of my favorite exercises is known as “The Odyssey Plan.”  In this exercise you make a chart of three possible alternative lives you might live over the next five years.  

The key to this exercise is to not restrict yourself to what seems possible now.  Instead, you want to truly dream about your three best possible lives.  By completing this exercise you will be able to visualize the three career paths before you and begin testing them out little by little. 


The Odyssey Plan

Below I have provided my Odyssey Plan exercise which I did back in the fall of 2016.  As you can see, I mapped out three possible careers:

  1. Blogger
  2. Life Coach
  3. Hospitality / Experience Curator

In addition, under each of these possible lives I answered the following questions:

  • What problem does this career solve for me?
  • How would I make money?
  • What are the pros?
  • What are the cons?
  • What’s my 5 year outlook?
  • What can I do now to test out this career?

Take a look below at how I worked through this and start thinking about how you would craft your own Odyssey Plan.

Do you see how it works?  It’s very simple and it should even be fun as it allows you to picture yourself walking down career paths designed by you.

However, you should know that once you’re done with this brainstorming exercise your work has only just begun.   After you’ve come up with these various lives for yourself you must start to slowly test them out in your life.  

In your day-to-day you need to find small ways to experiment with each life.  For my three examples listed above I have been able to do this over the last six months.  Straddle The Line fulfills the Blogger requirement.  My career coaching service covers the Life Coach aspect.  And my tour guide service covers the Experience Curator portion.

If it’s too much for you to experiment with all of them at once then I recommend testing out one at a time.  The key is to start.  The sooner you start thinking like this, the sooner you’ll see your new life start to take form.  


I hope that this exercise provides you with the type of help that it did for me in my soul searching.  And while I am still working on finding a clear path, I don’t mind experimenting with all three for now.  I’m having fun with the process and that’s all I can ask for.  

So will you join me on this odyssey?  Will you choose to forge your own path?  

The choice is yours. The time is now.  



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