The “How” of Tailored Simplicity
Monday June 16, 2014

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“People are remarkably bad at remembering long lists of goals. I learned this at a professional level when trying to get my high-performance coaching clients to stay on track; the longer their lists of to-dos and goals, the more overwhelmed and off-track they got. Clarity comes with simplicity.” -Brendon Burchard

The endless list of choices we have in our modern world is a marvelous and a fairly new phenomenon. Which clothes to wear, what food to eat, what job to pursue, where to travel, what to read, where to live, etc, etc. The list of options for nearly everything is extensive, growing and seemingly endless. But as psychologist Barry Schwartz reminds readers in his book The Paradox of Choice, so many choices can paralyze us if we don’t know how to clarify what it is we seek (view his TED talk on the subject here.)

The gift of choosing to live simply and incorporating our ideals into how we pursue our goals which will build the fulfilling life we seek is to understand tailored simplicity.

What is ideal for you, may not be ideal for me, but it is in understanding what you value, what has worked for you in the past, what you have no control over and what is available to pursue that allows each of us to gain clarity about what indeed will be worth seeking once we attain it.

Have you ever pursued a goal, and upon arriving at your desired destination been disappointed at what you had worked so hard to achieve? Well, I can honestly say, I have made that mistake a few times, okay, perhaps more than a few times. But what I’ve realized is that I wasn’t applying the tailored simplicity guideposts. I may have included, without knowing it, one or two of the guideposts, but I had forgotten to examine closely what had worked (or not worked) in the past and why. Needless to say, it is when we examine each of these guideposts prior to making a life changing decision that will create the peace of mind during the journey and help us to arrive at a destination worth arriving at in the end.

What is Tailored Simplicity?

Tailored simplicity involves four parts:

  1. The Future – what we wish to achieve
  2. The Past – where we’ve been and how it has gone
  3. Inner World – Values – the priorities we live by every day, what guides our decisions
  4. Outer World – Options – understanding what is out of our control, and thus understanding what is available

When does Tailored Simplicity come into play in our lives?

Anytime we are making a decision that will change the direction or routine of our lives. Career options, relationships, where to live, health habits, where to travel, etc. Especially when it comes to significant life decisions, understanding how to use the four guideposts of Tailored Simplicity will reduce indecisiveness and help you to come to a final decision that sits well with your conscience.

So how does it work?

Let me walk you through the process using one of my recent life choices as an example and show you how I arrived at my decision. When I announced recently that I would be moving to Walla Walla, Washington, many people looked at me quizzically. The questions about commuting were raised and others, but not one doubtful reaction sparked doubts within me. Why? I had gone through the four step process that I am about to show you.

So let’s get started. Grab a piece of paper or a journal and get ready to make a few lists (my responses will be in italics):

1. The Future 

What do you want to change? What are you seeking that you currently don’t have?

  • opportunities for regular cultural/art events
  • proximity to college classes for extended learning
  • fresh produce, healthy food options
  • a community with similar values
  • walk and bike ability
  • four seasons
2. The Past

Closely examine your past experiences to determine what you liked and didn’t like, what felt comfortable and on target and what didn’t. Then examine further – why did certain relationships/jobs/destinations work better than others? Be honest.


  • Paris/London – loved being able to live without a car, the accessibility to endless museums, plays, events.
  • Paris, Walla Walla – the local artisans – their foods, produce, crafts – offered an opportunity to support the local businesses and build a sense of community
  • Portland – the fresh food available and attention to health
  • Bend, Walla Walla, Portland, Paris, London – the abundance of opportunities for mindful stimulation – classes, discussion groups, activities, etc – the adults had options to continually grow and be curious
  • Pendleton, Bend, Walla Walla – a sense of community, fantastic neighbors and quiet neighborhood


  • Portland – too big, felt boxed in
  • London/Paris – cost of living, couldn’t own a home and renovate (not yet anyway)
  • Bend – not a big outdoors person
 3. Inner World – Values

Now is the time to outline what you can and can’t live without. What are your deal breakers?

  • A small home to call my own
  • An affordable cost of living
  • Able to live with my dogs – dog-friendly community
  • Similar values
  • A love of teaching. Wherever I live, I need to be able to teach.
  • Opportunities to continually grow and explore
  • A safe and friendly neighborhood
4. Outer World – Options

Time to get real. Much like house-hunting, we can create a dream-list of what our house has to have before we buy, but the reality is, we’re going to have to give a little, because we can’t create or dictate to the world how it should exist. It already exists, and it is our job to weed through all of the options and find the best one based on what the other three guideposts have revealed.

  • Where am I willing to move? How far? 
  • I searched in state and out, and as you can see, even considered international destinations. I really had no limits.
  • Upon deciding on 2-3 towns/cities, I made sure to give myself time living or spending significant time in each in order to feel as authentically as I could what it would be like to live there. 

Now what?

Make a decision. The guideposts provide an easy way to toss aside what isn’t going to ultimately be the best option and reduce any energy that would be wasted pursuing those dead-end routes. With each step you begin to narrow in more precisely on what the options are that are available. And by the end, you have a very concise list of what an option has to have in order for you to even consider it.

My decision, based on five years of searching, exploring, examining and putting myself in the shoes of someone who lived in each of these towns as much as my budget would allow, made the decision to move to Walla Walla overwhelmingly and refreshingly obvious. 

When you get to that point, having such conviction with your decision will instill in you a resolute sense of confidence that will pull you through those times along the journey that try your patience. Be willing to do the prep work, be willing to be very honest with yourself, and then the answers will be that much easier to find. Answers that will allow more contentment than you ever thought possible.


~3 Steps to Designing Your Best Life

~11 Things You Must Do to Create the Life of Your Dreams

~Are Your Listening?

5 thoughts on “The “How” of Tailored Simplicity

  1. Great post Shannon! Thank you for the link to Barry Schwartz’s book, I have just purchased it as an e-book and will view the TED talk, I’m quite fascinated with such issues at present.

    Extraordinary juxtaposition in the first and last photos!

  2. Per usual Shannon, perfect timing on your post! I am going to listen to Barry’s TED talk, like Rose above mentioned, this kind of topic is very prevalent to me at this moment. I also like how you gave us your real life example, very inspiring.

  3. This is such a thoughtful and unique post Shannon. It’s not often that we are able to see an entire breakdown of a major decision organized in this way. It can be intuitive for some seeing the process is helpful. I’ll check out the TED x. I’ve never been to Walla Walla but my nephew is in college there and loves it. Congrats on a ‘perfect’ decision.
    Cheers, Heather

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