HOW and WHY you should assess your life

Common: Finding yourself stuck in an unfulfilling annual process cordially called “life.”

Uncommon: Going through life without assessing performance, results, and direction only encourages monotony and mediocrity. Machines were created for mindless, rote tasks, not humans. In fact, what makes us unique compared to even the most sophisticated robots is our ability to reflect and ruminate.

Life should not be a mundane process – and nor does it need to be. With some thought, reflection, and planning life can become a journey of purpose and passion.  But I assure you, this doesn’t happen without being proactive and very honest with yourself. Keep in mind:

If you do not confront your past, you are destined to repeat it.

On this note, it is now the end of 2010 – an ideal time to, yes, you guessed it… reflect and ruminate. Yet, surprisingly, most people still neglect this valuable process.  I’ve noticed there are 3 common defeatist-mindsets when considering a year-end assessment:

  1. The delusional: “It’s not worth my time. There’s no value in this process of feel-good-fluff.”
  2. The reactive: “I don’t have time – I can barely keep up with life as it is.”
  3. The hypertensive: “I’m too busy living life and doing more worthwhile things.”

I will assume if you are reading this blog and struggle to take this topic seriously, it’s likely mindset #3 that you are facing. The trap many type-A go-getters fall into is believing that reflection is a reactionary activity, not a proactive approach. This, unfortunately, is a costly misconception.  Below are some logical reasons WHY it’s important to assess your life.

WHY should I assess my life?

  • We recognize where our time and effort is best spent.
  • We recognize where our time and effort is poorly spent.
  • We recognize indicators of progress and regression.
  • We recognize our strengths and our weaknesses.
  • It gives us the delightful sense of slowing time. We do more in 365 days than we often think and acknowledging this can alter the common belief that “there is never enough time.”
  • We can re-enjoy our best moments.
  • We internalize and retain life-lessons learned.

By three methods we may learn wisdom: First, by reflection, which is noblest; Second, by imitation, which is easiest; and third by experience, which is the bitterest. – Confucius

Action without reflection is likened to a car without brakes. There is potential for both a constructive and destructive outcome. The problem is, of course, it’s mostly out of our control.  Like anything in motion, the ability to stop (in this case, reflect) is what makes the journey safe, memorable, and masterful.

Consistent action without reflection enslaves us to habit.

Reflection gives us the awareness and insight to challenge predictable cycles of behaviors and make critical adjustments to what is not working while moving forth with more gusto on that which is working.  This brings us to the second part of this post: HOW to assess your life.

HOW should I assess my life?

  1. Schedule 2 hours in isolation. By “isolation,” I mean away from common distractions.  If you work best at a busy coffee shop, so be it. I suggest 2 hours because you do not want to feel rushed or rush the process. If you finish early, treat yourself to something else you enjoy doing.  The most effective times of day for this process are early in the morning or late evening, when distractions and demands are minimal.
  2. Avoid the internet. Turn off your wifi – or better yet, use only a pen and paper for this exercise. Reflection, in this case, presupposes the information you need is upstairs in the top three inches not “out-there” on the internet.
  3. Turn off the cell phone. This device is the number one perpetrator of private and personal time. You do not need your phone for reflection. In fact, leave it in another room.
  4. Record your thoughts for three reasons: One, passively thinking is not the same as writing. Retention, creativity, and engagement is higher when physical activity is required. Two, your notes will serve as a map and source of inspiration for the duration of the year.  And three, your notes will be important to review when looking back on the year. I suggest keeping all reflections/assessments in one book/journal so all of your notes are in one place chronologically.
  5. Ask the right questions. The greatest ideas, insights, and discoveries humans have made can be traced to specific questions. Questions began the quest to reveal the most pertinent, and sometimes unsuspected, information. For this reason, I have created a list of questions below that I have found helpful in my personal reflection.


Important questions and actions:

Part 1: Reflection and assessment.

  • If I had to sum up this last year in 5 words, what would they be?
  • What did I enjoy most this past year? Why?
  • What results/experiences would I like to repeat next year?
  • What did I find most frustrating? Why?
  • What went well this past year?
  • What did not go well this past year?
  • What were my top 5 (or more) lessons learned?
  • On a scale of 1-10, how would I rate my ___ (professional life, personal life, friendships, finances, spiritual life, etc.)?
    • Follow up question: What would it take to make it a 10/10?
  • What do I feel is missing in my life? What would fill the void?
  • Review notes and goals from last year’s reflection if applicable.

Part 2: Intention and design.

  • What 3 things would I have to accomplish next year to feel like the year was a success?
  • What will the theme of my next year be? (Can be a word or short catchphrase)
  • What should I learn more about? (both professionally and leisurely)
  • Based on this past year, what has held me back the most?
    • Follow up question: How can I better combat this challenge so the same issues do not hold me back in this upcoming year?
  • Set 5 goals in the following areas: professional, personal, family, friendships, finances, spirituality, etc.
  • In an ideal world, how would I describe my life: a) at the end of next year b) in 3 years?

Part 3: Follow up and accountability

  • When will I schedule the next appointments with myself to check-in on my progress and direction? (I suggest scheduling a minimum of 3 appointments during the year)
  • If I fail to meet a scheduled appointment, I will ____ (give up TV for 2 weeks, donate $200 to X charity, etc.)
  • I will remind myself of my year’s objectives by ___ (reviewing my goals every Monday night / keeping my notes on my nightstand / asking a friend to hold me accountable, etc.)
  • I will hold myself accountable to my goals in other ways by ______. (Be creative – the more interesting, yet simple, the more effective)
  • When I accomplish _____ goal, I will reward myself by ___.

You wouldn’t build your dream home without reflection and planning so why approach life haphazardly? Just remember, you won’t “find” time to do this. You will need to “make” time to assess and reflect. I have never met anyone who has regretted the process of personal reflection, but I have met countless individuals who have contributed their success to it.

Your thoughts?

Have any thoughts, questions, or techniques you would like to share? Post your comments below.

Stay uncommon,

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