How Will You Ultimately Measure Your Success?

Tomorrow is the first day of my “first retirement”. That’s the day where I deliberately shift the way I think of myself from “needing to work” to “wanting to work”. The milestone has me thinking of it as the first day of the rest of my life, and asking questions about how I might look back on life when elderly. That got me thinking of a learning program I participated in a few years back where I was asked to write a letter to myself. 

The instruction was to imagine myself twenty or more years into the future, and to provide today’s self with advice and mentoring in planning for my future. What should my plan be about, and just as importantly, not be about. I sat and imagined an 80-year-old version of myself, having slowed down enough to take stock of my life, providing insights as to what I would know as the truths of my life. I occasionally go back and read this letter and still find it guides me well.

When I researched this on the web, I saw lots of suggestions for writing letters to the future.  Letters to one’s future self for example.  They tend to be about dreams and aspirations for one’s self.  Perhaps these are most useful for individuals in the first half of life as they explore their future potential, trying to remove limits from themselves.  I also see letters to future spouses, future children and future son/daughter-in-laws that express future desires for themselves and for others that are born out of love and compassion.

I love this aspirational way of being.  It leads to goals and visions for the future.  We then look to act on those goals and visions in the present in order to make them more likely to come to pass.

I see much less discussion of letters from the future.  Perhaps because this approach is less about goals and visions and more about purpose and passion.  Perhaps that part of us is more personal and introspective.  Perhaps we have less need to share our thoughts with others and more of a need to know them deeply inside us.  Perhaps this approach might be more the domain of those in the second half of life, wanting to know that their life will have had meaning and that they personally have made a contribution.

The purpose is a bit different from a letter to the future.  It isn’t so much aspirational in nature as it is to really understand how we want to be right now, and what we need to do to bring that which is already within us to the surface.

I also wonder if this might not be a great approach for those approaching the latter part (maybe the last 10 years) of their careers.  To write a letter from their retirement date as to how they feel they added meaning to their company, their profession, their colleagues and/or their community by using their experience and wisdom well.

So here’s my letter from my 80-year-old self.  I would endorse this as a worthy exercise for anyone looking for a new perspective on what is important in life, particularly those in or approaching the second half of life.

A bit of context: when writing this letter I acknowledged to myself that my gifts are as a builder and as a facilitator. Please think of your own innate gifts as you read that section.

As always I appreciate any feedback you have about this approach.  How does the device of using a future self-perspective help in creating meaning and purpose in the present?


To my emerging self,

It has been a fabulous ride to this point, filled with much learning. As you contemplate the next steps in your journey to where I am now, please know these truths.

You will not be remembered for your productivity, or your position. You will not be remembered for the decisions you make. You will not be remembered as “better than”, or “worse than”, someone else.

You will be remembered for the depth and impact of your connections with others, the truths you express, the creations you leave behind for the benefit of others and the contribution you make to the others’ journeys. You will be remembered for the joy, the possibilities and the positive energy you leave behind in the form of other people’s experiences.

Love yourself first, and once you are sure that you do, be vulnerable and share yourself with others such that they can know and call on your gifts.

Do what you were born to do. When you see something that can be built, build it and others WILL come. When you see the opportunity to facilitate progress or agreement, offer your services and they will be valued.

Do not react hastily. Know your own truths and act consciously from them. Respond with equal measures of truth and compassion, leaving room for the unknown.

Express yourself openly and fully when something has meaning to you. Encourage debate and dissent so you may learn.

Release the creations that are trying to emerge from you.

Contribute to your community and to the world so that it may heal and grow.

Measure your success in life by the richness of experiences you have had and by the connections you have fostered, enriched and been enriched by.

Above all, strive to be present in each moment as it is unique and will never appear to you again.

We each have great gifts and energy to offer to our communities. The only shame is in not giving them.

Offered with love,

Your Inner Sage

Published by

Ian Munro @

Ian Munro is a leadership and vitality coach with a primary passion for working with senior professionals who wish to improve their connection to and vitality in their career, or who wish to make a transition to a meaningful and rewarding retirement. His methods are focused on helping clients understand why they present as they do in day-to-day life, discover their authentic self and give themselves permission to build a meaningful and rewarding future, both professional and personal. Ian’s love for this work has developed naturally as he built his career as an executive and leader in the IT services industry, serving in many roles and facets of this industry over 25 years. As he reached the pinnacle of his career he began to search more deeply for meaning and alternate rewards from his own career and to begin to plan for his own “first retirement”.

6 thoughts on “How Will You Ultimately Measure Your Success?

  1. WOW!

    What a powerful wise self you are in the future — and now.

    Love this Ian. My daughters gave me a book on my birthday that they created. In it, they invited people to write me letters about what makes me a good person. They used the format I had used for the books I created for them on their 13th, 18th and 21st birthdays. The letters are wonderfully uplifting, affirming and inspiring — not to mention, deeply moving.

    I have done your exercise long ago — have no idea where that letter is! I also did one where I wrote my eulogy — another powerful tool for self-discovery and discernment.

    Let’s meet up in your new condition of wanting to work! I’d love to catch up and talk about your idea!

  2. I think you writing a letter from the perspective of your 80- year-old self is a fascinating one. Having shared the caring of my 88 year-old mother for the past eight months until her death, I did a lot of reflection as to where I would like to be at age 88. It was quite compelling and helped pushed me into some major life-changing decisions as to where I would like to spend the next twenty years, who I would like to spend my time with, and what I would like to be doing.

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