What Was I Thinking (when I was in your shoes)?

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What was I thinking?   

For each of us on our retirement journey, we’re walking in the footprints left by those who have retired before us. If you’re one year away from retirement, you’re standing in the footprints I left in June 2017.  What was I thinking when I was a year away from retirement?  That thought led to a new idea for how I can (hopefully) add value for you and resulted in today’s post, which seeks to accomplish that goal.  

I’ve decided to lay out my footprints for you, wherever you are on your retirement journey.  Breadcrumbs on the trail, so to speak. If you’re within 3 years of retirement, you’re going to be able to follow my “thought footprints” as I walked the journey 3 years before I retired. If you’ve recently retired, you’ll see what I was thinking in my first year of retirement. In today’s post, I’ll be providing a roadmap of my key thoughts as I walked along my retirement journey. 

Jump to wherever you’re at in the timeline below, and you’ll be able to see “What Was I Thinking (when I was in your shoes)”.

If you’re 1 year away from retirement, you’re standing in the footprints I left in June 2017. Today, I’m sharing what I was thinking when I was where you are on your journey. Click To Tweet

We can all learn from each other, right?  With that thought in mind, I’ve decided to create this “What Was I Thinking Timeline” to make it easier for you to find relevant content, regardless of where you are on your journey.  I’ll start each time period with a macro overview of what I was thinking about, then include the most relevant posts from the same timeframe.  

You can see What I Was Thinking when I was at the same point in the retirement journey that you’re at today. Click To Tweet

I’ve also restructured my “Every Article Written” page to make it easier to place yourself on the timeline for all of my articles, adding the timeframe from retirement every 6 months in the calendar of my posts.  Have a look, and you’ll now find the following new tip at the top of the page:

With that, let’s have a look at the timeline, and answer the question of “What Was I Thinking” as I left my footprints in the sand.  As my regular readers know, I like to mix up both “Hard” ($$) and “Soft” (Purpose) articles, and have included several of each time in the timeline…

3+ Years To Retirement  (June 2015)

I started my blog in April 2015, just a bit more than 3 years out from retirement.  It was at this point of the journey that I started to get serious about retirement, and this line from my very first post is one of my favorite lines ever written:

“This is the story of my journey, told in the Present before it becomes the Past”.  

The Present that I was living at that time has now become the Past, but thanks to this blog the question of “What Was I Thinking?” has been captured for those who are 3 years away from their own retirement.  The biggest question on my mind was to determine when I’d be able to retire.

2-3 Years To Retirement 

At the 2-3 year mark, the question of “What Was I Thinking” is clear as you look at the archives.  I had identified my target retirement date and  I was getting serious about “The Numbers”.  My writing from this timeframe was more focused on the “Hard” topics ($ related).  It’s been interesting to watch the evolution to a higher mix of “Soft” topics as the blog matured, a trend that others have noted in their personal journeys, as well.

If you’re 2-3 years from retirement, it’s time to get serious about the math and determining when you can retire.

18 – 24 Months To Retirement

It’s less than 2 years to retirement, and it’s becoming a “top of mind” issue.  I’m checking the countdown app on my phone more frequently and starting to get serious in my thinking about life after retirement.  The question of “What Was I Thinking” is answered by my posts from this timeframe, which show an increasing awareness of the need to focus beyond the financial considerations.  Taking time to think about what you want your life to be in retirement has been proven to be the key differentiator between those who have a smooth transition and those who struggle with retirement.  It was at this point in time that I started thinking about broader retirement issues, and I would recommend the same approach for everybody following in my footsteps.

1 Year To Retirement

My countdown app is passing the 365-day mark, and each day I go to work is the last time I’ll work on that date.  By this date next year, I’ll be retired!  It’s time to get serious about putting the final pieces into place.  The transition to retirement starts now, and it’s a surprising amount of work to put everything in its place.

The Final Countdown

Retirement is just around the corner, and I’m ready to go.  All of the pieces are in place, and I’m mentally preparing for the huge adjustment that retirement brings.  This adjustment will continue for the next 18 +/- months and is a major focus in my upcoming book.

Retirement – The First Year

The honeymoon has begun!  No more alarm clock, no more commute.  Wipe that smile off your face…or not (hey, you’ve earned the right to smile, this is a huge achievement!).

Retirement – Year 2

The honeymoon is over, and a new transition to the long-term reality of life in retirement has begun.  You’ll find your life changes over the course of retirement, and it’s best to embrace the change.

Which Brings Us To Today

As I write these words (The Present, Before It Becomes The Past), I’m 20 months into retirement.  I had high aspirations for life in retirement, and I’m pleased to report it’s exceeding my wildest expectations.  Life is truly great in retirement, and I sincerely enjoy sharing my journey with you.  I hope your retirement journey is benefiting as a result.

In a few short months, my book will be published.  If you’re interested in the steps you should take to achieve a great retirement, I think you’re going to like it.  My publisher has agreed to let me share a bit of the book with you, and I’ll be giving you some sneak peeks in the next month or so.  It’s been a great project in my 2nd year of retirement, and I look forward to sharing it with you.


I realize that none of us walk the same journey to, and through, retirement.  That said, I think there’s tremendous value in learning from those who have walked this journey before us, and I trust that sharing “What Was I Thinking” as I’ve traveled the retirement path is helpful to those of you who are walking somewhere behind me.  

As for the future, I know not what tomorrow will bring, but I’m enjoying the heck out of the journey.

I’m also enjoying sharing The Present, Before It Becomes The Past. 

I’ll continue to leave some breadcrumbs on the trail…


PS:  A thought struck me at 3:30 am this morning when my (dagnabit) dog scratched on the door to go outside, and I couldn’t get the thought out of my head.  That’s been a more common occurrence now that I’m retired, and I’ve learned to embrace it.   No problem, I don’t have to be at work today (haha), I can catch a nap this afternoon if necessary. The thought was about how I’m leaving footprints on my journey, and how others can benefit if I can just figure out how to leave them a map.

I got out of bed and started writing the words you’ve just read. 

Strange how retirement works. 

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