The Weekend Retirement Test Drive: Groundhog Day and the Rest of Your Life (Plus: Competition)


Don’t be a groundhog [yes, I know this is a hedgehog, but I liked the shot]. (Photo: Anxious223)

There are a lot of rich and depressed groundhogs.

This is a critical concept, so let me introduce it with an e-mail I received from a reader and executive at a Fortune 500 company a few hours ago, edited for length:

So I was out snowshoeing this morning and found myself completely taken in this moment thinking I was like the Snow Queen from Hans Christian Andersen’s fairy tale and that I was walking through the Black Forest. And I was there, at least in my mind, which, really, is all that matters. …Here’s how this is relevant to you – the problem most people are going to have with your book is that these people don’t know how to dream. I think your book is like the 2nd in a series… unless you can find moments of the sublime in whatever present moment, and unless you can dream about creating the next one, what does it really matter how much time you free up from work?

Here’s how we make this e-mail hit home for you and get you $720 in the process:

1) On a scale of 1-10, 10 being best, how life-changing or personally fulfilling have the last two weekends been?

2) Is retirement from the 9-5, 50-weeks-per-year routine one of your current goals? (Yes/No)

3) How confident are you on a scale of 1-10, 10 being best, in your ability to fill 20-40 years of retirement, whether in one stretch or spread out as mini-retirements?

If your answer to 2 is affirmative, here are two worst-case scenarios…

-The answer for 3 is low.
-The answer for 3 is greater than your answer for 1.

In both cases, there will be a serious depression in your future if you create time abundance without the skill and practice needed to fill that void, not to mention regret for having followed the “deferred-life plan” of slave-save-retire (if you choose that versus lifestyle design and its present-tense options).

The next 48 hours of your life — or this weekend — is a microcosm of your potential retirement. How you spend this time is reflective of how you would fill time once you cash in your chips for the good life after 10-30 years of accumulating capital and assets.

Tomorrow is Groundhog Day here in the US, and I want you to make the next 48 hours the opposite of the repetitive rinse-repeat life I associate with the classic movie of the same name.

Here’s the challenge and competition.

Pretend like the next 48 hours are the first 48 hours of your emancipation — you’ve done it and now all of your time is free time.

Prove to us and yourself that you can fill the void with something worthwhile. This could be one of the most telling experiments of your life, so I encourage you to treat it as a required exercise.

If you can’t fill the time, there are questions you need to ask and skills you need to develop before focusing 100% on finances, investments, nest eggs, etc.

Put your real “filling the void” experiment results in the comments of this post. Proof of some type (links to photos, video, etc.) is ideal but not required.

The best comment posted no later than 5pm PST on Friday, Feb 8th will win 36 copies of The 4-Hour Workweek from the original limited 1st print run. It’s now in it’s 29th printing and 36 new copies are worth $720 at retail. These 1st-edition versions are collector’s items and worth more with signatures, which 12 will have :) First-edition original manuscripts have sold for upwards of $1,500 each on Ebay.


I’ll send you a collector’s edition talking action figure of Shaun from one of my favorite movies of all-time, Shaun of the Dead:

If this doesn’t motivate you to action, I don’t know what will.

Here are some links that might help:

E-mail Free Fridays and How to Save Your Weekend [Read the comments of this post and the one before it for ideas]
The Top 5 Reasons to Be a Jack of All Trades
How to Learn (But Not Master) Any Language in 1 Hour
A Beginner’s Guide: How to Rent Your Ideas to Fortune 500 Companies
Lack of Seriousness – The Last Interview with Vonnegut
The Magic of Groundhog Day

Good luck and remember — Subtracting work and the office doesn’t automatically create life. That’s the most neglected and important art of all.

Think big and do the uncommon.

Posted on: February 1, 2008.

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154 comments on “The Weekend Retirement Test Drive: Groundhog Day and the Rest of Your Life (Plus: Competition)

  1. Pingback: rhino video games
  2. “Who is willing to participate in making this day extraordinary or, at the very least, have a funny story to tell all your friends?” This was my opener for leading rounds of row, row, row your boat on BART trains.

    Having recently read this blog, I thought, no reason to wait until the next Groundhog Day. Why not tomorrow? I pitched my idea to two friends. One said, “I have a hard time believing people will sing on a BART train.” Pause. Would I quit? No. I was invested. I committed to doing it with or without my friends. I replied, “Of course they will! I am confident!!”

    My objective was simple: play at 1000% and invite others to join in. These are a few of our highlights.

    I was inspired to discover at least one person on every train was an enthusiastic supporter and encouraged us. Note to self: excellent screening method for potential friends.

    Inside the Ferry Building, we sat down to play patty-cake. Side-splitting laughter guaranteed.

    Outside I asked two men enjoying the swing music if they danced. “Not in public” they replied. Men, listen up: when a hot woman asks you to dance, say yes!

    Observation: no one questioned these two girls or looked at them oddly. At what point did I start telling myself I was too old for the monkey bars?

    At the park it was somersault races and Red Light, Green Light. Look – our little playgroup that could gained critical mass.

    The delight topper: Derek tickled one of my feet while Jas sucked on the toes of my other. Half of my body moaned and melted while the other half jerked and squirmed.

    Oops – need an email address to share my snapfish photo album. Readers *insert imagination here*


  3. Boredom has more to do with *what* you’re doing, not so much *how much* you’re doing. My days are usually fairly busy without a lot of extra time. But, I am so bored because it’s always the same old stuff. And after a while that leads to a sense of ennui (dissatisfaction through boredom) then to depression and the downward spiral continues if you’re prone to depression.


  4. Tim,
    I know this was posted way back well no so long anyway… But I guess, I also want to say that I really want to fill in the void. I don’t want to end up like all empty and lonely. So maybe for now, I’d start by going out more often and doing worthwhile for the community and for the pets too. :D
    Anyway, I’m thinking of getting involved in a charity for animals. I can see they are getting less and less value as time pass, especially dogs. I love dogs a lot and I have one although I don’t know what breed he is.