9 Reasons It’s Difficult To Retire Early

Lano Beach - Savai'i

I had a great day at work this past Friday.  There wasn’t anything especially amazing about it, but it was a truly enjoyable day.  Good conversation, meaty strategic work, and a fair amount of horsing around.  It was the kind of day that makes me say ‘this is fun – why do I really want to retire early from all of this?’  What am I going to do – lay on a beach all day?

While I have been pretty zero-ed in on my FIRE date – the date that I will be both financially independent and retiring early, it’s days like this at the office that have me wondering why I should?  What will I do all day if I’m not driving initiatives within our Megacorp?  After 26 years of work, will I be bored, lazy & unfulfilled?  Should I just say “one more year” for a few years and bank extra $$$?  (I could buy a new sports car, invest in a vacation home, or plan even more extravagant vacations!)

That said, time is the ultimate luxury.  If you don’t need to work, why would you?  Is more money really going to make you happy?  I asked some recently retired (or ready to) friends & acquaintances why they would work “One More Year” if they were financially independent (FI) and could retire early (RE).  Here’s what I heard:

1) “Insurance” in case the financial world falls apart – remember 2008?

2) Nothing urgently prompting me to leave a perfectly good job – that pays well

3) Waiting for pension to be fully vested or healthcare coverage – corporate rules

4) Just plain scared or chickenhearted – don’t 100% trust ny math or financial advisor

5) Waiting for spouse to also be ready to retire – keep our lifestyle in “sync”

6) Worried that they will be bored – couldn’t think of anything better to do

7) Saving up extra resources for retirement travel & luxuries – live like never before

8) Waiting for kids to head off to college / finish college

9) Have a job with travel that they enjoy – spouse can go on trips now kids are in college

In addition to these sentiments, many talked about working “one more year” but already starting to take it easy on the job, enjoying work without need to competing for another promotion, or starting to spending more on toys that they can enjoy in retirement.

Most people have several reasons to work “one more year” – but most of them center on the equation “money > time”.  Especially when one is adjusting for risk.  While I certainly can agree with almost all of them, but I will be a bit disappointed if I pull the “one more year card” myself.    How about you?  How sure are you that you will be able to pull the “RE” card on the first deal?

3 thoughts on “9 Reasons It’s Difficult To Retire Early

  1. Although we are early in the journey, also had been targeting to retire early shortly after achieving financial independence. We been having conversations if we can pull it off. Always afraid that I might get the computations wrong and that we would not be able to sustain it. I know that there is always the option of getting back to work. But still. I can relate to more than half of the reasons for “One More Year.” It is still far but, I think we may have to contemplate these reasons more. Thank you for this reminder!

    Liked by 1 person

    1. At the time I wrote that post (2015), I wasn’t sure if early retirement was going to be the smartest or stupidest thing I had ever done. Now – 5+ years of retirement later – I see it was the smartest. This time has been the happiest in my life by a wide margin. And that’s from someone who’s lived a pretty charmed life!


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