Earlier, Longer, Just Right?

It’s hard for folks to decide when to make the jump into retirement, so I was intrigued by a recent question on earlyretirement.org asking folks if they wish they would have retired earlier or worked a bit longer?

About 65 people answered the question and I tallied the results below (taking out a few responses of people who weren’t retired yet) …

– 36% said they should have RETIRED EARLIER

– 8% said they should have WORKED LONGER

– 56% said the retired at the RIGHT TIME

The results aren’t all that surprising when you look at them, I guess.

There’s a sort of “confirmation bias” to people’s decision making that will cause many of them to say what they actually did was the best choice. Many of them had specific reasons why it worked best: they synced up with when their spouse retired, their kids had just finished college, or their job/business had come to an expected end.

Still, it’s meaningful that 4x as many people wish they had retired earlier than worked later. Hardly anyone wanted to work longer. I’m certainly in that group. If I did it all again, I probably would have left about a year earlier than I did. That whole final year I was anxious to get on to my big FIRE adventure. What held me back was the concern that retiring early might equally be the “smartest or stupidest thing I ever did”.

That’s where a lot of people get caught up in the ‘One More Year’ (OMY) cycle. It’s easy to keep working when you are uncertain. OMY can then stretch out to an extra 3-5-7 years. I know a few people caught up in the OMY loop right now.

In our situation, working OMY wouldn’t have changed our financial situation in a significant way as we were already ‘over saved’ for the lifestyle we wanted. Yet, an earlier retirement would have allowed me an extra year to be home when my son was in high school, which I would have enjoyed a great deal. (I skipped out of work to his nearby school activities a lot anyway!)

Are you happy with how you timed your exit from work?

Image Credit: Pixabay

7 thoughts on “Earlier, Longer, Just Right?

  1. I had two milestones for my planned retirement with one being the start of a pension that started on January 1, 2020, and the other trigger was the graduation of my middle son from college which reduced my annual cost greatly. Everything was going as planned and then Covid-19 struck. My wife and I thought to ourselves “we cannot go anywhere anyway, so we might as well work”. So we worked one more year. In retrospect, we would have stuck with our original plan.

    Liked by 1 person

    1. I’ve heard a lot of people say that about COVID – that it kept them working a bit longer. I was happy to be on the sidelines for that. I can only imagine how much work it was to close & reopen business, lay people off, deal with testing/PPE, and remote work. Ugh.

      Liked by 1 person

  2. Lol…I’m the absolute worst at retiring and OMY syndrome!

    I first “semi-retired” from my MegaCorp role in early 2009 (at 44), I got several calls from my former MegaCorp to come back and help with some “special projects”. I reluctantly agreed (after being retired for just 17 months). I agreed to just OMY upon my reluctant return in late 2010… It turned into five (5xOMY) more years! Finally, I said enough…and left for the second time in late 2015 (now at 50). Driving home one afternoon, nearing my final week, another old colleague called and played on my weakness to help, and convinced me to spend just OMY helping him sell a small manufacturing company that he was now running. I agreed to just OMY a second time… Seventeen months later, we sold the company and I finally left “working for a living” for good in April of 2017. So I completely get it! After five years being fully retired, I wish I had just stayed retired in 2010 when MegaCorp first called back and I’d now be celebrating 13 years of retirement this year instead of just 5 years! I’d love to have that time back now. But hey, I’m not complaining. Hind sight is always 20/20!

    Liked by 1 person

    1. Wow – 8 years of putting it off. You were pretty young the first time. Did that play into your thinking to return … ie I’m a bit young to stop working now anyway?


      1. Definitely, was in the back of my mind… Financially, we were fine. I had made several great real estate investments (about 20 units) by that point, that were cash-flowing more than our expenses. Our 401k’s had been maxed out for a very long time and wouldn’t be touched for 15 more years, our house was paid off, colleges were either almost over (or in my youngest’s case, decided and set aside). We could’ve cut the chord and just enjoyed life in 2009. Honestly, I only went back for OMY to qualify for one more REI mortgage (because I’d found another nice multi-family building)! I reasoned to my wife, that I could go back OMY and get the new rental mortgage set up and once it closed (and matured from a cash-flow standpoint) the bank wouldn’t really care. I thought, at that point, the job would no longer matter, so I’d just re-retire…and then I found more properties and…well, here we are a bunch more units later and still looking for the next one! 😉 (…and yes, I was addicted to Monopoly as a kid! My wife and kids still won’t play the game with me!) 😆

        So sorry for the long-winded answer, but I was still very young in 2009, and a little worried that I’d get bored after scrambling up the MegaCorp ladder and jet setting all over the Pharma world for 20 years. I now know, that I would’ve been fine the first time. I have way too many hobbies, and I’ve always found ways to stay busy investing.

        Liked by 1 person

      2. A lot of people worry about boredom. I never really have. As they say, “there are no boring days, just boring people”. I’m definitely not one of them!


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