Do I Wish I’d Worked One More Year?

With all of the volatility in the market, should you delay retirement by a year? A viewer asked Jason if he would feel more secure had he worked another year or two before retiring early. In today’s episode, Eric + Jason discuss that question and the merits of considering “one more year”. Join us as we discuss this idea and the reasons you might consider that option, what Jason would have missed out on if he had worked longer, and the value he found in retiring when he did.

Show notes may be found below the video

Show Notes

Essential Background:

  • For context on what Jason has been up to since retiring early in June of 2020, don’t miss our episodes discussing his early retirement milestones. The first, What I Learned in My First Year of Retirement is foundational to understanding his RE experience. Not everything went smoothly as you might expect. Here Jason discusses what’s changed, what’s been better, what’s worse, and – importantly – has it lived up to his expectations.
  • A few months ago we published a year two update titled My New Life: Two Years After Early Retirement. In this episode, Eric traveled to California to shadow Jason and find out what his FIRE life is like nearly two years into early retirement. We learn how Jason fills his days, hear his concerns pre- and post-FI, discuss the merits of part-time “fun” jobs, and the reality of finances. It’s interesting to compare this video to the one-year milestone for sure!
  • In today’s episode, Jason talked about his long (five weeks, not seven – he misspoke!) family vacation as one of the most important things that happened since retiring early. Jason discussed this trip as a part of How We Travel: Pre + Post Financial Independence. In this video, Eric + Jason compare notes from their two respective sides of FI and their recent vacations: 7 days for Pre-FI Eric and 5 weeks for Post-FI Jason.
  • Many people claim they’ve achieved financial independence (FI) yet they fall prey to repeated “one more year” extensions. In our experience, this is often due to a lack of confidence in their financial strategy. In Have Enough to Retire (Early)? 10 Steps to Make Sure we discuss ways you can prepare for this key decision, and proceed with confidence.

Jason’s milestones blog posts are perhaps the easiest way to understand what his journey has been like since retiring early. In these articles, he discusses candidly what he’s felt, experienced, and achieved in the two years since he left his career behind. As he + Eric talked about in today’s episode, it’s almost inconceivable for him to imagine not having had these experiences. If there’s a specific topic you’re seeking, don’t miss this list of all his blog posts to date.

The One More Year Syndrome is a blog post is a post by Fritz Gilbert from Retirement Manifesto. In this article, Fritz discussed why “one more year” made perfect sense for him. Perhaps just as interestingly, this post also collects the thoughts of many other familiar voices from the FIRE community on this topic. It’s definitely a worthwhile read. On a related note, if you haven’t seen our interview with Fritz, be sure to check out Retirement Is Nothing Like I Thought It Would Be. It’s one of our most popular episodes to date for good reason!

You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.