If I Could Retire All Over Again These Are The Things I’d Do Differently

I can’t believe I’ve been writing about early retirement since 2009. The first three years of Financial Samurai was me mainly trying to figure out how to retire early. The subsequent years has been me touching upon various aspects of post-retirement life.

For the most part, early retirement has been everything I hoped for. Freedom is priceless. But I’ve also highlighted a lot of negatives that I could not have expected until living as an early retiree for several years.

We can pontificate all we want about what it’s like to do something or be in a particular scenario. But until you experience it for yourself, there’s no amount of planning that can prepare you for some of life’s big moments.

Now that I’m deep into early retirement, I’d like to share what I’d do differently if I could rewind time and go back to when I first left work in 2012.

Things I’d Change If I Could Do My Retirement Differently

1) Work at least one more year. In 2013, I wrote about the trap of the one more year syndrome where people can’t leave their jobs due to the money and security it provides. It’s always one more year to see if you can get a promotion or one more bonus to feel more secure financially that locks people in.

I left work at 34 years old. Now that I’m almost 42 years old, I look back and think how absurdly young that was to retire. Leaving a good job at that age now seems irresponsible and reckless.

I left because I was sick of office politics, bored with my job, and wanted to do something new. These reasons all sound like I was an entitled, impatient brat. Suck it up already, I may have told my younger self. But in my defense, I had already been with my firm for 11 consecutive years.

Working for one more year would have given me more time to prepare for my post-work future.

I would have lived like a pauper my final year and saved another $100,000+ for retirement. On my firm’s dime, I would have gone on more international business trips, taken out for lunch or drinks all my colleagues, competitors, and clients I had gotten to know over my 13 years in the business, and generally savor my final year at work.

Instead, I now feel like I rushed my departure. I only came up with the concept of negotiating a severance in November 2011, five months before I ultimately did. Therefore, I made some mistakes like taking a week of vacation the year I left. This action ultimately resulted in me…

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