Early Retirement - Some Reflections Two Years In

I retired in 2021 at age 45. I recently passed my two year “retire-a-versary” and over these last couple of years I’ve talked with many other folks who are interested in retiring early. This post is a collection of the thoughts and resources I’ve most often shared and that I’ve found to be the most useful. 

Is it time to retire? 

When I retired, I was at the peak of my earning power. I was making more than I ever had and I also was in high demand from other employers. I was at my most valuable and desirable as an employee, and that can be difficult to walk away from. 

If you’re in this type of situation, it can be helpful to ground yourself in what actually contributes to happiness (hint - it’s not more money). There is quite a lot of science and work in this area - a couple of sources I highly recommend are:

• The Science of Well-Being - Dr. Laurie Santos’ popular online class on well-being (pay special attention to the “hedonic treadmill”). 
• The Art of Happiness Podcast - Arthur Brooks’ podcast where he digs into both the science behind and application of various happiness principles. 

In addition to the science, two pieces of fiction that I find incredibly grounding in this area are:

• Leo Tolstoy’s short story How Much Land Does a Man Need?
• Kazuo Ishiguro’s novel The Remains of the Day

And of course, the old quote “Comparison is the thief of joy”.

Mindset

Retired life is different from working life in many ways. The most significant difference for me has been that I, for the first time in my life, control my time. As a kid, your parents manage your time. In school, it’s governed by teachers and professors. As a worker, your manager controls your time. Even if you’re self-employed, your customers control your time. When you’re retired, every day is a blank slate and you decide how you spend it. 

As great as this is, it’s a significant change. I’ve read many stories of retired folks who become bored quickly or depressed, largely because they’d not given enough attention to this and other changes. One way to think through this - you are not just “retiring from” your career. You are also “retiring to” the rest of your life. So, you need to give this some time and attention!

Another big shift is in your loss of work identity. You’re no longer “Security Engineer” or “Corporate Attorney” or “Head Chef” or whatever your paid role was. To the extent this work identity was a large part of your life, you’ll need to manage through this loss in identity and how it will be replaced by something new.

Two books that I think do a nice job of helping through these and other transitions are:

• Fritz Gilbert’s Keys to a Successful Retirement
• Casey Weade’s Job Optional

For me, I’m really enjoying having the opportunity to spend my time as I see fit. I do a lot of volunteering locally and spend time on hobbies and personal projects. I still enjoy security as a field and intellectual pursuit so I also do some advising, primarily for security startups. And I do some mentoring and coaching for those new to or moving up in the security field, especially folks from underrepresented groups. 

Finances

There are hundreds or thousands of books written about how to finance retirement. I won’t try to recap or summarize - it’s definitely worth exploring and educating yourself even if you’re using a financial advisor. To me, the primary issue was going from earning and accumulating for many years to now drawing that accumulation down. Instead of getting a paycheck from an employer, I’m now paying myself. 

A few of the resources I found particularly helpful:

• Financial Independence Subreddit - A large and active community focused specifically on the various considerations associated with retiring early. Lots of smart financial and life advice to be found here - check the FAQ to get started. 
• Bogleheads Forum - Large and well-established community centered around the investing principles inspired by John Bogle (founder of Vanguard). 
• Morningstar - Lots of helpful articles - note that your financial provider(s) of choice also likely have useful educational resources available online. 

I hope this post and references are useful, and I wish you good fortune on your journey!