A Corporate America Millennial Debates If It’s Possible to Retire Early at Age 55

For years, I had wanted to start a blog. More specifically, a blog in the personal finance field. I was frustrated seeing so many coworkers and friends going into debt at a young age, spending money they didn’t have to impress people they didn’t know. 

Then, in 2011, I realized our family was going down the same path. Though we had a modest mortgage, we had two car payments, $50,000 in student loans, and had just agreed to buy a lake house with family (including the boat and wave runner). The hole we were digging was getting deeper and deeper. 

• When starting this blog in late 2017, FIRE (Financial Independence, Retire Early) was never the goal. The plan was to document our journey (or pilgrimage) to financial independence and hopefully help others. We had already made great progress by 2017 and were finally paying off the mortgage. The blog ended up holding us accountable during the final stretch.

When Can I Retire from Corporate Life? 

I like working. I will probably be one of those people who work in some capacity until the day I die. Working gives me purpose and meaning, and thankfully, I have worked for an organization for 13 years that has provided this to me. 

At the same time, even within a great organization, I had a terrible year that almost led me to quit and find other employment. Thankfully, I stuck it out and could transfer out of that area, but I was pretty miserable for a while. I wouldn’t say I liked going to work, carried stress home with me, and had trouble sleeping at night. 

It reminded me that even at a great organization, things could change on a dime with factors entirely outside of my control. So, pursuing financial independence was never about retiring early; it was about having options. Options to quit a bad job or a lousy boss without losing the home my family lives in. Options to take a lower-paying job may also come with lowered stress levels. And most importantly, options to ensure that I have the flexibility to spend plenty of time with my family no matter my work situation.

Even though my official retirement date will likely be on my deathbed, it seems like a good time to consider a retirement date from corporate life.  

Who knows what the game plan will look like after that? It could include financial coaching, driving for Uber, coaching a high school or college baseball team, investing in real estate, or whatever opportunity. 

The thing is, I don’t want to have the pressure of doing any of these things while having to worry about making a living from them. If I get paid, great, but with a family, I am responsible for taking care of myself and them. So I will not put myself first above what is best for them. What is best for them and me is to continue doing what I’m doing for the foreseeable future.

With all that being said, I’m approaching 40, and the time has come to start thinking about a retirement date. Of course, that doesn’t mean I have to retire at that date, but it is something to work towards. 

Is Retiring at Age 55 Early Retirement?

For me, that magic date is 55 years old.

If that doesn’t sound like an early retirement date, Twitter thinks otherwise, and we all know that Twitter polls are an absolute fact. 🙂

There are a few reasons why this date makes sense.

• Kids Will Be Out of High School: My wife and I often fantasize about being snowbirds during the cold winter months. We love living in St. Louis most of the time. Spring and fall are beautiful around here. Summer means heat and humidity, but we spend much time near water, so it doesn’t bother us. The initial cold around Thanksgiving and Christmas makes the holidays feel like the holidays. But January through about mid-March is awful. It’s cold, the days are short, and there’s nothing to do. We can’t just pack up and move to Florida for three months while the kids are in school. But once they are out of school and hopefully off to college somewhere? You better believe we’ll be out of here. 

• Health Insurance: Nobody works for the same organization for 30 years and then retires nowadays, right? I would love to if it were up to me, assuming I don’t get stuck with a terrible boss or anything. If I can survive the next 16 and a half years, I can get health insurance benefits for life. I understand it because we would have to pay the same amount as an employee, so it’s not free, but excellent insurance at a deep discount. Unfortunately, having good health insurance can be hard to come by in the US if one is retiring before Medicare kicks in.

• We Should Have Enough Money: One surprise after going through this thought exercise was finding out that we are Coast FI. Coast FI is when you have enough saved up to where projected compounding will result in becoming financially independent at some point in the future. Now, this is heavily reliant on future stock market growth. If the stock market takes a huge long-term dive or becomes stagnant, these numbers would look much different. At the same time, it’s encouraging to know that even with a relatively average growth rate of 7%, we would be comfortably FI by 62 and would have nearly enough at 55 years old to where just a little extra income could hold us over. Keep in mind this means never investing another dime when the reality is that I have 15+ years to continue investing, which will make retirement at 55 comfortable. 

In Summary: When Can I Retire?

Combining these three factors seems to make sense to retire at age 55. In addition, my wife, a middle school teacher, would likely be able to bed around the same age. She has six years of retirement as a teacher and will probably return to work in a couple of years when our youngest is in kindergarten.

With all this being said, one of my other sayings is that humans are notoriously bad at predicting what we want to do in five years or more. This is one of the reasons why up until this point, I’ve put almost zero thought into a retirement date. Regardless, it’s good to have some plan, even if that changes. So when can I retire? Who knows, honestly?