Top 10 Worst Times To Retire Early (Or Retire Normally)

There are good times to retire early and then there are bad times to retire early. I'd like to highlight the worst times to retire early to prevent you from living a suboptimal life.

As someone who retired in 2012 and mentally un-retired by 2014, I feel it's my duty to share all the landmines I've come across before you step into the minefield. Retirement isn't all lollipops and roses.

To review some of my key findings, please read these posts before or after this post:

Not having to work is nice. However, if you retire at the wrong time, you will experience a lot of fear, doubt, and uncertainty. These feelings will eat away at the pleasantry of early retirement. The uncertainty might get to the point where you wish you had never left a steady paycheck behind.

Ideally, you want to time retirement perfectly so that you get to do everything you want to do with your newfound free-time without having to worry about money.

Please also be aware that the one constant in life is change. The key to a happy retirement is to be dynamic in your thoughts and actions.

The Worst Times To Retire Early

All else being equal, not having to work is better than having to work. However, let's review the top 10 worst times to retire early in order to maximize your overall well-being.

1) During a global pandemic.

Retiring during a global pandemic is absolutely one of the worst times to retire early. If you are a responsible individual, you likely masked up and spent most of your time at home, like the majority of the world's population in 2020 and 2021. Therefore, your life is not much different from regular working people.

Travel is one of the top activities on every early retiree's list. Unfortunately, many borders closed. If you are able to explore a new country, you will likely have to quarantine for 14-days. In China, Taiwan, and Hong Kong, you were literally not allowed to exit your room during the entire quarantine period. In Hawaii, you had to quarantine for 14-days as well or get fined or deported.

With fewer people to see and fewer things to do, you will slowly get bored with your early retirement lifestyle during a pandemic. Having a job will help keep you focused during times of maximum uncertainty.

A job will also make time go by quicker and potentially protect your mental health. Further, you can find jobs where you can work as little as two hours a day and still get paid full time!

With a job, you can only take 2-6 weeks of vacation a year anyway. Therefore, not traveling anywhere will feel more normal. However, if you are an early retiree, not being able to travel feels worse because you get all 52 weeks off.

Finally, if you catch the coronavirus while working, you'll still get paid your salary and receive benefits as you recover.

What went on with us:

Since we couldn't travel like normal, I spent more time writing on Financial Samurai, updating old posts, recording more podcasts, and finding business partnerships that fit with the readership demographic. If I couldn't have as much fun, then I might as well have been more productive. My wife is the CEO of our kids and has more than enough to do.

The problem with doing more business development on Financial Samurai is that it's not enjoyable. Therefore, my plan was to stop looking for business deals once I got the vaccine, once Biden raises taxes, or once there's herd immunity, whichever comes first! I'm exhausted.

During the pandemic, I ended up writing a Wall Street Journal bestseller called Buy This, Not That. I wanted to publish a new book with a major publisher as a way of making lemonade. This way, I can always look back on the pandemic and have something physical to show for the bad times!

I do plan to re-retire sometime in 2024. I've made enough money since the pandemic started to boost passive income to over $350,000 a year for the past three years. In fact, a bear market has boosted my passive income by about 10%.

Related: A Pre-Retirement Checklist For Post-Pandemic Life

2) While you or your spouse is pregnant.

Another terrible time to retire early or retire early is when you or your spouse is expecting.

One of the best benefits of work is parental leave. Obviously, some companies are more generous than others. The time to retire early is not while you or your spouse is pregnant. The time to retire early is after you've taken full advantage of your company's parental leave policy.

At many of the top firms, employees get three months of paid leave a year or more. Therefore, take three months of paid leave, come back for several months, and then retire.

I don't recommend giving your notice the week after fully exhausting your parental leave. If you do, you'll create bitter colleagues and burn bridges.

It's much better to come back to work for at least three months and see how things are. You might love taking a vacation from childcare by going back to work. And you might also find work to be much more meaningful once you have children.

If you plan to have multiple babies, then consider retiring after you have your last child. One of my former colleagues had three babies within five years. She was able to take off nine months plus all her vacation days. She still got promoted to Managing Director and is making big bucks.

What we did:

My wife and I got zero parental leave benefits because we had our children 2-7 years after retiring. If we did have a baby while working, I think at least one of us would have tried to negotiate a severance within 12 months of birth.

I sometimes daydream about what it would be like to get paid three months' salary to take care of my children. Surely, it would feel like a double-win. We are considering having a third kid. If we do, perhaps it is strategically wise for at least one of us to get a job.

3) When your children begin school full-time.

For stay at home or work from home parents, retiring once your kid starts school full-time at age 5 or 6 is a mistake. Unless you plan to home school, you now have 6 – 8 hours of free time to do whatever you want. Therefore, you don't need to retire early.

The time to retire early is during the first five years of your child's life before they go to school full-time. Every single pediatrician and child psychologist believes the first 3-5 years are the most formative years of a child's life. Therefore, spending the most time with your children early on is most important.

What we're doing:

I entertained going back to work in 2022 and 2023 now that our son is in kindergarten and our daughter is going to preschool three times a week. But it's just so hard to go back to the grind. It does seem like more workers have more flexibility and aren't grinding as hard by quiet quitting. In fact, the FIRE movement could be getting obsolete due to all the flexibility. However, having a boss just stinks.

I'm always open to new opportunities, especially since work is more fun if you don't need to work. However, I really like the idea of homeschooling while traveling the world.

For now, I’ve decided to remain a fake retiree and just do my own thing. I will probably publish another personal finance book after Buy This, Not That became an instant Wall Street Journal bestseller. My publisher is offering me another book deal and I’ve taken a pickleball as a hobby. As a result, I don’t want to work full-time anymore for anybody.

4) Near the top of a bull market.

A bull market makes many investors feel like geniuses. The problem with feeling like a genius is that there is a tendency to extrapolate bull market returns well into the future. If you're counting on aggressive return assumptions to fund your retirement lifestyle, you may be sorely disappointed.

Instead of retiring in a bull market, it's much better to retire in a bear market. If you retire in a bear market, your finances will be better stress-tested.

Chances are higher you will be able to stay retired because bear markets tend to last less than two years. If you can survive off your investments when times are bad, you can most certainly survive off your investments when times are great.

Retiring several years after a bear market isn't bad too. Because your memory of devastation is still fresh, you will be more rational and conservative in your investment return assumptions.

In other words, retiring in 2023+ may not be so bad because we've recovered from the 2022 bear market. Therefore, retiring now versus right before the correction is better.

What we did:

I retired in 2012, two and a half years after the stock market bottomed. The economy was still very uncertain, however, my severance package gave me the confidence to leave. Please read How To Engineer Your Layoff, if you want to learn how to negotiate a severance and walk away from a terrible job. It's in its 6th edition.

My wife retired at the beginning of 2015 when the economy was strong and I had found my groove with Financial Samurai. It took her six months to leave because the company agreed to pay her a full-time salary after she negotiated to work for only three days a week.

The bull market seems like it will continue due to an accommodative Federal Reserve and Federal Government. We've got stimulus checks, low mortgage rates, and rebounding corporate earnings. However, if you are planning on retiring soon like me, I would suggest reviewing your asset allocation.

Personally, I decided to take some profits and sell into strength once the S&P 500 breached 4,100 in 2021 and spend it on life. This turned out to be a good move because the S&P 500 declined to about 3488 in 2022. However, the S&P 500 has rebounded again.

5) When you've just taken out massive debt.

Massive debt usually means taking out a mortgage to buy a home. I would not recommend retiring early until you pay off your mortgage or have enough capital to pay off the mortgage if you want to.

Back in 2008 – 2011, the people who were the most mentally distraught were those who lost their jobs and had a mortgage to pay and children to feed. Many of these homeowners not only experienced depression but also lost their homes due to foreclosure or a short-sale.

Fast forward to today, most of these homes have rebounded in price. Many home prices have even far surpassed their 2006-2007 highs.

If you are unlucky and buy a home before the beginning of a multi-year decline in prices, you should at least work for as many years as it takes until your home price gets back to even.

Living in a mortgage-free home feels amazing. If you have a mortgage, knowing that you can easily pay it off if you want to may feel more amazing if your home's value is going up.

What we did:

We took on more debt two years after I retired by buying a fixer-upper in a less expensive neighborhood in San Francisco. I viewed the purchase as a money-making opportunity in addition to changing things up. Then we rented out our larger, more expensive house to boost passive income by ~$4,700 a month.

We weren't willing to pay market rent of $8,000+ a month for our house at the time. Therefore, we figured we might as well rent it out and economize.

In 2020, we decided to take advantage of better real estate deals soon after lockdown. Thankfully, I found a sweet house that would have sold for $250,000+ more than we bought it for if it had listed before the pandemic! Given we have more debt, it's time to work more to pay it off.

6) Before you've worked as many years as you've gone to school.

Most of us will go to school for 13 years, from kindergarten through the twelfth grade. Some of us will add on four years for college. If you work for less than 13-17 years, you may regret never maximizing your education, especially if it is a private school one. You may also regret not maximizing your full work potential.

Thirteen years after high school puts you between 30 – 31 years old. Seventeen years after college puts you between 39 – 41 years old. It certainly seems too young for high school graduates to retire at 30 – 31 years old.

Retiring at 39 – 40 years old as a college graduate is more reasonable as it is close to the ideal retirement age range of 41 – 45.

The people most at risk of retiring too early and feeling lost are those with graduate and doctorate degrees. For these people, retiring early means coming to terms they made an educational mistake as an adult.

The double whammy of making an educational mistake and not fulfilling their work potential could lead to depression.

What we did:

My wife and I worked for 13 years each before retiring. Therefore, we were four years short of the number of years we went to school. Because I went to business school while working, I still only count being in school for 17 years.

I justified my earlier departure because my severance package paid for 5-6 years of normal living expenses. Meanwhile, I had already promised my wife that she could also retire by 35 if everything turned out OK with me. She saw how much happier I was and wanted to join me ASAP.

In retrospect, it would have been best if I had worked for one or two more years. If so, I could have planned my departure even better. Here are some things I'd do different if I could retire again.

7) During a tumultuous relationship that leads to a divorce.

When things are bad at home the virus tends to spread to your work and other relationships. When you're fighting, it's easier to start thinking irrationally.

You start indiscriminately selling all your assets because you're no longer building wealth together. The more you lose, the more your partner loses! You may also start slacking off at work because you no longer care what your colleagues think.

Don't retire early before or right after a divorce. Not only will you not be thinking straight, but you will also likely have to rebuild much of your assets.

What's up with us:

Still going strong since first meeting in college in 1998. Less work stress has made home life better. However, raising kids during a pandemic is zapping our energy away.

One of the great things about meeting in college is that we both had no money. As a result, money has seldom ever been an issue for us because we've been on the same page for so long. If we lost everything, we would certainly feel distraught. However, we were so happy when we had nothing that I'm sure we'd make things work no matter what.

All this said, any marriage takes work. The pandemic has really tested my patience given we're all always at home. I can't wait for California to fully open back up due to herd immunity.

8) Before taking a sabbatical.

Before retiring, I highly encourage you to take a sabbatical, if your company has such a policy. Perhaps taking a month off is all you need to get motivated to work again.

Don't feel guilty about taking a sabbatical either, especially if you don't have kids. Think of a sabbatical as the childless worker's parental leave equalizer.

What we did:

Neither of us took a sabbatical, even though both our companies allowed them. Not taking a sabbatical is one of my biggest regrets. I was with my company for 11 years and could have taken two, 1-3-month long sabbaticals.

It would have been hard for me to take the first sabbatical after five years of work because I would have only been 29. I had recently graduated from business school that was 80% paid for by my company. However, taking a sabbatical before negotiating a severance would have been a no-brainer.

During the sabbatical, I would have received 1-3 months' worth of salary, healthcare benefits, and 401(k) profit sharing. The extra 1-3 months of sabbatical would have also given my severance package a slight boost. Finally, I wouldn't have used five vacation days, which were worth five days of pay.

Taking a sabbatical probably would have extended my work career for at least one, if not two years. As a result, not taking a sabbatical may have cost me as much as $500,000 in net worth.

9) Before getting a big raise and promotion.

It usually takes a certain amount of years before you can be considered for a raise and a promotion. In banking, for example, the promotion cadence is usually every 3 – 5 years once you reach Associate. In other fields, you may be eligible for a promotion every year.

If you are more than 60% of the way there to your next big raise and promotion, I recommend gutting it out until you get it. More than status and money, the biggest reason for staying is to prove to yourself you could do it.

What happened to us:

After three years as a Director (one above VP), I was shooting for Managing Director. After not getting promoted to MD at 33, I realized that it would take me at least another three years to ascend since the head of my desk in NYC wasn't even an MD. Our MD had just been let go, so I had to wait my turn.

I didn't want to wait around, so I plotted my escape. In retrospect, I probably should’ve stayed on for one or two more years to bank more money. Looking back now, I see that retiring at 34 years old was crazy early.

My wife was able to get promoted to the title she wanted before leaving a year later. She had previously been passed over for two guys. She was so mad about getting passed over that she finally came around to the idea of negotiating a severance. But first, she had to get promoted.

Instead of having to wait another year, she got promoted six months later because she demanded one. She chronicled her severance negotiation journey here.

10) When you've become accustomed to telling yourself lies.

One of the worst times to retire is when you've been fooling yourself about your financial health and true desires.

We tell ourselves lies to make bad circumstances seem better. We also tell ourselves lies to help make up for our deficiencies. When it comes to retiring early, the most common deficiency is not having enough passive income to cover living expenses.

As a result, here are some common lies we may tell ourselves:

  • I don't expect medical expenses to be a problem (while ignoring the fact that healthcare costs increase by 8-10% on average a year)
  • I'm OK living extremely frugally (while a spouse or partner works to pay for healthcare and general living expenses so you can live comfortably)
  • I've got enough in my investment accounts. Thus, I don't need to contribute another dollar to take care of my 65-year old-self 30 years from now (while counting on historical rates of returns and disliking your job)
  • I'm happy with what I have (while trying to build a business for the sole purpose of making more money)
  • I'm totally fine with not having kids so we can be more free (while secretly hoping to have someone keep you company when you're old)
  • Everybody else is retiring early, therefore, I deserve to retire early too (while not coming close to putting in your dues)

Lying is a temporary coping mechanism that ultimately hurts you. It is much better to recognize reality and take steps to achieve your goals. There's no need to pretend everything is hunky-dory all the time. Just keep working, saving, investing, and striving towards your goals. We're never going to get everything we want.

What happened with me:

Before retiring, the lie I told myself was that I was happy enough at my job. It paid well and I could eat free Kobe beef if I took clients out for dinner! But my wife told me later on that I would often come home and complain about something that happened at work. I didn't realize how unhappy I was until I left!

The reason why I no longer told anybody I was retired a year after leaving my job was because I felt stupid saying so. It also felt disingenuous because I was spending 2-3 hours a day on Financial Samurai. Once I landed a job as a high school tennis coach, for three months a year, I proudly told anybody who asked that coaching was my job. I longed to assimilate back into the real world.

Although funny enough, as soon as I mentioned online that I was a tennis coach, I got a lot of backlash from the Internet Retirement Police. After the incident, it was fascinating to see the same types of people who judged me online were very similar to the people calling the cops on innocent folks having a BBQ in a park, confronting a resident for decorating his own home wall with chalk, calling the cops on a girl selling cookies on the side walk, and calling the cops on a man birdwatching at a park! I’m not sure what propels people to be so nosy?

The psychology of money and human behavior is a wonder to observe and write about. So many people think that once you do the math, retiring is easy. In fact, running the numbers is the easy part. Living a life that consistently makes you happy is the biggest challenge.

Be Patient With Retirement

So there you have it. These are the top 10 worst times to retire early or retire normally. Don't be in a rush to retire early. There are many worse things in life than working at a job that provides a steady paycheck and healthcare benefits.

Sure, your work might be stressful and your manager might be a two-faced backstabber. However, if you don't have enough investment income to cover your living expenses, you simply cannot retire early comfortably.

If you truly hate your job and don't have enough investment income, make it your mission to find another job. And engineer your layoff while you're at it. The luckiest people are those who've found something they enjoy doing that also pays them money. Nobody retires from a job they love!

I retired from finance after 13 years because I no longer enjoyed the work. But if I could retire all over again I would probably have worked for six more years until age 40. If I did, I would have built more wealth, gotten parental leave, and had less regrets.

I tried to find a new career in tech or at a startup, but couldn't find the right fit. Therefore, all that was left was writing on Financial Samurai. Thankfully, Financial Samurai grew and brings me joy every day.

With a Democrat as President, it has become incrementally better to retire given more financial support from the government. At the end of the day, the best time to retire is when you have enough passive income and you are mentally ready to let go. Once you do, enjoy the ride!

Free Tool To Help You Retire

If you want to retire early, I suggest signing up with Empower. Empower is a free online tool I've used since I retired in 2012. Before Empower, I had to log into eight different systems to track 35 different accounts. Now I can just log into Empower to see how my stock accounts are doing. I can easily track my net worth and spending as well.

Empower's 401(k) Fee Analyzer tool is saving me over $1,700 a year in fees. Finally, there is a fantastic Retirement Planning Calculator to help you manage your financial future. I frequently use the Retirement Planner as a coach to keep me on track. There's no better free tool on the market.

Personal Capital Retirement Planner Free Tool
Empower's Free Retirement Planner

For more nuanced personal finance content, join 65,000+ others and sign up for the free Financial Samurai newsletter. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. To get my posts in your inbox as soon as they are published, sign up here

About The Author

50 thoughts on “Top 10 Worst Times To Retire Early (Or Retire Normally)”

  1. Sam,

    I retired early this year. A pandemic is a great time to retire! Here are three key reasons why:

    – Lower opportunity costs: unless you’re in e-commerce, most businesses and industries are challenged right now, which puts downward pressure on compensation and upward pressure on stress and frustration levels.

    – Tremendous travel bargains, without the crowds. Sure, you have to be selective where you travel, and perhaps globally minded, but this is a historic opportunity to experience some amazing spots in the world, as I am currently doing in Thailand (which has COVID very much under control).

    – Finally, meaningful retirement revolves around multiple passions and not just a single passion such as travel. One should take a portfolio approach to retirement – in having multiple passive income sources, and multiple passions to occupy your time. This markedly reduces the sensitivity to macro factors. For example, this year I wrote a book in addition to experiencing some incredible adventures.

    Happy to share more thoughts on this if that would be helpful.

  2. Interesting post, especially because sometimes people forget there is a retirement element to the FIRE equation.

    All of the above kind of presume that you are going to retire early rather than having a conventional retirement.

  3. Great article! I really appreciate your insights. This blog topic stood out to me because it’s a topic that not many people have talked about. Though, I think it’s a win if you work fewer years than your education years by the time you’ve reached FIRE. That to me means that education has paid off so that you don’t have to work more than you have to.

  4. I like your list and the links to some of your other articles. After reviewing the monthly passive income/costs, will you explain why you don’t just pay off your primary mortgage, reduce expenses and if applicable, reduce insurance requirements. I live in Florida and the insurance is much higher if I have a mortgage so the money I can make on the spread, and more importantly, the emotional component of having a small footprint, no debt freedom and being done isn’t worth the percentage spread I could make being leveraged. I am also wondering if there is nothing left to chase, do you think that would be healthy or not? For me, I am debt free and was planning on traveling abroad and volunteering before the pandemic hit–now I will continue to work from home until things normalize.

    1. Sure. At a mortgage rate of only 2.125% for my primary residence, I feel it’s low enough where I’d rather invest in the stock market and real estate market. I’m bullish on housing in 2021 and beyond. I’ve also got a S&P 500 target price of 3,888 for year-end 2021 as I wrote in a recent newsletter. Therefore, I’m hoping to make more money with risk assets.

      However, I am paying down my vacation property mortgage steadily. I think it’s always good to do both.

      Related: Pay Off Debt Or Invest? Follow FS-DAIR

  5. Excellent read, as per usual. Fascinating insights! And haha, the Karens found you. ‍♀️ Why do people do this?!

  6. Wow the US has some impressive parental leave benefits, are you sure it isnt a socialist country lol. Here in South Africa we generally get 3 months paid leave for moms (extra time taken will be unpaid leave) and 3 days for dads..maybe.. depends if they company is generous lol. Sad case of affairs, but interesting what everyone thinks is normal.

      1. Its unpaid too. Hence it depends on the generosity of the employer. The banks and high end employers are good. Blue collar, yeah not so much.

  7. Point 3 doesn’t make much sense. If your kids are in school, you don’t have that time free unless you are retired. Otherwise you would be at work. If you are retired, you can relax during those hours and have plenty of energy for the kids when they come home.

    Point 6 is a stretch for physicians and PhDs. If I finish school at age 27 or 29, then I’d have to work till 49 or 53 to equal the amount of time schooled thus far since kindergarten. If I made it big, I’d want to get out wayyy before then.

    Agree otherwise with rest of it.

    1. That’s the beauty of everything. What makes sense to me might not make sense to you.

      Retiring at 49-53 or later seems like the minimum for someone with a doctorate. Otherwise, it seems like a waste, unless you just did it for the money.

      Remind me your age and whether you have kids and are retired or not? Thanks

      1. 36 y/o and a 6 month old at home. I became a physician because it was a safe way to earn good money while also caring for others. Job security is always there. That being said if I could retire early, would do it for sure. Maybe do something part time for fun.

        So how does point 3 work out? if your kids go to work and you are working from home, how do you have 6 to 8 hours free?

        1. Cool, so wouldn’t you find it a shame for you to retire before 50 given you just started out?

          For work, it’s about being more efficient with your time. Work from 4am – 8am and then take the rest of the day off. Few really works a full day. Which is why pre-pandemic, few companies allowed workers to work from home most of the time.

          Enjoy your financial journey! I hope you work well past 50!

          1. I see. Our assumptions about home work were different. My wife’s company has decided to go complete work from home for those that do not have to do lab work even after 2021. They have found their people are more productive actually. Also, my wife works straight through the day with meetings and even then continues to work a couple hours after 5 sometimes. Also another assumption was work from 4 to 8AM. My family loves to sleep. We get up at the last minute to feed the baby at 6:45 and go.

            I think working till 50 would be ok if I had a job that I could walk away from everyday and not think about it. Also it would be great if I could take a vacation and not worry about the aftermath. ie, patient’s calling and not being able to contact me, the massive emails when I return. I would love to drop some responsibility in my life and my career would be a start.

            1. Impressive! I only know a few people who work throughout the day at home, and I’ve gotten to know MANY of them since I left in 2012. Your wife’s company is lucky to have her.

  8. I think the general assumption about retirement strategy is all wrong. Work like hell until you don’t have to at all. It’s probably due to the income takeover mindset, first generated by SS, then pensions, and now 401(k)s… all of which require a certain age to benefit. I’m confident I’ll want to do something until I’m 90.

    While I’m still funding my 401(k), once it’s projected to get me from 60-100 years old without any more contributions, I’ll focus on my bridge account (brokerage) until it can supplement the lower-stress, part-time, more-rewarding job that I really want to do.

    Retirement should take place in steps, not off a cliff. We’ll see how this goes.

  9. This post should be used as a checklist for people wanting to retire. The only disagreement I have is retiring during a bull market. Any prudent retirement plan should already be factoring in the possibility of a bear market lasting at least a couple years. If you can’t weather a bear market, you probably shouldn’t be retiring at all.

  10. Hi Sam, I think you have some good points. I retired @44 when my oldest kid started high school. It seemed like my last chance to spend time with them before they head out to college. I think it worked out. It took the kid a while to get used to having me at home after working for the first 14 years of their life.
    I was just talking to my partner about planning for Sabbaticals to make it a more enjoyable journey before they retire.
    However, I don’t think the market cycles had an impact on the timing our plans. We know it will go up and down overtime. I don’t think it makes sense to let that impact your life as you should try to live your best life and plan accordingly.

    1. I’m glad you got to spend more time with your kid and congratulations for your retirement.

      You’re right that it’s more important to choose a certain age to retire rather than a certain time in the market for a certain amount of wealth. Time is more valuable than money.

      However, if someone has a choice in the matter, but I think it’s best to retire in a bear market when your finances are better battle tested than a bull market.

      I look at my own situation this bowl market and think to myself: I think I’m just gonna hustle a little more to take advantage because the good times my end. And when the good times and, I will then take it down and notch and spend more money to increase the good times again.

      1. Interesting perspective, if I’m understanding your reply correctly, it is fascinating to me how different people are motivated in opposite directions. I’m sure that has played a role in the survival of the species.

        I think I’m the opposite, when the market is going up, I feel like I can step back and let it do the work. I was more motivated to work harder and save more during the downturns. We’ll see how I feel in a few years when college tuition bills start showing up.

  11. Frugal Bazooka

    You’re not sure why people are so nosy? It’s because they have too much free time after retiring early! I’m looking forward to the post where you recommend people keep working until they turn 90. That will keep them busy and too tired to complain.

    1. Well, with interest rates falling to 0%, many Americans will have to work forever!

      It’s just that millions of people don’t realize this yet. I hope my proper safe will draw a post has given people some thing to think about.

  12. I retired during the pandemic although I am still working full time from home. I plan on working as long as I am able to work remotely. I use to spend 20 hours a week commuting to work. It is like two weeks vacation per month not having to spend so much time in my car every week.

    I am able to earn my salary without a penalty from Social Security because I reached FRA.
    We are using our extra income to fund our Roth IRAs to the limit and pay down our mortgage.

    We are planning on travelling some after the pandemic ends but we don’t want to travel anywhere we would have to spend 2 weeks quarantined in a hotel room.

    When I have to start taking RMDs from my 401K, we plan on allocating some of those funds into our brokerage account, as there are no RMDs on inherited stocks or bonds for our daughter.

  13. I ‘engineered’ my redundancy at 50 in 2018 (partly inspired by one of your posts on the subject), intent on a FIRE lifestyle. I spent my time up until Feb 2020 getting my wanderlust sated after 30 years of excesive corporate hours.
    After being ‘stuck’ in Asia at the start of the pandemic, Ive now returned to the country of my birth (after 20 years) and have enrolled in a 2 year college course.
    Did I retire in a bull market? Or too close to a pandemic? Was that wrong?
    All I know is I had a detailed spread sheet for 5 years before I left work, and its not turned out that way at all. Who knows if a Black Swan might swim over just as you plan to retire?? But I’m rolling with the punches and still loving the flexibility that giving up work has provided… even if I am about to go into another full lockdown at the end of the week….. there is still so much I can find to fill my time with!

    1. Glad you were able to negotiate a severance and explore the world before the lockdowns!

      I’m prepared for another long lockdown in SF, and our positivity rate is only about 2.5% vs. 15%+ in Texas where there are no lockdowns.

      Thank goodness for the internet!

  14. I really liked your list and don’t see anything I would change. I would add 1 more and that is to not retire until your kids are in university or left the house. Several people I know retired when their kids were still in High School and really couldn’t start their retirement until the kids went off to school. They wanted to travel or move, but couldn’t until their kids were gone. They talked about being bored, and missing work.

    1. Retiring until after the kids have left the house is a great goal. It’s just hard if you want to retire early and are burned out from work. If I had to work for another 17 years stating today, I would be 60. I’d be financially fit…. but I wouldn’t have maximized my life.

      Perhaps homeschooling is a solution to retiring with kids still in the house! I think so.

      1. If you are out of the rat race early I think that is a great solution. I am thinking more about the retiree who stops working in their early 50’s to even late 50’s, but had kids latter in life. It is not uncommon to have a child when you in your 40’s, so people are having teenagers when they are in their late 50’s or even early 60’s. I will be almost 58 by the time our last child is out of high school. Wife and I talked about retiring in our early to mid 50’s, but really have the sending off of the last kid to college as a more realistic date. Retiring to spend 40+ hours a week teaching the last one doesn’t sound like a very fun retirement! Teenage children can be very challenging to you financially and mentally.

    2. But it is a good time to spend that last few years with the kids before they are leaving. We dream about being able to spend 2 months of summer vacation with kids traveling.

      1. A long summer vacation might be a lot of fun. I am more concerned about the other 9 months especially the winter months when you and your spouse want to spend time somewhere warmer, but the children still have school.

  15. Sam
    I just love your posts. I genuinely look forward to your new or revamped material and I’m so thankful we all have you to educate and entertain us during this pandemic. Topic 7- my wife and I also got together in college (1996). In fact, earlier today, I sent her a love note over text, mentioning some key events and places we’d lived, how far we’ve come in the last 20+ years. Having recently bought a new home, Ive been thinking a lot about how our ability to stay happily married has made all the difference. Whether you are talking about building networth or a successful retirement, the importance of avoiding divorce cannot be understated.

  16. Meh, if you have been planning to retire and it’s well thought out, you are not lean FIRE, then go ahead and FIRE. There are plenty of folks on the MMM forum who discussed FIRE’ing this year or in the past few years and mostly you see that they regretted not doing it sooner. There will always be great reasons not to FIRE. The LivingFI blog does a great job of addressing the psychological aspects of retiring early.

    Agree with Sam that if you don’t have enough to support medical care or housing, etc. then it isn’t the wisest choice to quit. I’m planning to quit in 2021 regardless of what the economy looks like b/c our passive income generates 2.5 x expenses and my DS wants to work another year.

    What this site has incorrect is the SWR, 3.5% still seems just fine. I would go with BigERN on that, no offense Sam, just don’t want folks misguided.

    1. Sounds good. You gotta do what’s best for you. I didn’t realize there was a “correct” SWR.

      Hopefully you don’t quit, but negotiate a severance.

      May I ask why you waited so long to retire if your passive income generates 2.5X your expenses?

      1. Hi Sam,
        Life circumstances decreased our expenses, and at the same time we have been purchasing a lot of cash flowing rentals; These increased our passive income very quickly and substantially. Plus I only work 3 hrs a day, and still get full salary, so it’s been really nice and an incentive to stay. My work is overseeing teams helping those suffering mentally or from having lost a loved one to COVID and other mental health issues, so it feels rewarding. The team is also amazing and we’ve been together many years. So will keep feeling it out.

        It’s gov’t job, so severance isn’t an option, but the pension and medical benefits in about 9yrs (50 y/o) will be a great bonus.

        Also, don’t want to get hung up on semantics regarding SWR 3-3.5% is more realistic than .25% (can’t recall if that was as low as was mentioned, but don’t want folks to get discouraged on this), it’s not just Big ERN that mentions this, but also those that I’ve run numbers with often in finance. Can’t tell if you are serious when you mention the lower SWR, I say that with curiosity, not judgement.

        Take care

  17. oof, #10 hits pretty hard

    I’ve noticed that we’re entering a bit of a FIRE skepticism phase after a lot of initial enthusiasm, and my take on it is that a better equilibrium will be reached in the end for society as a whole, but the FIRE movement itself maybe overshot a little bit in one direction and is correcting towards a more sustainable position (not that FIRE is any one thing or one person or one idea, but it just seems to be a trend)

  18. This is totally left field, but I wonder if it’s worth suggesting people not retire shortly after the passing of a partner. I only thought of this because of the mention of the pandemic. Continuing to work could help maintain a certain consistency after such a disruptive tragedy. It might be worth exploring a new meaningful life experience from a place of strength and level thought rather than as a reaction triggered by such an unforeseen event. Just a thought.

    1. Probably right. Having nothing to focus your attention on after a travesty can be really bad. It’s why so many people go back to work after a travesty – to find that comfortable routine again and hold onto reality.

  19. Hi Sam. This post really makes a lot of sense and seems to apply to when making any big decisions in life – don’t make them when you’ve had (or are going to have) a big life change, or are under a lot of stress. If possible, make them when you are in a state of stability – financially, emotionally, physically.
    Take care and stay well!

  20. If only we could visit China – I would be more than willing to spend 14 days locked in a hotel room than deal with the idiots from both parties now running the United States at state and federal levels. Lock downs only work if one follows the Chinese model; partial lock downs are successful in reducing the number of new cases but not stopping new cases.

    1. To be free — to not let the big brother control your life — you have to have self control, you have to believe in common sense, you have to be considerate to others. In short you need to self govern. Lots of people in this country don’t seem to understand that.

  21. I retired Sept 1st (in the middle of the Pandemic). My wife is still working so I guess you could say “semi-retired”. To me, in the end, it was a great time to retire. As I wind down from working we can assess our finances without spending too much (as we can almost do nothing during the pandemic). The stock market appears to be going up now should be for 12-18 months based on past statistics.

    I may start working again but I want to wait until I am bored before I come anywhere close to joining the rat race again. This time, if I do go back, it will be on my terms and something that I love, money would be secondary.

  22. Thanks for such a thorough post! I think most people certainly wonder when the right time is to retire early and don’t think so much about the wrong or worst times to retire early. Thanks for sharing so many valuable insights.

    Good point about not retiring during this insane global pandemic because having 52 weeks off and feeling like you’re stuck and can’t go anywhere would be mind numbing. Like a house elf finally earning his freedom but then ironically not being able to get out of the house. (I have Harry Potter on my brain for some reason)

    Thanks again Sam!

Leave a Comment

Your email address will not be published. Required fields are marked *