A Pre-Retirement Checklist For Post-Pandemic Life

Going through a pre-retirement checklist to prepare for post-pandemic life is a smart move. Like packing for a long trip, it’s easy to forget something you may end up regretting not bringing without such a checklist. Personally, I'm planning on re-retiring soon, hence the reason why I wrote this post.

Retiring from a job after years or decades of work is a scary proposition. This fear is one of the reasons why retirement researchers who feel confident about their safe withdrawal rate assumptions still won't retire. It is much easier to pontificate about retirement when you are still gainfully employed.

One of the top 10 worst times to retire is during a pandemic. With so many things shut down, spending all your days at home doesn't sound like a great retirement at all. There are only so many books you can read, Netflix shows to watch, and meals to have with your family before a deep sense of dissatisfaction begins to seep through your veins.

The decline in mental health is a HUGE issue that is currently being underreported. The rise of clinical depression is no joke. Please be more empathetic to everyone during this time.

People who have little-to-no money worries are getting divorced. Normally peaceful retirees have taken to social media to wage jihad against others they don't know. When there are few release outlets, there is a tendency for people to manifest the worst version of themselves. Prolonged isolation can be dangerous.

The Importance Of A Pre-Retirement Checklist

With global economies fully opening up, massive pent-up demand will be released by people who want to change their lives for the better. Some will try to smartly negotiate a severance and find a more meaningful job. Others may decide to take a long-deserved break. While others might want to retire, hence, my pre-retirement checklist.

A pre-retirement checklist is there to help you minimize regret and maximize happiness. Regret is probably one of the most annoying things a person can experience. And, if you later realize you could have eliminated your regret by just listening to someone, your regret will grow even more!

I've tried to address some of my regret in the post, If I Could Retire All Over Again, These Are The Things I'd Do Differently. I clearly understand I cannot force anybody to listen to me, so I do not try. Experience is the best teacher of all things. Most people need to figure things out for themselves.

When you've been online since 2009, it is fascinating to see how some former doubters have come around. In 2009, they may have been know-it-all 28-year-olds. Today, they are seasoned 40-year-olds with more perspective.

A pre-retirement checklist helps counteract against the following regrets:

  • An unfulfilling career / not achieving your career potential
  • Not making as much as you could have
  • Feeling like a loser
  • Not properly planning for what's next in life
  • Embarrassment and having to go back to work with your tail between your legs
  • Losing your health

My Intense Desire To Re-Retire

With travel discouraged and a new baby born in December 2019, I decided to really “go back to work” once the pandemic hit in 2020. I figured, if our freedom was going to be restricted for an indefinite time period, I might as well make more money online to support my family.

I went from spending on average a leisurely 20 hours a week writing on Financial Samurai in 2018, to 30 hours in 2019, to 40 hours in 2020 and 2021. The additional time was spent updating old content, writing more articles, publishing more newsletters, writing guest posts, and negotiating business development deals.

The work was kind of rewarding for the first six months. Over 1,000 posts had not been updated in years so it felt satisfying to revisit them all. Further, there was a lot of low-hanging monetization fruit. However, as time went on, my dissatisfaction with work grew.

I slowly became resentful of our politicians who seemed to live by different rules. I became angry at the virus for taking away people's lives too soon. It became annoying to have to compete with other bloggers and media sites with a huge writing staff for search traffic. Further, I noticed a rage grow online as social media became a main way to vent.

I just wanted to write. It is what I've been doing on Financial Samurai since 2009.

The time I spent updating Financial Samurai in 2019-2021 should be enough to last at least three years with periodic light maintenance. The relationships I've built with new and old business partners should hopefully last for another five years or more. Therefore, I'm anxious to review my pre-retirement checklist and move on to a new stage of life.

Things To Do Before You Retire Post-Pandemic

Like many of you, I'm excited to return to normal life. Therefore, let me share with you my pre-retirement checklist I'm going through to be ready for the next stage.

1) Make Sure You Have The Proper Asset Allocation

In early April 2021, I realized something was very off with my asset allocation of stocks and bonds. For at least three months until then, all I could think about was retiring again. However, roughly 85% of my net worth was invested in risk assets like stocks, real estate, venture capital, and venture debt.

If I was truly going to retire and give up a steady amount of active income, it would be unwise to have such an aggressive net worth composition. Therefore, once the S&P 500 breached 4,100 and the 10-year bond yield breached 1.7%, I decided to rebalance.

My original maximum exposure to equities as part of my net worth was 30%. But I had let equities grow to ~35% after a huge 2020 and a strong 2021 YTD. Therefore, I sold some stock in my tax-advantageous accounts to reduce equites to roughly 32% of my net worth. I plan to continue selling if the stock market keeps going up until equities account for no more than 25% of my net worth.

Your age matters less than the stage you are at in your financial journey. Despite being 45, I should be investing closer to someone in his 60s. I have enough money, which is why I want to re-retire. If I didn't have enough money, I would keep on going!

The best free tool to track your net worth and calculate your retirement cash flow needs is by Personal Capital. I've used Personal Capital since 2012 to help optimize my finances and couldn't be happier.

Personal Capital Retirement Planner Free Tool
Personal Capital's Free Retirement Planner: Is your retirement cash flow on track?

2) Make Sure You Have Done Everything You've Wanted To Do

To minimize regret, use your remaining time at work to try and do everything professionally you've wanted to do. Maybe you've always wanted to work in a satellite office. Or maybe you always wanted to propose and lead a new initiative. Now is the time to do it.

If you don't do everything you've wanted to do, you will be forever left wondering what could have been. In my case, I always wanted to work in Asia. I spent 13 years growing up in various Asian countries. But I never got to experience working life in Asia. As a result, I regret not pushing for a reassignment.

Another thing I regret is not taking a sabbatical. I was allowed a two-month paid sabbatical every five years of work and I worked at my old firm for 11 years. What a waste of an opportunity to recharge the batteries!

My final regret was not having a nice retirement send-off. I had bungled my last week of work by accidentally sending a 5-year-old e-mail containing client data to my personal e-mail account. As a result, I wasn't able to say goodbye on my last day of work until HR decided my punishment. Not having a nice closure felt off. Thankfully, HR came to their senses given I was leaving the industry for good.

3) Live Off Your Passive Investment Income

Having enough passive income is key to living a comfortable retirement life. If you don't have enough after-tax passive income to cover your desired living expenses, you won't be able to rest easy post-work.

You could make your spouse work longer so you can relax more. But not having a companion who is equally as free during retirement is not as fun. Alternatively, you might try and do everything possible to make money in different ways.

There are some folks who try to retire early with less than $1 million or have no lifetime pension. As a result, they seem to have more anxiety. Their anxiety manifests itself by always sharing how great their lives are online to help ease their worries. Any astute observer of the human condition can notice these habits. Further, anxiety can often lead to anger and jealousy.

It's important to test-drive living off your after-tax passive income for at least 3-6 months. During this period, make sure you are keenly aware of how you are feeling. The income you earn from your day job should be 100% saved or invested so you can't cheat.

Passive income has various levels of reliability. For example, quarterly dividend stock income and monthly rental income are usually very reliable. However, private equity income is much harder to calculate. Therefore, you should ideally be able to have your basic needs covered by reliable passive income. The less reliable income can be used to cover your wants.

In our case, we've lived off between 70% – 95% of our after-tax passive income since 2012. Therefore, we should be good to go with this item of the pre-retirement checklist.

Related: The Importance Of Properly Forecasting Your Passive Income Streams

4) Have A Specific Retirement Date Or Month

It's harder to get motivated to retire if you don't have a specific retirement date in mind. Your retirement date doesn't have to be set in stone as things always come up. However, having a specific retirement date will force you to appreciate your remaining work time left and take action.

The ideal retirement date is likely 1-2 years away. This way, you have enough time to plan, experiment, and really test things out.

Do you remember getting accepted into college during high school senior year? The time between getting the acceptance letter and graduating high school was amazing. Suddenly, all your stress went away. Grades didn't matter anymore. That's what having a retirement date is like.

In my case, I only had about three months to plan for retirement. I had come up with negotiating a severance in October 2011 and I negotiated my severance package at the beginning of February 2012. From there, I was gone by May 1, 2012. It felt a little bit rushed by about three months.

I would have loved to have stayed for three more months. During this time, I would have taken out all my SF colleagues for a meal, flown to NYC to say goodbye to other colleagues, and spent more time with all the clients I had gotten to know since 1999.

My original retirement date had been the summer of 2017, just after I had turned 40. However, the Global Financial Crisis disrupted my plans. Therefore, maybe I was more prepared than I thought.

5) Make Sure You Know What You Plan To Do After Retiring

Out of all the items on the pre-retirement checklist, having something to do might be the most neglected item of them all. Before retiring, you must really think things through. You can't just say you will be traveling the world, writing the next great novel, or playing golf every day. Specific dates and deadlines should be made.

Take for example my friend Bob. He retired after 20-years in the money management business. The money management business is where a lot of rich men work and pretend to be middle class. Because we had discussed for at least a year what he planned to do post-retirement, he was prepared. This is what he did.

  • He rented out an office with four of his close buddies. He would walk to the office which is close by every morning to manage his family's money. The office gave him purpose as well as friends he could hang out with. He still does this.
  • Bob took up golf to be closer to his son who loves golf. Now he gets to spend a good 4-5 hours of quality time with his son every other weekend. Further, when they go on vacation, they share a common bond of finding spots with great golf courses.
  • He still plays tennis with me and other friends. Once a week, he has a doubles lesson with three of his friends. This provides camaraderie, fun, and learning.

Bob has a great setup. Going in on a small office with his buddies has been key for his mental health and happiness.

If you don't have a specific plan for what you will do post-retirement, I promise you will feel lost. You will also increase your chances of getting depressed. Finally, you may start frequently wondering what's the meaning of life.

Related: The Negatives Of Early Retirement Nobody Likes Talking About

6) Refinance All Your Debt Before Leaving Your Day Job

Once you lose your W2 income, you become dead to banks. It takes at least two years of freelance income that's at least 20% higher than your previous salary for banks to give you a chance again. Therefore, please refinance your primary residence and rental properties before leaving your job.

If you unfortunately have credit card and auto loans, see if you can get your interest rate down as well. Currently, there is still a student loan moratorium. Student loan borrowers are waiting to see if President Biden will forgive $10,000+ in student loan debt. Therefore, it's best to sit tight.

I’m good to go with all my refinances. After taking out a sizable mortgage in 2020 at 2.125% for a 7/1 ARM, I don't plan to take on more debt. Although, I encourage everyone to take a look at a 15-year mortgage. The average 15-year mortgage rate is significantly below the average 5/1 ARM.

Check the latest mortgage rates online with Credible, my favorite mortgage lending marketplace. You can get free, no-obligation quotes in minutes. The more lenders compete for your business, the lower the rate you tend to get.

7) Make Sure You Pay All Outstanding Corporate Debt

If you so happen to have a corporate card, make sure you utilize all the rewards points before your company shuts it off. I had thousands of dollars worth of rewards points that I forgot to use before leaving. Thankfully, I called in time before they shut my card down.

Further, make sure you pay all outstanding corporate card balances and any other debt to your employer. You don't want to have some random outstanding debt come to haunt you years from now in retirement. Expense reimbursements must be submitted and paid before you leave.

8) Find Closure With All Your Outstanding Issues

Whenever you move on to the next stage of you life, you want to have good closure. After so many years of working, you will undoubtedly have made some enemies with colleagues, clients, and competitors. If you retire without proper closure, you may forever feel unsettled.

Therefore, make a list of people you want to make amends with. In industries like big law, management consulting, banking, and big tech, much of the conflict usually arises from hyper-competition.

Everyone is jockeying to work endless hours to get that raise and almighty promotion. If folks compete hard enough, maybe they will one day achieve a top 1% income! Too bad it won't make them any happier.

Once you've decided to exit the battlefield, make amends. Your soul will thank you as you focus on doing something more meaningful.

9) Make Sure You And Your Partner Are On The Same Page

If you are fortunate enough to have a life partner, it's important to share you post-retirement plans. Ideally, both of you are on board with retiring. And both of you share with each other specific activities you want to do once work ends. The last thing you want is to force your post-work activities onto your partner.

You don't have to have all your activities and desires line up perfectly. But you do need to communicate clearly about your respective plans. Going from spending 3-4 hours a day with each other to 12 hours a day can be too much to handle for some couples.

I try to get out of the house as much as possible tennis, exercise, and hikes. It's much harder for me to stay inside for long periods of time. The desire for fresh air and sunshine is one of the reasons why I bought a house with decks. I love to be able to step outside and take a break every day.

Divorce is not unusual for people who achieve FIRE. I spoke to a couple bloggers who decided to “upgrade” or “break free” from their wives once they had enough money. Communication, appreciation, and empathy are key!

10) Understand Your Social Security benefits.

If you haven't logged into the ssa.gov website to figure out your Social Security benefits, do so before you retire. The earliest you're able to collect Social Security benefits is 62. For the average person in average-to-good health, I believe the best age to take Social Security is at age 66, considered the full retirement age.

If you are retiring well before you are eligible to take Social Security, then consider creating a Social Security Bridge fund to hold you over until you are eligible to collect. The fund should consist of conservative investments from which to draw from. But if you have a sizable 401k or IRA plan or have passive income, a bridge fund isn't necessary.

Ideally, after reading Financial Samurai for so long, you will have never relied on Social Security to live a comfortable retirement life. Instead, you will see Social Security as a bonus.

11) Investigate The Best States for Retirement

Finally, given you are going to retire, you might as well do research on the states with the lowest tax rates and the highest quality of living. Without a job tethering you down, you are free to relocate anywhere in America or even the world.

In my best states for retirement analysis, I ranked the states with the most millionaires and the most favorable tax rates. The idea is that millionaires (and billionaires) want the best lifestyles and have the ability to relocate. The rankings are below. However, I still think Hawaii is the best state to retire to.

Best states to retire in

12) Make Sure Your Life Insurance Needs Are Squared Away

The final item on my pre-retirement checklist is to make sure you have the appropriate amount of life insurance. Many employers offer employer-sponsored life insurance plans for free based on a multiple of your salary. I had free life insurance equal to 3X my salary, but I paid extra to receive 5X my salary in coverage.

Once you retire, your employer-sponsored life insurance benefit goes away. Therefore, it's important to make sure your life insurance coverage is still appropriate post retirement. This is especially true if you still have debt and dependents.

My favorite place to check for tailored, no-obligation life insurance quotes is PolicyGenius. PolicyGenius helped my wife double her life insurance coverage to match mine for less money during the pandemic.

Before the pandemic, it never occurred to us to get the same amount of coverage. But as parents with equal responsibility for both childcare and our online business, it only made sense.

Here's how my wife doubled her life insurance coverage for less.

Social Security collection plunges during COVID-19

13) Read The Best-Selling Retirement Planning Book

Before you retire, purchase a hard copy of my new book, Buy This, Not That: How To Spend Your Way To Wealth And Freedom. The book is jam packed with unique strategies to help you build your fortune while living your best life. 

Buy This, Not That is a #1 new release and #1 best seller on Amazon. By the time you finish BTNT you will gain at least 100X more value than its cost. After spending 30 years working in finance, writing about finance, and studying finance, I'm certain Buy This, Not That will help you retire sooner than later.

Buy This Not That Book Best Seller On Amazon

My Plans Post-Pandemic Retirement Plans

My retirement date is once there is herd immunity in America (70%+ vaccinated plus infected) or once income taxes goes up, whichever comes first. Currently, President Biden is targeting raising the capital gains tax rate, the top marginal income tax rate, and eliminating the stepped-up basis to fund his American Families Plan.

I'm assuming one or both of these things will happen within 12 months. With California set to fully open up on June 15, 2021, I'm excited to get most of my freedom back. Thank goodness we made it!

In retirement, I still plan to write, but not as often. Perhaps I will go from three posts a week to two posts or one post a week. Instead of publishing a newsletter every week, maybe I'll go to a bi-weekly cadence. Back in 2018, I was publishing more like once a month.

My primary goal is to get back down to an enjoyable 20 hours of writing on Financial Samurai a week. I believe 2-3 hours of creative work a day is the ideal amount for my happiness. 1-2 hours in the morning and 1-2 hours in the evening. Perfect. Therefore, I may hire a staff writer who can also act as an editorial manager.

A Similar, Less Stressful Life

The reality is, nothing much will change for me in retirement. As a parent of two young children, we won't be traveling internationally for at least a couple more years. Kids don't remember much under 5 anyway. I'm still going to be playing tennis 3X a week and softball once a week on average.

What I'm excited about is getting more involved in my son's education when he attends Mandarin immersion school this Fall. My goal is to re-learn Mandarin from the beginning with him. It'll be fun! Let's hope he's a good student and gets motivated by his dad wanting to learn as well.

I also plan to work on my mental and physical health by getting a trainer. My mental and physical health has probably deteriorated by 10% during the pandemic.

I'm hopeful that by reducing my time spent on Financial Samurai by 20 hours a week, my mental health will improve. Surely, herd immunity and returning to normalcy should improve all of our mental health as well. Finally, I'm confident I can lose 5-7 pounds and get down to my fighting weight of 163-165 pounds.

A strong mind-body connection is integral for living a happy and fulfilling life. May we all find that balance once again!

Recapping My Target Retirement Dates

June 15, 2021 – California fully opens. We made it! I now plan to take things down by at least 25% and go on a two-month sabbatical starting on July 1, 2021. Between writing and childcare, I have not taken a real break since April 2017. So far, the sabbatical has been nice. But it has taken my two weeks to get used to downshifting.

August 25, 2021 – When my son started going back to preschool. With six more hours a day, my wife and I can relax more. That said, we can't relax too much since we still have a daughter to care for! But it will be nice to spend more quality time with her at the science museum and at various parks like we did with our son. Yay! He’s safely in preschool now and loving it.

July 19, 2022 – I plan to retire after my book, Buy This, Not That: How To Spend Your Way To Wealth And Freedom is launched. I'll do some marketing and talks, but after that, it's back to retirement life!

The Three Main Levels Of Financial Independence

A Pre-Mortem Checklist For Bad Things

Readers, what is on your pre-retirement checklist? Anybody decide to come out of retirement during the pandemic like me? How do you plan to retire properly again? A Pre-Retirement Checklist For Post-Pandemic Life is a Financial Samurai original post.

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55 thoughts on “A Pre-Retirement Checklist For Post-Pandemic Life”

  1. Every once in a while we come across an article/piece that is and will be so valuable that we must keep it. This is exactly that pure gold piece of work that I plan to re-visit often as my guiding light. Thank you so much for this one!

  2. Sam, have you ever addressed retirement pensions and how to best select the survivor benefit that best fits the needs of different couples? Example; If both couples have pensions do they select the “self only” payment or the 50% option, or the 75% option?
    If they have $2,000,000 in savings which option is best for that type couple if only one will have a pension when they retire? There are almost no articles out there (that I can find) that breaks it down into understandable charts the way some of your article do. If you’ve not addressed this financial issues perhaps it can be added to your “list of future articles”.
    Love reading your articles!!!!!!!!!!

  3. Another item to add on the checklist for me is “ensure that I have extra money to support my elderly parents”. I am from an African country and the majority of people don’t have a pension or any kind of social safety net, and so I have to support my parents in every way. I put them on a ‘salary’ which I send every month. I pay for at least 90% of their health needs as at private hospitals as government hospitals are not good. My brother used to support them also but his business has not been doing well for the past three years, so everything now falls on me. Sometimes I wonder how my financial life would have been if my parents were financially well off. I think I would have been able to retire early and have more investments, but I am grateful that I am able to provide them with a very comfortable life. My heart broke a week ago when my brother said my parents may have been deceased if I didn’t support them. Again I am grateful that my brother and I have been able to support them so far.

  4. When people took sabbaticals at your old company, did you feel like higher ups gave the ones who took a sabbatical an uneasy look? Two months is a very long time, no matter how long your tenure is and while that seems like a really nice perk, was it similar to those unlimited PTO models that was basically “yeah, we have this great benefit, but if you really take more than 15 days a year, we’re going to keep track and remember come bonus/review season”?

    I should probably check if my company offers a sabbatical. I was looking into early retirement as an option but a 2 month sabbatical (even if unpaid) is a phenomenal benefit that would not make me want to quit at all.

    1. Yes, the funny look from upper management and a potential decrease in bonus kept me and most others skipping the sabbatical.

      Our bosses didn’t take one, so it was hard for us to take one. But I did have one boss who had three children in 5 years. And she was able to take three months of maternity leave for each one. I’m glad she did. Being able to have children and get paid paternity leave is a fantastic benefit. That is something I would have truly enjoyed.

      I was trying to take a one month sabbatical before I left for good in 2012. But things move too fast and they offered me a severance package that I could not refuse. And at the end of the day, it was the right move to take it.

  5. Quarantine has taught me this about work: As I long suspected, I really don’t need to go to the office every day or at all. I can do it all by logging in from home and I hate even my measly 15-20 minute commute so much that I prefer it.

    I get a fair number of slow days, whether in the office or at home, because, whenever my workload is increased, I write more programs and scripts that take care of it for me and just tell me if there is a problem. These slow days at home have taught me that it won’t be long after retirement before I wonder how I ever had time to work.

    We do want to travel a lot after retirement, but we can survive at home as long as it takes.

    1. The best definition of being happily retired is when you can actually say that you had no idea how you ever found the time to work.

      When I retired in 2014, I took a year or so off just staying home and traveling locally with my then girlfriend. My plan had always been to travel more and in 2016 I finally started. From 2016 to the end of 2019, I traveled for at least nine months per year, going around the world several times. Russia and China became part of every summer with other destinations chosen simply because I had never been there. In 2020 I rented a nice house in a rural area and focused more on cycling and learning to cook. I still yearn to travel like before where I often did not even know where I would go the next day much less where I would sleep. I honestly hope that one day I will be able to do that again, but I am not getting my hopes up. I believe too many people are putting too much faith in an experimental vaccine – I trust there are researchers in countries outside the United States looking for real cures as I see that as the only way out of this mess. Vaccines are at best a stop gap measure and let’s hope that long term adverse effects do not themselves become a problem.

      1. You and I think a lot of like….my retirement plans when I’m ready/able will look a lot like yours with 9 months traveling and 3 months back home. I also worry about these pseudo vaccines long term, but think we’re going to get herd immunity regardless….likely hit early stage herd immunity in the US over Christmas break, and if it wasn’t for these new strains, may have already hit herd immunity. 32m confirmed cases in the US x 5-6 more cases than confirmed (nearly all assymptomatic) is ~half the population that’s already had the virus. International travel may be a basket case for a long while longer than this year, though. At least the Carib is largely open!

    2. A good 4 hours a day of work gets 90%+ of the job done. I believed this while I was working, which is one of the reasons why I got out so I could be more efficient with my time.

      So much wasted time commuting, being in meetings, and corporate politics.

  6. Ms.Conviviality

    As someone who has read all your articles, I’m experiencing deja vu about your wanting to retire again. Some people are just wired to constantly be achieving one thing or another otherwise they get bored. You have so many original and brilliant thoughts that I find it hard to believe that you will ever be able to dial it down when it comes to writing. Maybe this new stage of your life will be more focused on authoring the next NY Times bestseller rather than the blog. I can imagine that writing a book is such a huge undertaking so it makes sense to reprioritize how you spend your time.

      1. I believe you write really well and I am pretty sure that bestseller is on the way.
        I would want you to share your ideas on the benefits of investing in real estate.
        I myself believe in the idea and would love to understand your thoughts on it as well.

  7. Hello Financial Samurai,

    I think it’s great that you’re comfortable enough to re-retire. After spending over a decade in banking with grueling hours and writing for relatively the same amount of time, it’s certainly warranted that you take as much time as you’d like to enjoy your family and the lifestyle you have afforded.

    One thing I’ve noticed is that with the economy still technically recovering from the pandemic, unemployment still fluctuating and massive stimulus packages, it still amounts to an ever-increasing amount of taxes.

    When you look at the numbers it adds up quickly. I have never met anyone who would volunteer to pay more taxes each year. Not only that but most people don’t get that it’s just as unfair to expect those who’ve reached a financial status to be in the highest tax brackets to just swallow the fact that states like New York and California decided that they must pay even more.

    People don’t seem to differentiate the fact that the middle class still includes those who gross upwards of $400,000 annually and those same people continually perpetuate the “poor vs rich” unfairness but in reality, middle class doesn’t equate to being rich.

    For over a decade there’s been financial advice about how to diversify income which means…. lower tax rates or at least multiple tax rates that lead to lower income to be taxed on. There’s no crime in not wanting to feel like you’re getting fleeced by Robin Hood in the forest. Perhaps more people will take the road less traveled.

    1. Sure. Being exhausted and then having to pay more taxes is not motivating to continue working for some people. Hence, my hard stop from working more than I want is when taxes go up.

      And it’s totally fine. We need to pay for all our stimulus spending. I’ve paid six figures in taxes a year for around 20 years now. But now, I want to spend more time with family and heal from a long pandemic.

  8. So I’m curious on the missed opportunity regarding working in Asia. Given that you are retired (x times) and still working for yourself, with a very large safety net. What stops you from going to Asia and working on FS form there for a few months or years. You would be able to claim you are working there, you could live the life. What is preventing that? Was it truly you only wanted to experience that if paid for by another with a company card and all the perks? Seems like in your situation, and with a website business (or 2 or 3, etc.) you could live your dream.

    I would think total language immersion would be easier for your kids as well. Certainly would be a lot cheaper than a private school in San Francisco focusing on the language as well. And, best of all since you own your houses, you could just continue to rent them out and add your primary to the list and come back in a couple years.

    It’s always easier to plan someone else’s life, isn’t it…

    1. Yes, the dream isn’t over yet. We plan to move to a Mandarin speaking country for two or three months of the year once our daughter is at least three or four years old. So in two or three years. Then our son will be six or seven years old and really remember his trips.

      Taiwan is a favorite country given the language and the food. Further I grew up there for four years. So we can go back for the summer or winter’s every year, that should help with language skills and with the filling my desire to work abroad in Asia.

      All of this takes planning and patience. And when you throw Covid into the mix, things aren’t as simple. But just as well, since we wouldn’t be traveling internationally for the first three years of our daughters life anyway.

      How about you? Did you travel abroad with kids?

      1. So my dream I suppose is to take on working or at least living abroad when the kids are older. I had a work opportunity to move to outside of London a couple years back when my wife was pregnant but we decided it wasn’t the right time. We wanted to be closer to family when the kids were born. Which was ironic in a sense because flying to London is almost as long as driving to see family was at the time. My wife’s parents moved to Europe when she graduated High school and lived there for about the next 5-6 years. Then they came back and settled again in the US. She had the luxury during college to go see and parents and travel Europe college breaks. I would really like to be able to do something similar for my kids when they are older, and really for myself. I think it would be fun to live in a different country for awhile if only to get more experience. I used to have some more travel for work including abroad trips. I would go to the UK or other to witness test equipment, and would tack on a few days here and there to travel around as well (company or vendor paid of course). There is something special about older countries, and it’s funny to think they have apartment buildings that are older than the United States, let alone churches and temples and all that. Amazing.

        Embarrassingly enough, we haven’t traveled out of the country since my kids were born. My oldest is nearly 5, where does the time go?! We were thinking about it and nearly booked flight last year prior to COVID ending that plan. So perhaps next year or so we will revisit the topic. My kids haven’t even been on a plane yet! They have however been to 13 states though so they are still getting to see different things.

        1. 5+ is the perfect time to start traveling! It’s really a PITA to travel with kids. So much easier to load up the car and drive somewhere within 3-4 hours instead.

          It’s going to be fun for us in the future! The anticipation is half the excitement.

      2. Money Ronin

        I did the summer Taiwan thing when my kids were 6 and 7. I wish I did it sooner, and I wish I could do it again. In middle school, they just don’t have time for that sort of extended leave.

        Most people avoid traveling with young children, but I did it anyway as early as 11 months. It’s all about setting the right expectations—you’ll accomplish less but you’re still seeing the world. It’s better than accomplishing less while stuck at home.

        1. We’ve already seen the world, which is why I’m not motivated to travel anymore. 13 years growing up overseas and 13 years working in international equities. So we will wait.

          Why is there less time during middle school? Vacations are the same no?

          1. Kids are super busy with school work and extracurricular activities. Summers usually involve sports and enrichment programs. Among the private school track, By 7th/8th grade, you are applying for high schools which is similar to applying for college (school visits, applications, resume padding).

            Despite this, introducing the world to my kids is important. And I purposely take them to some rough places. It feel strongly about getting them out their upper middle class bubbles.

  9. Great game plan that anyone can follow. I love the analogy of setting a date as similar to finding out you got accepted to college (I did early decision at Johns Hopkins so I had even more time to enjoy 12th grade).

    For me it is still hard to find concrete things I plan on doing in retirement. Still on the generic I want to travel, etc. I do think if I can keep my blog going it will be a great outlet to keep my mind sharp and stay out of boredom. Writing a book has been something I also have tossed around in my head.

    I’m trying to coincide retiring with my daughter going to college. Passive income right now should exceed what I think would be a good annual draw in retirement so I hope it only continues to grow in the next 3 yrs (want to retire at 53 (turning 50 in 9 days).

    1. GL! It will be interesting to see if you actually retire at 53 with the amount you are making and being a doctor.

      I bet it is going to be MUCH harder than you think! One more year syndrome.

      I gave up a $250K base salary, and that was tough. I’m assuming you make much more than that as a doctor.

      1. Yeah it is definitely going to be tough. I have one more year syndrome bad already (I have surpassed my original net worth goal when I started out 7 years ago).

        What is making me hesitate more than ever is possible inflation issues/devaluation of the dollar. I do not believe CPI is true reflection of inflation rate (govt wants us to believe it is under 2% but go to a lumbar store or even groceries and that makes you realize that we are being fed a line by the Feds). I actually wrote a post recently about COLA and how it is purposely kept low based on selective inclusion of items in CPI.

        So I’m not sure how much is enough anymore.

        1. My solution is buying as much real estate as I comfortably can to ride the inflation wave.

          Have you achieved a net worth of $10 million yet? If not, I think that’s the level where you can feel good retiring. If your $10 million appreciates by 10%, that’s $1 million. And for most people, that’s more than what they earn from their day job.

          Besides, Doctors should work until 70! Our pediatrician is retiring at 74 this year :)

          1. Haven’t hit Decamillionaire status, which would certainly be a pipe dream for me. Doctors have a tough time getting to that level because we typically have a lot of educational debt (I had over $300k), low pay during residency so defer/forbear most of it, and then a bit of lifestyle inflation when first become an attending.

            Also I got hit with a major whammy with the awful divorce right before I turned 40 (which was featured in a guest post on this site :) ). At that time I was negative $850k.

            All things considered I’m doing far beyond expectations about to turn 50 (not including home property I am approaching $6M net worth (mainly through lucky investments (like my medical office building that got sold in 2019 and various real estate syndications) and completely debt free).

            Not sure I can make it to 70 working. It’s getting to be a real struggle. Medical reimbursements declining and the hamster wheel can only go so fast.

            1. Gotcha. If you get to $6M, getting to $10M is highly feasible within 5 years!

              That’s what I’m saying.. it gets tougher and tougher to leave the more you make and have. But maybe not, since you have more to enjoy!

  10. I like that you’ve really given your readers (myself included) a perspective that retirement is not black and white and that you can cycle in and our of mini-retirements and re-retirements with intent and planning. That goals and circumstances change whatever your age. Makes it easier to not feel you’re making such permanent decisions.

    I wish I had come across your blog before I left my job last summer out of burnout and frustration. I could have refinanced with all time low interest rates, but for whatever reason every cycle this happens I seem to be in a mini-sabbatical.

    Did not anticipate how closed the world would remain and would have even taken another job while riding out being grounded. (Hong Kong has a mandatory 3-week quarantine in a gov’t designated hotel–at your expense–, which is brutal and has no end in sight.)

    The good news is now that my eyes are open, from reading FinSam and others, that I won’t be completely just spinning and avoiding any existential questions/planning. So, for that, Thank you!

    1. “Hong Kong has a mandatory 3-week quarantine in a gov’t designated hotel–at your expense–, which is brutal and has no end in sight”

      That quarantine in a hotel room for 3 weeks is not worth it at all! I would only do it if a relative or close friend was on his or her last legs. These examples are so unfortunate due to COVID.

      Hopefully you’ve been able to recharge since you left your job last summer? Got to look at the positives, there are always some.

      I didn’t anticipate the lockdowns and COVID lasting this long. But as the saying goes, “If you’re going through hell, keep going!”

      1. I sat in my chair too many hours. Too many movies. 25lbs. All bad. I started thinking of trips I never took, because It wasn’t the right x to spend the money. It was never the right x. No more.
        I took a chunk of money and bought an annuity. Not as an investment, but as protection from saying “I can’t afford that trip right now.’
        It pays $4500 each month for ten years. A three night trip with the wife is one month. Recent family vacation three months. Ten days East coast three months.
        Now, I don’t think in terms of money. Cruise three months.
        I hope I spend all the money; otherwise it goes to my children along with all the other money. Inherited money is never appreciated.

  11. “I slowly became resentful of our politicians who seemed to live by different rules.” Now only if you would also become resentful when politicians raise our taxes! If you cannot trust them to play by the same rules, how can you possibly believe they are spending our money for the betterment of society?

    1. The solution is pretty easy Alan. I’ve decided to take action, like I always do and retire by the time there’s herd immunity or whenever taxes are raised, whichever comes first. Perhaps I wasn’t clear about my plans to retire in this article. I will go back and emphasize this somehow.

      I’m tired. And the added bonus of retiring is that my tax bill goes down as well.

      What are some of the actions you have done to pay less taxes? I forget where you are in your financial journey. Please remind me.

      Related: Don’t Make Over $400,000 A Year: See How Some Suffer

      1. I am a retired Foreign Service Officer much like your parents.

        I have money invested with a financial advisor where short term gains are the norm and obviously result in higher taxes. I really do not want to move that money due to his long term record.

        I have been investing a bit in platforms like Fundrise and FarmTogether in order to further diversify. I also invested in an Opportunity Fund from Fundrise in order to defer some capital gains.

        I would prefer to keep a larger portion in cash but with the current interest rates, it provides nearly no income. The best account that I have been able to find, a checking account from T-Mobile pays one percent and even that is substantially better than anything else I have found.

        Any recommendations?

        1. Cool. As a retired FSO, then you should have a lifetime pension. Life is good. Invest based on what you like and know. No need to take on excess risk at this point in time.

          I’m hoping rates go higher so I can find myself some good CA muni bonds again.

      2. I saw one of your regrets was not working in Asia in satellite office. Apart from the experience, that is one way for sure of paying less taxes.

        I did my own taxes this year, and between spouse and I each claiming the foreign earned income exclusion ($107.5K per spouse), and housing exclusion (49K), we excluded $264K of income from AGI/Taxable Income. Then you can apply your foreign taxes paid or “Foreign Tax Credit” though that’s only prorated to income you haven’t already excluded under FEIE. Since we owed $0 to US, basically our effective tax rate was the Hong Kong tax rate, which was 15% flat. Certainly helped, given the high cost of living here.

      1. No one believes you are able to slow down. I am 71 and work because I can’t slow down. We all wish u the best, but if it isn’t your nature, that is ok. Just accept who u are and go on down the road.

          1. No kidding…those with health scares…please retire now.

            Just buried a close relative of my spouse who was still working when diagnosed with terminal cancer at age 70…that particular cancer runs in the family & had already killed a younger sibling…spouse’s relative didn’t make it to 71.

  12. Thanks for the advice! I’ve just been biding my time during the pandemic, saving as much as possible and getting my health and retirement benefits. But I definitely plan to take a break and then find a better job by next year.

    Life is too short to do something you don’t really love to do!

  13. Congrats on your re-retirement plans! You’ve been cranking out great content as per usual! I’m glad to have found your site during this time frame and you were more active.

    I took a mini retirement without a real plan of action. The first 5 to 6 months were really great but once I started to figure out what I wanted to potentially do next I was a little lost.

    Eventually I figured out that I could retire anyway, only after brushing up on my finances and taking them over.

    I also recommend the book The Artist’s Way for anyone looking to explore other interests and/or looking to make a change in career. It helped me to realize that I wanted to write and led to me launching my site.

  14. I am glad I got to have a retirement dinner party, and a few other get togethers to thank the people who had been so instrumental in my career. I had about two months to get ready for retirement and did negotiate a decent severance as well as pretty much coast that eight weeks. I didn’t work any long days and it was a nice slide away from a three decade plus career. I also used the time to set up the retirement consultancies I’ve done for the last five years. They added over $500K to my portfolio while only taking up a few hours a week of my time. Of course I did all this much older than you, largely because I had really enjoyed my job right up until I didn’t.

  15. Such a thorough & thoughtful post!!! You have matured so much in the last few years. FIRE is great but not the puppies & rainbows many 28 year olds claim. I’m 47 years old and my husband is a teacher who can retire in about 4-5 years.

    I am doing TONS of soul-searching about what I will do when he retires. Our daughter will still be in high school so I will probably continue working, but I definitely want to scale back, take a sabbatical, maybe a new challenge at work or do something less stressful.

    For the last 5 years I’ve been stockpiling all my bonuses with the thought of FIRE, but then I realized that I enjoy the mental challenge of work and get alot of intellectual stimulation from my very smart co-workers.

    During the pandemic I’ve taken some time off for house projects, family-time, etc. and it’s been good but it’s making me realize that I need mental stimulation and a sense of productivity. Not sure I can ever full retire. It takes time to get the balance right. Looking forward to more posts like this!

    1. Hi Margaret, soul-searching is a writer’s middle name!

      He said something interesting. He said you are wondering what you are going to do after HE retires.

      Can you elaborate? Retirement is more fun if you get to go on an adventure with someone.

  16. I very much enjoyed this article. I’m also eternally grateful for your increased writing during the pandemic. Financial Samurai is/was one of the few highlights, I personally looked forward to during an otherwise difficult year of pandemic adjustment.

    I am probably 10-17 years from retirement (46 now). I begun to wonder if I’ll wish that I had tried harder at work earlier in my career, as opposed to my primary focus which was on my family (wife, 3 daughters). I feel like I could’ve made more money, certainly at the expense of time with them. I do not regret my choices. We’ve made investments in real estate, have retirement plans (including wife’s pension) and are better prepared financially, than 99% out there, but the competitive flame in me, still wonders.

    I’m excited to explore the pre retirement checklist with my own situation over the remaining decade or so. A couple of items I will add for myself include: the elimination of all debt, including mortgages. Put all three children through college debt-free. A system in place to fund travel 3-4 times per year in retirement, before I pull the retirement trigger.

    1. Hi Jim – If there’s one thing I know, it’s that we parents will NEVER regret the time we spent with our kids!

      And having a goal of working until your kids graduate college is a good one. It provides more meaning to work, and I do hope you enjoy your remaining 10 years of work.

      Best of luck!

  17. Thanks for such a thorough post! It’s a lot of work to put together an article like this. I didn’t realize this until I tried writing articles myself. There’s a lot involved with running a website, especially a successful one.

    I hope you can get more balance this year and take things down a notch. This pandemic has really put us all through the ringer. And I can’t wait for it to be over and done. We’re getting closer! Hang in there!

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