Personal Lessons Learned Since The 2008 – 2009 Global Financial Crisis

With the Federal Reserve determined to hike rates further, another global financial crisis might be brewing. The Board Of Governors are all very rich, so they'll be OK. However, a world of hurt could be coming for the middle class who will lose their jobs in droves.

Thankfully, balance sheets are stronger this time around. Many of us have also diversified based on our risk tolerance. Therefore, I don't think this next recession will be as bad. However, you never know for sure with risk assets and policymakers.

We almost went through another global financial crisis with the failing of Silicon Valley Bank. Luckily, the federal government stepped in to backstop all depositors of SVB and Signature Bank.

On September 15, 2008, Lehman Brothers did go bust. I remember this day clearly because I made a $100 side bet with my friend the US government would bail it out. To my surprise, the US government didn't rescue Lehman, and the stock cratered that Monday and never recovered. This is my most poignant memory of the financial crisis.

Despite all the economic devastation, I wouldn't mind rewinding time and going back to 2008. I'd rather be 31 than 45, simply because I love life and want to live as many years as possible.

Even though central bankers and politicians say we aren't in a recession, we clearly are. Here are some lessons learned during and since the last financial crisis.

Personal Lessons Learned Since The 2008 – 2009 Financial Crisis

I've been investing since 1995 and currently manage an 8-figure investment portfolio. At 45 years old, I have no desire to go back to work so my wife and I can spend as much time as possible with our two young children.

Here is some wisdom I've gathered since the global financial crisis.

1) It's really hard to go all-in, even when you know you should.

Despite telling myself over and over again that we were in the buying opportunity of a lifetime, I couldn't convince myself to invest much more than my usual 401(k) maximum because my world was falling apart.

A couple dozen friends had been laid off, including my best friend at the time, who worked at Lehman Brothers. I feared I might be next and would need as much cash as possible to hold me over just in case.

In 2005, I had taken a $1,200,000 mortgage to buy a single family home. I already had around $380,000 in mortgage debt from the first property I bought in 2003. With property prices in San Francisco falling along with the stock market, bankruptcy was a very real possibility if I had lost my job.

Therefore, I built a significant CD portfolio with most of my excess cash instead. At the time, the best 5-year and 7-year rates were at 4.25%, so I decided that was where most of my savings went. The situation is similar now with me buying Treasury bonds yielding 5%+.

The only things I did right were keeping my job, not selling any real estate or stocks in the middle of the downturn, and maxing out my 401(k).

Events leading up and through the 2008 financial crisis

Debt is the real killer during a financial crisis. Please make sure you have enough liquidity to last you through at least six months of living expenses in case you lose your job. You do not want to be a forced seller during a market meltdown.

At the very least, please keep contributing to your tax-advantaged retirement accounts.

See: Your Risk Tolerance Is An Illusion: Just Wait Until You Lose A Lot Of Money

2) Chaos is a great motivator to change.

If you've been procrastinating for a while on something you should do, now may be your time! Doing something new might not only ease your mind, but provide you some insurance in case things get really bad.

I had been putting off starting Financial Samurai since 2006, when I graduated from business school part-time. But once the financial crisis hit, I decided to finally launch in the summer of 2009. If I got laid off, I needed a backup plan.

The pain and suffering you feel today might be the best thing that could have ever happened to you. But it would be much better if you could predict the upcoming pain and make some changes before the pain happens.

For example, instead of experiencing a heart attack before we change our eating and exercise habits for the better, why not change now? Instead of getting a divorce because we neglected to work on our communication skills, why not actively work on listening better today?

Study the people who've been through a lot of pain to try improve your odds of not going down the same path. Always work on your X-Factor. When the next financial crisis comes, you'll be more ready than 97% of the population who doesn't think ahead.

14 years later, I've written over 2,500 articles on Financial Samurai. I also ended up writing a WSJ bestselling book called Buy This, Not That. My X-Factor gives me something wonderful to do in early retirement, not to mention pay for all our family's living expenses.

3) Family is everything. 

You can always make back your financial losses. But you might not always be able to repair your relationships.

In 2008, decided it was time to get married. I had known my wife since college, and she would be turning 28 in mid-2008. For some reason, 28 always stuck in my head as the perfect age to get married for her. I wanted to wait until at least 30 to focus on my career. How convenient it was that I am three years older.

The difficult times of 2008 made me want to hold onto her even more. I could lose everything, but I couldn't lose her. Relationships were more important than money back then, and they are still more important than money now. You will regret sacrificing love for money.

Today, my wife and I are blessed with two wonderful kids. When I get depressed thinking about losing lots of money in a bear market, I find instant comfort in my family. Because of my family, I don’t feel nearly as much pain as I did in 2008. Just an elevated amount of worry.

If you are looking for love, it is absolutely worth spending more time to improve your chances of finding someone. Once you have enough money to survive, family is by far a greater asset.

Related: Solving The Happiness Conundrum In Five Moves Or Less

4) You gain a tremendous amount of confidence over time.

One of the great things about time is that you get wiser, savvier, and more efficient.

Previously, I'd always been embarrassed to ever say I was an expert in anything. But once I turned 32, 10 years after graduating college, I finally felt I had developed some expertise in finance. And now that I'm in my 14th year of building Financial Samurai, I have no problem believing and saying I have expertise in personal finance and digital media.

Because of this experience, I also no longer fear financial ruin either. If Financial Samurai shuts down and all my passive income goes away, I know I can get a job back in finance, fintech, or online marketing. The pay would be enough to provide for a simple life for my family.

Feel good knowing that each year that goes by, your expertise in your field grows. You will eventually reach a point where you will no longer feel like an impostor. You will start to own your destiny.

Use a financial crisis as an opportunity to invest and upgrade your life. Once the pandemic hit in 2020, I bought some stocks in March 2020. Then I bought a forever home in June 2020.

Today, my investment portfolio generates about $380,000 a year and passive income. I’m confident that no matter how bad the next financial crisis is, my wife and I won’t have to go back to work.

Our new home improved the quality of our life during the pandemic. Further, I decided to focus more time making money online and writing a much-needed personal finance book, Buy This, Not That. It is a WSJ national bestseller.

5) The more things change, the more things stay the same.

I met many disgruntled people before the 2008 financial crisis who complained about the government, taxes, inequality, racism, bigotry, sexism, and more. I also met lots of people who told me about their days as dotcom millionaires in 2000, including the guy who made my breakfast bagel each morning.

15 years later, we still have the same complaints. Yet, instead of losing money in dotcom stocks or housing, it's losing money in cryptocurrencies and growth stocks. Instead of hearing complaints in person, complaints are amplified all over social media ad nauseam.

You're either going to let things get to you, or you're going to do something to change your dissatisfaction. Just think about how much you could accomplish if you worked for one extra hour a day for 10 years.

We're talking about 3,650 hours of extra productivity to learn a new language, build a business, become an expert at work, or make a difference in a kid's life.

If you want to change, please take action. And no, virtue signaling does not count as taking action. If all you do is complain, 10 years from now, you will still be complaining about the same things.

6) You'll regret more the things you don't do, than the things you try. 

Conrad, my 56-year-old colleague who worked in the mailroom told me this a couple weeks before he was let go. He had been reminiscing about all the things he wished he'd done in his 30s when I asked him what he would have done differently if he could rewind time.

His layoff angered me into figuring out an exit plan since he only made about $40,000 a year and needed the money more than most.

Since 2008, I've had some regrets. They include not taking a guaranteed offer to work for a new company in NYC in 2010, not starting Financial Samurai in 2006, and not trying to have children sooner. As a result, I'm trying to make up for lost time.

I should have jumped at the work opportunity to move back to NYC with a big pay raise. An upstart firm had offered me a 50% bump for two years guaranteed. Who knows if they would have honored the second-year guarantee if I underperformed. But I'll always be left wondering what if.

Given I negotiated a severance two years later, not getting that last bit of extra cash was a mistake. Then again, if I had joined the new company and wanted to leave after two years, maybe I wouldn't have been able to negotiate a severance.

Given this regret, I've forced myself to try new things, such as becoming a high school tennis coach, becoming a foster kid mentor, writing a song, creating a podcast, and publishing a new personal finance book. The next great challenge may be finally relocating to Honolulu when our daughter enters kindergarten.

Although feeling regret is tough, there's no point dwelling. Reflect and move on. Conduct a regret minimization exercise in order to make better decisions today!

7) Even if you see the future, it's hard to take advantage. 

During the first year after leaving my finance job in 2012, I wasn't entirely sure leaving was the right thing to do. So I kept in contact with colleagues, met with recruiters, spoke to ex-competitors, and applied to various tech startup jobs online. Here was my chance to potentially try something new without worrying about earning maximum income.

The first place I applied to in 2012 was Airbnb. I thought it would be a big hit. I attended a couple of their Friday happy hours. Unfortunately, I didn't even get a chance to interview. See one of my rejection letters below:

Tech job rejection letters

A couple months later, Airbnb raised money valuing them at around $2.5 billion. If I had been able to get $200,000 of equity and stay for the full four year vesting period, that equity would be worth roughly $5 million today. At its highs, the equity would have been worth over $10 million. Oh well!

What I'm Investing In Now

Today, I believe buying real estate in the heartland of America is a wise move. However, deals still go sour even if you invest in the right state, city, and platform. As a result, choosing the right real estate investing platform and doing your due diligence are paramount. Things can and will go wrong.

To gain outsized reward, you must take commensurate outsized risk. If you are not willing to take any risk, learn to be happy with what you have.

Even if you have the best vision, sometimes you simply cannot capitalize on it. Don’t beat yourself up about it. There will always be more opportunities in the future.

8) You have more abilities and strength than you realize.

Even though I wasn't able to get a single full-time tech/startup job offer, I was fine with the rejections. I wanted to fully experience this new life with Financial Samurai. The rejections gave me comfort knowing that at least I tried to find something. Now I could move on with no regrets.

Financial Samurai's growth has actually exceeded Airbnb's growth so far, but with the added benefit of pure control and autonomy. I learned how to mix creativity with sharing practical financial knowledge. Before then, I was so restricted in what I could write due to compliance. It was frustrating. I also learned I had more endurance than I thought possible.

Whatever you think your limits are, know that you're probably utilizing less than 50% of your full potential. It's only when you're hanging off a cliff with one arm, will you find your true inner might to pull yourself up.

9) Time fixes and breaks everything.

Even if you had gone all-in the day the S&P 500 peaked on July 1, 2007 (1527), despite losing ~50% by October 2008, you'd still be way up if you had held on to today. It's hard to lose money in the S&P 500 over a 10-year period.

Real estate has seen a similar recovery in many markets around the country. Over a 10-year period, you will likely do very well investing in real estate. And during stock downturns, real estate tends to significantly outperform.

Unfortunately, these past 15 years of playing sports have truly taken a toll on my body. My left knee feels like it may have permanent ITB/TFL damage. My right shoulder must have a tear because it hurts when I try and throw or serve hard. It's sad to no longer be able to move like I once did.

Please cherish your health! Do more stretching and warmups. It's not worth going all-out in sports anymore due to injuries.

At 46, I have adapted to my aging body by playing less tennis and playing more pickleball. It’s so much easier on the joints. That said, I still jammed my back one day lunging after a ball. I couldn't walk the next day!

The middle-class will likely get hollowed out with the next recession. Therefore, make sure you have the right number of banking relationships and a diversified portfolio.

10) Friends come and go.

I no longer hang out with the same people that I used to hang out with in 2008. My best friend from Lehman was never really the same after the layoff. I got him an interview at my firm to work with me, but one of my Australian colleagues nixed him.

I used to hang out with several client friends for drinks, golf, and dinners. But after I left the industry, I no longer had the enthusiasm to keep hanging around in a business I no longer enjoyed. It really takes a lot to maintain relationships when you don't have something in common or a corporate card!

Since 2008, several friends and family members have sadly passed away. It's is likely even more will pass away over the next ten years. Therefore, I plan to spend more time with my loved ones than in the past.

The pandemic has made many of us more lonely, due to health safety precautions. As a result, it takes more effort to combat loneliness. The good thing is that many more people are looking for companionship. So, if you make the effort, you will find more friends

Related: If I Could Retire All Over Again, These Are the Things We'd Do Differently

11) Being wealthier won't make you much happier.

Most of us have more than tripled our wealth since the previous peak in 2007. But do we feel much happier? I venture to guess most will say no.

I don't feel happier because I was never an unhappy person to begin with. I've always been around a 7 – 8 out of 10 for my steady happiness state. I will occasionally shoot to a 10 when amazing events happen such as the birth of my son and daughter. But that elevated level of happiness never lasts.

Instead of stressing over doing well with a work client, now I wonder whether my children will find their own happiness. Instead of worrying about whether I'll get promoted at work, I worry about whether I can continue providing for my family due to the rapid increase in healthcare and tuition costs.

Thanks to having more money, I do appreciate not having to stress about getting a $104 parking ticket or having to ration my food. But I've also become accustomed to such convenience, and therefore, can't help but take my wealth for granted.

The only thing I've found helpful to combating hedonic adaptation is to show gratitude given I believe our outsized wealth is mostly due to luck. Volunteer to help others and write out your blessings. If you don't want to start a site, at least start a gratitude journal. Writing is the best free therapy.

After more than 11 years of early retirement, I have come to realize I have a higher steadier state of happiness. But it's taken me a while to realize this because life is full of twists and turns.

best reason to retire early - greater happiness

12) Once you're ahead, stay ahead.

When all your friends are making lots of money in a bull market, even if you've already made enough, you can't help but want to make more. As a result, you end up taking unnecessary risk.

Post-pandemic, there was an incredible amount of investing FOMO and real estate FOMO with so many speculative assets going up. Your goal is to beat greed and not deviate from your investing framework.

Over the years, I have received plenty of pushback from equity investors who were all-in whenever I wrote about investing in bonds (terrible year in 2022!) and structured products that hedge against downside risk. Going through the 2000 and 2008 downturns were enough to make me realize that the good times don't last forever.

However, due to my lack of discipline, I didn't invest as much in individual muni bonds and structured products as I should have to protect my wealth. If I truly stuck to my desire of happily growing my net worth by only 5% a year, I would have invested even more conservatively.

It's OK to sell stocks on occasion to buy things you want. Otherwise, there's no point investing in an asset that provides zero utility.

Learn to stay focused and simplify

The wealthier you become the more important it is to shut out the noise. When it comes to investing, everybody has their own opinions on what you should do with your money.

Instead, make your own decisions. Stick to your appropriate net worth asset allocation in order to defeat investing FOMO. Investing FOMO can destroy your wealth in a hurry as many people who invested in speculative assets in 1997, 2000, 2007, and 2022 found out.

Personally, I really like investing more in private funds now. It's nice to invest in a 5-10-year timeframe and not know the daily price movements. Private funds enable to to focus on everything else that matters.

Please never confuse brains with a bull market! A financial crisis hit in March 2020. And another one could very well hit again in the near future with high valuations and an overly aggressive Fed.

Related: The First Rule Of Financial Independence: Never Lose Money

Focus On The Future

It's unlikely the stock market will perform as well over the next 10 years as it has over the previous 12 years. Expect lower return assumptions.

If you were one of the people who bashed me about my lower safe withdrawal rate suggestion in retirement, please be more humble. Think dynamically, not fixed.

To make so much money in stocks and real estate since the pandemic began is an unexpected windfall. The vulture investors are coming out now as stocks fall back to earth.

Use the downturn to review your finances, assess your true risk tolerance, and come up with a sound financial plan. Then list one or two things you really should focus on besides building more wealth.

Over the next 10 years, I plan to focus most of my time on being a present father. Kids grow up quick. I also want to do more traveling and writing. My hope is that my investments stay as far in the background as possible so I don't have to think about them too much.

My time for trying to build a fortune is over. I now just want to keep and spend down what I already have. The main way I can do this is by having a diversified net worth and a healthy passive income component.

Next up, I'll review how this current bear market compares to the 2008 bear market.

Protect Yourself From The Financial Crisis

The best way to protect yourself from a financial crisis is to be on top of your net worth. To track your net worth for free, sign up for Empower (previously Personal Capital), the web’s #1 free wealth management tool. It will help you get a better handle on your finances.

After you link all your accounts, use their Retirement Planning calculator. It pulls your real data to give you as pure an estimation of your financial future as possible using Monte Carlo simulation algorithms. You must pay attention to your money closer than ever before.

Personal Capital Retirement Planner Free Tool - Financial Crisis management
Personal Capital's Free Retirement Planner

Achieve Financial Freedom Through Real Estate

Real estate is my favorite way to achieving financial freedom. It is a tangible asset that is less volatile, provides utility, and generates income. By the time I was 30, I had bought two properties in San Francisco and one property in Lake Tahoe. These properties now generate a significant amount of mostly passive income.

In 2016, I started diversifying into heartland real estate to take advantage of lower valuations and higher cap rates. I did so by investing $810,000 with real estate crowdfunding platforms.

Fundrise is my favorite real estate platform. It enables investors to diversify into real estate through private funds. Fundrise has been around since 2012 and now manages over $4 billion in assets. For most people, investing in a diversified real estate fund is the way to go.

find out more

The key to great wealth is making it last over time. As a physical asset, real estate stands a greater chance than stocks in holding its value.

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. 

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91 thoughts on “Personal Lessons Learned Since The 2008 – 2009 Global Financial Crisis”

  1. Dear Sam. A great read. Great ups and downs etc. I’m just getting into financial markets in the UK. But so intrigued to watch how markets operate and how so many factors influence them. I’m perhaps down a touch with my pension fund as equities have taken a serious knock lately. But as you eluded to don’t get out at the wrong time. Rules in the UK allow us to take 25% of our pension funds tax free. Sadly if I was 4 months older back before the horrible Russian invaded Ukraine I would have been quids in or dollars in. But life is as it’s laid out so it’s a waiting game for markets to settle and hopefully equity values will return. Kindest regards Rory.

  2. Admittedly, some of your recent articles have not resonated with me personally. Sometimes what’s being written seems more like a product plug or marketing material.

    This write-up however, is such a great one (not that you need my approval!). As someone who graduated college into financial crisis, this 2007-2009 history really hits home. I watched my Business School’s sponsor swap from Wachovia to Wells Fargo mid-senior year. Internships were non-existent, planned placements were retracted, and job prospects were nil. I can remember going to interviews and there being what felt like 100’s of applicants. Sites like Monster, Indeed , etc. were still in relative infancy and most companies did not have (or have at all a) great online processes for career services.

    I was lucky enough to find a “real” job/career in 2010 after ~2 years of sporadic contract work in consulting. A job that put me in a position where I was eventually telling others to stay the course and also witnessing where peoples’ firms were leading them astray financially. In some cases, doing so to help prop up their stock or “guidance” around how to handle their pension. The desperation I experienced in many of these interactions was eye opening and something that has stuck with me.

    1. Sounds good. I’m always willing to refund you what you’ve paid to read my work if you’re ever unsatisfied! :)

      Glad you survived the GFC as a new college graduate.

  3. Great post Sam, it seems that developing some sort of talent or expertise on the side of whatever you’re doing is key. Like you said, now that you have all this knowledge for finances and Fincon, you’re essentially free. No matter what career difficulties come your way, you can alway tack a different direction and find success. It’s like Career Prepping!

    1. Hi Jim, there is a greater sense of calm and courage once you’ve figured out your finances and have a deep understanding of finances for sure.

      The calm and peace also comes with age and maturity. I’ve seen these cycles before, so you start getting used to it.

  4. “The Board Of Governors are all very rich, so they’ll be OK”

    Your ideas about this in the linked article are fascinating and well worth considering, but I think you may be too optimistic about their motivations. No doubt you’ve worked with people much richer than I. However, I have also had some experience with rich politicians. I used to work for a municipal government that has traditionally been the source of a number of politicians that went on to national status. I associated with some of these people on a “professional” basis if you could call it that.

    I saw no signs that any of these people were motivated by anything other than greed and the accumulation of money and power as ends unto themselves. If they were worth $50 million, they didn’t want to lose 10 million, a million, or $10.35 (ten dollars and thirty five cents) because they were simply greedy. They didn’t seem to understand the world in any other terms. Maybe they were just small time operators, and could have changed their ways after moving on to the state government and presidential administration. Not sure what implications the restrictions on Fed officials trading stocks would have, but I suspect the reaction in their hearts involved something like hatred or vengeance, rather than any lofty morals.

    1. It’s actually because I’m pessimistic about the human condition that the Board Of Governors may take tightening too far and crush the middle class for their legacy. They are already rich, so they can withstand the downturn easy.

  5. “My tenants didn’t bring up the shower, but I figured since my handyman had to come back, to finally fix the problem. The internals were 52 years old so we had to pound out the tile, cut the pipes, and replace everything.”

    I know this was from the newsletter and not this post but was wondering how you matched the tile on an old shower? Was it discontinued or do they still manufacture it? We just had a hot mop failure and the tile is discontinued! The tile is everywhere. Would hate to do a full remodel because we can’t match the tile! Ugh!

  6. “I am nibbling at current levels. However, with 10% higher expectations for the Fed Funds rate (4.1% to 4.5%), it’s rational to assume 5% lower expectations from my previous 3,666 S&P 500 downside target, i.e. 3,500.”

    Sam – Will you return to buying aggressively if we hit 3,500?

    “The S&P 500 declined 1.03% to 3,655.04, falling below the June closing low of 3,666.77.”

  7. This post resonated with me a lot. I’ve been in a funk that I’m climbing out of. Thinking back to how raw and scary things were back during the financial crisis reminds me to be more appreciative of where we’ve come since and to focus more on the positives of the present. But also to be cautious and careful to preserve capital and take steps to help ensure I come out ahead down the road. There are always ways to see the silver lining but we have to be willing to search for them and think in derivatives.

  8. Thanks – Given that you grew up in Asia, would you consider raising your children in Asia to get Asian education and what are your thoughts of it versus western education- or is proximity to parents and parental support more of a important factor as you mentioned moving back to Honolulu in raising your children?

    1. Although I grew up in Asia, I attended international schools. I thought they were wonderful because I learned Mandarin and English and got a tremendous amount of exposure to different cultures.

      I would love for my children to learn Mandarin in Honolulu so they can get to know their grandparents. I really enjoyed getting to know my grandparents and I hope they have the same experience.

  9. Thank you so much for sharing!

    I remember 2008 vividly. I graduated from college in December 2018 with a degree in civil engineering and was very fortunate to find a job in April 2019. I think anyone who lived through that time should be a little more prepared for what we’re experiencing now.

    I completely agree with your former 56-year old colleague. Fortune favors those who are willing to try new things and give all of themselves to it. You’ll definitely regret the things you wanted to try, but didn’t.

    Also, I really appreciate your view on love and family as it relates to personal finances. You can always earn more money…

  10. Buyside Hustle

    It’s absolutely true that you gain more confidence the longer you work in the industry. I remember I didn’t know anything my first few years as an investment banker and felt everyone around me was much smarter.

    Now after working on the buyside for a while, I no longer worry about not being able to get a job if my current role falls apart because I know what I’ve learned over the years will always been valuable at other firms.

    A lot of good insights in this article. Thanks for sharing.

  11. Brian Lasky


    Some great points presented here. Retired 2.5 years with a substantial cash pile and recent SPY puts for protection. I would suggest a visit to your GP for a recommended course of therapy- I continued to play hurt and just completed 12 weeks of occupational therapy for elbow injury.

    When are you going to transition to Pickleball? The sport is being driven now by ex-Div 1/2 tennis players.

  12. Thanks for your reflection Sam! I am seeing so many similarities today to the crash of 2008. Fortunately I have grown wiser (at least that is what I tell myself) and had some large put positions in my RH account on a few larger tech stocks. I’m wondering how long to hold these though. I am up big and would like to transfer the profits over the general index funds…since we should be approaching a historic buying opportunity in the market, but just not sure how far down this ship goes.

  13. ”Lessons Must Be Learned to Prepare For All Life Crisis”
    1. Live within 2% to 4% of all investable assets
    2. Get marry, have children and stay happily marry
    3. Drink water, walk/jog 2 miles per day and get 8 hours of sleep
    4. Have a hobby
    5. Pray and be kind to others

  14. Sam,
    Sorry about your shoulder pain. Turns out it won’t get better is you keep banging it around.

    My wife has had great luck with turmeric as an anti-inflammatory dietary supplement.
    You can’t just take the pills you find in the health food store. Work with the raw ingredient and add a little black pepper to the mixture. (be careful…turmeric stains anything it touches)

    Honest, it works. you should be able to get the guidance of a DOM in San Francisco.

      1. Sounds like a torn rotator cuff, or something on its way to being one. My uncle played a lot of tennis and had to get surgery.

        I found that, for myself, ibuprofen and getting a strap from Amazon to immobilize that arm while I was sleeping was enough to let it heal within a few weeks. Before that, it had been giving me grief for over a year.

        All depends on how bad it has gotten, I would suppose.


        “Please do not confuse brains with a bull market!”

        Ain’t that the truth! Too many people choose investments the same way they choose which horse to bet on, or what roulette number to lay down on. If they have a winning streak, even if followed by a losing streak, they may never believe they aren’t geniuses.

  15. Career regrets suck, but I don’t spend too much time worrying about them because you can’t change the past. You can only play the hand that’s currently in front of you. In 2013, I was approached by a headhunter about a career opportunity that would have been a lateral move, but would have been a situation where I was in line and being groomed for a promotion to CFO. I was comfortable and happy at the time, and making great money. I liked my boss and wasn’t really feeling that ambitious for more at that time of my career. I passed on even interviewing for the role, even though my background was perfect for it.

    A few years later my boss “retired” (was pushed out) and as I knew all along, no internal candidates were considered to replace him (much less me). The new outside hire was a complete jackass and I knew it was time to negotiate a severance package. I ended up doing some consulting work while I looked for something new, and a year later landed a new job making slightly less than I did before. That job turned out to be a disaster – the company was in a decaying industry with a CEO who didn’t have an operational background and wandered from strategy to strategy. I only lasted 2 years before I had enough and moved on again. It took me another year to find something new, and I’m making about 45% of what I did 5 years ago. The guy that took the job that I passed on in 2013 is now the CFO of that company and is doing great.

    And it’s all fine. Yeah, maybe I could be making 2X-4X what I’m making now, but I still do plenty well and could have retired at around age 50 after my last departure but chose to keep working. And I don’t work for a jackass or an incompetent narcissist anymore. The reality is that even if I had pursued that job back in 2013: a) I might not have even gotten it and b) I’m not sure I was in the right mental state to become their next CFO. I am where I am, and it’s fine.

    1. True. I don’t have deep regrets for not moving to NYC for the big guaranteed pay jump. But it would have been a great adventure to make more money and go back and live in my favorite city in the world (for 6 months).

      Just got to keep moving on!

  16. Eric D Meyers

    Also, did want to mention. I also had an shoulder issue like this for a while and I went to see physical therapist and they found that my neck was the culprit. It took 6 weeks of PT, but it honestly made my right shoulder feel new again. Mine was related to sitting too much. I was working 10 hours, driving 2 hours, and then working on homework at night for college. Which led to the issue. Might want to see if that is the same issue. They made it sound like it was common in those who were desk workers.

  17. Hi Sam,

    Just noticed that this a 2018 post. A sign of good writing to me is if it still holds relevance in the future. This post definitely does! My biggest lesson from 2008 is that the market always comes back. I’ve been buying this market above and beyond normal for the last 7 days. It’s getting harder every day which tells me I’m doing the right thing. I always wished I invested more in 97, 01, 08, 12, and end of 18. I’m not gonna make that mistake this time.

    Thanks, Bill

  18. Great article and a great reminder in this time of crisis! I lived through 2 of these stock melt downs already, and I have less concern on this one then the previous ones. Stocks are still overpriced and have been for the last 3 years. i stopped putting money in US stocks for the last 2 years, and once the market correct 20 or 30% I am going back in. The fundamentals of this economy are sound, but with ridiculous low interest rates people started chasing stocks to get some type of return and ignored the fundamentals. This crisis will pass and people who didn’t lose their head will be fine. During the crisis focus on what is really important FAMILY!

    PS. Don’t get shoulder surgery! It has enormous (6 months +) rehab time and anyone I know who had it wish they would have waited.

    1. Good feedback on shoulder surgery. I don’t plan to do any surgery unless it is absolutely too painful. I can’t live without playing a sport for longer than a month, so surgery is out of the question.

  19. If we go into another recession it definitely won’t make me happy but I think I will be better mentally prepared than the last one. We’ve also been overdue for one so it won’t be a complete shock, although I wouldn’t have guessed that the next one could have been triggered by a virus. Just goes to show you just never know.

    I’m tapped out of cash for now but plan to leg in here and there as I get funds if the markets stay down or sink further. And I also plan to pay down more debt. That always feels good, especially when rates are dropping.

    It will be an interesting week in the markets so I’ll definitely be paying closer attention than I normally do. Thanks for writing so many timely posts! And good luck and wishes for good health to us all!

    1. I really, really thought I was done with refinancing. But with the 10-year bond yield at 0.45%, that’s around 1.15% below when I last refinanced. I’m assuming I can do a no-cost refinance for 0.5% lower….. so I should.

      It’s too bad the good times are over for a while. But we should appreciate the great run we’ve had since 2009!

  20. Hi Sam,

    I will not go all in time of crisis. I still maintain the approach of channeling the fund into the investment portfolio on a regular basis. This gives me the peace of mind regardless of the noises.


  21. This is a great post. I had no money and less direction in 2008. My life is completely different ten years later. But this time I’m losing significant money as the market goes down and I have a child on the way and a mortgage. I hope in 2028 we look back and say that we stayed the course and kept investing and that we are all healthy and fulfilled.

  22. I’ve gotten to the point of really feeling that there is only so much time left. Big difference being in one’s 50’s. Besides lasering in on how to best align my retirement with the years I have left earning, I’m focusing on local To Do list. Suddenly this year, I realized I had quite a few things I had wanted to do with them gathering dust on my list. Interestingly enough once I decided that was it, I’m going to start doing these things the opportunities came along. Joined the hiking group and went on a hike I’d been wanting to do, also went to museum’s adult evening night with them that my friends never wanted to go. Was invited to bingo this past weekend, I jumped at the opportunity and had a fun time. Granted all small things but enriching the fabric of my daily life.

    The other thing I decided to stop doing was using all of my vacation time and money for family events. Rather soul sucking to not have a real vacation for several years due to whatever major family event was going on. The last wedding, I flew in, stayed minimum of 3 days and then was out of there at the crack of dawn headed onward to my real vacation. They either will or wont get over it but solo vacation out West feed my Soul.

  23. Thank you for writing this. I was in the bubble called college when the recession hit so it’s interesting to hear of someone else’s real life experience and your reflections really ring true. I started to think more strongly about financial planning and retirement after reading about you and your retirement on CNBC and it’s been really eye-opening and life-changing, so while I’m sure the recession was incredibly brutal on you and wouldn’t wish it on anyone, I’m glad that it led to you setting up this blog.

  24. I didn’t really have an investment plan during the crisis ten years ago. All I had was my 401K, an IRA I never contributed to and an investment account that was all mutual funds but didn’t know how to manage it. The crisis actually helped me learn more about the stock market. I knew the basics but didn’t know about ways to manage a portfolio. For me, when I saw the value of my portfolio drop significantly, it made realize that I had to know why this happened and figure out how to recover from it. It also made me how to get ready when the next crisis because we all know it’s going to happen but don’t know when it’s going to happen, just like preparing for an earthquake.

  25. Reverse The Crush

    Very informative and interesting read, Sam! There’s a lot of wisdom in this post. I was not an investor yet when the 2008 crash happened. I was in College from 2008 to 2010 so my experience is limited. It’s cool to hear your perspective on the experience. Your point about maintaining relationships is very true. They require a lot of work. And you are very fortunate to not have any close people pass away in that time. Unfortunately I experienced one big loss during this time. I think your 3rd point is really interesting as well. Even though I haven’t achieved anything significant with investing yet, I am just beginning to grasp the surface of being confident with it.

    As for your questions, I plan to be reaching or nearing financial independence in 2028. It will be through a variety of income streams. Otherwise, I have simply grown as a person by becoming an adult over the past 10 years. I have much to learn still. Thanks for sharing, Sam!

  26. Lots of wisdom here Sam. Thanks for the great article.

    I particularly liked point #5. It was a great push and motivator for me.

    As I am pretty young, my only big regret so far was not going abroad for college. That’s not to say there are some other small things I would have liked to have changed, but c’est la vie.

  27. “The difficult times of 2008 made me want to hold onto her even more. I could lose everything, but I couldn’t lose her.”

    D’Aww everytime you talk about your wife, it’s like “awww” inducing!

    That rejection letter from Airbnb is kind of funny! It’s quite a neat souvenir in an odd way. I keep my rejection letter for laughs when I look back on them =)

    “I’m very lucky that nobody I’m close to has passed away since 2008. But I’m not so sure the same can be said over the next 10 years.”

    Wooof, that’s a wise way to approach it. I never thought of it like that and it totally bummed me out haha..oh dear =( Money and downturns are temporary conditions but losing loved ones is much much much much much much much harder.

  28. Paper Tiger

    Sam, I loved this post! Time well spent is more important to me than money well earned at this point in my life. Materially speaking, I have few goals. Personally speaking, I want to develop better relationships and invest in people I care about more than in the next mutual fund or REIT. I now try and focus on each day and making it really count and improving my relationships, one person at a time, as life goes on. I’m also not going to continue to waste time on fake news and fake people. I’m only letting things in my head that touch my soul and make my heart feel good. Let others complain and wallow in it if they must; I’ve now checked out of that hotel for good God Bless!

    1. +1!

      Paper Tiger, you are manifesting a mindset that I aspire to, especially “I’m also not going to continue to waste time on fake news and fake people. I’m only letting things in my head that touch my soul and make my heart feel good.”

      I loved Sam’s post too! “You learn more about your courage and capabilities from your scars, than your successes.” – Roger Crawford

      1. Amen brother, the older you get the less crap you want to take and then, if you’re lucky, one day you wake up and realize, “I really don’t have to take it anymore!” Your priorities get re-ordered around what is really important, what makes you feel good and how you can be a positive influence on someone else. It can be a tough chasm to cross but once you do, you never look back.

        1. It took me a life threatening illness at age 50 to finally admit to myself that life is too short for either toxic people (including “close” family members) or toxic thoughts. I’ve been trying to limit my exposure to both as much as possible for the past decade. It’s a continual learning process.

  29. I was part of the subprime syndicate that facilitated 2008 financial crisis. Well, I wrote the sub-prime loans trading program at one of the firms that got bailed out, and yes, right across from 6th ave of my old company was Lehman Brothers. In 2003 i noticed our loan portfolio was full of these NINA (no-income-no-asset), 0% down, IO loans, that will reset to credit card like interest rate (~15%) beginning in 3/5/7 years, aka 2006/2008/2010 the chicken will come home to roost. I hurried to find my next job not because I was afraid I’d lose it, but was afraid I’d gone to jail (the white shoe firm I worked for then use 2 layers of indirection to originate these shady loans to dogs and strippers, as you see in the movie Big Short).

    I got out in 2004 and joined an internet company pre-IPO. Yes, I got lucky twice and I don’t deserve that. In 2009 I still panic and sold half of my equities, fortunately a friend told me to get back to stocks a year later, and another friend told us to get into real-estate that same year. Our net worth has more than tripled from pre-2007 high, but not a single day I believe I deserve it. After so many crisis in my career (1995 mortgage crisis, 1997 asian crisis, 2000 dotcom, 2001/911, 2008) I’m content to live any lifestyle I choose now or what life chooses for me after the next crisis.

    Some friends had it much worse and never recovered from these crisis: marriages collapsed because stuck in a big mortgage that is under-water, homes sold at discount only to come back and doubled in values, alcoholism, old age without savings, long period of un-employment, etc..

    Capitalism can eat your humanity, even for those survivors.

      1. To stay on topic of Sam’s title: “Personal Lessons Learned Since The 2008 Financial Crisis”:

        1. Everyone can be wrong, including Nobel prize winner: while I wasn’t the only one noticed these crazy loans at 2002/2003 that will reset to credit card like rate of 12% in 2007/2008/2009, nobody in my department want to upset the gravy train. The profits was growing exponentially and everyone only care about their year-end bonus. Nobody, including the CEO want to piss off the rain-makers. Later in 2007, I think after BS went down, Paul Krugman gave a talk and insisted there were no nation-wide housing crisis, that burst my Nobel bubble right there. Apparently he was just clueless as the next expert. I learned that in life, ethical decision is often the best decisions, the guilt and sleepless nights made it easier for me to walk away from those fat bonus of 2004/2005/2006,..

        2. Skin in the game matters: all institutions eventually becomes corrupt without skin in the game. If you see the movie “Big Short”, except hedge funds guys who play with their own money, and GS partners who have their equities tied up in GS stocks, any institutions when key persons don’t have skin in the game just became actors. I see that even with my current internet company, 14 years after IPO, most executives now sell their shares as soon as vested, treating the company like an ATM, as opposed to early days when they hold on to their pre-IPO worthless shares, the behaviors couldn’t be more different. You see that in today’s America as well, when people who don’t have common fate like the WW2 generation and would immigrate to New Zealand the first minute USA got into trouble.

  30. Sam, I love your site and personal details. I also wrote a reflection on our family’s journey over the past ten yours. Four layoffs, three more children. I’m most surprised at the raw, emotional toll. There’s a reason our grandparents’ outlook was shaped by the Depression. I have a feeling we’lll still be talking about 2008 in fifty years.

  31. You may want to consider looking into Magnesium Supplements for that knee. Can’t hurt. (The Magnesium Miracle)

  32. Pretty Pretty

    Just finished Eurodollar University season 2 over at Macrovoices.

    Seems like the system is still broken. It was only the suspension of MTM that reversed the self-reinforcing meltdown not QE nor ZIRP. Bernanke could have only dropped rates down to 3% and let things sort themselves out, but now we have this epic malinvestment and bubbles everywhere with a dysfunctional monetary system that will only worsen a systemic deleveraging when it happens. The Fed will have to write Credit default swaps and IRSwaps in next crisis. It will have to guarantee collateral values to keep the banking plumbing flowing.

  33. Excellent article Sam — reflection on events like 2008 is one of the best ways to see how well (or poorly) we’ve done after a crisis. Comparisons with other’s actions since an event are always tricky. Everyone has different priorities and that’s fine. Each of us has to decide what we embrace and (hopefully) accept the results.

    For us, we made a few cuts after 2008, but never dropped the maid service. We appreciate what they do and the extra time it provides us. Some of our friends saw that and figured we must have not had a financial issue at all. Some of them bought new cars since then, but we’re still driving the same clunker!

    Thanks for the story!

  34. Damn Millennial


    What did your reserves look like ahead of the crisis?

    When you decided to build your CD’s how much cash on hand did you have? In other words if you had lost your job how long would you have been able to stay afloat?

    Agreed that being wealthier doesn’t make you happier. It does provide choices and flexibility though and that has made me happier.

    Been such a weird time in the market for a while now. Everyone talking about a crash while the market continues to perform…inevitably someone will be right, for right now S&P up 8% with 3 months to go.

    1. I had about a year’s worth of cash liquid before I would’ve been forced to sell assets. I guess if I got laid off, they would’ve given me at least three months worth of California warn act pay, and perhaps a severance. Therefore, I probably would’ve lasted for 18 months at a minimum.

      But, when you come very close to running out of money, that’s when panic will really set in, so I doubt I would have comfortably drawn down 100% of my savings. I would’ve been very tempted to sell risk assets at a discount.

      I’ve kept my current 2018 projection of +10% for the S&P 500 and 3% cap for the 10 year bond yield. Let’s see if it holds!

      How about you? What were you doing and how are you investing in 2008?

      1. Damn Millennial

        Young gun compared to you. I was oblivious to the world and just graduated high school. Saved 5k washing boats and bought a plane ticket to fly across the world to Australia to learn how to surf….not a care in the world while everything was melting down around me.

        Funny now that I think about it.

  35. It’s your former friend’s experience that is the kind of thing that motivates me. I spend time each week working on my general tech skills, while simultaneously working on my FIRE plan. I started saving too late to retire now, but retiring and living well in about 10 years is a real possibility. Of course, the market will have a say in that. Looking at valuations, it’s hard to see how they will grow much until earnings do. That’s the thing that keeps me working.

  36. I can remember how I felt after the crash of 2000 then 2008. I’ve never bothered adding up how much we lost over the 2000 crash, all I know was it was valuable in teaching some good lessons. I can’t help but feel that we have another market correction not too far away. I’ve been moving some of our funds to safer water. However, of greater concern to me is my siblings who are less financially sophisticated who do have money to lose. I’ve been encouraging them to move their retirement savings to lower risks funds to safeguard against what would be devastating if they suffered big losses. Thankfully my sister has been receptive, though her spouse who has no idea is happy to ride the wave believing it will go on forever.

  37. A lot of great stuff from the post I strongly agree with. To avoid getting too off with my response, I’ll only focus on your fourth item.

    I tend to agree times change, but people and their responses don’t. Someone much smarter than myself succinctly stated this by observing history doesn’t repeat, but it does rhyme. Applied to this discussion, the medium might change (in 2008, Facebook had just gotten off the ground, now it’s Instagram and Twitter; who knows what it will be tomorrow), but people will just find new avenues to express their displeasure, complaints, or whining. Methods of communicating continually change but the message is always the same.

    That said, you can’t control other people’s actions but you can control your’s. By aligning your behavior with your goals, I believe you will find fewer reasons to complain and perhaps more opportunity to feel grateful and content with life. I know I’ve struggled with this in the past and have been guilty of complaining and lamenting past mistakes. I’m sure I will do some more going forward, but I hope to reduce this as I make steps toward pursuing what I want out of life.

    Thanks for sharing!

  38. I wish there knew some of the things I do now 10 years ago. Career wise after market and debt recapitalisations, delisting, two new CEO bosses, dealing with cranky investors, I have learnt things that would have gotten me higher and faster quicker. And hence richer and “outer” faster as well.
    Sometimes I wonder whether I should have levered up again, after being FI and set myself on another 3 years in scenario.
    You always give good food for thought and now I am left (after reading this) wondering if I should sell the new levered property, take a very healthy upside and buy something with the profits. That would make me more FI than my spending could handle …
    Should be an easy decision but not sure why I make it so hard.

  39. So true that it really is hard to go all in when the world is falling apart around you. It would have been nice if I had bought more during the recession but it was such a scary time and I couldn’t stomach putting much into the markets.

  40. complaints are simply amplified all over social media ad nauseam!

    Amen to that. No amount of complaining about stuff on Twitter is going to fix it or change it.

    And like you, I was heavily invested during the crash but even though I knew it was a huge buying opportunity, I just couldn’t pull the trigger. I kept putting money into my 401k, but that was it. At least I didn’t sell like a lot of my friends, but it’s easy to sit here afterwards as a blogger and say “things are on sale! buy more!” When it actually happens and you see your net worth plunging, it’s a whole different ballgame

  41. By 2028 I plan on shifting to full location independence for work. Also hoping my kids are going well and we’ve shifted base of operations to somewhere with good ins state schools. I learned from the last crash that while the gettings good build something sustainable. Then while the sky is falling elsewhere you can continue to live your life. So I’ve spend the last ten years building that fortress. We shall see.

  42. My colleague at work the other day said we now need to “age-ercise” instead of exercise. At our age it’s all about maintenance!

  43. Now here’s the million (or multi-million) dollar question.

    Based on your current financial situation and what you’ve learned over the past decade, do you think you’d be able/willing to make a larger investment commitment were we to experience another recession in the near future?

    1. Recovering Engineer

      This doesn’t have to be hypothetical, what did you do in February of 2016 and Feb/Mar of this year? Both time periods saw rapid and large drawdowns from recent highs across most markets. Anybody who tells themselves, I’m just waiting for the next drop or the next time it happens I will load up on stocks, should look at what they actually did during those two time periods and evaluate if they are fooling themselves or not.

      1. I loaded up on MLP stocks in Jan / Feb of 2016. Those positions are still doing very, very well.

        Earlier this year when the market dropped in late Jan I also took advantage of the buying opportunity. This time I picked up a REIT I’d been eyeing for a few months on the cheap.

        I’ve always felt that market news (both terror and elation) are temporary. That said, the overall trend over time is up.

        I increase my positions in the market whenever I get paid regardless of what the market is doing. In times of extreme pessimism, I load up.

        My problem is always not having enough cash given the opportunities. I figure that if the market ever truly does permanently crash, you’d be better off owning guns and bullets.

        Money won’t matter.

        1. Torbjørn Enger

          I have this theory: Either the marked does good, or it does go bad. When it goes good, you dont need too much investments because getting 20% a year gives you good payment for even “small” portfolios. Example: If i have 400000dollars of investment, 20% will give me 80000 a year. Even if i save money on the side, taken into acount the height of the marked today, i just stove them away to be able to put them in when the marked goes 50% down, or i think i will go for 45% down to catch it. I dont go in at 10% down, my 400000 already gets me what i need in good times.

  44. The past decade taught me a lot of things that you pointed out. I wish I would have had the stomach to put more money into the market in 2009. Also debating when we’ll see our next pullback and will I have the foresight to invest or stay on the sidelines because I’m scared.

    I also read an article recently about how they did a study of people and everyone always says they are at a 7. No matter what their situation, people naturally always say a 7. When bad things happen, they dip down temporarily, but then come back to 7. Same with great things. I’m trying to figure out how to feel like a 10 and enjoy the moment vs. looking for something better down the road.

    1. For me, gratitude is the key. My inspirations are the books The Secret, The Magic, and The Power. I take care of my health by eating well and exercising, and that produces a glow of well being. I take care of my property and investments. In the morning, write down things I am grateful for, people I love, and things I want to create for my self. Years ago I promised myself to be happy every minute and always do want I want to do. If I feel less than ecstatic, I ask myself what it would take to feel like a 10/be happy right now and do that. Every so often I assess the 9 sections of the bagua and see what needs fixing (love/relationships, reputation, money, family/foundation, knowledge, career, travel and useful people, creativity, and well being). I expect to be happy all the time. It is totally possible.

      1. Thanks Dunny. I think being honest with yourself and asking yourself what would make you happier right now that is feasible is the right approach. Sometimes we feel trapped in our circumstances, but that isn’t really reality. I’ll think about checking out those books you mentioned.

    2. I am usually at a 10 in happiness. Didn’t used to be true. Gratitude is the key. I wake up in the morning and write a list of what I am grateful for. I always include coffee, hot water, electricity, warm bed, etc. because all you have to do is imagine waking up without these things to be grateful. Then I go on to list my good fortunes in health, money, friends, etc. Detail is important. Whenever I waiver, I read The Secret, the Power, and the Magic and look for hints and clues. My standard is to be happy every moment of the day. If I find myself unhappy, I ask what would it take to make me happy and do that. It is also important to free myself from duty and by doing that, make myself even more dutiful. When I give myself permission to not have to do something, I find I usually want to do it. I also eat healthy and exercise as that triggers the happiness hormones.

        1. Yes, gratitude is pretty amazing and producing an incredible feeling of well being. I guess that is enlightenment. Appreciating everything you have and every thing that happens. Letting bad things go pretty quickly. Not caring about much in a way, like being offended or people treating you badly. I think you have that appreciation from your writing. Working hard and getting into the zen of that. The Secret is a starting point, the Power and the Magic really get into it. There are areas I write about daily — things I am thankful for, love for myself and other people (some amazing lights go on there sometimes), and creating magnificent outcomes in my life. On a daily basis, I create a Magical Morning and a Brilliant Outcomes for my day. It’s pretty easy, and reaps results pretty fast. I may have mentioned that I review the Bagua a few times a year and make sure I have good results in each of the 9 areas.

  45. We knew the crash was an opportunity to buy more and we did. We invested and much as we could and it turned out pretty well. I’m glad we went through the dot com burst. That gave me the confidence to go all in. Now that I’m older, I’m a lot more conservative. Not sure if I can go all in like that anymore.

    As for regret, I’m with you. I’m glad I took some chances. Some of them worked out and some didn’t, but at least I tried.

  46. One man’s loss (?) is another man’s gain, and I’m glad you didn’t take that job in NY – maybe then this site won’t be what it is. This site has been an inspiration for me for almost 7 years, not only as a source of sound financial advice, but candid talk of a successful Asian-American man (because most other financial sites are not) who’s taken a less conventional road. Please keep going with your great work!

  47. I learned my lesson in 2001, so I was “sort of” ready for 2008.

    They key for me was A) keep investing hard into the 401k B) Always keep debt low C) have a plan B or side job so that you can survive.

    Passive income can be a life saver when your employment is in jeopardy..

  48. Hi FS, I really liked your post and found it inspiring!

    “I don’t want to be writing this post at 51 and saying I wish I took more adventures.”

    This. This so much! It’s so easy to fall for the trap of looking at the past instead of the future. But the thing is, you can’t change the past. But you can change the future.


    1. Yes. Almost every positive gain in my life was after self-reflection, and a comment similar to “I don’t want to be doing this when I’m 40.” I’m already planning my next career after nearly 15 years in a fairly lucrative equity stake in an IT firm.

      One key thing is to announce your intention publicly to put pressure on yourself to execute on your intention. Every time I’ve done this, I’ve been successful in my endeavor.

      1. I’m will go to graduate school – done
      2. I’m will move to California – that announcement led to engagement and a 24+ year marriage
      3. I’m will to start a business – done (sold business after 13 years)
      4. I’m will change my career at age 35 – done (lead to ownership stake – 15 years and counting)
      5. I’m going to be debt free – done (well almost… $25k left on mortgage, which will be paid off this December when I’m still just 52 years old)
      6. I will sell my IT business and launch business management consulting career – in progress… expect full transition to take another 5+ years… “But I don’t want to be running an IT company when I’m 60!”

  49. It’s easy for us to be able to see it now, but it is important in the next financial crisis that we remember that we all survived and a short time after the world appeared to be falling apart, we were all OK.

  50. Great recap of your life the past decade Sam.

    There will always be regrets and “what if” moments in anyone’s life if you look back critically at what opportunities were missed. For me it is what if I didn’t cave in to the cultural pressure to get into an awful arranged marriage that sucked 9 years of my life and cost me over a million with the subsequent divorce and her frivolous lawsuit.

    When I wrote my “I made every mistake in the book” series when I launched my blog, it actually was quite painful when I totaled the overall net worth hit I took by making these mistakes (it totaled over $2 million). If I had made every single right choice along the way I could have retired 5 years ago and be ahead of where I am now. But those mistakes sort of also turned me into the person I am now (I would probably not have seen the financial light and turn to index fund investing, etc which being at my financial bottom forced me to reassess my ways).

    You have achieved a lot you have should be proud of (as have I) and I think you have set yourself up to live a very comfortable life with the passive income streams you have built (I am not close to what you have set up, but I also do not plan on living in as HCOL area as you).

    Everyone always has the idea that they will take advantage of the next sell off and stay the course, but until you experience the actual environment when the world seems to collapse it is hard to put into reality.

    I didn’t take as much advantage as I should during that time periods as well but it was only because I was mired in a very bitter drawn out divorce and was hemorrhaging money with legal fees etc (I spent over $300k legal fees in the year it took me to divorce). So I unfortunately did not have the spare money I would have had to really set myself up.

    I am glad Financial Samurai came to being during this time, who knows if you never were motivated to start it if things weren’t crashing around that time.

    1. Striking while the iron is hot is a lot more difficult than it sounds. Everyone plans to take advantage during a downturn and scoop up equities on the discount aisle. However, as Mike Tyson said, “Everyone has a plan until you get punched in the mouth.” That punch could have been your painful divorce. It could have been fear keeping you from pulling the trigger. It could have been any number of things that complicate life. You can’t control the contributing factors, just your response. In the end, you hope to learn something along the way or you turn out as a better person.

      I’ve found the best way to be successful is to minimize mistakes and have your smaller wins compound to land you in a better place. Imagine combining these small wins with Sam’s mentioning of taking an extra hour per week over 10 years to dedicate to something meaningful. Imagine what talent, skill, or ability someone could develop in that found time.

      This is a long way of saying that I agree with your summation that mistakes happen and they make you into who you are. By minimizing your mistakes and investing in what matters to you, it shouldn’t matter when you start something, just that you start at all. Time in your investments matters the most. Don’t live with regrets motivating your decisions. Operate out of confidence and purpose, not fear.

  51. It is a shame to see in how many occasions we wait for bad things to happen to us before we actually spring into action and do the things we want to do. In your case it was the prospect of losing your job while having a big mortgage, for others it could be a bad medical diagnosis, an accident, a loved one passing away etc.

    We would all be infinitely better off by just doing what we want to do, when we want to do it!

    1. As Bernstein says when you win the game cash in your chips
      Pre retirees need to avoid sequence of risk

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