Personal Lessons Learned Since The 2008 – 2009 Financial Crisis

On September 15, 2008, Lehman Brothers went bust. I remember this day clearly because I made a $200 side bet with my friend over the weekend that the US government would bail them out. To my surprise, the US government didn’t rescue Lehman, and the stock cratered that Monday and never recovered.

Despite all the economic devastation, I wouldn’t mind rewinding time and going back to 2008. I’d rather be 31 than 42, simply because I love life and want to live as many years as possible.

As we potentially head into another recession due to the coronavirus locking up economic activity and the collapse of oil prices causing tremendous job loss in the oil & gas sector, here are some lessons learned during and since the financial crisis.

Lessons Learned Since The 2008 – 2009 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% at the time, so I decided that was where most of my savings went.

The only things I did right were keeping my job and not selling any real estate or stocks in the middle of the downturn. Today, earning 1.75% in an online savings account looks attractive now with thee 10-year yield at only ~0.5% and stocks are plummeting.

Events leading up and through the 2008 financial crisis

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

2) Chaos is a great motivator to change.

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?

3) Family is everything. 

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. Good thing 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.

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.

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

4) You gain a tremendous amount of confidence in 12 years. Previously, I’d always been embarrassed to ever say I was an expert in anything. But once I turned 32, I felt I had developed some expertise in the Asian Equities market. And now that I’m past my 10th year of building Financial Samurai, I have no problem believing and saying I have expertise in digital media and personal finance.

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.

5) The more things change, the more things stay the same. I met many disgruntled people before 2008 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 at work who made my breakfast bagel each morning.

12 years later, we still have the same complaints. Yet, instead of losing money in dotcom stocks or housing, it’s losing money in cryptocurrencies or marijuana stocks. Instead of hearing complaints about other people’s problems in person, complaints are simply 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.

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.

As I look through the years to 2008, my main regrets are 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. For the last two, better late than never.

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. I had been too comfortable at my then job and had used my house as an excuse to stay. Given I left my job two years later, not getting that last bit of extra cash was a mistake.

Given this regret, I’ve learned to try more things such as coach HS tennis, be a foster kid mentor, write and copyright a song, create a podcast, and attend more events. The biggest thing I want to try now is to leave San Francisco and relocate to Honolulu once my boy is eligible for kindergarten in 2022. This will be a significant move since we’ve been here since 2001.

On the positive side of not leaving for a new firm, I was able to negotiate a really nice severance package given I had been with them for 11 years. If I had gone to the new firm, I might have been stressed out of my mind, and may have sold my house in 2012 instead of in 2017 for much more.

7) Even if you see the future, it’s hard to take advantage. During the first year after leaving, 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 because I thought it would be a big hit. But 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 $3 million today since Airbnb is valued at around $38 billion.

Today, I strongly feel that 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, I will continue to do as much research as possible to figure out the best investments possible.

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 because 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 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 be up about 90% if you had held on to today. Add on dividend reinvestments, you’d be up much more. 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. With the amount of uncertainty in the economy today, real estate is probably going to be a strong outperformer this year up to a point.

Unfortunately, these past 12 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! Spend the time to do more stretching and warmups. It’s not worth going all-out in sports anymore due to injuries.

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 strongly in common or a corporate card!

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. Therefore, I plan to spend more time with my loved ones than in the past, especially now that I have a new addition to the family.

11) Being wealthier won’t make you much happier. Most of us have more than doubled 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 7.5 – 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, 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 $80 parking ticket or having to eat less to save on food expenses. 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, volunteer to help others, and write things out. If you don’t want to start a site, at least start a gratitude journal.

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 made, you can’t help but want to make more. As a result, you end up taking unnecessary risk.

Over the years, I have received plenty of pushback from all-in equity investors whenever I write about investing in bonds or structured products(subscribe for more info) that hedge against downside risk. Going through the 2000 and 2008 downturns were enough to make me realize that the good times never last forever.

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

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.

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 10 years. But at least we made a good amount of money while the good times lasted right?

Over the next 10 years, I plan to focus most of my time on being a present father. 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 just want to keep what I have.

Readers, what are some lessons you learned during the previous financial crisis that is helping you live a better life today? 

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