How One Lucky Financial Break Can Change Everything For Good

I firmly believe that above-average wealth is largely a result of luck – around 60% – 70%. If we fail to recognize our lucky financial breaks, we risk confusing our abilities with good economic times. This overconfidence can lead to poor decisions and increase the likelihood of financial ruin.

Since starting Financial Samurai in 2009, I’ve witnessed fortunes rise and fall. Time and again, hubris during good times proved to be people's undoing. I experienced it firsthand in 2007 when I assumed my income would keep climbing. That misplaced confidence led me to purchase a vacation condo in Lake Tahoe, tying up 30% of my net worth in an asset I didn’t need. Over the next three years, the condo’s value collapsed by 50%. Oops!

Times are great again, and nearly every asset class has performed well in recent years. It’s tempting to chase even greater returns to ride the bull market higher. If you choose to do so, proceed with the understanding that every bull market eventually ends—and often not gently.

Be Thankful For Your Lucky Financial Breaks

As the year comes to a close, it's a great time to review how your net worth has performed. To truly appreciate the progress, look back three, five, and ten years. For those who have consistently saved and invested a portion of their income, you’ve likely witnessed the magic of compounding!

While it’s important to celebrate financial growth, it’s equally important to recognize the luck that helped along the way. If we do, we will feel happier and more appreciative.

Let’s reflect on some lucky financial breaks that keep us grounded and humble. Here are five past and recent fortunate events that have shaped my life. I hope you will share some of yours in the comments section below.

Lucky Financial Break #1: Landing a Good Job After Graduating From a Non-Target School

My luckiest professional break was when a woman named Kim Purkiss selected my resume from a sea of thousands at a career fair in Washington, D.C., in 1998. Kim was a strong, determined Black woman who grilled me like a sausage during our interview.

Coming from William & Mary, a non-target school, I kept getting passed around the various desks at Goldman Sachs in NYC. Yet, Kim continued to advocate for me through seven rounds and 55 interviews until I finally landed a position in International Equities.

Once I secured the job, I worked hard to prove myself. But I was young, unpolished, and made mistakes—like overindulging in day trading. Unfortunately, the Dotcom implosion in 2000 didn’t help my case as the firm began cutting staff.

Looking back, I wouldn’t have even gotten my foot in the door without Kim’s persistence and belief in me. Her advocacy was a stroke of luck that set my financial journey in motion. Thank you Kim!

Lucky Financial Break #2: Investing in a Chinese Internet Company That Went Gangbusters

Before I wasn’t invited back for a third-year analyst position in 2001, I had one of the luckiest trades of my life: identifying a Chinese internet stock called VCSY. Its homepage featured a dial pad, where each number led to a different subject matter. With stocks like Yahoo and Ariba skyrocketing at the time, I figured Chinese internet stocks would be the next big opportunity.

I invested $3,000 into VCSY, and within three months in early 2000, it surged 60X to $180,000. Part of this meteoric rise was because I worked on the international desk and shared the idea with peers on the 49th floor, including traders. I also mentioned it to colleagues at Morgan Stanley and JP Morgan, and the buzz spread like wildfire.

Ultimately, I sold the stock when it was worth about $150,000. Luckily, I held most of the proceeds in cash as tech stocks began to crash soon after. This windfall gave me some much-needed financial stability as my career prospects took a hit.

Ultimately, 85% of my VCSY gains after tax were rolled into a San Francisco condo I bought in 2003. This was the start of my love affair with owning real estate – it generated income and its value wouldn't just go *poof* overnight, like VCSY's value did over the next two months.

Lucky Financial Break #3: A Helpful Advocate Prevented Unemployment

Elaine, a VP on my desk, played a pivotal role in saving my career. She was one of my biggest skeptics during the hiring process, even insisting on meeting me a third time for a coffee before making a final decision. Although somewhat intimidating, she became a mentor of sorts once I joined, and we bonded over our shared love of skiing.

Elaine often shared stories about the fascinating people she met on ski trips. As a single woman in her mid-30s, she was trying to balance her demanding career with her personal life, shifting her focus toward dating. I became her confidant during that period.

One day, a recruiter named Michael, who had a nervous voice, called Elaine, hoping to recruit her for a role at Credit Suisse First Boston. She wasn’t interested but told Michael to hold on and handed the phone to me.

This moment was serendipity. Elaine knew my future at Goldman was dim. If she hadn’t handed me the phone, I wouldn’t have secured a role at CSFB in San Francisco in June 2001—with both a raise and a promotion. That break kept my career afloat and gave me a fresh start for another 11 years.

Retiring in 2012, just as the bull market was starting to take off, was also lucky. Each year of rising investment values increased my likelihood of staying free. It's better to retire in a bear market. This way, your finances and resolve will be better tested.

Lucky Financial Break #4: Spared by Google Algorithm Changes

In July 2009, I started Financial Samurai, partly out of fear of losing all my money and getting fired during the financial crisis. It was also a joy to write and watch the site grow through effort outside of work hours. After several years, the majority of traffic to this site came from Google.

When I left my job in 2012, for over 10 years, I have expected Google to eventually ignore Financial Samurai after one of their countless search algorithm updates. It’s a natural expectation after witnessing so many great independent sites disappear over the years. Yet, against poor odds, this site has continued to chug along, like a trusty tugboat navigating stormy waters.

From King Of The Hill To Minimum Wage

I feel especially grateful for this financial break after catching up with a friend who also runs a site. He recently hired the co-founder of another once-thriving site to handle sales for him. The base pay was minimum wage plus a percentage of revenue.

I was floored. That site, which had been around for over a decade and once regularly boasted over a million pageviews a month, is now a shadow of its former self. Due to Google’s algorithm changes, their traffic is down 90%, and the co-founders have had to pivot to stay afloat.

Now, I feel like my old-school approach of writing three posts a week myself with real-life stories isn’t so shabby after all. Although I constantly feel like the tortoise lumbering along against hundreds of darting hare, the enjoyable pace lets me earn supplemental retirement income, which I primarily reinvest in stocks and real estate.

Lucky Financial Break #5: Being Able To Invest In AI Near The Beginning

For years, I’ve treated my online income as “funny money”—a bonus that I didn’t rely on but instead saved and invested. Much like how rational people save or invest their tax breaks when they suspect the cuts might be temporary, I’ve been consistently funneling my online earnings into real estate and stocks. After 15 years those investments have grown thanks to a long bull market.

Now, AI presents another incredible opportunity to invest early in a transformative trend. While our children may not yet have the means to invest in AI today, we can invest on their behalf—and I feel a responsibility to do so. In 25 years, I don’t want them asking why I didn’t seize this opportunity, just as my dad once questioned my grandfather for not buying prime oceanfront Waikiki property when it was affordable in the 1950s.

Ironically, I expect AI to also hurt Financial Samurai by scraping my content and reproducing it without attribution. Then I expect AI to wipe Financial Samurai off the face of the internet, even worse than my expectations I have for Google. It's funny how history tends to repeat itself if you live long enough.

Holding Onto The Final Years Of Existence

Since I can’t beat companies like OpenAI and Anthropic—with their deep pockets and armies of talent—I’ve made them work for me. I’ve invested in them and other leading AI players through venture capital funds, creating a hedge against the potential loss of online income. My goal is to invest enough in AI so that the gains from these private investments will surpass my online income over time.

Despite this site's existential crisis, I’m cautiously optimistic that Financial Samurai can survive three more years, giving me until December 31, 2027, to reach my goal of full financial independence once again. If it does, I’ll be incredibly grateful for this final chapter in my journey. If the site doesn't survive, then what a nice run it's been helping over 100 million people achieve financial freedom sooner.

While it feels bittersweet to envision Financial Samurai’s potential end on December 31, 2027, it’s also liberating. A new chapter awaits—perhaps solely as an author or a 50+-year-old pickleball professional!

Related: Perpetual Failure Is The Reason Why I Save

You've Got More Lucky Financial Breaks Than You Realize

Take a moment to reflect on your lucky breaks. It’s easy to overlook them and attribute success solely to hard work and determination. Yet, a single fortuitous event can dramatically alter the course of your life. These moments are often the silent drivers of your journey—don’t take them for granted.

Let's make the most of every opportunity our luck brings! Even if luck accounts for 70% of your success, that still leaves a meaningful 30% where you can try extremely hard. Thank you for reading, sharing, listening, and contributing over the years. It’s been a pleasure to connect and grow old with so many of you.

Readers, what are some lucky financial breaks you’ve experienced but may have overlooked? Is it inevitable to downplay the role of luck and overemphasize hard work and ingenuity in our success? How can we avoid confusing brains with a bull market so we—and our children—remain grounded and appreciative?

Investing In Artificial Intelligence

If you're looking to invest in private AI companies, consider Fundrise Venture. Unlike closed-end venture capital funds, the Fundrise venture product allows you to see most of its investments before committing capital. With a low investment minimum of just $10 (compared to $100,000+ for traditional venture funds), it offers accessibility for a wide range of investors.

Fundrise Venture Financial Samurai dashboard and investment amount - Investing in my financial lucky break now before the IPO window opens
My Fundrise Venture dashboard

I recently invested another $5,000 into Fundrise Venture and plan to continue doing so for years. My goal is to capture potential liquidity events in the coming years, driven by acquisitions and IPOs. To do so, I'm building my position now, because such liquidity events are lumpy and take step functions up (or down) in price.

AI's transformative impact is already evident—my dad lost his editing job, and my content is frequently scraped. These experiences reinforce my belief that AI will continue to disrupt various industries and reshape the labor market. My hope is that when my kids become adults, they will recognize their lucky break of having a dad who could invest for them.

Fundrise is a long-time sponsor of Financial Samurai, and I'm an investor in Fundrise. Remember, returns are never guaranteed, so always invest at your own risk based on your financial goals and risk tolerance. You can join 60,000+ others and subscribe to my free weekly newsletter here.

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GottaRead
GottaRead
20 days ago

Some of your financial breaks seem to come from the people who have been in your orbit. Any advice for creating those types of environments and cultivating?

Andy S
Andy S
1 month ago

The luck I’ve had over my life has been incredible. Financially, I’ve been lucky to have experienced one IPO for myself, one for my wife, and a startup acquisition for myself that paid out even better than the IPO. Each event was like winning the lottery. I’ve also had the luck of timing in buying a home in the SF Bay Area right after the Great Recession (2010), as well starting my career in Silicon Valley in the late 90s. I was even lucky in the universities I attended, getting into schools where the average student was way smarter than me. The only unfortunate part of being so lucky is that I have no way to teach my kids how to replicate my success in their future. Still, reminding myself of the extreme fortune I’ve had makes me quite grateful and happy.

Al Corrupt
Al Corrupt
1 month ago

I totally admit luck had a great deal to do with being financially healthy. If I hadn’t been in the right place at the right time, I wouldn’t have been able to invest in a start up. I do have to point out that being able to do the investment was because I had saved for years and was prepared to make an investment. You need to have the resources to take advantage of opportunities.

Stephane
Stephane
1 month ago

Thank you for your articles and your work here,

Unfortunately, I can’t have the same feeling as you, because like most people I didn’t have any help from anyone, but I had some lucky breaks on investments when no one believed in it (the luck of timing).
But you forgot other essential chances that you had: loving parents who gave you a nice sum of money for your studies, which you finally invested, a financial help from your grandfather to be able to get the credit for your first big property (house), all this helped you and it’s very good for you, that seems normal for you, but unfortunately many have not had this luck.

Stephane
Stephane
1 month ago

Yes sure, luck plays an essential role in increasing wealth.

Oke I understand, you had cited some very good examples.

Indeed a very difficult family (violent, prison and psychiatric internment of my father, etc.), at 18 I had 0 € in my accounts, my parents had taken everything to be able to eat and pay the bills, when I was young there was not always enough food in the refrigerator, but I helped my parents who were over-indebted. Life in France is not an easy life, on paper yes, but not in reality (few government help and other in fact at the time 80’s start 90’s), but I do not complain, it is part of my life and I have become stronger thanks to it, and I have outperform my wealth goals (28y begin in invest., retirement definitive à 38 y), so all ends well.

I travelled a lot in the world, and even in the United States I have seen in Oct-Nov 2023 of Hawaii (waiikiki beach too) to New York people in big distress in the street, hard and complicated lives, there are plenty of them. But nothing is wrote by advance, we can sometime change the things and fight bad fate, like me with of the chance.

Thank you for your work and your articles!

observer
observer
1 month ago

My luckiest break is having been able to migrate to U.S legally and with my family. Being sponsored by an uncle who made it in Silicon Valley. People do not understand what a privilege is to have an American passport and live in the United States. After that everything came through hard work to me and my siblings.
Well I was able to buy my house in 2013 during the downturn and then refinance it when mortgage rate were dirt cheap.
I also was able to find a job with pension in my own field, which is a huge break..
My parents really got lucky that they were able to buy a property in Silicon Valley ( south bay), some 20 years ago.

Chris
Chris
1 month ago

I was born in Africa during a period of war, to refuge parents from Europe. My parents relied on the notion of savings and never borrowing, only bought for cash meaning they could afford it.
I hustled in my early years, buying and selling (foodstuff, clothing etc) and breaking bulk flour, sugar, to opening retail stores, fast food outlets, clothing stores etc.
I got a lucky break, in 2010, through a government tender in the utilities space and that propelled my property obsession and currently am living the life similar to you Sam (i even coach tennis) with my investment covering my expenses and allowing me to save and reinvest in start ups and my own businesses.
Most importantly, I spend as much time as I can with my 10 and 6 year old boys.

ps i obtained a law degree as well but never practised post my admission, I have only ever received 22 pay checks in my entire life. im 46.

Chris Pavli
Chris Pavli
1 month ago

The company profits and living frugally allowed me to purchase a property every year since and make investments.
My only regret is that I am not invested in the stock and bond market. This is probably attributed that this is not a strong asset class in Africa and with geo political risks and currency fluctuations, bricks and mortar are the only safe havens.
Unfortunately, very difficult for non US to invest in America. I have tried the fundrise platform and others but only opened to US citizens.
Is there any products you know where foreigners can invest in?

Jean
2 months ago

I certainly haven’t planned my life based hoping for luck. Sometimes the best things do happen when one hasn’t planned it perfectly or not even aware of what may happen soon.

I am a latecomer in personal financial investment (except for owning a condo and then selling it 14 yrs. later while living in this home.) I seriously didn’t investing unti less than 15 yrs. ago. I just retired @65 yrs. last yr.

So there is some “luck”, by buying 1-2 good stocks and I sold only tiny bunches, to reinvest differently. But alot of other things is due to me seeking job opportunities, working diligently yet enjoying time with my partner …when he was alive.

Joe
Joe
2 months ago

Love this post. I was 10 or so and visiting family in Alaska. The type of place in Alaska you can only fly or boat up a river to. Families lived in plywood and sheet metal homes with no utilities. I could go on.

It was my first realization of being lucky in life, in a lot of ways. I think I’ve slightly over performed my financial prospects relative to my starting point

There are some truly difficult starting points though and you have to be all that more lucky to get even, let alone ahead.

Great reminder how lucky many of us are

Corey
Corey
2 months ago

I just finished a book, which I will not name, but I suspect you are familiar with, that talks at length about how we tend to underestimate the role of both luck and risk in our financial lives. It also talks about how, as you rightly point out, the outsized effect a few winners have on your success. As I look back on my career, I can see where sheer luck created certain situations-some of the luck was good, some bad.

Mark
Mark
2 months ago

I think you way under-estimate the amount luck contributes to our high net worth. It is not, in my opinion, 70%. It is more like 99%. Afterall, we were born in a wealthy first world country. Had we been born in Africa………..? For all of us here, our huge piece of luck came on the day we were born…….. Everything else is minor in comparison.

Adam R
Adam R
2 months ago
Reply to  Mark

You are absolutely right, but most people will never admit to this due to their ego. You can provide all of the examples and facts you want, but they will fight you on it to no end.

Adam R
Adam R
2 months ago

At a minimum 75%, so I’m definitely in line with your thinking.

AJ
AJ
2 months ago

Financial Samurai, forever and forever, a hundred years Financial Samurai, s… things. Me and Financial Samurai runnin’ around and Financial Samurai time. Aaall day long forever. All, a hundred days Financial Samurai forever a hundred times. Over and over Financial Samurai dot com W W W dot Financial Samurai dot com W W W Financial Samurai adventures all hundred years. Every minute Financial Samurai dot com W W W hundred times Financial Samurai dot com.

…here’s hoping that it’s way more than 3 years ;)

Drybred
Drybred
2 months ago

You had some really great people looking out and blocking for you.

I find that most, not all of course, highly successful people are also very generous with their time and insights, and this quality generates an unstoppable positive feedback loop.

Thank you for the excellent content!

Nick G
Nick G
2 months ago

Hi Sam, thanks so much for the reminder on this perspective! At 27 years old I have been investing since I was 20. I made all sorts of mistakes in what not to invest in, but eventually found my way to low-cost index funds – which have helpfully compounded for me. But my lucky break was all thanks to a meme and a Twitter account – $90 in DOGE coin turned into $4,500 and that helped pay for our first house! Now we are about to close on investment property #4 and #5 later this month, and are closing in on 6 figures in our combined investment portfolio all thanks to continuing education (especially Financial Samurai!) and saving/investing til it hurts.
Thanks for all you do!

Tom
Tom
2 months ago

“Chance favors the prepared mind.” – Louis Pasteur, 1854.

“I can’t afford to believe in luck.” – me, 2024.

Man, I’ve done some dumb stuff, really dumb, like lost 7 figure money dumb, and that’s just financial idiocy. My bumbling ineptitude is richly multifaceted and grows with each day I’m alive.

I’ve also done some smart stuff, really smart, like made 7 figure money smart, and that’s just financial smarts. I intentionally end each day with more intelligence than I started the day, and over time, those nuggets of smarts occasionally connect to form a mysteriously revelatory gestalt that feels like brilliance. Eureka! Something good happens.

If I only have to win 51% of the time to be successful, I’m doing ok. But I say I can’t afford to believe in luck for the same reason I say I can’t afford to believe in any religion – if I believe in one religion’s heaven, I’m doomed to all other religion’s hells. If I believe in good luck, I’m doomed to believe in bad luck – both based on chance versus my choices.

I can’t afford to believe my success or failure is largely a result of chance, luck outside of my control, because I’m naturally lazy. By attributing the good or bad in my life to fickle fortune, I demotivate myself. Why try if the results of my actions are determined more by luck than logic?

Maybe I’m just a masochistic control freak, but I like a world in which I’m accountable for my choices and accept credit for both good and bad results, along with the fellow geniuses or idiots who helped me get those results. Of course, stuff happens outside of my control all the time, but I still get to control my reaction to good or bad surprises.

As I used to tell the folks in a former job in crisis management… “Whatever happens, happens. We’ve done all we can to prepare, so now we stick to the plan, stay calm, and carry on. Good luck!”

Tom
Tom
2 months ago

True! I like the nature vs nurture comparison to lucky vs earned.

Your example made me laugh as I happen to be a tall person, which often felt lucky until I lived in a country built for short people. I’m pretty sure my forehead is permanently dented. Luck can be nuanced and situational, and can even flip on you – what started as good luck can turn bad and vice versa.

That said…of course I’ve had lots of luck in my life, both good and bad. Everyone has. My beef with “luck” as a reason for success or failure is when I think accomplished people are overly downplaying their good decisions by claiming much of their success is just luck, or when I think folks in dismal circumstances are dismissing accountability for a string of bad decisions by claiming their misfortune was just luck. We often deserve more credit.

I’ll accept and share all the good stuff I can get, whatever we choose to call it!

Untemplater
2 months ago

Luck has a funny way about it. But I do believe a lot of things do come down to luck. Hard work and determination are big factors as well. But luck is definitely a factor. I like to take this time of year to think about my lucky breaks as well while I’m going through my list of things I’m thankful for.

Dave
Dave
2 months ago

I hate the luck narrative.

Dave
Dave
2 months ago

The on feature did not make or break me. Is it luck that I took advantage of that option while most of the others in my department (that sit within a BB bank) did not?

I see too many consistent traits in people that make them successful to believe all success is based on arbitrary luck, good or bad.

Being a good person, intelligence both OQ and EQ, hard work, being prepared, having a positive outlook, learning to overcome adversity, etc…

Dave
Dave
2 months ago

We can respectfully agree to disagree

Dave
Dave
2 months ago

And I said I hate the luck narrative (not luck itself)

Liam
Liam
2 months ago
Reply to  Dave

I suspect you prefer the fictional “muh harrrd wurk!” narrative.

Dave
Dave
2 months ago
Reply to  Liam

I prefer to believe life is the result form a compilation of choices we make during our life. Does that mean luck doesn’t play a part? Of course not – but I also don’t think that’s the only variable that matters…

George
George
2 months ago

I bet 10 years from now, people will tell those investors in AI that they got lucky investing today, even though they could’ve invested right now.

I’m also investing about 10% of my investment assets in private AI companies. It is obvious there are gonna be plenty of winners over the next 5 to 10 years.

Here’s to getting lucky again in the future!

Roger Ezell
Roger Ezell
2 months ago

Dennis Weaver stated on The Tonight Show decades ago, “The harder I work the luckier I get.”
There is an abundance of opportunity.

Bill
Bill
2 months ago

Although it may be humble to attribute these successes to luck I think it’s disingenuous. If I remember correctly you were one of the only people to show up to the job fair. If luck played a part you were lucky that a bunch of other qualified people didn’t show up. Next, I would expect someone in international equities to pick a 60 bagger during the dot com bubble. Your lucky part was selling before it went to zero, not picking some random stock that went up. Having a mentor refer you to a new job happens all the time. No luck there. The google thing I have no idea how their algorithms work so maybe you can attribute that to luck. Who knows. Investing in AI, that’s just smart, not luck.

You’re not luckier than anyone else. You put yourself in a position to succeed and you did. Lucky is being born in a country that afforded you these opportunities. The rest is up to us.

Bill
Bill
2 months ago

I don’t believe in luck as you present it. I believe in math and probabilities. For example, is it lucky I bought Nvidia because I saw the shift to the cloud and then AI hits and the stock goes wild? If you do then it was bad luck when I took all my wife’s and mine wedding money and bought National Auto Credit because I thought the symbol, NAKD, was funny and I lost it all. Saying one was luck or the other was bad luck excuses my responsibility for my decisions.

I

KO
KO
2 months ago

My lucky break #1, buying Apple stock in 2004 and holding on to it.

Lucky break #2, buying a vacation home in Lake Tahoe, LOL. We sold my condo in downtown San Jose and bought the Lake property in 2018, then Covid-19 happened. Property values in the lake area doubled and we had an escape location away from the virus. Meanwhile my old condo is valued at approximately what it sold for in 2018

KO
KO
2 months ago

I have retired, or more accurately, I gave up finding a new tech job after quitting in 2015.

Then in 2022 I found our “forever home” and bought it with a large chunk of the Apple stock, significantly reducing my dividends and causing me to redouble my investing efforts and consider un-retiring. My partner works and we talk about if I should get a job.

Does this sound familiar? LOL

Lee
Lee
2 months ago

If you were looking for a job at an AI company which ones would you be most excited to work for?