To Get Luckier, Realize Success Is Mostly Luck


How to gain more luckI live by the mantra, “Never fail due to a lack of effort because hard work requires no skill.” It’s a reminder to STOP making excuses when something seems too daunting to tackle. There’ve been too many instances when I didn’t start something because I felt I lacked the skills necessary to succeed. I’ve regretted each non-action.

For example, I postponed starting Financial Samurai until 2009, three years after first contemplating the idea, because I didn’t know whether or not I could write anything insightful. I also didn’t know how to start a website, despite the easy availability of free instruction. The delay cost me over a million bucks.

For those of you who want more luck, I strongly believe the more you attribute any success you have to luck and mean it, the more luck will come your way. Why? Because you won’t take your luck for granted. Gratitude is what will keep propelling you forward. Let me explain by strolling down luck lane. 

First, A Reminder About Luck

Here’s the latest reminder to keep the ego in check from a comment left in the post, The Downside Of Financial Independence. I ended the post with the importance of working hard to not dishonor the generations before us who laid the foundation.

On generational wealth, I think people, and successful people especially attribute much of their success to hard work. The fact is, random chance plays much more of a part than we would like to admit. If our grandfather worked 18 hours per day to earn his fortune, there are likely 10 other grandfathers who worked the same 18 hours per day but never became wealthy.

I am moderately successful and sure I work hard. But so do most people. I am successful because early in my career, a hiring manager decided to take a chance on a smart ass kid. Had that not happened, my trajectory would be completely different (for better or worse).

In other words, all our ancestors emigrated at some point. All had to work hard to get ahead. Some got farther than others. Therefore, my great grandparents were simply luckier than others to establish homes and raise families in Taiwan and Hawaii, respectively.

The instant you start telling yourself that most of your success is due to hard work is the instant you start losing your lucky momentum. It’s important to recognize some of your life’s luckiest moments in order to rid yourself of attributing success to hard work. Only with humility will you be able to generate more luck in the future.

Three Lucky Breaks

1) Meeting my wife in college. Life is easier with a life partner. But some folks don’t find their soulmate until later in life. Some never find someone. I was extremely lucky to meet my wife when I was a senior in college. It was unexpected because I was 100% focused on getting a job. She wasn’t on my radar junior year because was was still in high school then.

As my focus was to free up time for job interviews, I took fluffier courses like Advanced Golf and Japanese 101. Hooray for a Liberal Arts education that taught me how to build relationships over four hours on a golf course with important people! Even better was Japanese 101 because that’s where I met my wife.

My original purpose for learning Japanese was to become proficient enough to charm female tourists while back home in Hawaii. I also thought I’d be able to get an easy A just chilling in the back row. Instead, Japanese 101 was the first course I ever got a D on a test! It was a beautiful D, however, because my future wife offered to help me with my studies.

Meeting my wife at William & Mary was 100% luck! She could have very easily decided to attend UVA in Charlottesville where her mom worked.  Luckily for me, she chose William & Mary instead because she wanted a more intimate classroom setting. UVA’s 20,000+ student population at the time was 5X larger than William & Mary’s. Further, we couldn’t have met at UVA because I was only wait-listed. So in a very large way, I owe William & Mary a massive debt of gratitude for taking a chance on me.

My future wife was the one who called me at 5:30am to make sure I’d get to my 8am interview on time back in 1998. She was the one who consoled me after each job rejection. When I moved to San Francisco in June 2001, she decided to graduate six months early to join me that December since I hardly knew anyone. In late 2014, she negotiated her own severance package to keep me company during early retirement. Now she’s the COO and CFO of our little lifestyle business.

Having a best friend to experience the majority of your life with is truly lucky.

2) Getting a job offer from a major investment bank in 1999. I began interviewing with Goldman starting in 1998 at a finance career job fair in Washington DC. It was a pretty cutthroat environment with a lot of go-getters from some pretty good schools like Georgetown and Duke. One female recruiter from Merrill Lynch even looked down on me for wearing a teddy bear tie holding a balloon that my girlfriend gave me. Thanks a lot you cold-hearted wench!

Seven round trips from school to NYC, 55 interviews, and two weeks after graduating from the College of William & Mary in May 1999 later, I finally got an email offering me a job. It was so very exciting.

It would be easy to attribute my getting a job at a major investment bank to my interviewing skills and perseverance. But the fact is, if I had interviewed better, I might have gotten the job offer much quicker! When I spoke with my incoming colleagues, I learned that the average number of interviews they’d had was about 15. In other words, having undergone 3.5X more interviews, clearly I was lucky to get through the gauntlet.

Further, no one else from William & Mary got a job offer from GS that year. Nor did anybody get a job offer from GS the year prior. The only reason I was given the opportunity to interview was due to a GS recruiter named Kim Purkiss who selected my resume at the career fair. She fought for me during the recruiting process, and I owe so much to her.

If I didn’t get a job at GS, I wouldn’t have bought VCSY in early 2000, the multi-bagger stock that grew from $3,000 – $150,000 in six short months. Without VCSY, I wouldn’t have felt comfortable buying a $580,500, 2/2 condo in Pacific Heights a couple years later that has now doubled in value and commands $4,200/month in rent with no mortgage.

Without working in finance for the past 13 years, I wouldn’t be able to write about investing, real estate, and retirement with ease. And without Financial Samurai, I’m not sure whether I would’ve left my job in 2012 because I wouldn’t have known what to do with all the free time.

3) Financial Samurai to 1 million organic pageviews a month. Starting a website is easy. Growing a website is the fun and hard part. I do believe most people who publish 2 – 4X a week without fail for three years will be able to generate a livable income stream online e.g. $2,000 – $5,000/month. However, only a lucky few can get to 1 million organic pageviews a month without any advertising, a forum, or public self-promotion.

Financial Samurai featured in many major media publicationsMy lucky break came in 2010 when The LA Times money columnist, Kathy Kristof highlighted my post, Get An Umbrella Policy, Your Teenager Is Going To Bankrupt You. It was just an average post, but it was relevant to Kathy. I met up with Kathy at a conference in 2016, and she said at the time, she had a teenage son who she always worried about. Therefore, the post really resonated with her when she was perusing personal finance blogs to highlight. Talk about 100% luck!

Once The LA Times featured Financial Samurai, other large media organizations began following suit. The more large media organizations highlight your work, the more credibility and traffic you get. Now the badge of honor is jam packed with media mentions eight years later.

One of the more recent lucky breaks was when social media got hold of Scraping By On $500,000 A Year. That came out of nowhere because I wrote the post in 2015. Because that post was viewed several million times, it provided a shift up in traffic that I’m still experiencing months later.

Even more recently, Yahoo decided to highlight The Dark Side Of Early Retirement on its homepage. How cool is that? For website owners, this is kind of like winning the lottery. Companies literally spend tens of thousands of dollars a month with PR companies to to try to get this type of exposure. And here I was getting it for free without having to pimp myself? It’s complete luck to let featured and have my writing stand on its own! From this feature, traffic doubled for several days, bringing in new readers along the way.

Financial Samurai On Yahoo Front Page

So how did this lucky break occur? An editor randomly reached out and asked if she could republish the post and I told her, “Of course! Take everything and my little pony too!” Perhaps the editor reached out because she noticed the Scraping By On $500K post from the month prior since the post talked about a New York City couple and the editor currently lives in NYC as well. Who knows! But I didn’t ask because I didn’t want to annoy her.

There are many far better writers with much longer writing careers who’ve never gotten featured on the front page of Yahoo. I’m definitely not as deserving as so many other people.

Don’t Take Your Luck For Granted

I used to believe success was around 50% luck / 50% hard work. Now I believe success is closer to 80% luck / 20% hard work. We can’t control the 80%, but we can control the 20% so we might as well try. To take my luck for granted would be to dishonor the millions of other people out there who are not as lucky.

The longer you work at your craft, the luckier you’ll get. You just have to be patient, like the fisherman who sets up his station every morning without fail, hoping to reel in the catch of a lifetime.

Finally, I do believe in karma. The more we can do to help other people, the luckier we’ll get. I wish each and every one of you the best of luck. And when you get a fortuitous break, don’t forget to share!

Note: There is a poll embedded within this post, please visit the site to participate in this post’s poll.

Related: Grow Stronger By Humbling Yourself Each Year

Readers, what kind of lucky breaks have you had in your life? What are some of the things you’ve incorrectly attributed to hard work that in reality were mostly lucky?