Are you an underdog looking to succeed in this brutally competitive world? Do people ignore you, discredit you, think you’re dirt, or even hate you for just being you? Well, welcome aboard!

I’ve been the underdog my entire life. The number of rejections I’ve experienced is too large to count. But you know what? I love it! I want you to love rejections too.

In this post, I’d like to share some underdog success stories. Hopefully, they will motivate you to embrace suboptimal situations and keep on going.

The one constant theme from these stories is that when nobody expects you to amount to anything, you are free. And once you are free, you can soar!

When Nobody Expects You To Win

I bumped into the captain of our club’s 5.0 USTA team (top level) the other day and excitedly told him our 4.5 team had won the San Francisco city championship. We had gone 0-7 in 2021, the bottom of the league standings, and had a miraculous turnaround in 2022. I thought he would have been happy to hear the news.

Instead, without missing a beat, he responded, “Oh yeah? We just got done winning the 5.0 league.”

There were no congratulations from him at all, only oneupmanship. Sigh. But I still gave him props anyway. I liked his unsupportive response to our victory because it reminded me how difficult it is to be happy for someone sometimes.

For well over a decade, the 5.0 captain has prided himself on captaining winning teams. He also disapproved of the club starting a 4.5 team for years because he knew we weren’t very good.

The 5.0 captain is in his 60s, retired, and is very focused on league tennis. So to hear of us winning, where he was not captain, might have made him feel less than. It is strange because we all belong to the same club.

One of the best strategies to get ahead is to convince people you stink when you’re actually pretty good. By posturing yourself as inferior, you lower other people’s expectations of you. Once people think you’re not much of a threat, that’s when you can better navigate your way to victory!

This post is for those who:

• Want to get an edge in this hyper-competitive world
• Want to look on the bright side after being discredited, passed over, or slighted
• Are curious why you are perceived in a different way than you really are
• Feel a level of anxiety and dread before doing something challenging
• Enjoy competitive sports and the dynamics involved in team sports
• Want to reduce emotion from clouding making better decisions

As a kid, I loved watching martial arts movies. Drunken Master starring Jackie Chan was one of my favorites. So when I stumbled across a new old show called Kung Fu starring David Carradine, I was thrilled!

I was eight years old and attending Taipei American School at the time. Each summer, I’d go back to my paternal grandparent’s home in Honolulu. In the mornings before breakfast, my grandparents would let me watch TV. I’d usually just stick to watching the cartoons like Thundercats or GI Joe. But not this particular morning.

The first thing I thought when I watched Kung Fu was why was this show so slow and gloomy? The second thing I thought was why did the main character look so strange? He looked like a white guy trying to play an Asian guy’s role. Ah hah, he was a white guy playing an Asian monk! As a kid, the topics were also too advanced for me, so I quickly lost interest in the show.

It wasn’t until I was older did I learn about the controversy regarding Bruce Lee. Bruce Lee’s widow asserts that Bruce came up with the show’s concept and expected to be cast in the lead role. But Warner Brothers supposedly stole the idea and shut him out. The studio thought it was too risky to have a “non-American” be the lead.

Apparently, Kung Fu was a huge hit with American TV viewers in the 1970s. However, I just didn’t get it as a kid who grew up watching much more amazing martial arts shows in Taiwan and Malaysia.

When you’re young and naive, you tend to want to do things the right way. You’re taught by adults that cheating and lying are wrong. As you get older and wiser, you start to become aware of people gaming the system to get ahead.

What you also realize is those who game the system seem to end up staying ahead! Let me share some examples as well as one harmless example about myself.

Quitting is considered a dirty word. I’ve always had the view you should never give up if you want to achieve your goals. Even if you break both legs, you better drag yourself through the mud and rain to reach glory on the other side!

However, as I grow older, I’m slowly coming to accept the wisdom of quitting. Or at least quitting while you are ahead. Let me share a story from one friend who temporarily did just that.

I’ve been waiting to publish my 2022 goals until now because there’s some whacky statistic out there that says most people give up on their goals by January 15. Therefore, by waiting until after January 15, I have circumvented this sad reality!

2022 is finally the year to live it up. Less work, more fun!

After a difficult 2020 and 2021, I’m sure most of us are tired. But the good thing is, we didn’t let the pandemic go to waste. We worked hard, took risks, found new jobs, started new hobbies, and discovered what we really want to do. Having goals keeps us focused.

There really is no going back to the way things were. If you are still miserable at your job, in an unhealthy relationship, or dissatisfied with your overall lifestyle, it’s time to change. And change we will!

After sharing my 2021 year in review, here are my financial, work, and life goals for 2022. I’ll be turning 45 this summer, which means I am most likely in the last half of my life. Therefore, I will try not to waste too much time going forward.

I hope you will share some of your goals as well.

And just like that, another year is almost over. I don’t remember too much about what happened at the beginning of the year without scrolling through my photos. Most of your managers don’t either, which is why it’s good to keep a log you can reference in your year-end review, especially if you did something positive.

For this year in review 2021, I’d like to go over three main categories: investments, family, and writing.

Investments are what support my family. Family is what I care about the most. And writing is what I enjoy doing to help others. It gives me a sense of purpose.

When I started Financial Samurai in 2009, my main goal was to make sense of the Global Financial Crisis. That was a scary time period that created massive uncertainty for our careers and our investments. As things got better, I’ve tried to tackle interesting topics to enable us to live more meaningful lives.

Given the bull market has created so much wealth for investors since 2009, one of the challenges I’ve faced is maintaining the motivation to continue writing 3X a week. When things are going well, why not slack off a bit right?

The main reason why I didn’t write less this year is because I spent more time at home. If the pandemic was going to restrict some of my freedom, I would make the most of it by writing more. During uncertain times, I also want to be more helpful.

Further, I still enjoy writing and exploring new topics. There are an endless number of things to write about when you address real-life situations versus just writing articles to generate revenue. During the process, I often have these ah-ha moments that always feel satisfying.

Let’s go over the best of Financial Samurai 2021. These posts are either the most read, the most commented, or the most interesting in my opinion.