Embrace The Underdog Within To Win: Who You Are Is Good Enough

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.

Homegrown Winners Without Ringers

After sharing the cold encounter with my 4.5 team captain, he pointed out something amazing.

Our 4.5 team had won without the benefit of any ringer recruits! We were homegrown except for one outside member who I had invited to join because we frequently didn't have enough players. He was in his mid-40s and had a sub-0.500 record in his other league.

Our 5.0 team, on the other hand, is made up predominantly of ringers recruited by the captain. In exchange for playing a certain number of years on our club's 5.0 team, they get a steeply discounted rate to join the club. Further, their monthly dues are also discounted.

Over the years, this method of recruiting and providing subsidies has been the cause of debate by many members who pay full freight. Having a great 5.0 team helps bring glory to the club during sectional and national tournaments. But having recruits who take up court space and don't bother interacting with other members isn't ideal.

When my 4.5 team captain told me winning with ringer recruits isn't as impressive as winning with what we had, I agreed! It's like getting into a top university without your parents being alumni. It's also like the Warriors winning the NBA championship with a core group of draft picks instead of assembling a super team in free agency. So satisfying.

How Did We Win As Underdogs?

So how did we go from 0-7 last year to winning it all? Here are the reasons why.

1) Created buy-in from others. We had some good 4.5-level players who weren't willing to join because they didn't want to play for a losing team. Once I joined this year, I convinced a couple of other people to join, who then convinced a couple more people to join.

2) We took each match seriously. I'm sure during a couple of matches, our opponents didn't bring their best players because they thought they'd wipe the floor with us. After all, we had lost our first four matches 0-5, 2-3, 1-4, and 1-4. But we kept experimenting until we finally won our first match in our club's 4.5 league history 4-1. After we got the first win under our belt, we started believing.

3) We studied matches and took risks. For example, instead of playing our regular singles guy in singles during the playoffs, we put him in doubles. He ended up winning his doubles match in a nail biter. The doubles win proved crucial given we won the playoffs 3-2.

4) We showed up. While one other club always had to default one or two lines, we filled five lines every single match. Even if we had to call up 4.0 players, we always gave ourselves a fighting chance.

5) Lots of luck. By showing up to every match, our luck improved. However, a lot of 3-2 wins were coin flips. And we just got lucky.

Embrace Your Constraints

We understand the tactic of convincing someone you are not as good as you really are to get ahead. Once you lower someone's guard, you can more easily surprise on the upside.

But what if you simply have disadvantages? Let's say you have a visual disability or you look different from the masses. Embrace it! Accept your underdog status for what it is. If you are the underdog, nobody expects you to win. But if you do, you will gain way more satisfaction than the person who has all the advantages.

As fellow Portfolio Penguin author, and HBS professor, Laura Huang wrote in her book, Edge, “When we own constraints, magical things happen.”

Laura told a story about how she got her first F in college for a mandatory writing course assignment. The professor said, “Don't worry, since English is not your native language, it will take you some time to get the hang of writing. It will come.”

The thing is, Laura, was fluent in English.

She bumped into another Asian student in the class who also got a poor grade, but was fluent in English too. They decided to own their constraint by referencing their “non-native English” as often as possible.

In the next assignment, Laura talked about how she had to overcome her language challenges. She saw the writing course as her salvation! In the end, the professor detected none of her sarcasm and gave her a B-.

Laura's example reminded me of one time in high school in Virginia. To get out of having to answer a question I was unprepared for, I just responded, “Sorry. No speaka Engrish.” And the lecturer left me alone so I could goof off! Yes!

Believe You Are The Underdog Whether You Are Or Not

Ever since I was a kid, I've been the underdog. I'm not particularly good-looking, smart, strong, or charming. I'm average at best. But life still turned out fine by being more strategic and adopting an indomitable attitude.

Even though you might be an average or below-average person competing against folks with tremendous advantages, you can still thrive in this ultra-competitive world. You must believe you deserve to compete just like anybody else! And when it comes to building wealth, you must adopt an abundance mindset.

There are literally trillions of dollars out there for the taking. For example, there are CEOs who have received $20+ million severance packages after lying on their resumes and running their businesses into the ground. Don't ever think you don't deserve to be wealthy, because you do!

Unless you are an egomaniac who just can't get enough attention, it's nice to be the underdog. You can walk around freely and nobody will ever notice you. As the underdog, you can more freely experiment with different strategies and have less fear of failure.

Let's go through some other scenarios and discuss why it's great to be the underdog.

Underdog On The Job

As the underdog, your bosses and colleagues will tend to fight for you to get paid and promoted. The key is to always stay humble, always be helpful, and always be pleasant to work with.

When you first start a new job, you are often at the bottom of the rung. While there is a tendency to show how knowledgeable and great you are, it's usually better to observe and learn as much as possible from your peers.

Coming across as a know-it-all with little experience is a career-limiting move. Even if you are a lateral hire with years of experience, stay low-key. It doesn't matter if you do know all the answers. Keep your special opinions to yourself until you have the complete trust of your colleagues.

Do not try to outshine your senior colleagues. Instead, use your knowledge to help them succeed.

Underdog With Money

If you come from a poor background, percentage-wise, you probably have more financial upside than someone who comes from a rich background. With little money, there’s not much left to lose. As a result, the money underdog may have more freedom to go for glory.

Now compare yourself with a person who went to business school for two years and paid $200,000 for their education. Sure, they may be wealthier than the poorer person, but many MBA graduates are forced to take secure jobs to get a positive return on their education. Some are too risk-averse to start a business or pursue more enjoyable but lower-paying jobs.

If you are making a substantial amount of money (more than 50% of the median income), or at least more than your friends or colleagues, don't ever tell them how much you make. Many relationships have been lost over the knowledge of another's income. Only when your friend or colleague starts making the same amount as you or more will they no longer feel uncomfortable around you.

Practice stealth wealth if you want to be liked or don't want to be bothered as much.

Underdog With Your Looks And Personality

If you are not particularly attractive or witty, you will naturally motivate yourself to work out, learn how to dress and groom, and take communications classes. Over the long run, you may end up being a better person than the attractive person who never bothers to work on their emotional intelligence.

You may also have a happier and more stable life. The attractive person, on the other hand, may go through more break-ups after their partners realize there’s nothing pretty below the surface.

Attractive people tend not to work on their personalities because they don't need to. Society overlooks their flaws more easily. But as we all know, looks fade over time.

Underdog With Your Online Business

Let's say you are a new blogger with no readership. Rejoice! You are free to write whatever you want without fear of persecution. Nobody cancels a nobody! Instead, the mob tends to go after those who are threats to their existence.

As a new business owner, you have carte blanche to experiment with various features and products without fear. Once you build momentum, you can better adjust to your clientele's needs.

On the other hand, let's say you run a popular blog with over 100,000 pageviews a month. You will likely be inundated with e-mails and requests from people you don't know who want you to pitch their product. You will also likely be stalked by people who don't like you, but still read everything you write.

Every time I publish a new post on Financial Samurai, the content is “scraped” by at least three other websites. They take my content and republish it on their own website verbatim without permission. Moreover, every time I publish a new idea or a popular post, there will soon be similar types of posts by other bloggers.

The online world is ultra-competitive. It is very hard to come up with helpful new concepts like FS-DAIR, The Wealth Reality Ratio, BURL, and more. As a result, it is much easier to copy someone else's work and spin it as your own. Oh well.

Intelligence Underdog

If you are naturally witty, received straight A's in school, and got a perfect SAT score, you are an anomaly. Given you are a rare breed, you will probably be more frustrated than average when people are slow to pick up things.

If you aren't careful, your intelligence will rub the average person the wrong way. In some cases, people may start thinking you're arrogant, whereas, in reality, you can't help yourself.

Conversely, let’s say you come across as having below-average intelligence. That’s OK because intelligence can be cultivated through deep work. After skimming the surface of various subjects with podcasts and news articles, you can go deeper by reading books and taking extra courses.

Authors are subject matter experts who spend a couple of years writing down their expertise for your benefit. The more good books you read, the smarter you will become. Pity the intelligent person who thinks they know everything.

Underdog Book Author

If you don't work at a major media publication, aren't famous, or don't have a large social media following, you are an underdog when it comes to getting a literary agent, let alone getting a book deal. You can also forget about ever getting your book on a bestseller list. The system will block you every step of the way!

Not only do I have none of these things, but I also haven't networked consistently with other bloggers and podcasters in the personal finance community over the past 10 years. I've been focused on being a dad since our son was born in 2017 and spending time with friends in the offline world. Therefore, my book, Buy This, Not That, won't have much support from the personal finance community.

Accepting my underdog status as an author forced me to add more value to my writing. I went beyond making people feel good with fluff by also providing concrete action steps. Then I included storytelling with my analysis to make the chapters more relatable.

As a result, I had to find new ways to market BTNT since I got so many rejections or non-responses. Therefore, I reached out to people outside of the personal finance niche. I touched base with a 4X NBA champion, a CEO of a public company, and a popular lifestyle persona to get some support. It was uncomfortable to ask for support, but to my surprise, some said yes.

Although my book had a snowball's chance in hell to make a bestseller list, Buy This, Not That was able to make The Wall Street Journal Bestseller list! Not bad for a stay-at-home dad who isn't a public figure.

Buy This, Not That Wall Street Journal bestseller July 2022

Thanks to all of you for picking up a hardcopy and spreading the word to your friends. Getting on the WSJ hardcover business bestseller list is almost mission impossible. It is filled with established players as you can see with my book being the only new entrant. It's cool to finally see some diversity on the list too.

Fight the status quo and never surrender!

Don't Let The Overdog Within Get Out

After being the underdog for so long, you may eventually turn into an overdog. If so, people will start gunning for you. Accept your position of strength, but never forget your humble beginnings!

The next time you feel like bragging about your great accomplishments think twice. Take a hammer and bash your ego back in place. Always balance your successes with your failures. As soon as you forget where you came from, you will start to lose your advantage.

The world is only getting more competitive by the day. There will always be someone better than you, richer than you, and smarter than you. Rejoice! Use your underdog status as motivation to keep going. I always do.

Related posts and action items:

For A Better Life, Be The One Percent In Something, Anything

Sweet Dreams Of Becoming A Millionaire Again

When People Doubt You, Just Keep On Winning

Spoiled Or Clueless? Try Working A Minimum Wage Service Job

Readers, would you rather be the underdog or the overdog? What are some other examples of an underdog overcoming long odds to win? How else can you utilize your underdog status to compete?

For more nuanced personal finance content, join 50,000+ 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. To get my posts in your inbox as soon as they are published, sign up here

24 thoughts on “Embrace The Underdog Within To Win: Who You Are Is Good Enough”

  1. This article made me feel better about being an underdog. I started a cleaning business it’s an LLC and my schedule is packed, I been wanting to grow it and feel I should have employees and grow big but my fear is holding me back. I also started a blog on dogs , pitbulldogmom , and it is fairly new, I am totally an underdog in this world. But my thought is to just produce content and over the years I’ll get better, it’s deff not a get rich quick thing so it’s ok to be the underdog in it. But I think I might also be in the wrong subject because I’m losing my enjoyment writing on the subject matter. Anyway great blog and article thank you!

  2. Ms. Conviviality

    Congrats on making it onto the WSJ bestsellers list! That’s such a great accomplishment! The best part is that this exposure will allow your your book to help improve so many more lives.

  3. Nice job winning the city championship and getting on the Wall Street Journal bestseller list!

    I think the statistic is like 86% of bookwriters are white, and over 99% of those who make the best seller list are also white. So you beat the odds!

    I’m listening to another another author promote his book and he’s got huge backings from all the other white podcasters and writers. This is even though he doesn’t have a Finance background and has a very thin book.

    You being able to fight the status quo is very inspiring. I’m not sure whether your readers truly recognize how hard it is to break through.

    Well done.

  4. It can be different for some, but with most well-known businesses (to include most self-made billionaires), underdogs that become successful are promptly relabeled as villains by a large and very vocal crowd.

    Relative anonymity is a good thing. While most successful people do not pay for their success with fame, a lot of successful celebrities find they have accepted fame as the cost of their success, rather than as something desirable on its own. Of course, the worst thing of all is to be famous without being successful. Those are the tragic folks that have paid the price of losing their relative anonymity, and were not compensated for it. A lot of child actors fall into this category but they are not the only ones.

  5. Sam— incredibly proud and thankful for your success.

    When an individual makes an intention to be great and give your best—- it is a lot of work! Ones trajectory can only evolve with perseverance and discipline.

    When I took philosophy of religion and studied great philosophers lens in the parables within the Bible I was enlightened. Why? Because it was all about living in accordance to your own mode of being! If all souls were aware of their heavenly gifts, inner worth and infinite love this world would sparkle!

    Thanks for being God’s finest bright light!

    Shine on—


  6. Congrats on making the WSJ Bestsellers list! What an amazing accomplishment to be on that list with some familiar names. I believe you’ll be on your way to #1!

    Almost done reading the book. I’ve read other personal finance books before but yours goes into each topic on a deeper level. While other books I’ve read only scratched the surfaces.

    1. Thank you. I think this is about as good as it’s going to get, unless the book takes on a life of its own as readers like you consistently share through word of mouth.

      I’m satisfied with whatever happens in the future because iI tried my best. As a SAHD dad and non-professional writer, I’ll take it!

      As for the content of the book, I definitely wanted to go deeper to help readers make more optimal financial choices. This books are fine quick reads that make people feel good. It is a great formula. But I wanted to do something different.

  7. Almond Butter

    Congrats! You are the best. I LOVE these types of posts. I’ve been an underdog my entire life. Thanks for sharing your experiences as an Asian male in the US. I’m always humbled by it and grateful for the share; I learn so much. I think in the US, other minorities think Asians have it pretty good statistically speaking ( Education/wealth). Though like all things in life, it’s isn’t so black and white; life is both opaque and gray. No one wants to be ignored and undervalued; no one wants to be bullied, irrespective of wealth or education status. I’ve learned so much from you sharing your experiences. I’m grateful and motivated to continue grinding, despite my late start. No retreat! No surrender! I accept No Defeat! Keep kicking butt, Samurai!!! Your troops are watching you lead the way!

    1. You’re welcome and thank you! It’s been fun sharing experiences. I’m always interested in hearing about other experiences as well. It’s pretty fun seeing how two different people can experience two different things at the same time.

      Everybody goes through struggles. It’s how we view the problem and come up with a solution that matters the most. As a Financial Samurai, we know there is always a solution! Just got to find it.

  8. Hi Sam!

    Huge congrats on the success of your book!! You’re right up there with Atomic Habits and Brene Brown! That’s amazing!!

    I will be buying it once I get through a few more books on my desk. :)

    I still enjoy your newsletter. I love your content!


    1. Thanks Karla. I didn’t know who Brene Brown was before this journey. I’ll have to check out her book. It’s fun to compete against professional book writers as a non-professional writer.

      Now that I have completed, the Curiosity is gone. I’m not sure whether I want to write another book for 10 more years. That was the cadence between my first book about severance negotiation in 2012.

  9. It is hard to be happy for someone if you yourself are struggling. And that’s kind of the sad part of the world.

    It’s become so competitive that only a few self-assured people can be happy for another person’s success.

    Congrats on making the list and winning the city championship! I wouldn’t feel good winning with a team of ringers either!

    1. Yes it is. The good thing though, is that once you find out who cannot be happy for you, then you’re able to subtract them from your life and better focus on who can be happy for you.

  10. Congratulations on your accomplishment, Sam! WSJ business bestseller list! I agree with the other poster – none of your long-term readers are surprised with your achievement.

    I love the underdog mentality – it keeps you hungry. I am sure that your children will develop this attitude as well.

    With rejection, don’t get bitter, get better!


    1. Thanks J&A! That is a great saying. I’m not sure if I have ever heard that before, even though that is definitely a philosophy I have embraced for a while. It’s hard not to feel the sting of rejection. But it is a sting that wakes your senses up and forces you to be more strategic and try harder.

  11. I love the underdog mentality! And congratulations for making the WSJ bestseller list! No easy feat.

    I always like to have a chip on my shoulder to stay motivated. Because as you get older and wealthier, it’s easy to lose motivation. I just have to be careful not to get D. motivated by comparing up too much. Otherwise, it’ll backfire.

    Underdogs unite!

  12. Very motivating post! I’ve been the underdog countless times. My challenge in my younger years was actually feeling worthy enough to actually try to come out a winner. Now that I’m older I’m comfortable with who I am and embrace my weaknesses and shortcomings. What I need to do is think about how to be more strategic and find ways to use being an underdog to my tactical advantage.

    And btw – a HUGE congrats on making the WSJ bestseller list with your new book. That’s incredible!!! And shows what all us long-time fans know – that you truly are a stellar writer who really knows his stuff! Props!

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