How To Convince People You’re Bad When You’re Actually Pretty Good


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 they are perceived in a different way than they 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

The Thrill Of Competition

When I’m not writing, one of my favorite activities is playing USTA league tennis. It’s fun to feel the excitement and stress before each match. An official league match forces you to eat better, stay in better shape, and practice. I love it!

After coaching a high school tennis team to two Northern Conference Sectional titles, I’ve become hooked on devising strategic lineups. It’s also fun to mentor young adults.

Finding joy in coaching is a natural progression from practitioner to teacher. But as I ain’t too old yet, I continue to play competitive tennis as well.

Time For Some Good Old Fashion Disrespect!

Recently, I received some disrespect from a teammate who wanted to change our winning doubles pairings. We’ll call him Kaka.

Not only did Kaka want to partner with my partner Jack, but he also suggested he play at #1 doubles with Jack as well.

His request seemed to defy logic as Jack and I had gone 4-0 as partners and also won a crucial playoff match which enabled our team to reach the city finals, Furthermore, Kaka had not played in the playoff match (was on vacation). 

Now he wanted to break us up and take my place!

I was miffed. It’s generally not a good idea to split your kings when the dealer is showing an eight on the blackjack table. So as any good Financial Samurai would do, I tried to understand why Kaka didn’t think I deserved to continue playing with Jack despite our undefeated record.

A Winning Record

Financial Samurai USTA tennis league record in 4.5 in 2022

Not only am I 4-0 with my partner, I’m also 11-2 (84.6% win percentage) this season after playing for two 4.5 18+ age teams in different leagues. I’m also 19-4 overall for the year if I include my 8-3 record in the 4.5 40+ age league, where we won the city championship earlier this year.

Further, I played four years at the 5.0 level before successfully self-rating down to 4.5 in 2022. Whereas Kaka went 8-6 (57% win percentage), has never been rated 5.0, and has never won a 5.0 match. Kaka is a good player, just not as good as he thinks.

The answer to the disrespect is I had somehow convinced Kaka I’m not a very good tennis player even though my winning record is there for all to see. And to be fair, my partner Jack is also a good player with a great serve. However, Jack has also never been rated a 5.0 and went 0-5 with different partners when he last played 4.5 in 2016.

When you play team tennis, to win you must think in derivatives. It’s like coming up with the Financial Samurai Wealth Reality Ratio to determine the most financially satisfied and dissatisfied cities in America. Don’t just take the data as given. Analyze it to find new answers and solutions.

Winners figure out which teammates match up best and what happens to the strength of other doubles pairings when you make certain combinations. Competitors also need to have a strategic lineup because a team needs to win three out of the five lines to win the entire match.

How To Convince People You’re Bad Even Though You’re Good

Being able to convince others you are no good even though you have a long track record of success is a skill. Whether playing a competitive sport, building a business, or trying to get promoted at work, the less people think of you, ironically, sometimes the greater your chance of getting ahead.

Using my tennis example, let’s review how a player with an inferior record convinced himself he was superior. I’ll also discuss what I did to make him believe this to be true. This is sort of like judo Financial Samurai magic!

And to clarify, this is a post-mortem analysis, not a pre-mortem analysis. I’m writing this article after getting disrespected, not before to try and scheme. I’m just trying to see the optimistic side of things given we will all be looked down upon or passed over at some point. How do we turn this disrespect or slight into something positive? Kaka and I are just fine.

1) Be a great teammate.

One of the best ways to give people confidence is to be supportive after a loss. If you’re battling players at a similar level, over 50% of winning in tennis is mental. Therefore, trying to keep your teammates feeling positive is important.

If you don’t believe you are able to win, then you have already lost. Even if you believe there’s only a 30% chance you will prevail, you must still envision your low probability of victory coming true. Don’t create a second opponent by not believing in yourself!

After each match Kaka lost, I told him it was just bad luck or their opponents were a top-tier team. I had told him he did great to keep his spirits high so he could keep battling at a high level in future matches. Because at the end of the day, we are both on the same team so I try to be as supportive as possible.

The better you are as a teammate, the less you will be viewed as a threat.

2) Make them believe they are the best.

Team tennis consists of three doubles and two singles lines. The first to win three lines wins. Each line counts as one point. Therefore, if you’re playing doubles, it doesn’t matter if you put your best team at 1, 2, 3 since all matches count the same. The same thing goes for singles.

The goal is to mix around your lineup throughout the season to keep your opponents guessing. After all, each opponent will study the historical lineups posted on the web before deciding on their lineup. The ultimate goal is to present a lineup that will create matchup advantages.

Even though each line counts as one point, we tended to put Kaka at doubles 1 or 2 because that’s where he wanted to be. He believed our opponents would always put their best doubles teams at 1 or 2 and he wanted to play the best. This is a great attitude to have. But the best doubles teams don’t always play at D1, as was the case during our playoff match.

At D2, my partner and I beat the best doubles team 6-4, 6-3. Our opponents had played together for several years and had a 0.750 win percentage before losing to us. Conversely, at D1, our opponents had a 0.400 win percentage and one of the players was a 4.0 in 2019. My partner and I would have handily beaten them 6-3, 6-3.

By consistently putting Kaka at D1 or D2 doubles, we made him believe he was the best doubles player. By telling someone they are the best enough times, they might actually believe it. And by default, they will think you aren’t as good even if your record says otherwise.

USTA Rating Distribution
USTA Rating Distribution. 1% are rated 5.0

3) Don’t play your hardest when your opponent is around.

When we practice, I don’t go 100% because I don’t want to get injured. I’ve been struggling with pain in my elbow all season, which gets exacerbated after each match. Instead, I try to work on strategy, new shots, and placement.

The worst thing that could happen is going all out in practice, injuring yourself, and not being able to play during a real match. As a result, Kaka just sees me go at ~70% most of the time. Therefore, he thinks I’m slower, weaker, and less skilled than I am.

First and foremost, I play tennis for fun. So I’m constantly joking around and sometimes smack talking. Whereas Kaka is usually playing at 100% and is quite serious. Maybe at age 26, that’s the way things are. You’re more serious because you have more to prove. But at age 45, I’m satisfied with my record. I mainly just don’t want to hurt myself!

In sports, we call this act of not playing as hard, sandbagging. I’ve seen it done with incredible success when warming up against opponents before official matches. During warmups, you think your opponents aren’t so good because they aren’t hitting any balls back or have really weird shots. But as soon as the match begins, they step up their levels.

Work your hardest when nobody is looking. Sandbag when your opponents are observing. If you do, you may successfully be able to lower their guard. Then one day, you may surprise your opponents who never saw you coming.

4) Always be smiling.

The easiest way to disarm someone is with a smile. It is practically impossible not to smile back at someone who is smiling at you. The more genuine your smile, where crinkles on the side of your eyes form, the better.

The goal of the smile is to appear less intimidating. The less intimidating you appear, the less of a threat you will appear to your opponent.

Before each battle, try being super nice to your opponent. Ask them about their kids, praise them for their record, or compliment them on their outfit. The better you make your opponents feel, the less they will want to beat you up. They might even give you the benefit of the doubt with some close line calls!

When I’m on the tennis court, I’m always in a great mood. Maybe I have a little too much fun, which can annoy an opponent. But I can’t help but have a smile while playing just like how it’s impossible not to smile while jet skiing.

Smiley people are not taken as seriously in competition.

5) Publicly praise others, but never praise yourself.

The final strategy for convincing people you aren’t as good as your record is to praise others and never praise yourself. Even if you’ve got a strong record and believe you are crucial to the team’s success, always publicly praise your teammates, bosses, and colleagues.

In the league playoffs, Jack and I were able to win quickly our doubles match. Therefore, we had time to go over and root for our other teammates, all of whom were engaged in tight battles. Ultimately, our team prevailed 3-2 to win its first-ever playoffs match in history at 4.5 18+.

During our post-win celebration, I commended our winning singles player for his steady groundstrokes. I praised the second winning doubles team for holding onto the lead after being up 5-1 and finally finishing the second set 7-5. And finally, I praised my partner, Jack, for his great net play.

By praising everybody else, you take the spotlight off yourself. And when you don’t have the spotlight shining on you, you might actually compete better given people will have lower expectations of you.

Most recreational tennis players don’t play USTA league tennis because it is simply too stressful. With so much tension, it’s common to play below your potential. But if you can enter a flow state because you’re feeling loose, you tend to play much better.

I like the stress and the adrenaline rush of battle. But this attitude took time to harness. Be like water my friends!

The Importance Of Deflecting Attention

If you can work in privacy, you can focus better on the things that matter. You won’t constantly be pulled in different directions by people whose opinions might not matter. This ability to better focus is one of the key reasons why some private companies shun going public, or at least stay private for longer.

One of the things that worries me most about marketing my new book is, ironically, the attention it may receive. Yes, I want my book to be read by as many people as possible because I’m certain it will help improve people’s financial lives. To do so successfully, however, means being out there, getting on podcasts and doing video interviews. These endeavors will start appearing the week of July 18.

Yes, I want to have more Asian American representation in the rather homogenous personal finance and nonfiction finance author space. Goodness knows more love is needed. At the same time, I don’t want so much attention that I end up losing my freedom.

I’ve always believed the beauty of writing is that it doesn’t matter what you look like. Instead, it’s the content that matters the most. But I also understand the realities of the world.

Embracing The Failure

After writing this post, I realized I’ve grown accustom to deflecting attention in multiple activities because I don’t like the spotlight.

Receiving attention is a distraction. It takes away from the actual doing, such as the tennis playing, or the actual product, such as the book. I’d rather have my record or my results do the talking for me.

However, if I’m being completely honest, I’m also afraid of failure. After all, if nobody expects anything out of me, can I really fail?

Perpetual failure gets old after a while. At some point, you might fail so often that you will never want to try again. As a result, it’s often easier to try and fail without anybody looking than to fail spectacularly in front of a crowd!

But so far, I continue to try because the regret of not trying feels worse than the pain of failure. I am currently way outside my comfort zone doing video and TV interviews, which probably means it’s something worth trying.

Let’s hope my 15 minutes of fame doesn’t last longer than a couple of weeks.

Finishing A Miraculous Season

Before the 18+ tennis season started, I was going to play with a different 4.5 team because I knew many of its players. It had a strong roster and was favored to win it all. I also had played on its 9.5 combo team (5.0 + 4.5) last year as a 5.0.

On the other hand, 2022 was going to be only the second year my club would field a 4.5 18+ team. In 2021, my club’s 4.5 18+ team had gone 0-7, a league-worst record. But in the end, I decided to join my club’s team because it was the right thing to do.

Not only did we win our first ever 4.5 18+ match in the club’s history, we also won our first 4.5 18+ playoff match. We were fired up and ready to play for the city championship!

However, two days before the finals, the opposing team’s captain canceled to save $300 on court fees. Why? The San Francisco league got a wild card, which meant the top two teams automatically advanced to sectionals! Therefore, the captain wanted to save money. Bummer how the host didn’t want to battle!

The opponent was the team I had originally planned to join at the beginning of the season. It finished the regular season 9-0 and had beaten its first-round playoff opponent 4-1.

The Glory Of Being The Underdog

Joining the league’s worst team at the beginning of the season and co-winning the championship feels surreal. So does our opponents not wanting to face us partially out of fear of losing.

It reminds me of the feeling I got after getting a job at Goldman Sachs in 1999 after graduating from a non-target, public university. After going through seven months, six rounds, and fifty-five interviews, I was finally given a job offer along with only a handful of Ivy Leaguers.

With Buy This, Not That, I’m once again the underdog in trying to make the book a national bestseller. I don’t write for a major media publication with a massive platform. I’m not a public persona with a huge social media following. Nor am I part of the majority or the popular crowd who have their favorites. But I’m still going to try because there is no downside in trying!

Although going the harder route will often be more treacherous, if you surpass expectations, the glory is all the greater. Do hard things. Embrace someone’s poor perception of you. You might surprise yourself!

Readers, any other strategies for convincing people you stink even though your track record shows otherwise? Do you prefer battling as the underdog or as the favorite? Do people see you as inferior as well? If so, how do you react?



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