Making money is like playing a competitive sport. You train hard all your life for those moments on the battlefield where you win all the spoils or go home empty-handed. You console yourself after a loss for having tried your best, but eventually, you realize the game is rigged.
For the past 10 years, I’ve played USTA league tennis. It’s a great way to stay in shape, meet new folks, and keep the competitive juices firing. Everyone needs to balance mental activity with physical activity if they want to stay healthy.
For the past four years, minus one year off due to the birth of my son, I’ve played at the 5.0 level. It’s a treacherous level filled with ex-college players and even ex-pros. Few have a beer gut and everyone has at least one weapon, be it a cannon serve or a heavy topspin forehand.
Battling Against The Odds
I really enjoyed playing 5.0 level tennis my first year (2015). It felt like I had joined a new fraternity of men I never played with or against before. I joined a team of newly promoted 5.0s and high-level 4.5s and we relished just playing against high-level players, not concerning ourselves with victory.
During the second year, I no longer had as much fun because the experience wasn’t new anymore. In fact, the experience started getting old because I kept losing. It didn’t feel fair to match up with a 4.5 partner or a borderline 5.0 player like myself and battle against two veteran high level 5.0 opponents over and over again.
After following a 2-3 season with a dismal 1-7 season I thought surely the USTA would bump me down to 4.5, but it did not. The USTA said that because I lost some very close matches with a 4.5 partner against two veteran 5.0 players, those losses actually helped boost my rating.
During the 2018 season at 5.0, I realized there was no hope of ever getting ahead playing on a public park team unless I made some drastic changes. I was getting older, slower, and sustaining more injury.
Here are three reasons why I was looking into a black hole:
- If you are an elite player, you will be recruited by a private club. They will give you a discounted rate, sometimes wave the initiation fee, and certainly fast track your membership. The public teams from public parks will have no chance of ever recruiting you because they have nothing special to offer.
- Once the private club has some elite players, it becomes easier to recruit even more elite players to its team because similar-level players want to play with other similar-level players and create a social network. Meanwhile, public park players either don’t have the money or the connections to join a private club and are stuck playing with whoever joins that year.
- Private club players develop a familiarity with each other’s games because they tend to be long-term members. Having a strong chemistry is huge in doubles. Public park players are always rotating doubles partners because the team is open for anyone to join.
This year, I was excited to play against an opponent I had lost to 5-7, 6-7 in a two-hour match a couple of years earlier. He had played for UVA, a national collegiate powerhouse. His partner was an ex-Harvard player.
But this year, I partnered with a 54-year-old guy whom I never played with before. Like me, he didn’t play D1 college tennis. And my UVA opponent partnered with not a 5.0 rated player, but a 5.5 rated player who was once ranked 500 in the world!
Talk about a stacked game. We lost 3-6, 1-6.
From these three points, you can see how there is almost no way the middle class, let alone the poor can fairly compete on an even playing field. What is required to get ahead is a tremendous amount of luck and hard work. No surprise.
But besides luck and hard work, let’s look at some other strategies to help you compete against the rich in a rigged system.
How To Compete In A Rigged Game
1) Sandbag your abilities. Sandbagging in recreational sports is commonplace. People purposefully throw games so they don’t get bumped up. By playing at a level below your real ability, you can win more. It’s great to see how far your abilities can take you, but after reaching your peak potential, you may want to swallow your pride and move back down.
One of the keys to getting ahead at work is to consistently over-deliver on expectations. The way to consistently over-deliver is to realistically under-promise what you can deliver. You must act a little dumb to get ahead. This way, you’ll always be able to surprise on the upside.
The same phenomenon happens when a publicly traded company reports quarterly earnings. After 20 consecutive quarters of beating analyst estimates, analysts are either complete dumb asses, the company is just truly amazing, or the company has mastered the art of sandbagging. Sandbagging is important because stocks get crushed when they miss analyst estimate and tend to outperform when they beat.
2) Directly ask for help. One of the most insightful commentaries that have come out of an Asian Coalition suing Harvard for racial discrimination is what an Ivy league university admissions officer revealed. She said, and I paraphrase, “Out of all my years working at XYZ university, not once did I get an e-mail or a phone call from a special connection advocating for a potential Asian applicant. Whereas I was always fielding favors for other applicant races.”
In other words, stop believing that meritocracy alone gets you to the promised land! Swallow your pride and be bold enough to ask someone important who you’ve worked with for help and a favor. Self-advocate. Sell to others why you are worth fighting for. Don’t be so modest. If you don’t call in the favors, you are at a huge disadvantage to anybody who does.
Find a balance between offense (active self-promotion) and defense (letting your merit speak for itself). Take Financial Samurai for example. Oftentimes I believe my content is good enough to get recognized by larger outlets, so I don’t bother promoting my work. Yet, I’m frequently passed over. What a mistake to be so passive all these years. Instead, I need to pitch my work because I’m one of the few who actually has a financial background writing about personal finance.
3) Befriend the unicorns. While applying to a pre-school for my son, I learned that there were spots for only four non-sibling kids out of 300+ applicants. In other words, my boy has less than a 1% chance of getting in. We have zero expectations. But, we can improve our chances by going to fundraising events, befriending board members, trustees and so forth.
Seldom do people ask for help outside their circles. Make it a point to try and help that someone first before asking for anything. I found the best way to befriend rich and powerful people is by sharing a common interest. In my case, that interest is tennis.
4) Blaze your own trail. Sometimes the game is so stacked against you that you have no choice but to take all the risk by doing your own thing. I knew that my chances of getting promoted to Managing Director were slim working out of a satellite office. Hence, I decided to leave work and go straight to the top as the CEO of my own company. Succeed or fail, it would be all my doing.
If you are from humble beginnings, one of the greatest gifts you have is that you don’t have much to lose. Why do you think there are so many immigrant success stories in America? If you already come from a wealthy family, there’s too much downside to doing anything other than becoming a doctor, financier, lawyer, techie, or consultant working for someone else. Then again, once your family is super rich, you can really shoot for the moon.
5) Marry into wealth. You can either work hard for your money, or you can marry into wealth. I used to think this was an utterly BS strategy, but now that I’m older, I see the merits of finding companionship with someone who can provide all the comforts in the world. It can get very tiring being a sole income provider.
If you can’t afford to attend a rich private school for undergrad or your MBA, then the next best thing is to hang around in the same circles as the wealthy. Finding love is a numbers game. The more you can put yourself in a situation to meet a wealthy person, the higher your chance of finding a wealthy lifelong partner.
We know that wealthier people buy groceries at Wholefoods instead of at Safeway. Wealthier people tend to shop at Nieman Marcus than at JC Penny’s. They go to the opera, the ballet, and to galas. They tend to play golf. Here in San Francisco, you might want to just hang around at one of the many Facebook, Google, and Apple shuttle stops to start up a random conversation about how to generate more fake news revenue.
It feels amazing building your own wealth. But all the people I know who married into wealth don’t seem to mind flying private one bit.
Recognize All That’s Unfair In This World And Proceed
Do I wish I was 6’6″ with a 145 mph serve? Only when I’m playing tennis. Otherwise, sitting in a car or on a long flight would be a PITA. I’m happy with my 5’10” frame, but recognize in order to compete effectively, I’ve got to train harder and eat better than someone with more physical advantages.
As the world gets richer, you will encounter more scenarios where your peers have had everything given to them. It’s not their fault. Parents can’t help but want the world for their kids. You can either get extremely jealous about their good fortune, or you can learn to accept reality, befriend them, and see if you can create some magic together.
Work on your merits, but don’t be embarrassed to ask for help from those who can.
Readers, what are some of the ways that you’re working on to catch up, match, or surpass the rich? Does it bother you that the game seems so rigged? If you’re wondering about my tennis, I’m hoping to get bumped down to 4.5 for next season. I have too much pride to join my club’s 5.0 team and partner with ringers. Winning is fun, but it’s 10X more satisfying to win as an underdog.