When Is It Time To Give Up And Admit Defeat?

Tennis Battle Serve

I played 6 sets of singles the other day.  That’s right, 6 consecutive sets over the course of 4.5 hours.  Not doubles.  Singles where you’re running around like a maniac.  With even the major tennis opens going at most 5 sets, what gives you ask?  Well, one of the most exhausting and ridiculous things happened, which I’d like to share with all of you.

About a month ago, the captain of a new tennis league team I joined came over to my club as my guest.  We warmed up for a bit and decided to play a match so he could get an idea of my skill level, despite both of us being rated the same.  I beat him 6-0, 6-4, 6-1 in a best of 3 set match, with the third set played just for fun.  After we shook hands, he immediately ran off excuses as to why he lost: Surgery on shoulder, weak knee, crooked toe, etc.  No problem, as I have some ailments too, like a torn meniscus (!), but keep them to myself.

He said he wanted to avenge his loss, and I said I would be glad to give him a rematch.  Allowing an opponent to redeem themselves is always the honorable thing to do.  My mantra in sports and in much of everything else is to always be the underdog.  In sports, it’s particularly important that your opponent underestimates your abilities.  The element of surprise is very important, as such, you want to keep your skills guarded until the time is necessary to unleash.


Fast forward to now and the rematch is on.  During warm up, he kept talking about how he was going to beat me, to which I kept on saying with a smile, “I doubt it, but you can try.”  At the end of the warm-up, he kept on egging me on, so I said, “How about we bet a friendly $25 bucks then?”  $25 is enough to pay for the guest fee and get a couple brews afterward.

He responded, “Only $25 bucks?  Let’s put some real money and make it $50!?

I asked him, “Are you sure?  Because that’s a lot of money, and I don’t want to have bad feelings between us if you lose.

He scoffed and said, “Ha, no worries Sam!  I will not lose.  Bring it on!

In about 1 hour and 10 minutes, I took him down 6-0, 6-3 in the first match.  You would think that he would just wave the white flag and fork over the $50 bucks right?  Wrong!  He said I got lucky, and that he wanted an immediate rematch immediately!

Double or nothing?” he asked indignantly.

You’re on!” I responded back, somewhat miffed.


The second match lasted about 1.5 hours and was closer than the first.  During this match, he literally tripped on his feet twice due to exhaustion and tumbled onto the cement.  I thought he was done for sure, since he was sweating bullets and gimpy.  We had already played 2 hours and 30 minutes, which is already about 1 hour longer than we normally play.

Despite what I noticed was obvious injury and exhaustion during the match, we both kept battling like warriors.  After all, we had $100 on the line!  Alas, the results were the same and I took him down 6-3, 6-3.


While on the bench, he starts talking again! “Sam, I know I’m going to beat you.  You are so lucky, and I am so unlucky!  How many games was I up 40-15 and I ended up losing?

Hmmm, maybe one? I thought to myself.  I was sitting on the bench, exhausted and drinking my orange Gatorade with pleasure.  I couldn’t wait to hit the showers and collect the $100.  I was fantasizing about sitting in the steam room and getting a massage afterward.  Phew, no injuries yet, just a lot of sore muscles.

During mid-fantasy, the captain blurts out,  “Let’s play again!  Double or nothing for $200!

At this point, my quads feel a little like spaghetti.  The problem is, I knew I could beat him, and he wouldn’t stop talking.  Nor would he give me any respect for me beating him!  He kept making excuses how something was wrong with him today, not that I was playing well.

Despite feeling weak, I told him he was on, but asked him multiple times again whether he was sure he wanted to battle, and whether he was sure he was going to pay me if he loses!  He nodded, and said “Of course.”

It’s 4-all in the first set, as we both held serve.  This was the do or die point of the third match as I could already feel the cramping in my right calf begin to form.  Gathering all my energy and focus, I break his serve and hold my own to win 6-4.  Yes! I think to myself.

One hour thirty minutes later from the beginning of the match, I take him down 6-4, 6-0 for a total six set score of 6-0, 6-3, 6-3, 6-3, 6-4, 6-0.  The 4.5 hours was the longest amount of time I’ve played tennis since high school.  At the end, he finally gave me props and said that I have an excellent ability to adapt to different game styles.  A little back-handed, but I’ll take it as a compliment.


We went to the ATM machine where he proceeded to give me ten, $20 bills.  Oh how nice they looked in my calloused hands.  I bought him some chicken teriyaki dinner and a drink and talked strategy for our upcoming match.  My captain was thinking about challenging me to a rematch for $200, but he pulled back.

Instead he offered, “How about the loser pays for guest fee, balls, and a smoothie next time!”  Now that’s more like it!

Readers, have you ever approached something so stubbornly that despite being outmatched, you refused to quit and got yourself in deep doo doo?  What makes people so stubborn?  Is it pride?  Is it delusion?  Are you defiant like me?  I felt there was a real risk of injury if I accepted the 3rd match in a row.  But, given the stubborn and defiant person that I am, I thought the $200 was worth the risk.  



Photo: Tennis Battle, SD.

Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

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  1. says

    One of my weaknesses is never quitting. There are many times, I should give up and apply my efforts elsewhere, but I don’t. I am getting better though, I went from never to something shorter. Despite this weakness, I think I would have assess the situation better than the captain. He was blinded by his own ego.

    • says

      I have the same weakness… never, ever quitting until the very end. It’s the attitude that was instilled in us in football, basketball, baseball, and tennis growing up. Fight til the end… which sometimes, is bad when the party is over, and we don’t realize it.

      If I was playing a better player, I would probably challenge him to a rematch, but just ask for a handicap. B/c if I lost 0-6, 3-6, it is clear to me my opponent is much better.

  2. says

    Wow that guy sounds like a maniac with a strong stubborn streak. That’s awesome you beat him all three matches! I admire both of you for being able to play that long as that is not easy! Since you guys have strong endurance your team should be in great shape for the season! I like how you bought him dinner at the end. Great sportsmanship Sam!

    • says

      Very stubborn.. and in the end, he STILL said he can and will beat me. I’m sure he will eventually, but he does not quit, so that’s good. I will stay out there until the DEATH if I have too!

  3. Tennis Fan says

    Nice job taking his money! I would have given up after losing 6-0, 6-3 after the first rematch, as that is an ass kicking. However, I see how he would stubbornly want to try again. Nice of you to allow for such a thing.

    Get some rest!

  4. says

    After 6 sets, I’m surprised you could even walk to get dinner! Great on your part to still show good sportsmanship after such a display of sore losing, big ego, and something bordering on delusion. Leadership (i.e. his “captain” title) should be as much about humility as it is about pure skill. It sounds to me like he was trying too hard to protect the title and not enough to let you shine.

    Losing is a tough pill to swallow, no doubt, especially when you lay so much ego on the line. I don’t let my money goals define who I am, and as hard as I try to reach them, sometimes it’s just time to let go and move on to something else.

    • says

      Well, thankfully the first set and the last set were bagels! He’s a good guy, but he talks a HUGE game. It’s very entertaining actually.

      The good thing is, now we know we can play 4.5 hours straight! Therefore, the normal 1 hour 45 minute matches come official match time is nothing to us now! Bring on the battles, baby!

  5. says

    Wow – my longest match was close to a 3 hour, 3 set match in high school. I’m definitely not in as good of shape as I once was an I think anything over 2 hours would do me in now. It’s a good thing I haven’t challenged you to a tennis match yet – sounds like you got skills. ;)

  6. says

    Nothing like competitive sports to really get to know someone’s personality. I can be stubborn when investing, holding onto a beaten down stock despite what analysts say. ┐( ̄ー ̄)┌

  7. says

    There’s that country song by Kenny Rogers I believe, talking about how we must “know when to fold em, know when to walk away, know when to run”. Wise words, actually.

    Competitiveness is a great success trait. That being said, I think it’s important to have control over one’s emotions and be able to assess a situation clearly. We can’t win everything. There are some situations where we will lose and lose badly no matter how much we desperately want to win and think we’re better than the next person. Sometimes, even then, the other person is simply better than us and always will be. Period.

    Again, know when to fold em, know when to walk away….

  8. says

    Maybe for him the money itself wasn’t really an issue and he knew he would lose. Sometimes we like pitting ourselves against situations we know we can’t beat but we try our hardest regardless. He may have been the one playing you, egging you on to beat yourself up to push himself yet further. You say you tend to play the underdog but you do so with a slight smugness (you went into this knowing you would win).

    So, in that light the point is the competition doesn’t matter. I’m pushing myself in running now I have NZ for myself (Cairo wasn’t a running city). I either have myself or another person to push myself against but never is it personal and i’ll be honest beating others doesn’t give me that much satisfaction. I’d say I almost fake appreciation when I do win so others don’t think I am odd! What drives me on when running in groups is the awesome thought that others like running like I do :).

    We should compete but shouldn’t gloat. When others are consumed with winning we should back out and not let them feel that toxic satisfaction or disappointment. After all are we not all in the game of life together? Winning can be fun but that is where it should stop. It really is not a genuine achievement. The real achievement is beating yourself.

    Still, well played Sam :).

    • says

      You reading a lot of Buddhism books lately?

      If you played tennis, or a sport that it’s one against one, you will have a better understanding of what I discuss. For the moment the match starts, it is all out WAR, and it doesn’t matter if we are best friends. This is the spirit of competition.

      I never go into a match against someone rated my same level and think I will lose. I always believe I will crush them. In tennis at least, 50% of it is mental. The other 50%, it is assumed that one is in tip top physical shape eg 6 feet, 160-165lbs. One needs to be mentally bold to win, bc that is the X Factor.

  9. says

    Two hundred bucks, sweet! Your opponent wasn’t a total pushover, going down in some sets 6-4. In his mind, it may have been just a matter of small errors and a couple inches on the baseline. This stubborn streak probably serves him well in whatever line of business he’s in.

    • says

      The 6-4, 5th set was a nerve wracker. If I had lost…. I donno if my body would have held up b/c of cramping. I’m glad I started strong 6-0, and ended strong 6-0.

      Losing a set 4-6 definitely brings belief in the ability to win. But not losing 0-6. That’s a different game.. that is a mind game 100%.

  10. Rachel says

    I can feel his pain, especially if he thought it was errors on his side causing him to lose. I usually beat myself instead of my opponent beating me, and that is the most frustrating thing ever. Now based on the set scores, I’d say it was more than him beating himself. I’d rather my opponent beat me than me beating myself. It’s so much more satisfying when you feel like you did your best even if you lost. I played to 8 last night because we only had the court for an hour and lost 8-7. We were on serve coming into the last game and played to deuce. The last rally was amazing. I’d love a rematch, but that’s because the game was so satisfying.

  11. says

    That’s all kind of silly. If he’s actually hurt with a shoulder problem, or bent toes, or whatever, clearly he’s not going to get better with time. So, either he made that up, or he really is just stubborn.

    Enjoy that $200. Sounds like you had to put in a lot of sweat equity for it.

    • says

      Stubbornness, pride, and more pride. It’s the same thing with me, risking a knee injury or major cramping just to try and win. $200 is nice, but it’s not nice if I got injured!

      At least now I know I can go the distance. 6 sets gives me more confidence that even if I go 3 sets, it’s not a problem at all. Battle tested!

  12. says

    Great story and well done for winning. As to quitting, I don’t seem to be very good at it either. But if I were to quit how am I going to finish a marathon? Everybody want to quit at mile 17! As someone said: “It will be OK at the end and if it is not OK it simply means that it is not the end”.

  13. Dollar Disciple says

    Congrats on your victory! What doesn’t kill you makes you stronger. Until it kills you!
    But seriously, this guy sounds pretty cocky and that kind of person will rarely admit defeat. At least he gave you some credit, begrudgingly.

  14. says

    That sounds like it was an exhausting day, but at least you earned 200 bucks. Most times I’ll realize that I might need to back off and accept defeat with one exception. I rarely gamble anymore, but if my number doesn’t come up on Roulette, I would keep playing until it did. Usually I would at least get my money back, but I should walk away if it doesn’t happen sooner. :-)

  15. Joan says

    Hi Sam, it’s Joan from Man Vs. Debt just stopping by to say hi. I’m a tennis player too – so I LOVED that I happened onto this post! I really identify with this – I’ve been in over my head a few times in life, and the results have really varied. Sometimes, persevering has been incredibly worthwhile (aiming for my black belt in tae kwon do, despite some pretty major injuries and health challenges along the way), and sometimes, persevering has been stupid (refusing to give up a part-time job that wasn’t a good fit, because of the potential minimal benefit financially.)

    I’m with Jen above, by the way. I don’t gamble often, but I NEVER quit while I’m ahead. I just play until I’m back where I started. Thankfully I don’t bet more than I can afford to lose :)

  16. says

    Doh! Sorry to hear about your hip! Take care of yourself OK? I hear you loud and clear, and I wonder when my knees will start giving out. It’s just a matter of time!

    Glad you won though!

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