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Win The Small To Conquer The Big: A Life Strategy

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I recently experienced one of the most satisfying experiences of my life. I’d rank the feeling right up there with getting into college or landing my first job.

As a first-time captain, my team won the annual Labor Day weekend softball tourney! There were 40 players, and I was chosen as one of four team captains to do a player draft, make a batting lineup, and decide on fielding positions.

This was an exhilarating experience because I had zero experience. I had to do a lot of research in the hot tub about each individual player and figure out how to lead a group of men and women I hardly knew. I had so much anxiety about not looking like an idiot that I dreamt of several players making fun of me for drafting so poorly.

I want to go through with you some of the strategic processes that affected this positive outcome. You’ll be able to decide whether preparation means anything. Maybe you’ll change your attitude about how much luck and effort play a part in achieving your goals. Or maybe you’ll simply not make the connection that how you approach small tasks can make all the difference when it comes to tackling bigger missions. 

The Strategy For Winning It All

1) Sleight of hand. 

I joined this softball league because I needed some diversification from tennis. My goal was to find some new friends to hang out with over a game that I love. Early retirement can get very lonely sometimes.

With over 1,000 players in the meetup group, and 100 regulars, I quickly began to observe who were the easy going folks and who had bigger egos – you know, those guys who love to relive their high school glory days (like I might do with this experience in 20 years) or who repeatedly bring up blue moon plays they made that nobody remembers. Good thing we keep stats that shine light on reality.

Instead of trying to be the best player, I just tried to take it easy and have fun. I didn’t want to injure myself in a recreational activity that would negatively affect my ability to take care of my son or play league tennis. I was already suffering from lower back pain.

For example, I’d bat lefty instead of my normal righty just to test it out, disregarding how it might negatively affect by batting average. I’d play right field, where fewer balls are hit, no problem.

To the players, and to the Commissioner (organizer), I was known as the easy going utility player. The Commissioner would constantly tell me to get down for balls, use two hands, swing harder, and run faster. Clearly, I wasn’t very good in his eyes. Perfect.

When it was time for the Commissioner to choose tourney captains, he chose four players whom he thought had similar abilities. Me, a 58-year-old guy named Peter who couldn’t run, a heftier guy who had a lower batting average than I (.500 vs .582), and another guy with suspect fielding skills and an even worse batting average (.458).

This situation was perfect because I strongly believed one of the X Factors for winning was the captain’s performance on the field, not just his analytical abilities. This experience is different from winning a fantasy football league because my physical performance mattered.

Here are the hitting stats for the championship game between me and Peter, the other captain who could run:

Me: 3 singles, 2 doubles, one out, 4 RBIs, 1 run

Peter: 0-4, a walk, 1 RBI

2) Do not underestimate the power of preparation.

After playing in the softball meetups for a year, I had a pretty good idea of the skill level of most of the regulars. However, there were about 5 out of the 40 players in the draft pool who I didn’t know.  So, I did homework and looked up their stats and asked around. I was also aware of my own player biases.

I drafted based on defense, intelligence, fighting spirit, and harmony. Players who thought they were better than they really were, were not picked. Players who wanted to be a hero when the bases are loaded, instead of taking a walk when they were ahead in the count, were out. Players who loved to hit under pressure were in.

I focused on drafting the best available shortstop possible, the best available left fielder, best third baseman, best center left fielder, best pitcher, best center right fielder, best second baseman, and finally the best right fielder. As for first base, I knew I could play it just fine.

While the other captains picked showy big hitters, I was focused on choosing the best fielders because defense is what wins championships. For example, one of the captains picked a big hitter who could not throw the ball farther than 30 feet because of a shoulder injury. Yet, this player insisted on playing left field instead of first base. Absurd! We lit up left field in the championship game like Independence Day and scored four runs because of his inability to throw.

When asked whether I wanted to pick 1st, 2nd, or 4th in the draft after Pete, the 58 yo picked 3rd, I chose to go 2nd. I knew everybody wanted to choose Clint, an obvious top choice. But because we are friends, I knew he would be hosting two consecutive nights of salsa parties the Friday and Saturday before our Monday softball tournament. Further, he hadn’t played in the two most recent games, so he may have been rusty.

So, I zeroed in on Roger, a power-hitting left-handed batter. The ability to pepper right field with bombs was my #1 goal given teams often put their worst players at either RF or catcher. I figured teams with a poor defensive strategy would not shift a good fielder into right field when Roger is hitting.

I also figured the Commissioner would put me on the worst field next to a sewage plant, which had a shorter right field than the better field (derivative thinking). My gambit worked. Clint, who was picked first, went 2-5 in the consolidation game, while Roger went 4-6 with a walk and 4 RBIs in the championship.

As a rookie captain, I knew the three veteran captains would try to take advantage of me once the draft was over by making some preposterous trade proposals. But I held my ground and was secretly bemused by some of their draft picks.

For example, one captain, who loves the ladies and is single, really likes this one particular girl. As a result, he drafted her in the 5th round, when based on skill set, she should have been drafted in the 7th or 8th round. Peter, the 58 yo, drafted two pitchers, even though he was already the best pitcher! This caused one of the pitchers he had drafted to become extremely bitter. He publicly wrote on the message board, “this makes no sense!”

Control what you can control through extensive preparation. If you study for only 30 minutes before a final exam and get a C, that’s on you. Why not study for 10 hours and get an A? If you sleep in every day when your competition wakes up at 5am, you must live with the results. You will never regret trying your best when it’s all said and done.

3) Be a leader and set the tone.

If you make me the leader, I am going to lead by example through hard work and preparation. Once you get the respect of your colleagues, it makes working towards a mission a whole lot easier.

The first thing I did was create this easy to read chart with various fielding and lineup proposals. I printed out copies for all my players to review. Then I created the team philosophy. No other captain did this.

Team Financial Samurai Softball Labor Day Tournament Victory 2018
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I then took several of the veteran players aside and asked them to weigh in with their thoughts. It was not only important for me to make sure I didn’t have any blind spots, but it was also important to get the veteran players to feel included.

Once I got a consensus agreement from the entire team for field positions and the batting order, I appointed an outfield captain and an infield captain to keep the communication going. I firmly believe that in softball, having a high game IQ makes at least a 10% positive contribution to the outcome of the game.

Finally, I made sure every teammate read the Team Philosophy at the bottom of my sheet. Given none of us are pros, we were all going to make some type of error. I wanted my teammates to know that making an error was no big deal and to stay positive. People tend to perform better when they feel less pressure.

All but two of my ten teammates maintained positive attitudes throughout both games. One made a snide remark to me when I hit a pop up. He ended up going 1-3 with two strikeouts in the final game. The other negative guy, who found out he had been drafted lower than he thought appropriate for his skill set, went 0-9 and didn’t even try to play defense.

As the team captain, I could have criticized them for their lack of effort and/or positivity. But I knew the 0-9 guy was already emotionally hurting from finding out he’d dropped to the 4th round. Further, he was annoyed that he couldn’t play shortstop because I had already drafted a better one. After going 0-5 in the first game, I decided prudently to not poke the bear. Instead, I kept on being encouraging even though he kept muttering things like, “we’re going to get killed;” “you see, the shortstop missed the ball;” etc.

Even if you feel unqualified to lead, you must lead with confidence. Having a positive mindset matters folks. Know your role. Do it well. And watch the wins pile up once you get buy-in from the team.

The Championship Game

Here is the score sheet for the final game. We are the top row for the score and the team on the left for the lineup. I’m second to the bottom of the lineup and Mr. Negative 0-9 is last.

Financial Samurai Softball Tournament Scorecard
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After two innings, I was worried. The opposing team (bottom row) power hitters were slugging balls past our outfielders. Three of their batters were over 6’2″ and 215+ lbs, and one hitter was a giant 6’10” who batted 0.700! Getting scored on 8 times in the second inning was extremely disheartening. Despite the barrage, I kept the faith.

Slowly, we chipped away at their lead. Down 16-18 at the end of the 6th, we finally surged ahead 22-18 in the top of the 7th after three of us chugged beers because by then we’d run out of water. Not only did we have power at the top of the lineup, we also had power at the bottom.

I decided to let my last pick in the draft, a sufferer of Dunning-Kruger, play second base. Meanwhile, I played catcher the entire game despite the suggestion of several teammates for me and my last round draft pick to switch positions or play my usual first base, which was currently occupied by Mr. Negative. I decided to roll the dice and keep them where they were because we had momentum. You should never change what’s working.

While Dunning-Kruger ended up costing us two runs with two errant throws to first, I managed to even out his lapses with two critical plays at home plate: 1) by catching the incoming throw and tagging out the runner on a bang-bang play and 2) snatching a one-hopper to the plate to save another run.

Final Lessons Learned

Financial Samurai softball
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Despite seeming calm on the outside, on the inside, I was knotted up with anxiety. Behind my jet black shades, my eyes were contorting after each error or missed opportunity. But I stayed positive.

Winning a Labor Day softball tournament really means very little in the grand scheme of things. But it’s how you approach the little things that will carry forward to how you deal with bigger challenges. Win the small to conquer the big!

Here are some final takeaways from the game that may pertain to your business, your job, your investments, or your life.

1) If you never give up, good things just might happen. We started off slow, but heated up towards the end and finished strong. Meanwhile, they cooled off as we made some critical outfield adjustments thanks to our outfield captain. Last long enough and you will eventually catch a lucky break.

2) Never let up until the mission is accomplished. Despite being up 22-18 in the 7th inning, nobody took his foot off the gas pedal. As team captain, I made sure of that because our opponents clearly had the firepower to make up the deficit in just one inning. If you reduce your intensity by 10% because you think your victory is assured, while your opponent increases their intensity by 20% because they’re down, you are often screwed.

3) Know when to motivate, and know when to keep quiet. Managing egos is a huge part of coaching / captaining. You’ve got to make your players / employees feel like they matter the most. It’s important to get them to buy-in to the greater good. Otherwise, their cancer starts to spread.

4) Always analyze risk / reward scenarios and go with the best ratio. If you get your decisions right 51% of the time, in the long run, you will clean house like all the casinos in the world. Better preparation creates a 10% – 20% competitive advantage. As a result, it makes sense to put in the due diligence beforehand and press when the odds are in your greatest favor.

5) Recognize luck and give credit. After we won, I was asked to give a speech. In my speech, I talked about how close all the scores were and how it was just a few unlucky bounces here and there that made the difference, which was true. I gave credit to everyone on my team and pointed out specific plays each teammate made that made a big difference.

In the end, despite getting little recognition for captaining the team or going 5-6 in the championship game, I feel great because I know I’ve continued to maintain the underdog status. Nobody will ever know my sports background or coaching experience.

I hope everyone can find pleasure in the little things in life.


Are You Smart Enough To Act Dumb Enough To Get Ahead?

How To Drastically Improve Your Betting Odds

Be Rich, Not Famous: The Joys Of Being A Nobody

Stealth Wealth: Why You Should Keep A Low Financial Profile

Readers, what are your keys to winning? How important do you think preparation is to achieving a positive outcome? If it’s important, why don’t more people prepare more? What other scenarios do these lessons pertain to in work and in life?

Note: Thanks for allowing me to document this moment. If I didn’t write this post, I wouldn’t remember all the details years from now when I revisit this story with my boy. I didn’t document the historic HS tennis conference victory because kids were involved. 

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