Win The Small To Conquer The Big: A Life Strategy

Win the small to conquer the big

Win the small to conquer the big is a strategy to help you succeed at bigger things in life. By winning the small stuff, you will naturally develop more confidence and more skills to tackle new challenges.

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. I had to also figure out how to lead a group of men and women I hardly knew. There was so much anxiety about not looking like an idiot that I dreamt of several players making fun of me for drafting so poorly.

Let's go through 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. 

Win The Small To Conquer The Big: The Strategy For Winning It All

Here was my strategy to win the Labor Day softball tournament!

1) Sleight of hand. Stay low key

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.

Creating An Illusion

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 Petros who couldn't run well, a veteran guy who had a lower batting average than me (.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:

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

Petros: 0-4, a walk, 1 RBI

2) Do not underestimate the power of preparation.

To conquer the big, you must prepare like mad.

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. Instead, 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. Strange! We lit up left field in the championship game like Independence Day and scored four runs.

First Isn't Always Best

When asked whether I wanted to pick 1st, 2nd, or 4th in the draft after Petros, 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.

Know Their Tendencies

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. Petros 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. Being a great leader is a great way to conquer the big.

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 - Conquer The Big

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.

Introduce A Team Philosophy

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 1-5 with two strikeouts in the final game. This is slow pitch softball folks! 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.

Related: Two Retirement Philosophies To Determine Your Safe Withdrawal Rate

Know Your Weaknesses

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 - Win The Small To Conquer The Big

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 To Conquer The Big

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.

To Conquer The Big

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.

Related: The Secret To Your Success: 10 Years Of Unwavering Commitment

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 for playing hard.

Win And Win Some More! Hooray For Softball

In the end, despite getting little recognition for captaining 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. If you’re someone who puts in maximum effort into even the little things, I want you on my team for the next tournament!

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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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About The Author

14 thoughts on “Win The Small To Conquer The Big: A Life Strategy”

  1. Nothing feels better than a win…and I guess I won’t hold it against you that you didn’t draft Clint first;)

    I’m surprised you wanted to pick and lead a softball team. I play a lot of intramurals and it seems a majority of slow-pitch softball players think they are the greatest thing since sliced bread…despite the fact that a most can barely make it to first base without gasping for air lol.

  2. How cool! Congrats on that win! What a fun way to put your in depth analytical skills to good use. You are quite a natural coach! It takes skill to put a team together and then coach everyone to victory!

  3. Congrats Sam! It sounded like you were sandbagging the commissioner so that you’d be in a prime position to pounce when the opportunity presented itself. :-)

    Did they know about your strong tennis background? I picture you pulling a Woody Harrelson in white men can’t jump to set the whole thing up.

    Fun read. Thanks for sharing the experience.

    1. They don’t know about my actual softball background. Growing up overseas attending international schools, the boys actually played softball instead of baseball in Malaysia. It was interesting, but very fun.

      There’s a big softball/baseball culture in Asia. Think about Japan and Taiwan doing well in the world series little leagues. And some top Japanese professional baseball players today in the MLB. Whoo hoo!

  4. Congratulations on the win! It’s nice to see strategy and preparation rewarded.

    We can succeed in life, like you did in your softball tournament, with preparation and surrounding ourselves with people who will support us and not selfishly look out only for their own interests and needs. Way to avoid the malcontents and individuals who would only care about their own performances. The captain of the team with the left fielder with the shoulder utterly failed his team as a leader.

  5. Martial arts Mama

    I love this story! You are such a strategist in everything you do, and it pays off! I agree with your philosophy too, and always tell my kids that God is in the details. If they take care of the little things, the big things will take care of themselves.

    Awesome job, and keep the stories coming:)

  6. Your preparation and attention to detail are admirable and your small victories compounded to give you an advantage. It’s easy to see how this mindset helped get you to where you are now.

    Effort, preparation, and adaptability often get you farther than talent alone. You can see this in the workplace all the time. The smartest guy in the room isn’t necessarily the boss, but the person who minds his details, aligns his team’s priorities to accomplish the task-at-hand, and focuses on things within his control. An effective leader exudes confidence by making tough decisions and maximizing the team’s strengths while minimizing its weaknesses. Few teams are comprised of perfect individuals but imperfect individuals can combine to become perfect teams. It’s about working together toward a common goal. The best leaders bring this out of their teams.

    Applying this mindset to any area of life will provide tremendous rewards. The question becomes if you will apply yourself and execute. Thanks for sharing!

  7. It really is amazing to see your thought process as a captain and obviously the hard work up front paid off with amazing dividends.

    The best part is that this was just a small proof of concept that you obviously have already taken advantage of with the financial success you have had in your other endeavors. I love when you are able to take blueprints from one aspect of your life and use it to create success in other aspects.

    A casual observer may have viewed that game as luck (and I’m sure the losing teams rationalized it that way) but you have eloquently shown that you helped design the outcome by great upfront preparation.

    You may have found your second calling, already winning a tennis championship and now softball tourney. You need to set you aspirations higher, how bout using your skills and analytics, helping the Cleveland Browns rise up from the bottom in the NFL? :)

    1. Hah! May I be so bold as to predict the feeling of winning a HS conference championship or Labor Day softball tourney is the same as winning the Super Bowl. I really found no difference in the joy and sense of accomplishment I felt after the tournament was over versus getting a big promotion or seeing an article on FS go viral. It’s all the same… put in the work, and when the outcome is positive it feels awesome.

      I love how Baker Mayfield was not recruited to playing football at D1 schools, walked on to Oklahoma, ended up winning the Heisman, going #1 in the NFL draft, and breaking the Browns 19-game winning streak. If he can remain humble and professional, Baker will do well.

      It’s the intangibles that make such a big difference. A good scout or hiring manager or founder or life partner will be able to identify those with an X Factor.

  8. Ms. Conviviality

    Congrats on the win! Having not play organized team sports before I didn’t realize how much strategy and planning go into playing and WINNING a game. As I’ve said before, I’m always learning something new from this blog. If I’m ever in a position to make hiring decisions, I would look at any team captain with decent wins in a different light. It’s likely they have good team building and analytical skills which are very important in my profession.

    Our office attends a conference for internal auditors annually. The speakers are from other institutions sharing their expertise to help others conduct audits better. Two weeks ago I was one of the speakers. This was my first public speaking engagement ever to a large group of about 100! Luckily, my session was on day 3 of the conference so I had plenty of time to practice in my hotel room, in addition to the notecards I prepared prior to the conference. While other attendees had a half-day of sightseeing the previous day I was holed up in my room. The preparation paid off because on day 4, I was sitting one row behind two women and I overheard one woman saying how there were a couple of really good sessions during this conference like the one yesterday and she named my session! :)

    1. Gracias! During interviews, I always ask the candidate to tell me a story that has nothing to do with the job, on defeat and triumph and how they got there.

      So awesome on your public speaking! A top 3 nerve wracking experience for sure. Congrats!

      Nobody will ever regret preparing the best no matter how small the project. If there’s a stumble, it’s easier to move on because there was nothing more you could do. If there’s a win, well, that win will last you for the rest of your life!

    2. Young and the Invested

      That’s great! Public speaking can be challenging. I’ve spoken a handful of times to large audiences and feel they’re easier than small, more intimate gatherings. I’ve found when there are rooms full of people, it’s hard to distinguish people from one another and it makes me less nervous about how they’ll react. I won’t be able to see the individual reactions, they can be zoned out on their phones, or be focused on something else. As a result, it feels easier, though I would like their attention. It’s the intimate settzings of 20 or fewer where you can make direct eye contact with everyone and feel like they’re more present.

      But it sounds like your presentation went very well and people were delighted to see it. Hearing that must have felt very gratifying. Kudos!

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