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I've been in a fantasy baseball league for six seasons now.  It's a ‘keeper' league, meaning that we carry some of our players over from year to year.  This means that identifying talent early and knowing when to hang onto it is key to success in the league.  With the league in a pretty mature state, success comes through a combination of identifying young talent, drafting well, trading well, and making good pickups throughout the year.  Few teams are successful without having a mixture of all of the above components.

  • Applied Lesson: Keep a balance in life (balance your work life and your personal life) and in financial decisions like investing (keep a balanced portfolio)

I've had a very successful run in our league.  Knowing that I was joining an established league and knowing the setup, I knew walking in that I would probably not be able to compete for the first two years.

  • Applied Lessons: Know what you're getting into.  Set targets and goals based on realistic expectations.  Had I said ‘I want to win it all the first year', I might have quit.

The first two years I was in the league, I concentrated on building my team, which consisted of evaluating and adding a lot of minor league talent.  I also became more familiar with baseball as a whole, as well as the nuances of playing fantasy baseball.

  • Applied Lesson: Learn the ropes!

Along the way, I made a lot of mistakes.  I made some bad trades, bad drafts, and let go of good players too early.  But, each time I made a mistake, I learned from it.  Conversely, each time I made a good move, I tried to learn from that as well.

  • Applied Lesson: Learn from your past experience.

In the third year, I started seeing results.  Some of the young guys that I had obtained early on were no making it into the majors and turning into excellent baseball players.  In my third year, I finished in third place, which was good enough to make me some money for the year.  I carried that momentum forward into my fourth year, where I was able to unseat the five time defending champion and win the entire league.

  • Applied Lesson: Celebrate!

In my fifth year, I was unable to defend my title, but I did come in second place.  That was three years in a row that I had made money from the league.  That second place finish was the end of last season.  Looking at my team, I knew that I was probably winding down.  Just as with most professional sports, very few teams can win year after year.  Salaries get too high, players start getting older, and luck just starts running out.  I was preparing myself for one more year of winning some money before knowing I'd have to make some changes, and probably keep myself out of contention for a year or two.

  • Applied Lesson: Plan ahead!

The year started and it didn't start too well.  I didn't panic, because for whatever reason, my teams have usually gotten off to slow starts. It's usually about a quarter point through the long season that I would start picking up steam, and I was hopeful that it would play out this year as well.

  • Applied Lesson: Pace yourself!  In years past, if I would have panicked after a slow start, I could have ruined things.

Well, I waited and waited and this year, things didn't get any better.  I was mired in the bottom half of the standings.   Around the All Star break, if you're not in contention, there's very little chance that you are going to make a run to get you into the ‘money' (aka the top three).  I knew that my re-building plan would need to commence a year earlier than I had thought.

  • Applied Lesson: Know when to hold 'em.  Know when to fold 'em. 

I've got a lot of good players on my team.  I knew that I had assets for trades with other owners.  These owners would be the ones at the top of the standings who were looking for an edge to separate themselves from the owners nearby.  Having been there for the last three years, I knew the excitement and anxiety that came.  I also knew that, just as happens in pro sports, owners are often willing to make deals where they will give up young players (aka the future) for veterans that can get them the glory that comes with a championship.

  • Applied Lesson: Know your audience.

I started making some inquries and it didn't take long before I had a biter.  One of my franchise players is Hanley Ramirez, the shortstop for the Florida Marlins.  He's been my shortstop since pretty much forever, and he's reaped many rewards, often being touted as the best fantasy baseball player.  I was able to turn him (as well as a random pitcher) for three players that I could keep next year (for those who know baseball, I got Ubaldo Jiminez, Pedro Alvarez, and Michael Pineda).  That three for one deal potentially benefits us both, it gives me three players I can use in 2011 and beyond and it gives the other owner an immediate boost in the standings if HanRam delivers.

  • Applied Lesson: Negotiate something that potentially benefits all parties involved.

I'm probably not done yet.  I have a few other players that hold value that I think I can use to trade in for potential future glory.   But, I have a clear plan because I know that if I go overboard, I could have all these guys that might not do anything for me for two or three years.  I don't want to turn into the forever-rebuilding New York Knicks.

  • Applied lesson: Define your strategy in clear terms.

Will this work?  I hope so.  Is it guaranteed?  Heck no!  In the time I've been in this league, most teams that try to improve either have never been good in the first place or try to re-build on the fly, without making wholesale changes.  However, two instances come to mind of a situation similar to what I'm trying to do, where blue chip players are traded with the direct intention of getting worse now to potentially improve later.  Of these two times, one attempt crashed and burned and the owner is still stuck in neutral three or four years later.  The second time worked great, and the team is now making a run for it (and happens to be the team I just traded HanRam to).  Obviously, I'd prefer to have things turn out like it did for the second owner, but you never know unless you try.

  • Applied lesson: Nothing ventured, nothing gained.

We'll see how things turn out.  In any case, it will be fun, and in the grand scheme of things, isn't going to make a whole lot of difference.  It's a lot more devastating when the Knicks screw up yet another trade than for my team.

In any case, there are obviously a lot of life lessons that you can apply (and learn) from fantasy baseball and I thank you for having allowed me to share some of those which I've observed.