Three Big Lessons From the 2016 Chicago Cubs

I’m a White Sox fan but I really enjoyed watching the 2016 Chicago Cubs win it all. My wife is a Cubs fan so this was the pinnacle after a lifetime of disappointment. 

As I watched this team and thought about the big picture, there were three big lessons I took away.

1. Sometimes you have to tear things all the way down to build them up.

Theo Epstein, the Ricketts family and the organization made a choice – spend money on the future at the expense of the present. This team lost 91, 101 and 96 games in 2011, 2012 and 2013. The reason is that Theo and the front office tore down the organization to its very foundation.

Fans understood and supported this move, especially at the beginning. Then it got tough because losing… well, it sucks. 

But the Cubs never wavered. They believed in the overall strategy, the big picture. To be great, they had to change everything about the culture. They had to be self-honest.

And it worked. The Cubs overcame 108 years of “wait ’til next year” and showed why this was the best strategy.

I started this blog to do the something similar, although not nearly as dramatic or impactful. To understand how to be my best self, to win my own championship, I have to tear down my psyche to its very core. This is the only way to fully heal and create positive growth.

The Cubs understood what it would take to win – the pain, suffering and reflection. Do we?

2. Hard work and fun are not mutually exclusive.

I’ve never seen a team more relaxed than the Cubs in games 5 through 7, with little exception. Anthony Rizzo looked like a kid in little league watching the game versus playing it on the biggest stage at the highest level. These guys had fun!

Even the stoic Kyle Hendricks and the perpetually cranky John Lackey looked like they were relaxed, even if not having Rizzo-like fun. The point is these guys were working really hard and having fun, even when losing. I’m sure they were down at some point. As I said, losing sucks. But they found a way to relax, have fun and that’s when the magic returned.

The biggest rain delay in World Series history highlights the point. After giving up the tying runs with 4 outs to go, the team could have tensed up, thought about a stupid goat and gone out and lost. And most teams would.

Instead, the 2016 Cubs had a players-only meeting, relaxed and went out to win. They were having fun while working hard. Once again, the look on the face of Rizzo standing on third and shouting at Ben Zobrist told the whole story. And they won.

All I can think of is how many years I spent dreading hard work when it came to personal growth. Hard work at work, sure. Hard work at home, ugh!

If I embrace the hard work as fun, as I did with running, then there is no doubt success will come more often and taste sweeter. I’m still working on figuring out how to translate this to my other problem areas. But knowing is at least half the battle.

3. Support is better than finger pointing every single time.

And speaking of that players-only meeting, holy freakin’ moly was that amazing. That meeting was called by Jason Heyward who, by any measure, had a pretty awful postseason. Many were questioning the big dollars spent to bring him to roam right field for the Cubs. But I think he earned every dime with that speech.

The players stuck together. No blame laid. No fingers pointed. No hostilities. No ego. Just one team.

Your support system matters. The Cubs are the embodiment of how an entire organization works best. From the lowest level scout to the likely league MVP, the Cubs support each other. 

Like a family or good friends, there had to be moments where this broke down. But it was the exception and not the rule.

This may be the biggest lesson of all. We all need to surround ourselves with people who will build us up and never tear us down. People who will carry us when we can’t walk. People who will smile in the face of our pity. People who will reach out to just see how we are doing, at that perfect moment, even though there is no way they could have known.

If you are like me and struggle with eating, these are the people that make you happy about eating a salad versus a pizza. These are the ones that won’t judge you for eating that pizza but only help find ways to enjoy other choices. If you struggle with alcohol, these are the people that hang out with you when you’re sober as well as pick you up when you lose control. They don’t enable, they heal. They don’t judge, they love. They don’t walk away, they hug.

Your support system matters. Don’t be afraid to walk away from the big free agent to find the dependable role player that wants to be on your team forever. Understanding that I’m worth enough to be around has taken a lot of reflection. I forget too often. I’m lucky enough to have a support system that wants to help. I’ll fail again soon and they’ll be there. Your support system matters. Maybe I’ve said that already?

The 2016 Chicago Cubs taught me a lot. Failure is fleeting. Effort is forever. Never give up!