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Life Is A Series Of Games: Only Play To Win

Life is a series of games. Sometimes you lose, sometimes you win. We all know this. And yet, we often keep on playing games we lose. Why not play to win? Don’t you enjoy winning? I do. You know what I don’t like? Losing.

I don’t mind losing a few games, but overall, I want to win. And I don’t think you’re any different. I’ve never met a person who said, “I LOVE to lose.”

That person doesn’t exist. People who pretend they don’t mind losing gave up on life years ago. I get it. Life is hard and when you lose a lot, you become numb. That’s why this concept is so important.

Losing Hurts

Look, you can be the most optimistic and thick-skinned person in the world, but if you always lose, you’ll go crazy. You can read as many self-help books as you want, and master any kind of subtle art you want, but if you lose, all that shit goes out the window.

I don’t understand why people are never honest about losing. It hurts. And this is coming from a person who’s not even that competitive.

I always played sports as a kid. And even though I was pissed off when I lost, I could let it go. I had friends who were so competitive that they couldn’t stop before they won something.

Didn’t matter what it was: 1 on 1 basketball, video games, table tennis, foosball, whatever.

It’s not in our nature to be happy when we lose. You know how most people solve this problem? They give up!

That’s the saddest thing I’m currently seeing. And I see this a lot. Every time talented people give up their career and become minimalist yoga practitioners who live off the land, I see someone who stopped playing.

Of course, this is not the case for everyone. But let’s be real. I’ve been there before. When I started my business in 2010, I hit a wall after three years. I stopped playing the entrepreneurship game and decided to climb the corporate ladder.

When I worked at a corporation, I realized that it was not a game I was good at. I stopped climbing the corporate ladder.

Find A Different Game

To be honest, if you’re not good at a particular game, it’s better to stop. Go and find a different game you can win at. But don’t give up and live in the woods.

Jerry Seinfeld explained this concept best in an episode of Comedians In Cars Getting Coffee. In the episode with Eddie Murphy, they talked about why companies that are in second place should just quit. Jerry said:

“All these companies that are in second place that hang in there. Why don’t you just quit? Avis, Colgate, RC Cola, just quit. How sad is it to work at these places? You’re never going to catch them [the #1 company]. Pepsi… You’re never gonna catch them.”

Obviously, Jerry is joking here. But there’s a lot of wisdom there. If you can’t be number one, why play? If you can’t win, it’s just a hobby (nothing wrong with hobbies, though). Quit that game and start playing a game you can win.

Let me give you a recent example. A lot of people told me I should make YouTube videos. I’ve been teaching productivity and writing for several years. And I also have a podcast.

It didn’t sound like a bad idea to me. So I got into the YouTube game. I’ve published 38 videos on my channel and tried many different strategies to reach more people. My conclusion? I wasn’t even close to the top perfomers on YouTube in my field. So I quit.

Same thing is true for my podcast. The difference is that my podcast takes less time and is more fun to create. But still, I never came close to the top podcasts in my category. That’s why I allocate less time and resources to it.

Win More Than You Lose

When it comes to content creation and monetization, my main focus is on blogging, teaching, and publishing books. I’m good at those things and the results are much better—and so are the rewards.

For example, my book Think Straight has been consistently sitting at the top of its category. And even though I might not be #1 in certain categories, I’m very close.

That’s the key. Seinfeld was joking when he said that Pepsi should quit. I think he’s more referring to the players that are not even at the top. In this case, Pepsi is pretty close to Coca-Cola. Will they ever catch them? We don’t know but they are up there.

Can you see the top of your field? Can you finish in the top 10? If so, you have a chance to win. And sometimes, you don’t even have to be #1. If you’re at the top, you will still reap the benefits, just like Avis, Pepsi, etc.

But if you can’t be at the top, I would find a different game. In This Is Marketing, Seth Godin wrote about how we only see the winners in any given field:

“We hear about the outliers, the kids who make millions of dollars a year with their YouTube channel or the fashionista with millions of followers. But becoming an outlier isn’t a strategy. It’s a wish.”

We don’t see all the people who lost. The winners are highly visible— especially in desirable fields. Those folks are the famous outliers. But that doesn’t mean you can’t win at other games.

It’s pretty harsh. And a lot of people don’t agree with this theory (I already received a bunch of emails from angry people). But that’s not a surprise. Just look at how many people work at places that don’t even compete.

Pick Your Games Wisely

There are a lot of games that I lost—which is never a good feeling. When I realized I didn’t even come close to success on YouTube, I had to pull the plug. It simply wasn’t yielding any significant results.

Another example is individual stock picking. That’s really not my game. So I stopped doing that. Instead, I invest in index funds and real estate.

Sometimes, you don’t need to go on forever to draw conclusions. “But what about persistence?” Well, you can’t be persistent with everything. I’d rather be persistent with one or two games that I’m good at. You only have so much energy every day. Can you do it all?

I don’t know about you, but I certainly can’t. This concept is not for everyone. There will always be delusional people who say, “Look at how often Thomas Edison failed!” Sure, but he played the invention game and was winning overall.

There’s nothing wrong with quitting so you can win at something else. Just don’t settle for average. Again, Seth Godin has excellent thoughts on this:

“Quit or be exceptional. Average is for losers.”

And you know what? Maybe it’s not the right time to win. Maybe you’ll lose at something and come back at a later stage. So when you quit a game, it’s not forever. Sometimes you have to quit to get better so you can win later.

Either way, when I focus on too many things at the same time, I start dropping the ball more often. I make mistakes, I forget things, I slack off. You can’t have that if you want to win.

Winning ain’t easy. And there’s little room at the top. But that doesn’t mean you can’t be at the top of your game. You just have to pick a game you can win at.

Life is a series of games. Sometimes you win, sometimes you lose. Why not play to win? Don't you enjoy winning? I do. You know what I don’t like? Losing.

You Play to Win the Game

FEBRUARY 21, 2019 | THE PALOMAR GROUP

It was a 2002 quote by Herm Edwards that will go down in sports media history, “That’s the great thing about sports, you play to win the game.” 16 years later, the quote still resonates. It came after a reporter asked him a question following a loss to the Cleveland Browns that left the Jets 2-5. After the speech, the Jets went on to go 7-2 and win the AFC Eastern Division Championship.

As in many other lines of work, the adage rings true in the Investment Sales business as well. All too often as a boutique Investment Sales Firm out of Augusta, GA, we are competing with large, multi-billion national firms located in major markets to represent clients in the sale of shopping centers, multi-family communities, NNN assets and more. Oftentimes we are met with a roadblock from those responsible for handling dispositions on behalf of ownership groups or even by the owners themselves, that they just have to use the big guys. The rationale that we hear time after time when this happens is “If this deal doesn’t sell, I just can’t tell my investors that we used a small shop like Palomar” or “We just have to use a national group.”

The thought process behind this is understandable and more times than not, attributable to self-preservation. In most situations, the employee is responsible for executing on a multitude of dispositions and he is concerned for the safety of his job if he does not succeed. If a deal couldn’t be sold, the employee can at least go back to his board and say “well, it wasn’t my fault, we went with the biggest group in the business to sell our deal.” The problem is that while that employee may not lose his job or ruffle any feathers internally by going with the big shop, he is also not going to turn any heads and over deliver on investors expectations.

All too often we hear from disappointed clients who have gone with big shops in the past only to be dissatisfied with their lack of engagement, lack of effort, and lack of execution. We constantly hear things like:

“I never even heard from ____ after we gave him the listing …”


“We gave _____ the listing because we had a relationship with their top guy. We were disappointed when the deal was just given to junior associates to run with.”


“They didn’t do anything with the deal, they put it online and waited for calls to come in.”

Our teams background in development at the Palomar Group uniquely qualifies us to giving our clients the best on deals we list for them. When working with us

  • Deals are always led by one or more of the firm’s partners
  • You work with the same group whether selling a deal in South Beach or the South Side of Chicago. Deals never have to be passed on to other regional shops.
  • We do more than send email blast out, post the deal online, and wait for the calls to come in. We get creative on deals finding unique ways to maximize returns for our clients by proactively finding the best buyers at the highest numbers in the market today.

In today’s market, Sellers need more out of their Investment Sales Broker. Gone are the days of Best and Final Offers where aggressive offers were flying in. In most of today’s transactions, being that many of them are value add products in secondary and tertiary markets, there are one or two qualified buyers who are ahead of the rest on pricing. More times than not, that buyer is found as a result of your broker rolling up his sleeves and thinking outside of the box. Relying on bigger firms to handle your project will be comfortable and safe, but you could ultimately lose out on a much better deal.

When looking to execute on your disposition strategy over the course of the next year make sure that you are playing to win the game and not just playing to stay alive.

You Play to Win the Game FEBRUARY 21, 2019 | THE PALOMAR GROUP It was a 2002 quote by Herm Edwards that will go down in sports media history, “That’s the great thing about sports, you play ]]>