How Do You Play the Game?

play the game

It’s far from unusual for any college student about to graduate to be a bit apprehensive about what their future holds. Questions of whether they’ll be able to find a job, be able to compete with those seeking similar positions, and be able to sustain themselves in the “real world” all start to creep up when the reality of graduation starts sink in. It didn’t particularly help in my case that I was graduating in 2009 with one of the worst outlooks for finding jobs among graduates on top of the fact that I was getting my degree in, of all things, music.

I never thought I’d have these feelings of apprehension though. After all, I grew up knowing exactly what I wanted to do: Be a rockstar. The idea of having an ordinary job and simply “making a living” to “get by” used to make me sick to my stomach, that is at least until I graduated high school and realized that it’s a nice thing to be able to pay my own rent.

So naturally I did what any reasonable person would do, I compromised.

I knew I had the talent, and could do big things, but perhaps it would be better if I played it safe just in case. Something bold like packing up everything and moving out LA to pursue music would be much too risky and “imprudent” for someone as smart as myself. It would seem much wiser to stay where I was in Nashville, a nice enough music city where all my friends and fellow musicians were, and simply get a paying job while I enjoy making music when I could on the side. Then one day, if I was “lucky,” my talent would land me in the right position and I would make it big. (If only I say enough prayers)

The “dream killer” strikes

All was well enough for a period of time after graduation. I did get a job I actually enjoyed, I made some music on the side, and I was able to “get by.”

Then, to my horror, after a year or so I found myself struck with the affliction that kills more dreams and potential than anything else I know of; I got “comfortable.”

Fortunately I recognized what was happening. I consider myself extremely blessed this happened while I was young as opposed to 20 years down the road and then having to endure a mid-life crisis regretting a life of wasted potential. I quickly sought to remedy the situation by starting an in-depth journey into personal growth and self reflection.

The one shift that changed everything

That period of personal development lead to many changes in thinking, but the particular one I look back on as being the “change that brought about all other changes” was realizing I was approaching life the same way perhaps 95% (give or take) of the population does, I was playing “not to lose” rather than “playing to win.”

As soon as I realized that distinction, I knew that any life played on defense could never lead to victory. I would have to consciously decide to pro-actively go after what I wanted and “make” things happen rather than sitting back hoping things would happen. I took personal responsibility for my life and decided I was either going to “make it big or die trying.”

That may sound bold or fearless, but I assure you there was and is still plenty of fear.

It was just that being uncomfortable or trying and failing was no longer the thing I feared most. Rather regret, disappointment, and unfulfilled potential started to scare me a whole lot more. I knew the suffering I would endure of never seeing my true potential actualized would be worse than any failure. I also knew how much this world suffers when anyonedoesn’t share their incredible gifts and talents they have with others out of fear, and I couldn’t bear to hold myself back thereby robbing others in this world of many gifts.

As Jim Rohn says: “We must all suffer one of two things: the pain of discipline or the pain of regret or disappointment.”

After making this shift to play to win, all my thoughts naturally started to change.

Playing not to lose: What if I waste my time? What if I screw up? What if people see me fail? Etc.

Playing to win: If I screw up, what can I learn? I’ll be smarter for my mistakes. Everyone screws up. It’s never a waste of time if I learn something from it. Etc.

Playing not to lose when thinking about moving to LA and pursuing music: The traffic is bad in LA. There’s too much competition. It’s expensive. The people there aren’t friendly. Etc.

Playing to win when thinking about moving to LA: I can spend time listening to audiobooks in traffic. It’s so big there is plenty of opportunity to go around for talented people like myself. I can find plenty of ways to make ends meet. There are millions of people there so I can easily find great friends and business partners. Etc.

This simple change in thinking made the decision to move out to LA and live a life on my terms so stupidly obvious, I almost feel bad for not having seen the light sooner. Plus there was no “forcing” myself to “think positive” which rarely works. And after living in LA for a little while now, I can say that every single fear I had was unfounded and it was one of the best decisions I’ve ever made.

I will note however, the decision to “compromise” for a period of time was the right one. It was actually necessary for me to go through that period not knowing what I wanted in my life or what I was going to do in order to start the journey of self discovery. Those feelings of “not knowing” are the greatest gift we can have when they prompt us to actively seek answers to the deeper questions about our lives and life in general.

It’s not whether you win or lose

All the talk of “how to play the game” or “how” to do anything always comes second to me of a greater question. That is “why?” Why do I play the game at all?

The most powerful motivator we have, which goes beyond simple pain (losing) and pleasure (winning), is that of love. Nothing will move a person or create change more powerfully than love, and when love is the reason why you play the game, you’ll discover you can never win or lose, and therefore worrying about either is trivial.

It’s only when you decide to play the game well because of love can you create a true change in yourself. And that change makes all of us the winner.

Photo by Arkangel

12 thoughts on “How Do You Play the Game?”

  1. “As Jim Rohn says: “We must all suffer one of two things: the pain of discipline or the pain of regret or disappointment.””

    Greatest quote I have heard in a long time. The post was worth it for just that alone.

  2. I agree with Patricia. I already saved that quote and tweeted it instantly!

    Very powerful to look at it in this context. That the true power is in that tiny mindset change.

    From now on… I play to win!

  3. All the best to you, Derek. May the love for music, the love for life without fear carry you through! Last but not least, a sincere “thank you” and “make it big or die trying”!

  4. I haven’t stopped by in awhile, but glad I stopped by today. This was so well written and thought provoking–a great combination. And timely. I’m at a crossroads now where I have to decide which path to take. Your post is just what I needed to read today.

    1. Thank you for the kind words and for letting me know my writing has helped you. It’s very rewarding to know sharing my experiences can have a positive impact on others.

  5. Great post and good positive advice for achieving a successful life.

    When people see my positive view on life they generally want to comment that I must feel comfortable or content. Those two words are, for me, almost fighting words and I try to banish them from my vocabulary.

    Hearing those two words used by others to describe me spurred me on to consider what’s next in my life. Opportunities are endless, need to simply pick one and go with it.

    Comfort and contentment allow one to survive. They do not allow one to live.


  6. Good article – You should never have the mentality of “playing not to lose”, because you are inevitably setting yourself up to lose. I’m a sports fan so I’ll use a sports analogy. In football or basketball when a team builds a nice comfortable lead, sometimes the team with the lead will take the foot off the pedal and play more conservative . Instead of continuing to play aggressive and do the things that got them the lead, they start “playing not to lose”. I’ve seen this happen one too many times where the other team makes a comeback and ends up winning. When you play not to lose, that implies that you aren’t being aggressive with your approach. Whatever you do in life, either go all in or not at all.

    9 year self help enthusiast:

  7. I have to say a heartfelt thank you for this timely piece of food for thought. Playing not to lose and playing to win is such a conflicting notion and you must take time to see on which side of the ledger you are when approaching life and your goals. I have taken this self introspection journey seriously for the past year and have found some things that are powerful and things that need serious retooling for my life to be a external vision of the one I have in my mind. i am actively making changes and have seen the progress incrementally and there is still much work to be done. Thankfully, the journey is on it’s way and I’m glad that I took the time to avail myself of the introspection. I thank you for your post and for Jim Rohn’s quote which is one of the best I’ve ever seen. To your continued success….

  8. Really enjoyed this article. I recently read your Kindle book “How To Stay On a Diet”, and loved it, which moved me to subscribe to your newsletter.
    Your views have really had a strong impact on me and helped me change the way I view things. I am now a devoted reader on your site!

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