Playing To Win in the Game of Life

By Donald J. Strankowski
Ascend Career and Life Strategies

One of the major reasons people find the whole job search process so daunting is that we generally stay within a certain career for most of our professional lives.  We seem to live a world of should do’s; you should go to school, you should get your degree, and you should then pursue a career in that particular field.  You should stay the conservative route so as not to lose your nest egg.  What if you venture out on your own and…. FAIL?  If this mode of thinking dominated everyone’s thought process we would still believe that the world is flat and the moon is made of cheese. You are told stories of entrepreneurs who lost it all and died penniless.  Stay the straight and narrow course and play it safe, play not to lose…so you were mostly taught.

I once worked for a supervisor, who on the one hand was very smart with a high level of business acumen, but on the other hand was extremely conservative in his professional approach.  He once told me, “I always take the conservative path and it has always worked very well.”  Even though this man was very well respected within the organization, I noticed that he was also being passed up on a regular basis for promotions.  He also ended up staying in the same industry with the same company and in essentially the same role for almost twenty years.  I always thought that had this person taken just a few calculated risks along the way and rolled the professional dice when the timing was right, he could have accomplished some extraordinary things.

Sure, there’s something to be said for playing it safe.  But we really never reach our full potential unless we feel the fear and do it anyway—so the saying goes.  Doing that which is uncomfortable is the single best way to grow as an individual and accomplish your goals at a rapid rate.  However, the way we are wired as humans makes it difficult to do that which is uneasy or “scary.”  Our bodies are programmed to keep our heart, breathing, and body temperature at a certain rate unless we forcibly exert ourselves.  Our mental programming also keeps us talking, acting and thinking in a manner that is consistent with the way we see ourselves.  To change your outside world, you need to first work on the inside world and that means forcing yourself to grow and pushing into areas unknown.

Do the thing you fear, and the death of fear is certain.
-Ralph Waldo Emerson

Most people find the job search an uncomfortable practice because they’re actually pursuing a career that they feel they should pursue rather than a career that they really want to pursue.  Most people feel that they are capable of much more but the task of actually pursuing their dreams seems too out of reach.  It takes a lot of courage to turn the boat around and head in a different direction.  Keep in mind every time you change careers, in most cases, you’re starting out at the bottom—again.  And if you decide to start your own business, the risks—mainly financial—are enormous.  Can your ego (and wallet) handle this?  But the bigger question is: What price do you pay for not taking the risk to land a job or start a business you truly desire?

Author Larry Wilson defines playing to win as going as far as you can with all that you have. We all owe it to ourselves to play to win rather than playing not to lose—and there is a big difference.  Playing to win means taking calculated chances and risks to live the life you really want to live; a life that is rich and fulfilling where you feel that you’ve found your passion and are making a difference.  Playing to win is doing that which is uncomfortable.  Playing not to lose is not actually risking much of anything.  You are maintaining a steady course.  Avoiding being hurt; either emotionally, financially, or both is playing not to lose.  You are never really harmed, but you never achieve greatness either.  You remain in your comfort zone and abide by the status quo.  Maybe you decide to stay in the same occupation and career for an entire lifetime because it’s safe.  But this is what I know, you tell yourself.

When we play not to lose, events are filtered through our need to avoid fear and/or failure and fear of rejection.  When we play to win, we interpret events as pushing forward with no guaranteed results—regardless of whether it might put us in jeopardy of failing and/or being rejected.  To play to win, you must get out of your comfort zone and be courageous.  Courage can be defined as driving onward even when the outcome is uncertain and, in many cases, the odds are against you.  We all make bad choices and have to live with the mistakes that we make.  But knowing at least that we have a choice is powerful—and will help us grow and achieve.

The key to maintaining a positive attitude and passion throughout the job search is to believe that the career you are pursuing is the right career for you, and to maintain a sense of control over your efforts.  When you accept complete responsibility for your life, you control your level of achievement and you feel better about yourself.  Your confidence level soars and you feel stronger emotionally, physically, and spiritually.  You are now in control of your own destiny and can achieve levels of success you never before dreamed possible.  Anything that has been learned and achieved by others, within reason, you can do too.  How exciting it is be able to dream your dreams and then actually live them, now!  All you have to do is decide to play to win!

Donald J. Strankowski is founder and President of Ascend Career and Life Strategies, LLC, a career training and consulting firm for businesses, professionals, and executives.  Since 2001, Ascend has helped hundreds of people land a better job, improve their level of performance, change careers or start their own business.  Donald can be contacted at 303-245-7049, via email at [email protected], or on the web at