Are You a Winner Who Cannot Lose?

I was struck by the “Editor’s Letter” in February’s Vanity Fair. Graydon Carter wrote about the temperaments and actions of two modern day presidents. It made me think.

According to Carter when Bill Clinton plays golf he takes a high number of mulligans and often hits two balls for every shot, accepting the best lie as his own. He supposedly has a generous view of the line in tennis. George W is known for refusing to lose. When it was clear the game was not going his way he’d insist on changing a best of two tennis matches to best of three. As a child he had to be physically taken off the golf course because of his cursing and acting out when the shots weren’t going his way. Do any of us really change? Want to read the entire piece? Go to Vanity Fair.

What do you do when it is clear you are not going to win or get what you want? Are you able to cut your losses early, re-group and address the challenge from another angle? Do you accept defeat gracefully? Can you stand-up and face the consequences of your actions or do you expect others to tolerate your missteps and abide by your rule changes? Do you tolerate rule breakers? Are you a rule breaker?

Many of my clients struggle with the definition of winning. The blueprint that served them well in their teens and twenties (do well in school, get into a great college, stay out of trouble, get a good job with an excellent firm, and don’t get any one else in trouble) seems faded. The signature in the corner of the document is their parent’s, not theirs. It ends with reaching a middle level of success and now they are not so sure what to do. For many there are almost too many options, others an inability to see any.

In our coaching sessions clients and I define success, create a vision and set goals and objectives for achievement. When they get stuck we play our scenarios, do a risk/benefit analysis and take reasonable chances. For many people bouncing ideas off an objective person, who has their best interests in mind, serves as a catalyst for ideas and actions. Sound like something you might benefit from? Consider hiring me as your coach.

Your challenge for the week

  1. Observe how you win and how you behave when things do not go as planned. What do you expect from yourself and others in these situations?
  2. Can you think of a time when what looked like a defeat actually was a win? How did that happen? Miscalculation? Complicating circumstances? Greed?
  3. What is your blueprint? Is it working for you? Sure it is yours (check the signature).

Jane Cranston is an executive coach, career coach and “The Job Search Expert” based in New York City. She shares with success driven executives and professionals techniques, skills and goal setting strategies that advance their careers, increase people management skills and assists them in career change or job search. Receive Jane’s free "Competitive Edge Report" and the free audio download “Creating a Career Strategy” by visiting

About the Author

Jane Cranston - Executive Coach NY (New York)Executive and career coach, “The Job Search Expert,” Jane Cranston understands the challenges and opportunities in the workplace. She integrates years of experience as an accomplished senior executive with global brand name companies, with the lessons learned from opening three successful businesses, and then applies her education and coach training. This sophisticated mix affords her clients her unique perspective, business sensibility, and entrepreneurial spirit.

Jane is the founder and Managing Director of ExecutiveCoachNY, an executive and career coaching business based in New York City with clients nationwide. She coaches success-driven executives and managers to develop a career strategy that accelerates advancement, increases compensation, enhances people-management skills as well as gets the competitive edge in all business activities.

Coaching with Jane is dynamic, structured, forward-focused as well as fun and inspirational. Working with clients in fields such as finance, technology, media and entertainment, real estate, and the law, she assists them in recognizing and achieving their full potential at work and in their personal lives.

Clients claim coaching with Jane has “changed my career focus,” “helped me better understand how to motivate my staff,” “given me ideas that have increased my income by $100,000s,” and “made me realize what is my part and what isn’t,” and claim coaching is “the best thing you could do for yourself.”

Jane’s soon to be published “Great Job Tough Times” is a step-by-step job search system designed to assist managers and executives looking for employment, or contemplating leaving their current positions, with their resume writing, interviewing skills, networking techniques, and negotiating need to get the right job fast.

Jane Cranston is frequently seen on CNN’s “Your Money” and quoted in nationally syndicated newspapers, magazines, as well as Internet article sites and virtual programs. She authors the free, twice monthly, “Competitive Edge Report.” Learn more on her website


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