Jeff Saperstein

An important step in career planning is to answer two simple, but really difficult questions: What do you want to accomplish? What is hindering you from achieving it?

Sure, it is easy to say, “I want a promotion, more money, freedom, prestige, security, etc.”. However, these answers may skirt the real issues.

What we say we want may be conditioned by what we believe others expect or have determined for us—what Abraham Maslow termed externally generated self-esteem. What hinders us are: limiting beliefs of what is possible, conditioned negative attitudes, false interpretations, and a hidden demon that we are not good enough, smart enough, deserving enough, or put together enough to succeed.

We could alleviate a lot of stress and be far more efficient, effective and happy if we could align our values—desire for autonomy, mastery, purpose, progress, sharing collaboratively with others, intimacy with loved ones, feeling of belonging in community—with our activities.

What does fear that hinders sound like and how could it be reframed for success?

Jane is a 50-year old woman who has graduated from prestigious schools with degrees in engineering. She worked in large tech firms and then spun off as a Consultant in Silicon Valley. She has gone from gig to gig trying to help other start-ups succeed and has tried to start up her own business.

When asked what she wants to achieve, Jane says she wants to build a $30 million software start-up. She has neither headed a company nor brought a start-up to exit, but she has the knowledge of how she has seen others do it. 

Her father gave her love if she was smart, did things successfully, and shined. He disdained her if she did not excel. This was indeed the source of her demon. Facing it, she could see that her expectations to build a $30 million start-up were a result of conditioning. She admits that she is disappointed with herself for what she is now doing in her career, and fears she is not going to be who she imagined she would be. 

As we went deeper into what she really wants, she articulated that she would really like to help enable the next generation of leaders in software services development. Her desire is to be in an environment where she is valued and trusted, where her creativity, curiosity, collaborative leadership can lead to great solutions executed with others. Her real strength is in how to guide others in assigned roles and to direct a team.

Finding her true aspiration, Jane can begin to build realistic goals and a plan to achieve what she really wants.

Amy had been a professional fund-raiser for 16 years. She has been out of work for a couple of years and is raising baby twins. She wants to go back to work when her kids can be enrolled in pre-school. She says she hates fund-raising.  When asked what she wants to do, she has many ideas of what might be possible, but has been stymied to make a choice and move forward.

She says that the world pigeon-holes her into fund raising; everyone Amy knows in her business community just thinks she can only raise money. She is stuck. We begin to identify transferrable skill sets that enable Amy to build on her organizational and fund development experience, but get her out of a role she no longer wants to play. Amy is passionate about certain global issues and she can focus her job search to an organization that she can bring value to, but also enable her to have flexible time to raise her children.  She has overcome her belief that no one will want to hire her if she is not committed to full-time, all the time availability. Amy is now looking for flexible scheduling as one of her goals so she can attend to her family while transitioning to a different career path.

 
Sometimes life issues can become the focus for change.  

John is a highly motivated, disciplined professional. He has a degree in Psychology and is now getting an MBA and certification in coaching so he can broaden his expertise for career development. He is right on track. However, when evaluating his alignment of values with his activities, John admits that he is not happy with his personal life. He wants to talk about this. He reveals that he has had two very uncomfortable relationships, each ending in embarrassment and pain. John has withdrawn and not dated anyone in eight years.

My instinct as a twice-married man, who has dated in mid-life, is to give advice on women, dating sites, and approaches to get into a relationship. However, my instinct to give advice and information is not what John needs. So I probe what hinders John from initiating contact or responding to women he may be attracted to. John admits that he is afraid of rejection, appearing to be sleazy if he would be making advances to women, and anxious about what could go wrong if he makes a bad choice.

John has a scientific mind. So I took an intuitive leap and asked him on a scale of 1-10, with 10 being the worst and 1 being no big deal, how badly would he feel if he approached and then was rejected by a woman. He said about an 8. Ok, supposing there was a fantastic lady who could be a wonderful companion to you for the rest of your life.  Use the same scale and with 1 being it would not matter and 10 being it would be fantastic. John said it would be off the scale wonderful! So I asked how would he feel about approaching women with the attitude that the one “wonderful” would clearly outweigh any number of rejections. As prosaic as this approach might sound, it was a breakthrough for John. We agreed on a plan of action where he would ask women whom he was attracted to coffee with the intention of friendship so he would not feel sleazy, yet get to meet prospects who might be that wonderful person.

So what does life-changing fearlessness look like?

Bill had been a seeker as a young man, had lived in an Ashram, and followed the 60’s hippie lifestyle. Eventually, he worked his way into human resources and rose to a high level position as the lead career coach for a Fortune 100 company. He established a reputation for excellence in executive coaching and is considered one of the premier coaches in the field, assigning other coaches to individuals in the company.

In his mid-50’s Bill realized he was getting diminished satisfaction, and while receiving external confirmation that he was at the top of his game, he recognized that he was no longer doing what he really aspired to do.

Today at 62 Bill is transitioning out of executive coaching and devoting his time to being a Hospice worker. He lives simply, on a mountaintop with his dog, and comforts those who are about to depart from the world. Bill told me he almost feels guilty for how good he feels holding the hand of an unconscious elderly woman with the knowledge that this loving kindness will be the last experience she will have on earth.