Try, fail and try again

I have been starting and stopping different education programs and jobs for many years, and it is exhausting. I know the reasons why I am unsettled, but don’t know what direction to take next. I am in my 40s and feel panicked and embarrassed for not having started a career. I work part time, I volunteer and I am responsible. I’ve seen counselors to deal with my abusive childhood, and they were somewhat helpful, but not for career issues. I have also seen career counselors, but they didn’t help much, either. I feel stuck and hopeless.

Who told you that you had to have a career? Or that it is necessary to complete everything you start? Carrying someone else’s expectation for your life is exhausting. If someone you admire, like your mother, father or high-school history teacher, suggested a particular path, you might walk that road in an attempt to gain approval. Along the way, your own dream for a delicious life is trampled underfoot. This is one of the most common ways to kill ambition.

In his book, Turning Pro: Tap Your Inner Power and Create Your Life’s Work, Steven Pressfield writes: “Ambition, I have come to believe, is the most primal and sacred fundament of our being. To feel ambition and to act upon it is to embrace the unique calling of our souls.” Pressfield also writes brilliantly about shadow careers, the work we accept to avoid facing our true calling. He notes that the shadow career is a metaphor for our real work but is risk-free. “If we fail at a shadow career, the consequences are meaningless to us,” he writes. The high-school English teacher who yearns to be a novelist but focuses on getting her students published, or the cover-band musician who gets stoned instead of writing original music are examples of people entrenched in shadow careers.

So, if you’re unhappy, investigate what your current life is a metaphor for. The answer reveals your true calling. Once you connect your career with the compass in your heart, you will be motivated to follow through on education plans and training. That’s because you will have awakened to a special life purpose that only you can fulfill. That doesn’t mean your path will be without obstacles. Resistance, in the guise of a fear of success, will continue to interject itself (although it grows weaker when you don’t give in to it). Remember this: Fear of success is just a fancy way of admitting a fear of being authentic. Becoming who we are meant to be requires that we swim against the tide of other people’s opinions. It feels so unnatural at first, that we will often fail. Failure provides the opportunity to improve skills in problem-solving, in demolishing resistance and in accepting rejection as a normal human experience.

The most innovative new education programs, like Draper University in San Mateo, Calif., encourage failure. At Draper, students in the entrepreneurial-training program accumulate points “for heroic acts and spectacular failures.” Founder Tim Draper, a venture capitalist, points out that his program is the antithesis of a traditional school where, “you get an A only if you make no mistakes.” In a recent interview in the San Francisco Chronicle, Draper said, “The world needs more heroes who are willing to break out of those constraints.”

How would your life be different if you had been encouraged to explore the height and width of your creative, entrepreneurial self, and to value your failures as courageous attempts to reach success? Try that new mindset now and thrive. As the writer George Eliot once wrote: “It’s never too late to be who you might have been.”