Lisa was a 42 year old female attorney from Stonington who had not practiced law for several years as she had stayed home to raise children. She wanted to get back into the work world but did not want to go back to law. Her strong generalist credentials and her strong general talents should have enabled her to start her job search. But she was frozen. After 20 minutes, I realized that she suffered from “good student disease”. Schools train our students to not make mistakes. Stay in the lines. Progress only after the boxes are checked. Don’t “gamble” by writing an essay outside the prescribed rubric. Lisa dreaded the thought of getting rejected as it seemed to equate with getting something wrong.
Someone who had straight As all her life had made a rejection letter the metaphorical equivalent to an F. In terms of job search, such thinking is the kiss of death. 100 applications for 1 job is sometimes necessary. Lisa’s psychological block had to be addressed before she moved forward.
Matt was a 38 year old engineer from North Haven. He was also the primary breadwinner of a family of four. He absolutely was ready to start his venture. But he had not figured out how the financial piece. 16 years of running businesses and advising entrepreneurs has provided me a wealth of financing and financial knowledge. I sometimes forget that those in salaried careers do not need to develop financial mastery since their financial life is usually clear cut: “I make X. As long as I spend less than X, I’ll be ok.” That’s often the extent that someone thinks about money. Entrepreneurs have to understand cash flow, when to take on debt, what type of debt to avoid, and how to manage with unpredictable income. Fortunately, in Matt’s case, I had some fairly easy solutions to his financial questions. Matt’s practical block had to be addressed before he moved forward.