Mentoring for Risky Career Choices

I received a call on the weekend from someone I did not first recognise. The happy caller wanted to thank me for my mentoring him twenty years ago. At that time, he was?a freshly qualified post-grad, desiring to forgo the easy option of an assured job with Big 4 to risk chasing an unavailable role as an equity analyst. I was a busy Lazard M&A banker with adventure on my mind.

These days I work with my mentee through an evaluation of their own temperament, strengths, dreams, fears and dislikes, pros and cons of taking one of the competing choices and scenarios of success and mediocrity in each one, before either arriving at a unanimous decision or differing and showing to them what appeared to be a natural direction for them.

In general, I continue to be biased in favour of?high reward high risk choices their family and well-wishers would question.?I recall instances where I supported an IT engineer toying with the idea of becoming a classical vocalist, a successful accounting professional about to become a financial journalist, and an MBA with a banking job offer dropping that to become a diamond trader at one fourth the salary. Recently a mid-level MNC telecom executive on management fast track asked for my opinion about moving to a smaller FMCG company with the challenge to prove herself as a newcomer; and my obvious view was that the risk of a new, nimble environment was qualitatively better than the risk of a stagnating industry.

As I understood from the caller, in his case, I had strongly supported his aspiration.

Fast forward 20 years and he is a confident, successful buy side analyst and investor. He spoke about the multi-baggers (a stock that grows multiple times in value, usually over a long run) he had identified in his career. I joked that he was the multi-bagger I had identified!

Young risk takers seeking mentors are, in my experience, secretly looking for validation of their unconventional ideas and hazy plans from people they see as successful and wise. It’s a challenge for both the parties involved.

The first challenge for the young ones is that only a few family members usually support their crazy career options or start-up ideas because the family are emotionally invested in the safety and well-being of the young ones, which usually means a well-respected job and an assured and growing income stream. Family are rarely good mentors, yet they are the best providers of emotional and financial support to an adventurous kid.

The next challenge is that the so called successful and wise people who the young ones approach are boomers, yours truly included. Most of us mentors grew in our careers or business in the BC era i.e. ‘before cloud’ era. We may be living in the cloud era but we are not truly experienced in the early entrepreneurial challenges it entails.?

Thirdly, people who are successful and relatively young are time-starved, who can only be listened to on YouTube videos and rare institutional live talks. They can go on about their struggles and eventual successes and expert opinions, and all that may be very inspirational. However, their stories may not have much relevance to the circumstances and challenges of the mentees, who need specific insights, repeat Q&A sessions and most of all customised mentoring hours and ears.

Lastly, from a mentor’s point of view, mentoring could only be described as successful if the mentee felt that it worked. ?

So you know why I am happy!

Chetan