M was a self-made millionaire. He made his first ‘pot of gold’ in his early thirties through sheer grit and drive. Four years ago, he made a huge and risky investment in real estate which flopped and made him a virtual bankrupt. He had to sell his business and borrow money to settle his debts.

W was a senior executive who lost her job recently from a restructuring exercise at the senior management level. During the discussion of her dismissal, she was told that she was ‘a victim of collateral damage’ from the forced departure of the CEO, as she was one of his key lieutenants. She had to leave the company within a week.

Z was the young scion of a successful entrepreneur. He could have joined his family business after graduation. Yet, he chose to make it out on his own and joined a multinational organization as a management trainee. Six months later, he was informed that he did not clear his probation and advised to consider alternative career tracks within the company.


M, W and Z are all in different career pit holes.

Yet, they faced the same psychological trauma of defeat and loss.

A business failure, job loss or demotion is often more grave than a financial loss. It can also be a loss of self-esteem and ultimately self-identity as a productive member of society.

In our climb out of career pit holes, it doesn’t help at times when our close friends and professional relationships become detrimental by questioning the details of our losses.

The worst comment that anyone could say to an individual who had just lost a business or job would be: ‘You should have seen it coming’.

In hindsight, anyone could claim to be the foreteller of another’s derailment.


For those in career pit holes, a pragmatic approach would be to ask:

  • What was the value that I discovered about myself?
  • What did the experience teach me that will be valuable in a different context:
  • What was right about this episode for me?

For M the entrepreneur, the experience taught him the pitfall of unbridled risks. His value was capacity for planning and disciplined business growth.

For W the high-flying executive, it was building a personal leadership brand that distinguished her as a practice leader in the industry.

For Z in his early career, he discovered an endearing trait of persuading others and started a new job in sales and marketing. His passion was doing what he liked rather than to prove his worth to his parents.

The three of them now fully appreciate the need to ask the right questions when they encounter friends who lost jobs or businesses.

And it’s not – I told you so.