Image by David Rojkowski using Leica iPhone de Lux.

The most important expiration dates are not those on food, subscriptions, insurance policies or medicine.

These dates are known.

Its the expiration dates that are unknown that matter the most.

Image by Selmo Kim

Career Expiration.

‘Every career has a midnight hour. The smart people leave at five to twelve.’

This piece of advice by my friend Sanjay Khosla who ran many large companies over his career really resonated.

Regardless of how good we are, how senior a role we inhabit or how irreplaceable one thinks one is, every career comes to an end.

All is well and then suddenly we find ourselves at midnight hour and the carriage of a career turns into a pumpkin.

The key is to leave before the midnight hour.

This ensures that one avoids being shown the door or shuffled into a reduced role .

The difference between early and late is significant because those who over stay often turn bitter or lose the community or connection that come from colleagues because one has left under a cloud.

These midnight hours occur not just at the end of a career but all through a career.

And they can be felt.

Be particularly wary when one or some combination of the following changes happen:

a) a change in management, b) an acquisition or take-over, c) a sudden change in financial results or d) a shift in technology which creates a strategic review.

When one instinctively feels a change in the force one must pay a lot of attention and ask some combination of the following four questions:

a) How to adapt to the new management?

b) How to adjust to the new culture and power shifts of an acquisition or sale?

c) How to re-think ones skills, approaches and role in the shifts that follow a change in financial result?

d) How to reinvent, learn and change to align with new technology?

If one does not adapt or re-invent or one feels that one cannot work under the new changes then be prepared to find one on the wrong side of the midnight hour and it is better to exit with grace.

Companies do not adapt to employees.

Employees have to adapt to the new realities.

If one is not willing to adapt then get ready to walk.

There is one other time when the midnight hour occurs and this is when one stops growing in a job.

The day one stops growing it means one’s career has started dying and the midnight hour has arrived.

Image by Pepitobobito using MidJourney

Financial Expiration.

The underlying basis of much financial planning is based on three unknown expirations:

a) When will you retire?

This number is shifting to much older for most people either because we are living longer, or in some countries pension payments are being pushed out to later years, or because the cost of living has risen forcing one to work longer.

b) When will you stop earning income?

One can continue to make an income after one leaves a full time job though it may be smaller and more variable till one day it stops. Many financial models fail to take this into account.

c) When will you die?

This number is the big unknown but in most countries it is later and later and something that people have not thought about is how a combination of AI and Biotechnology could significantly increase life expectancy due to breakthroughs in medicine.

It is fascinating to understand how many retirement calculations are based on assumptions that may not make sense. For instance the famous 4% rule that one can draw down four percent of ones assets and not run out of money is based on retiring at 65, having no income and living to 95. Even the person who came up with model believes the draw down is too low.

Similarly annuities which pay a fixed sum for the rest of one’s life is a bet by you that you will outlive the calculations of the actuaries at the Insurance companies. And since they have not factored in the impact of AI and Biotech yet it might be a good bet!

Image by Yiplingli42 using Midjourney.

Life Expiration.

“The Meaning of Life is that it Ends”

Franz Kafka’s quote above explains why living forever even it it was possible might make life less special since if there was no loss, no last things, no ticking clock, would any day, anything or any moment be particularly special?

If one knew how many years one had left would we not live very differently than we do today?

Anyone given a bad health diagnosis usually changes the way they live because they become particularly aware of time.

But most of us can determine the time we have left if we want to.

Globally life expectancy is 73 years and in the US it is 78 years.

So assume 75 years of healthy life.

Subtract your age from 75 and multiply it by 365 days and that is what is left.

Most people are surprised how few they are.

Someone at 55 has just over 7000 days left.

At 65 its a little over 3500…

Keep that in mind next time someone does not take your time seriously.


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Rishad Tobaccowala leverages forty years of global experience across dozens of industries to help leaders and companies thrive in transformative times.

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