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Should I Stay? Should I Go?


And New York, London, Amsterdam, Mumbai, San Francisco, Chicago, Paris…

We have a problem.

Talent turnover.

Like none of us have ever seen before.

Regardless of the market, the industry, or the level of seniority.

Over the past two weeks having flown to five cities in the United States on both coasts, the South and the Midwest and virtually visiting seven countries in Europe, South America, and Asia to advise senior management or speak at team gatherings across a spectrum of industries from finance to consumer-packaged goods to technology, it is clear that the key challenge is no longer tech, data, capital, or business model.

It is people.

Turn over rates of 30%, 40% and 50%.

Hundreds and thousands of open jobs in each company.

The inability to fill roles with significant increases in compensation.

Whether it be two years of re-thinking one’s life post Covid, or the self-immolation of a management class that failed to understand that power has moved to talent and by not talking straight to them is losing them, or the freedom enabled by those lucky to have benefited from the significant rise in capital assets, everyone from someone with two years of experience to extremely wealthy entrepreneurs and leaders are asking…

Should I stay?


Should I go?

Three Filters

Every individual will need to make their own call. 

As someone who had stayed put for 38 years at one place my inherent bias is to stay since 1) the grass may be greener on the other side because it is fertilized by bullshit,  2) because with time one builds trust in a firm and trust is speed and is so critical today and 3) there is nothing as powerful as compounding returns whose benefits are easier to gain by staying and addressing issues at one place versus moving between places.

So, my inclination is wherever you are please first look to stay.

Roots matter.

And often you can find wings at the place you have roots.

Here are three questions you may want to ask yourself to help you decide whether you wish to stay or go.

1.     Freedom: Can you be free to become who you are? Can you have autonomy in your work?

2.     Story: If you shift how does it fit in the story arc of your career? How does it reflect in your legacy if you are senior?

3.     Growth: Can you find ways to grow where you are, or do you have to leave?

You will notice that none of these questions use filters of money, power, fame, or many of the things we worry about.

Not because they do not matter.

But these are not core to how you determine how you spend your one precious life.

Look carefully at many of those who have money, fame and power and you will find amazingly talented people who scripted their story, continuously grew, and struck out freely in new frontiers.

They focus on the ball and not the scoreboard.


One way to define success is to have the freedom to spend time in the way that gives one joy.

Every person has a combination of different elements that bring them joy from adventure to learning to practicing craft to helping others to building wealth to family to passions and hobbies.

This joy is often accompanied by a sense of flow when deeply immersed in doing, a feeling of grace and serenity when feeling as one with all around and often excitement and ecstasy of pleasurable pursuits.

When you do your job does it give you a sense of flow, a sense of being or a sense of excitement at least half the time (hey if your job sucks for a third or less you have a great job …but if there is very little flow, grace or serenity please look to change the situation since no job is worth your life…)

If you find limited freedom in your job does not mean you quit.

Rather go to your manager and insist on crafting a new role that ensures you get the freedom you deserve.

But please do realize you have a job, and you are not being treated at a spa and there is a lot of difficult stuff one must deal with.

Most managers and leaders are terrific once you speak with them as humans.

See if you can get more autonomy for yourself and craft a role more aligned to who you are while staying where you are.

If not leave.


Joan Didion wrote “we tell ourselves stories in order to live”.

We build identity via the narrative of our lives.

As you make you decisions look back from the end to the beginning and ask about your legacy.

In the short term it is to explain why you switched from one assignment to another that sounds strategic and smart.

In the longer run it is something more important.

Your story.

Rupert Murdoch. Bill Gates and many others possibly would give up a lot of their fame and fortune if they could re-write their narrative as they enter their 70th and 90th year.

Only if we could learn what is important before it is too late.

What is the story you want your friends, colleagues, and children to share about you?

It will be the story and not the power, fame, money, or the Instagram post that will endure.

What you do is who you are.

Make sure that where you work, what you work and your career legacy can tell a story that is how you took the road less traveled by, how you told truth to power, how you sang your song and became who you were and where you were sensitive to other people’s thinking but did not live your life to optimize your presence in their minds.

It is your life.

It is your story.

Do not let anybody but you define it.

T.E. Lawrence (Lawrence of Arabia) reminded us “nothing is written”

Till you write it.

Write your life. Write your career.

Be you. (Since as they say everyone else is taken…)

So, see if you can craft the next steps inside your company (every smart firm is far more open to what their talent wants than ever so do give your firm a chance to help you craft your story…but if they do not it is your story and do not ever let anybody, but you write it…)


We all want to grow.

Grow our bank accounts, portfolios, the square feet we live in or own, our power and our reputations.

But in the end, we want to grow ourselves as people.

Our skills. We must be able to build and merchandise the skills for the  future.

Our humanness.

Our potential.

In the end the day we stop growing is when we start dying.

How can we all grow? Learn new skills? Expand our horizons?

Make no mistake most of us are going to have 50-year careers in a world where companies remain in the S&P 500 for less than 15 years, and the half-life of our skills will last less than a decade.

Can you grow your skills?

Can you grow your reputation?

In the end you are responsible for your future. Not your company. Not your HR or Talent Group. But if you can please do stay. But stay because you can become free to be who you are, because you can tell a story and because you can grow.

Too many people end up lost following the wrong star.

It is not fame, money, power or leaving.

It is freedom, story, growth and insisting on these from the places you want to stay at.

If they say no.

Then and only then.


And if you are management struggling to retain talent maybe it’s time to talk freedom, story and growth…

If you are reading this because of a social media post or a forwarded email please join 10,000+ subscribers to receive more writing like this every Sunday for FREE at .

Rishad’s workshops on six different topics (Future, Change, Leadership, Growth, Re-Invention, Selling) are customized by Client and delivered live, virtually, interactively and globally to turbo charge talent in companies across the world. Unleash, upgrade and unfurl your key competitive advantage fast, with force and cost effectively. More at

Rishad Tobaccowala (@rishad) is the author of the bestselling “Restoring the Soul of Business: Staying Human in the Age of Data” published by HarperCollins globally in January 2020. It has been described as an “operating manual” for managing people, teams and careers in the age we live in and The Economist Magazine called it perhaps the best recent book on Stakeholder Capitalism. Business and Strategy named it among the best business books of the year and the best book on Marketing in 2020. Rishad is also a speaker, teacher and advisor who helps people think, feel and see differently about how to grow their companies, their teams and themselves. More at

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