May 29, 2022 6 min read

Two Questions for a Midlife Career Change

Imagine your current career as a rocket ship barreling through space. Many of us, both metaphorically and in reality, are going at warp speed in our careers never considering two basic questions.

Asking these two questions on a regular basis ensures peak performance and minimizes lost opportunities and later regrets.
These can help cut through the noise especially when considering a career change at midlife.

Question 1: Do we know where we are heading?

Usually we are very clear about where something is heading whether it is hailing a cab or taking a trip. However, when it comes to careers, sometimes we tend to go blind to this basic fact.

You might be heading in the right direction within the purview of a career itself – getting promotions, increasing responsibility and so forth. But is it the right career for you to begin with?

Do we like the person we are becoming in the process? Do we like what people 10 years senior to us are doing and is that where we want to be 5-10 years from now? Because if nothing changes, that is exactly where we are headed ourselves.

What prevents us from seeing where we are heading

One major cultural norm that makes us go blind to where we are heading is money. For many of us our careers are a means to an end rather than a calling.

When we started off we didn’t necessarily have the option or the awareness to make a discerning choice. There are others, who along the way figured out that what they were doing for a living was not suited to them or just do not want to do it for the long term.

But over time, especially with well-paid professionals, we forget this tradeoff and the boundary between the means and the end starts blurring.

We continue doing work that we never wanted to do to begin with. We forget that it was supposed to be a short-term tradeoff. The short-term has become the long-term and the original aspiration or vision has either been forgotten or we have become too timid to step out and try something new. [3]

Money is only one form of exchange

Part of the price of becoming a transaction is that we allow our value to be defined by others: an organization, a boss, a recruiter, a partner, a lover.

I become a commodity whose worth rises and falls according to the marketplace. I place my self-esteem in the hands of forces that I cannot control. I am happy when the price rises and feel depressed in periods of recession—and I am literally depressed in times of deflation.

– Peter Block in Answer to How is Yes [1]

We forget that money after all is just one form of value exchange, albeit a very celebrated and visible one in our culture. There are other higher order value exchanges like time, energy and identity. [2]

Consider what you are exchanging in return for money.


This is the one resource that no-one can recreate, store, hack or leverage. All of us come with expiration dates. We only have so much time. Are you ok with spending that time trying to exchange it for money? Time is finite and cannot be replenished. Money is both.

[I]nstead of providing freedom, it imprisons those who covet it; instead of being a possession, it possesses those who hoard it; the only wealth that really matters involves things that money can’t buy.

When asked what surprised him most about humanity, the Dalai Lama answered:
“Man. Because he sacrifices his health in order to make money. Then he sacrifices money to recuperate his health. And then he is so anxious about the future that he does not enjoy the present; the result being that he does not live in the present or the future; he lives as if he is never going to die and then dies having never lived.

– Manfred Kets De Vries in Money, Money, Money [4]


Does your work drain you or energize you? Does it reinvigorate you or does it kill a little bit of you everyday?


Who is the person you are becoming in the process of showing up daily at work? Who is the person you will become 5-10 years from now if you stay on the current path? Is that the person you want to become?

Question 2: Do we like the ride?

To live only for some future goal is shallow. It’s the sides of the mountain which sustain life, not the top. Here’s where things grow.

— Robert Pirsig in Zen & the Art of Motorcycle Maintenance [5]

Do you like the ride, as in what you will be doing on a day to day basis? Regardless of what career we choose there are mundane day to day realities that need to get done.

This is what David Brooks calls “digging the damn ditch” and goes with any career. But often, instead of being just one aspect of our work, ditch digging becomes the whole damn job.

This can be because of a host of reasons. The nature of the role itself might have changed or what is more common is that you might have outgrown the role. There is no element of challenge to it.

But why should we care about the ride? Isn’t the destination that’s more important?

Unlike other scenarios, the ride in this case is our life itself. This is how we are choosing to live our lives on a moment to moment basis.

To live means to experience-through doing, feeling, thinking. Experience takes place in time, so time is the ultimate scarce resource we have.

Over the years, the content of experience will determine the quality of life. Therefore one of the most essential decisions any of us can make is about how one’s time is allocated or invested.

– Mihaly Cziksentmihalyi in Finding Flow [6]

Blinded by outcome focus

We can become so blinded by our focus on outcome, that we do not realize that 99% of the journey is the process, the ride, the journey itself, and not the outcome.

The outcome, the goal, the end-result, is but one aspect of the journey that lasts for the shortest stretch or just one moment of the journey . Majority of the journey is on the path. Do you like that path and the process?

If we do not like the ride aka the process itself, we are far less likely to stick with it in the long term. We are less likely to put in the extra effort to do what it takes to excel. This makes us less likely to stand out in a crowded field.

Authenticity and internal alignment is directly tied to performance, and one common source of inauthenticity is being in the wrong career or the wrong job.

The sooner we realize and leverage our true nature and the kinds of work we are more suited for, the faster we will be able to put in the required work and stand out.

Do you know where your rocket ship is heading? Do you like the ride? What are you going to do different?

Liked this article? Trymy newsletter. It's free and every edition covers essential frameworks on leadership, careers, and organizations in bite-sized form.📚 HBR 100 Best Reads: You also get a curated spreadsheet of the best articles Harvard Business Review has ever published. Spans 70 years, comes complete with categories and short summaries.

Further Reading

Turns out when we are going at warp speed, change is even more difficult. Even once we’ve figured out that something is off after answering the two questions, there is another force that makes it even harder to make any change. It is what Donald Sull calls active inertia. Check out Good Careers Gone Bad - Subtle but Lethal Mistakes in Mid Career to explore this insidious side effect of success.

I quit a successful 20 year engineering career to start my own practice. Most career change advice tends to be lame and superficial. Over the years I collected some key frameworks that helped in making the transition. You can find my entire collection of essential career change frameworks here.

Sources and references

  1. Answer to How is Yes by Peter Block.
  2. Next by Matt Church.
  3. This is true not just for major changes like changing careers but also to minor changes like changing jobs or even taking on a more risky role within the same organization.
  4. Money, Money, Money by Manfred Kets De Vries.
  5. Zen and the Art of Motorcycle Maintenance by Robert Pirsig.
  6. Finding Flow by Mihaly Cziksentmihalyi.
  7. Paul Gauguin went through a major career change midlife and “doing a Gauguin” became a term. Below is an excerpt from the paper Organizational Sleepwalkers by Manfred Kets de Vries:
Some people “do a Gauguin,’’ an expression coined from the name of the artist who gave up his job as a bank clerk and went to a Polynesian island to paint. “Doing a Gauguin’’ means starting something completely new, making a dramatic change in one’s career (Kets de Vries, 1995). The catalyst for this is the feeling that unusual action is needed to get out of a rut. At midlife, it dawns on some people that they have chosen their career for the wrong reasons, for example to please a parent. At this stage in their lives, these people are finally ready to make the jump and do what makes them feel most alive, pursuing activities that they had been interested in for a long time. To experience a sense of renewal, to feel passion once more, they make a complete break from their previous career and find new challenges.

8. Kets De Vries covers this topic in his book Reflections on Leadership and Career Development.

Sheril Mathews
I am an executive/leadership coach. Before LS, I worked for 20 years in corporate America in various technical & leadership roles. Have feedback? You can reach me at
Table of Contents
Great! You’ve successfully signed up.
Welcome back! You've successfully signed in.
You've successfully subscribed to Leading Sapiens.
Your link has expired.
Success! Check your email for magic link to sign-in.
Success! Your billing info has been updated.
Your billing was not updated.