Jumping from Planes and Ladders: Midlife Career Change

By Dr Rob Handelman, Psy.D.

“Midlife is when you reach the top of the ladder and find that it was against the wrong wall.” Joseph Campbell

If this quote rings at all true, and if this “wall” happens to refer to your work life, perhaps it’s time for some exploration, clarification, and/or action.

Perhaps you’ve been thinking about this for a while, or perhaps there’s lately been a growing sense of dissatisfaction, boredom, disconnectedness, or just plain misery.

A little morbidity: Bronnie Ware, a palliative nurse in Australia a few years ago informally asked some of her dying clients what their top regrets are.  She wrote a book called The Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing (2012).

  1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.

At midlife, we are more acutely aware of time passing, and there can be a pressing sense of needing to fill the remaining time with more good, important stuff.  Stuff that matters.

And if we start to think about making a change, even in meaningful directions, we can feel more fear: of less security or stability, not enough money for retirement or college, disapproval, giving up comforts, etc.  Perhaps there are added stresses: illness, aging parents, growing children.  At worst, we can feel completely stuck, and have thoughts of hopelessness and despair, which can be paralyzing in terms of making choices and taking action.

On the other hand, maturity also brings with it some perks: “wisdom”.   We know more about our strengths and weaknesses, we know more about the value of time and energy, we have more perspective.  We really get the life is short thing.  We may also know more about what motivates and inspires us. We know more about our limits, of stress, physical limitations, patience, resilience.  Maybe we’ve learned about courage.

And the difference between our needs and wants.


So let’s say that a life true to yourself means that you have always wanted to skydive.  You decide to take the plunge. Hah. You do your research, reputable companies, best parachutes, injury statistics….You’ve minimized risk to the extent possible.

And yet, when it’s time to jump from that plane, all that planning doesn’t make uncertainty and fear go away.  You don’t know you won’t get killed. You don’t know it won’t be too terrifying.  It’s a risk.  We take risks in the service of vitality.  We are willing.  This is Courage.

This is true of career change too.  We can intentionally research possibilities, we can do the math, we can clarify our own values. And at every turn, we will have difficult thoughts and feelings, designed to keep us safe and comfortable. Thoughts and feelings about the future, the past, our identities, our self-esteem.  The mind wants certainty and resolution, and it wants it now.  And it can’t have it now.  It won’t let up.  And it can be very difficult to distinguish between helpful and unhelpful thoughts.   Confusion is the norm.

When starting to explore career change at this time of life:

  •  Explore what makes you feel most engaged at work: connection, opportunities for growth, support, encouragement…
  •  Explore what money is about for you: comfort, luxury, stability, power…and how it contributes to your sense of purpose and meaning.
  •  Explore your “what ifs”: “What if it isn’t the “right” fit, what if I’m terrible at it, what if I fail miserably…”
  •  Explore your “yeah buts”: “Yeah but, I need this amount of money; I’m too old; I’ve never done…; I’m not good at…I’m not a risk taker…”

Check to see if the “what ifs” and “yeah buts” are useful – are they just there to protect you or keep you comfortable in the short term?  Are they in line with what’s important for you in the long term?

Ultimately, we can only know if your skydive was worth it afterwards.   In the meantime, can you be willing to take a step down the ladder, a rung or two or three at a time, if your sense of vitality and engagement in work is worth the jump?


Career Change, Developing Coaches - ACT Training, Getting Unstuck coaching

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