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The Career Reinvention Question You Need to Ask

If you’re eager to switch fields in midlife, follow the 'What?' with 'Why?'

By Nancy Collamer

As a career coach who helps clients switch fields, I’m always asking lots of questions. Things like: What types of people do you like to work with? What are your strongest skills? What did you love to do as a child?

The Problem With Asking 'What?'

The answers to those queries provide insights into the key factors – like skills, interests and values – that are important to consider when choosing a second act. But these types of “what” questions, while useful, are often very limiting.

(MORE: The Key to a Successful Career Shift: Asking for Help)

To really assist people who want to reinvent their careers, I always dig deeper and follow up the “What?” by asking “Why?”

You should ask yourself the “Why” questions too if you’re contemplating going into a new field in midlife. For example:

  • You like to facilitate meetings. Why?
  • You enjoy working with the elderly. Why?
  • You love reading historical fiction. Why?

Why You Should Ask Yourself 'Why?'

Why is asking “Why?” so important?

Simon Sinek, author of the bestselling book Start With Why: How Great Leaders Inspire Everyone to Take Action, says every career functions on three levels: What you do, how you do it and why you do it.

Everyone knows what they do and some people know how they do it but very few people understand why they do it.

When you understand why you do what you do – and why you like what you like – it then becomes much easier to target potential careers that align with your personality, motivations and interests.

How Barbies Inspired a Career Shift

Let me share a real-life coaching case that demonstrates the value of asking “Why?”

(MORE: A Midlife Career Shift Against All Odds)

I recently met with a client who is employed as a data manager and asked her to tell me about her favorite childhood activities. When she recalled loving to play with her Barbie dolls, I asked: “Why did you enjoy doing that?”

At first she just laughed, clearly a bit uncomfortable by my line of questioning. But upon reflection, she said, “You know, I’m embarrassed to admit this, but I would concoct elaborate make-believe scenarios between my Barbie dolls. I’d pretend they were having a fight or going to a party together or discussing their crush on Ken. Even though I knew they weren’t real, I loved thinking about what they would have acted like if they were.”

It was a revealing insight.

While she could have said she loved Barbie’s sparkly clothes, her dream house or her cool pink car, she didn’t. The “Why” behind my client’s Barbie fascination revolved around her dolls’ pretend conversations.

Interestingly, that same focus on interpersonal relationships showed up when we discussed other parts of her life – her favorite jobs, volunteer work teaching adults English as a second language and love of reading biographies. Her “Why” always centered on people and relationships.

After recognizing this pattern, she is now in the process of exploring opportunities in such fields as teaching and social work, where her strong people skills are likely to be highly valued.


Asking 'Why?' Helped Him Make Retirement Plans

Another client, currently working in information technology, told me he loved learning about wines. When I asked why, he said that although he likes drinking wine, what really appealed to him was how the hobby brought back memories of the years he spent visiting his grandparent’s farm.

We talked some more and he realized that he missed spending time outdoors. That discovery prompted him to consider investigating second-act careers that will let him work outside when he semi-retires in a few years.

(MORE: Career Shift: ‘You’re Never Too Old’ Success Stories)

I’ve asked clients “Why?” hundreds of times with equally successful results.

A Career Coach’s Tip for Your Second Act

So my advice to you the next time you’re contemplating making a career change, remember to ask yourself: “Why?” in addition to “What?”

Instead of “What jobs did I enjoy the most?” change the question to: “What jobs did I enjoy the most and why?”

Instead of “What were my greatest successes at work?” ask “What were my greatest successes at work and why?”

Instead of “What type of job should I look for?” ask “What type of job should I look for and why am I looking to make a change?”

By doing so, you’ll discover fascinating insights into your work-related motivations, values and interests.

Once you know what is truly most important to you, it will be far easier to choose a second-act career you’ll love.

And then, the only question you’ll need to ask yourself is: “Why didn’t I do this sooner?”

Photograph of Nancy Collamer
Nancy Collamer, M.S., is a semi-retirement coach, speaker and author of Second-Act Careers: 50+ Ways to Profit From Your Passions During Semi-Retirement. You can now download her free workbook called 25 Ways to Help You Identify Your Ideal Second Act on her website at (and you'll also receive her free bi-monthly newsletter). Read More
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