I met Heidi Lumpkin when she was my career coach several years ago. She’s skilled at asking questions that delve into your motives and can help you devise practical plans for action. I chose Heidi because unlike other coaches who said they could help me achieve my goals – Heidi said she could help me discover what my real goals are.

Heidi has two questions she likes to ask when coaching anyone – whether she’s been hired by business clients to help their staff develop and grow, or by individuals whose circumstances have them in transition looking for a new job or plotting their next move.

These are the two questions that according to Heidi, “…elicit the ‘Uhhh…’” response more often than any other.

The first question is:

“When do you want to retire?”

After a fumbling response, the follow-up question usually has an even bigger pause, plus a more vague answer. That second question is:

“How are you going to get there?”

She says that usually the answer has something to do with “hope.”

I suggested to Heidi that perhaps there should be a third question:

“And then what will you do?”

That’s been the premise of my ‘phased retirement’ writing. Determine and practice “how you get there?” alongside “what will you do?” This gives you months or years of planned preparation for retirement while discovering likes and dislikes and getting a taste of how your time will be spent.

I’d submit that if you can answer those questions in reverse order, and you know WHAT you’ll do and HOW you’ll get there – the WHEN becomes less important.