I was having lunch with a friend the other day and we got to talking about my next career move. I’m at that stage – once again – where I’m thinking about what’s next for me professionally. So, I laid out the three options I’m currently mulling over.

“What do you want me to say?” she asked, when I finished my short speech.

“I want you to tell me which one of those I should pursue!”

She paused and considered my directive for a moment. “What would your 90-year-old self advise you to do?”

What Would Your 90-year-old self Advise You to Do?

It was a great question.

Regret exerts a powerful pull on us in adulthood. And she was basically counselling me not to reach the ripe old age of 90 and ask myself, “What might have been?”

But I felt that she was exhorting me to get in touch with my authentic self. I have a very well developed analytic side to my brain. If it goes unchecked, I can easily spend my life thinking my way through dilemmas. She was basically saying to me: Don’t think: Feel. Ask yourself what you really want right now, not what you ought to want. In other words, no more shoulds.

No More Shoulds

This in turn reminded me of one of my favorite self-help books, about which I’ve evangelized before: Elle Luna’s amazing, The Crossroads of Should and Must. In this book – which is all about uncovering your authentic self – giving up the “shoulds” (what we think we ought to do) for the “musts” (our true passions) – the author has you do a series of exercises designed to elicit your “must.”

One of them which I found particularly effective was to write my own obituary. Actually, to write two of them. The first is how you think your obituary will read when you die and the second is how you’d like it to read. This doesn’t necessarily need to be an exercise about career change, but it’s perfectly designed to explore that realm of life.

Write Your Own Obituary

Try it. It’s excruciatingly painful and yet incredibly elucidating.

If you’re like me, what you’ll discover is that you could end your professional days with a perfectly respectable career doing X, Y or Z. Perhaps you’re on a few boards and maybe you’ve even won some accolades.

But while your “likely” obituary might recount a professional journey you won’t be ashamed of, that doesn’t mean that it’s really “you.” And if that’s the case, you might end up closing out your days feeling cheated.

I, for one, don’t want that to happen to me.

Which is why that lunch was a great wake up call. It encouraged me to check back in with myself about what I really want to get out of the second half of life. I went back to those duelling obituaries, re-read them, and realized that I was still in danger of having the “wrong obituary” if I wasn’t incredibly mindful about how I approach this whole process of career change.

I’ll let you know how I get on.

What dreams do you have for the coming decades? Have you ever tried to write your own obituary? What advice would you think your 90-year-old self would give to you? Please share in the comments.