The 3 Toughest Questions You’ll Ever Ask Yourself

First of all, can anyone believe it’s actually the middle of February already? Holy cow.

For me, it’s a year of implementation. I’m focused implementing – in a practical and methodical way – what was set in motion for me last year.

I overheard this great conversation when I was having lunch the other day. Two women “of a certain age” were enjoying lunch together. At the end of their meal, one woman said to the other:

“The older we get, the more we have to change. We can’t get set in our ways. We just can’t.”

So, she’s the Anti-“Can’t Teach An Old Dog New Tricks!”

I was taken by her comment, simply because it was said with such zeal and conviction. And also because that idea – when followed up with practical action – is pretty profound.

So it also got me thinking about my own age and if I’m going to follow that charge myself or whether I’m going to wimp-out and start following the ruts in my own road.


So most of us have heard of a Bucket List.

How about a list of the toughest questions you’ll ever ask yourself? And then be brave enough to actually answer.

After some pondering (with a built-on permission slip to alter my list later in life), here’s my list.


It stings just to see that in writing. Yet I challenge anyone to say that this isn’t a deep-down core issue for almost all of us.

With any luck, effort, grace, and soul-seeking, hopefully this is one of those tough questions that gets asked for a while, and then is answered with a resounding and undeniable “yes!!!”

I just watched the movie The Perks of Being A Wallflower again last night. This quote really resonates with me from that film. In answer to the question:

“Why do people end up with the wrong people in their lives?” The answer [paraphrased]:

“We accept the love we think we deserve.”

What to you think you deserve?


Many times I see people wallowing in a pit of despair because they haven’t asked or answered this tough question.

What are your “by Gods” and deal-breakers — in love, in all relationships, in your work, in politics, in your spiritual life?

You can’t even begin to sort out what you need to support your health and happiness if you don’t even ask yourself this tough question.

If you have no idea how to even begin to sift through what you might list as your 5 core values.



Who Am I? What is my purpose in life? Why am I here?

I feel this is THE most important and the toughest question you’ll ever ask yourself. And you need an answer in order to feel whole and purposeful in your life.

It’s the age-old question that has prompted some of our greatest thinkers, philosophers, artists, writers, and activists to devote themselves to this very question.

Do you have answers to these tough questions?

This can be the year to start digging in and answering these questions about yourself.

If you already know your answers, then it’s always just a good reminder to walk the walk and talk the talk.