Beware Rip VanWinkle


Photo by: Ioheasha


Remember the story of Rip VanWinkle? I always thought he slept 100 years, but according to the story, it was “only” 20. While where he found himself wasn’t necessarily his issue, a rotting musket and a foot-long beard might have been. If I could guess, I’d say old Rip must have asked himself, upon waking up, “What happened?” or, “Where am I?” or, “How did I end up like this?” Have you ever found yourself in that state? Asking…

How did we end up here? 

Recently, I was looking at our (Lyn and my) credit card balances. I remember the old days when we wanted to keep it below a thousand dollars…Confession time: it’s been awhile since we saw a month like that…Let’s just say we’ve experienced a bit of what I’ve told people to avoid for years – Lifestyle Creep…It ain’t always as bad as what I saw recently, but again – full disclosure – we’ve spent a boatload of money recently…How did we end up here?

I was meeting with a client not too long ago, and in the middle of the meeting, the “elephant in the room” got named. When it got named, the conversation turned, shall we say, lively. And the consequences of delaying the naming of the elephant could well be grave. While no one was shocked, to everyone’s chagrin, all knew that the topic should have been addressed much sooner: How did we end up here?

OR, family members aren’t speaking to one another. Worse than that, they don’t care if they ever speak again…What become of family birthdays, anniversaries and Christmases? No one sets out on a path to end up there, but How did we end up here?

Did Lyn and I, did the client group, did the family fall asleep for twenty years like Rip VanWinkle? Ol’ Rip didn’t set out to fall asleep for twenty years and neither do we. But sleep happens

More personal disclosure – I like to sleep in the dark – I mean pitch-black dark…In fact, it’s hard for me to fall asleep when there’s any light.

If you don’t want to fall asleep and wake up asking, How did we end up here? 

Keep the light on…

If you don’t want to be in the pitch-black dark with your family, your business or other relationships, keep the light on. How do you keep the light on? Let me suggest two ways.


Don’t kick the can down the road.

 Have the difficult conversations early. Stay after them. If you keep talking in authentic, transparent, and I daresay in courageous ways, you’ll get somewhere. Kick the can down the road to your own peril.

And, secondly:

Don’t assume.

We all know what that stands for…Assumptions lead to conclusions, which lead to always and never statements.

The more you keep the light on, the less you’ll find yourself saying, How did we end up here?

Wishing you all a meaningful Christmas season!



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