Good morning from Mexico City. It’s Wednesday and Wednesdays are for questions. The questions that are coming up for me today are from Chip Conley. If you’ve never heard of Chip Conley, look him up. He’s a super cool guy. He’s very successful, and he’s extraordinarily wise. You will absolutely want to sign up for Wisdom Well, his daily blog. It’s short, punchy, pithy –  whatever you call it –  and very thought provoking. I just love it.

Anyway, I’m looking over some of his work because I’m going to be attending the Modern Elder Academy (MEA) next week and I stumbled upon these two questions that I thought I would share with you. Chip talks about what he calls anticipated regret. He says anticipated regret is a form of wisdom, and I never really understood quite what he meant until I read these questions.

This is the first one. What do you know now that you wish you had known ten years ago? Again, what do you know now that you wish you had known ten years ago? That’s something we’ve heard many times, but here’s part two. And here’s where the anticipated regret as wisdom plays in in 10 years. What will you regret if you don’t learn it or do it now? Let me say that again in 10 years What will you regret if you don’t learn it or do it now. This resonated with me on so many levels but in particular right now because I am in the beginning of my journey. I feel uncomfortable as I mentioned on Monday. I’m sort of asking myself what the hell did I do. This reminded me that part of the reason I decided to step outside of my comfort zone and test myself and force a little life quake (as Chip calls them) is because I think it’s something that I’ll regret if I don’t do it. I will admit there is a little part of me that wishes I had more of a plan, but even that was intentional. I want to feel my way forward. I want to see how I feel. At the same time, this kind of lack of clarity about where I’m going over the next months is at times a little bit disconcerting. But I made the choice to leave for five months because even without having read this question, I knew it was something that I would regret.

Another thing I’m holding in my heart is this idea – it’s something I think I spoke about in a recent episode –  it’s taking what’s dormant or festering and making it conscious, intentional and deliberate. That’s what leaving New York for me is about. Going outside of my comfort zone and exploring this new sense of freedom t- his whisper that I’ve been hearing in my heart for some time – is about. And quite frankly, I don’t want to live with the regret of not having answered that call. So while it’s uncomfortable, it’s something that I know I need to do.

I think we all have these things. It doesn’t have to be leaving home for five months. It can be as simple as taking a trip with a family member or one of your children. It can be joining some sort of team. It can be taking up the guitar again, taking singing lessons, or sitting down to finally start to write that book that you’re carrying in your head. I don’t know. I can’t know what it is for you, but I know when you think about anticipated regret, there must be something you might want to think about again.

So I’ll close with the two questions again. What do you know now that you wish you had known ten years ago? And in 10 years, what will you regret if you don’t learn it or do it now?

I’ll leave you with that today. Until next time, from my heart to yours.