What Your Future Self Wants You to Know About Life

**Chip Conley** (0:00)
If I really do this exercise well, I will be able to imagine what some of those lessons might be.
Such that I'm living the lesson without having to live the lesson.
The reason we don't like to live lessons is because they're often painful. If I could imagine the lessons, see myself at 80 having dealt with some of those lessons, then maybe I actually don't have to make the mistakes that will lead to that wisdom that comes from the lessons.

**SPEAKER_2** (0:26)
This is The Midlife Chrysalis. Welcome to Wisdom Wednesdays with Chip Conley and Derek Gale, your weekly conversation about thriving in midlife. Together, we explore the questions, insights and practices that help you live this chapter with more purpose, vitality, and joy.

**Derek Gale** (0:43)
Welcome to another Wisdom Wednesday here at The Midlife Chrysalis podcast. My name is Derek Gale. I'm the CEO here at MEA, and I'm with our founder, Mr. Chip Conley. Chip, welcome back.

**Chip Conley** (0:52)
Thank you. Good to be here.

**Derek Gale** (0:54)
So July, here we are.

**Chip Conley** (0:55)
Yeah.

**Derek Gale** (0:56)
Past the halfway point of 2026

**Chip Conley** (0:59)
Yeah. That's amazing.
Yeah. Mid-July, good time.
People get summer wrong. Summer starts around the 21st, 22nd of June, goes till 21st, 22nd of September. But with how schools have changed a little bit such that, like the schools going back to school in early to mid-August, it's like I think of July 15th and this time of year as, like it's still early summer. A lot of people don't think that way, but I do. Yeah.

**Derek Gale** (1:30)
No, I'm with you. I'm with you. But what's always messed, days are getting shorter now.

**Chip Conley** (1:35)
Yeah.

**Derek Gale** (1:35)
That's what I always find amazing is you think this is, no, it's getting shorter. We're on the downswing now.

**Chip Conley** (1:40)
Yeah. No, that's a weird one. Yeah. But one of my least favorite times of year is early December till about December 21st, which is when it just became darker and darker and darker.

**Derek Gale** (1:52)
Yeah.
I live where I live. Sun comes up at 8.3 in the morning and it's gone by 4.3 that time of year. That's rough. But in the summer, we've got sun from 5 a.m. to 10 p.m. All right. We're going to talk about something you've written about recently and that is talking to your elder self. You wrote about imagining a conversation with your future elder self. But as you wrote it, it was not the serene sage on the mountaintop who showed up for you.

**Chip Conley** (2:27)
Well, yeah, and this exercise is, a lot of people do this. And the value in imagining yourself in however many years, you could either say, in this case, I said 80 years old. But in our purpose fellowship, which we talked about recently on a Wisdom Wednesday, we do it 10 years from now. We say like we're creating a 10-year purpose plan. I want you to write a journal entry from 10 years from now in terms of what your life is like. That's a different exercise than what we're about to talk about. But I will say that's still a pretty helpful exercise. A journal entry of who you are, what you're all about, and what your life is like 10 years from now. The exercise of future self, we undervalue, there's a UCLA psychologist whose name I can't remember, Hal Hirschfield. I think that's the name. If that is the name, boy, am I impressed with myself? I pulled that from way in the back of the filing cabinet. We tend to undervalue the future self because we're so focused on the present day or the short term. In fact, Bill Gates said, we overestimate what we'll do in a year, we underestimate what we'll do in 10 years. This idea of future self is interesting.
If you want to, some doctors have shown, especially if they have an unhealthy client, there's software now that can show, you can age yourself 10 years and say, based upon the path you're on right now, or what you look like right now, this is what you're going to look like in 10 years. It's like, oh, okay, I won't lose a few pounds. I'm going to take care of my skin, whatever. The idea of exploring what the future is like is not something we do very much, because we don't like to think about the future and especially later life. Thinking about the future takes you closer to death.
Why would I ever want to spend time dwelling on a time that's closer to death? Now, what I did in this exercise was slightly different than that. Instead of writing a journal entry from 10 years from now, I said, let's imagine that I'm 80 years old, which is 15 years from now. Let's imagine that cancer has not gotten the best of me and that I'm still kicking and I'm being who I am. What would that 80-year-old tell the 65-year-old today?