Two Important Conversations to Have This Week

If You Could Talk to Your 16-Year-Old Self…

What would they ask you? How would you answer?

  • What’s the biggest difference between friendships in adulthood compared to high school?

  • What’s something that, surprisingly, hasn’t changed much?

  • What’s something that has changed significantly?

  • What gets easier as an adult? What gets harder?

  • What’s something you believed in high school that now seems silly—or even completely wrong?

  • What advice would you give your 16-year-old self?

  • What else would you have asked?

If You Could Talk to Your 60-Year-Old Self…

What would you ask, and how would they answer?

  • What’s the biggest difference between friendships at my age now versus at 60?

  • What’s something that, surprisingly, hasn’t changed much?

  • What’s something that has changed significantly?

  • What gets easier as you get older? What gets harder?

  • What’s something I believe now that will seem silly—or completely wrong—at 60?

  • What advice would you give me?

  • What else would you ask?

Reflecting on conversations with your past and future self helps you gain perspective, clarifying what truly matters and revealing how much can change over time.

It reminds you that while circumstances shift, some feelings and values remain constant. This exercise grounds you in the present, encouraging you to learn from your past while thoughtfully shaping your future.

It’s a powerful way to align your actions today with the person you want to become.

Share this with someone who could use a moment of reflection—you might inspire a conversation they didn’t know they needed.