The October Challenge Continues

Questions to dive deep

Hi Friends,

This is the time of year I always reflect on these questions:

• Who even am I?

• What is my life even about?

• Am I fully expressing myself through my life?

Ya know, the easy, you don’t need to think at all, questions 😝!

Last week I explained that the main reason for this reflection in autumn is because it’s the Jewish holiday season which is designed to give people a time to pause and confront themselves. But there’s another reason, I see autumn as a run-up to the new year. I think of October, November, and December almost as an incubator to think about my life, where I’ve been, where I’m headed, how I want to act in relation to others, and how I might be falling short, WELL before I start planning for the next year.

So this week, some questions asking us to dive deeper into who we are so that we can better decide who we want to be.

I admit, they are a little heavy, but… they are essential questions that if we know the answers, can make our entire lives so much more aligned and rich. And next week I’ll lighten up, humor me, please!

If you’ve been looking for an excuse to dive deep - let it be this newsletter.

Your Week Two of Journaling Prompts

Monday: Understanding where we are

• What is my life about? What matters to me?

• Am I living by what I think matters to me? Not my sister, mom, boss, kid, or anyone external to me? To what degree? Is there anything I need to do to shift into leading the life I most want?

• Talk to your supportability group about matters most to you. If you’re a little lost, think back to last week when you identified your core values. Note: These questions are similar but I ask them twice so we can get really, really clear!

Wednesday: Thinking about our legacy

• What do you think remains when we are gone?

• What impact can we have that outlives us?

• Who is someone no longer with us who had an incredible impact on your life? This person could be related to you or not. I would choose the writer, Nora Ephron, for example. I never met her but the impact of her work, and how she showed up in the world inspires me every day.

• Supportability groups, talk about who has had lasting impact on you. I always find it amazing, in difficult times to remember that the impact of one person can be profound.

Friday: One of my favorite journal prompts of all time

• If I were on my deathbed, what’s the one sentence truth I would say about how I lived my life?

• Do I want to change that one sentence? Good thing I can start today. 

I sorta-kinda apologize for how “heavy” these questions are but also…Idk, we need an excuse to dig deep so that we face the questions that matter the most and live the answers. I’ll lighten things up in the next two weeks, don’t worry!