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Questions for 2023

Questions for 2023

This post is inspired by “Foundations 1, 2, 3, 4” from Krista Tippett (Web | Apple | Spotify)

The predominant narrative of this year has been noticeably marked by catastrophe, dysfunction and antagonising the “other” side – and technology has poured jet fuel on these sentiments. It’s worth acknowledging that many of these stories and experiences are very valid – in war, injustice, and corruption.

And yet. The deepest part of me believes in an alternative way of seeing the narrative of our time: the generative story, which insists that there is an abundance of learning and growth happening right now on dignity, connection, care, and systematic change. And the great rallying call of this century is this: to rise to our highest human capacities, together. And to face into the tough questions, together. (I am massively inspired by Krista Tippet’s work linked above – tune in for more).

The ‘together’ piece is important. Generative change requires us to share our learnings, human vulnerabilities and practices with others. Our impact is limited otherwise, if we are sitting in an ivory tower or in narrow echo chambers full of self-perpetuating biases. This year has highlighted to me the importance of community. I have never felt so connected in an ecosystem of generative change in my life, and I believe it’s a sign of the times (and probably my own growth too). I have been in conversation with activists, content creators, founders, investors, coaches, and leaders in various spheres this year, who are facing into the questions that life is calling us to be with.

And the quality of questions we choose to spend time with really matter. Sometimes, we burn a lot of time and energy chasing answers to questions that aren’t the right ones because we are not ready to live them. Or we sit with questions that can only lead to pessimism, hate and anger. Or we obsess questions that are driven purely by our ego, losing sight of the bigger ecosystem and flow of life that we are part of.

The invitation for you, Millennial Executive readers, is this: to lean into the vast questions of our times. Just as there are callings for life, there are callings for the time we are in. And right now, it feels like there’s a call for Wholeness and Integration. Starting with inside ourselves and the different parts of us, including our shadow sides, and the inner grounding that we can practice to love all parts and heal. And then outwardly in the world that we create and that we interact with, where we are now.

This month’s newsletter is meant to be a guide for this questioning, by offering you some questions to sit with, journal on, and discuss with your communities. These are inspired by Krista Tippett’s podcast series above, as well as my own additions. What better time than now as we start to wind down for the holidays?

  1. How would you start to tell the generative story of the world that you live in, that you can see and touch?
  2. Notice what questions you’re actually living into right now. (Here are some clues: what you’re reading or consuming, what you’re focusing on, what you’re dedicating time to, and who the people are that you are spending time with.) What do you notice? And how could you expand and evolve the questions you’re leaning into?
  3. What do the questions that are most alive in you right now invite you to see or move away from or move towards?
  4. How would you tell the generative story of next year?  What would be your role (the “I”) and who would be part of the story (the “We”)?
  5. Are you part of diverse communities that help you connect into the broader generative ecosystem in expansive ways? How might you expand your communities next year and create stronger connections with friendships, kins and community?
  6. How would you begin to name and work with your personal calling in our current times? Begin to make a list of what in your life is in the category of vocation – your multitudinous callings as a human being. As a leader, friend, colleague, citizen, family, and lover of the world.
  7. What would it look like and feel like for you to walk through 2023 with the possibility of wholeness amidst fracture? Of integration amidst Other-ing? Let your imagination, your heart, your will run wild. Log this however resonates with you – a vision board, a letter, a recording to self. And let it soak in.

Lastly, I would like to say how deeply grateful I am for your continued participation in this newsletter or blog. Thank you for being part of the generative community of leaders leaning into the tough questions of leadership and life in our times. Let’s remember to keep a long-view on time and the broader infinite game at play. Change takes time – but each of our imprints on it still matter. And what an absolute privilege is it to be in positions where we can be part of this? Gratitude is not only called for, but it’s also the only appropriate response to the life and blessings we have been given. Here is a short 6-minute video on gratitude.

With loving kindness,

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