Looking Back to Look Forward.

May 20, 2023

Looking Back to Look Forward.

May 29, 2023

I’d heard about the Modern Elder Academy (MEA) for a few years. A wisdom school for midlife transitions? Sign me up. I’m a few years out from 50 and feeling a deep desire to make the second half of life one for the books.

Not to sound dramatic, but for all my external achievement, I sleep-walked through early adulthood. I was on the success train to…I don’t even know where. So I jumped at the chance to take the time to pause and reflect on what this next chapter would look like.

To my surprise, my biggest takeaway wasn’t about the next chapter at all – but about how someone transitions from one chapter to the next. A core part of MEA’s offering is acknowledging and appreciating that we don’t have a rite of passage for midlife. When we leave home, get married or start a family, we’re doing so in the company of others. Not so for midlife. We walk that path alone. So a group of us aging from 35 all the way up to 75 made our way down to Baja to learn–and share–about our own midlife transition.

MEA divides transitions into three stages–The End, The Messy Middle and The New Beginning. The End is about taking stock with reflections and rituals. The Messy Middle is about curiosity, asking questions to explore what’s next. And The New Beginning is about a new purpose more aligned to who you are deep down. When I thought about past transitions in my life, I couldn’t see any of these stages. I’d gone through a lot of big changes in my life, more than most people, and couldn’t remember ever taking stock, exploring my curiosity, or aligning to some new purpose.

My response to change was to always look forward, never behind you. I learned from MEA co-founder Jeff Hamaoui that this was a transitional toolkit I learned as a kid, watching my parents go through all the changes in our lives–some chosen and some not. Unless you take an inventory of how you learned about transitions in childhood, you’re probably carrying those outdated tools with you into midlife. Think about your parents getting divorced when you were young or changing schools more than once. How conscious were you of those transitions? What tools did you use to cope and manage the transition, if any?

After Iraq invaded Kuwait, my family was forced to move to the US. Kuwait had been our home for several years. I was a boy there. We couldn’t go back to the country–schools were shut down, fires still burned in the oil fields and our community had dispersed to other countries. My family and I didn’t take stock of what happened. We didn’t mark the end of a chapter. And we didn’t explore what was possible in our new world. We didn’t create a new beginning, we just moved on.

It dawned on me that so many of my transitions as an adult, like switching careers from politics to business, played out in the same exact way. I didn’t reflect on what I loved about politics nor did I keep in touch with my community from that time in my life. I just moved on. But it’s not just about an appreciation of what’s past. When you rush a transition while you’re still in The End, you’ll look backwards for answers for what’s next because you’re still the same person. You’ve bypassed The Messy Middle and might think you’re in a New Beginning. But are you?

What would my life have looked like had I taken the time to go through each stage of the transition? Not rushing forward because it hurt too much to look back. While my childhood transition was a forced external one, my midlife one isn’t. And so I want to rethink how I’m approaching this time in my life with more intention, space and time to experiment and play. What would it look like to not have any idea what The New Beginning looks like? To sit in the liminal space for however long it takes to see what’s possible next.

Dileepan Siva is a serial entrepreneur, executive coach and writer helping high-performance leaders achieve success from the inside out. His work has appeared in The New York Times, Fast Company and TechCrunch focusing on entrepreneurship as a mirror to our inner world, friendship in the age of loneliness and how to cultivate belonging with ourselves.

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