Will Your Future Self Thank You (Or Regret) How You’re Showing Up Now?

This past week, my conversations with two newly retired business leaders got my Emily-brain whirring.

Both seemed to be thoughtful, decent human beings and had served for decades in highly regarded business roles. I came away from each wondering whether one might more easily navigate this phase of life compared with the other.

Some background: It’s hard for my ears not to perk up when I hear someone say, “I recently retired.” So, at some point when no one was around, I asked each, “So, how’s it going?”

“Fred” expressed concern about his identity now as a retiree. The costly membership dues being paid by his company for his seat on a regional business board will expire. While the company may choose to put a new executive into the slot, unless Fred shells out some big bucks, he will likely need to step away. Fred wonders what that will mean for him: what his usefulness will be, and what will happen to those relationships.

“Joe” seems relatively well at ease. He serves on no organizational boards. Yet, a few leaders with whom he’s enjoyed enduring relationships throughout his career have stayed in touch, and even reached out to him recently for his perspective on a pressing community issue. He’s energized by the idea of donating some time to support efforts he finds meaningful—with people he cares about.

My Spidey-sense, walking away from these fairly deep conversations, suggests that how each man has shown up in his career—perhaps in his life—at least in part explains the difference. And I wonder whether the degree to which their relationships with others have been characterized by transactional versus non-transactional interactions is playing a role.

Transactional relationships are where we’re in it for ourselves, and we do things for each other with the expectation of reciprocation. Non-transactional relationships are ones where the relationship itself is the reward. To be clear: neither is right or wrong, and we need both for sure. My husband and I would not be married if we didn’t both desire and expect reciprocation. The whole “through sickness and health” thing comes to mind, just for starters.

My takeaway from these conversations and my musing for today: if the tilt isn’t balanced toward non-reciprocal, our later life years will be more fraught.

Of course, we can’t live every moment in deep connection with every human being we encounter. I believe those words become even more important in later life—and yet, we can begin to take them to heart now:

There’s no time like the present, and it’s never too late, no matter where we are in our phase of life, to revisit how we are showing up in our relationships—and what’s happening in our conversations.

3 things we can do NOW, no matter our phase of life:

  1. We can revisit our network. As we reconsider the people with whom we spend our time, the amount of time, and the quality of that time, what’s our transactional vs. non-transactional tilt looking like? Any adjustments needed in that ratio—and therefore, how we spend our time?

  2. We can revisit the intention and content of our conversations with people. Start by setting a completely different tone right off the bat. For example: whether it’s during the conversation itself, or in teeing up a request for a conversation, we could share something we really like about them! And yes, it needs to be something we actually really like, as opposed to something we say to butter somebody up. (OK, that was a bit harsh, but you get the idea.)

  3. We can acknowledge our regret (love Daniel Pink’s brilliant book on the power of regret) at being transactional with people and commit to trying a reset. The recipe? A dose of humility, putting our foolish pride to the side, and leading with vulnerability—perhaps even an apology as we ask to meet for coffee. We can choose to be brave: “A brave life is basically 15 fricking hard conversations a day.” (Shoutout Brené Brown, NYT interview last week.)

Whether it’s being proactive about ensuring your post-career life keeps you connected in the most impactful way with people who matter to you, or you’re just wanting to show up now in a more vulnerable and authentic way, I say let’s do it! 😊

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