“I’m here to give back. I want to be able to talk to the 20-year-old Chuck who was afraid of losing his job because he wasn’t making his sales quota.”

A second-half-of-life kind of statement.

He was the first person I had ever met from Sioux Falls, and we were sharing how we had gotten to where we are in our businesses. His was a long history in sales, having hopped on the LinkedIn B2B marketing train early and was looking to either expand his agency and take on a lot of overhead or partner with companies like ours to outsource things like content and audience growth; mine was in academics. He wasn’t sugar-coating, selling, or BS-ing with me. I liked him.

I also thought I saw the face of a man who had carried some pain, like the lines on his face had been etched there by disappointments he never mentioned. He spoke of a brother who had brought him to this business, but then left on some kind of SaaS adventure.

A true Midwesterner who had learned to wear a stiff upper lip. And learned the art of loving his 20-year-old self.

He is quite a feat.

Self-compassion is an art form that we learn when we find ourselves in an uncomfortable and safe space, when the danger that appears to threaten us has passed and we realize that we’ll make it—“it” being that nebulous safety realized long after we’ve reached it. We see ourselves differently, as if we’re looking through some kinder, more gentle light like the eyes of a father seeing his daughter face to face over coffee when they haven’t spoken for years. Or a mother seeing a son suddenly a man. These eyes are worn, tired and see we were doing the best we could all along. We know we’ll make it.

Self-compassion has not come easily for me. It came through skills like mindfulness and soft touches: my hand on my chest or my cheek, learning to say kind words to myself from the voice of a parent or mentor, looking into my own eyes in the mirror. I recognized progress when I read a journal that 20-year-old Michael had written and for the first time did not feel anger at him for not having the same writing skills that PhD Michael has.

He was so earnest. Raised in Indiana. Learned to wear a stiff upper lip.

Last night, I was in Book 18 of Homer’s Odyssey. Odysseus is explaining in cloaked language to the young, impetuous Amphinomos how he used to think he was invincible as only youth can think. It wasn’t until he was on his way home from Troy that he learned how frail we are as humans, how learning to endure is a lesson in humility—our strength will fail. If he could have, I think Odysseus would have quoted Kevin Kling (“We pay for our laughter. We pay to weep. Knowledge is not cheap.”) and then finished with Metallica (“and choose your fate and die”). He extends compassion to his younger self while plotting the slaughter of the suitors.

And Amphinomos is one of the suitors whom we’re told will die by a spear thrown by Telemachus.

Is this what it’s like to hold the tension between the second half of life energy that values and leads with compassion while holding space for the needs your first half of life self still has to assert and fight for what you feel is rightfully yours?

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On being perfectly imperfect