Essays by Kip Durney

Writing from the Middle.

Reflections on work, family, and the unexpected moments in between.

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Latest essay

Family

For Annie

I didn’t want to write this post. But I feel helpless right now, and this is the only thing I know how to do. My mother-in-law passed away after a long battle with stage 4 Alzheimer’s. It was a hard twenty months for everyone, for more reasons than I can list. The waiting. The watching. The kind of pain that doesn’t really have a name, because it wasn’t pain so much as love with nowhere left to go. If you’ve been through this, you understand. If you haven’t, your empathy still means something to us. What this disease took from ... Read more

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Business

The Year I Finally Stopped Pretending I Had It All Figured Out

The Year I Finally Stopped Pretending I Had It All Figured Out Personal Essay · Life & Leadership The Year I Finally StoppedPretending I Had It AllFigured Out A confession from someone who spent decades with a plan, and what happened when life quietly refused to care about it. A few minutes well spent ☕ Here’s my confession: I was the guy with a Plan. Career mapped. Goals spreadsheeted. Milestones color coded. I was so organized, I probably had a backup plan for my backup plan. Sound familiar? For years, it worked. I built a career I’m genuinely proud of, ... Read more

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Welcome. I’m glad you’re here.

This site is a place for writing (and venting). Not announcements. Not hot takes. Not productivity hacks. Just writing. For most of my adult life, I’ve written in the margins. Notes during long meetings. Drafts that never left my laptop. Half-finished thoughts about work, family, ambition, fear, and the strange distance between the life we plan and the one we actually live. From time to time, I shared some of that writing publicly. When I did, the response was at times almost overwhelming but usually it was quiet but meaningful. A message from someone who recognized themselves in a sentence. ... Read more

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Work

Learning Out Loud

Good Work and Good Leadership Are Not Opposites I once worked on a project where people were afraid to tell the truth. They lost sleep thinking about work. They missed family events to meet deadlines, not because the work required it, but because they feared what leadership would say if they didn’t. Meetings were painfully tense. No one spoke up. No one suggested alternative ideas. The possibility of missing a deadline or raising a concern about the timeline felt unfathomable. The project delivered. But the cost was real, and it was paid by people who deserved better. Myself included. Somewhere ... Read more

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Kids

93 Days: A Lesson in Life, Love & Hope

The fact that the girls are now in school amazes me, considering their humble beginnings. Like many things in life, the beauty is in the journey, and it’s taken me some time to really accept and process the journey that brought us here. When Val and I first got pregnant, the feeling was nothing less than sheer jubilation. It was planned. We were ready to take on the challenges of being first-time parents. Our initial experience was textbook—home test, prenatal vitamins, first doctor appointment to hear the heartbeat. Everything was normal until that one day, that one test, that one ... Read more

Read · 15 min
Kids

Open Letter to My Son

Connor, I wrote the first version of this letter when you were five years old. As you approach your 13th birthday and edge closer and closer to high school, I can’t help but think you’re growing up too fast. While life has certainly challenged us in ways none of us could have ever imagined over the last few years, I have no doubt that you will succeed in anything you choose to do in life. As a father, there’s something special about having a son. Of course I love your sisters as much as you, but it’s different. They are ... Read more

Read · 4 min
Kids

Open Letter to My Daughters

A&Z, I have sat down for the past several months trying to write this letter to you both but have not been able to find the words. I wrote Open Letter to My Son with relative ease, so I have been perplexed as to why I have had such a hard time writing to you. Until today. You both are the miracles that almost never came true; your births embody the best and worst moment of my life. I was forever changed that day, in both good ways and bad, but I’m realizing now that my consternation in writing to ... Read more

Read · 5 min

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About

Kip is a writer shaped by work, family, and a long stretch of life that has offered both perspective and humility. He writes from the middle of things, somewhere between having learned a few lessons and still getting plenty wrong. Kip lives, works, and writes outside of Boston, MA with his wife, 3 teenaged kids, and 2 dogs.

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New essays land on Substack first. The rest of the time I’m sharing work, family, and the in-between on these channels.