HeyJaredThe Big Sister Playbook by DK
The big-sister playbook for ambitious women building careers and lives they love. I learned the hard way, and now I’m giving you the shortcuts.
- Indexed issues, last 90 days
- 5
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- Sep 27, 2026
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- Jul 13, 2026
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💌 38: Show Me the Bricks (opens the original)
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Subscribe nowOn Thursday, approximately 2,500 miles or so from my life, I got into a car on my way to sit on a panel about reputation management. I had been taking Waymos most of the week, mostly because there is something particularly soothing about getting into a car that cannot ask you how you are doing. But on Thursday I had a driver, and within approximately six minutes we had skipped weather and traffic entirely and moved on to trust, relationships, attachment theory, the fact that he had
💌 37: How to Be Sad (opens the original)
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Today Yom Kippur starts, the holiest time of the Jewish year, traditionally spent fasting, reflecting and atoning.I have decided I have done enough of all three.I have been fasting, although not intentionally. I have been reflecting to the point of exhaustion. And for two weeks and two days, I have been conducting what can only be described as a forensic audit of my own life.Subscribe now<a class="image-link image2 is-viewable-img" href="https://su
💌 36: The Days You Cannot See (opens the original)
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Thursday afternoon, I was standing on the corner of 44th Street and Fifth Avenue holding a bouquet of flowers and trying to hail a cab.It was sunny. I had just left a Reiki appointment in Midtown, and the flowers were for my birthday. New York was doing what New York does particularly well when your own life has fallen apart: carrying on without consulting you. People were leaving offices, crossing streets, looking at their phones, deciding what to have for dinner. Somewhere, someone was having
💌 35: Maybe You Don't Talk About Money Enough (opens the original)
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Years ago, I dated a man who told me I talked about money too much.<img alt="" class="sizing-normal" height="526.9419568822553" src="https://substackcdn.com/image/fetch/$s_!oNUY!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-medi
💌 34: Love the One You’re With (opens the original)
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The Fourth of July has always been my favorite holiday.And for as long as I can remember, summer has been measured by the East Coast. Weathered cedar shingles faded silver by salt air. Dunes rolling toward the water, threaded with beach grass and old wooden fences. American flags hanging from white clapboard porches. Screen doors slamming behind someone carrying lobster rolls wrapped in paper. Bare feet on old pine floorboards, sand somehow everywhere no matter how many times someone swept.<a cl
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