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Celebrate Someone, and Next Chapter Together!
Building a community of encouragement.
Aug 6
•
Jen Leo
18
4
What I Found When I Stopped Waiting
A solo afternoon in Barrio Logan reminded me that curiosity doesn’t need company.
Aug 2
•
Jen Leo
6
2
1
July 2026
The College Dashboard Is Working
How one dining room wall gave Cora ownership of the plan—and helped me stop asking so many questions.
Jul 15
•
Jen Leo
19
12
4
June 2026
Before Senior Year: Our Family’s College Application Plan
Four months until deadlines, a blank dining room wall—and the moment that made me feel better about letting go.
Jun 24
•
Jen Leo
16
5
2
The Leaving Starts Before the Leaving Starts
On grief, flank steak, Swedish Death Cleaning, and making room for what’s next.
Jun 11
•
Jen Leo
25
11
2
Three Days Left of Junior Year
Everywhere I look, I can see what’s coming next.
Jun 3
•
Jen Leo
16
4
2
May 2026
Peanut Butter and Grief
Katie is still looking for Cooper. Honestly, so am I.
May 28
•
Jen Leo
12
15
4
I Stayed Up With ChatGPT Researching Italian Towns After My Husband Went to Bed
Apparently my husband, my AI boyfriend, and a points transfer sale staged an intervention.
May 27
•
Jen Leo
10
8
2
On Letting Go: The Driving Chapter
Small acts of protection, bigger acts of trust
May 25
•
Jen Leo
19
12
2
Confessions of a Junior Mom: I’m More Scared of Summer Than Senior Year
I don’t remember ever seeing my dad cry until three weeks before I left for college.
May 24
•
Jen Leo
6
3
Family Game Night at the End of Junior Year
Right now our house is somewhere between studying for finals, cramming for the Speech & Debate banquet, thinking about Nationals, squeezing in work…
May 19
•
Jen Leo
9
The Conversations We’ve Had With Cora About Choosing a College
Three generations of opinions, one hopeful dad, a very pointed kid… and what we’ve learned about choosing schools
May 18
•
Jen Leo
5
5
3
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