Manager from Pittsburgh
Firing my best friend
I run a 12-person team. My best friend since college is my worst performer.
From Spurs–Thunder Now a Best-of-3, Knicks Rolling But… Plus Draft Intel & All-NBA Snubs w/ Sam Vecenie — May 25, 2026
All emails
Every Life Advice email we've archived. 19 in total. Tap a theme to narrow down, or scroll the full list.
Couple in Texas
Relocating for in-laws
Wife's parents need help. We'd move 1,400 miles and I'd take a 30% pay cut.
From Spurs–Thunder Now a Best-of-3, Knicks Rolling But… Plus Draft Intel & All-NBA Snubs w/ Sam Vecenie — May 25, 2026
Coach Dad
Coaching my own teenage son
I coach my son's JV basketball team. He won't listen to me. Step down?
From Spurs–Thunder Now a Best-of-3, Knicks Rolling But… Plus Draft Intel & All-NBA Snubs w/ Sam Vecenie — May 25, 2026
Best-Man Andy
Friend got engaged, friendship cooling
I'm supposed to be the best man. We haven't hung out one-on-one in 4 months.
From Knicks Up 2–0 & OKC Bounces Back w/ Jon Krawczynski, Plus a Potential 24-Team CFB Playoff w/ Danny Kanell — May 22, 2026
Software Engineer
Remote-only offer with 20% pay bump
Current job hybrid; new offer fully remote, 20% more, but a startup I'm unsure about.
From Knicks Up 2–0 & OKC Bounces Back w/ Jon Krawczynski, Plus a Potential 24-Team CFB Playoff w/ Danny Kanell — May 22, 2026
Recent Grad
Law school vs. startup gig
Just got into a T14. Also got a $130k offer at a Series B. Which path?
From Knicks Up 2–0 & OKC Bounces Back w/ Jon Krawczynski, Plus a Potential 24-Team CFB Playoff w/ Danny Kanell — May 22, 2026
Grandkid
Grandpa gone wild (dating much younger)
Grandpa is 74. New girlfriend is 38. Family is split. Do I say something?
From Chiefs, Bucs, and Drake Maye Are Big Winners. Plus, Danny Kanell on Penn State’s Overreaction, Indiana’s Biggest Win, and the SEC’s Problem. — Oct 13, 2025
Divorced Dad
Holidays after divorce
First Christmas split. Kids 9 and 12. Ex wants Christmas Eve every year forever.
From Chiefs, Bucs, and Drake Maye Are Big Winners. Plus, Danny Kanell on Penn State’s Overreaction, Indiana’s Biggest Win, and the SEC’s Problem. — Oct 13, 2025
Roommate Sarah
Roommate eats my food
My labels are in Sharpie. She eats it anyway. Confront or move?
From Chiefs, Bucs, and Drake Maye Are Big Winners. Plus, Danny Kanell on Penn State’s Overreaction, Indiana’s Biggest Win, and the SEC’s Problem. — Oct 13, 2025
Thirty-Two
Moving back home at 32
Bay Area rent broke me. Parents have room. Career suicide or smart play?
From Chiefs, Bucs, and Drake Maye Are Big Winners. Plus, Danny Kanell on Penn State’s Overreaction, Indiana’s Biggest Win, and the SEC’s Problem. — Oct 13, 2025
Late-Career Pivoter
Career pivot at 45
45, 20 years in finance, want to teach high-school math. Stupid?
From Prime-Time Giants! NBA GM Survey Thoughts. Plus: Jeff Darlington on Baker’s Career Turnaround, Shanahan Love, and Belichick’s future. — Oct 10, 2025
Younger Sibling
Older brother always one-ups me
Every life update, my brother has done it bigger. How do I handle holidays?
From Prime-Time Giants! NBA GM Survey Thoughts. Plus: Jeff Darlington on Baker’s Career Turnaround, Shanahan Love, and Belichick’s future. — Oct 10, 2025
Best Man Stuck
Wedding toast about a groom I've grown distant from
Bachelor party in 6 weeks. We barely talk anymore. Honest or polished?
From Prime-Time Giants! NBA GM Survey Thoughts. Plus: Jeff Darlington on Baker’s Career Turnaround, Shanahan Love, and Belichick’s future. — Oct 10, 2025
New Manager
Inherited a team I'd fire half of
Promoted internally. Half my new team probably needs to go. Pacing?
From Prime-Time Giants! NBA GM Survey Thoughts. Plus: Jeff Darlington on Baker’s Career Turnaround, Shanahan Love, and Belichick’s future. — Oct 10, 2025
Long-Distance Lisa
Two-year long-distance, decision point
Both have stable jobs in our cities. He won't move; I'm considering it.
From The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice! — Oct 8, 2025
New Husband
In-law conflict ahead of holidays
Mother-in-law refuses to acknowledge my career change. Wife won't confront her.
From The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice! — Oct 8, 2025
Late-Thirties
Kids decision in late 30s
Married 4 years, no kids. He's pushing, I'm on the fence. 38 next month.
From The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice! — Oct 8, 2025
Estranged Sibling
Reconnecting with estranged brother
Haven't spoken in 11 years. He just emailed asking to meet.
From The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice! — Oct 8, 2025
Underpaid Engineer
Asking for a 25% raise
Outside offer at +30%. Boss has told me to "be patient" twice. How do I play this?
From The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice! — Oct 8, 2025