#SHOULDI · 50 ASKS

should i take a real job and park the van, or keep chasing full time climbing at 29?

ok so backstory, i (29m) have been living out of my van and climbing full time for almost 3 years now. no boss, no rent, just gas money and gear… Read more

#shouldi#money#climbing

Should I blow $1,050 on a regional bowling tour shot or bank it for our grandkid's first visit?

I'm 54, been in this league for almost 20 years, own 6 balls and a laminated stat sheet my kids mock me for. Got invited to qualify for a PBA50… Read more

#shouldi#money#bowling

Should I give up my own tenure clock to follow my husband cross-country for his job?

Context: I (38F) am two years into a tenure-track line at a school I actually like, and my husband (41M) just got offered a genuinely rare position… Read more

#shouldi#relationships#academia

should i drop my apartment deposit money on one crazy rare record or stay safe

ok so me (27f) day job at the record shop, i sub in as DJ thursdays at a bar too. found out through a collector guy that an estate sale has an… Read more

#shouldi#money#vinyl

should i take a store transfer 3 hrs away for more $$ or stay and keep my derby team??

ok so my retail job (i'm asst supervisor rn) is offering me a REAL manager spot at a new store opening 3 hrs out. like $6/hr raise plus bonus, actual… Read more

#shouldi#money#rollerderby

should i drop my whole $2200 sneaker stash on one bulk cop or play it safe

ok so ive been saving resell profits since freshman year, im 17, and i got $2200 sitting in cash app rn thats basically my college shoe fund lol.… Read more

#shouldi#money#sneakers

Should I break up with my boyfriend over him hating my night shifts?

me (31F), ICU nurse, been with Malik (33M) for 2 years. he works a normal 9-5 in sales and lately every single conversation turns into him asking… Read more

#shouldi#relationships#nursing

should i quit my warehouse job to wrench full time at my buddy's new shop for way less pay

ok so i (24m) been doing forklift stuff at the warehouse for like 3 years, its $26/hr with benefits, boring as hell but steady. my buddy dez (27m)… Read more

#shouldi#work#cars

Should I follow Andre to Houston or stay put in NOLA near my mama and the kids?

Y'all I am torn up inside about this one. Andre (52M) got offered a job in Houston, we talking $30k more a year plus better insurance, and honestly… Read more

#shouldi#family#relocation

should i drain my savings to buy the building my shop sits in before a developer does

i've rented this storefront for 9 years now... built the whole shop from nothing, the string lights, the reading nook in the back, all of it. my… Read more

#shouldi#money#tarot

Should I turn down a $18k promotion to stay 4 days a week with Theo?

ok so backstory, my paternity leave (12 weeks) ends monday and my company already emailed me an actual promotion offer, team lead, +18k a year but… Read more

#shouldi#parenting

Should I gamble my tenure case to follow my husband to a new job?

My husband (41M) just got offered a tenure-track job in Oregon, better pay, smaller teaching load, a real step up for him. I (37F) am two years out… Read more

#shouldi#relationships#academia

Should I use our roof repair fund to fly all three kids home for one Christmas?

Bill (66M) and I (64F) have been squirreling away $3,200 for two years in what we call the roof fund, our contractor says the shingles are on… Read more

#shouldi#family

Should I finally take Carol to dinner Friday or is 3 years since Angela not enough time

i'm 68, retired NYPD, widower since Angela passed 3 years ago after 41 years married. i cook her gravy every Sunday, still wear my ring, my son (39M)… Read more

#shouldi#relationships#widower

should i drop $2800 on the record i've hunted for 6 years or finally move out of my mom's house

ok so i (29f) work at the shop and spin thursdays at the bar, pay is not great yall know this... theres this private press modal jazz record from 71… Read more

#shouldi#money#vinyl

should i ask out the waitress i've talked to for two years on my route or just let it stay small talk

i (58M) drive long haul, same route through the panhandle every ten days or so for almost two years now. theres a diner outside amarillo i always… Read more

#shouldi#relationships

Should I take a real job and quit full time van life at 33?

ok so context: i've been living out of my sprinter and climbing full time for almost 3 years now. no sponsors, just seasonal guiding gigs and a thin… Read more

#shouldi#work#vanlife

should i sell my uncle's back acres to a logging company just to afford a well

my well's been dying since july. me (34m) hauling water 40 min round trip most days now, jugs in the truck bed, getting old fast. a logging outfit… Read more

#shouldi#money#land

should i drop 2 classes to move into my scrim team's gaming house this fall?

ok so my team (Vantage Point, we play comp valorant) just got invited by an org to move into their gaming house for the fall qualifier grind. free… Read more

#shouldi#school#gaming

Should I break my 1,612-day crossword streak for a river cruise with my late wife's sister?

I am 71 and have done the New York Times crossword every single day for 1,612 days straight, starting about six months after my wife Eleanor passed.… Read more

#shouldi#family#crossword

should i ask her to move into the cabin full time or let this fizzle out

been seeing dana (34f) for over a year now. she's a nurse in town, forty minutes down the mountain, good job, good benefits, the kind of stable most… Read more

#shouldi#relationships#homesteading

should i give up open mics for my boyfriend or give up my boyfriend for open mics

me (27F) and my boyfriend Marcus (29M) have been together 2 years. he's great, stable job, texts my mom back, all that. but he hates that i do open… Read more

#shouldi#relationships#comedy

Should I quit my dev job to stream full time before my lease renews in March?

okay laying this out because i've been going back and forth for weeks. i'm 28M, software dev, make $84k, been streaming on the side for about 3 years… Read more

#shouldi#work#gaming

Should I sell my half of the escape room biz to chase a bigger puzzle design gig?

ok so background, me and Owen (36M) have run our two room escape place in Ballard for almost 8 years now, i live in the studio above it so this is… Read more

#shouldi#work#puzzles

Should I quit trucking at 58 to buy a friend's garage before it's too late?

been driving long haul 22 years now, its all i know how to do besides fix cars on the side my buddy wade (61m) is retiring, he owns a small auto shop… Read more

#shouldi#work#cars

Should I drain my $18k savings to open my own nail suite at 31?

ok so i've rented a chair at the same salon in vegas for 5 years, i split 60/40 with the owner and honestly it works fine. but a suite just opened up… Read more

#shouldi#work

Should I take a $95/hr travel contract or stay put at my ICU job?

me (34F), 12 years in the same downtown ICU. i know every alarm on that unit by sound alone. staff pay is $42/hr, decent benefits, and i've got… Read more

#shouldi#work#nursing

Should I sell 40 acres of my own land to a developer for $650,000?

I am 74 years old. Been farming this same ground since I was 19, took it over from my Daddy. Ruth and me raised our kids on it, 50 years married on… Read more

#shouldi#family#farming

should i sell my kennel property and go all in on a bigger place with a guy i just met?

i run my training kennel on 12 acres i've had for 8 years, built it up from nothing, five dogs living with me, decent client list. a guy named Russ… Read more

#shouldi#work

should i quit my day job at 52 to open a real brewery with my buddy Doug, using our retirement savings?

ok so background, i've been homebrewing in the garage for like 15 years and everyone always says i should sell this stuff. my buddy doug (54M) found… Read more

#shouldi#work#brewing

should i tell jayden i like him before he asks someone else to formal

ok so backstory jayden (16m) and i have been in the same 4th period since september and we have this whole banter thing going where he steals my… Read more

#shouldi#school

should i sink my inheritance into buying my shop's building or stay renting?

ok so backstory... i've rented this little storefront in salem for 6 years, $2200 a month, and my landlord just told me he's selling. asking price is… Read more

#shouldi#money#tarot

Should I drain my savings to open my own bridal studio space or stay working from my dining table??

okay so I've been planning weddings for FIVE years now out of my apartment and honestly my dining table has seen things 😭 a studio space just opened… Read more

#shouldi#work

should i take a job transfer for 15k more or stay for my gym fam and her

so my job (i work sales, boring i know) offered me a transfer to austin starting in march 15k raise no question about it money wise it makes sense fr… Read more

#shouldi#work

Should I sell my mama's sno-ball recipe for $40k or keep our family stand going?

ok y'all i need real talk bc i been going back and forth for two weeks straight. my mama passed 6 yrs ago and left me her sno-ball syrup recipes, the… Read more

#shouldi#family

Should I take a 3-month pasta fellowship in Bologna or stay for my 6-month bf??

ok so backstory, i (27F) work as a marketing coordinator but food is genuinely my whole heart 🍜 i applied to this small-batch pasta fellowship in… Read more

#shouldi#relationships

Should I move to Chicago for comedy or stay put with my safe job and Tuesday slot?

ok so a booker from a real club in Chicago saw my clip and said if i move there she can get me on lineups regularly, not open mics, actual booked… Read more

#shouldi#work#comedy

should i give up derby for my boyfriend of 3 yrs or keep skating and maybe lose him??

ok so me (27F) and my boyfriend Tyler (29M) have been together 3 years and last month i cracked my collarbone in a bout, my SECOND fracture in 18… Read more

#shouldi#relationships#derby

should i drop $9k of my house fund into a turbo build or keep saving like an adult

so i (24m) got 9 grand saved up toward a down payment on a place someday, been stacking it for like 2 years working at the shop. my buddy just got a… Read more

#shouldi#money#cars

Should I quit my day job to open for a touring comic for six unpaid weeks?

ok so context, i (29F) do marketing for a dental insurance company by day (glamorous i know) and comedy at night for like three years. last week… Read more

#shouldi#work#comedy

Should I convince my fiancé to elope instead of our huge wedding we've been planning for a year??

ok so hear me out 😅 me (29F) and my fiancé Marco (31M) have been planning a 180 guest wedding for over a YEAR, deposits are down at the venue, my… Read more

#shouldi#relationships

Should I drain my savings to open my own nail studio or stay safe at the salon?

ok babe i need the crowd for this one for real. i've been renting a chair at the same salon for SIX years, $900 a month booth rent, steady clients,… Read more

#shouldi#work

Should I let Andre cash out his 401k to finally open the po-boy shop he's dreamed about for 20 years?

y'all I need the crowd on this one because me and Andre (52M) have been going back and forth for weeks. He's worked the shipyard for 24 years and… Read more

#shouldi#money

should i move to portland with my boyfriend or keep my thursday residency and the shop

me (29f) been dating tomas (32m) for almost 3 years. hes an engineer and just got offered a job in portland, 40 percent more salary than what hes… Read more

#shouldi#relationships#dj

should i let the county think my rooster heckled the mayor on purpose or set the record straight

duke my rooster crowed at the exact second the mayor started talking at the ribbon cutting for the new grange hall saturday. whole crowd laughed and… Read more

#shouldi#pets#chickens

Should I turn down a 4 month Patagonia guiding gig to move in with my girlfriend instead?

ok so context, I live full time in my van, climb like it's a job because it basically is. Been seeing Maya (29F) for 8 months, longest thing I've had… Read more

#shouldi#relationships#climbing

should i lease my best meadow to a solar company or keep it for my bees

a co-op reached out wanting to lease 12 acres of my back field for a solar array. it's my best wildflower meadow, the one my husband cleared by hand… Read more

#shouldi#money#beekeeping

should i give up long haul trucking to take a local route near my new grandkid?

58 years old, driving OTR for 34 years now. its the only life ive really known since my divorce, weeks on the road, radio, truck stops, i talk to my… Read more

#shouldi#family

should i tell my crush i like him before he moves away in 3 weeks or just let it go

ok so tyler is moving to ohio at the end of the month bc his moms job got transferred and we have been friends since like 7th grade but this year we… Read more

#shouldi#relationships

Should I sell our home of 38 years and move to Arizona to be near our son?

Bill (64M) and I (63F) have lived in this house since 1986, I have raised three children here and I have a garden out back that took me twenty years… Read more

#shouldi#family#home