Identity & Values
Dear Toolsie,
is it weird that I still sleep with a stuffed animal at 16
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I got into two grad programs and honestly don't know which one to pick, they're both good
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I'm 68 and thought about going back to work part time just to have somewhere to be, but I'm worried people will think I need the money.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I'm turning 40 next month and I keep having this weird panic like I haven't done anything with my life.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I used to paint all the time and somewhere in the last few years I just... stopped, and I miss it but can't get myself to start again.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I'm 52 and just started guitar lessons and I feel embarrassed telling people, like I should already know how by now.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I want to go back to school for something completely unrelated to my career and I don't know if that's irresponsible at my age.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
is it weird that i've rewatched the same show like 4 times instead of trying anything new
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Someone is using my name and photos to scam people on a dating app, is that even illegal and what do I do?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
okay so I don't even know where to start honestly, work has been insane, my manager keeps piling on projects and then also my coworker who I used to be close with stopped talking to me after I got the promotion she wanted, and I feel guilty about that even though I didn't do anything wrong, and on top of that my apartment lease is up in two months and I can't decide if I should move to a cheaper place across town or just stay even though rent is going up again, and my mom keeps calling asking when I'm visiting and I keep putting it off because honestly I'm exhausted every weekend, and I also haven't been sleeping great, like I lie awake replaying conversations from years ago sometimes, and I don't even know what I'm asking you here, I guess I just needed to get it all out somewhere, is there something wrong with me or is this just what being an adult in your thirties feels like for everyone
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I turned 40 this year and realized I've never actually lived alone, and I don't know if I should finally try it or if it's too late to bother.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I quietly stopped believing in the religion I was raised in, and I haven't told my family because I know it will change how they see me.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I got a big promotion and instead of feeling proud I mostly feel like a fraud who's about to be found out.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I've been the 'reliable one' in every relationship in my life and I'm exhausted, but I don't know who I am if I'm not that person.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I keep starting hobbies enthusiastically and abandoning them within a month, and I'm starting to wonder if the problem is actually me.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I said yes to a huge life change — moving across the country for a relationship — and now that it's actually happening I'm terrified I did it too fast.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I realized in therapy that I've been the difficult one in most of my past conflicts, not the victim I always thought I was, and I don't know what to do with that.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, everyone tells me I seem so put-together, but I feel like I'm just really good at hiding how lost I actually am.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I've started to suspect I'm neurodivergent in my thirties and I don't know if getting evaluated would actually help or just give me a label to obsess over.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, I retired last year expecting to feel free, and instead I feel useless most days and don't know how to bring that up with my spouse.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Am I too old to start over in a completely different career at 52?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it ridiculous to keep training for a marathon I might never actually finish well?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
How do I know if a dream is worth disrupting the life I've already built?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
What would happen if I just stopped being so practical about everything, even just once?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Can a hobby I only started for fun actually turn into a whole new chapter of my life?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it too late to learn an instrument I always wanted to play as a kid?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
How do I tell the difference between settling and just being realistic about what I want?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it foolish to want to move somewhere completely new at this point in my life?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
What's actually stopping me from trying the thing I keep saying I'll do "someday"?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it worth going back to school in my 40s for something that might not even pay off?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
How do I figure out what I actually want, versus what I think I'm supposed to want?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is wanting a completely different life a sign something's wrong, or just normal restlessness?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
What would it look like to take my side project seriously instead of treating it as just a hobby?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Am I chasing a dream, or avoiding something I don't want to deal with?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
How do I stop waiting for the "right time" to try something I actually care about?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it selfish to want to change my life in a way that affects the people around me too?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
What's the real difference between giving up on a dream and finally being honest about it?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
How do I know if I still want this dream, or if I just don't want to admit I've changed?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it too late to become the kind of person I always pictured myself being?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
What would I actually do with my time if money weren't part of the decision at all?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
How do I know if a big leap is bravery, or just running from something?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it okay to want something different from what I built my entire life around?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
What's one version of my life I never let myself seriously consider?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
How do I tell the difference between a real calling and a passing obsession?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Is it possible to want both stability and adventure, or do I really have to choose?
Toolsie wrote back.
Identity & Values
Dear Toolsie,
i got waitlisted at my dream school and got into my safety school with a full scholarship, everyone keeps telling me to just be grateful but i cant stop being sad
Toolsie wrote back.
Identity & Values
Dear Toolsie,
i cheated on one exam freshman year and got away with it, and now two years later it's eating at me every time someone praises my gpa, do i actually have to do anything about this
Toolsie wrote back.
Identity & Values
Dear Toolsie,
At 61, I'm finishing the bachelor's degree I dropped in my twenties, and my grown children think I should be spending that money on retirement instead.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I changed my name legally two years ago and my grandmother still won't use it, and I don't know if I should keep correcting her or just let her call me what she wants.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
everyone says im 'so mature for my age' and i used to like hearing that but now it just makes me feel like i skipped being a kid and i dont know how to explain that to anyone
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I've spent fifteen years building an identity around being 'the reliable one' in my family and friend group, and lately I resent it, but I don't know if I'm allowed to just stop being that person after this long.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I started therapy for the first time at 45 and keep feeling embarrassed that it took me this long, like I should have figured myself out by now.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
I've dreamed of opening a small bakery for a decade, and I finally have enough saved to try, but launching now would mean walking away from a stable job right when my family needs the stability most.
Toolsie wrote back.
Identity & Values
Dear Toolsie,
Dear Toolsie, how can my partner and I agree on where to spend the rest of our lives? We're both 70. I love a big city and he loves a more rural setting. We also want to be driving distance to our two kids (one in a town in one state, one in a city in a neighboring state).
Toolsie wrote back.
Done here? Read a letter at random