1. If you should move somewhere cheaper.
The big city is great in your twenties, since living in a tiny apartment and eating soup every night is a small price to pay for access to “live the dream.” However, in your thirties stuff like “comfort” and “space” begin to take priority.
2. If you should go back to school.
Maybe things haven’t panned out the way you wanted, but will getting that extra degree solve it? Maybe, maybe not.
3. Which weddings to attend and which ones you shouldn’t.
Some you are obligated to, some are just too damn far, and some you barely the know the people getting married. Either way, it is money out of your pocket so choose wisely.
4. Whether or not to bring a date to that wedding.
Because sometimes “will you have a +1?” is a harder decision than it seems.
5. If you should get married.
I guess this depends on your relationship status, but even if you aren’t in any hurry the fact that so many of your friends are taking the plunge will make you wonder if you should too.
7. If you should start looking out for your health more.
Why does everyone hit the big 3-0 and decide to begin work out more? Especially starting to run?
8. Whether or not you should take that trip.
It is a lot harder to just cut and run now, but that doesn’t mean you should deny yourself the chance of experiencing new places, especially if you can afford it.
9. If you should attend your 15 or 20 year high school reunion.
Because there is nothing better than being reminded of old you are getting than seeing how much grayer and fatter your former classmates have become.
10. If it is alright to splurge on things you don’t really need.
The problem is that you are now experienced to know that some things are to be invested and some things aren’t. But treating yourself every now and then can’t hurt, right?
11. Whose side to choose when your married friends divorce.
Why do I have to choose? In the words of Rodney King (RIP), “Can’t we all just get along?”
12. If you should buy some property or invest in something.
Because that’s what adults do, right?
13. Whether or not to have that next drink.
The three day hangover is realer than real these days, and one more mojito might send you there quicker than you would like so be careful.
14. If you should see that band you used to love.
Sometimes memories are best left untampered with.
15. If you should cut the cord and just do streaming.
With Netflix, Hulu, and Amazon Prime who needs cable? Oh, yeah. Game of Thrones. Damn you, HBO, for making this a harder decision than it needs to be!
16. If you should cut back on your favorite foods from your twenties.
If not, then it is time to head to Costco and stock up on Prilosec and Lactaid.
17. If you should see a doctor about that thing.
Eh, it’s probably nothing to be worried about. OR IS IT?
18. If you should bring one bottle of nice wine to that dinner party or two bottles of cheap stuff.
One is classier, but two will get you drunker. Decisions, decisions.
19. Also, wondering if you can get away with wearing sweatpants to said dinner party.
Because we’re all adults and you’re going to be comfortable, dammit!
20. Deciding if it is too late to switch career paths.
Sometimes a change is needed so follow your heart and see where it takes you.
21. Whether to sever those less than great relationships, especially the romantic ones.
You probably did this in your twenties a couple of times, but guess what? Even in your thirties toxic relationships can rear their ugly heads, so be warned.
22. If you should block your friends who keep posting pics of their kids.
We get it. You’re a parent now. Congratulations.
23. If you should have a kid.
“Tick tock.” – Your mother.