1. You’ll regret your financial promiscuity. That $30,000 loan you took out to complete a now useless BA in general arts is seriously difficult to pay off. Perhaps going on yet another all-inclusive $2000.00 vacation with your friends is a bad idea. A homemade lunch becomes your reality. Seriously, $5 bagels at the gourmet coffee shop are really not worth it.
2. You begin to compare yourself to other successful people that are your age. At or around the age of 27, you’ll begin to feel like you’re behind in life’s game of Monopoly. You blame Becky’s success because of her grandmother’s inheritance, when in reality you come to the realization that everything you believe you’re lacking in life is seriously your very own fault. Trolling other people’s LinkedIn profiles makes you feel insanely behind. The worst feeling: going to your best friend’s magazine-worthy $70,000 wedding when you’re struck with the realization that if you wanted to get married all you could afford is a City Hall ceremony. You feel like a failure, all the time.
3. You feel lost. Your late twenties will bring on questions in your head that go to the tune of, “I never thought I’d still be in an entry-level position…when the hell am I going to get promoted” or “I thought I’d be married with children by now.” You start to question all of the decisions that you’ve made up until this point in your life and second-guess your career aspirations; however, you seriously dread the thought of going back to school, no matter how much your mother may suggest that that’s your only option at this point.
4. You’re becoming more cautious. All of a sudden you start getting scared of almost everything that never used to scare you when you just graduated from high school. Staying up till 3am partying on a Wednesday night? No way, I have work in the morning and those TPS reports are due. Speeding on the highway? Heck no, my insurance will skyrocket and it’s simply not worth the risk. There’s nothing wrong with being cautious, but you honestly begin to miss that feeling of excitement and unpredictability that you innately had when you were in high school. All of a sudden – GASP – your life seems dull and boring. Not only that, you’re deathly afraid of losing your job because you’re well aware that there 10 other 22 year-old candidates waiting to pounce on your position.
5. Your life needs a total overhaul. You’ll begin to question everything about your reality. Should I still be living with my parents? Maybe I should travel alone for a year to discover myself. Maybe I should teach English in Korea and date a cute American pilot. Or better yet, maybe I should do a motorcycle trip like Che Guevara did in the “Motorcycle Diaries” and blog about it. You start to dislike your life in general and you come up with schemes on you’re going to change your life to finally accomplish something you’ll be very proud of. You dream of challenges and adventure, only to realize you don’t really have the money to do anything you want to. Eventually, you focus on the thought that you’ll have to get a second job to afford your lavish dreams, so you give up because you’re already tired from working 9 to 5. This makes you even more depressed and feeling like an even greater failure because you can’t focus or fulfill even your own desires!
6. You feel guilty for having a life crisis in your twenties. You feel like your life sucks and that you’re a failure, meanwhile you look at your 50 year-old neighbour across the street who just lost his job but still has a family to support and a mortgage to pay off. When thoughts come into your head about your lousy life and how reality stomped on your dreams and aspirations with a 6” stiletto heel, you’re reminded that you have “first world problems” and that children are starving in Africa. However, you still continue to feel like shit because you feel like no one really knows what you’re going through.
7. Charities. When going through this crisis, all of a sudden a light-bulb moment hits you and it involves volunteering with some kind of charity or doing something for the greater good. You begin to tear up watching SPCA commercials and you actually feel obligated to leave more than $5.00 in the Salvation Army jar during the holidays. Heck, you even plan on volunteering at your local hospital/animal shelter, all in an effort to feed your new desire to help others. With this newfound love of all things charitable, the guilt sinks in that you’ve been spending most of your twenty-something quasi-disposable income on things that don’t really matter. Wearing that $300.00 Michael Kors watch while you buy a $6 latte makes you feel like a shitty, shallow individual. You’re constantly plagued by guilt for wanting the finer things in life because all you can think about are those starving African children.
8. You start to look up to your peers who are in their 30’s. All of a sudden your current group of 20- something friends become mundane, so you venture to seek out other wiser souls. In an odd way, this time around, you’re more selective when you bring in a new friend into your life. If they’re in their 30’s, you assume it’s better because they’ve lived through the 20-something life crisis and they could potentially offer a fountain of knowledge. They slowly begin to serve as your life coach and you really listen to advice for the first time in your life because you’re not afraid to admit to yourself that you actually need it.
9. Other people don’t understand your issues. That guy who wrote “Why the Generation Y Yuppies Are Unhappy” – screw him. He doesn’t understand what it’s like to be in your twenties nowadays. Everything is that much harder, confusing, and filled with philosophic turmoil. Let him try to accomplish all the things that the older generation did in an environment plagued by the current job and economic crisis. Let him try and understand why all the people in their mid to late twenties feel special.
10. Self Help. For this first time in your life, your mid to late twenties will make you venture into the self-help section. Books like the “Power of Now” and “The Secret” are on prominent display on your bedside table and you’ve actually read them. Reality check: when the people in your life start buying self help titles for you because it’s becoming obvious to everyone that you’re in a crisis situation. 
