The advice I’ve given to new grads in the past is to marry rich so you have more options. And don’t go to grad school to get out of difficult choices. Consider moving home with your parents to save money and don’t do what you love.
This is all really good advice. You should go read those posts, but this year, my message to new grads is that you should make the mistakes I made when I graduated. They were good mistakes to make.
1. Ask for too much in the interview.
The first job interview I ever had was for the number one children’s book publisher atthe time, Harper Row. It was a long shot, but I sent my resume to their New York City headquarters, and I ended up getting an interview — my 10 years running our family children’s bookstore was worth a lot more than I realised.
When I got to the interview I didn’t understand that it was my job to sell myself. I thought that had already been done, and that’s why I got the interview.
We talked about my family’s bookstore and I wowed the interviewer with my encyclopedic knowledge of not only book titles, summaries, and authors, but also publisher imprints. Growing up there was no computer system. So my grandma and I, in an unintentional homage to our mutual Asperger’s, memorized every single detail about the inventory so that we didn’t need an inventory system. (Quiz me. I know every single children’s book published from 1975 to 1990 and the publisher’s imprint.)
It was clear in the interview that I was going to be offered the job and I got nervous. I spent the rest of the interview worrying out loud that I would be stuck in a job where I didn’t have time to play beach volleyball.
Of course, I didn’t get the job, but that was fine, because I really wanted just to play beach volleyball.
2. Spend all your savings.
The only beach I was familiar with was the North Avenue Beach in Chicago. When I was in the mental ward during college I dated a doctor who played beach volleyball there, and after I got out I spent the rest of the summer playing with him.
My best memories during college were of my time in the mental ward in North Avenue Beach. So I tried to duplicate it by moving back to Chicago. I got a stupid job as a bike messenger where I routinely got run over by taxicabs, and I came to the volleyball court bruised so many times that one of the players asked me to work for him at the Mercantile Exchange trading floor, another job that paid terribly, but one where I still got to play beach volleyball.
It didn’t take me long to realise that there were no professional beach volleyball players training in Chicago, and I had already spent my money getting an apartment in Chicago and working terrible jobs so that I could play beach volleyball in the afternoons.
So I ran out of money. I moved back in with my parents. I did more terrible jobs until I saved enough money to go to California. The process of running out of money and having to move back to my parents’ house was particularly awful. I felt irresponsible and incapable.
It’s important to spend all your money when you graduate because when you graduate, it’s the only time you can experiment wildly while trying to figure out what you want to do.
You can always move back to your parents’ house. If I can do it, anybody can. I hated my parents. They lived in a terrible location for someone in their twenties. I basically spent six months locked in my childhood bedroom, but it was a good: That got me to my next step. I moved to California.
3. Date terrible people.
It’s hard to get a real sense of your value on the dating market while you’re in college because all around you are other college people. Once you get out into the real world it’s absolutely incredible how many men want to date a 23‑year‑old woman.
So I experimented with a wide range: married men, rock stars, drug addicts, people who could pay my rent and people who could give me jobs. I would say that each of those relationships was hideous in its own way and could not be over fast enough, but if you don’t date the terrible people really early, then you always wonder what it would be like.
If you marry early someone stable and supportive and boring, you don’t know how terrible it is to be with the super‑exciting crazy people,and you will feel like you missed out. (Note: After you are done dating people who are bad for you, here is how to pick a husband, and here’s how to pick a wife.)
4. Try to look way more together than you are.
One of the people I dated that I shouldn’t have dated was someone who hired me. In case you’re wondering just how messed up it was, I had to withhold sex to get a job. One we came to an agreement, I learned really quickly and rose fast in the Internet world.
By 28, I was running companies and feeling a little awkward about it, especially because I still hadn’t learned how to manage my money. So I was making a ton, but I didn’t have a ton.
My board hired an executive coach to help me look more mature, and one of the things I did was buy grown-up diamond earrings, but they were fake. So in an all‑company meeting when someone pointed out that I lost one of my earrings, I made a big deal about it, like I lost my expensive diamond earring, and made everybody look for it.
We never found it, but someone told me, “You shouldn’t buy real diamonds anyway. You should have bought fake ones. Then you don’t have to worry about losing them.” Almost everyone wears fake diamond earrings because on your ear, people can’t see a difference.
That’s when I realised that I didn’t have to pretend to be pulled together. That being pulled together is relative, and I was doing much better than I realised. I didn’t need to fake it. I started doing better when I was more comfortable with myself. But you have to try faking it because faking it seems so nice and easy that you should get past it when you’re young.
5. Ignore siblings.
It’s really hard to stay in touch with your siblings when you’re struggling in your 20s. Most people in their 20s don’t know who they are or where they’re going, and it’s a time when you’re trying to separate from family rather than connect.
I grew up with a brother and did almost everything with him until our 20s when we pretty much stopped talking. It wasn’t planned. It just happened. It seemed at the time like a really sad result of fear or financial ruin or messed‑up parenting. Now I see it as natural for gaining my independence.
But keep in mind the 70‑year study of Harvard undergraduates to determine what really makes people happy. The study came up with almost nothing. There is nothing that they can show that makes a happy life, not even going to Harvard as an undergrad, except for one thing. If you’re friends with your siblings in your 40s, you’ll be happy from your 40s until you die.
Now, if we could just figure out how to be happy for the 20 years after you graduate. The Harvard Study doesn’t provide data for that, but other studies do, and the bottom line is that you should let yourself make mistakes, because the right path for a twentysomething is a tricky mix of intention and exploration and no one can move forward without making mistakes along the way.
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