5 Mistakes new grads should make

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 at the 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 ten years running our family children’s bookstore was worth a lot more than I realized.

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 realize 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 earings, 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 realized 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 realized. 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 twenty 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.

39 replies
  1. CJ
    CJ says:

    It is really refreshing to find a discussion on the Harvard study, someplace other than in the human health realm. For all my obsession with nutrition and global health, I regularly discuss this/these studies. Social connections, joy, and the brighter side view are the most cited advice given by the healthy elderly. Sardinians are the masters at telling us over and over when interviewed about living long and living fulfilled: eat well and love strongly. They have an exceptional dedication to family close knit ness and live very long active lives. Americans often sacrifice their family time for career climbing. We pay for it with our health.

  2. Lindsey
    Lindsey says:

    Right on. I’d add: #6. Have some confidence while making these mistakes. Especially when many of your friends took more traditional paths and have reasonable jobs with decent salaries, a steady boyfriend, and a cute apartment. That’s okay, but I think it’s okay to do these other, more scary things and learn from them.

  3. Nicole
    Nicole says:

    Reading your blog posts is like falling down the rabbit hole and I love it, each and every time!

  4. Laura
    Laura says:

    WHERE were you 15 years ago when I graduated? My husband and I did the exact opposite of all of this advice and we are now poor and tired because of our decisions! We have a good marriage and I home school the kids, but I wish I had a time machine so we could get your career counseling 15 years ago.

  5. Ru
    Ru says:

    So much pressure right around 22 when you graduate to make the right choices. Then at 25, i realise nothing could be worse if you dont start making choices soon to try something new. The possibility of failing becomes less daunting. Then at 27, actively run towards experiments even if you know they are failures. because you only have 3 more years to hit 30 to learn as much you can about yourself. I hope once i make enough mistakes in life, theres nothing left but to move upwards

  6. Elizabeth
    Elizabeth says:

    Rules were made to be broken, whatever your age.
    This doesn’t stop at 30, or 40.
    I think it becomes even more important the older you get – because it gets harder. There’s more at stake.

    Every career/discipline has rules. Even the ‘creative’ fields which can seem free to outsiders – but they’re not.

    The rules have only as much power as you give them.

  7. Henry
    Henry says:

    “Quiz me. I know every single children’s book published from 1975 to 1990 and the publisher’s imprint”

    How about one that I loved reading to my kids:
    But Not the Hippopotamus

  8. Jim
    Jim says:

    Andrew Henry’s Meadow
    The Adventures of Mole and Troll

    These are books I loved as a boy in the 70s but that nobody I ask has ever heard of. Can you name the imprints? I actually remember on the former but not on the latter.

  9. Johanna
    Johanna says:

    This is a great post. While I don’t agree with all of the advice given, I certainly appreciate that post-graduation is a great time to make some reckless decisions and experiment with how much you can get away with in the real world.

  10. Mark W.
    Mark W. says:

    This post and the 70 year-old Harvard study make me wonder if there has ever been a “happiness” study done on college graduates who take a job relatively close to where they went to school and grew up as opposed to those people who move a great distance upon their graduation for their new job. I was the latter as I had a job lined up on the other side of the country. Everything was an adventure and moving was no exception. However, I found out I tired of having to take a significant amount of vacation time and the expense that went along with it to see my parents and siblings. I always enjoyed visiting with them but a weekend or long weekend via car would have been easier and worked out better.

  11. Anoel
    Anoel says:

    Harvard and reports and whatnot can say whatever they’d like. There is no way in hell I want to be in contact with my brother whether I’m 25, 35, 45 or above. Some of us just get unlucky and get horrible siblings. I’ll choose my own siblings and family, thank you very much.

    On the other hand I do believe close relationships are very important to happiness.

    • Penelope Trunk
      Penelope Trunk says:

      I’ve actually spent a lot of time thinking about why this is true – why does close relationships with siblings at 40 mean you will be happy?

      I have concluded that in order to have that relationship it means that
      1. You have to work at it. So you don’t just give lip service to valuing relationships, but you actually take steps to live a life according to that value.
      2. You have to be forgiving and overlook a lot. There is not one sibling relationship in the world where the sibling has not done something where you could say, screw you, I don’t want to talk with you again. The people who are close to their siblings after that many years have forgiving a bazillion transgressions. And I think people who are forgiving are happier people.
      3. It takes a certain amount of stability and reliability to maintain relationships through so many stages of life. And people who can create that consistency within the context of relationships with siblings can probably do it with other people, too.

      This doesn’t mean that if you don’t have close relationships with siblings at age 40 you will be unhappy. It just means that statistically, you’re in great shape if you do have those relationships at age 40.


  12. Sarah m
    Sarah m says:

    There are so many little pieces of your childhood that are so funny to me, in the sense that it’s out of left field. Family run children’s bookstore? What? I would have never guessed.

    However, this looming 20s & 30s adolescence is insane. I would never let my kids move back in with me unless they had a medical condition and needed care. It’s called living in poverty to see what actually matters to you, and then starting to get a handle on your money to put it towards those things. So what if you have to eat PB&J or live in a studio for years. That will teach anyone how to deal with finances and cut the crap out of their budget.

    Sarah M

  13. Munch
    Munch says:

    “I had to withhold sex to get a job”

    Male executive “I had to give her a job to get in her pants”

    • Penelope Trunk
      Penelope Trunk says:

      I love this comment! I never once thought of it this way. But when I read it, it makes perfect sense!


  14. Bill
    Bill says:

    I am about two weeks into my post graduate life and find this post to be a welcome relief from the constant stress I am have been encountering the last few weeks. I have always wanted to almost to just let go and see what my true passions are free of others opinions what I should be doing. Hopefully I will begin to find my true passion soon!

  15. Dana
    Dana says:

    I’m looking for a childrens book set, maybe, in spain or italy. It is about a little boy who loses his small dog but as he goes from town to town asking about it, the people think he is talking about a wolf. May be pre 1975, though.

  16. Nad
    Nad says:

    Gosh I love this article. You’ve basically summarized my whole life. I’m turning 30 in a few months – and have done EVERYTHING you’ve done and written about in this post. It’s strange but I welcome the relief of knowing I’m not the only one so crazy to have dated my boss, a drug addict, and some other types I don’t care to mention.

    I feel so much less alone now!

    I’ve now discovered that there is really nothing more I want to do with my life but become a writer because I want to make messed up people like me feel understood and calm about their choices – sort of like you.

    I’m slowly getting there – trying to build up the courage to share my life. You’re so brave.


  17. Heather Sanders
    Heather Sanders says:

    My path was so much different (and considerably calmer), but I did try on a crazy amount of jobs, which was good for me. I have to disagree about dating all sorts of nut jobs before marrying. I married right out of college at age 22. Best decision ever. Then again, stability is pretty important to me, so marrying freed me to feel secure to make other mistakes.

  18. Carolyn Cho
    Carolyn Cho says:

    Hi Penelope — I am usually a fan of your posts, and I understand the connection between points number 1 to 4 on this post; they all share the thread of experimenting, and through the highs and lows that come with that, becoming more comfortable with yourself.

    I am not sure point 5 fits in with the rest of that. The sudden tip to “avoid siblings” seems to come out of nowhere. I suppose you could make the argument that it fits in with the rest of the tips because it’s forcing you out of your comfort zone, away from comfortable relationships, but that connection seems weak at best.

    Experimenting and growing does not necessarily require severing family relationships, even temporarily.

    • Robin K
      Robin K says:

      Severing is a strong word, I think PT is suggesting a bit of distance is a healthy thing.

      It’s difficult to make monumental personal changes with the expectations and pressure of your family hanging over your head. Family and especially siblings can be a powerfully limiting and constraining force. It’s biological; we’re tribal by nature. Our tribes pressure us to conform, but conformity doesn’t help us become independent thinkers.

      I found I didn’t really get to know myself and experience real personal transformation until I had distance between my sister and me.

  19. Trisha Lotzer, JD
    Trisha Lotzer, JD says:

    As a happy, successful business owner in her early 40s I agree with what you say about not going to get out of grad school to avoid tough choices. And moving home would allow people to save money.

    But people should follow their passion and do what they love and marry for love. Then the money will follow but it rarely works the other way around.

    • Robin K
      Robin K says:

      I know a lot of couples who married for love but are constantly torn between work and home life because their partners have needs that aren’t complementary to their own in those realms. For example, my friend wants to be home with her kids, at least part-time, but has to be the primary breadwinner because her husband is not (personality wise) capable of holding down a full-time permanent job (he freelances, but it’s not always consistent work). As a result, she is not happy with her life on whole. And she feels trapped.

      Love is nice, but other factors are just as important.

  20. Sam
    Sam says:

    Penelope- what should you do when you’ve been out of school for a couple of years, apply for a job that would be a good career move, and in the initial screening call the HR person says the job range is less than what you currently make? Is there room to negotiate when they clearly state the salary range before the interview to weed out people who aren’t okay with that range?

  21. Sallie Borrink
    Sallie Borrink says:

    Here’s a book set I would love to find from my elementary school days.

    It was a Bicentennial set (so circa 1976) in red, white and blue. There was a boxed case for the books and about 6-8 books. Each one was about a different prominent American from the Revolutionary War era. I think they were books about the people when they were children (Betsy Ross, George Washington, etc.). I’ve looked and looked and cannot find anyone who remembers these. Do these ring a bell at all?

  22. Mominvermont
    Mominvermont says:

    Happiness: If you’re friends with your siblings in your 40’s, you’ll live happily ever after.

    One more reason to homeschool! Homeschooling fosters good relationships because if you don’t take the time to work on your social skills with your family, y’all will drive each other nuts.

  23. Rick R
    Rick R says:

    This is great advice! So many people discuss what positive things you should do after you graduate, this is the complete opposite and I feel you would learn so much more from this!

  24. Alexandra
    Alexandra says:

    This post is absolutely hilarious. Im glad I came across your blog, a pleasant surprise! I am a recent grad of a few years, and don’t necessarily follow this blueprint, however i’m beginning to think maybe I should so I get it out of the way! Cant wait to read your other posts! -Alex

  25. Elena @ Giveaways
    Elena @ Giveaways says:

    I think the worst thing you can do as a graduate is not having a plan. Only 10-15% of graduates have a plan for after they graduate, and, according statistics, those 10-15% who do, make more money than the rest of 85% taken together.
    So, make a plan – get on the right track with what you want to do in life. Several years of college is enough time to think about it and get prepared. Is that right?

  26. Jay
    Jay says:

    just ran into your blog and im in a place where im 27, have a 2 yr old son, and in fork in my career. ive been struggling with where im at and your posts hold so much truth for me. it is so enlightening and refreshing. i absolutely LOVE it. i feel like u understand me! hahah. <3 <3 <3

  27. Tony H
    Tony H says:

    I have to wholeheartedly disagree with the one about ignoring siblings. Staying touch with those who know you best is one of the best ways to stay grounded. Yes, they can sometimes limit you, as being the “baby in the family” or other family roles, but I believe ultimately deep meaningful relationships are a key to someones success. I lost my sister in a car accident 3 years ago, and seriously regret not having stayed in touch more when we were in our 20’s.

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