8 Lessons about money I learned from my family

When I was growing up, we had stuffed lions from Harris Bank. We had enough Hubert Harris lions to make a whole zoo.  The lions made sense to me, because I thought of the bank as a warm and fuzzy place.

Really, to understand what I’m talking about, I need to tell you about money in my family. And what I learned about money from living the life of a rich kid

1. Big money comes from areas of big chaos.
The money started coming to my family when my great-grandpa got a law degree in the 1920s in Chicago. He didn’t have any clients, so he hung out at the jail, looking for people who needed a lawyer. It turned out that the only people who landed in jail who could reliably pay for a lawyer’s help were prostitutes.

My great-grandpa did a good job representing them, and consequently, he met Al Capone, who was the money behind the prostitutes. Soon my great-grandpa became Al Capone’s lawyer.

2. You can buy luxury but not family.
As you can imagine, there was a lot of money to be made. My great-grandparents did what rich people did in Chicago at the time: They bought a big house in Evanston, IL and they hired Black people to serve them.

If you think story in The Help was a only southern thing, I can assure you that the same stuff was going on in the Chicago area.

Sula was five when she became a servant to my grandma, who was also five. It was a fine line between servant and playmate, but Sula was Black and her mom was hired help. Sula worked for my grandma for her whole life. My grandma, who slept on ironed sheets her whole life, always said that Sula was like family.

I always believed her, until I went to college and realized that other kids did not have a Black laundress who only came into the house via the back door. I also realized that you cannot pay someone to be family.

3. It’s difficult to have both high moral ground and high income.
My grandma married a guy who was soft-spoken and smart enough to get into University of Chicago even when there were quotas at universities to keep the Jewish population low.

It makes sense that if your dad is a lawyer for the mob, you’d react by marrying someone who is a stickler for morality.  But of course, my grandpa was no match for my great-grandpa, so he called the shots.

4. The people with money control the shots. For people who want the money.
This became very important when my dad went to graduate school. He wanted to get a PhD in history. My great-grandfather wanted him to become a lawyer. “Just apply!” he told my dad. So, reluctantly, my dad applied to law school and got into Harvard.

“No one turns down Harvard law!” my great-grandfather told my dad. Everyone in the family repeated that. And my dad went to law school.

He was not a good lawyer. Which, maybe, is the genesis of my obsessive writing about how you shouldn’t go to law school if you can’t market yourself to potential clients.

5. Lots of money means lots of false relationships.
The biggest — and maybe only — client my dad landed was my mom. She was in college with him. On scholarship. Her parents were both invalids and she knew it was a matter of survival to marry someone rich. She would tell you that she loved my dad.

Unfortunately they saved all their love letters in a box, to give to one of their kids one day. The love letters are a documentary of what it looks like to marry for money. My mom is the hot, popular girl who is too much for my dad to keep up with. My dad is the annoying social outcast she can’t stand. He grovels, she pushes him away.

There is nothing in the love letter box about what makes them ever decide to get married. So it is an easy leap to think my mom had a financial issue at stake and my dad had no social IQ to know the difference.

6. Rich people are never happy just being rich. They want to look smart.
Harvard was really important to my great-grandpa because the history of my family is, perhaps, the struggle to look classy when all your money comes from the mob. To this end, my great-grandfather subscribed to the Book-of-the-Month club.  If you could buy learning, my great-grandpa would have done that. The library in the Evanston house was huge and well-stocked.

The book collection became mythic in the family. Who would inherit it? That was the prize. Forget the museum-quality, yellow-glazed porcelain imported on ocean liners between the wars. People wanted the books.

My dad got the books. After all, he got the law degree. The books were stored with the dust jackets in a separate box. The books were all first editions—first edition Hemingway, Steinbeck, Wharton. The books were in pristine condition, of course, since no one had ever read them.

The day my dad went to go collect his reward for doing what my great-grandpa told him, we realized that no one knew where the dust jackets were. The value of the books was gone: it’s all in the dust jacket.

7. The money never lasts as long as you think it will.
So my dad gave the books to me, since I’m the only person in the family who reads fiction. I shipped the boxes to my apartment in LA. I found, underneath Finnegan’s Wake and Tender is the Night, a collection of pornography.

Not smutty, cheap porn, but famous, specially-bound books like Lady Chatterley’s Lover illustrated by Rockwell Kent.

I sold the books to a used book dealer. People always ask me how I supported myself while I was trying to get on the professional beach volleyball tour. Now you know how.

8. Stability and sanity make better memories than luxurious excess.
The whole time my brother and I were growing up, we heard about The Trust Fund. It was where all the money came from. It was what all the family meetings were about. It was why my parents could buy overpriced 70s art and a BMW E21—they didn’t have to save for our college. “The trust fund is paying for it.”

My brother got a PhD in economics. Surely my great-grandfather would have favored law school again. But he was dead. When I told my brother that Harris Bank was sponsoring a post on my blog, he wrote to me, “I love thinking about life as a rich kid back in the days of interest rate regulation and no interstate banking. You know, I really thought that every kid walked into a bank and was greeted by a private banker holding a stuffed lion.”

We had a lot of lions. We had a lot of mayhem. The family seemed to be in constant turmoil over money, and who was getting it and who had it, and how to get more. But everything was calm at Harris. The bankers were sane. There was never screaming about money at Harris. It was safe there.

For a while I thought my memories of Harris were so nice because it was the only place my parents couldn’t bite each other’s heads off. After all, who wants to be removed from the trust?

But as I get older, I realize that our Harris bankers (believe me when I tell you that my family had a bunch) were a calming, dependable force for our family. My family needed outside help to think through money issues in a rational way. Harris Trust provided that.

And those lions. Which, I noticed are selling for $100 each on eBay. I could have never predicted that the only money from the trust that would trickle down to me as an adult would be in the form of a stuffed Harris lion.

38 replies
  1. Mara
    Mara says:

    I had a real “moment” when I saw that picture. I had one (only one) of those lions. I wish I had kept it!

    • Ian
      Ian says:

      exactly the same for me. i’d forgotten i’d had a Hubert until i saw that photo. it’s possible he’s still in the attic at my Mom’s house. must have a look.

      (and i was born at Evanston Hospital.)

  2. Harriet May
    Harriet May says:

    My dad used to be a Wall Street banker, and one year he made a million dollars. He didn’t tell my mom. He stockpiled it, and a few years later used it to start his own company. My mom always wanted a big house and a cleaner and fancy vacations. But not my dad. When my dad left Wall Street my mom was devastated, because she was used to the income. We had nice things when I was growing up in the New Jersey suburbs, but I don’t think we had excess. I think part of it too was that my dad came from a colonial family in Kenya, who through generations had lost a lot of money (through poor financial decisions and laziness) and he knew that money is fleeting. My great-uncle, Hilary Hook, was even the subject of a BBC documentary, ‘Home from the Hill,’ which detailed his return to England after spending a lifetime in Kenya and India being waited on hand and foot. One of the most poignant scenes is one in which he is trying to cook himself baked beans– but he has never used a can-opener before.

    • KS
      KS says:

      Harriet, I loved that documentary; it was such a poignant portrait of those colonial British men. I read somewhere that it’s Simon Pegg’s favourite documentary film. The bit with the baked beans was heartbreaking. You would enjoy Spike Milligan’s autobiographies about his childhood in India and his family’s struggles when they returned to the UK, I think.

  3. Conqueror
    Conqueror says:

    All your posts are valuable, Penelope, this one especially. I grew up in a family that met its needs, but never had money to spare. Later I became intimate with people “from money,” and was dismayed by how miserable they were. Money was their every breath, and they seemed terrified of having to work for it. Somerset Maugham summed it up nicely:

    “I saw that Mrs. Strickland had forgotten that she had ever done anything so disgraceful as to work for her living. She had the true instinct of the nice woman that it is only really decent for her to live on other people’s money.”

    — W. Somerset Maugham, The Moon and Sixpence

  4. Becky
    Becky says:

    I’m endlessly fascinated by the different effects money has on people and relationships. Thank you for telling this story.

  5. Simone
    Simone says:

    This is why I read your blog, no matter what my opinion on the topic, you never cease to amaze me with your writing. And as a black woman from Chicago who now lives in NYC, this had so many relevant points for me.

    Starting with The Help – as you know many in the black community were really conflicted about this movie. Some questioned the significance of Hollywood putting this out, especially, when we finally have a Black Family in the White House (as leaders of the Free World, no less, and not “the help”.

    Some said it would show how far we’ve come but as a New Yorker sitting at Starbucks, as I’m typing this, watching the parade of Black nannies go by on 59th and Broadway, I have to wonder just how far we’ve come. I cannot tell you the number of meetings my friends and I have been at where we’ve been asked to get drinks or store coats, even as we’re swagged in Gucci and Prada from head to toe (sigh). Looking ultra-Michelle O (hair boobed, pressed and relaxed), confident and strong with our Ivy League stamp and Harvard accents and it’s still not enough.

    I also love the reference to Chicago, the 1920’s, and Al Capone which makes my beloved Chicago all the more legendary. I also find it fascinating how people, especially white people, made their money. i.e. the Bushes, the Kennedys…

    Most importantly, I think this post shows why you are very astute and beyond qualified to make the statements you’ve made (“the blueprint for women” comes to mind). Your not just pulling this stuff out of your ass, its based on real life/personal experience.

    Please don’t ever stop being you which is why all your haters can’t stay off your blog – they only wish they could be as original and brilliant.

    • Penelope Trunk
      Penelope Trunk says:

      Thanks so much for the nice comment, Simone. But also, I really appreciate hearing your perspective on being black (and decked out in Gucci) in today’s world.


  6. Helen W
    Helen W says:

    A lot of lessons here. The rich do not have it any better when it comes right down to it, do they? Once you have the roof, the food, and enough to clothe yourself and your family, that is really all anyone needs. Well, I may just add to that list a vacation away once a year, even if it is just driving 2 hours away so that you can escape work and chores for a week. I believe that being able to look forward to something is key to a happy life.

  7. Scott
    Scott says:

    There is a well known Urban Legend about Al Capone’s Lawyer, “Fast” Eddie. Eddie’s son was “Butch” O’Hare – a brave naval air pilot shot down and memorialized in the naming of Chicago’s O’Hare Airport.

    Penelope dispels that myth! Intriguing and entertaining tale. See:


    • Doug
      Doug says:

      I don’t think Penelope ever said that her great-grandfather was Easy Eddie. I think she just mentioned that he was one of Capone’s lawyers.

      Penelope, care to clarify?

  8. Lisa
    Lisa says:

    Ah, Penelope, my family’s bank was IBJ Schroder. My 2nd cousin was my trust officer. I remember how it felt to take that Wall Street elevator up to the 12th floor, the swoosh of the doors opening, the color of the carpets, the light from large windows overlooking salt water.

    It’s tax time. I’ve been mulling over a post about never doing my own taxes. I suppose now I will have to quote you. All for the best.

  9. Leah
    Leah says:

    I wish more people would speak honestly about issues that arise growing up in a wealthy family.

    It’s always okay to talk about being poor. I hate that it’s NEVER okay to talk about being rich, unless you’re on a reality TV show.

    • karelys
      karelys says:

      or unless you say you were miserable in direct relation to the money. I find that stupid.

      Some people are really happy. Some problems are augmented by money but some families would have similar problems without the money!

  10. Beverly Farmer Price
    Beverly Farmer Price says:

    My grandfather was a wealthy landowner who lost nearly everything in the stock market crash – because he’d mortgaged nearly all his land and invested in stocks when the market was “bubbly” in the late 1920s. I think all my uncles and cousins “inherited” from him was greed and a fascination with chasing “bubbles.” They all stole from and cheated each other over every remaining penny of my grandfather’s estate, while ostracizing my father because he didn’t inherit the greed gene. Makes for a lonely, fragmented family memory.

  11. Tommi
    Tommi says:

    Coolest beginning & first lesson ever from you. I didn’t get further yet, just had to comment :)

    You’ve hooked me before with your writing but never worse than right now.

  12. karelys
    karelys says:

    Last night I had one of those moments when I feel really rich.

    Maybe it’s the peace. Maybe it’s the thought that I don’t need anymore or even want anymore.

    My husband and I, together, earn $49920/year.

    We are buying a small house. We have old cars. We have a big tv (big for me). We eat out often.

    Half my paycheck is deposited in the savings account.

    We have life insurance and health insurance.

    Sometimes I have moments of worry. That if something goes wrong everything falls apart.

    But last night I took a bath and since I am pregnant I got super puffy from water retention. I only knew because he brought it up. Which made me laugh inside.

    I got out of the bath smelling like the expensive (to me) Burt’s Bees shower gel thing. And I put some body oil that I bought at a fancy spa I visit once in a while to control frizz. The fan was running and it felt so good.

    All our furniture is borrowed, given, broken, breaking, ugly. But it’s a lot lot lot more than what I had growing up in Mexico. And I want to be rich one day so I can afford to have an awesome life with my kids.

    But for right now, I feel so rich. Because I don’t need or want anything more.

    • Sharon
      Sharon says:

      The water retention you’re experiencing is not from taking a bath but from eating out a lot. Most restaurant foods (even though it may not taste like it) are full of sodium/salt. Especially because you’re pregnant you should prepare most of your meals – that’s a sign a real wealth too.

      • karelys
        karelys says:

        It was from taking a bath though because even though I eat at restaurants once in a while it’s the carb and sodium ladden kind.

        The water retention was evident after the 20 minute bath.

        Otherwise I’d be retaining water every day not just puff up when I get in the tub.

        I cook at home most of the time but sometimes it’s super nice to grab a salad somewhere and not have to clean up at home. You know?

        also, the taco truck lady does the same thing I do at home but I don’t have to clean up :)

  13. dgodfrey
    dgodfrey says:

    Penelope – what has given you stability and sanity in your life? Can you find that again (for the first time) and cling to it? Your abuse and divorce and heartache and loneliness take my breath away. I know you’re sharing in order to be a voice for the bruised reeds of the world, and that is brave and lovely. I hope you find what will be a balm for you. YOU.

  14. Gayle
    Gayle says:

    Really enjoyed this post. I too remember the Harris bank lion…but not because we were monied…far from it…but also explains the mixed feelings I have about having it and getting it.

    Straight out of h.s., I went to college in Lake Forest. I got to know quite a number of people with money–new and old. Some of them were actually decent people (though can we ever know what lies beyond the surface of people’s lives). Some were assholes; these were often the new money folks…or the kids of old money without having to do very much or account for their lives in any appreciable way.

    I agree that many, many monied folks are unhappy…alas money in and of itself doesn’t buy you happiness.

    Then again I could say that about the “poor” or less monied people I knew and grew up with.

  15. Deila
    Deila says:

    I loved this post and a peek into a family history. Thanks for sharing your bear story. My dad made money and lost it in his lifetime, he was sad he had nothing to pass on to us kids.

  16. Irving Podolsky
    Irving Podolsky says:

    How could I not chime in with another, “I loved this story, Penelope!” And I did!

    Not much to add, except that my parents both came from poor Jewish families who had rich cousins who stayed rich because they didn’t share their wealth. In my house, the word “Money” was code for “Not Enough,” and we didn’t have to say it aloud. The pessimistic anxiety of LACK was always in the air and I couldn’t help taking it on as a young adult and bringing it into my future.

    You just can’t get rich if you feel poor. That’s a proven metaphysical fact.

    Knowing this, I’m still frugal and conservative as hell…too much so…and I’ll never get “rich” behaving that way. (Rich in my terms is never having to worry about money or how much something costs. Yet, by the rest of the world’s standards, I AM rich.)

    Am I materialistic?

    Yes and no. I don’t need a lot but what I have should be of quality. Is that too much to want?

    Why do I need to even ask that?
    Why do I feel guilty desiring money and power?
    Why can’t I get past my own resistance so I can get it?
    (I can answer all of that. Doesn’t help.)


  17. lynne whiteside
    lynne whiteside says:

    I never realized we were border-line middle class. but once my dad said that if you took a nickel out of mom’s purse, the buffalo shit.

    her frugalness has ensured that all three kids will inherit at least more than we have now. and I’m thankful for that! it took a long time to realize is my relationship with money is very conflicted, save/spend/save/spend. all I really need is what I have right now at this moment, a roof, food, a wonderful dog, but, alas, no one to cuddle with! some things have to wait.

  18. Bernard
    Bernard says:

    The biggest lesson I learnt from my family is to save atleast 20% of my annual income and convert into assets. This way one can overtime worry about money less due to the assets which have been built as compared to living from salary to salary… and hence it helps focus on many other things in life beyond money.

  19. Ellen Chamberlin
    Ellen Chamberlin says:

    but so many of your posts are about how to make money and with ALL due respect, it seems you strive for a less chaotic (more sane) family life. this post is confusing. i know you realize the importance of both. there are lots of false relationships regardless of money.

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