Money Matters

Amongst taboo topics: money.

Listening to Oliver wonder why we shouldn’t talk about our savings and earnings I understand his confusion.

I liken it to gender and race, explaining that we shouldn’t categorize people based on facts that they can’t control. He rebuts that we can control how much money we have.

I answer that like everything else that is complicated.

I mean it is public record that our house is on the market for 1.5 ish million. Like many things I share more about my personal finances than most polite people. So here it is for you. Second to food money is the most complicated relationship of my life. In part I believe because we don’t talk about it enough.

I grew up in Newton, Mass. When I was really really little we lived in a garage in Sumerville nicknamed Slumerville and/or scumerville. Now Sumerville is the Park slope of Cambridge which is the Brooklyn of Boston. If you follow. Then it was scummy.

My father was savvy about real estate and bought and managed several multi families (one of which had our home sweet garage in the back.) while he ‘worked’ as a sculptor. Eventually in his real estate scoutings he came across a Newton Victorian with a decaying carriage house (studio!) and moved us there. I don’t know if it had been abandoned, or just maltreated, but there was super cost effective renovation going on, and when we went to visit the house my only questions was where the workers would sleep.

So between real estate and other investments my family lived a pretty close approximation to an upper middle class life. We rarely ate out, drove mid level cars, and vacationed at a summer house reminiscent of our garage, but I lived in Newton…so that meant brand name jeans, cabbage patch kids,  a large selection of tween luxuries. I even had my own phone line.

When I was in eighth grade my grandmother died and left us money. I never knew exactly how much money, but she left a fair amount, like a millionish dollars to me in trust until I turned 35, and a bunch to my father.

From then on we were 1% ers before I knew the term. We built a large house on a lake in Newton, we flew at least business and often first class, and whatever my father wanted he bought. Now this made my mother uncomfortable, but he didn’t really factor that in.

He had odd tastes though, so he would buy sports cars, and art, and gold fingernails, and hired a full time personal assistant, ostensibly to help with his sculpting (and they were all artists themselves) but he used them to take out the garbage and buy him classic cokes. Between money, age, and non-conformist views he isolated himself on lake ave. Emerging to battle the sprinklers, gardeners and site seers who would walk up our drive thinking it couldn’t be a private home.

Amongst other questionable decisions that I championed at the time my father broke my grandmothers trust when I went to college, so I entered Brown with a credit card and a larger than average checking account. That worked out pretty well while I lived on campus. Sometimes I would foot the bill at a dinner, or buy my roommate a sweater but I spent within reason. This was the start of the time that I used money to help buy friends, a practice I am 99% over, but always fear will come back. I cringe as a write this, but the examples are myriad and embarrassing. For the most part I just made people uncomfortable, because my friends have never been the sort to want to be bought. It just took a while for me to recognize that.

Post college graduation I moved with my boyfriend to Brookline, the fancier version of Newton, and rented a nice apartment for above market rate. I had a job, it would turn out to be the most money I have ever earned, and had a paycheck and then whatever my money was earning. At the time my account was throwing off 40,000/ month. Per MONTH. So that year I lived like a mini version of Leo D, renting out all of Boston Billiards for my friends, writing BIG checks to local non profit, generally spending with no plan and no regard for the future.

We moved to Vermont where we couldn’t find an apartment that suited us, so I bought a house. Naturally. We were both unemployed. So we lived on my trust fund. I began working for the school system, got recruited to grad school and became a teacher. Around this time my dad got sick and died, I got married and divorced from my college boyfriend, and I became very depressed.

My self medication was shopping. Not only did I buy big ticket items like a second house (check out the view) 65 inch HD TV when there was not a single HD channel, but I shopped catalogues like it was my job. Between shopping, supporting our household while in grad school, and continuing to give to both Mass and VT non profits I was spending down my account. My father was dying, my mother was caring for him (not that I would have listened to them anyways.) My money manager worked out of the Twin Towers in NY. I was probably his lowest net worth client, and we had never put together a plan to disregard. So I did whatever, and didn’t open the statements.

For six years I earned a teacher’s salary which mostly was relevant because it gave me benefits.

Then I left teaching because I had opened the waiting room and needed to run it. Why did I open the waiting room? Because I bought the building (a good idea) and rehabbed it (could go either way) and wanted a nice bar to meet my second husband (no comment.) When I couldn’t find anyone locally to rent the space I imported friends of friends from Boston. They helped make a hip urban place. I had never worked in a restaurant and I owned it. They knew what they were doing and they operated it.

There was friction.

After the business break up I left teaching to run the restaurant/bar/music venue that I now owned. That went about as well you you would expect. I had an incredible staff, except the cocaine dealer and a few nut cases, and I proceeded to befriend them (not necessarily the best idea but I was 26 and lonely) I ran that venue the way I ran my life. Big bold ideas: health care for wait staff! weekly arts projects with visual and performance art! Local and organic without the prices to match!10% of sales to non profits! Fresh flowers! One of a kind artwork! Handcrafted tables, check presenters, blah blah blah. It was a joy that made money for lots of people around me. When I closed the doors I had lost $800,000.

So now I was down to much much less money, so naturally I went to work for non profits. I earned very little but established some great systems and events while also have time with my little little boys. The Strut fashion show was my idea. There are lots of others.

When I operated the waiting room I gave back through the business so some of that 800K took the place of my annual philanthropic giving. Now I was back to having to write those checks from my family account. I mean, the waiting room account was pretty much just funded by my family account anyways…but some things were going to have to change.

During the time I operated the business my mother bought a lake front lot in sheburne and steve and I rented the ranch house from her. This, along with the original gift from my grandmother, and the art collection from my father, is what has allowed me to maintain a higher than average quality of life even as I pump money into the local economy way beyond the ratios most people advise.

After I left the non profit world I found myself unemployed, with a house renovation sponsored by my mother. Steve made a really good for Vermont but not impressive for the whole world salary, and health care for the first time since teaching came from someone other than me, or whatever S Corp I was currently running.

It was around then that I took stock of my spending, and my family and made some big decisions.

1. I am currently spending money at a rate that we will never be able to afford this life.

2. Investing in local companies (which I had done 40x by then), buying local art, buying local food, and giving time and money to non profits were practices that I wanted to continue.

3. My actions show me that I don’t want to build traditional wealth the way lots of other people do.

4. I don’t want my mother to be supporting our life AT ALL.

So I was left with either scaling back to the right sized life, which would mean ceasing #2, and living much more modestly in every way. Or liquidating my one remaining asset. So I sold the art.

I have raised about 4 million from art sales. A full half of that went to the IRS. Don’t get me started/you are welcome. First I paid off the mortgage on my house, and had my mother sign it over to us. Then I bought two properties in Florida, one that could be considered an income property and the other a lovely little mistake. (Also currently on the market.)

Then we shopped for a house in Shelburbia. And although I continue to state that I could have would have gotten a smaller more modest house than we did we still cut the price in half and the carrying costs by 2/3. If that lake house had sold we would be able to maintain our lives at this level for a pretty long time. Currently though we have 4 properties with their associated property taxes, utilities and debt service. And despite win win apps, marble jar, Refresh Collections, and I’m sure there was at least one other venture in there, I continue to pay to work rather than get paid to work.

So I drew a line, kids need to have fully funded college accounts, and we need to have 1 million in the bank. A sort of symbolic symmetry that re-sets me to where I started Freshman year of college.

Despite paying to work lots and lots of my real estate investments have made money, and as crazy as my see saw of gain/lose gain/lose has been my average annual income comes in around the same as Steve’s not including any money my money makes.

I have used the pronoun “I” through this, because early in our relationship Steve and I established that outside of the college funds and the million dollar safety net everything else is mine to grow, use as angel funding, or toss down the drain. He cringes for sure when I tell him about each 80,000 check. However he lets it go, saying that he believes in me. Im not quite sure why given my track record, but it is nice to hear.

So there it is, my sordid money history. Which includes lots of lucky inheritances. And a more cavalier attitude than most. I wish there was a way to follow the money trail, and see some of the good that has come out of what are apparent losses. It hard to attribute full responsibility to any one of my investments or ventures, but there have been successes.

Events, places, relationships, art sales, etc.

The next chapter is pending. Hopefully I will post something later this week, my aim is to create a sustainable way to reinvest in our community, using one big initial investment (social venture endowment style.) In the mean time I have cancelled the catalogues, completed the college funds, and called the realtor. Three of the four properties are on the market. If you throw enough darts you will eventually hit the bulls eye.

So thats my story. At least so far. Oliver tuned out a long long time ago. He doesn’t have my demons, or my imagination. He saves with gusto. Leo on the other hand…

I’d like to hear in the comments:

1. Your complicated relationship with money.

2. How you talk to your kids about money

3. Whether any of my expenses or investments have effected your life. I’d LIKE to hear positively, but I will also listen to negatively.





Published by

Anna Palmer

Anna Rosenblum Palmer is a freelance writer based in Denver, CO. She writes about sex, parenting, cat pee, bi-polar disorder and the NFL; all things inextricably intertwined with her mental health. In her free time she teaches her boys creative swear words, seeks the last missing puzzle piece and thinks deeply about how she is not exercising. Her writing can be found on Babble,, Great Moments in Parenting, Ravishly, Good Men Project, Sammiches and Psych Meds, Playpen, Crazy Good Parent, and YourTango. She also does a fair amount of navel gazing on her own blog at

11 thoughts on “Money Matters”

  1. Well lady, there it is. I can tell you that I lived most of my life not giving a shit about money, making decisions like getting an Art degree. In my twenties I bounced checks, spent all I had and racked up 50,000 of credit card debt, Nat started a business with no funding or nest egg and we had to file for bankruptcy. I would have lost everything if not for my family helping us for the two years Nat was self employed. Now I am totally freaked about money to the point that I fret daily, check my bank balance daily, fret about what’s coming in and what needs to go out, so much so that I stayed at a job I hated, leaving my hopes and dreams behind for 11 years. So now is my first day, unemployed and child free and what am I worrying about?…. money. I told myself I was going into my studio to make art again, at least for a couple months, and now I’m checking Craigslist like a freak and wondering how I’ll buy groceries and school supplies… and it sucks because I’m 43 and it shouldn’t be this hard, and because I know I’m talented and in theory there are 1,000 ways I could make money, even lots of it, if the moons align…but so far they haven’t so here I struggle.

    1. I understand, and I want to apologize to you from our whole world. You have talent and vision like few others, and that should in some easy way turn into enough income to support you. Instead we have a disposable culture that needs a curated environment to feel good, but can’t identify it or value those that make such an environment. Ugh. Go make something.

  2. At 42, I am working on forgiving myself for the fact that I suck at money….and that it’s not entirely my fault. I grew up in a poor family – we moved (often) – following jobs, or relocating to be able to stay with family. When I was started high school, my family didn’t have a car. I was mortified to admit that we couldn’t afford one, so I told everyone that it was my parent’s grand experiment to live w/o one. The city buses stopped running at 9pm, so if I worked late (at my minimum wage retail job), my Dad would ride his bike to the mall and walk home with me (3-ish miles). The thing is, I have no idea WHY we were so poor – my parents never discussed money with us. I got my first credit card at 18, and bought a $69 bathing suit at Macy’s to celebrate. At 24, in the midst of a divorce from an abusive husband, I filed bankruptcy to allow me to continue to feed my 3 year old. Fast forward years – another marriage, another child, medical bills, a near-fatal car accident, a mortgage and the stuff of life – and the credit card bills piled high again. Fast forward (again) to last year – a second divorce, taking on the mortgage alone, supporting a teen, and trying to help out my daughter who is in university (student loans) – and I am ashamed and exhausted that I am behind on bills and often struggling to make ends meet. I have a great job. I am intelligent. I should have this figured out by now.

    Thank you for this refreshingly honest post.

    1. Life is expensive. Medical bills are expensive. Oliver was born 7 weeks early, he was our $100,000 baby. We were out of pocket tens of thousands of dollars, it would have bankrupted many many families who were doing nothing but welcoming their first child into the world. Divorce is expensive. College is expensive. Moves are expensive. Every little thing adds up. It’s hard to KNOW, let alone stay honest with ourselves about what we have and what we need, let alone have reserves for those car crashes. I had an entrepreneurial friend who said: cash is like oxygen. I always hated that line. Does that mean 3/4 of our country can’t breathe?
      And those of us that have cash…where is the expectation that we use it for the common good. I would say that not only is it not expected…but it is frowned upon. Building wealth the expectation. Donations, angel investing, starting social ventures, are viewed as impulsive if done outside of a tightly controlled ratio.

  3. Anna — what I respect most about you is that you create and invest in things that you’re passionate about. You pour your smarts, energy, creativity and wisdom into projects small and gigantic that bring things to life, help people and make the world a better place. In both “non-profit” and “for-profit” structures (in the legal sense of the word!) You help people in every way, and pay attention to the small details that make an important difference, from health to entertainment to beauty. (A few memories: Waiting Room brunch; 456 North St – got married, got our dog, and started my own business in that house; the view of the lake from your home (before and after); and much more)

    I also respect your honesty, and thank you for all of your blogs that help us just be brutally honest with ourselves, and each other. I learned when I had my second miscarriage that we have this veil of secrecy around some of the most important and raw life experiences. But why? Mourning alone was WAY worse than mourning with people. And when I started talking about it, I found many many people with shared experience. And we made it easier, just a bit, for each other.

    During an interview with a mega lottery winner I heard on NPR a few weeks ago, I learned that a crazy percentage of lottery winners actually go bankrupt. It’s not about what you have or don’t have, it’s how you develop skills and discipline to live your values within your means. The problem isn’t the money, it’s the lack of skill or discipline to manage it.

    As I read your blog, I see you reflecting on how you’re developing those skills, self-taught, maybe a little sink or swim, and learning as you go. You didn’t learn those skills from your parents because they didn’t have those skills or models to learn them from either. Your opportunity, more than any business, investment, or sale, is to teach your kids the skills and help them understand the language of money.

    Years ago you taught me about a 4 slotted piggy bank which I use for our kids, and have told SO MANY other people about (save, spend, donate and invest). I’ve used this tool to help my kids understand what THEY value, and the trade off when you apply money to that. Maybe a 50 cent toy is hugely valuable to them, whereas a $15 thing isn’t really worth it. Or maybe the one rare Pokemon card is totally worth it, even though it costs the same as 10 packs. There’s a translation between head, heart, wallet, and conventional wisdom. I think we all wrestle with what that balance is, because it’s the exception that they are all saying the same thing.

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