When I was a kid, there was money everywhere. My great grandpa was a lawyer for the Chicago mob in the 1920s, and today, my dad's generation is still living off that money. Sometimes I wonder if the key to being able to squash materialism is to have a lot of it as a kid. I'm not sure. But let me tell you this: I grew up with a laundress and a housekeeper and unlimited cash from a drawer in the dining room.

When I went to college my parents cut off my money. I think this might have been normal at the time. I remember crying. Really. Crying over the fact that I'd never be able to shop at Lord & Taylor. But it didn't take long for me to see that people don't wear Lord & Taylor skirts to class. In fact, I realized that most people don't wear Lord & Taylor skirts anywhere because some of those skirts could feed a family for a month.

1. Test the meaning of money by doing stuff that's scary.
One of the first things I did after college was sell three strings of pearls to get myself to Los Angeles. I was really scared when I did it, but in fact, the only time I missed those pearls was when my mom asked where they were.

When I was making a lot of money, I had great work clothes and a BMW (hey, I lived in LA), but that was about it, in terms of splurging. I kept an inexpensive apartment, and people used to tell me I was nuts to live there when I had so much money. They told me I was uncomfortable with success, and I worried they were right, but I stayed there. In hindsight, I realize it felt safe to live somewhere I could afford if my company went bankrupt. Which it did.

2. Put a bunch of stuff in storage to see what it's like.
When I moved from Los Angeles to New York City my husband and I rented a 500-square-foot apartment. We told ourselves we'd only be there for a year, until we got more settled in the city. So we put all our books in storage, most of our furniture, clothes that were not in season and everything we wouldn't be using in the next three or four months.

The only way I could put the stuff in storage was to tell myself I could go back and forth every week getting stuff I missed. We ended up staying there six years. We took almost nothing out of storage.

I quote Daniel Gilbert all the time about how we can adapt to anything. Gilbert says that we think some changes will be terrible – like losing a limb – but in fact we are great at adapting to circumstances that don't change. This is true of putting stuff in storage. You quickly learn to live without it.

3. Understand the concept of aspirational clutter. Get reality and throw stuff out.
When we had a baby, we thought we would move for sure, but 9/11 was too traumatic. It didn't feel like the right time to move. So we threw stuff out, and we learned a lot about how what you keep in your small apartment is a statement about your values.

So much of what we hold on to is what we wish we were using — objects that commemorate a life we aspire to but do not have. The six books we bought a year ago and haven't read, for example. We don't want to admit that we're not making time to read, so we save them. The treadmill is another object that is loaded because if you throw it out you're admitting to yourself that you're never going to use it. Keeping it, even unused, maintains your dream of getting into shape.

In fact, we had to think very hard about every single thing we let into the apartment, and we instituted a rule that if you brought something in, you had to take something out. Maybe other New Yorkers in small spaces had this rule, too, because there is always really good stuff left on doorsteps in New York City.

Then we had another baby. And that was it. With four people living in 500 square feet, I started having recurring dreams about living in a bigger space and I'd wake up to be disappointed that it was only a dream. I decided the small space was driving me crazy, and I started compiling research about where to move.

4. Know this: You could dump everything if you had to.
And then we got bed bugs. We didn't know that much about them but we captured a bug and checked it on the Internet. When I left the landlord a message to tell him we had bed bugs, our usually completely inaccessible landlord called me ten times in one day. I should have known we were in big trouble.

In fact, our whole building had bed bugs, and maybe the whole city. There is a lot written about bed bugs. There is an epidemic in the United States at all levels of the economic spectrum. (Our bed bug expert said that the worst clients he had were up and down Park Avenue because they felt they had been assaulted by the dirty underclass.)

Bed bugs bite you in your sleep. We had two kids under four years old, and I started staying up all night keeping the bugs off them. Finally the landlord paid for a hotel (about $300 a night in NYC) while we negotiated with him about what to do.

The bugs and their eggs could be in anything in the apartment made of fabric or wood. Here's how long the bugs can live without food: eighteen months. There is no way we could starve them. We had to poison them. And the only way to do that is to get them to come out of hiding and walk through the poison. The only thing they'll come out for is human blood.

How would they get human blood? We had to live in the apartment. What do people on Park Avenue do? The staff lives there while the family goes to the summer home or a hotel. What do the not-rich people do? Use themselves as bait. That's what our neighbors did.

We tried using ourselves as bait for one night, and every bug (by now there were forty or fifty a night) went for the kids. I developed near complete insomnia, always fearing that the kids were getting bitten as soon as I shut my eyes, even in broad daylight when the bugs are asleep.

The bed bug expert said that the most common thing he sees is that people move, but they won't give up their stuff, so they take the bedbugs with them. We had two kids bitten everywhere. We took no chances and we took with us only things that could be boiled in hot in water or thrown in a hot dryer – to ensure no bugs. We took from that apartment less than half of the size of a small U-Haul truck. We left almost everything.

5. Throwing stuff out is not wasteful.
In Madison, we started with just about nothing. Sort of like college kids. You think that throwing everything out is so costly and such a waste of money. But in fact it taught us how little we needed most of the stuff we had, which made us buy much less going forward.

While we have bought a lot since we got here, the years in New York City taught us about living in a small footprint (we still have one of the smallest two bedrooms around) and losing all our stuff to the bed bugs taught us that we didn't really need much after all.

People often ask me how was I able to switch careers so many times (professional volleyball, corporate marketing, entrepreneurship…) And how have I been able to do so many high risk things (for example take a 70% pay cut and start new as a freelance writer when I had my first baby and was supporting the family.) The answer is that I had very little to lose.

It's a cliché for a reason. If you have a very low-cost lifestyle and very few physical things that you treasure, you cannot really imagine a rug being pulled out from under you because you don't own that great a rug anyway.

People think that what's holding them back from taking risk is some big financial idea of stability and well being, but it's really fear of losing your comfortable material life, whatever that is. Mine is so spare that I can easily replace it, even if we got bed bugs again.

Which we won't. Because we had our new house treated before we moved in; even big risk takers draw the line somewhere.