My friend told me this week that lots of people want house sitters for their house in the Hamptons during the winter. He told me how one woman did it and was lonely as hell. She had no friends, no young people out there and it was freezing cold. Sure there are plenty of big, empty, gorgeous houses that will you pay you a minimal amount to live in highly-desired Hamptons for free. But if it’s freezing cold then who cares? You will be cold, lonely, and paid very little. Getting paid to be bored is the worst thing in my book.

 

I don’t know what to do for work these days. As everyone knows it doesn’t pay to be a writer or artist or blogger in a capitalist society. Not until you’re famous anyways. Meanwhile, thanks to Craigslist, and because I don’t want to be tied down to a desk job and a boss and so I can up and travel whenever I’m ready, I’m looking at random jobs like:

 

Giving a massage to a ‘professional’ older gentleman and you must be a dancer.

Write several articles for a new blog site for no pay.

Model in bra and panties for no pay. But you get photos.

Be a phone sex operator—sorry, phone sex actress—for $15/hr.

Be a live-in housekeeper, cook, and dress sexy for free rent. And free leering.

Dance in a bikini bar. No topless.

Dance topless, lap dances, no nudity. “MAKE HUNDREDS more than people make in 40 hours!”

 

No wonder I want to climb back into my cave of denial.

 

Money is a funny thing. It makes people stop talking with family members, do things that make them miserable. People will lord it over their lovers, exes, children. Some people are really good with managing it, making it; others are only good at spending it. A friend told me that in his exploration of “sugar daddy” sites that the “sugar babies” were demanding regular salaries. There are umpteenth books on how to make money doing what you love, what mindset you need to be in to do so.

 

I certainly don’t profess to have the answers. I did attend an inspiring talk with James Altucher and Jerry Colonna recently about entrepreneurship, but really on how to pick yourself up when you’re at the lowest of lows. It was a big wake-up call for me in terms of figuring out how to make money from blogging and what to do meanwhile. I still don’t know what I’m doing, but I know I need to start doing something.

 

I also got some investment ideas and an investment company suggestion from a well-versed financial investment friend. So I will put my savings to better use next time I make back the thousands that I ate through these last several months.

 

I see my friend work one hour a day. His friend works 6. My dad works 10. While my mom frets for 8 about the job she doesn’t have.

 

People choose very different lifestyles based on money, their relationship with security, their level of fear and tolerance for risk. I never cared about making money until I turned 29 a few years ago, always equated security with being trapped, am scared to try new things but do it anyway, and believe life is not worth living if you don’t take risks. That makes me do things like move from Boston to Hawaii without knowing a soul, taking on various odd jobs, and finally landing in waitressing and cocktailing in various bars and clubs so I was free to surf during the day—my topmost priority. Then moving to NYC and saved up the most money I’ve ever saved because I ended up in a couple and he was very generous. But then we both quit our jobs to work on our company. Then we broke up. And now my savings is practically gone and I need to wake up and start selling my soul for money by the hour but it’s been so long I’ve been dragging my feet. People wish me TGIF when I don’t know what day of the week it is for god’s sakes.

 

Meanwhile I’ve found the two loves of my life—writing and surfing— and I have no idea how to easily make money from these two passions. And meanwhile trying to remind myself “the joy is in the getting there” as Barbara Corcoran says.

 

Questions: Do you love what you do for work? What would you happily do even if you weren’t paid to do it?

 

Related Links:

Manifesto for Young Asian Women is Finally on Sale!

Zhang Ziyi Can Have Sex and Get Paid from Whomever She Wants

Why Do People ‘Settle’ When They Settle Down?