Most stories of money and AIDS involve folks going broke trying to pay for meds. Not mine. Until testing positive in 1990, I’d led—or followed—a freewheeling life, unfettered by financial concerns. I come from a long line of entrepreneurs who relished the high risks of invention over the security of savings. Dad has gone bankrupt twice; now 70, he’s happy in his small rental apartment and low-maintenance life. At 96, Poppy throws his Social Security check on the green felt in Atlantic City every month. He can barely see and just manages to totter around, but when his walker hits the casino floor, he’s a new man.

In my youth, I embraced this state of mind and went wherever the day took me. I traveled the country by thumb, grew pot on a California mountaintop, performed Beatles songs in Mexican cafes and Dumpster-dove my way through New York City. Pockets empty, pockets full—it didn’t matter. Say I was guided by a yogi’s parable: “Given a fine cashmere coat, I began to worry about losing it. When it was finally lost, I felt nothing but relief.”

My 1990 HIV diagnosis handed me a death sentence. But it also gave me a calling, a career: Recovering from bacterial pneumonia, I sat on the couch flipping TV channels and realized no one was talking about AIDS—at least, no one who looked like me (short, hairy, Lithuanian, Jewish). What did I have to lose? I began speaking about my HIV at drug rehabs, ASOs, colleges, community centers. Fees were immaterial. Lives were at stake; mine had meaning, and I wasn’t worrying about getting paid.

In 1994, an agent introduced me to the wonderful world of speaker’s fees. My spunky-chick-faces-AIDS rap began to ring the registers, and suddenly I was awash in cash. I suck as a musician, can’t act a lick, but I can stand up, shake my cellulite and laugh at myself. It seemed to work, making all of us feel less afraid in the dark nights of AIDS.

In those days I still counted my life span in one-day-at-a-time units. I swam against the cash flow, gave a lot of it away and never thought about saving—until I met my current honey in 2000. He dreamed of owning a home. What the hell, I said, and on a whim we bought a fixer-upper on five acres in The Middle of Nowhere, Pennsylvania.

I walked into that house as if putting on the yogi’s cashmere coat. I found myself plunged into the details of mortgage payments and other bills—garbage collection, water, taxes, propane. At the same time, college budgets and speaker’s fees began receding, and one morning I woke up in a cold sweat, realizing poverty was no longer the adventure it had been in those Mexican cafes. “Lose the coat,” I thought, “sell the house.”

But it had finally dawned on me that I might actually survive HIV. My last near-death experience had been two years ago, my viral loads were holding steady, and a weekly IV kept my bone-marrow disease in check. After 12 years of rush-to-the-hospital, get-my-affairs-in-order moments, the thought of planning a future instead of a funeral shook me up. What would I do when I was 50, 60, 70? I knew one thing: I wanted to be living in that sweet house with that sweet honey.

So I hit the phones, calling everyone I knew, trying to get my bank account off its starvation diet, trying to sell myself. I felt like Willy Loman. People didn’t call back. The fridge went bare; we couldn’t buy furniture for our fixed-up fixer-upper. I paced the empty rooms, making call after call.

I didn’t like myself this way. How had my genetic indifference to money mutated into cold-cash dependence? Surprise conclusion: My terror wasn’t really about (as therapists say) money. The fear of loss, which I thought I’d escaped when I was first learning to be so brave and funny about HIV, had finally caught up with me. Now that I was no longer actively dying, I’d become desperate to hang onto life. That fear, not the house, was my cashmere coat.

I had to get back to the place that had once brought me peace. I started talking about living, disease and death again—forget the fee. I went to places where people loved me but hadn’t been able to afford my high-end prices. I spoke in prisons, halfway houses and rehabs, faced my terrors and talked my heart out.

Once I let go of chasing the buck, money started to trickle in from the most unlikely sources. It was like adopting a baby one day and finding out you’re pregnant the next. The house is still a bit bare, but I sleep better. My flimsy funding reminds me that clutching at dear life is not the same thing as embracing it.