Letting go of money (and an old friend) in Italy.

I’ve honed cheap-skatery to a fine edge. I re-use foil and Ziploc bags, self-administer haircuts, pedicures and even Brazilians – attaining a Jedi-level of self-grooming. Heck, I’d even drill my own teeth if I could, and have occasionally been known to file my own choppers when rough.

It pains me to spend money, so a month-long trip to Italy with my husband Dave to celebrate his retirement promised to be a little excruciating. Not that we’d be living like senators, mind you; we got a cheap flight and Dave had chosen reasonable Airbnb rooms with kitchens so I could cook some of our meals. Also, we’d be taking public transport whenever we could.

No, it was all the unanticipated extras that made me wince: cab fares, toilet fares, and paying for water (water!) in restaurants. It was also the sad realization that even though the Euro was down, it was still worth more than a dollar, so a €30 dinner was actually $33.73.

When we arrived in Florence, known for its well-crafted and inexpensive leather goods, I’d reached a Scrooge McDuck level of frugality – at least in my head. A well-deserved leather jacket and briefcase for Dave and beautiful saddlebag purse for me brought no joy, only Eyeore-like thoughts. “We can’t afford this.” “We’re pillaging our emergency fund.” “We’ll bounce our checking account.”

I put a good face on it and tried to enjoy the rich chaos of Rome, lushness of Florence and quirkiness of Venice, but by the time I got to the gritty city of Naples, I knew my attitude stunk and could use a change of clothes. It took the death of a friend to shame me out of my pinch-faced parsimony.

Andy Jones was a new acquaintance. A jazz-loving, energetic man who had just celebrated his 88th birthday, he sparkled with vitality and optimism. He still worked as a greeting card salesman and began every day with 1,000 sit-ups (you read that right) and a seven-mile walk. He gave away his old suits, not to divest himself of possessions, but so he could buy new ones in hopes of impressing the ladies.

We thought Andy would live forever. There is a Japanese word that describes him exactly –  “genki.” Roughly translated, it means enthusiastic, energetic, lively – game, ready to go. That was Andy Jones.

He found our group of friends through a shared love of music, and we spent many Friday nights circled around the piano, singing songs from the Great American Songbook – Andy’s favorite genre. He went from being shy and requesting songs, to singing them with gusto.

We loved getting to know Andy and looked forward to many more gatherings. When Dave learned on Facebook he had passed away of a heart attack, we were both stunned. And here we were in Italy, unable to attend the funeral and filled with sadness.

An inescapable truth of Rome is how impermanent we all are. The ruins of Italy have far outlasted the life spans of their creators by thousands of years. The many statues and monuments are for people long-gone and mostly forgotten. The cosmic clock stops for no one – not the citizens of ancient Rome, not Andy, certainly not for me.

Andy Jones wrung every drop of juice out of his 88 years, why wouldn’t I do the same? Here I am in Italy with the man I love. We’re both in good health, and have an emergency fund to plunder. How about I buy some expensive gifts and that sexy dress from Florence? Or, fully enjoy the vertiginous views from The Path of the Gods over the Amalfi Coast; bask in romantic, peach-colored sunsets over the Ponte Vecchio in Florence, and ogle over Michelangelo’s David? Must I be the Grinch Who Stole Our Italian Vacation? I couldn’t think of a single reason why I should and, I’ll bet, Andy couldn’t have either.

The heavy chains of miserliness fell from my shoulders. I didn’t look at the bills anymore or question Dave’s purchases and decisions to use a cab instead of walking. Best of all, I could finally drink in the richness of Italy with abandon – mind you, with €5 bottles of wine.

The night Captain Fantastic gave me a voice.

The Chrysler station wagon smelled of cigarettes, beer and spoiled milk. It always did on hot humid nights. My older brother Greg was driving, and he and his friends were playing that stupid game of repeating exactly what each other said a split second after saying it. It was like being in an echo chamber full of morons and it was irritating.

That summer of 1975 was big for Elton John. He had released Captain Fantastic and the Brown Dirt Cowboy, and the breakout single Someone Saved My Life Tonight was playing on the radio. A miserable and lonely 14 year-old, I identified with the world-weary, but hope-filled lyrics and passionately sang along, oblivious to the snickers around me:

I never realized the passing hours
Of evening showers
A slip noose hanging, in my darkest dreams
I'm strangled by your haunted social scene
Just a pawn out-played by a dominating queen
It's four o'clock in the morning
Damn it! Listen to me good
I'm sleeping with myself tonight
Saved in time, thank god my music's still alive

As he’d done so many times before, my brother snapped the volume off, leaving my voice exposed in the now-quiet car. In the past, I’d sheepishly clam up, unconfident in my own voice. Not this time. Those stirring lyrics – hearing my own voice above the mocking – gave me courage to sing with unexpected strength:

Someone saved my life tonight sugar bear
You almost had your hooks in me, didn't you dear
You nearly had me roped and tied
Altar-bound, hypnotized
Sweet freedom whispered in my ear
You're a butterfly
And butterflies are free to fly
Fly away, high away, bye bye

The laughter had stopped, and Greg turned the radio back on.

That night was the beginning of finding my voice – a process that still continues. Sometimes that voice is quieted by soul-crushing failure, a negative review or disapproval from others. But magically, the mere act of speaking out – singing, saying or writing what seems true – blasts open the timid doors of my heart and I’m free to fly.

Someone saved my life that night. Turns out, it was me.

Money-smart, marriage-smart.

My husband and I left the room after two hours, spent, hungry and light-headed. Had we been arguing, engaging in “afternoon delight,” or working out? Nope. Just talking about money. We joked that we were “divorce-proofing” our marriage.

I wasn’t always money-smart. My family didn’t buy lottery tickets, but we somehow believed money would magically appear. Budgeting was for the bourgeoisie. My father spent as he wished, while my mother fretted, saved and arranged deck chairs as their ship slowly sank. Though they recovered financially, I was imprinted by their mixed messages.

I was a math-phobic child. Multiplication tables caused me to blank out with fear. I failed math every year of high school, then barely passed it in the summer make-up. My math illiteracy led to an avoidance of anything financial.

In my first marriage I was frugal, but like my parents, mostly ignorant about the state of our finances. My then-husband would tell me cash was low and not to spend until a check cleared. Instead, I would hear “The apocalypse is coming. Buy cereal, toiletries and paper towels,” and overdraw our account.

I regularly engaged in financial infidelity – hiding purchases and misrepresenting my income. Yet, we rarely argued. Discussions about money were off-limits. Clearly, I had baggage I wasn’t ready to unpack.

Money avoidance was only one of our issues, but a clear metaphor for lack of intimacy and transparency in other areas. For 25 years we arranged deck chairs on our own sinking barge. In 2006, I jumped ship to a new life.

My first act of financial transformation was preparing a budget for the divorce lawyers. I was terrified to find out my true fiscal state, and wrangled a girlfriend to walk me through this basic skill. Money-wise, I felt like that kid who kept failing math.

As the numbers tallied up, I was stunned to find that a modest apartment, saving for both retirement and a down payment for a house were actually affordable. Expenses that didn’t matter anymore were gleefully slashed, like cable TV or a new car – making room for such luxuries as hair foiling, eating out and vacations. This math was fun!

After the divorce I started dating and developed a checklist of desired attributes. He didn’t need to be rich, but his finances couldn’t be a hot mess – that was my old life.

My new boyfriend Dave and I had many wonderful things in common, but some not so lovely. We shared a fear of money and a checkered financial history. Aside from a small car loan, I had wrangled the debt goose, but Dave still had money troubles  – a good deal of debt and an upside-down mortgage. Though most of the debt was due to his late wife’s illness, his balance sheet was a yellow flag to me.

It wasn’t romantic, but some of our early discussions were about finances. Turns out, my new love was naturally frugal, but didn’t like to say no to his significant other – a recipe for money problems. I was a spender, and splurged when fearing scarcity – often on useless items or impulse buys.

Instead of pre-marital counseling, we took a budgeting class together. We unearthed our inner money nerds and worked on changing bad habits – excruciating at first. The angriest we ever got with each other was in structuring our debt repayment. Outmatched, we hired a financial coach with Solomon-like wisdom to referee. Secure we were on the same page financially, we became one in the eyes of God, the law, and our bank account.

By tightening our belts, living in a cheap apartment and driving beater cars, we were debt-free in three years. Five years later, we are now on our way to paying off our simple home and securing a bright financial future. We still make mistakes, “forget” to mention purchases and impulse-buy on occasion, but quickly right the vessel.

Dave and I trust each other and don’t have secrets; it’s the basis of intimacy. Full-disclosure financially has also required us both to put our oars in the water and pull in the same direction – good for any couple. And that’s a ship neither of us are likely to jump.