Reflections on Freedom: A Six-Year Journey

a raw stream of consciousness. 4th of July – six years later. Chicago, IL.

Six years ago, I pondered the summer ahead on a balcony in Bra, Italy in this blog. I reminisced on the 4th of July of years past, and the 4th of July of years ahead. I envisioned a summer, and a life, led by unabashed and reckless abandon. Intuitive guidance would lead the endeavors, dreams, and ensuing action toward a life of beauty and adventure. 21-year-old me was a dreamer, bright-eyed and longing for adventure.

This life of beauty and adventure I sought was to begin with research at a University in Italy, thanks to a Northwestern research grant, and potentially a master’s degree upon graduation thanks to a Fulbright. A master’s degree focused on sustainable food systems and the philosophy of life through food; that food should be “buono, pulito e giusto”- good, clean, and fair- for all. Through food, a value system reimagined through a return to the slow life; the meditative approach towards food in the micro could somehow expanded to the macro through my research.

Life somehow got in the way of my pursuit. The global, and personal, catastrophe that was COVID led to the death of an identity and persona within me. Meanwhile, the University lived on in my conscious and unconscious for the next six years, as I reemerged from COVID a changed person, following me on commutes to work, in high-stakes meetings with high-end clients from around the world, and throughout my free time. Almost an obsession, the idea of changing course was stuffed down internally by the idea of the “sensible” path forward.

Over time, I tried to reimagine the “sensible” path. To stack more cash in the bank for a false sense of security while your intuition and well-being suffer in the pursuit of stability, safety, and comfort? Life evolved to become a test of this idea.

Over the years, I devoured hours of self-help and personal finance blogs, books, and podcasts. Reddit’s r/FIRE community. Ferris’s 4-Hour Workweek. Yang’s Smart People Should Build Things. Sandberg’s Lean In. Hormozi’s endless mind-numbing path to millions and millions. Every philosophy sat within me.

Other areas I left unexplored until recently. What about Valva’s The Taste of Art, or Waters’s We Are What We Eat, and Petrini’s Manifesto? Interdisciplinary learnings from E.F. Schumacher’s Small is Beautiful, or the literary genius of Pessoa’s Book of Disquiet? What else can one learn from Euclidian geometry or Marxist philosophy, astrophysics or Jungian psychology? Above all, what can I grasp from re-engaging with the most reflective of the human spirit’s essence via music?

A tug of war between the sensible and the dream world played out within me day in and day out. I was seeped in a world of high finance, an aperture within me forced to be set to “return on investment”, “total value / paid in”? I started to ponder, is life to be measured by Total Value to Paid In capital? What about the productivity of the Spirit? What’s the economic value of that?

I had a decision to make at the beginning of this year: to give in to the curse of the Golden Handcuffs and wait out the year for another promotion, another bonus, an offer of equity, and a healthy profit-sharing match. A road diverging between the velvet coffin in which my spirit was laid to rest, or to say NO and venture off on a path to follow my dreams, stumble along the way, make a fool out of myself in some cases, and simultaneously impress on those around me the beauty of listening to intuition and of following through with a difficult path despite the discomfort.

My values have started to emerge slowly over time.

How many of us consciously live our lives? Do we ever slow down, even stop, to examine why we want the things we do? Why spend $100k on a wedding when that could potentially provide a foundation to live the life one WANTS to live outside of golden handcuffs, another iPhone, a more exotic 1-week vacation twice a year, meanwhile hating the drag of the days and disappointment at the notion of spending another 30 years in the same cycle of acquisition and depression?

How many of our material items own us, while our unconscious minds scream in our daydreams and nightmares?

Why do we ingest poison regularly, alcohol dulling our senses, decision-making abilities, and self-control? Spending hard-earned cash on a substance we unconsciously ingest simply because of societal pressure.

Why do we self-impose so much harm?

This 4th of July is a return to myself, and the start of the next 6 years. Where will this chapter take me?

Stay tuned into Il Caffe to find out.

Tabula Rasa

Blank slate – what will come of this next step?

Five years later, many hours of contemplative walks, discussions with friends, family and therapists.

One application later. One acceptance later.

Il Caffe is to be born again – an expansive opportunity to jot down any and all ponderings.

My advanced apologies for the mess that will be my getting in “writing-shape” again.

Yet, there is something beautiful in infancy; naiveté, inhibition, pure optimism.

Follow Il Caffe Americano as she journeys through…. Università degli Studi di Scienze Gastronomiche a Pollenzo.

Five years – never too soon, never too late.

Ci Vediamo.

What’s Money Got to Do With It?

Everything, apparently (according to my father.)

Once again I find myself wading out into the murky waters of the unknown; to go to Italy for a master degree, or to not?

The application, completed. The transcripts, secured.

My bank account, and overall financial future, not so much.

I got engaged two weeks ago, and have enjoyed celebratory drinks and meals, but looming is the uncertainty about our next chapter together. Will I continue a life strapped into a career that doesn’t inspire me but provides the comfort and stability of a warm home and lifestyle creep?

Since the age of 15, I’ve never not had a job. I waited tables throughout high school, college (even paid my way through senior year on a server salary), and beyond. Since Covid, I’ve enjoyed the perks of the 9-5 office job; fantastic health insurance and a steady drip of income every few weeks.

My partner, though, has taken the less-trodden path. Trudging upwards at a startup has not been without it’s pitfalls as the flexibility and upside potential is not without cost.

Which brings me to today – another year has gone by and another application tab is still open on my desktop, along with Fidelity, Vanguard, Chase, Bank of America and American Express. How many Reddit articles can I write, anonymously asking strangers advice about what they would do in our “net worth and cash flow profile” situation. Is the financial risk of a life of beauty, adventure, and unknown worth the plunge? Will my values hold up when our bank accounts start to retreat?

Only time will tell..

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