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Rob Drilea

Rob Drilea

On creativity & work

Compouding loopholes

ProPublica published this morning a damning report on how the wealthy avoid income tax, revealing new data from a trove of "never-before-seen records." All to resounding silence. We know. We don't give a damn. Taken together, it demolishes the cornerstone myth of the American tax system: that everyone pays their

Compouding loopholes

On technology and magic

This is me, reading the first lines of a touching poem I just discovered yesterday by Lawrence Ferlinghetti, who passed earlier this year. But this is also not me. It is my voice, with my accent, with my intonation. My breath is in it. And yet, I've never said those

On technology and magic

Fiction and my search for meaning

Three things happened when I was seven years old that would come to have a profound impact on how I came to understand the world. First, I started taking "computer classes." This was the late 1990s in Romania - computers were still the future. Thinking back, I now realize what

Fiction and my search for meaning

Always take the stairs

Until I was 16, I lived on the sixth floor of a standard communist bloc of flats in a standard neighborhood of Bucharest. The elevator wasn't working half the time, and the other half it was busy. So I mostly took the stairs. I recently realized that since I moved

Always take the stairs

Where are you from?

The first time I was asked "where are you from" was shortly after I turned 17. I was born and raised in Romania, of Romanian parents, of Romanian grandparents, and roots as static as I could trace, as far back as I could go. I grew up sheltered, in a

Where are you from?

Build a creative discipline

"Most postponements are excuses for a lack of creative discipline." - David DeidaThere is no excuse for me to not write an hour everyday. I've made excuses for years now. I didn't use to. In my early teens, I would spend hours and hours writing every day. Mostly junk, sure,

Build a creative discipline

Twelve problems

This week I joined the latest cohort of David Perell's Write of Passage course, and one kickoff assignment is to think through 12 of our favorite problems. I love living with the questions. I think the practice of asking big questions that aren't necessarily actionable is essential to a fulfilling

Twelve problems

Beyond to-do lists

My track record of productivity for most days I work for myself is pretty shameful. I've worked as a freelancer most of my career. For a period, I was a permalancer, or a full-time freelancer - that increasingly common creature of our shifting labor markets who is committed to an

Beyond to-do lists

WELP: Framing purposeful work

I graduated a top ten college in a good job market, with actionable skills and a decent portfolio of work - and yet, out of 300 jobs and internships I applied to, I only landed one. It all worked out well enough. That first internship, with a small production company

WELP: Framing purposeful work

Walk & talk

A couple of weeks ago, a family friend of mine reached out inviting me to walk together and catch up. This is a really important person for me who I usually get to see once or twice a year, but has become a role model and mentor from afar -

Walk & talk