Plot Twists: An Old Lawyer's Journey Through Code, Law, and Second City
Sixty Years of Life, Law, and the Occasional Existential Crisis
Let me set the stage: After six decades of living, raising kids, and practicing law, I shook things up by moving to Chicago, starting a software company, and taking up script writing and acting at Second City and Acting Studio (for the serious stuff). As it turns out, good lawyers are great actors and I am a very good lawyer. As I get ready to launch my technology to the world and stage my first three act play, I was not busy enough and, thus, decided to start a substack to tell you all about it.
I know what you’re thinking. “It’s a blog about an old lawyer who codes for work during the day and writes in iambic pentameter at night?” Bingo! That’s it exactly. Here’s why - I’m not twelve! When you have lived as long as I have as I have, you see that your three big passions are linked: legal reasoning, coding, and theatre. All three come down to the one thing – telling stories that matter.
The Plot Thickens: Medicaid, Microservices, and Method Acting
I'm an elder law attorney (yes, that's a thing; no, it doesn't involve séances or debugging legacy code from the 1980s). I help people who didn't plan ahead and now face bankrupting care costs. What is my law firm's record for the most a family had to pay for long term care? $30,000. Per month. That's enough to make you want to pivot to a subscription-based model, isn't it?
But here's where my worlds collide in fascinating ways. While building software solutions to streamline estate planning (because apparently, I enjoy challenging myself), I've discovered that the principles of good coding – modularity, scalability, error handling – mirror the strategies of solid estate planning. And both require the kind of improvisational thinking I'm learning at Second City.
The Rub (Now with Extra Bytes)
As Hamlet said, "Aye, there's the rub" – though if he were a modern tech entrepreneur, he might have called it a "critical system failure." The fact is, 70% of Americans don't have even a basic will, let alone an asset protection trust or a GitHub repository of their digital assets. We're terrible at facing our own mortality, preferring to binge-watch The Bachelor rather than tackle those existential questions like, "Who gets my Bitcoin if I'm in a coma?"
Building a New Kind of Community
What am I building here? Think of it as a distributed system of Family Leaders (yes, capitalized, because it's that important). These are the folks who understand that thriving in today's world requires more than just a retirement plan – it needs a full-stack approach to legacy building. We're talking about wealth in all its forms: financial assets, intellectual property, digital footprints, and those priceless family stories that deserve better documentation than a shoebox of photos in the garage.
Your Subscription Benefits
Weekly posts will blend legal insights, tech perspectives, and theatrical observations. Free subscribers get the pilot episode: practical tips, candid observations, and my ongoing commentary about why society hasn't created an API for long-term care planning. Paid subscribers? You'll get the director's cut – deep dives into topics like "How to Survive a Medicaid Spend-Down While Building Your MVP" and "What Improv Comedy Taught Me About Estate Planning."
Consider this newsletter your backstage pass to a show where law meets tech meets theater. Together, we'll explore the intersections of these worlds, finding humor in the complexity and wisdom in the chaos. Think of it as a TED talk meets standup comedy meets legal seminar – with maybe a few lines of code thrown in for good measure.
So, there it is. My grand opening night on Substack. If you stick around, I promise it'll be more engaging than watching paint dry on your continuous integration pipeline. And if not, well, there's always debug mode.