08/11/2026
New Series Alert: SIDEBAR
Little context before we get into it. I’m a lawyer, which means most of what I post is supposed to sound polished, certain, buttoned up. This isn’t that.
Sidebar is where I say the things I’d normally only say to another founder over coffee. The stuff I’m still figuring out in real time, not the stuff I’ve already got a clean answer for. No polish, no tidy takeaway at the end. Just the actual thoughts.
New entries, whenever I’ve got one worth sharing.
Sidebar Vol. 01 -
Something I’m actually sitting with right now: where’s the line between being generous with what I know and just giving away the thing people should be paying for.
I built my whole content strategy around sharing how I actually think, not just information you could Google. Which means people now DM me real questions. Detailed ones.
“Quick question” that’s actually a 20 minute legal analysis.
And here’s my problem. I want to be the lawyer who’s actually helpful online, not the one who gatekeeps everything behind a consult fee.
But there’s a version of “helpful” that quietly turns into free legal work and I haven’t fully figured out where that line is yet.
Too generous and people never actually hire me, they just collect my answers. Too guarded and I become exactly the kind of professional I said I didn’t want to be.
Still figuring this one out in real time. If you run a business where people pay for your judgment, I’m curious how you draw this line.
Where do you personally decide “this is a DM I can answer” vs. “this is a paid conversation”? 👀
