Working On vs Working In
Every morning I face the same small fight: do I write the code, or build the thing that means I don't have to? Close the deal, or build the system that closes deals? Working in the business is the actual work — shipping product, talking to customers. Working on it is the slower stuff — hiring, process, systems. Both are real work. Getting the mix wrong has killed more of the companies I've watched than any competitor did.
I default to working in it, and I think most founders who came up as builders do. It feels concrete. A feature ships, a customer's happy, a bug dies. Writing a hiring process gives you none of that. But there's a catch: a founder who only works in the business becomes the ceiling. The company can't grow past your personal capacity to do the work. You haven't built a company; you've built yourself a very demanding job.
When the weeds are the right place
Sometimes being in the weeds is exactly right. When quality slips, I want to see it myself. When a customer's unhappy, I want to hear it directly, not read the summary. Early on there's also just no one else — with a handful of people, the founder fills the gaps. The details teach you things the dashboard never will. The danger is getting addicted to being needed, until every decision routes through you and you've become the bottleneck you were trying to avoid.
A question that sorts it
When I'm not sure which kind of work something is, I ask: what happens if I don't do this? If the answer is "someone does it slightly worse," I hand it off. If it's "no one else can" or "the company breaks," I do it myself. Setting direction, defining how we work, the first real customer relationship — that's mine. Processing invoices, the fiftieth version of the same deal — that belongs to someone else.
The balance never holds still. A crisis pulls me into the code for a week; a hiring push turns into nothing but interviews. That's not failure, it's the job. The skill isn't finding a perfect split. It's noticing fast when I'm stuck on the wrong side of it.