Author: rasheed.s.ahmadnc@gmail.com

  • Starting the Generalist Project: Six Months of Tactics, Debriefed

    Six months ago I made a deal with myself: stop planning, start shipping. Every week had a deliverable. Every deliverable had a deadline that mattered more than whether the work was right. It worked, in the narrow way that kind of work always works.

    I got faster. I got better at triage, at cutting scope, at shipping something rough on Tuesday instead of something polished on Friday. Those are real skills and I don’t regret building them.

    What I didn’t build was any sense of whether I was solving the right problem in the first place. Tactics answer how to do a thing well. They have nothing to say about whether the thing is worth doing. Six months in, I noticed I could no longer tell the difference between a good week and a wasted one, because I’d stopped asking the question that would tell me.

    So this is the debrief, and the pivot. The next six months are the Generalist Project: strategy first, on purpose, with a deliberate push into work outside my usual lane. I’m not abandoning the tactical muscle. I’m putting it in service of a question I skipped the first time around.

    New posts land here most weeks, along with the occasional video. If you want the rougher, less-edited version, it’s also going up on Substack.

  • The Six Months I Spent Winning the Wrong Game

    There’s a specific high that comes from shipping fast: the backlog gets shorter, the feedback loop gets tighter, and you start to feel like you’re good at your job in a way that’s easy to point to. I chased that high for six months.

    The problem is that a shorter backlog isn’t the same thing as a better one. I was optimizing execution on a list of priorities I’d stopped questioning. Every week I won the game in front of me without checking whether it was the game I actually wanted to be playing.

    The tell, in hindsight, was how rarely I zoomed out. Tactics reward speed, and speed punishes the pause it takes to ask a bigger question. So I stopped asking it, and got very good at answering the small ones instead.

    This series is the record of trying to fix that: fewer sprints, more standing back, and a real attempt to tell the difference between winning and winning the wrong game.

  • A Field Note on Reading Outside My Lane

    My reading list used to be a mirror. Every book was about the discipline I already worked in, written by people who already agreed with how I saw the problem. It felt like learning. Mostly it was confirmation.

    Part of this project is a deliberate rule: for every book that’s squarely in my lane, read one that has no obvious reason to be. Distribution logistics. Choir conducting. Whatever’s furthest from the desk I sit at.

    The payoff isn’t that these books hand me new tactics. It’s that they hand me new questions, framed by people who never learned to ask them the way my field does. That’s the actual shortage, and it doesn’t show up on a reading list of things I already agree with.

    Field notes like this one will keep tracking what’s actually working from that experiment, not just the shelf of good intentions.

  • Strategy Isn’t a Vibe, It’s a Constraint

    Ask most teams for their strategy and you’ll get a paragraph about ambition. Be bold. Move fast. Delight the customer. None of that is strategy. It’s tone, and tone doesn’t tell anyone what to say no to.

    The strategies that have actually held up under pressure, in my experience, are the boring ones: a specific customer we will not chase, a category of feature we will not build, a channel we will not touch even when it’s working for a competitor. Constraints, not ambitions.

    That’s the piece I skipped during the tactics-only stretch. I had plenty of ambition and no constraints, which meant every opportunity looked equally worth chasing. A strategy that can’t tell you what to refuse isn’t one.

    This is the first real attempt at writing one down, constraints first, ambition second.

  • Bookshelf Honk: What I’m Reading to Get Wider, Not Deeper

    A running list, updated as it changes, of what’s actually on the nightstand rather than what would look good on a shelf. The rule is range over relevance: nothing here was picked because it’s adjacent to work.

    Right now that means a history of the shipping container, a short book on how orchestras rehearse, and a field guide to urban foraging that a friend left behind on a visit. None of them will show up in a tactics post. That’s the point.

    I’ll keep adding to this one as the stack changes, and note which of these actually changed how I think about anything, versus which were just a pleasant couple of hours.

  • The Generalist’s Toolkit: Week One

    Week one wasn’t about finding a strategy. It was about building the small set of habits that make asking a strategic question possible at all, since six months of tactics had quietly worn most of them away.

    Three things made the cut so far: a standing hour, once a week, with no deliverable attached to it. A running list of questions I’m avoiding, reviewed instead of answered. And a rule that any plan has to name something it’s choosing not to do, or it doesn’t count as a plan yet.

    None of this is a system yet. It’s closer to physical therapy for a muscle that atrophied. More on what sticks, and what quietly gets dropped, as the weeks go on.