I Wouldn't Have Even Tried

My friend Anirudh is a senior PM at PayPal. Last week he walked into a leadership meeting and demoed an interactive dashboard he'd built — navigation, drill-downs, the whole thing — pulled from a 100+ MB file of raw customer feedback. The insights are going to shape real revenue decisions.

Afterward, I asked him: "How would you have done this a year ago?"

He didn't hesitate. "Honestly? I wouldn't have even tried."

That answer has been bouncing around my head for a week, and I want to share why.

The ceiling, not the clock

Most AI stories are about speed. Write the email faster. Summarize the doc faster. Clear the inbox faster. Those wins are real — I talk about them here all the time, and they count.

But there's a second gear, and that's what Anirudh found.

He's not a developer. Building an interactive dashboard the old way would've meant learning enough web development to pull it off — two, maybe three months minimum — and probably handing it to a dev team anyway. So he wouldn't have done it. He would've loaded the feedback file into a spreadsheet, skimmed a few rows, pulled a handful of quotes, called it a day.

What AI changed wasn't his clock. It raised his ceiling.

Both gears matter. Speed makes the things you already do well feel lighter. Ceiling lets you reach into work you'd written off as "not my skillset" or "too much work." The first is obvious once you've tried it a few times. The second is where the real leverage quietly lives — and it's the one nobody talks about enough.

But you need a North Star

Here's the part that matters, though — Anirudh didn't stumble into a dashboard. He had a question he genuinely cared about: what are our customers actually telling us, underneath all this noise?

That question was the anchor. Without it, AI becomes a shiny toy — you poke at it, it spits out impressive things, you close the tab, nothing changes in your week.

You don't need a grand plan. You don't need to know which "AI workflows" you want to master. What you need is closer to this: if I had a patient, capable intern sitting next to me for a week, what would I love to finally pull off that I've been shelving?

Your starting point isn't a tool. It's the thing you've been writing off.

The unglamorous middle

I want to be honest about something else. Anirudh didn't nail that dashboard on his first try. His early outputs were messy. The analysis had gaps. Things were formatted oddly. He kept going back — refining, asking better questions, redirecting.

This isn't grind culture. I'm not asking you to hustle. The opposite — I'm asking you to be patient with a clumsy intern.

That's the analogy I keep coming back to. AI is fast, eager, and occasionally hands you something that's just plain wrong in a confident tone. Your job isn't to accept the first draft. Your job is to be the boss — look at what it produced, tell it what's off, ask for another pass. The first try is never the finished thing. Nobody's is.

Anirudh's 14 hours weren't 14 hours of smooth progress. They were 14 hours of "okay, try that again."

It's a skill, not a trick

One more thing: like any skill, you get better at this with use.

Your first session with AI will feel awkward. Your tenth will feel natural. Somewhere around your fiftieth, you'll start noticing things to try that wouldn't have occurred to you earlier — "oh, I could use this for X too." That's not you becoming a power user. That's just you, plus a tool, over time.

If your employer is paying you to figure this out — giving you tools, time, and real work to practice on — that's a privileged spot. Use it. The compound effect of practicing on work you actually care about is bigger than any tutorial.

If that's not your situation, don't let that stop you. The free tiers of the major tools will carry you through months of real experimenting before you'd hit a wall. And if you find yourself leaning on one daily, paid tiers are there for when you're serious enough that they pay for themselves in saved time.

Either path works. What doesn't work is waiting until you have "the right setup" to begin.

What I'd actually like you to try this week

I don't want you closing this thinking you need to go build a dashboard next week. You don't. You shouldn't.

What I do want you to try is this: make your gap list.

Write down one or two things you've quietly shelved because they weren't your skillset, or they seemed like too much work. A few I hear often:

• "I should clean up this messy spreadsheet, but I don't really know Excel."

• "I'd love a simple one-pager explaining our team's process, but I'm not a designer."

• "I've got 20 documents I need to pull themes from, and I just don't have the time."

Pick one. Just one. Open a free tool — Claude.ai or ChatGPT's free tier works fine — and start with something like this:

I'd like help with [the task]. I'm not a [designer / analyst / whatever], so please walk me through it. Before you suggest anything, ask me 3 to 5 clarifying questions about what I'm trying to achieve and who it's for. Then give me a rough first draft I can react to.

The "ask me questions first" bit is the quiet magic. It stops the intern from sprinting off with half the story.

A few honest caveats, because I promised I'd always give you these:

• The first draft will be rough. That's the job, not a failure.

• Fact-check anything it asserts. AI states wrong things confidently all the time.

• Don't paste anything confidential — client data, sensitive internal docs — into free tools. Your employer probably has rules about this. Check first.

Where this is going

Anirudh said something to me recently that's stuck with me: "In a few years, developers will do PM work alongside their coding, and PMs will code alongside their PM work."

The walls between specializations are getting thinner.

That might sound threatening — like everyone's suddenly expected to be a jack-of-all-trades overnight. It isn't. Your depth, the thing you're actually good at, is still the thing. What AI adds is breadth. A little reach into the territory you used to leave to someone else.

You're not going to become a developer next week. Anirudh didn't either. He just reached into dev-adjacent work when the problem called for it, and came back to his actual job with something he couldn't have built on his own.

That's the direction. A year from now, I'd love for you to have your own version of Anirudh's line: I wouldn't have even tried that before.

Pull up a chair. Pick one thing off your gap list this week. That's the whole thing.