Nye's Digital Lab is a weekly scribble on creativity in an age of rapid change.
I'm starting from Zero... again.
Essay #89
I was bad at sales for most of my life.
Not shy-bad. I think I can talk to anyone. Competent-bad. The kind where you know the work is good and the pitch is true and the client needs exactly what you make, and still you can't get your mouth to do the part where you ask a stranger for money. I'd walk to the edge of the ask and hear myself say "anyway, let me know if you ever need anything." That's not a close. No wonder they never called.
It took me years to see what I was doing. I was protecting myself. If I never asked, nobody could say no, and the good opinion I had of my own work could stay sealed in its case. Nice and safe.
This went on until it caught up with me. I hit a bad stretch (the specifics don't matter, everybody gets one) and my friend Gavin sat me down. Gavin is a salesman,
Ask them for coffee. Say this is what I do... is there anyone I should talk to?
Write down whatever they say. Go down the list.
No funnel, no deck, no pipeline. A legal pad and two sentences.
I did all fifty and it took months. Most were nothing. Some were humbling; one guy checked his phone the entire time, said "cool, cool, cool," and left, and I sat there afterward conducting a full inventory of my life choices. But some gave me a name, and the names gave me names, and by the end of my run in LA I was running a small shop and landing deals. That's a sentence that would have made me laugh out loud in 2003.
The fifty cups of coffee are not a sales technique. They're a machine for turning humiliation into arithmetic.
Every ask felt like a referendum on my worth as a person, which is a lot of weight to hang on a flat white in a Santa Monica coffee shop. The list dissolves that. Once fifty names exist on paper, a bad coffee isn't a verdict, it's just name "seventeen." The failure rate is pre-approved. You can't be destroyed by an outcome you already wrote into the plan.
For a long time I was in my head, and I filed my 50 cups of coffee under "amateur."
Real salespeople had training and language and systems that came from somewhere. I had a legal pad from Gavin. But it's the same with everything else I ever built because nobody would tell me the process. None of it came from a book. All of it got invented at the moment of need by a guy who didn't know what he was doing and couldn't afford to say so. I thought that was the shameful part.
Ha. Look at that. It was the job.
I look back at my history and see real work. Projects, relationships, growth. They're what got left behind. The actual career. The only thing that traveled with me from one collapsing industry to the next is a stack of improvised systems I built while standing in rooms where I didn't belong yet.
I'm not a portfolio. I'm fifty cups of coffee and a collection of forty other short hand frameworks I made up under duress. Because that's what it is.
I'm starting a new chapter now, pointed at robotics and AI, and I know exactly what this is.
I guess it's the difference between fifty and thirty. The feeling hasn't changed:
the papers where I follow the abstract, lose the plot around page three, and reach the conclusion with the facial expression of a dog watching a card trick;
the nineteen-year-olds who've been building with these tools since they were sixteen;
the terms I look up, and then look up the words inside the definition.
Twenty-five years in, and I'm functionally a beginner. At thirty that meant you're about to be found out. Now I recognize it on sight. It's not a warning. It's the feeling of the first week. I've had this exact week forty times, and every time it was followed by a second week.
It's confidence about the interval between not knowing and knowing, the only part of my career that ever repeated. I'm good in that gap (I guess?). I've spent my whole life there. Improvisation isn't what you fall back on when the plan fails. It's what works when there's no plan yet, which is most of the time.
Which is convenient, because everyone is standing at zero. This is fact.
The tools that matter didn't exist when the current experts were forming their expertise. The gap between me and the person who intimidates me isn't thirty years of wisdom, it's eighteen months of reading and considerably more nerve. Nobody has a deep bench; there hasn't been time to build one. Everybody's improvising.
So I'm doing it again. Fifty names on a friggin' legal pad. (Thanks Gavin) I'm going after researchers, founders, weirdos with good github repos, a few who'll never write back. Same two sentences. Write down the answer. Go down the list. It felt amateur at thirty. It doesn't now, because waiting until you're qualified is a slower way of never starting, and the qualification was always the same thing:
willingness to be at it, in public, for a while.
Zero isn't a hole you climb out of. It's where everyone is standing right now, mostly pretending otherwise.
Bring a pad. And... Make it Happen.
Nye Warburton is an educator and adventurer from Savannah, Georgia. These essays begin as improvisational sessions with Otter, are ingested and revised in Obsidian, and then sweetened with Claude's fancy suite of agentic tools.
A collection of last year's essays are in a printed edition are available to purchase at https://nyewarburton.com/book/
The Two Currencies of Creativity - On knowing your worth and when
Own your Work - On understanding IP for artists
It's All in the Collection - On holding your work locally and in context
Nye
Comments