Bobadilla v. The Rip Tide
On algorithm-fed advice, the questions nobody gets to ask, and what a room full of real people taught me about the difference.
A prospective client came in a while back with a very clear-ish business plan.
I asked what he wanted to do. He told me the business type he was interested in. I asked what that meant in practice, what he was selling, to whom, solving what problem. He told me again – the same business structure type. Same answer, different inflection, a little more impatience. We went a few more rounds before it became clear that what he had wasn't a business. It was a the shell of business model someone had sold him. A category, packaged as a plan, delivered with enough confidence and enough video content that the gap between the two had never surfaced.
He'd done the work, or at least the stuff that riding the current of various social algorithms had told him the work looked like.
He left unhappy. I understood it then and still do now.
Floating the Algorithmic River
The algorithm is a current, not a compass. It shows you more of what you already believe, more of what you've already watched, more of the voices already agreeing with each other, internet “Drs.” who do technically possess doctorate degrees. Flowing with that current is designed to be a comfortable ride. It doesn't typically challenge your understanding or surface the question that pokes a hole in its own framework. It doesn't know what you don't know. It knows what you've watched, liked, shared, clicked on, and it finds more of that.
Content that performs best on any given platform is the content that confirms what the audience already suspects, wrapped in confidence, delivered at volume, with a subtle close of the sale somewhere near the end. The people who produce it aren't necessarily wrong about everything (or occasionally anything) they say.
They're thoughts, lessons, and opinions are optimized for a different outcome than the one you think you're getting. Engagement is the metric. Deepening or challenging your understanding is a byproduct, at best.
When I pulled up the LinkedIn profile of the person he'd invested hours and hours learning from, what we found there was enlightening. He recognized it immediately. That was a hard moment and I didn't enjoy being part of it.
The Room Designed for Learning
Around the same time, I presented a free commercial lease training for a group of local small business owners. These people who had also been doing their research. Reading the blogs, watching the videos, bookmarking the threads. By every measure of modern self-education, they were prepared.
And then the room opened into a casual conversation.
The questions that came out were the ones nobody had ever thought to ask, the answers being offered were things nobody had heard, or maybe fully understood before. Not because the people weren't diligent or smart. Because the algorithm had never pulled them into those questions. It had showed them answers to the questions they already had, the ones they knew to search for, the ones with good thumbnails.
What came out in that room were the questions that don't have cool answers, that made a single situation different and canned advice inapplicable. The ones that start with "wait, so does that really mean..." and end somewhere that restructures everything that came before it.
These are the kinds of questions you can only ask after someone explains something in plain language and stays in the room to hear what you still don't understand.
There are very few places where a business owner can sit down, raise their hand, and ask the question they didn't know was a question. The algorithm can't do that. A online course can't do that. A video with half a million views can't do that. A conversation can.
Questions as the Reality Test
There's a version of this you can address right now, without getting in a room and without booking anything.
Before you take advice from someone online, ask them a real question. Not a comment that says great content. An actual question that requires the person to know something specific, something that pushes past the framework they've already given you.
Do they reply? Is the reply substantive, or does it restate what they already said? Does it sound like the same tool that writes their newsletter? Does it end with a link to a page where they’re happy to take your money?
The quality of the answer tells you almost everything you need to know about who you're getting advice from. Someone who has done the thing responds differently than someone who has built a business around describing the thing online. That difference is usually visible pretty quickly.
The prospective client I mentioned had never found, or forced, the opportunity to ask a question. He'd been a consumer, not a participant. The platform rewarded consumption and gave him no signal that anything was missing until he was sitting across from someone whose job it was to ask the questions the content never had.
The Cost of Sitting in the Room
He paid nothing to watch the videos and found hope in a hard time. He came to a free sit down with a lawyer who blew it all up and left frustrated.
I understand why. The videos had cost him months of energy aimed at the wrong thing. The meeting cost him twenty uncomfortable minutes and gave him the one thing the algorithm couldn't: the question that needed to be answered before any of the other questions mattered. Without being able to answer that threshold question, everything else came apart and there was no work to be done.
The people in the lease training came in full of online knowledge and left with the questions they didn't know they had. Not because I told them things they couldn't have found elsewhere. Because being in a room with someone who knows the subject and can follow your specific confusion and help you find understanding is a different thing from watching someone explain a revenue category on a schedule that works for them.
The current moves fast and it genuinely feels like progress. Motion and progress look the same from the inside.
Asking questions, and finding someone to ask you questions, is how you tell the difference.
- m
