I had a pretty lively discussion with someone on the twitter this morning who had some strong opinions about how everyone should be self-employed and that we should quit relying on “The Man” for a job. I expressed some concern that before cheering them to jump off the ledge, we should perhaps maybe encourage people to first assess the risks, that they should jump with eyes wide open.

Twitter being what it is — by the end of the discussion — I was accused of scaring people, looking for more ways to fail than to succeed and killed fifty people on the highway with a load of wood. I may also have been called stupid, but I ignored that. The whole time I was chatting, I heard Rebecca Pryce’s voice in my head from the season finale episode of Mad Men:

“You had no right to fill a man like that with ambition.”

Before I offer an opinion, I’d like to share a story.

A few years ago, a neighbor down the street lost his job. He was fairly young, had an engineering degree and by all measures, was gainfully employable. Only the market was soft.

A few months into it without finding work, his wife left him and his son. Who wants to hitch their wagon to a loser? Not her.

To keep busy, he started repairing bikes for the neighborhood kids. As it turns out, he was pretty good at it. We would walk past his garage early in the morning and he would be out there almost every day. Week after week, his garage filled up with more and more bikes as his “business” started expanding. He would start his day earlier with each passing week and we got to talking. For a while, I assembled and repaired bikes in retail stores for Huffy and so I shared some tips and tool suggestions, which he gobbled up hungrily.

But I also worked in the corporate office and saw the “other side” of the assembly and repair business; the ugly side of product liability. I saw — and testified at — liability hearings where we were accused of all sorts of negligence. We lost some; we won a few but mostly, the insurance finally settled before trial. There was almost always a settlement.

“Do you have liability insurance?” I would ask him from time to time.

“I’m not big enough to sue,” he’d say. “Beside, insurance is expensive.”

Until some kid got hurt on a bike he repaired.

Overnight, he turned from a neighbor saving a mom from the expensive bike shop to a predatory monster, out only for profit. At the end of the ordeal, he lost a $130,000 judgement, was fined by the city for running a business without a license in a residential area, sued and fined by the State of Ohio for uncollected sales tax and was slapped with other various tax avoidance annoyances. At some point during this ordeal, he was able to find a job and is still paying off the judgement and fines.

Even though all his revenue and more was swept away in one fell swoop, he was able to feed his kid and keep his house with what he charged for the repairs. That was something, but while he could afford the meal. he could not afford the tip. There was not enough profit in his “business” to be able to afford to protect himself. In short, he really wasn’t in business; just scraping by on the dollars of customers too cheap to pay professional bike shop rates. Without the luck of finding a full time job when he did, he would have been destroyed.

Sometimes we pass by his house on the morning walk as he is pulling out of the garage on his way to work. We stop and let him go by, wave and glance briefly into the garage. It is as clean as a whistle, all the bikes and tools long ago having been cleaned out. I doubt very much that he will ever go into business for himself again. And that is probably ok.

In social media, we live in a rarefied world where twitter and blogs attract those most likely to have a penchant for self-employment or entrepreneurship. As we discuss the state of work in this economy, we sometimes forget that most people are not cut out for the rough and tumble world of going it alone. Even among those who are built for it, there are a large percentage of us who will fall by the wayside in failure. That is not fear-mongering or being negative; that is being pragmatic.

During the “good times,” my neighbor was all about being self-employed. He almost quit looking for work and talked excitedly about expanding this repair business. I nodded a lot, hoping he would beat the odds. He didn’t.

It is easy for this new group of self-employed to talk about the new normal being self-employment and entrepreneurship. It is this reality that many are being pushed into and many are embracing in the absence of any other model presenting itself in the near future. Folks like Seth Godin and Daniel Pink are declaring self-reliance as the new state of “employment.” When these gurus romantically wax nostalgia of the good ol’ days when we were all craftsmen, the allure is intoxicating. But the reality is that most of the population was always employed by a small subset of businessmen. History always gets written by the winners. Except here.

History also show us that the breakdown of a social order is almost always preceded by what looks like a bright future of independent work. In reality, it is the frantic, desperate attempts of individuals competing against each other for survival.

If I have learned anything on the road to geezer-ville, it is to tread lightly when dispensing advice. Who are we to claim the right to fill people with ambition?

If you can’t talk frankly about risk, you probably shouldn’t be taking it. If you aren’t willing to share in someone else’s failure, you should perhaps not be dispensing advice to them.