Last week Chicago lost a great mayor as well as the most aggressive spokesman ever for the city's tech and entrepreneurial community when Rahm Emanuel-- the best big city mayor in the country, bar none--announced that he would not run for a third term. Good news for him and his family and really hard news for the city. Family first. Period. 

In his brief announcement, and in the comments and interviews that followed, he offered some important lessons for us, and especially for the pack of losers who had already lined up to run against him. If it wasn't so sad for Chicago, it would be comical watching these one-issue, nichy little nobodies gripe, posture and position themselves as hopefuls and aspirants to a position many miles beyond their abilities. Imagine seeing a group of 10th grade Pony league pitchers trying to throw shade at one of the MLB pros. If you want to beat Babe Ruth, play him in golf, not baseball.

How painfully easy it is for the challengers to complain and criticize from the sidelines.  I call these people solution-less soreheads. And considering that most of them are presently gainfully unemployed, I'm reminded of the old crew expression that the only one in the boat who has the time to complain is the one who isn't rowing hard enough. I'd feel sorry for most of them because of how sadly deluded they are, but their rank arrogance in thinking that even for a moment any one of them is up to the task makes it hard to sympathize with their stupidity.

The media mavens and the other scriveners realized (grudgingly admitted, is a better way to put it) that a tremendous amount of important work got done in the last seven years and that most of it wouldn't have been accomplished without the pushing, prodding, pleading and insistence of the mayor. Substantial improvements in affordable housing, expanded access to public transportation, and the conversion of the Chicago river from a sewer to the spectacular Riverwalk are just a few of the initiatives that will serve the city well long after his departure.

Sometimes a song says it all and no one ever summed up this sad situation better than Joni Mitchell in "Big Yellow Taxi" with the line: Don't it always seem to go that you don't know what you've got til it's gone. People who are even a little bit in the know know exactly how devastating a blow Rahm's departure is to the progress of any number of ongoing projects and business opportunities. This announcement may be the end of any number of new prospective investments in the city unless someone with real credentials and serious skills steps quickly into the breach and offers some serious prospect of stability and continuity. No one likes uncertainty and change less than long-term investors and institutions.

But, one of the succession difficulties is likely to be that the most qualified new potential entrants have, at best, a complex relationship and a mixed history with Emanuel. His own entry into office was aided immeasurably by a warm handoff from the departing Mayor Richard M. Daley. Of course, that hearty handshake was accompanied by a bucket full of hot messes which Rahm spent years trying to straighten out, with substantial success. No other mayor ever endeavored--much less succeeded, in large measure-- in cleaning up Chicago's decades of mismanaged and underfunded pension plans for police, firefighters and teachers. No other mayor grew the city's tech sector by tens of thousands of jobs year after year and made Chicago the nation's leader-- five years running-- for corporate headquarters relocations. And no other mayor expanded the public-school day and school year so that by graduation, Chicago public school students will have spent more than two additional years in class than when Emanuel arrived on the scene.

No one expects a similar amount of support from the 5th floor of City Hall this time around for virtually any of the major undeclared candidates, at least at this point. Of course, politics makes for strange bed-fellows, so I guess we will just see what happens. But, apart from the politics and the befuddled state of the city at the moment, there's a very important lesson for prospective entrepreneurs as well in Rahm's parting comments.

Being the boss means doing it ALL. Every day. All day. You don't get to pick and choose the fun parts. You don't get to delegate the hard conversations or the ultimate responsibility. And you don't have to shoulder the disappointments when people let you down or the hurt you feel when you suffer alongside the families and the kids who you wish you could have only helped a little bit more.

Only a few special people are up to jobs like this - be it mayor or CEO. A lot of folks kid themselves into believing that this is what they want to do with their lives, but they have no idea of how all-consuming and enervating a task it is. And what it costs in terms of your personal life and health and the lives of your family.

My advice to every aspiring entrepreneur is to be very careful what you wish for and do your homework before you take the leap. Seven scars are just the beginning. The occasional highs are okay, but the inevitable and continual lows are brutal.

My advice to the clowns so far who are seeking to succeed Mayor Emanuel is to do yourself and our city a favor and keep whatever day job you may have.

Published on: Sep 11, 2018