On Running for Office, and What’s Next?

Permit me a bit of narcissism. This post is all about me.

As many of you know, I ran for Winter Haven City Commission in 2015. Here are a few things I learned, pro and con, perhaps to help guide the next person who might consider going down that road.

Pro: Support will come from places you did not expect. Looking at my donor list is humbling. My list of supporters includes a lot of people I am very proud to have had on my team. People who knew nothing of Winter Haven other than (perhaps) where it is on the map even sent me some money or helped stuff envelopes because they believed in ME. I am especially proud of endorsements I received from the local firefighters union, the East Polk County Association of Realtors, and James Hogan, one of my opponents in the initial election before the runoff. If you are in the right place, people will support you. Running for office is good for your ego. That’s good, because…

Con: To win an election, you need an ego of psychopathic proportions. Nothing else can sustain you through the long hours of work. I’m not sure I have the level of ego it takes to be a successful politician. Our process does not reward humility. Successful politicians know, beyond any doubt, that they are Divine Providence’s greatest gift to humanity. Doesn’t that explain a lot about them?

Pro: Running for office is fun. It’s the ultimate “all-in” experience. You will think about nothing else from the moment you awake ’till the moment you fall asleep (if you can sleep at all). I especially enjoyed knocking on doors, and I didn’t expect that. When I was feeling down, spending an afternoon knocking on doors always perked me up. People will respond to a positive, enthusiastic message, and most of them genuinely appreciate that you care enough to show up.

Con: Many people vote for frustratingly shallow reasons. I was asked by many people lots of things that have nothing whatsoever to do with whether I would do a good job making decisions about water utilities and city employment policy. Do you support abortion? How do you feel about gun rights? Where do you go to church? I know of one person who voted for me because he hated my liberal opponent, and another person who voted for me because he hated my conservative opponent (same opponent). Neither of those two asked me whether I am liberal or conservative — they just assumed I agreed with them because I knocked on their doors. Those that did ask me such questions got nuanced answers that I am sure did not do me any favors. Sorry, y’all. If you wanted a demagogue of any sort, I was not your guy.

Pro: Even when you lose, you can influence the direction of your government. I got to see my opponent respond to my points by moving closer to my position on several priorities. Statements I made about my stance on attack ads had a positive effect on the conversation in other races. I came away from it with more connections and more influence than when I started. Running for office does not have to be something that is only successful if you win.

Con: You will be personally attacked. Early on, I made a commitment not to run negative attack ads. I did say I would point out where my opponent went wrong and contrast myself with him. At first, he graciously did not run any of those ugly ads, either, but that didn’t stop him from privately denigrating what he assumed to be my religion person-to-person with a key voting demographic. (It worked. I lost that demographic by a wide margin.) I only ever criticised his record on relevant issues — it was never personal. I was rewarded for taking the high road by seeing my face on the Ledger’s website in an attack ad claiming I broke my promise. I had sent a mailer that did exactly what I said I would do: point out where he went wrong on perfectly relevant policy issues and contrasted myself. Isn’t democracy wonderful? Even so, seeing myself publicly ridiculed was energizing, and when I ran that mailer, I knew it would anger the other side. I liked that, a little. Maybe there is a bit of politician in me, after all.

What’s next?

Many have asked me if I will run again, and if so, in two years (against someone else), or in four (against the same person, if he runs). I am not sure. To really do this right, you have to begin preparing a year or two in advance. Taking unpopular stances is a no-no. But refusing to take unpopular stances is really not my nature.

Therefore, here is my plan: I love my City, and appreciate its government. I want to do my part in its success. My website, PolkingAround.com, has not received much attention lately, and it’s time for that to change. I am going to spend more time “Polking Around” Winter Haven government, attending meetings, talking to people about important issues facing our City, and writing about them.

If my advocacy wins me enough support that another run is viable, I may consider it. But I’m not going to spend my time narcissistically gunning for that when there is other important work to be done. Winter Haven still needs me, even if it does not need me to play that particular role right now. Onward!

I really do wish Pete Chichetto the best. But if he continues to not show up at meetings of boards for whom he is our liaison, I’ll be watching, and writing. Do the job, Pete. It’s time for you to prove that you were the better choice. Step one: show up.