Take a break from electoral politics, Adam. You've worn your heart on your sleeve about your political aspirations for a long time and it's not too late to still become prime minister (or perennial NDP leader as the case may be). At 32, you have plenty of time to pursue this goal, and maybe even become premier of Ontario along the way.
But now is the perfect time to catch your breath. Resign as TTC head and don't bother running for councillor in the next election. In your ward, you are not the most popular person right now (for pesky issues, I know, like the Queen Triangle debacle, the narrowing of Lansdowne, for parking on Dundas, but these are issues dear to the hearts of voters). Losing the next election would add insult to injury. Step away from the ballot box.
Your early fresh-faced entry into electoral politics proves the maxim about power corrupting.
(Disclaimer: I don't think a promiscuous person is a corrupted person. My qualm is cultivating the public image that you're single and available (how else was Now able to mistakenly presume you're gay?), then parading a quasi-wife figure when you announce your candidacy for mayor--as if that's even necessary in this day and age--then, when confronted with the facts of a sexual relationship with somebody other than your quasi-wife, lying about it. Toronto could have easily handled--perhaps even celebrated--a swinging single mayor. It's the role the women were cast in that's off-putting. If, with the support of your quasi-wife, you could have replied to The Toronto Star allegations with a confident "So what?" you wouldn't be hiding out in Italy this week.)
So here's what to do. Spend the next three to five years doing something else. Something that will make a difference but is somewhat under the radar. Run the United Way. Get involved in some green-energy company. Do an academic fellowship for some kind of centre for innovation. Show that you're not just a smarmy politico but someone who has the smarts to solve real problems and deliver real tangible results. We can debate forever whether the TTC would have been better off or worse without you; it was a major mess and remains a major mess. Grab hold of a project that will show success within five years, something manageable enough that the success will show your signature. Pick something close to your heart that shows you really care about the work, not the public attention it gets you. If you're out of the headlines for a few years, so much the better.
After people have all but forgotten your time as city councillor, run for provincial or federal politics with a campaign that demonstrates how much you've learned from your time in the private/not-for-profit sector. Tap into that newfound wisdom for political problem-solving strategies.
Hey, it worked for former Winnipeg mayor Glen Murray (who admittedly wasn't trying to leave behind any taint other than being non-Ontarian) who just became an MPP at Queen's Park. His time as president and CEO of the Canadian Urban Institute was not wasted. Yours won't be either.