This is a reflective post. No real content, so if you aren’t a friend or don’t really care what’s going on in my life feel free to move on. I’m a blogger, I’m allowed a narcissistic post once in awhile! What follows is a fictitious timeline of some of the things that’ve been going on in my head over the last few weeks.
25 July, 2009
Woke up. Realized I was about to leave my baby, my team and my family behind. Panicked. Ate poutine. Panicked. Ate ice cream. Passed out. Panicked. Wrote emails to team, bloggers, partners, etc. Scheduled to send out on 27th. Felt like shit. Ate more ice cream.
26 July, 2009
Didn’t sleep last night. Probably won’t sleep tonight. Oddly feeling okay with that. Feeling like maybe I deserved to be punished, and not in a good way. Flying out to begin my “workcation” before shit hits the fan with my quitting. Want to be “on the ground” and away from Toronto when it happens.
27 July, 2009
Wow, okay, wow. My two biggest fears were that a) nobody would notice I’d left and b) that I’d get absolutely lambasted. Given TechCrunch/WSJ/NYT coverage (and lots more besides), clearly A wasn’t an issue. And outside of a douchebag or two and a few disgruntled ex-employees B wasn’t an issue either. Spent about 4 hours dealing with the swell of coverage.
Then I walked away from the computer for the afternoon. Figure I might as well practice this workcation thing sooner than later. When I came back, there was stuff to respond to, but what had to be said had been said.
30 July, 2009
Came back online to find hundreds of emails, tweets, DMs, etc either offering support, jobs or saying “we should meet”. When pressed on what we should meet about, response is invariably “no, really, we should meet”. Wondering if folk actually think I’m in the mob due to new branding around the consulting agency.
3 August, 2009
Head to visit best friend in Raleigh for a week. Manage to “catch” epic allergies. Like 6 drugs and still doing 2 boxes of kleenex a day type of allergies. Don’t sleep much. Spend no more than 3 hours a day online. 1 hour catching up on client stuff, 1 hour on leaving b5 stuff and 1 hour trying to figure out whattf I actually want to do!
5 August, 2009
As is a 10-year tradition, I continue to beat my best friend senseless at football video games. This despite the fact that he nearly went pro and feels football in his bones and that I actually have no clue how football even works. I mean, come on, they’re running … why can’t a touchdown be called a home run? Geeeeze.
Realize that it might be easier to figure out things I don’t want to do than things I do. Ponder this over the world’s best burger and fries. Come out with the fact that I don’t want to:
- Become a hairdresser (my hands shake)
- Start another bootstrapped startup (a revenue generating or funded startup is fine… and I’ll also almost certainly do a from-scratch startup at some point in the future… just not now)
- Move to LA
7 August, 2009
After getting plastered with best friend’s buddy (who spent most of the night trying to explain to me how to make a coke-can bong), head back to best friend’s apartment, with new buddy, to play more football. Lose a game to best friend. Kick buddy’s ass in ways that won’t be repeated. Realize I also don’t want to move to Dubai to lead the “North American Strategy” for a major UAE media holding company. As insanely cool as that’d be (if for no other reason than regularly being able to fly in one of those wicked tricked out planes, first class), I’d be too far from my boys, which I’ve decided totally ain’t cool.
9 August, 2009
On plane on the way to London, UK, to visit friends, realize I also don’t want to join a big media company in a “strategic” role (big paycheque = nice; politics all day long = not so much… I’d rather Get Shit Done). That said, there is a very large, very strategic role, in a media company that I’m holding out for.
11 August, 2009
Much drinking, much relaxing, much curry make me realize I’m gaining weight. Decide I won’t care until I’m back. Entered workcation at 225 pounds. Currently over 230. Realizing that I do need everything in moderation, including weight-loss. At least right now.
12 August, 2009
Wake up for the first time without any stress at all. It’s taken me 2+
weeks to let all the stress from b5 and changes and stuff wash off of me. Realize that 2 weeks isn’t really that bad given marriage failing, taking 60%+ pay cut, leaving job, handing baby over to new CEO, new girlfriend, boys getting older way too fast… This sense of “relaxing” (new word to me) comes and goes over the next two weeks.
Some days I hyperventilate with stress, some I don’t even get out of bed. It takes until the 18th of August for me to actually stop this cycle of up/down-ness. My therapist (how weird is that to say) is confident I’m coming out of the “valley”.
16th August, 2009
Last night in London, and I decide not to get drunk. Realize I often used to get drunk to destress. But since I’m not stressed, I can just go chill with friends. We catch a movie, chill, and just “hang” (a foreign concept to me) until the very wee hours of the morning. I get lost on the way back to my hotel, confusing Leicester Square with Covington Gardens. Thankfully a bum is more than happy to walk me to my hotel in exchange for my watch. Very kind of him. Joke’s on him, it’s just a spiderman watch.
- Image by Eneas via Flickr
22 August, 2009
Preparing to head home, after more workcationing while landing a new client, gaining weight (232 at last check) and starting to book meetings. As I book meetings and figure out what excites me, I realize they all have a few key things in common. They all:
- Involved being entrepreneurial, even if it was inside a larger company or an agency
- Involved Getting Shit Done, whether by leading products/projects or by helping clients get Big Wins
- Had freedom and flexibility to do conferences and such, assuming they add value and that I’m continuing to Get Shit Done
- Had me learning something I’d never done before
- Were local (ie: no further than NYC/Montreal/Ottawa). I have 2 boys, and don’t want to be any further than that from them
24 August, 2009
Arrive home in Toronto after hellacious travel home, involving missing bus. Missing another bus. Then paying 200$ for a cab ride home cause I just didn’t fucking care anymore. Intend to sleep. Can’t sleep. Intend to clean. Don’t clean. Decide to go out to local party to actually show my pretty face. Am honestly unsure if anyone will care. If they do, should they? If they don’t, should they? Decide to just hang with friends, not let the stress creep up on me and not get drunk. Cause, y’know, I don’t need to cause I’m not stressing.
Party starts slowly, but picks up once I steal @verneho’s nametag and wear it around for an hour. He doesn’t realize I have his nametag, even after we go “searching” for it together. Even after taking pic with him and I in it, me wearing his nametag. Pic is epicly good. I’m gonna have it bronzed. He still claims he knew the entier time. Riiiight 
Night was great. Folk seemed happy I was back. Convos with friends were great. Ended the night when someone convined random chick it was my birthday. Also convinced her my name was Jorge. Pronounced “Whoregy”. She sang “Happy Birthday Dear Whoooooregyyyyy” twice too often.
27 August, 2009
After nearly 20 meetings last week, and half a dozen offers, I was able to trim my list down to 5 positions. Each of these are exciting in some way or another, each of them are more than just “a job” that I’d take for a year, and each of them are with companies and teams that I could invest myself in in a real way.
The positions are everything from EIR in a VC firm to leading a digital media agency to taking the helm of a startup that’s about to raise funding 
and that I really believe in, in a space I love.
Now
So why write this post? Mostly because I’ve talked to a half dozen people over the last two weeks that are stuck on the “what do I really want to do?” question. So I thought I’d share some of my ruminations. Because while blogging’s matured and become less freeform over the last few years, I figure as an “old timer” I’m allowed to occasionally just freestyle it. Maybe no value to anyone but me, but yeah.
Lessons I Learned While Gone
But, seeinng as how blogging HAS become more polished, I figured I’d share some lessons I learned while I was away on workcation:
- Figure out what makes you smile, and do more of that
- Figure out what makes you stress, and do less of that
- Don’t be afraid to fail (I used to live by this, but sometime in the last year I lost it)
- Sleep
- Friends and family matter
I figure if I can’t do/have those 5 things in a job, it’s not really worth doing.
I also learned that girls in New Orleans still flash their boobs, even if it’s not Mardi Gras. And it’s generally not worth seeing. Girls Gone Wild has skewed the number of hawt chicks flashing in New Orleans. It’s fiction! Fiction I tell you!
Anyways, it’s great to be back. This week will be a week of decisions. But more importantly, this week is a great week to practice balance.
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