Yesterday’s post was a necessary look back, but I want to focus now on what’s next. As I mentioned before, I’ve taken myself away on “career retreats” on two previous occasions. In 2003 and again in 2009, I spent a couple of days in Kingston, Ontario, chosen, frankly, for its blandness and lack of distractions (sorry Kingston!). On both occasions, I returned energized and with job descriptions in hand for jobs that did not (yet) exist. On both occasions, I went on to work at those jobs after reaching out to the relevant communitites (wine and film, respectively). And I still have great relationships and potential or ongoing work with both of these communities. So clearly my strategy has been effective. The issue was that in one case (wine), the industry was too small and my prospects limited, and in the other (independent film distribution), the economy made it impossible for me to work full-time for decent wages.

Given that I would like to continue to work with the people I met in those two jobs, I’ve been exploring the idea of launching my own content consultancy. I’ve certainly worked in many different business sectors and have seen the same issues in all of them. A lack of clear communication and a need for guidance when it comes to online tools, for starters. The shape of this new business will need some experimentation and some advice from trusted friends, but it’s a potentially exciting new direction.

And just to reinforce that my basic skill set has been in place all along, here are what I listed as my “transferable skills” back in 2003. Each was based on a job I had performed at some point in my working life:

I’m a person who can:

I took the photo for this post myself. It’s a road sign we saw in rural Iceland on our trip there in 2008. I invite usability experts to weigh in on just how helpful this sign could be to anyone traveling by car.

As I write this post, I’m sitting in a San Francisco café in the midst of my third “career retreat” in the past eight years. For someone who thinks about the world of work so much, I don’t seem to be very good at figuring it out for myself.

I left my position at St. Michael’s Hospital just over a month ago, six months into a ten-month contract. Without getting into too much detail, I was unable to work effectively within such a large organization, with all of its existing power structures and areas of dysfunction. Plenty of people do, but I’ve just realized (again) that I’m not cut out for working in bigger companies.

I’ve been working for money for more than 30 years now. I took my first job in the summer of 1980, selling magazine subscriptions door-to-door. Since that time, the longest I’ve ever held a job has been four years, and that’s been on two occasions. From 1994-1998, I was a welfare caseworker for the City of Toronto. And from 2003-2007, I was the web guy for Lifford Wine Agency. I enjoyed both jobs, but left for similar reasons. I was worried about stagnating. I’ve come to realize that when it comes to work, I have a fear of commitment.

It hasn’t helped that for the past decade, I’ve been working in web-related positions. The online landscape shifts so often as to make just about anyone insecure. I’ve always been happiest as a generalist, but each job I’ve taken in the past few years has pushed me to specialize more and more. I’ve learned a lot about what I don’t like to do in the process. What’s been harder to nail down is what I do like to do.

And so I’m here, spending a week away from my regular routine, reading, thinking and writing about what I want to do with that part of my life devoted to earning money. I’ve tried to be unsentimental about work. My generation may have been the first raised to expect more from our careers, not just money but fulfillment. I’ve always thought that was a tall order. And yet.

We spend half of our waking hours working. We often see our workmates more than the members of our own families. We should be looking for an environment in which we can use all of our abilities and develop good working relationships. We should be able to balance our work and home responsibilities with as little stress as possible. Let’s face it. I’m still an idealist.

Everywhere I have worked, I have diagnosed areas of dysfunction and lamented relationships that just didn’t work out. I’ve often thought that I would make a good manager, but without the power to actually make organizational changes, I know I’d grow bitter and frustrated.

I’ve often joked that entrepreneurs are people who just can’t work with anyone else, and now I feel like I understand that mentality.

Over the past eight years, on my career retreats, I’ve compiled lists of my skills. I’ve read about flow. I’ve tried to combine my passions with my abilities. I’ve created non-existent positions and then sold companies the idea of hiring me to fill them. So why am I still back in this position, unemployed and looking for my next gig?

I’m 46 years old. I like to think that I know myself pretty well. I like to think that the income matters less than the opportunity. That I’m ready to take on new challenges, again. But I worry that others will see me as a job-hopper, as someone who’s never stayed in one place long enough to achieve mastery or to assume responsibilities. As someone who is afraid of commitment.

I often compare the world of work to the world of relationships. And I worry that I’m that guy waiting for “the one” to sweep me off my feet. And I’m perpetually disappointed. And worse, it’s not possible to take a break from working the way one might decide to take a break from dating. We need to work all the time, and when we’re working it’s hard to find energy to find better work. So many people muddle on in jobs they hate. Except me. I get out.

And as each position I leave is found wanting, I worry that I’m running out of options. Who wants to hire someone so unsure of what he wants out of his work?

So this week is about me remembering my experiences, recalibrating my expectations, rethinking my ambitions and researching my options. God help me.

Thanks to Daniele Sartori for making his photo available under a Creative Commons licence.

I’ve been needlessly secretive about the new job I started this week, and I’m not sure just why. Perhaps it’s because I’m still pinching myself. The past few weeks have seemed pretty dreamlike, with a wonderful ten-day vacation in Spain also contributing to my giddiness. Here’s what has happened.

Despite the best intentions of all parties, it was clear that my 3-days-a-week gig at indie film distributor KinoSmith was not going to turn into a full-time salaried position with benefits and vacation. So a few months ago, I began yet another round of job searching, applying for just about everything with the words web, content, writer, or editor in the job description. I was encouraged that there seemed to be more of these positions showing up in my daily career alert emails, but I wasn’t getting as many interviews as I would have liked.

Then, in early October, many weeks after I’d applied, and during a particularly quiet spell, I received an email from Anthony Lucic at St. Michael’s Hospital inviting me to an interview for the position of Website Managing Editor. It had been so long that the original posting had disappeared from the web and I actually had no idea what the job description was anymore. Nevertheless, I was excited for several reasons. First, this was a position in the nonprofit sector, at one of Canada’s leading hospitals, and I could easily get excited about working in the healthcare field. Second, the position seemed interesting and challenging: writing and editing, but also a strong strategic component, where I’d be involved in planning the direction of both the public-facing site and the hospital’s intranet. Anthony was actually the incumbent in the position and had been on a secondment to another part of the hospital for several months, so he knew exactly what they were looking for. He interviewed me by phone at first, then invited me in for a more formal panel interview the next week. Finally, the week after, I was invited back for a second (third?) interview where I met the person I’d be reporting to, the hospital’s Director of Public Relations.

All this was happening with our long-planned trip to Spain just days away. In fact, the very afternoon we were leaving, I received a phone call from Anthony just half an hour before our taxi arrived, offering me the position. It made our vacation that much more enjoyable knowing I’d be coming back to start an exciting new job. Technically, it’s a contract position, and if Anthony’s secondment isn’t renewed, he’ll likely be returning to the position next fall, but I’m not worrying about that just yet. I’m looking forward to some new challenges related to managing a large corporate website. I’m hoping that the burgeoning field of content strategy will hold many new insights for me, and I’m bemused to be wrestling with both an unwieldy corporate CMS and the tortured prose of professionals and academics again.

P.S. The title of the post and the image both reference the iconic “Urban Angel” statue that has come to represent St. Michael’s Hospital. You can read more about it here. “Thank You For Sending Me An Angel” is a very fine song by Talking Heads from their second album (and my favourite), More Songs About Buildings and Food (1978).

Won’t you please talk to me
If you’d just talk to me
Unblock this misery
If you’d only talk to me
– Peter Gabriel, “Come Talk to Me”

Last night, I went to a party. Each year around this time, Lee Dale and Jay Goldman organize a get-together just before South by Southwest, ostensibly for Torontonians heading down. Cheekily-titled Canadian Livers in Training (CanLIT), it’s a boozy, loud, and utterly wonderful time. And that’s coming from someone who’s a bit of a party wallflower. I didn’t have any deep conversations last night. I might have spoken to ten people in a room of about 150. But what it reinforced for me is that life is about connection with other people. I would argue that work should be, too.

This might sound strange coming from someone who has worked and lived online for the past decade or longer, but I think that as wonderful as computers and mobile devices and the web can be, they have contributed to much more isolation in the workplace. I’ve spent the past few years miserable in high-paying and some might consider cushy jobs writing and building “communities” on the web. Miserable because in the workplace, my day and the days of everyone I worked with consisted of long stretches alone staring at a screen and not actually talking to each other.

This might work for some among us. It’s not surprising that tech jobs are often filled by people with some form of social dysfunction, but I think I’m arguing that our workplaces reinforce and in some cases may even help create that dysfunction. I’ve certainly learned that personally, I need a job where I can spend a significant amount of my day interacting in real space with human beings, preferably smart people. It seems a gross injustice that most of the people who are comfortable around others, those with so-called “people skills” are often channeled into sales and marketing positions, forcing them to use their gifts in the service of selling more crap, while so many other people in the organization look at these folks with a mixture of envy and resentment.

I’m not saying that we should spend our work day holding hands and singing folk songs. Nor am I arguing for more useless meetings. But to me, all of the talk about “corporate culture” is meaningless if we all work alone.

To bring it back to South by Southwest, each year for the past ten years, I’ve been spending a pretty large amount of money and often taking vacation time to make the trek to Austin. Though there are literally hundreds of panels and presentations, I learn more in the hallways between sessions, or over lunch or dinner or drinks with all the smart people I meet there. Humans are social creatures, even the introverts. Somehow, our workplaces have crushed that out of us in a misguided quest for efficiency. I would argue that we’re much more efficient when we’re interacting with each other. Now, how can we make that happen? See that comment box below? Come talk to me…

Thanks to Flickr user cliff1066™ for making his images available under a Creative Commons license. The sculpture is called Last Conversation Piece, and it’s by Spanish sculptor Juan Munoz (1953-2001). It’s in the Hirshorn Sculpture Garden in Washington, DC.