For some context, you may want to read my previous post about quitting my job.

I am homeless and unemployed in probably the most priveleged meaning of the terms. Both states of being are choices I’ve explicitly made. From what I’ve read, I’m not really on a sabbatical, but I’m on a Career Break, except the homeless aspect of it is not as conventional.

So here are the reflections:

Where Am I Sleeping Tonight

On September 1st 2012 I gave up my awesome apartment in Calgary as I prepared for an assignment in India (without really knowing where I was going after that). I changed my mailing address to my brothers place and really didn’t feel much had changed. I had already been travelling weekly for my work assignments since April 2011, and I picked up my life and departed Vancouver to Calgary in January 2010.

In the last month I’ve spent 13 nights in different beds. One of those nights was part of a 30 hour trip from Johannesburg to Vancouver, and another night was one where I lost my dignity in Vegas (ask me to show you the scar one day). I’ve learned there’s a lot of overhead in figuring out where you’re going to sleep (and I have it easy compared to those who aren’t homeless by choice).

What’s hit me those most is the disappearance of the sense of belonging. For 8 months I “lived” in a Residence Inn in Bellevue, Washington and it was as much of a home as anywhere. I belonged there, had my routine haunts, and knew where I was going to be for weeks on end. Nowadays I’m either imposing on friends and family, or spending too much for a hotel… ok, and using home sharing websites which is like a hybrid of the two.

So I guess this break has been successful in teaching me something already. I need to find a place to live. I do like the traveling lifestyle, but only when I have a home base.

Talk Talk Talk

For some reason, this first month break started off strong with lots of conversations with people in the tech industry. Maybe I was seeking the familiar so these conversations fit in my comfort zone. I’ve probably spoken to over 10 or so companies and am journaling my pursuits as I go. I’ve added a constraint on my life that I won’t work for 6 months so it’s hard to not jump on what seem to be great opportunities.

No Startup For Me

As a technologist, I’m passionate about open standards and infrastructure that makes the Internet work. The last thing I would want as a startup is for my company name to be a verb (eg: Uber, Tweet). Technology like: SMTP, HTTP, HTML, DNS aren’t corporate brand names. I like to live in abstractions, and as a business owner, I think that’s probably the worst characteristic I could probably have in order to be successful.

In fact, I’ve challenged myself to minimize the brands names I speak unless it’s trully an endorsement for the brand. Here are some of the translations I’m attempting to do:

• Tweet -> microblog
• Uber -> rideshare
• Nexus 4 -> phone
• Coke -> cola

Marriott, on the other hand, is a brand I’m happy to publicly endorse.

So yeah… given that one aspect of success for a startup is something I’m not advocating, I think it’ll be hard for me to be part of a startup. Though, I think this really depends on the state of the startup.

I’m Super Lucky

Part of what has made this break possible is the amazing network of friends and aquaintances I’ve made over the years. There are couches available to me all over the world and that’s something I feel super blessed about. I really have to thank ThoughtWorks for enabling me to meet people from everywhere and make these connections.

A Hint of Concern

You would think after 1 month of not working I would feel stress free. For some reason there’s still a hanging anxiety. Part of it is probably my first point about finding a home. The other is that I feel there’s something bigger that I should be doing. Being in Vancouver for the last little while has sparked a stream of nostalgia and reflections on a simpler and a more naive past.

Familiar is Good

This probably isn’t a surprise to anyone that knows me, but I’m a fan of the familiar. When I drove down to Seattle, I visited Ooba Tooba and Bathtub Gin. In San Francisco I went to the White Horse Tavern. Anytime I go back to a place I haven’t been to in a while, I favour hitting the familiar places rather than trying something new. This is clearly part of who I am and find it something I can’t negotiate.

Summary

I have no idea how to summarize anything right now. The focus is on data ingress and going to delegate the analysis to a later time.

• career break