The long process of evaluating my life – and how it lead here

Now that I’ve gotten this topic off my chest, in a few days to a few weeks (no promise exactly when, but I always do what I say I’m going to do) I’m going to revisit it and start making it funny. If you can’t look at your history as comedy, you’re doing something wrong! People’s “stories” aren’t that interesting until they actually become a story. I’m looking forward to my own next draft.

In 2006, after working in tech for a number of years, I finally got to the point where I really wanted a career change. I was working full time, on my way to graduating with a Bachelor of Liberal Arts when I made my first visit to Denmark, ever. I came back to ask for reduced time and was laid off, so I thought mixing my enthusiasm for Scandinavian cinema with my interest in project management and finance could be used for helping more Scandinavian-Canadian co-productions get made.

When I began this change, I got counselling at an organization that specialized in youth employment. I was warned about how difficult career changes could be. And as you can expect, working with people in the HR and employment support industry always involves aptitude tests and industry code searches and analysis that, as a “multi-passionate” person, just didn’t work for me. (Also, some of what I was interested in was only emerging – and without concrete paths to success, early adopters can get bogged down by obstacles.) I do think such counselling has gotten better with time – this was 2006, when employment stability was a bigger assumption than it is today – but one-size-never-fits-all.

So I took what I could out of the counselling while I dabbled (and hustled) in film for a year. It turned out to be a regrettable experience. I’ll sum up the bad part with: not everyone in film is there for the wrong reasons, and only a few are really bad people – but the industry – and Harvey Weinstein – has a reputation for being abusive for a reason. In fact, a person who advised me against going into the field was hands-down the worst case scenario of what a new recruit might expect. So expect it.

That guy notwithstanding, I had positive albeit eye-opening experiences. There are probably more than a few companies where you do want to “see how the sausage gets made.” I enjoyed being on film and being on film sets and I met many fine people, but the closest I got to my aspirations beyond taking a production finance workshop was running a fan site for Mads Mikkelsen (who I met at the TIFF, and two years later, met his manager when I went to work in Denmark for a year).

Enter a new obsession with project management and productivity

2006 was also the year I discovered the now-defunct website 43Things. It was the beginning of a phase of reading too much about productivity starting with GTD (Getting Things Done) and all the spin-offs and software tools that emerged out of that. My Experiment in Productivity is about my prolonged and unsatisfying romance with GTD.

In September 2007, after my year of dabbling was done, I took a temp job at a multinational in the Business Development department and I started taking International Business at McGill’s School of Continuing Studies. Over the next two years, my work went a little this way and that way, including a lovely sabbatical in Denmark during the height of the finance crisis.

While I was in Denmark in the summer of 2009 – after having an experience I’ll explain in an article here at a later date – I finally saw clearly that I was not using my time wisely nor accomplishing my goals. Having multiple projects and aspirations was not fighting my “ADHD” (I’ve never been diagnosed; I believe it was an enthusiasm for learning, coupled with a few bad work habits and the intentionally addictive qualities of social media, which people are now more aware and prepared for). I was executing busy-work and I wasn’t prioritizing properly. And my runway was running out.

So I postponed some of my changing aspirations AGAIN, came back home, got another temp job, and resumed my International Business studies with the intention to complete them before pursuing new avenues.

In 2010 I graduated from my program (where I got A- in both my electives for Fundraising and Corporate Philanthropy and Project Management: Tools and Techniques). My temp job (at a different organization) ended that September, and then I had a prolonged job hunt for a non-profit management position that ended…


It was still a bad economy out there (the first time I graduated from uni also had bad-economy timing – something that’s been studied and shown to negatively affect cohorts’ earnings and professional outlooks for life). But regardless, I messed it up by not following the right mix of things to do to get a job. I was caught up in the busy-work trap again. And I became so totally demoralized, it made me question whether my career choice was what I really wanted. “After all, people much better than ME have a hard time…” (Don’t compare yourself to others. It’s unhelpful to put yourself down. They are not your competition.)

Then I got a tentative offer for a project in the US, so I rented out my home to someone I knew. But the job didn’t pan out; it was really not the right fit, so I had to come back.

Perhaps this is where my journey really began.

I spent that summer in a cabin in the woods in the middle of Eastern Ontario. I took the detritus of 20 years of inhabitants’ summer occupancies and cleared it out as much as I was permitted. I started blogging about the things that interested me (biophilia, basically). I conceived of a local-resources-reliant artisan craft school I named The Resiliency Commonwealth. I created a vision for it, and then freaked out that it was way bigger than me and the resources I had.

But it was a beginning of thinking of entrepreneurship, and taking responsibility for creating things to address gaps that aren’t being adequately served.

And it was also the period of time where I found a book in a box left on the street, Life By Design, and I started doing a life evaluation. This and subsequent iterations (What Colour is Your Parachute; Finding Your Own North Star) became part of my process that created Life’s Battle Plan.

And finally, after 5 years of practice, I admitted that GTD and project management tools were counterproductive for me. There’s something about task managers that tricks you into thinking you can take on more than you really can. I am sure someone’s written about this, and when I find it again, I’ll bring it back here. So I had to stop relying on systems, understand more about how I actually work — not how I’m supposed to work — and trick my brain into behaving better than it was. I also had to stop wanting so much out of life, life couldn’t possibly deliver.

I’d like to say “the rest is history” as if were a direct arrow from there to here; time may be, but it’s been 8 years since 2011 and a lot’s happened since. The following summer, 2012, was the time of the story I told in “Why I created Life’s Battle Plan and the Tactical Chronograph - and how they’ll help you.” And creating Projectica, both the self-management stuff and the intention of becoming a project collaboration platform, is sourced in these experiences.

What this is, I suppose, is testimony that you can form a concrete idea, stick it in an archive folder with a label called “the Future,” and start building it when it becomes compelling for you. Sometimes you might even take one of those Future projects and drop it with a sigh of relief. What’s come up over and over in all that I’ve seen and read about achieving goals is that to do more, you have to do less. So while fresh ideas are great, you can predict or decide which ones will pass the test of time, and which might grow stale, and choose accordingly.

Exhuming my past has a time-audit benefit for you:

By early 2011, during the still-active job-hunt phase of the year, I’d read an article in Canadian Business about having 168 hours in the week — how well do you use them? I created a spreadsheet to help me audit this time, and then I converted it into an OmniOutliner template that I sent to a number of my friends over email:

While you probably shouldn’t spend precious time logging how you spend your time (though there’s nothing wrong with that), it’s part of the job if you bill for your hours. It also helps to do a time audit of a week in order to see how you can find the time for a new project or job. Ramit Sethi recommends doing this, suggesting you can save 1-½ hours a day if you automate, delegate, or dispose of certain time-consuming tasks.

As a side-note, because of that Canadian Business book review, I discovered the work of Laura Vanderkam – someone I should interview:

You can download the OmniOutliner template that I created in 2011 here: 168 hours Audit Timesheet – once it’s filled out, you can export it to CSV for further analysis in a spreadsheet.

And if you want one with more contextual promptings to help you account for blocks of time (not every half hour of the day!), try this Time Diary spreadsheet (also in OmniOutliner).

Check out this post I made about it:

If you like this blog post and want more of my personality, stories, and things I’m sharing to get sh*t straight (blunt talk happens every once in a while), subscribe to my bimonthly newsletter.

– Jane

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