Two Years On My Own (But Not Alone)

by octopushat

My 2-year anniversary of quittin’ the ol’ day job passed with no comment late last month. It’s been an adventure to say the least and more challenging that I imagined (and I am damn good at imagining all kinds of insurmountable challenges).

Overall, there’s nothing to complain about – or at least nothing that isn’t greatly outweigh by a corresponding awesome aspect of this grand experiment. The lack of a real, weekly paycheck was, of course, the biggest adjustment. Without going into financial details, the shift from a annual salary to a ad-hoc scramble for duckets would not have been possible without the support of Jules and some considerable sacrifices on top of that. Like retirement. I’m going to be working the word-mines until the singularity at this rate. (But that’s okay with me.)

Eventual that big red “outgoing” number will get smaller than that erratic “incoming” number. Or I’ll smack into the fiscal event horizon. Whatever. When you have the luxury of not working for a paycheck, money carries a lot less weight.

The real challenges have been more subtle than that.

Self motivation and staying on-task is my biggest day-to-day struggle. No real surprises there, but what is surprising is how insidious my own self-defeating tendencies can be. The twin-headed dragon of self doubt and procrastination feeds at every opportunity. Every crumb of slothfulness or uncertainty or distraction fuels the dragon, and deadlines are its favorite time to sow chaos.

Fuck that guy man, he’s the pits.

Speaking of slothfulness – it’s shocking how much exercise one gets walking from a parking spot to the office and then around the office for 8 or 9 hours. If I’m not careful, I’ll plop my ass in this chair and won’t move much off of it for 8 or 10 hours. I got a pedometer a while ago to track my physical activity (data! fuck yeah!), and the general consensus for a non-sedentary lifestyle that will lead to happiness and enlightenment is 10,000 steps per day. Every day.  Sneaking a peek at my Fitbit now – at 5:17pm on a fairly unproductive Thursday – I’ve got 792 steps. (and I bet 100 of those were from after midnight last night). I like to say that the office job was killing me, but this writing from home thing might be even worse for my health.

The pedometer and personal data hints at another challenge – metrics and tracking. I like to see progress. I like graphs and charts and performance numbers. It’s tough to track your progress on doing your own thing when you’ve got no metrics to track. I’ve played around with using various data points as an indicator of my performance. Page views. Facebook likes. Words per day. Klout score (it’s okay to roll your eyes at that one. I do).  If I spent some quality time on an algorithm that aggregated all these individual metrics, I could probably come up with a trackable number that would provide me some insight in my day-to-day performance. Of course, that time spent in development would be a tasty meal for the two-headed dragon…

All these other challenges are really secondary to the isolation. I miss coworkers, social interactions, and – even – bosses. Sure, I could cowork, but that seems like a step backwards (and – to continue a strained metaphor – it seems like lowering the drawbridge when there’s dragons about). I make-up for some of the social deficiencies with instant messenger and a few regular conversation partners, but it’s no panacea.

More importantly that that even: I miss having a mentor.

I’ve gotten a lot from relationships with various mentors over the years, and even when I haven’t had one, I’ve always had a boss or superior who I could turn to when I was hard-up. This going-it-alone thing is tough! All external insights (there’s got to be a better way to say that) and advice and cautionary tales that I want to rely on for growth have to be discovered in the wild. I can READ about other’s experiences, but I can’t get real advice or guidance on what I’m doing and how I can do it better.

My buddies at Lifehacker touched on how to find a mentor a few times, but it’s always in a context of employees.  After two years of making do without, it’s my lan to now actively seek out someone to fill this role. If you’ve got any advice on where to start, I’d love to hear it.

Two years ago I bailed on a steady, well paying 9-5 in a field that I was able to keep interesting to “become a writer” – my dream career for as long as I can remember. Eighteen months ago I launched Beer of Tomorrow with the goal of making it the best craft beer website in Los Angeles. Six months ago I shifted focus from my site back to freelance writing, and now I guess my goal is to be the best beer writer in Los Angeles.   My question now is how do you measure that?

That was 45 minutes of procrastination-by-writing (the only kind of procrastination that doesn’t fuel the two-headed dragon). Now I’m going to go for a run and see if I can’t get this fucking pedometer off my back. 

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