Blog: Back in the (office) saddle, and I launch a new series

People often ask me, “What’s your ultimate goal for Deft Communications?” which I suppose is an honest enough question, but never fails to make me laugh both because of how boring and seemingly unambitious my answer is.

Here’s my honest answer: All I want is for Deft Communications to do well enough to where I don’t have go crawling back to corporate or chain myself to a desk ever again.

That’s it. That’s all I want. I’m not interested in growing the company to be profitable enough to where I can sell it. I don’t want to build an empire. I don’t want to take over the world. I don’t even want employees. I just want to do the work I’m good at, make good enough money to support myself and my family comfortably, and never have to be fully beholden to a company or a direct supervisor ever again.

Some people relate to this, most don’t. But if you’ve worked hard enough to create your own business and you’re bound by nothing, why would you immediately want to create a brand new set of walls for yourself surrounded by the structures you just escaped? If I do it right, I’ll be very surprised if you see me working in an office again.


A couple of weeks ago I started working in an office again.

Granted, I’m subcontracting at a creative agency serving as an interim Account Supervisor for a woman who’s on maternity leave for the next 12 weeks and only working about 25 hours a week in their physical office. But you can rest assured those pesky facts didn’t prevent me from getting flush with anxiety and feeling existential dread about it in a way I haven’t experienced in the last two and a half years. There are two reasons for this.

1. Nothing makes me panic like the idea that my time does not belong to me. I’ve always hated this feeling since I was a kid. I understand there’s always shit to do, and sometimes that shit comes with a schedule. Fine. I remember the first day of grad school orientation when our advisor said, “We own you now.” I freaked right the fuck out, called my parents who were at dinner and expressed concern that I made a mistake, and then got lights out drunk.

I grew to resent this management philosophy profoundly in my brief time working for the energy drink when my boss not only wanted to tell me what to do, but how do it and when. And then I finally got so fed up with the lame, mandated presenteeism of corporate culture that demands you be at your desk for certain hours of the day no matter how much your actual job dictates work outside of business hours, nor how busy you actually are, that I leapt into the unknown and the high-risk, high-reward world of solo entrepreneurship.

I fear nothing about working my fucking ass off. I pour my blood, guts, heart and soul into my projects. Just don’t tell when, where or how I have to do it. I will get it done. I don’t need you or anyone micromanaging the process, thank you.

2. Like any normal thinking person, on some level I’m afraid I’m a fraud. I haven’t worked in an agency in seven years. I haven’t worked in an office in nearly three. Am I going to remember how to do any of this shit? Compounding the issue is that the types of campaigns this particular agency works on are outside my usual area of expertise. So not only was I going to have to get up to speed on subject matter, but I’d have to reacquaint myself with the rhythms and norms of working in an office again, too.

Neat. Time for a panic attack!

But, like I mention (probably too often) on my podcast, Lorne Michaels always says Saturday Night Live doesn’t go on because the show is ready, the show goes on because it’s 11:35 on Saturday. So, with a semi-frantic text hitting my phone one night a couple of weeks ago from the woman I was to replace who was headed into labor, I walked into my new office underprepared, full of nerves, and armed with three WWE action figures (Tyler Breeze, Sami Zayn, and Neville) to make me feel better and catch my new colleagues off-guard.

And like the first day of any new job where you parachute into an environment where people already know each other, you’re disoriented and almost childlike in your uncertainty. “Where is the bathroom?” you wonder, hoping your new colleagues aren’t secretly aliens who don’t require a bathroom, and will now make fun of you for such a fatuous request.

Everyone knows each other. They have a shorthand way of talking. Jobs you’re just now seeing for the first time have their own code words among those who’ve been doing them for months. You feel like everyone’s looking at you when you walk to the kitchen to get a glass of water. You wear your self-consciousness like you’re covered from head to toe in fish guts.

Or, at least I do.

And here’s the part where I recommend that everyone talk to a therapist regularly for at least a few months because you’ll learn more about yourself than you ever thought possible. I used to think I had a hard time making new friends. Turns out I don’t. This fact surprised me, and when I told my therapist it did, she asked me why.

And I said, “Because reflecting on it now, I realize everywhere I’ve gone I’ve made friends really, really quickly. But it always felt like a really long time.”

And without turning this into a full-on therapy session, let’s just say she pointed out to me that when I feel my feelings, I tend to REALLY FUCKING FEEL my feelings.  And since change is tumultuous even for the best of us, when I’m in the thick of a transition like this one, my inner monologue, that sounds like what I imagine an asshole big brother sounds like, gets its volume turned all the way up and anxiety radiates in my bones to the point I feel like my skeleton is going to leap out of my body and start running down the street like a methhead on fire.

And then I work here for like a week, get a couple of positive internal reviews on some work product I create, and it’s all fine! Did that stop me from wanting intensely to start smoking again? It didn’t! And yes, this company is highly structured with a lot of internal reviews and deadlines, but as someone parachuting in, that’s actually helpful. I normally wear internal bureaucracy like a burlap sweater, but shockingly, I’m subcontracting for a company that actually knows what it’s doing, and makes all the seconds of their day count. There’s shockingly little wasted motion, and I greatly appreciate that.

It’s funny because I believe the idea that we know ourselves well at all is a total myth. It’s easy to spot in people if you’re open to the possibility of it being true. But it’s always harder to turn the mirror inward and remember that I don’t actually know shit about myself either.

Because here I am two weeks into my gig at this agency and I’m enjoying working in an office! I know! Does that mean I want to go back to this full time? Of course not. But is it reassuring knowing this boogeyman of working in an office I’ve created is largely stupid and overblown. You bet it is.

Get out of your comfort zone. I did, and I’m enjoying the hell out of it.


Now then, on a practical note, this means my show needs to evolve for the time being. Working these 25 hours in an office each week while still doing the work of my existing clients and tending to my most important job of father and husband means scheduling interviews has proved nigh impossible. I have literally no bandwidth for my show in its traditional format, so let’s do something different.

One of the reasons I started this show was because I myself have had some weird ass jobs. And as a young man just taking these jobs largely for pocket money as I worked my way through school, I found myself fascinated by the people who survived off these gigs or made them their careers. There were some good folks, some incredible dickheads, and some undeniably strange cats along the way.

So here’s where the Jon of All Trades Podcast is going. Between now and February, I’m bringing you a series of solo episodes, each one dedicated to a different job I’ve had. I love stories about the journey, so why not bring you mine?

We’ll cover everything from my very first job working in the bindery of a printing company to my short stint selling painting estimates door-to-door to getting paid $1,000 for a week’s work in Alaska one summer in college all the way up to and including my stint in corporate.

It’s been more than a minute since I’ve done a solo episode, and since I ask my guests to be candid with me each and every week, I figure I owe it to you to give you a chance to look through my keyhole for a change, too.

First episode is coming next week, and we’ll go in chronological order until I’m back next year with fresh guests. And we’ll start at the beginning as 16 year-old me spends a summer working in a hot factory.

I’m excited to bring these episodes to you, and I hope you enjoy listening to them. See you then!

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