Climbing The Ladder

6 Questions I Wish I Could Ask My Insecure, Post-Grad Self

By | Wednesday, July 06, 2016


I work as an improviser in a comedy theater. I write plays and produce sketch shows. I rock the public libraries and cafés of my neighborhood with my laptop in hand, working flexible hours for a Certain Blog That You Might Be Familiar With. When I rattle off the various stages of my employment history, a host of socially-itchy memories come rushing back. Mainly, I remember a Groundhog Day-like spool of small talk at parties in overheated apartments. I recall how I — in sidling from conversation to conversation, clutching a glass of fortified punch — was consistently cornered by well-meaning acquaintances and their ubiquitous question: “So! What do you do?”

I remember listening to the peaks and hollows of my voice — checking my tone for signs of fatigue or sycophancy — and feeling mildly surprised by the brand of self-deprecating humor I was rapidly canning and shipping out to these acquaintances. I began by explaining my job insecurity and unusual, artistic career path in earnest; after a dozen rolled eyes, abrupt ends to conversations, and primly-restrained follow-up questions (“Ah. So…you’re an…actor?”), I realized that I would need to selectively disclose information order to beat these acquaintances’ judgement to the punch. I didn’t have “a real job,” and no amount of charming sarcasm was going to smooth over the gap between my day-to-day livelihood and that of My New Friend At This Mixer, The Disenchanted But Loaded I-Banker.

I wish I could take a magical A Train back in time and awkwardly slow-clap at my younger self while she tap-danced for the approval of her peers. Alas, Back To The Future: The Subway Edition is not an option to amend (or retroactively speed up) my process of finding self-assurance as a Haver Of No Day Jobs. Instead, dear friends, I want to share with you the crucial questions I would have yelled at my younger self from across the room of these crowded parties, over the heads of the judgy plebes.

1. Do you want a day job, or do you want the social perks of a day job?

It’s isolating when you feel like everyone around you is enjoying the security and camaraderie of the “real job” weekly schedule: out the door every morning and into the sunlight, out of the office in time for weekday happy hours, home for dinner and a favorite TV show, weekends free and clear for trips and socializing. For those working a “real job,” hangout time, vacation time, personal days, and financial activity (transferring X amount from the bi-weekly salary paycheck to the ol’ savings account) are all securely regimented by a predictable weekly rhythm; planning ahead requires far less frantic mental maneuvering. When I was working in food service, in babysitting, and in tutoring, I remember feeling resentful of all the odd night and weekend shifts I had to pick up in order to make rent. It was logistically difficult to date, to go out with friends, to get the hell out of town for a weekend visit with my long-distance best friend. After a year or two of living this way (and moving in and out of a “real” day job in publishing), I realized that a large part of my envy and insecurity was rooted in my desire for regularity, rather than the actual work that came with a “real job.”

2. Will you remember (or care) what an acquaintance thinks of your career path a day, week, or year from now?

I remember the sound of my own voice as I delivered sheepish semi-apologies for not having a “real job.” I remember battling an encroaching inferiority complex as my roommates stalked out the door every morning to join an office of coworkers who collaborated on projects and pursued team goals. I remember phone calls with my close friends: their steady encouragement of my unconventional (and often, overloaded and underpaid) work, their reminders of my larger creative and career goals and how “real jobs” wouldn’t allow me to pursue those goals fully. I don’t remember what the Judgers said over lukewarm beers during forgettable house parties; they simply put a dent in my armor for an hour or two. I soldiered on and learned crucial organizational and creative skills as I pursued my own work.

3. Are you making the most of the liberties that come with working outside the 9-to-5 framework?

The times I was the most miserable while working outside “real jobs” were also the times that I let my personal and creative needs slip through the cracks. I got sucked into incessant scheduling and re-scheduling with tutoring and babysitting clients; I stopped living outside the relentless hustle of picking up overtime retail hours during the holidays. Though I had free hours outside of work (during which I could write, or explore new neighborhoods sans weekend crowds), I wasn’t taking advantage of that free time. The “freedom” that I often cited as the main perk of my unconventional work schedule was an untapped resource. When I exercise the discipline of planning ahead (despite scheduling irregularities) for trips away from the city, adventures within the city, and personal time for creative projects, I felt infinitely more fulfilled by my decision to resist the pull of a day job.

4. If you’re grinding through a rough service job or retail gig, do you know what financial and personal goals you’re trying to build towards, beyond the day-to-day slog?

Because retail and service jobs require such intense, heated focus on what’s happening in the moment (I have five customers yelling at me because their orders are taking too long), it’s hard not to apply that tunnel vision to your life outside the shop or restaurant you’re sweating in. I had the most trouble exercising personal-life discipline (see above) when I generalized my retail-worker approach to my whole life. When I realized that short-term survival instincts had displaced all my long-term creative goals, I took to meditating and stretching for five minutes every morning. Forcing myself to slow down and reevaluate what I was truly working towards helped me break my cycle of resentment and resignation to the grind.

5. If you met yourself at a party, would you be so quick to judge your professional choices or dismiss your lifestyle?

Prolly not. Most people are genuinely curious to see how others are hacking their way through this wild world. Their questions aren’t an invitation for an apology, sarcastic deflection, or defensive evasion; they’re just…questions. People want to know what you’re up to, what you stand for, and how you spend your time this planet. I’m an incurable extrovert, so I’ve walked up to plenty of strangers in my time and broken the proverbial ice by asking “So! What do you do?” When people responded with something that I couldn’t relate to directly (I’m a construction contractor, I’m getting a PhD in biology), my first thought was never “Ugh, why would you waste your time on that?” It was: “Whoa. What’s that like?” When I reminded myself that my open-minded inquisitiveness was not an individual phenomenon, but a relatively universal one, I felt far less threatened by others’ inquiries into my hodgepodge freelancing career.

6. Do you have comrades — that is, friends who also work outside the traditional   “real job” framework — who not only understand your position, but also give useful advice as you navigate your unconventional path?

I cannot emphasize enough how important it is to find a like-minded, similarly-unconventionally-employed community when you’re working outside the “real job” industries. Everyone who works a day job in a fixed location has coworkers; why wouldn’t you require the same sense of belonging, purpose, and feedback? Humans are pack animals; we thrive on connections with other people, and we learn best from the social exchange of ideas, techniques, and philosophies. I perform weekly at a comedy theater in the city, and lord knows I find deep reassurance in the conversations I have with fellow artists and writers (who are also working in service, childcare, tutoring, etc) who are navigating all the points I mentioned above. When you’re freelancing or working single-person odd jobs, find your fellow odd ducks!


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