A Cautious Tearaway.

Do you consider yourself a risk-taker?

I am cautious by nature, especially in my interactions with other people. I am allergic to extreme adventures like sky-diving, bungee-jumping, even rock-climbing and hot air ballooning. I will not scuba dive — I could barely tolerate snorkeling. I tend to imagine the worst possible outcome and will yank my children and even Mr. Magpie if they walk just an inch too close to the edge of the subway platform for my own comfort. As a general rule, I play it safe. Gambling holds no appeal; in the words of Carrie Bradshaw: “I like my money where I can see it: hanging in my closet.” As dark as this sounds, I occasionally find myself plotting possible paths of egress in case a shooter appears in my Church, on the Subway, etc. I am hard-wired to plan for contingencies. I never leave anything to the last minute (anticipator for life) if it can be avoided — even as a schoolgirl, I completed my book reports days before they came due. I check the weather on my phone every morning. I fret disproportionately if I am running close to an expired parking meter or if Google Maps predicts an arrival time even a few minutes over an appointment start date. I prefer not to leave anything to chance, and will needle people when all the boxes on a form or checklist are not appropriately ticked, even if I realize I am irritating because of it, and even if I realize it does not really matter. I will ask the obvious question even if I imply obtuseness. I wear sunscreen daily and never miss a routine checkup for skincare, dentistry, OBGYN. I even schedule annual wellness checks with my general practitioner when I am in good health. I am a rule follower to a fault. I take almost personal offense when I see a fellow dog-owner has not picked up after his dog: he is breaking a serious social contract and making all of us dog-owners look bad! I never cut in line. Mr. Magpie tells me sometimes I make up rules that haven’t been set and imagine being punished for them — and he is correct.

I color in the lines.

And yet.

I am a risk-taker. My professional career stands as a testament to that truth. There were so many rich insights and provocations in response to my post last week about pursuing two degrees in English and my mixed feelings on whether I would recommend the same path to anyone, and one of those comments left me deep in thought about whether my academic career in some way pushed me to be more willing to take risks than I might have had I chosen a degree with a more straight-forward professional application. Like many liberal arts majors, I had to bend the degree to fit various job opportunities, or to search for a position that was sufficiently generalist in its entry-level responsibilities that nearly anyone might qualify, and then create a tenuous argument as to why I was in fact perfectly qualified for it. This meant I remained, out of necessity, open to possibility. I worked for a government consultancy performing the most menial and tedious of tasks (calling government offices asking for information about upcoming contract opportunities), as a nanny, for an academic press, then for two ambitious start-up non-profits. There was also a time where I had carved out a small editing practice, and I had a few professors, a “recovering lawyer” (as my Dad calls himself), and an academic journal as customers — was that truly in this life? There was a period of about six years where I worked dutifully towards a long-term career in non-profit management, and I felt my identity beginning to conform with its shape. “Jen Shoop, tenured non-profit leader” had its own sturdy appeal. I even got to the point where younger members of the non-profit community called upon me for advice. I was invited to speak on panels. I attended lunches and meetings and exchanged business cards with people far more important and seasoned than I. Then I upended that plot line by starting a new business with my husband in an industry it turns out we did not know well enough. In the process, I re-cast myself as an entrepreneur.

My two degrees in English and my many years of writing compel me to draw a legible line between these experiences. There is the writing angle: I have never — not once! — been in a role that did not call heavily upon my writing and editing skills. There is the education angle: nearly all of my undertakings have in some way hinged upon an interest in promoting learning. There is the design angle: in my last four jobs, I have found myself engaged deeply in questions of product ideation and management.

But the truth is that where I might draw a line, confident in its linear arc, there was actually a wild swinging of arms as I leapt — sometimes tumbled, sometimes flung myself — into the unknown. I cannot reconcile my call to entrepreneurship with my play-it-safe nature. They remain incompatible, the unlikeliest and least amiable of bed-fellows. How is it that I am near-allergic to the idea of not purchasing a return ticket back from D.C. on one of these house-hunting excursions in the event that we would like to visit one more property (but what if all of the later-evening trains are full?) and yet I took an absurd gamble to work for a twenty-two-year-old college graduate trying to improve the financial literacy of low-income youth when I had, at the time, been promoted to acting Executive Director of a well-funded non-profit? And how can it be that I will plan what my daughter will wear to school the following morning when I am drifting off to sleep at night, occasionally discarding options because they have not yet been ironed, knowing that just a few years ago, I stepped away from a secure-seeming career in the non-profit world to start something entirely new and unknown?

I mystify myself sometimes. I might be the world’s most cautious tearaway, the most dutiful of daredevils.

How about you? When you zoom out on your life decisions, do you feel you’ve always played it safe or have you taken big risks?

Post-Scripts.

+The dotted lines between work and self.

+On being a rule follower.

+On learning which rules matter.

+I always enjoy these posts because I find I get to know you all so well in the responses. But you can also introduce yourself here or here.

+More on my backstory here.

Shopping Break.

+People love this brand of underwear. Going to snag some for myself! (I usually swear by Natori and Hanky Panky, but always open to testing the new new.)

+Swoon. New contender for my birthday dress. I turn 37 in June!

+Another great, well-priced chair for your backyard/patio. (More picks here.)

+A rattan umbrella stand! Mr. Magpie and I have bought this exact umbrella stand now fewer than THREE TIMES because Tilly broke the first two while chasing toys in our old apartment. It wasn’t ideally situated…

+OMG these adorable denim shorts for a little love! She can twin with you!

+This Cult Gaia is perfection.

+A great knit dress in that aqua blue!

+Never thought I could get excited about tissue box covers, but here we are. How good is this pattern or this one?

+These personalized hats for littles — I love the gingham!

+Just ordered micro these $23 swim trunks in the red and white stripe. If I like the fit, I will order the navy gingham, too! Note the 3,400+ five star reviews (!). I have purchased him the Minnow rash guard in the past, but am contemplating this inexpensive style in white or navy for this summer.

+All my favorite beauty buys.

+It’s Native shoes season.

+This $40 gingham dress is right up my alley as a cute everyday outfit option. Imagine with my new sunhat and these on-trend woven sandals.

+Another great pendant lamp to add to this roundup.

+Great transitional sweater — pair with white jeans or even shorts!

+Comfortable joggers by Splendid marked down to $31 in a cute blue and white stripe.

+Such fun little wine glasses.

+This dress is back in stock!

+Kitchen organization finds.