For years I hadn’t been particularly happy in my work as a web content strategist. But as a busy mom who’d never been great at changing jobs, I stuck with it. Then, enter COVID-19 — with many stressful hours working at home alongside my virtual-schooling 9-year-old — and something had to give. What followed began with me facing just how terrified and ill-equipped I felt in the face of defining my career. But it ended almost miraculously as a case study in how life can bloom before your eyes if you let go of the perfectionism that you thought you needed to be successful or happy. I changed my career my way by taking baby steps and playing to my strengths. Here’s how I re-defined my career and, for the first time in my life, ended up satisfied with my work.
When my son was born 10 years ago, I was perfectly content to give up my full-time work as a lawyer. I ran through my savings while working part-time in a blissful period of momming. But by the time my son was 3, the money had run out. I feared the stress, long hours, and daily multi-hour commute that would likely come from returning to full-time legal work. So, when an acquaintance from my co-working space offered me a remote job in content writing and editing for his legal marketing agency with a flexible schedule, I said, “Sure.”
After several years, it was increasingly apparent that the flexibility couldn’t make up for the sheer number of hours I felt I needed to work to do my job well, and I was not particularly inspired by the for-profit marketing world. The company also wasn’t a great fit for me culture-wise; I’d quickly ascended to management, but my style differed significantly from that of the high-energy, constantly-pivoting, entrepreneurial men in charge. I tried to create change from the inside, but, ultimately, I really just needed to move on. Yet, the shift away from legal practice made me feel like I’d cut my career off at the knees, and I didn’t know how to stand again.
I was overwhelmed to the point of disgust by the standard advice about how to change jobs or start a new career path. “Volunteer in a role or organization where you’d like to work!” (With a full-time job and a child? Right.) “Become active in professional organizations!” (See previous comment. Also: how to choose which ones if I don’t know exactly what I want to do?) “Read the What Color is Your Parachute-type book of the moment and then re-tool and re-brand yourself for the career you want to inhabit!” (Already read them. Also, despite what I told my marketing clients, I frankly find it gross to think of myself as a product.)
Leave it to me to need a global pandemic to get me off my ass. When Covid hit, my difficult job became unbearable and I honestly feared — as so many of us did — that the stress would break me. But my family depends on my income and I knew I was immensely lucky to still have full-time work. Moreover, it was clear that it would be logistically (and emotionally!) impossible for me to engage in an active job hunt on top of everything else.
What I really needed was time off to regroup. So, my husband and I counted up our recently re-built savings and made a deal: I could quit my job if I hired a job coach to help keep me accountable and moving forward. And, as my husband consistently reminded me when I got anxious during about three months without a paycheck (and at least three more with about half a paycheck), we considered this a worthy investment — the same way we would have if I needed time and tuition to retrain for a more promising new career, for example. During this period of refocusing and redefining my career with my coach, I had some revelations.
My first big “Aha” moment came because I thought I was hiring a coach to whip me into shape — yet she didn’t.
I assumed that my career woes lay in a sort of childish inability to put on my Big Girl pants, identify my singular passion, and pursue it relentlessly with networking and resume-building (and probably some horribly uncomfortable tailored suit).
I admitted to my coach early in our Zoom relationship that traditional job-searching and career-defining tasks filled me with dread. I asked if we could make an agreement that every time there was something she felt I should do, we’d discuss it as something I could do, not something I had to do, to avoid sending me into an anxious tailspin. She shocked me by responding, “What if you don’t have to do anything? What if, instead, we figure out what your way of job-searching looks like?”
I was skeptical. When left to my own devices, I had a well-established tendency to fuck things up. Case in point: my current predicament of being jobless and having no idea what to do after sticking with a job I didn’t love for over five years.
But somehow she instead convinced me that my predicament just might, instead, be a result of my very assumption that I was doing everything wrong. I began to consider that, if we look for jobs (or suits) from an ill-fitting, have-to perspective, we easily end up with ill-fitting, have-to jobs (and suits). Whereas, if we lean into our strengths with faith that they are strengths, we can find circumstances that fit those strengths.
Next, my coach and I had a long discussion about my values. By “values,” she didn’t mean a concocted list of things you think you should stand for. Rather, these “values” are more akin to what I would call “needs” or “strong wants.” I sheepishly worked with her to list out — with as little judgment as possible — the things I honestly felt I needed. “To feel like I’m contributing something positive to the world.” Check. “To use my intellect.” Check. “To feel respected and included.” Yep, that’s an important value. “To spend time with my son.” That’s a huge one. “To binge on Netflix?” Yep. A need for mindless downtime — a totally legit value.
We went on like this, developing a big list of values, some of which were more embarrassing than others. And she explained that it would be natural for my values to change over time, ebbing and flowing, adding and subtracting. Most importantly, she explained that we all constantly balance and re-balance our values. Some values are more significant or more easily met at different times, and we need to humbly accept that no one perfectly fulfills every single value at all times. The key is finding a balance we can accept at any given time.
Applied to jobs — and arguably applied to almost anything the kicker is therefore that, at any given moment, there is no perfect choice. There is simply an informed choice for you. It’s hard to go into a job you’re not 100% sure about if it feels like a failure to find the perfect job. It’s much easier to get excited about a job that you’ve calculated, on balance, will honor more of your values, or values that feel particularly pressing.
Here’s how I job-searched my way, doing things that felt relatively safe and that felt like me:
In other words, compared to the epic job hunt I had originally imagined (and feared), I did what looks like practically nothing. And yet it was something. It was a series of baby steps that allowed me to start where I was, instead of taking a huge leap I wasn’t ready for. Just as importantly, I was exercising undervalued traits that may actually be strengths: rest, self-care, fun, seeking connection, and making sustainable progress instead of overreaching. Honestly, it was terrifying. But it was also exhilarating. It was like stepping into a life I might actually want, instead of grudgingly charting a course for more stress.
In the end, I was offered two jobs — neither of which I had even applied for. Remember those two social occasions with friends? I consciously chose to meet up with these particular friends because of their Covid-friendly outdoor meeting capabilities. One friend is the mom of my dog’s best buddy and has a huge fenced yard. The other has a fire pit for outside gatherings and lives close enough that I can walk home if I drink too much wine, which I did. I realized in retrospect that each of these friends is also a strong career-woman and breadwinner for her family. With each of them, I was my vulnerable self, discussing my career fears as well as my strengths. In other words, without even realizing it, I was networking. As me. No suit required. And each of them offered me remote, freelance work with incredibly inclusive all-woman teams.
Neither job is perfect. One is editing work, which draws on my marketing days, and squarely involves social justice, but could never pay enough to be my only job. The other is intellectually challenging legal work that pays incredibly well but requires a fairly bumpy, mostly unpaid total retraining and has an unpredictable workflow. In a good month, I earn more than I did before in about half the hours I used to work. In a “bad” month I binge on Netflix, count my blessings, and spend even more time with my son — including doing things we never had time for before, like returning the pandemic’s worth of bottles from our garage and using the deposit money to buy wishlist items for local community groups.
In other words: At the moment, my career is perfect. Certainly my values will shift again. But when they do, I’ll be slightly more ready to shift with them — incrementally and in my own way.
Caty Lillie* is an attorney, editor, and writer with a professional focus on health law and research. Her first piece of published fiction juxtaposed the zombie apocalypse with an MRI procedure. A former (and sometimes still) musician, she lives with her musician/writer/media guru husband, chess-genius son, octogenarian mother, a blind and deaf Cockapoo, and a terrier/mutt who climbs trees. Caty’s sandwich generation role as a parent trying to work full time from home sometimes calls on her to be Superwoman. She endeavors regularly to tell that call to F off.
* “Caty Lillie” is a nickname derived from the author’s married name. She practices law under her full (maiden) name.
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