Finding my way out of work ambivalence

I have a confession. In the past two months, I’ve thrown my hat into the ring for two jobs. Both were executive-level positions, and let me tell you, while I have an excellent resumé and can write a damn good cover letter, I applied for both jobs in the most half-assed way possible. At my age, and with my experience, the only way to get seriously considered for a job is to go in with a referral—a recruiter who knows you really well, or a contact who is very close to the people hiring inside that organization. And I did neither of those things: I applied through the job portal, despite knowing only a handful of people who have gotten jobs that way. For desirable jobs that both offer high salaries and interesting work possibilities, there are literally hundreds of applicants trying to squeeze through that portal. And even though the hiring staff promise that they’ve reviewed each and every application carefully—perhaps they have—it’s just like college applications. They all start to sound the same, after a while.

Unsurprisingly, I did not advance to the next round for either search. And while I felt the inevitable sting of rejection, I also felt a sense of relief. I am very fortunate in that I currently do not have to work full-time, in part due to past efforts and current income streams, and in part due to my perpetually stressed-out husband, who has always worked full-time (I would go back to work full-time if I thought he would take a sabbatical, but he’s so not the type to do that.) So I’m currently in some stage of my career where I am letting the universe tell me what I am going to do next, or if I’m even going to keep on working at all.

Why am I being so passive about this next stage of my career? A lot of this has to do with a current state of ambivalence about what work IS these days. In 2019—which feels like eons ago—I wrote here about how people seeking jobs often hear this advice: figure out what you want to do. And I argued that actually lots of people know what they want out of a job, but the problem is that they often can’t find a job that matches their requirements (let alone their skills).

Since that time, we’ve gone through a global pandemic which had a profoundly disruptive effect on work in the short term, TBD on whether those effects will last over the long term. It feels like every day, I read a new article about battles between CEOs who want people back in the office, versus workers who long for the flexibility of remote working. In addition, I don’t think it’s hyperbole to say that during that same period we were going through the crisis of the pandemic, our country also experienced a national reckoning on racial justice and equity. This reckoning had been brewing for a very long time, but the murder of George Floyd and a rash of hyper-partisan opinions from a bought-and-paid for Supreme Court majority, put a much finer point on much more we need to do, as a country, on racism, equal opportunity, and individual autonomy. Finally, thank goodness, organized labor’s been having a moment. I am sorry that we’ve been brought to this moment because of corporate greed (as if “living wages” is such an unreasonable ask), but it’s good to see some momentum in that arena.

It’s been a LOT, in other words. During this period of great turbulence and uncertainty, I had the good fortune of frequently enjoying my work. I spent the time mainly writing about people who were doing interesting, important work. I functioned as a coach, a storyteller, a facilitator, a here’s-what-I-think-the-main-points-are type of person. I was not a leader with any actual authority over strategy or budget.

I loved being a colleague and a supporting player. And I had lovely colleagues and clients to work with to help assuage the loneliness and isolation of being a consultant and a writer. But now, in early 2024, I’m pretty sure that this work chapter might be either ending or changing, due to a whole host of factors, like the legal requirements for companies on how they deal with contractors, or my sense of burnout after writing so many pieces last year where I started to feel as if the amount I worked versus the amount I got paid felt off-balance.  

These factors, and others, have brought me to a career crossroads. I’ve stood at these crossroads many times in my life, but each time feels different, because of where I am with my age, experience, and economic security.

Here are the questions that I’ve been chewing over lately:

• Have full-time jobs changed to be more flexible? When I left full-time work, in 2017, I had a string of jobs under my belt, most of which required me to be in the office, full-time. Except for one organization, remote work was really not a thing. Part-time work was also not a mainstream thing, unless you were a parent returning from maternity leave and had very small kids and could negotiate working 100% of the time at 80% of your salary with the freedom to not join calls or answer emails on a Friday. During those days, I longed for greater flexibility in my work—so I didn’t have to endure a punishing commute every day, so I could exercise at an hour other than 4 am in the morning, so I could cook meals for my family and attend parent-teacher conferences and school functions without guilt. The pandemic forced a bigger shift to remote workers but there were many essential workers who still had to show up in person, and many remote workers still had to work round-the-clock, with very little support for child care or personal lives. I see some organizations that promise four-day workweeks, or meeting-free days, but those instances are still too rare for me to get a sense of whether flexibility in the workplace has truly changed.
• Do I need to earn a certain level of income and if so, how much? This is a truly complicated question for me to grapple with. My husband and I live in a very expensive area. Our kids are just barely launched out of the nest, and my husband and I are the sort of parents who will want to help them with expenses if we can, as our parents did for us. My parents are getting older and helping them with their transitions and traveling to see them has involved some expense. And while we theoretically could live on my husband’s income alone, this has always been a fraught option for me. (My mother’s advice on this front: “Never depend on your partner for money. Not because you anticipate breaking up, more because you want to be able to depend on him for everything else except money.”)
• What is the ratio of fulfillment versus bullshit that I can tolerate in a job? At this phase in my career, I have a pretty clear sense of what I’m good at and what I’m not good at. So most executive communications jobs that come up, the job descriptions outline things I can do, and do well. Put another way: even in jobs with toxic, dysfunctional working environments (and shame on me for taking those jobs, when I’ve gotten a clear whiff of what lies ahead in the interviews), I’ve managed to have a positive and enduring impact. I’ve always gotten stuff done. But with this confidence in my own ability comes an insecurity about how much bullshit I can tolerate. Meaning, there’s one part of my brain that is saying, “I will do anything for you, and do it well, as long as there are reasonably nice and funny people to work with, and the mission and purpose of your organization rings my bell.” But then there’s another part of me that’s fearful—yes, actually fearful—of running into a CEO that’s super-ego-charged, or of serving on an executive team in constant conflict with one other, or of finding out that an organization that says they’re committed to diversity, equity, and inclusion is actually not.
• A related question: can I go back to handling the stress associated with an executive position? I don’t really believe that an executive position exists that doesn’t come with considerable stress. When you’re in it, you do what you need to do to survive, even if you feel like you can’t draw a deep breath, even if you tell your colleagues and employees to practice self-care when you yourself are not doing it at all. I have known a very few executives who were preternaturally serene—nothing ever seemed to rattle them. One was a practicing Buddhist, one told me that she was born that way, and another told me that she was a positive genius at compartmentalization. For others like me, who feel things deeply and tend to over-express themselves, being an executive is not always a comfortable fit. It’s great for communications and narrative work and storytelling, not so much for all of the budget/HR/administrative issues that an executive has to deal with (my eyelids still twitch when I hear the word “procurement” or “new benefits provider”).

These are all questions that are churning in my mind, in 2024. But after my two job rejections, and a great deal of reflecting, I may be making some progress in getting past this career crossroads. (I often tell much younger people I advise and mentor that career crossroads are the absolute worst, when it comes to anxiety and uncertainty. But they’re also inevitable, and then the road one decides to take always yields rewards and surprises and lessons.)  Here are the tiny, tiny things that are making me feel as if I’m inching towards a direction:

• One, I am appreciating the value of the work I am still doing. I said I was burned out on writing long case studies and that’s still true, although I have a couple more to produce this year. But at the same time, every time I finish a draft and I manage to capture the essence of a project or an endeavor that people truly, deeply care about, I feel a sense of immense satisfaction. I am humbled that people entrusted me to capture their stories and I am also moved by their appreciation when I do so, successfully, in a way that makes them feel heard and seen and valued.
• Two, I appreciate the value of the things I do that have nothing to do with monetary compensation or work. I am a mentor and a coach for my kids, my husband, my family members, and good friends. I write these pieces, in this space, and have gotten appreciative reactions and gratitude from many people I barely know IRL. I have gotten quite a few offers to monetize this blog, and so far, I’ve resisted—while I support many different types of content creators, ranging from cookbook authors to OG mommy bloggers, now on Substack—no monetization model feels right for me, just yet. I just want to share what I’m thinking about, with the hopes that others might find it useful. And my goodness, I LOVE doing a podcast with my son on movies and entertainment. It is almost shocking to us when we find out that we have actual listeners, because we enjoy doing it so, so much, it feels like that’s the reward, and listener appreciation is the bonus.

And finally: it’s a good thing, to be in your mid-fifties and to still be able to be on a journey of self-discovery. What I’m good at, in work, and what I want to do, are related but distinct categories. There is almost nothing in the communications/narrative space that I can’t do—campaigns, messaging, media outreach, branding, content creation, organizational communications, government/policy relations, marketing/development, executive communications, speechwriting, website builds—these are all things I have led or done myself. But what do I actually want to do, in these later stages of my career? What do I think I’m best at, based on the feedback I’ve gotten over the many years of my career? It comes down to strategy, advice, and writing. Had I been gifted with more foresight about my current state, I might have hung onto a foundation job a little longer, so I could have been gifted what one friend refers to, a bit derisively, as a “comfy pouf upon which to perch and produce nothing.” (These jobs usually come with the title of Senior Advisor or Special Advisor.) However, I DO like to produce things and am completely unable to occupy a special perch unless I can also provide tangible value, like writing things or designing and facilitating meetings, or training staff who want help with writing, messaging, or other aspects of communications.

I will keep on searching for work, or a job, that enables me do these things. If I do find those attributes in a job, I will — I promise — put up with a LOT of bullshit. And if I don’t find them, well, no more flinging my resume at portals for jobs I don’t really want. (It is looking very likely that I will only get rejected, anyway, and I may have already sealed my fate through the writing I do here.) After all, I am lucky: I’ve already had an absolutely terrific career, one that has afforded me the opportunity to work with some truly amazing people. Maybe now is about holding those types of spaces open and helping others to do the same.