Daily Excerpt: The Book That (Almost) Got Me Fired (James) - Candidacy

 


The Book That (Almost) Got Me Fired by Kelly James is now available in audiobook!

#3 ON AMAZON'S LIST OF HOT NEW RELEASES FOR NEARLY A MONTH

Book description:

You're 52. Divorced. Single mom to a teenaged son and a tween daughter. Happily self-employed but worried about the cost of health insurance, the inevitable impact of perimenopause on your body, and whether you should keep dating a sexy plumber who's sweet and funny but lives an hour away and doesn't seem that into you.

So, after 22 years of fulltime freelancing, you take a day job as a tiny, creaky cog in the corporate American machine where you're decades older than most of your coworkers - and you write about it. The Book That (Almost) Got Me Fired: A Year in Corporate America is an entertaining, midlife memoir that shares what (and what not) to do when you make that corporate leap.



Keywords:
Midlife career change; Corporate culture transition; Workplace memoir; Freelance to corporate; Women in the workplace; Single mom career; Over 50 career switch; Workplace humor; Corporate survival guide; Midlife reinvention; Career transition memoir; Age diversity workplace; Work-life balance; Second career journey; Corporate America satire; Female workplace memoir; Workplace resilience; Career pivot after 50; Self-employment to corporate; Midlife professional growth; Business humor; Millennial work environment


Candidacy  

 

 “So, why would you apply for this position?” Frank Becker, manager of the content department at Digital Edge, leaned back in his chair, his arms folded across his chest.

            It was a reasonable question. After all, I’d been freelancing full-time for nearly 22 years. Now I was interviewing for a job. A full-time job. A (gasp) real job.

            I’d applied for the content specialist position on a whim. Digital Edge was three miles from my home, and the brief job description sounded like work I could do. I submitted a resume and a cover letter the day before Thanksgiving and had already forgotten about it when I received an email the Monday after the holiday to schedule an interview.

            I hadn’t expected a reply, much less an interview, so I did a little quick research before I drove over to meet with Frank. Per its website, Digital Edge specialized in internet marketing, including SEO and PPC campaigns. I’d written SEO (Search Engine Optimization) content for freelance clients in the past but had no clue what PPC was until I Googled it a half-hour before the interview. PPC stood for Pay Per Click, as in online advertising.

“I’m going to be completely transparent,” I told Frank. He was about my age, stocky, with a closely cropped haircut. He wore a pullover sweater and jeans while I was sporting one of my favorite grownup outfits—a black, white, and blue patterned skirt with a black scoop-necked blouse.

“I got divorced two-and-a-half years ago. The first year, you’re just kind of scrambling, trying to manage all the changes, make sure your kids are okay, keep it together, and try not to cry at random moments,” I said. “The second year is more like, ‘okay, this is what life looks like now,’ things are settling down, you’re not completely freaked out anymore, you’ve got some mental space to handle stuff. The third year is like, ‘okay, what does the rest of my life look like? What do I do now?”

Frank nodded, probably wondering how much more of my personal life I was going to offer up during the rest of our interview. (Spoiler alert: pretty much all of it.)

“Well, that’s where I’m at now. And let me just say—health insurance is a driver for me. The cost is killing me,” I said, ignoring the irony. “The other thing is, I love what I do as a ghostwriter. I have a really close relationship with a client for six, nine, twelve months while I’m writing the person’s book. Then, the book is done, and, bam! I’m on to the next client and the next project. That can get old.

“I’m an extrovert in an introvert’s job,” I explained to Frank. I told him that every morning after dropping my daughter off at school, I drove to the Peet’s coffeehouse about a mile from my house. I ordered a large skim latte, minus a shot, and sat at the end of the long cedar table in the corner, eavesdropping on conversations and taking breaks to chat with my compatriots who followed a similar routine. There were Chuck and Bill, both of whom were in insurance. Sy, a financial advisor. My friend Mary, a retired social worker. Jordan, a 20-something who worked with special needs kids and was writing a young adult novel between appointments. Roger, one of the founders of Spenga. My neighbor Kevin, a retired broker who was learning Spanish for fun. I spent the mornings at Peet’s, banging out articles and books, drove home for lunch, and spent the rest of the day with my feet propped up, working from a corner of the couch in my living room, which I called Command Central. Then, my kids came home from school, and I parented the rest of the day.

Frank asked about some of my freelance experience, and as we talked, I wondered if I should admit that I’d applied for the job on a whim. While I was finishing my best year money-wise in more than a decade, I was feeling more and more anxious about continuing to freelance. Most of my income stemmed from writing books and book proposals for clients, but the work could be erratic. Sometimes, projects got tied up for weeks at a time, languishing on an agent’s or editor’s desk.

I liked to work, and I liked to work hard. I didn’t mind banging out 10-hour days or working nights and weekends if necessary to meet a client’s deadline. What I did mind was having to deal with dead days where I didn’t have work. An occasional day with little to do let me reboot. Consecutive days left me feeling uneasy, underutilized, and scared. As a ghostwriter, I was always looking for my next project, and those projects weren’t always coming at the speed I needed to maintain both consistent cash flow and work.

A year before, in a fit of money-driven anxiety, I’d applied to a slew of full-time jobs, with the single-minded intent of securing health insurance. When I was married, health insurance wasn’t on my financial radar. When I got divorced, my former husband, Erik, and I agreed to keep the kids on his health insurance, but I saw the monthly premium for mine climb to $600 a month—for a $5,000 deductible policy which didn’t even cover the cost of the selective serotonin reuptake inhibitor I took for anxiety, which was both effective and expensive at $330/month. Add in the cost of my shrink, Molly, whom I saw every month or so, and I was spending nearly $10,000 a year on my health care.          

And I was healthy, except for my lifelong companion of anxiety which flared up now and then, chronic insomnia, and ongoing issues with my left knee and right hip, both of which were no doubt aggravated by my insistence on continuing to run nearly every morning in an ongoing attempt to manage my anxiety. While my 52-year-old body was starting to complain, a hard session on the treadmill was the most effective way of burning off the swirling mist of existential angst I woke to nearly every morning.

None of the jobs I’d applied for had panned out, so I’d recommitted to marketing myself and rebuilding (yet again) my freelance business. I’d been doing this for more than 20 years, and in the past, I’d always been able to shake fruit (or in this case, clients and work) loose from the trees and wind up with enough work and enough money.

While I got a little maintenance and child support from my former husband, Erik, the last couple of years I’d been making barely enough to support myself, my 13-year-old son and nearly-9-year-old daughter. Earlier that year I’d had several promising book projects fall through, and while I was working on a couple of proposals for ghosting clients, there was no guarantee that they would sell. No sale meant no book, which meant no work, no money, and even more anxiety.

I didn’t share all of that with Frank, but I was candid about the fact that I had two school-aged kids. That I was 52. That after a less-than-satisfying career as a lawyer, I had been self-employed for more than 20 years. “Honestly, the idea of taking a full-time job is kind of scary. I don’t know that I can give up the freedom and flexibility I have. Also,” I added, “I’m pretty sure I’ve covered everything you can’t legally ask me in this interview.” I laughed.

Frank nodded and steered the conversation away from my random inappropriate disclosures and explained what the position would entail. The content strategist job was a newly created position, the first of its kind.

As the content strategist, I would be the liaison between the SEO and content departments. Digital Edge worked with mostly small and medium-sized businesses doing internet marketing campaigns designed to increase the number of “qualified leads” (potential customers) that websites brought in. The SEO team did research to determine what search terms, or keywords, a client’s page should contain. Keywords were the phrases that potential customers used when looking for that type of business.

“I need a businessperson who thinks like a writer,” he said. “Or a writer who thinks like a businessperson.”

That was me. I’d built my career on the idea that I was a businessperson first and writer second and had developed a niche as a successful freelancer, even writing books about how others could do the same. “I can do that,” I said aloud. “I do do that.” I looked at him. “It does sound interesting. It’s more a conceptualizing/big picture type of job than a writing job. Correct?”

He nodded. “But there would likely be some writing involved.”

“I’d like that. I have done a fair amount of writing for the web,” I said, though most of my background was in the dying medium of print. I looked at the outline samples. “How many of these would I be expected to produce in a day?”

He held up his hands. “I can’t answer that. Because this is a new position, we’re not sure yet what it will look like. We’ve had people in Atlanta—we have another office there—creating outlines but we need someone here who can take them over as we migrate clients to our Digital Plus model. The content strategist will be responsible for those clients.”

The job sounded intriguing. I’d already confirmed that the company offered health insurance to its full-time employees. And the chair I was sitting in was quite comfortable. “Wow! I have to say, it sounds like a great fit for me! Give me $80,000, and I’m yours!” So much for any kind of thoughtful salary negotiation! The number fell out of my mouth without thinking about it.

Frank uncrossed his arms and leaned forward in his chair. “This position is considered entry-level,” he warned, looking down at his notes. “The salary associated with the position is $35,000.”

$35,000? A year? I was at the stage of my ghostwriting career where I made around $40,000 for a book, typically writing a book a year along with other work like book proposals and articles that got my income up to the $60,000 or $70,000 range, hopefully even more. Now I was single and didn’t have the luxury of a second (not to mention much larger) paycheck, I needed to make that much.

“Oh.” I sat back. “I can’t do that.”

Frank didn’t argue. “There is another position here that we’re hiring for,” said Frank, passing me another job description. “It’s a position for editor.” That job paid $45,000, which was still low.

I glanced at it and shook my head. “Editing isn’t my strong suit,” I said. “I’d get bored doing nothing but editing all day.” I liked to research, to write, to create frameworks for articles and books and then fill them in. While I had edited a couple of books for clients, I’d only done developmental or “big picture” editing, not line editing where you checked grammar, spelling and punctuation, following a style guide like The Chicago Manual of Style or The Associated Press Stylebook. I knew they had differences but had never bothered to figure out what they were. When an editor said something like, “We use AP,” I’d think, “Cool!” and leave it at that, assuming that it was the editor’s job to make sure that the stylebook was being followed.

Frank seemed to sense that any interest I had in the job was evaporating. “I think you’d be a great fit for this position,” said Frank. “I’m willing to go to the partners here to see if I can authorize a higher salary, if you’re interested.”

 “I appreciate that,” I said. “But honestly, I’ve been freelancing for so long I don’t know if I can sit in an office all day.” Once again, I spoke without considering the impact my words might have.

“Why not give it a try? Give it six months. It doesn’t work out, you go back to freelancing. Hell, give it two months. I think you could do a lot for the company in this role. You could take the position and run with it.”

Gosh! When was the last time a client had gunned for me like that? I was always the one chasing down clients and nailing down work.

“Let me give you a tour of the office,” Frank said. We’d been sitting in the CEO’s office—the partners had their own offices while the rest of the staff worked in one large room, sitting at mini cubicle farms of six desks each. The room was large, with high ceilings and glass windows on all sides. It was well-lit and relatively quiet, considering there were about 50 people throughout the room. Most were in their 20s, with a few more seasoned employees scattered throughout. The majority were men, and at least half wore headphones, which explained the lack of conversation. Nearly everyone was dressed in sweatshirts and jeans. I knew the office had a casual dress code, but this had the feel of a college library more than a workplace.

 Most of the employees’ eyes were glued to their giant screens, but several glanced up and smiled at me as I walked by with Frank. (“They thought it was bring-your-grandma-to-work day,” said my neighbor Brian later.) The vibe seemed … good. Comfortable. No one appeared to be actively miserable, at least as far as I could see.

I met Roger, the other man I’d be working with closely. Like Frank, he was a former sports reporter and editor, a few years older than I, and had an easygoing, rumpled look about him. I saw several younger guys in their late 20s or early 30s pacing near the back of the building. They were good-looking, fit guys with cordless headsets, and I could tell from the brief snatches of conversation that they were in sales.

Frank showed me the “nook,” a little kitchen stocked with coffee, bagels, and bowl full of carb-heavy packaged snacks, the meeting rooms, and the cafeteria. Then. he asked if I had any other questions and asked me to get back in touch with him if I did.

I couldn’t take the job at $35,000. Before- and after-school childcare for Haley would push my salary into the minimum wage zone. But what if the company offered me more? A lot more? Was it willing to give it a try, as Frank had suggested?  Why not? It could be an adventure.

“I think I want this job,” I said as I walked down the stairs of the building. By the time I climbed into “Cherry Cherry,” the bright red 2018 HRV I was leasing. a few seconds later, the feeling had crystalized.

“Holy shit,” I said aloud. “I do want this job.”

I met my friend, Chris, a fellow freelancer who worked as a marketing consultant, for lunch immediately after my interview. “I think I’m going to take it,” I said. “What do you think?”

“You can’t not take it! It’s health insurance. It’s three miles from your house. And for some reason, they actually want you!” He took a giant bite of his pulled pork sandwich.

“But I can’t do it for $35,000, so I have to see what the offer is,” I countered. “The health insurance is great. But I’m going to have to pay for childcare again, and I haven’t had to do that since Haley started school. I think I’m worth at least $80,000, but the company seems to be pretty cheap in terms of salary, so I think my number is going to be $60,000. Maybe $50,000.” After all, health insurance would save me at least $10,000 and that was after-tax money.  

Chris nodded. “That sounds fair.”

“You know, the fact that they’re even willing to take a chance on someone who’s been self-employed for most of her career is significant,” I said. “Besides, if it’s horrible, I can always quit.”

“Oh, that’s a great attitude,” said Chris. “If you wind up taking it, take it with the intention of succeeding in it. Give yourself six months—or a year—before you decide whether it’s working for you.” He took another bite of his sandwich. “You should commit to it for a year,” he said, his mouth full.  

The next morning, I listed the potential pros and cons of the job. I’d done this for years whenever I felt my enthusiasm for freelancing flagging. Enumerating the pros (I’m in charge of my own career; I can make my own schedule; I like the work I do; I’m making $40,000/book) had always managed to let me downplay the cons (super-expensive yet crappy health insurance; little security; the constant need to market myself; the feast-or-famine nature of the work).

 

Pros of Taking the Job

 

1.     I’d have health insurance. For a lot less than what I was paying now. It meant I could finally get that colonoscopy I’d had my eye on! At nearly 53, I knew I couldn’t put it off forever.

2.     It was convenient. The office was 3.2 miles from my house, per my Maps app. It would take maybe 15 minutes to get there—assuming I didn’t encounter a train on the way to work. (My town is bisected by train tracks, and you can easily get hung up for 10 or 15 minutes if a couple of freight trains roll through.)

3.     The company wanted me. Visions of Sally Field—“You like me! You really like me!”—notwithstanding, it was flattering to be wanted. Frank had said he knew I could do the job. He’d said he’d go to the partners to get more money for me. He wanted me! And I loved to be wanted.

4.     I’d know how much money I would make. Twice a month, every month, money would be deposited into my bank account. Every month. I would no longer worry (okay, obsess) over whether, or when, I’d be paid.

5.     I could continue to freelance. This was key. I had a couple of clients that I wanted to retain, including Nancy, an Instagram influencer who wrote about how to eat to “heal and seal” your gut if you had digestive issues like irritable bowel syndrome. I’d worked on her proposal for the last seven months, rewriting it three times, and her agent was finally about to shop it around. I wanted to write the book itself if it sold.

 

Cons of Taking the Job

 

1.     I’d have to actually, you know, show up to work. Every day. With actual clothes on. My kids, neighbors, and most people who know me are aware of my penchant for outfits built around overalls and Birkenstocks, a fact that caused my 9-year-old-fashionista-in-the-making daughter some anguish. I knew that more would be expected, even required, with even a “casual” dress code.

2.     I’d be sitting. All day. At a desk. As a writer, I sat a lot, but I broke up that time. I worked at Peet’s in the morning, went home for lunch, and broke up my afternoon with walks around the block and trips to the basement to throw in a load of wash or quick trips to the grocery store. Almost every Friday, I took a long, lazy lunch and often took the rest of the afternoon off.

3.     I’d be saying good-bye to my freedom. See number two. Freelancing = freedom. The words even start with the same syllable! I would have to answer to a boss, account for my time, deal with coworkers, meetings, office politics, and all of the other corporate headaches that the regularly employed simply accepted as the norm. The thought made me a bit stabby.

4.     The what ifs. What if I simply couldn’t do the work? What if some of the people I worked with didn’t like me? What if none of them liked me? What if they nicknamed me Granny, made comments about needing a walker, or otherwise let me know that I was … old? After all, 52 seemed ancient when I was in my 20s. (Forget “50 is the new 30.” We all know this is bullshit we Gen Xers try to sell to each other on the regular, but the fact is that at 50, you’re looking at the second half of your life, not the first.) What if they all went out for drinks and didn’t invite me? What if they did invite me, and I could think of nothing to say? Who would I talk to in the lunchroom? I’d forgotten most of what I once knew about working in an office environment, and I knew next to nothing about Millennials other than that they were the most-maligned generation.

5.     I was giving up, wasn’t I? I’d been a fairly successful freelancer for more than 20 years. I’d written books on successful freelancing, had written dozens of columns and articles on the subject, and spoken at more than 50 writers’ conferences. I had developed a niche in freelancing expertise, and even when I’d segued into ghostwriting, I’d kept that identity alive. In considering a job, with a boss, with a workplace, with benefits, wasn’t I admitting, “I can’t hack it?” I’d pushed through slow periods before, but I’d never come close to even considering caving and getting a full-time job. And if I wasn’t a freelancer anymore, then who would I be? I’d been a freelancer longer than I’d been a wife. Longer than I’d been a mom. My freelancing time had easily comprised the bulk of my adulthood and my career. If I said, “so long,” what did that say about me?

 

When I looked at the list, I realized I’d forgotten the fact that a job meant that I would have a place to go, 8.5 hours a day. I’d thought that might be a con, but my anxiety had been ratcheting up over the last few months. Like the slow tick/tick/tick of a wooden rollercoaster on its ascent, I could feel it creeping up on me. I ran more, consciously worked on deep breathing, stopped trying to multitask (so much), and talked to my shrink. Yet, it was growing, incrementally, but inevitably, and I was running out of tools to manage it.

Being in a place where I was given work to do, and doing it, would provide a certain amount of consistency. Of routine. Of enough demands that I would return home pleasantly but not exhaustively tired. I’d have punched my work ticket for the day, and my evenings would be spent parenting consciously, intelligently, and thoughtfully. (Was I rose-colored-glassing my future? Of course. But I was too enamored of the idea that my anxiety might be under control to give it much mind.)

I was so enamored that I capitulated on the salary. My plan was to hold out for $50,000, but the partners held firm at $45,000. Frank was apologetic but made it clear that the figure had no flexibility. It was a take-or-leave-it situation.

My gut had told me I wanted the job. But the what-ifs threatened to swamp me before I accepted it. I called my longtime friend Polly, a fellow freelancer who wrote extensively about spirituality while being one of my few friends who swore nearly as much as I did.

“I’m taking it,” I said, a little breathlessly. I was walking to the store a half-mile from my house to pick up cat food and get a quick exercise break in the middle of the day. “And I’m going to write about it. I’m going to write about my experience,” I said, warming to the idea. “I’ve already got 2,200 words written, and I don’t start for three weeks!”

“Hell, you can write the book before you even start the job!” she yelled. “Just leave a bunch of blanks to fill in, and then tell people they have to do stuff so you can finish the book.” We cackled.

I told her I’d be working with a lot of Millennials. “I know next to nothing about Millennials,” I said. “Hashtag clueless. Except I know hashtag is outdated too.”

“Shit! I just started saying hashtag!” We cackled some more. “Well, I’m 50, and I don’t give a shit anymore. The other day I said something apparently sarcastic and; Jerry said, ‘that was unnecessary,’ and I said, ‘who cares?’”

Because that’s what happens around the time you hit 50. You no longer give a shit what people think. Polly and I gabbed and cackled and swore some more. Before she hung up, she offered some advice.

“You said you’ve anxious about the job,” she said. “Of course, you’re anxious. You’ve been freelancing for like 20 fucking years!”

“Twenty-two,” I interrupted.

“Whatever. Anything new is going to make anyone anxious. Especially a smart person. But you’ll get into it. You’ll freak out sometimes, and it will be fine. You got this.”

“Yeah, I do.”

“And write! Write it all down! I gotta know what corporate America looks like nowadays.”

“I will.” I hung up and tossed cans of cat food into my canvas tote, thinking about what she’d said. Yes, new things are bound to make you anxious. That was normal, not diagnosable. Instead of fretting over my anxiety, I could treat it as excitement, the natural response to something novel or new. Wow. That seemed a lot more palatable.

A few days before my first day at work, I ran into Sy, a 50-something financial planner whom I knew from Peet’s. “I heard you took a job!” he said, and I filled him in on what I’d seen and what I expected.

“You don’t know what it will be like until you get in there,” he said. “It’s like dating. Someone sounds amazing on paper, then you start going out, and two weeks later, you’re like what the hell was I thinking?” He drank some coffee. “You know, I quit a job after three days once. I was hired to be the CFO for a carpet company. It was a family-owned business, and during the three days, not one person came into my office to introduce themselves. So, I quit. You get in there; it turns out to be not what you expected, and you quit —well, you haven’t risked anything. You can still go back to freelancing and ramp up your book business.”

I nodded, trying to keep up with him.             

“So, it’s a Millennial work environment?” Sy continued. “I’ve never worked in a Millennial environment. I mean, I know Millennials, but I haven’t worked with them. I usually run from them.”

I laughed. “Well, I know a few Millennials,” I countered, thinking of Mel, who bartended at the pool hall where I played in a weekly league. And Jordan from Peet’s. I know two Millennials, I thought proudly. And I like them. And they like me! That had to bode well for my future employment. 

But even if I could connect with my Millennial coworkers (I hoped), I wasn’t in my 20s anymore. Or my 30s. Or even my 40s. Most days, that didn’t bother me. Others, I was simultaneously amazed and horrified that I’d gotten so old. I consoled myself with the fact I looked okay, even pretty damn good some days, with clothes on, and I wasn’t in a profession like pole dancing where the perceived perfection of my body truly mattered.

Even so, a harsh or unflattering light revealed a whole host of indignities. Sun damage. Sagging skin. Cherry angiomas splattered across my torso. Cellulite on body parts that had never before had cellulite—like the fronts of my upper arms. When had that happened? Random body hairs that had never appeared before—like a chin hair as coarse as toothbrush bristle that would sprout appear every few weeks. In addition to my forehead lines, I was now sporting two vertical lines between my eyebrows that were apparently permanent. Recently, I’d developed the dreaded “meno-pot” and was starting to understand why women of a certain age opted for flowing tunic tops and loose waistlines.

But I was healthy, I reminded myself. And strong. My body, apart from various running maladies that cropped up now and again, could still hammer out four miles on the treadmill in a little over 36 minutes. I lifted weights a couple of times a week. I could (and did) shovel my driveway every time it snowed.

Most days I felt pretty good when I woke up. About 25. And since I’d been feeling 25 since I was actually 25, I was hopeful that I could keep my youthful outlook permanently.

Still, some things had changed. While I’d had student loans and the stress of a career as a newbie attorney to contend with, those worries were small fry compared to being a parent. My biggest ones almost always revolved around my kids and tended to center on whether I was doing a decent job as a parent or failing spectacularly.

In theory, the idea of freelancing and parenting full time worked. I had flexibility and adapted my schedule to the kids’. But the reality was that as a single mom, I was often distracted, stressed out, tired, or simply crabby with my kids. Then, I felt guilty about being a horrible parent. Even when I felt that I was doing okay, I was always peripherally aware of how fast my parenting time was elapsing. But was I truly enjoying it? Was I doing the best I could? Most days I simply was grateful to have two healthy, (mostly) happy, well-adjusted children whose biggest problems were that they weren’t allowed to have an Xbox and television in his room (Ryan) and were forbidden to sit on my iPhone all day, making Tik Tok videos (Haley).

I was balancing my desire to be a good (well, great) mom with my desire to have a man in my life again. My boyfriend, Walt, didn’t have kids and had never dated anyone with them. He had soon discovered that I oriented my entire life around my kids, as parents do.

Since we lived an hour apart (we met online, thanks to Zoosk), we typically only saw each on weekends. The kids were with me for ten days and with Erik for four, and on those weekends, I was free … unless Ryan had a travel basketball tournament or Haley had a soccer game or some other event that I didn’t want to miss. On the weekends the kids were with me, Walt was thrown into an insta-family whether he wanted one or not. I wasn’t sure whether he did, which meant I wasn’t sure whether we had a future together though we’d been going out for nearly a year.

On paper, we were a mismatch. I tended to rush and juggle and multitask and to always be thinking of the next thing. He was a union plumber who walked slowly, talked slowly, and moved slowly. He was thoughtful, measured, and calm. While I was always striving for the next project, the next client, or the next challenge, his default was set at “content.” I was maddened by it even while I envied his ease in the world, with himself, with everyone.

I’d been attracted to that ease and loved that he made me laugh, that he rarely lost his temper, and that he called me Zippy. I loved his size, his smile, his big rough hands that were always scratched and scarred, and the way he always looked out for me. He was constantly fixing stuff in my house that I didn’t realize needed fixing. Hell, he unclogged my shower drain on our second date! For Mother’s Day, he bought me a toilet, replaced the old one in my basement bathroom, and helped me clean out and organize my garage, which I hadn’t done since moving in more than two years prior.

But he didn’t read books, and he wasn’t interested in architecture, museums, or foreign films. He watched terrible network TV … what I considered pablum for the masses, like America’s Got Talent or The Masked Singer or whatever idiotic show was broadcast on a typical weekday night. He didn’t even have cable! He didn’t bring much to the intellectual party that I often wanted to host—not like most of my friends, whom I tended to cherry-pick for being well-read, intelligent, and insightful. Because at heart, I’m an intellectual snob.

Dating Walt was like tending a hard-to-kill houseplant. I didn’t have to put in much time or energy into our relationship because we didn’t see other that often. The relationship thrived even with minimal care. And minimal care was what I needed. I’d spent a lot of time and emotional energy putting my toe back into the dating pool and had had more than a dozen in-person “encounters” (I refused to call them dates) with men I’d met online, looking for someone I had a connection with. That had proved to be more difficult than I’d expected.

Since my divorce, I’d only met two men I was attracted to, and the fact was I’d known both of them beforehand. Gabriel and I had been members of the local swimming pool board together, and after his divorce, he’d bought a house down the street from me. We’d gotten to know each other better after he moved in, and I’d found that I liked him. A lot. He was smart, well-read, funny, and sexy, and also very freshly divorced. Two of his kids had been adopted, and we talked about everything from adoption to marriage to sex to heartbreak to the meaning of life and our favorite standup comedians. Gabriel got my literary references and obscure jokes and deftly returned my conversational volleys. We bantered back and forth by phone or text and called each other “twin” for thinking the same thing so often.

But Gabriel was still grieving the loss of his marriage and family and trying to figure out what his life was going to look like. I didn’t want to get involved with him and have my heart broken and knew we were better off as friends.

“You need pussy,” I’d told him. “You need transition pussy, and I am not going to be your transition pussy.” He’d burst out laughing and agreed, and we’d settled into a friendship unlike one I’d had before. We flirted. Joked, and tried to impress each other with our big words, secure in the knowledge that we weren’t going to have a Relationship. Or even sex. We’d discovered our former marriages had had a lot in common and worked on what I called bucket-filling.

“Have I told you how smart you are? Super smart. And you’re a good dad, a good son, and a good brother; you can fix anything, and you are incredibly handsome,” I’d tell him. “You know that, right?”

“Gee, thanks,” Gabriel would say, laughing.

“Seriously,” I’d continue. “You are the complete package. Any woman would be so lucky to be with you. All my friends say the same thing.”

“You’re filling my bucket again, right?”

“Well, yeah,” I’d say. “But I mean it.”

While I was getting to know Gabriel, I’d started dating the only other available man in Downers Grove I found attractive, a widower with three kids who lived around the corner from me. He and I worked out at the Y in the mornings. I had been attracted to Richard’s confidence and had flirted with him rather brazenly until he’d asked me out.

Richard made me nervous. He was cocky, funny, and sexy, and he made me feel desirable for the first time in literally years. He also had some anger issues which often bubbled to the surface, but I’d fallen into bed with him, anyway. I’d been reminded of how much I’d missed having sex. The more sex we had, the better it got. Soon, I was thinking there was something between us, when what we actually had was a no-strings sexual relationship that worked for him because I was convenient. Even so, I wound up “catching feelings” and was stung when he dumped me. By text. (Something I likely had in common with plenty of Millennials.)

Months later, I was still smarting when I’d met Walt. I’d even warned him about it the first night we met. Walt hadn’t blinked. He’d made me laugh, listened to the torrent of information I needed to offload, and even survived what I thought was a subtle grilling designed to reveal his political beliefs and any possible racist or homophobic tendencies. He’d not only passed but surprised me over the months with his ability to remember even minor details of my life I’d mentioned in one of our less-than-fascinating phone calls.

Whatever might happen, for now Walt and I were solid. My kids were doing well. I was taking a job. What did that mean for my freelance career? I talked to my agent, Katherine, about my upcoming transition and my plan to jettison a book client who’d been dragging his feet on a proposal but to keep Nancy’s book. She understood my reasoning and supported my decision but cautioned me against disclosing my new employee status on Facebook or LinkedIn.

“I know you can work full time and ghostwrite on the side, but you don’t want it to appear that you’re doing anything that could be perceived as violating your contracts,” she explained. She was right. Every book contract included a provision prohibiting me from taking on any other project that might interfere with my ability to complete the book.

Shit, I hadn’t thought this all the way through. I had already determined that I didn’t want to completely burn my freelance bridges—what if the job didn’t work out? What if I started and it turned out I hated it? What if I got fired just a few days or weeks in? Then, I’d be really screwed. Keeping my book project and a few other freelance clients was my idea of a safety net and one I wasn’t willing to jump without. I promised Katherine I’d keep my employee status strictly private, at least for a while.

 

The Corporate Newbie’s Cheat Sheet: Should You Take the Job?

 

You’ve been offered the job. Congrats! But hold on a minute. Do you want the job? Really want it? You’re facing a big decision here.

First, do your due diligence. Have you obtained as much information as you can about the job? What will your responsibilities entail? Will you be working on site, remotely, or a combination of both? What’s the salary? What benefits will you receive? How much will benefits (like health insurance!) cost you? How long will your commute be if you have to go to the office?

I suggest you make two lists: one of the possible pros of taking the job and another of the possible drawbacks. Compare the two.

Finally, picture what your life will look like if you take the job. Will you need childcare? A dog walker? A new wardrobe or at least a few new outfits? If you’re changing jobs, will you be working more hours or fewer than before? Will your day-to-day schedule change radically (like if you haven’t been working and are going in-house) or look similar to what it is now?

            Ask yourself one final question: how do you feel about taking the job? Excited? Happy? A little nervous? All are good. A lack of excitement or the sense that you’re settling because you’re desperate, not so much. Ideally, you’re taking a job that offers a new opportunity, reasonable pay, and an environment you think you can thrive in for the coming months or years. If that feels like the case, accept that job, and uncork the champagne! 



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