Trials and Tribulations from Freelance Worker to Full-time Employee – One Woman’s Journey

SD METRO Associate Editor Douglas Page spoke with Kelly K. James, author of the new book, The Book That (Almost) Got Me Fired. She tells a compelling story about going from freelance writer to full-time employee, navigating bosses, younger coworkers, bringing up children, and showing how she made a successful transition – with some advice spiced in, too. This transcript was edited for brevity and clarity.

SD METRO:              What prompted you to go from freelance writer to full-time employee?

Kelly K. James:              I was ghost-writing, and the work was erratic. I would be very busy on a proposal or very busy with a book, and then an agent or an editor would sit on a project and at one point I had four proposals in the works and none of them sold. If the proposal doesn’t sell, you don’t have a book contract.

                                    The company was hiring. Plus, it was 3.2 miles from my house. I sent a resume on a whim, got an interview, and they offered me the job. So, I told one of my friends, “You know what? I’m going to go in-house, and I’m going to write about it.” I’m going to be like Barbara Ehrenreich writing Nickel and Dimed. It’s going to be my look at corporate America.

SD METRO:             What was the environment like?

Kelly K. James:              It was a much more casual than I was used to. I’d always worked in law firms. I had worked at Pampered Chef a couple of times, but this was a very, very chill atmosphere. Most of the people wore sweatshirts. I would say about 50% had giant headphones on and it was quiet as a tomb with very little interaction except for the sales guys.

SD METRO:              You write so well about the cultural difference between working for yourself versus working in an office. How big of a shock was it to you to go back to an office after being away for 22 years?

Kelly K. James:              Sitting at a desk all day. I’ve worked from home for a long time. I get up a lot, take my dog around the block, throw in a load of laundry, get a snack, maybe do some dishes, but I don’t have to sit in one place all the time. And I don’t care how progressive your office is, they’re not going to be okay with you getting up and leaving every hour to go for a 5- or 10-minute walk.

                                    The first two or three weeks left me exhausted from sitting motionless all day. The other thing was I had to get up, shower, put on adult clothes and be at my desk where, in comparison, and my neighbors will tell you, I walked my dog in my pajama bottoms and a sweatshirt many times because working from home, that’s one of the luxuries. You can wear what you want and even if you’re on camera, we all have the nice top for the camera and the pajama bottoms on the bottom.

                                    Plus being on someone else’s schedule. And I think I would add third as a freelancer, when I know I’m done for the day, I’m done. When you’re working in corporate America, you can’t go to your boss at 2 or 2:30 and say, “I’m pretty much done for the day. I’m going home.” So, people stay at their desks and look at Facebook or go on Wikipedia or find other ways to waste time.

SD METRO:             One of the things I’ve seen written, especially on the heels of COVID-19 work from home policies, is that some people can’t handle working in an office anymore. Did you see that?

Kelly K. James:              I didn’t, but that’s because I call myself an extrovert in an introvert’s job. I had dinner recently with two of the women I used to work with at the company. My friend Elaine was saying I was the only person in the office who said, “Good morning, good morning.”

                                    People responded, but no one was super friendly. And then I realized, “Oh, they don’t want to have a conversation. They’re just in the nook to get their coffee and sit down.”

                                    As a creative professional, I’m much more efficient and effective if you let me work from home. I can get much more done. And then there’s always going to be some people who say, “Well, we want you in the office because we want to brainstorm and we want facilitate this.”

                                    There’s some value in that. When I onboarded with my current company, I went to Atlanta for four days and met all the people at the office. It’s easier to connect after you’ve met someone in person. If you always work from home, it is a skill you need to have in case you return to the office.

SD METRO:             It sounds like you were worried your social skills were deteriorating.

Kelly K. James:              Social skills are important and connection like actual connection is important whether you’re at the office or in your relationships or just talking to somebody at the coffee shop or talking to my neighbors when I’m walking my dog.

SD METRO:             You took what seemed to be a rather low starting salary.

Kelly K. James:              I was offered $35,000 and I said, “I can’t do that. I mean, I’ve got two kids.” They came back with $45,000, which was less than what I wanted, but again, I took on the job – to get the health insurance and write about it.

                                    And I still had a book under contract that I had to write so that income was going to come in. And then I knew I was still going to freelance, so I could still do it. Everything’s a trade-off. When you choose option A, you’re saying no to option B.

SD METRO:             Millennials come under fire for all sorts of reasons, and I’m not here to take a view on them one way or another, but how would you describe them in the workplace compared to maybe other generations you’ve known whether it’s the Baby Boomers or Generation X?

Kelly K. James:              The office was mostly Millennials. I don’t think Gen Z was there yet. But as someone in her fifties, I thought, “They’re not going to like me or they’re going to call me grandma.” I was more concerned about working with them in the sense of, “Will they accept me?” Not, “Oh no, I have to work with Millennials.”

                                    Millennials are great. And I think it comes down to attitude. The sales guys were Millennials. The SEO guys were Millennials. I would go over there with my coffee cup and say, “Hey, I got questions. I don’t understand why we can’t use the plural keyword. I don’t understand this. Can you explain this to me? Can you help me with this?”

                                    As we get older, there’s more of a resistance by people to admit what they don’t know. I have never had a problem saying I don’t know how to do something, or I don’t get it, or can you explain this? I typically couch it in terms of, “Here’s what I’ve done. I looked at this and this, and I still have questions.”

                                    So, you’re not asking for someone to spoon-feed you. I think we all need to let go of those preconceived notions of, “Okay, Boomers or Millennials are this or Gen Z is this,” and just focus on people as individuals.

SD METRO:             I spoke with somebody (San Diego State University Professor Jean Twenge) who said something similar. One of the things that Millennials have done well is improving life in the workplace. They won’t stand for conditions our grandparents or parents went through.

Kelly K. James:              What I see is a better work-life balance. Pretty much everyone I know has something they’re passionate about in their life. It’s not their job. It’s something else. And the other part of that, too, is I work with several people in their mid-twenties to early thirties at my current job, and they are confident. These women are confident in a way I was not confident in my twenties and maybe not even until my thirties.

                                    And especially for women, I think that’s empowering. I get irritated when people are, “Oh, they’re special snowflakes.” Partly because I don’t think that’s the truth and partly because I’m raising two people in this generation, and I don’t want them to whitewash my whole generation with whatever they think we are.

                                    One of the best questions to ask is, “What’d you do this weekend?” or “What’s something you’re really excited about?” I play eight-ball on Thursday nights and last week, I think she’s 27 or 28, and we’re talking and a B-52s song came on and I was like, “Oh, I actually saw them in concert. They’re one of my favorite bands.” She’s like, “They’re one of my favorite bands.” I’m like, “You know the B-52s?” When you look for bridges, you find out you have more in common than you think.

SD METRO:             How did it go over when you told the kids, “I’ve taken this job”?

Kelly K. James:              They were more concerned with whether the job was going to change our lives. And once they knew that it wasn’t, they were fine with it. They were 10 and 5 years old.

SD METRO:             You spend a lot of time talking about your boss, Frank. What was he like?

Kelly K. James:              In a different situation, we could have been friends. He was someone who couldn’t completely trust the people who worked for him. And I’m someone who does not do very well in a micromanagement situation. He was demanding. Could be fair. I did learn quite a bit about my job from him and about interacting with people at the company.

                                    But one of the things he said to me was, “The company hasn’t had somebody like you before. You ask all these questions and most of the people here just want to come and do their jobs and go home.” And I said, “I just want to understand how all the different pieces fit together.” I think it was more like I was a round peg going into a square hole.

SD METRO:             It would seem that writing outlines for reclaimed wood furniture companies, basketball camps, aircraft refurbishing companies could get monotonous. How did you make it interesting?

Kelly K. James:              Some parts of a job you just can’t make interesting. Doug, I’m sorry. I’m just a big believer in to-do lists. And some of the clients were actually really fun to write about and write for, and some were not. Compressed Air Systems was one of the ones where I was like, “I know nothing about this.” A manufacturer that made ball bearings. I mean, I like writing about health and wellness and service journalism, but depending on the day, I always had my to-do list. And I would put the worst task first. I’m a big believer in eliminate the ugliest, do the thing you most don’t want to do first, not necessarily the hardest thing, the thing you don’t want to do, and just kind of tick them off the list.

                                    And then if I had a client that I really liked writing for, maybe that’s my mid-morning break. But again, coming from a freelance background, sometimes you’re writing for clients or writing about subjects you love to write about, and sometimes you’re not. That’s the job that’s being a professional writer.

SD METRO:             You’re at the office and you come across someone who’s got the big title. And yet as you sit there, talk to them, you realize, “Gee, I might be old enough to be their — dare I say it? – mother”? Was that a shocking moment or did you just roll with it?

Kelly K. James:              The partners were pretty much in my age group. We probably grew up listening to the same bands. But then the next level down, there were a fair number of people who probably could have been my kid. But again, at the company I work for now, our CEO, I don’t even think he’s 40. He’s a wunderkind, but we speak the same language.

                                    One of the good things about going back to work in your 50s, if you have an open attitude and you understand smart people come in every age, you can connect with somebody. I’ve worked for people much younger than me, and it’s never been an issue. I’m not going to say, “You know, I’m old enough to be your mother.” I can think that, but I’m not going to let it play out in my demeanor.

SD METRO:             What did you like most about the job?

Kelly K. James:              Connecting with people. I listened to the sales guys, asked them questions, and they came to understand that I was truly interested, so I was able to learn a lot from them. We had many processes, one in particular where it was a certain kind of content that we were sending out to writers, and I suggested to my boss we could do this ourselves because it was just inserting keywords into existing content. It wasn’t expanding the page and it wasn’t writing an entirely new page, we call them reworks. And in the world of SEO, you basically take existing content and you put the keywords in the existing content. So it is kind of like a little puzzle where you have this piece of content, where are we going to put the keyword, where does it fit?

                                    And I suggested this process and it was okay, and it saved our department a lot of money. Plus, it gave me and Alyssa another project to work on. I like developing efficiencies.

                                    I also loved being put on client calls when we had a new one because I’m a former ghostwriter and journalist. So when we were on the call, I would say, “Tell me what you want in terms of your content. Who’s your customer? Who’s your client?” And then I would write up my notes and share them with everyone who was working with that client. No one had done that before.

SD METRO:             It seems where you relished those moments the most because it provided you with a deeper understanding of the clients.

Kelly K. James:              It did. It was an acknowledgement that we’re humans. I remember this one client didn’t want to use the word elderly and I agreed. Being able to talk with her about it was much better than, “Here’s why we’re using this keyword” and just that acknowledgement of humanity, and also the acknowledgement that when someone tells me, “This is what I want,” I can say, I hear you, and okay, the owner of your company does not use contractions. That to me is a little different. I use them all the time, but it’s in our notes. So, I think that’s very valuable, and people want to be heard, listened to and understood.

SD METRO:             What did you like least about the job?

Kelly K. James:              Having to be there. I pushed immediately to be able to work from home two days a week. And then I got them to agree to three days. And I mean, I was pushing for five days a week, and then we got COVID.

SD METRO:             Was work-life balance better at home or at the office?

Kelly K. James:              Work-life balance is a myth. Nobody can ever achieve it for longer than two or three days in a row, and then it goes by the wayside. The biggest challenge was being chained to my desk for 8-1/2 hours a day. When you’re freelancing and working from home, you can go to the store at noon or take your child to the doctor or all the little things, which I call “Life Work” – getting the dry cleaning, changing the oil in the car. Now I have to do them not during the day because I’m at work. I have to do them when a lot of other people do them.

                                    Nobody wants to go to the grocery store at 4:30 or 5 p.m. You’re tired, hungry, and buy all the bad food. It was really important for me to cook dinner every night for my kids, but I gave up on that after two or three months.

SD METRO:             You list why it’s important not to piss off your boss. Did you piss him off frequently?

Kelly K. James:              I did. I’ll give an example. This idea of me being on the client calls, I had suggested this early on. I said, “Wouldn’t it be great if we had somebody from our department to be on these client calls at the outset? That way that person could find out what they want with content and then we wouldn’t get clients unhappy with the content we’re producing.”

                                    And my boss said, “We don’t have anyone in the department to do that.” And I said, “I could do it. I’d be happy to do it.” Well, he said no. So I thought it was a good idea. So I went over his head and I went to the VP and suggested this idea, because I haven’t worked in corporate America for 22 years. So that was the kind of employee I was, and he was not happy with that kind of action, and they decided to put me on the client calls. And when he told me that, I couldn’t resist saying, “This is what I suggested.” To be fair, I think there were issues on both sides of the relationship.

SD METRO:             When you went back to corporate America, it sounds like there were a lot of coordination issues with your ex-husband. Did you two work well together when it came to the kids?

Kelly K. James:              We did. I talked to Eric before I took the job. He was very flexible and very supportive. I think he worked from home pretty much exclusively at that point, but sometimes he had to travel. So when he traveled for work then, and if it was during his time, the kids were still with me and we were very flexible, and we had a dog that went back and forth, and our cat went back and forth. I can’t imagine not having that kind of co-parenting relationship.

SD METRO:             Tell me about the approach you took to getting a raise.

Kelly K. James:              I started talking about a raise having been there for a month or two, which probably wasn’t smart. I did ask for a raise at six months because I recall during the interview that my boss said I was taking much less money than I wanted, and he said I could bring it up at six months.

                                    So, when I did, I had put together a two-page letter that said, “Here are all the things I’ve done. I came up with this new process and that saved our department about $5,700. I was hired to do outlines, but I’m doing all these other tasks and I’m on these calls”, and I tried to show my value in terms of, “This is what I have brought. This job was paying $45,000, but this is actually what I’m doing, so I should be paid more.”

                                    And they said no. I wasn’t happy. I did get a raise at the end of the year and continued at that company for another year and a half and received more raises.

SD METRO:             What prompted you to leave?

Kelly K. James:              I didn’t want to be the director of content, and that was the only job that was above me in the content department. I also wanted a little more freedom and flexibility. I found a position with a Swedish company that was remote. So that’s where I ended up going.

SD METRO:             When you think about everything that you went through professionally and personally, what was the biggest thing you learned about yourself?

Kelly K. James:              When you start a new job, it’s stressful. You don’t know the people. You don’t know who you can trust. You don’t know how to do the job. And you may not know how to log on to get into the spreadsheet. You don’t know who you’re going to be friends with. You don’t know the relationships. You come in cold.

                                    It made me realize who I was. I had this idea that, “I’m a freelancer, I’m a freelancer first and foremost”, that I had these skills that could translate into the workplace. And maybe I didn’t have to be a freelancer, but I still felt like a freelancer on the inside. I was proud of myself for taking the challenge and wanted to quit many times but didn’t because I promised myself I would stay a year.

                                    At the end of the year, I got an okay raise, and I was like, “Well, I guess I’ll stay for another year.” I was proud of putting myself in uncomfortable situations instead of being afraid to.

SD METRO:             It sounds like you discovered you’re far more resilient than you expected.

Kelly K. James:              Thank you. That’s my answer, Doug.

SD METRO:             These days you’ve got a lot of women and men who have worked at home, stayed at home. What’s the best piece of advice you can give in terms of having done what you have done and then going back to the full-time gig at the office?

Kelly K. James:              Decide what your absolutes are. I gave up the idea that I’m going to make dinner every night. It was causing too much stress. But one of my absolutes, maybe three to five mornings a week, I would go to the Y and work out before I went to work.

                                    I have very good friendships, and staying connected to friends helped me tremendously. At lunchtime, I would walk around the corporate area where our company was and call one of my friends and vent for 15 or 20 minutes. I think maintaining relationships is important. It’s super helpful to have people who are already in corporate America because your freelance friends are probably not going to understand what you’re doing.

SD METRO:             And that way you’ve got some people you can bounce ideas off of or learn ways to strategically negotiate what you’re going through.

Kelly K. James:              When I went over Frank’s head with that idea, and I told a couple of my friends who work in corporate America, they were like, “You did what?” I was like, “I didn’t know.” “You never do that. You never go over your boss’s head.” I was like, “I know now.”

SD METRO:             Thank you, Kelly.