Elizabeth Strout worked as a cocktail waitress, an office temp, a lawyer, and a community college professor before publishing her first novel, Amy and Isabelle. She won the 2009 Pulitzer Prize for Olive Kitteridge (which was turned into an HBO series). Her seventh novel, Olive, Again, is coming out in fall 2019. Here’s how she made ends meet.

This interview has been edited and condensed for clarity.


Medium: Did you study writing in college?

Elizabeth Strout: I studied theater. It was like writing, because I was always trying to be another person. But I never took a creative writing class. I can’t say anything more than my intuition was “it will not be good for me to sit among my peers and hear what they have to say about my work and to say things about their work.” But I was always writing. There was one professor who knew that, and he was the chairman of the English department. He believed in me. I would show him my stories, and when I had a paper due for his class, he would give me a short story instead. It was our secret.

After graduation?

I went to England, because I didn’t speak any other languages, and I was running away from parents who expected me to be doing something. I lived in Oxford for a year and worked at a pub, wrote during the day. I just kept writing and writing. And then I got homesick, so I came back to Lewiston, Maine, and worked at, honest to God, every restaurant — breakfast, lunch, dinner. I also worked as a piano player in a bar. It was horrifying.

Were you taking those jobs to protect your writing time?

You know, I kind of did. I preferred waitressing in the evening, because the breakfast shift is hard work, terrible tips, and then your day is killed. But as a cocktail waitress, I made a more money and had my days free to write.

Did you stay in Maine?

I moved to Boston and started temp work. Once in a while, I was lucky to find a job where they didn’t need me to do much more than answer the phones, and then I’d have a typewriter and would type my little head off for eight hours a day. There was one man who even said, “Oh, type away, I don’t care what you do.” That was just heaven. If I could have done that all the time, I probably would have kept temping.

Why didn’t you?

At that point I had been a cocktail waitress and temp for three years. I thought, “Obviously, not one person is interested in my writing, so I need a job.” This was the 1970s, and I had a real social conscience — well, I still do — and I actually thought, “I’m going to law school, and I’m going to do good work during the day, and then I’ll come home and write.”

Did you write while in law school?

I remember reading Nabokov in my constitutional law class, because reading was as important to me as writing. Pnin was a small book that could fit inside the con-law text, and nobody would know I was reading. Then I began to realize that I could skip a lot of classes, so I would write anytime I could skip a class. I dropped out after the first year.

You were in law school at Syracuse. Did you consider transferring to the school’s writing program?

Even though I hung out with the writers in the MFA program, I did not want to become part of it. I noticed they talked an awful lot about writing, but I never saw their results. And I thought, “Well, they’re fun to hang out with, but I don’t need to talk about writing all day. I need to write.” So I got a fabulous job temping at the medical school, where I could type all day long. I wrote a novel that was very bad. Then that gig ended, and I had to go work in the department stores. I couldn’t sell any clothes, so they stuck me on the mattress floor, where nobody ever came.

How did you know the first novel was bad?

It wasn’t so much that I thought it was bad—I just understood that it wasn’t good enough yet. I kept thinking, “Where am I going to be most comfortable doing my writing?” So I went back to law school, because I could get more writing done during law school than I could when I had to support myself. I wrote for two years during the day while I went to school, skipping any class I could. When I graduated, I had $7,000 in debt, and then I had to be a lawyer, and that was absolutely horrifying.

I would close my office door and read Colette. I mean, I was just a mess.

Why so horrifying?

I was doing what I wanted to do — working in legal services — but I was just so bad at it. I was hired straight out of law school—three of us lawyers and a social worker trying to get developmentally disabled clients SSI and all the other payments the state was always cutting off. Schools were not giving the services they were supposed to, and I would have to call and say, “We’ll see you in court.” And I would think, “Oh my God, what am I going to do in court?”

I was terrible at it. I lost every single case. I went to court one day to file and hadn’t even brought the right paper. I was pregnant, and there was one judge — they were all men back then — who said to me, “You have nice legs.” And then he found against my claim. I would close my office door and read Colette. I mean, I was just a mess. I didn’t know what I doing, and I felt so responsible for these people.

How long did you stay?

I was a lawyer for six months. Then we got a new president and the funding was cut. It was very awkward, because I believed the funding should not be cut, and I went to demonstrations to protest. But I also knew I would be the first one fired if they were to be cut, and I wanted so much to be fired. [My then-husband and I] moved to New York City, and the baby was born. The very first week there, I took a class at the New School in fiction writing.

After all those years of your intuition telling you to stay out of writing classes, now you start?

Well, it was an evening class, and it wasn’t in the writing program. It’s interesting why my intuition said to take it, but I did, and it was wonderful for me. I met my friend Kathy Chamberlain, who has been my first reader [of all of my manuscripts] ever since. She taught at [Borough of] Manhattan Community College and got me a job there. By then, I had started to have stories published in literary magazines, so the chairman of the English department there liked my work and liked me. They counted my law degree as a graduate degree, and I was able to adjunct.

What did you teach?

I taught literature and composition there for 13 years. I loved both, especially literature, because so many of those students didn’t know reading could be fun. I was young and would come in so enthusiastic about a book that they would sort of sit up and say, “Oh.” Years later, I met a student of mine on the subway who held up a collection of Raymond Carver’s stories and said, “Look what I just bought.” I was thrilled.

And you didn’t have to be a lawyer anymore.

One of the first things my father-in-law did was write a check for $7,000 for my law school loans. I never forgot that. When he wrote that check, I realized, “Oh my God, I’m free.” But I wasn’t free, because I had a husband and a child and a house to take care of. As far as squeezing out time for writing, I was pretty much on my own.

When the checks for my first published novel came in, I started to leave my first husband. He was great. We didn’t get divorced for years so I was able to keep his health insurance.

Do you remember what a writing day looked like for you at this point?

We moved to Hartford for two years when my daughter was 18 months. She was always a very good kid. She would sit quietly on the couch while I read a magazine, and she would read her magazine upside down. But I could only write when she napped, and she had trouble taking naps. So I would put her in the car, and she would fall asleep, and I would drive to the parking lot of the mall in Farmington, Connecticut. Very quietly, I would turn the engine off, and she would stay asleep. Then I would have maybe an hour or an hour and a half to work on a story.

How did this affect your writing?

I realized that if I was writing a story where I needed to get a character into the grocery store, I might spend the whole morning trying to get them into the store only to realize the pages were just dead. And so I learned early on: “Forget getting them into the grocery store — just be in the grocery store and worry about it later.” Whatever my emotional hook was that day, I would take that anxiety and transpose it into something the character was doing. Not the same problem, but the same anxiety. That way, there would be a heartbeat to the scene, or a better chance of it.

I read that you never write a novel from beginning to end, that you always write scenes and then organize those scenes later. Do you think it comes from those days?

Yes, absolutely. Now, when I write, I would say 90 percent of the time I’m writing scenes. And I learned that from those days.

At what point did you begin earning enough from writing that it changed your life ?

I think when the checks for my first published novel, Amy and Isabelle, came in, I started to leave my first husband. He was great. We didn’t get divorced for years so I was able to keep his health insurance. But I wouldn’t have been able to do that if I hadn’t made some money on my own and my daughter weren’t going off to college.

Once you finally had more than three hours a day to write, what did you do with the time?

I made a complete mess of it. The jolt of all those changes at once — it was very hard to live on my own. I had been married almost 20 years. I was supposed to write, and it was scary, because I didn’t know if I could. My next book did not do very well. I remember my father-in-law’s accountant brought me into his office and asked, “What are you going to do? Because you don’t have any money.” I had enough money to last a few years, and I said, “I’m going to write.” And he just looked so sad. He said, “You know that never works out.” And I said, “Well, I’m going to do it.” And I left. It was horrifying. I was so scared.

Ten years after ‘Amy and Isabelle,’ you published ‘Olive Kitteridge,’ which won the Pulitzer Prize and was adapted into an Emmy-winning miniseries on HBO. Your successes — both critical and financial — continued with your next three novels. Now that you no longer need a day job to support your writing, what does your writing day look like?

I still prefer to write in the morning as soon as I get my husband, my second husband, out of the apartment. Or, if I’m in Maine, I have my own studio. I try to put lunch off as far as I can, because something about having lunch makes my energy lower. Sometimes, in the evening, I’ll go back and look at what I’ve worked on—although that’s always risky. The important thing is to leave my day’s work thinking, “I know what I’m going to do tomorrow, and I think it’s going okay.” If that’s not true, then I find that out in the morning when I still have enough energy to deal with it. But if I find that out in the evening, I worry all night.