Freelance Perks: Serious Time Off

Here is what it is like to be a mid-career freelance editor and writer. After building up subject expertise and reliable contacts and great clients, I get to take a month off. Like, a whole month. This month, to be exact.

How I Planned It

In the spring, Mr. KHG and I discussed taking time off. He has a regular job, the kind where you can accrue vacation time. He often works way more than his 40 hours a week (it’s a social justice nonprofit type of gig), so he has accrued as many hours as they will allow. He can take an entire month off.

I looked at my schedule and my little stable of regular clients and said, “Yeah. I think I can do that too.” So I made sure to tell everyone months in advance — early and often — that I would be out of the office for August. All of it.

Being a mid-career freelancer, I have long had the emergency funds built up and ready to deploy if necessary. I have a business savings account, a personal savings account, and a retirement plan. The first years were rough, but as things smoothed out in about year five, I was able to build up these safety nets for myself. That means that now, 13 years after going freelance, I can plan to take a month off.

The Lead-Up

There is a lot of advice in the world for people who are new to freelancing and very little, I’ve found, for people who’ve been doing it a while. This is probably because we’ve made it through the scary years and have figured out how we work and why.

But sometimes, you want to see how someone else did a thing rather than inventing every, single, tiny process for yourself. Taking a month off probably won’t work for people who are just starting, but if you’re a few years in, it probably — surprisingly — will. Here’s how I did it.

  • I blocked off August in my calendar so I wouldn’t schedule a project start date or deadline during my month off.
  • I told everyone, my assigning editors for articles and my book editing clients, that I would be taking August off.
  • I planned all new projects to either end before August 2 (my last day in the office) or begin September 3 (my first day back in the office). I have enough new work coming in after vacation that I know I won’t be broke later in the year.
  • I communicated to all clients that I worked with in July that their deadlines for getting materials to me had to be met. If they didn’t get their manuscript back to me in time, I wouldn’t be able to finish editing it before I left the office. People were very cool with this! I did get one manuscript a day late with a lot of apologies and hopes that it wouldn’t wreck my vacation schedule (it didn’t; I’d built in a schedule buffer).
  • About two weeks in advance, I added a line to my email signature that included the days I would be out.
  • On my last day in the office, I set up a very bare-bones out of office response.

The key here, my mid-career friends who may be reading this, is that no one will forget you after a month off. They’ll hardly notice you’re gone. They know and like your work and can survive with the other freelancers in their contacts list. Or if you’re the only one who can do what you do, by your giving them this much advance notice, your clients can plan around your absence.

A lot of us chose freelancing for the freedom (cue George Michael video). Then we found ourselves working in a near-constant panic in an effort to create a steady-ish income. But eventually that steady-ish income does arrive, and with comes that freedom you wanted in the first place. Don’t forget to use it!

On Finally Hiring Help

I am currently on my lunch hour in my office. I don’t usually eat lunch in my office, and I don’t usually work during lunch. But today I am eating leftover vegan quesadilla at my desk because there are two super cool people cleaning my house right now and I do not want to interrupt their flow. That’s what the cats are for.

(They love the cats.)

I have long wanted help running my business, but I am clueless as to how one goes about doing that. What would that other person do? Would I have to tell them how to do everything anyway, which would negate the whole point of having help? How many hours of work would I even have for another person to do?

The cleaning people are my baby step toward hiring help. Because they come in once a month and clean the living hell out of my house, I do not have to take any time to do that. I can keep up with dishes (we have a dishwasher) and laundry, and Mr. KHG can keep up with cat litter and garbage. The occasional wipe-down on the counters is fine. The two hours or so that I pay these cleaners for cleaning once a month frees up hours and hours of housekeeping time for me.

What have I done with this housekeeping time? I’ve gotten this blog back on track, for one thing. I’ve mapped out a marketing plan for the fall to grow my editing business. I’ve been doing hours of French homework most nights. I am doing a ten-day Adobe bootcamp to do more cool social media stuff, like this Helen Oyeyemi quote thing that I made for Instagram Stories (@kristen_hg).

The cleaning people are straight-up pros. I had to give them a wee bit of instruction the first time (don’t bother trying to dust the roleplaying minis, for example), and then they set to cleaning. They’ve been around for three or four months now, and it has made a huge difference in my productivity and my ability to see past the next project and plan for my future.

I’m still not sure I’m ready for an assistant to help me with my actual work, but I can see how it might be really great in the future if I budget the money and a little time, at least at first, for it. But since I’ve hired out the housekeeping, those admin tasks that I used to dread aren’t so terrible anymore. If I don’t have to worry about how disgusting my stovetop is (whew, it was gross, y’all), then I can worry about keeping my clip files up to date and, you know, writing more blog posts. I may even get around to creating the newsletter I’ve been trying to imagine for, like, two years.

How I Became a Book Editor

I’m realizing now, after working as some variety of editor since 2004, that people take many different paths to become book editors. There are degrees and certificates, and there are internships and mentors. I went the DIY route, but only because I didn’t know any better. This isn’t a blueprint or a life plan I would recommend, but it is the way it worked out for me. If you seem to be on a strange path and yet headed for book editing, and that’s what you want to do, take heart! Your strange path isn’t necessarily wrong.

Phase One: Magazine Editing

In the early 2000s, I was hired to do data entry at a car magazine. It was a lot of logging new subscriptions and sending files to the printer for mailing. But somehow, I ended up doing some proofreading for the magazine.

I knew grammar and spelling; I could fix things. It was a small enough magazine in page count, staff, and circulation that this seemed fine to everyone. We did have a professional freelance proofreader who marked up the printed pages by hand every month. Bill would bring them into the office, and I often ended up entering his changes. I learned a ton from Bill, and I googled the proofreader’s marks he used to learn what he wanted me to do. Then I started using those marks too.

I got pretty good at proofreading, so I moved up to copy editing. It was easy to move up; entire departments at that magazine had one person in them. I became the copy editing department when the previous copy editor left to to travel the world on the cheap with his wife for a year. He gave me as much training as he could, and then I swam in the deep end for a while.

I became a pretty good copy editor, and I had shown a love of filling in to-do items and checking them off on the big shared whiteboard where we tracked the status of the magazine’s content each month. Those skills meant I became the managing editor. I worked much more directly with the writers to improve their work, and I still copy edited a lot of those pieces. And I wrote quite a bit for the magazine too.

Phase Two: The Word Mines

When I left the magazine in 2006, I planned on being a freelance writer with a little editing on the side. So I took as many writing gigs as I could, and I eventually signed on with a business that provided editing services for early-days indie authors.

Some of the books I worked on were brilliant and probably should have been shopped to agents and traditionally published. Some were total trash that should not have been printed at all. Some needed the lightest of touches to polish them to sparkling, and some needed heavy-handed sandpaper to make them readable. My rate was the same either way, and it was non-negotiable. It was also not very high.

I never got to interact with the authors, which was odd. The editors’ names in Word had to be set to the level of edit they were working on, so Line Editor or Proofreader would show in the comments. I did get feedback from the company, which did improve my editing acumen. I also worked on dozens upon dozens of books with quick turnaround times. It was a slog and an education. And I burned out.

Phase Three: Indigo

Luckily, around the time that I knew I could not go on with these editorial mills, I picked up some of Indigo Editing’s overflow work. After a few projects, owner Ali asked me to join the team. I also take clients privately; however it works out best is fine with me.

In any case, I now get to work closely with authors (if they want to), and I get to pick which books I work on. I specialize in historical fiction, works in translation, and nonfiction because I like to look up details and fact check things. I have learned over the years that I like developmental editing and line editing best, though I can proofread if I need to. I still remember the proofreader’s marks Bill used in 2004.

The Next Phase

It only took me about 15 years to realize that I am good at editing and I really love it. During these years, I also wrote about cars for the New York Times, PopSci, How Stuff Works, TechCrunch, and a bunch of other places. I got to drive Ferraris and Rolls-Royces and a preproduction Spyker in Arizona. But I liked the book editing best. Even better than the Aston Martin.

I do still write about cars. You can find my work regularly at U.S. News & World Reports. I also still write about weird non-car stuff for How Stuff Works. (It’s worth noting that I have great editors at both of those places.)

But book editing is what I love the most. My brain is worn out at the end of the day, and my copy of The Chicago Manual of Style is full of sticky notes and coffee stains. I always learn more about my editorial craft from the books I edit, the books I read for fun, my fellow editors, and the occasional online class to keep things fresh.

So yeah, it was a crooked path. But it got me to the right place: in a studio in my back yard with a manuscript open on my screen and an open style guide to my left.

Obvious Freelance Lesson: Honesty Is the Best Policy

I’ve been freelance writing and editing since 2006, and it’s gone pretty well. I’ve had lots of happy clients, one unhappy one, and a reasonably steady income from an ever-evolving roster of publications. I’m pretty good at the whole freelancing thing.

But every once in a while, I need to have a basic lesson pounded into my brain for the second, or third, or hundredth time. Last week, it was a life lesson as well as a freelance lesson: honesty is the best policy.

I have a client that I’m writing blog posts for. The topic is new to me, and they’re new to hiring people to write blog posts, so we figured we’d work it out as we went along. There was a lengthy onboarding process, which is fine, and then we set out a schedule for me to turn in the posts.

The problem was that my default writing style and assumptions for the project were a hair off from what the client wanted. So I took their feedback and tried again. And again. This was not the only thing on either of our plates, so getting that first post right took weeks of back and forth via email and phone. I had other book projects due during that time, and I attended a conference for a week. When I took the gig, I thought we’d have the kinks worked out by that point and I’d be able to squeeze in writing the posts on cross-country flights. Not so.

I had the latest round of suggestions and changes from my client sitting in my inbox on my last cross-country flight. I had a weeks-long vacation looming. I had other deadlines. I started to think of excuses (fine, they were straight-up lies), like, “Sorry, your emails keep ending up in my trash folder.” Or the more modern, “Your messages got sorted into Promotions.”

The client didn’t deserve lies. They were being very nice; they just didn’t know how to articulate what they wanted their blog posts to convey, and I wasn’t asking the right questions to get us to perfect. So I told the truth. I made the latest revisions they requested and sent a note saying the blog post project had clashed with some previously scheduled deadlines and travel, and I had a vacation coming up.

The world did not end. A pit did not open up under my backyard office and swallow me and my dog. I did not have to pack up my freelance business, put on a suit, and head to a cubicle somewhere.

My contact said they had a vacation coming up too. They said to invoice them for the first blog post. They said we’d get back at it with more clarity and direction for next three posts when we’d both returned to our offices next month.

The outcome was, in truth, ideal. I really do think the client and I will both have a better handle on what’s required to make these blog posts work after some time away.

So the lesson, fellow freelancers, is that sometimes being the professional that you are means being honest—but polite—about what isn’t working.

How I Improved My Productivity in Two Easy Steps

You may think that headline is clickbait-y, but I did indeed improve my productivity this week in two easy steps. One of the steps was free, and one was not. The free one, actually, was harder. Here they are, in numbered list form so you can follow along:

  1. I got a robot vacuum. Believe me when I tell you that I do not spend an hour every day vacuuming or sweeping my house. But writers, hear me out. You know how clean your kitchen is when you have a deadline? Or how much laundry gets done when you don’t know how to start the next article or story? Or how the floors sparkle when your other choice of activity is revision? Well. This little guy (an EcoVacs N79, if you’re wondering) runs every morning while I work and removes a chore from my list of procrastination tools. The side effect is a floor that is free of cat and dog hair, even in spring, also known as shedding season. I come in at lunchtime with a writing task complete and no fur sticking to my bare feet. It’s delightful.
  2. I deleted Two Dots. You probably have your own game like Two Dots on your phone; if it’s not Two Dots in particular, I bet it’s 2048. I deleted that one too. I was really good at Two Dots. I had completed hundreds of levels. But I was neither writing what I wanted nor reading what I wanted, so it had to go.

What have I completed this week? I turned in an article on a hair-band mystery and a roundup of auto financing deals for the month of June, and I completed a very long outline for a 10,000-word article due in a couple of weeks. I also finished a line edit of another author’s book and sent it to the proofreader then wrote this little blog post for y’all.

These are all tasks I’d have to do for my job anyway. But getting rid of two big procrastination tools meant I did these things with less foot-dragging, sighing, and generally fucking around. I just did what I needed to do, and then I read the London Review of Books. Which I am behind on. Because of Two Dots.

To see my cats encountering the robot vacuum for the first time, check out my Instagram @kristen_hg. (The video was too big to embed here. Sorry.)

The Research Rabbit Hole

Running down the research rabbit hole is one of my favorite activities. I know other people hate it; that’s why they pay me to do it. And I am so happy to do it.

If you are not happy down in the hole with the information bunnies but you find yourself having to throw yourself into it anyway for your project, I shared four of the research tools I use just about every day in the Indigo newsletter this month. These will help you find what you need while you’re searching and keep track of what you find so you can actually use it later.

Good luck with your project! And wave if you see me when you land at the bottom of the research rabbit hole. I kind of live down here.

To All the Writers Whose Books I Edit: I Feel You

I write lots. For a living. And editors often return my articles with red lines all over the place and blue notes in the comments and green highlighting for all the words I overuse. Being edited is nothing new to me.


I was walking the dog the other afternoon, and it hit me mid-stride: Ali has started editing my book. Another person may be reading my manuscript right now, with a friendly but critical eye. She is making notes on my book, pointing out my errors and typos, and questioning the opinions I espouse. She is editing my book, which took me a year to write while writing a dozen other articles.

It was a weird feeling. Usually, when I hand over an article to an editor, I’m eager to get to the editing process. Hurry up and read it, I think. I want to check this box and move on to the next thing. The next thing in the case of Take the Wheel, though, is publication. Marketing. Reaching sales goals. I’ve never done these next things, and they are terrifying. All right, they’re not Somali-pirates-just-boarded-my-yacht terrifying, but still. And having Ali edit the book is just the beginning.

Happily, I am an editor myself, and I just returned a big batch of suggestions and comments to one of my authors. He thanked me, and we set up an appointment to talk about his next steps in the process, which right now are focused on major revisions to a solid memoir. He’s got a lot of work ahead of him, and he knows it. Here’s how he signed off his email to me:

Here we go.  Deep breath.  Step off.

Essay in the Indigo Newsletter

Now that I’m part of Team Indigo, I get to write for their newsletter (much to the relief of my fellow editors, who are glad to have another writer in the rotation). For the December issue, I was asked to write about community, a subject that, as a freelance writer who is happiest with furry, four-footed coworkers, I felt completely unqualified to tell other people about.

But, as it turned out, I had 500 words to say about community. It helped that I had a recent Indigo retreat and an upcoming holiday party to draw on, but I also realized as I wrote that community is important even for those of us who generally prefer to wear hoodies and hide behind screens. As it says in the essay, “sometimes you and your work have to see the light of day if either of you are to survive.”


I’m an Indigo Girl

It is now official. Last night, co-owners Ali McCart and Kristin Thiel plied me with two whiskey and ginger beers to get me to sign the Indigo Editing contractor agreement. (I would have done it without the drinks, but I never look a drink horse in the mouth.)

This means that if you’ve got a non-fiction book that needs editing at any level — and that includes memoir, how-to, self-help, spiritual, and creative non-fiction — I’ll be happy to work on it through Indigo. The upside for everyone is having an established editing firm with a stellar reputation involved to make the process smooth and professional. There’s even an office in downtown Portland! We can put on fancy office clothes and have author-editor meetings, like adults!

My contract with Indigo is definitely not exclusive, and they made very clear that they do not expect to put a lock on my time or my projects or my freelancing heart. I’ll still work on other book projects and write articles and blog posts and far too many tweets. I’m still working on automotive topics and keeping a hand in at the New York Times. This is just another basket to put my freelancing eggs in. A lovely indigo-colored basket.

If you want to contact me via Indigo, you certainly can:

khallgeisler [at] indigoediting [dot] com


Visit Me at Wordstock This Weekend

I am joining forces with Indigo Editing, and my first official act as associate editor is to work the Indigo booth at Wordstock, October 13 and 14. I’ll be in booth #812 Saturday from 1-4 and Sunday 4-close.

On Saturday, from 3-4, I’ll be doing free 15-minute consults for anyone who wants to talk about their non-fiction book project, from memoir to how-to. It’s all good. Or, if it’s not good, I’ll tell you how to make it better, as much as I can in 15 minutes.

I’m still freelancing at home and writing books, but working with Indigo gives me something I haven’t had in years: coworkers! They’ll even give me a desk in the office downtown! Not that I’ll got there very often, but it’s nice to know it’s there. I’m a happy solo worker most of the time, but once in a while I really nail an outfit and I want to make sure someone sees it besides the dog.