What we learned self-publishing our first book.

I can’t believe it, but our first book is finally on the shelves! After 4 months of writing, editing, formatting, printing, proofing and re-doing all those things a hundred times, I thought I’d share some behind the scenes thoughts on what it’s like publishing a book on your own.

A few weeks ago it was 14 degrees in Chicago, and I had to trudge my way to Target. It was the day before we were set to package up 100 or so pre-orders of our  book and ship them off with t-shirts, pens, and stickers, and I’d had last minute thought that we should include some candy. Partly because everyone loves candy, and partly because candy makes everyone love you.

As I walked through the parking lot, my arm started feeling the weight of the heavy bag, and before I could stop it the flimsy plastic bag ripped its handles and crashed from my grip, sending 450 pieces of assorted candy flying across the icy ground and under the tires of a nearby passing car.

I stood there wind-whipped and defeated, thinking, “There is no greater analogy to what publishing this book has been like than this very moment.”

So here’s the deal: This book is great, we worked hard on it, people liked it and it matters to them. What else could you ask for in life than to do something that matters to someone else, and help their lives improve in some very small way? I am so, so proud of the work that went into this book from the CoSupport team and our amazingly generous contributors Laura, Rich, Shervin, Jeff, Jason, and Spencer.

But here’s what went wrong in publishing our first book, in no particular order.

Problem #1. We had too much content. When I say this, I think about that Onion article from a few years back with the headline “What am I going to do with all this spare change!?” Having too much good content isn’t necessarily a bad thing, but it poses huge challenges when you’re trying to curate a cohesive theme for your project. We ended up having to cut almost 120 pages of essays and while we can now look forward to another edition of the book, it really messed with our timeline, our editing process, and our confidence. What if we cut the wrong essay? What if that one doesn’t make sense without that one? What if this is all a mistake!!

Solution: We should have had a better outline going into the book of what we needed to accomplish, and allowed the content to determine its own theme, or lack thereof.

Problem #2. We didn’t go with a publisher. Listen – it’s the future. No one needs a publisher anymore. But they are very nice to have because they can help with things like production and distribution, and production, and getting your book produced. This posed the biggest challenge for us because printing in small quantities is very expensive, and we had a vision to have 5×8 books printed and coil bound. Coil binding would give life to the concept of a handbook – we envisioned an old time car manual that you could flip through and fold over and fill up with sidebar notes.

The first attempt at printing the books was an epic failure. The covers were so thin and fragile they ripped and frayed if you looked at them funny. We chose to push the release date, notified all our customers, and everyone was incredibly gracious and understanding. For the second round of printing, we ordered a proof to start and this time, the metal coil binding wasn’t fully enclosed around the book. That meant every time you’d turn a page, it would fall out. I’m sure this happens to James Patterson all the time.

On the third attempt, I decided to just wing it and I ordered 100 copies of the book without getting a proof, because at this point people had waited 4 weeks past when we promised they’d have their books. I took a swing at a fast pitch and ARE YOU KIDDING ME, this time the colors on the cover of the books did not print well. At all. At all at all at all. We had no choice but to send out the books with bad cover printing and that is why maybe, at some point in life, publishers aren’t so bad after all.

Solution: Don’t announce you’re publishing a book until you have the very final proof printed and in your hand.

Problem #3: We chose to distribute deluxe copies on our own. This isn’t really a problem, really, but it is a hassle. CoSupport is a 100% distributed team so that means we don’t have extra hands in the same city to help package 100 books, t-shirts, and candy. If you do choose to handle distribution on your own, even for a limited release or a small batch, GET HELP.

I was very lucky to have the time to handle this on my own, and since we have collaborative office space at Workshop Chicago, I was always around other people when I was packing up books and shipping them out. Having some camaraderie and support when you’re doing a totally tedious and repetitive action for days on end really makes it suck less. I can’t thank our pal Ben Skoda enough for his constant encouragement and humor while he watched me work through the tedium at our office, and for always keeping a stock of baked goods around.

Solution: Hire an intern. Pay people in pizza! Just get help, because even for the most organized checklist OCD process person in the world (me), it’s still really confusing and difficult to keep track of everything.

Problem #4: People really, really wanted this book. Like, really.
Again: not really a problem! But when you’re working hard on a project and trying to get it in people’s hands, the demands for it can be a bit overwhelming. When we knew that production issues were going to push the print and release dates out, I had an awesome anxiety meltdown. Luckily, only one asshole person was an asshole about the delay, and everyone else was incredibly kind, excited, and patient with us (Except that one asshole guy).

Solution: Be honest if there’s issues holding up production. People are ok if you’re honest and upfront. The secondary solution would also be: Don’t announce the book until you’re pretty sure nothing’s going to delay it. And don’t freak out if people really, really like you.

One more thing: If you’re going to ship out deluxe copies on your own, CHARGE MORE FOR INTERNATIONAL SHIPPING. It costs $23.05USD to send anything in a 9″x12″ envelope anywhere outside of the USA. We had 19 international orders. We now have “suckers” stamped on our foreheads.

Here’s the tools we used to publish this book:

Writer for Mac. The best writers tool, hands down. Turn on focus to highlight only the paragraph you’re working on, and make sure to check the lower right corner for the estimated reading time!

Sweating Commas, our editor. I’ve worked with Jason for almost 5 years now and he’s really the best for editing your online writing. We’re lucky he took on this crazy project and was so patient with me while I sent him bullet point lists that included sentences like, “Something else will go here.”

CreateSpace for publishing. I’ll be honest, it’s not the best out there. But it is the most simple way to get your book on Amazon, and their online proofer is stellar. It also scans for typos!

Bulleit Rye and Ginger Ale. One inch of each over ice.