The Writing Routine

If we’re writing about writing, it’s a great excuse to use this picture again. For the full context and backstory I think you’re just going to have to go back through the archives of my 40 Days To 40 Countdown.

If we’re writing about writing, it’s a great excuse to use this picture again. For the full context and backstory I think you’re just going to have to go back through the archives of my 40 Days To 40 Countdown.

(Sunday Paper, Volume III, Issue 44)

I haven’t spent much time in the past few years writing about the day-to-day of my writing.

Partly that’s because, up until now, there hadn’t been a day-to-day.

It was a little bit of work here, a little bit of work there.

But this is now my fifth year of freelance writing, and I’m finally figuring out how to do it.

When I was first starting out - this actually applies to both comedy and writing - I found great value in reading about other people’s experiences and following their leads to find my own footing.

So I hope this post kind of pays that forward and someone reads this and it helps them forge their own path if this is the road they end up on themselves.

Here’s a little look at how I work.


So I think the first thing I should mention is that in many ways I’m still figuring things out. I am by no means an expert in how best to pursue a freelance life…but I have a better grip on things than I did five years ago.

Back then my focus was on creativity - I wrote a middle grade novel (I think - I don’t know if it even qualifies as such) and sent it to agents and got a couple of rejections and lots of non responses. That project took up the grace period of not making any money. So then it was time to buckle down and find paying gigs.

I hoped I could make a career out of writing personal essays and those were one-offs that were fun to write but no one wants to pay for enough of those that I could support myself on.

But those essays, some of which were published on small sites on-line and some of which were in print publications, combined with some steady magazine writing (a travel publication that highlighted towns in New York and Illinois - I’d call Chambers of Commerce and summarize the travel highlights of said towns) to sustain me for a couple of years.

(I also scored a decent paycheck writing a round of sports trivia questions for a company that makes one of those pub trivia machines that cycles through the questions. It was fun - I was like, I can make a career out of this! That was my first paycheck, right out of the gate after I started searching for work after I finished the book…and I haven’t done anything like it since.)

The travel magazine and its parent company provided steady work for a while. I started doing special projects for them around the Super Bowl, the 75th anniversary of the bombing of Pearl Harbor, and the history of the presidency, among others, and then the past couple of years I settled into two even steadier jobs.

And that’s been the successful ingredient for me, really - whereas I thought freelancing would be doing a little bit for a lot of different places, it’s turned out to be more successful doing a lot for a few organizations.

I still think I would benefit from another one or two providers of steady work, but right now I’m working with a technology company writing primarily case studies and education blogs and working with a school to put out their weekly newsletter.

And that leads me to the regular routine:

I now spend Monday morning reading through a bunch of education publications gathering information on how certain pieces of technology are being used in higher education. It’s fascinating, and it’s what I know: you may or may not believe me when it comes from me, but I was a pretty good educator. And good teaching and good aspects of the education world are still things that excite me and I like that I get to read about what’s happening in that world.

Then I write a few blog posts a month about these things, and I do that on Monday or on Tuesday, when I also tackle case study work on how companies use the technology of the company I’m working with.

Then Wednesday through Friday I’m at the school (this is the second organization I work with) gathering all the different information from the different parts of the school to put together a newsletter that comes out most Fridays of the school year. (Not vacation weeks, so this is like a 30+ish-week-a-year deal.) Wednesday and Friday are kind of short days, I could do some other stuff on those days, but Thursday is pretty much a full day at the school. And, as I alluded to, it’s good for me being around a school a few days a week. I like the energy.

And then as you’ve surely picked up on in other posts, I’ll write on the weekends if I need to get some work done or if I have a quiet moment. (And that’s when the Sunday Paper gets either written or finished up.)

So that’s that. I am being intentionally vague in certain respects because the details of where I’m doing the work aren't important - it’s the routine and the fact that I’ve found steady work that are important.

And finding that work has been, to this point, a pretty even balance of having a door opened to me by someone I knew connected with the organization (something that’s lucky) and having had to apply to work by sending my resume and a cover letter (something that I’m not so great at but so far I’m two-for-two when I really spice up the cover letter so that it stands out). There’s also the “sending work or pitching an idea to an editor” which I do sometimes but I need to do more of and which certainly has resulted in way more nos than yeses. But that’s just the writing life.

And so far, five years in, that life is working out OK.


*Kathy was away most of this week. I forgot to mention that last week. So after I hung out at the Comedy Studio last Sunday night (which was the final post of Sunday Paper Live!), I was home with the kids the rest of the week. It was a great week, but that meant no comedy. This week I’ll be getting back on my feet in that department by going to some shows…and I’m performing at Improv Boston Saturday night - I’ll be doing some stand-up in the middle of a sketch show. I haven’t done that yet - I’m looking forward to it.

What I’ve Been Enjoying

*I didn't totally remove myself from comedy this week - Since I was home and alone after the kids went to bed at night I watched Adam Sandler’s new comedy special on Netflix, 100% Fresh. I had heard people talking about how silly it was and instantly flashed back to my teenage days when I would just listen to his comedy CDs and crack up. (And then make my brother and sister listen to The Goat…was that what it was called? I thought that was so funny.) So I figured I had to watch this.

I’m so glad I did. It’s super-raunchy, but it’s funny. (I say that in case I have young readers here and they think they should go watch it. I’d say parents beware.) The special is interestingly shot, interspersing all of these different performances together, but it just all seems like a vehicle to get to the touching ending, which I won’t dwell on here but the last 15 minutes or so are a real tear-jerker. It was a great way to spend an hour.


*John, this book you mentioned up there, do you care to tell us more about it? Nope.

*It’s just that I don’t know if it’s any good or not. I know it was a good experience to write something start to finish and maybe it’ll end up being worth sharing more widely some day but I have a feeling I have other books in me that will end up being better. I would love to try to get something else written in the new year.

*I believe I’ve told you that I’ve been writing a little bit every day in 2018 - if I haven’t: I’m doing a little bit of creative writing every day of the year. The plan, which has been a successful one, was to turn writing into a daily habit. I’m hoping to continue that in the new year in a more structured way, so that instead of 365 or whatever pages of separate random thoughts I’ll have a year’s worth of a more cohesive piece of writing.

*I can’t believe it’s November already and I especially can’t believe how close we are to Thanksgiving. This year is weird because Thanksgiving is the earliest it can be, and the kids don’t have a full week of school again until after Thanksgiving. (They have Election Day off this Tuesday, then the next Monday in honor of Veterans’ Day, and then the following week is Thanksgiving.) And then that next full week is all November, which is odd for the week after Thanksgiving…which means it’ll feel like a longer stretch, I guess, until Christmas.

*I’ll tell you what, though - these past two days have been classic fall blustery. And it’s leaf-raking time so I pretty much spend the days plotting which leaves I’ll pick up and when I’ll do it in order to have them ready to go for our Monday collection each of the next four weeks. I am somewhat insane.

*One last “life of a freelancer” tidbit: I’m waiting on a check. That sometimes happens - sometimes it comes two days after I submit the invoice, sometimes it comes a month later. It always comes, though, and I’m usually lucky enough to be in a situation where I don’t need the money immediately, so it’s not something I complain about. The fun thing is, though, when the checks back up and then a couple to a few of the payments come at once and I know what it feels like to be rich for a day. And then I pay whatever we inevitably have to pay and it’s back to regular old not-rich life.

*Did you turn your clock back? Great.

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