Home Work Retired

Home Work

A weekly advice podcast for people who work from home, whether freelancer or telecommuter. We address listener-submitted questions, comments and concerns about all aspects of working from home. Hosted by Dave Caolo. You can submit your questions here.

Hosted by Dave Caolo.

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200: Season 2: Episode 7 (#200!) - Writing with Brett Kelly

March 14, 2016 at 7:00AM • 51 minutes • Wiki Entry

On this bicentennial episode of Home Work (seriously, 200 episodes!) Dave and Aaron welcome Brett Kelly onto the show. Brett writes a lot, and manages a ton of email, and does it all for himself, from home. Which makes him the perfect guest to celebrate our 200th episode.

This week's episode was sponsored by FreshBooks. To get FreshBooks free for 30 days, go to FreshBooks.com/homework and enter 'Home Work' in the “How did you hear about us?" section.

This week's episode is also sponsored by Squarespace. Be sure to use offer code HOMEWORK to get 10% off your subscription!

Lastly, this episode was made possible by Wealthfront, making smart investment management available to everyone. 5by5 visitors get their first $15,000 managed free. Be sure to visit that link today!

Show Notes & Links Presented by CacheFly

Episode 200! After four years, and an average of 50 episodes per year, we've lapped the century mark. To celebrate, we're joined by Mr. Brett Kelly, writer, home worker and author of Evernote Essentials. Brett recently published a post on his blog entitled "How I Write," which inspired this episode.

Not a writer by profession? Don't worry, this episode is still for you. Here are highlights of what you'll hear, as well as the time codes at which you'll find each discussion.

Show highlights

5'08": Brett answers the question, "When did you start working from home?" Answer: May of 2010 when Brett took the job with Evernote.

6'06": Brett answers, "What is it you do when you work from home." Answer, "I pretty much write books, emails and lots of different things."

12'09": "The pleasure of seeing the guts of how other people work." Whenever there's a chance to see how a person whom you admire works, or a person how does what you do at a level you hope to achieve, that's almost irresistible." How does this person work that's different from how I do things? What nugget can I glean from seeing their processes? Is there a way to trim off a rough edge?

The irresistible "Is there a system out there that does what I do better or more efficiently?"

15'00": The point of diminishing returns in your "productivity addiction." "If you're constantly vigilant about your work and how you're getting it done, eventually you're not going to get any work done."

Mentioned app: Ulysses for Mac and iOS

20'34": Regarding productivity addiction: "You're not going to upgrade the software on the space shuttle while you're flying into space."

Mentioned app: Levelator

22'19": The five categories of things Brett writes:

  1. Shorter articles: blog posts, newsletter articles, and so forth
  2. Books or other long-form pieces
  3. Promotional materials like emails and sales copy
  4. Outlines and other planning-like stuff for all of the above
  5. Miscellany including social media updates, emails, and other odds and ends

24'28": Using older, proven techniques. Dave sheepishly admits that he writes outlines for articles, etc. using the method he learned in 6th grade. Brett says not to be ashamed about that. "As long as the thing you're outlining gets written -- as long as the work gets done -- screw how it got there." Is there a better way to outline? If what you're doing is working, then no there isn't.

Mentioned app: Typed

29'17": Brett loves MailMate and tells us why. Spoiler: Markdown support is a big part of that.

40'50": The appeal of simple systems with few moving parts. "Over the years, my processes and tools have gotten slimmer and fewer in number. I like simple systems with as few moving parts as possible. Writing this way satisfies my three main requirements:

  1. Write anywhere on whichever device I happen to have with me.
  2. Have my work synced off of said device instantly (either as I type or upon saving).
  3. Format portability; no matter what format the finished product must be, I can get there starting with Markdown.

Mentioned app: Drafts