Hyper-Scheduling Feedback 

I’ve had a lot of feedback about my prior posts about the hyper-scheduling experiment and implementation details. Here are the prior links:

The Hyper-Scheduling Experiment

Hyper-Scheduling Mechanics

This whole thing has turned into a short series here at MacSparky.com. There may be another post or two about this, but today I’d like to share some of the feedback. I’ve received a surprising amount of email/tweets/feedback on these posts. They fall into several categories:

Hyper-Scheduling is Insane

I recently spoke at the ABA Techshow, and at some point an old lawyer-nerd friend cornered me. “David, are you really doing all that crazy stuff with your schedule?” (That quote is nearly perfect. He didn’t use the word “stuff”.)

This sentiment boils down to a lot of people who have never tried something like this marvelling at what an extraordinary investment of time hyper-scheduling appears to be.

I agree putting something like this in place takes time, particularly when getting the habit started. However, having been doing it now for awhile, the time investment is not nearly high as someone who has never tried it would think. I schedule each day and the end of the day prior. Using the mechanics I explained in the last post, most of the scheduling is simply selecting prior instances in the calendar week view, duplicating the item, and then moving it into place. For me, most days start with some Field Guide Work for two or three hours and most days end with shutting things down and planning the next day and in between comes a whole lot of legal work and podcasting that varies on a daily basis.

A key competent of all of this is having a task management system that can help you keep track of all of your tasks (so you don’t have to) and unearth those priority tasks out of the database on a daily basis. I’m pretty adept at OmniFocus so it usually doesn’t take me long to find those tasks that will get checked off the day before and assign appropriate time blocks to get the job done.

For me, the trickiest part about setting it up is being realistic about how much can be accomplished in the next day and not biting off more than I can chew. The practice of hyper-scheduling however, has provided an excellent tool for me to get better at that skill. At this point, hyper-scheduling takes me about 20 minutes. As explained throughout this series of posts, a 20-minute daily investment for all of these benefits is a no-brainer.

Hyper-Scheduling is Unrealistic

No plan survives contact with the enemy.

–Helmuth von Moltke

This second category of criticism boils down to the above quote. It doesn’t matter how much time you spend scheduling if you walk into the office to find it on fire. I’d generally agree with that criticism. Several times since I’ve started hyper-scheduling, I’ve had days where a true client or family emergency appeared requiring me to sweep aside my carefully laid plans and spend the day manning the fire hose.

I guess the real question for these critics is exactly how often do they find that the office is actually on fire. If that’s a routine thing, I think that is more of a problem with the office than hyper-scheduling. The lawyer equivalent of a fireman is a litigation attorney. I was in that racket for 20 years and can tell you at the time I experienced a lot more fires than I do these days. If you have a job that requires you to put out fires on a daily basis (and you’re okay with that), I don’t think hyper-scheduling is for you.

Conversely, however, I’d ask you to make sure the there truly is a fire. As my law practice has transitioned to a transaction-heavy practice and away from the sausage factory that is modern litigation, before hyper-scheduling I was acting like there were daily wild fires where, in hindsight, there were very few. Too often I’d let the smallest problems derail me. Hyper-scheduling has given me more perspective so that a lot of things that I was earlier treating as four-alarm fires now just gets blocked into some time in the next few days and I’m able to stick with the original plan.

Hyper-Scheduling is Nothing More than Sophisticated Procrastination

One reader wrote me and opined that my hyper-scheduling seemed like re-arranging the deck chairs on the Titanic. The argument is that Hyper-scheduling is a way to fiddle, instead of doing work. I think this could be true if you were too precious with your scheduling. The minimum block of time for me to deal with a specific problem is usually no less than an hour. I don’t Hyper-Schedule by making a dozen 15-minute project blocks that I then carefully arrange like a jigsaw puzzle. That would be a waste of time. All of the little, important things I do every day get OmniFocus flags and lumped together in the “Capture Flags” block. I agree someone could implement hyper-scheduling in a way that gets too fiddly. However, I think someone that gives it the smallest amount of thought and deliberation could avoid that trap.

Hyper-Scheduling Doesn’t Actually Give You any Additional Time

Yup.

This was my own biggest source of resistance to the experiment in the first place. Scheduling myself for ten hours a day does not magically give me 20 hours of work. It’s still just 10 hours. While that is true, adding the planning and deliberation to the day has allowed me to get a lot closer to 10 hours of work done in a 10 hour day where before I was getting more like five or six hours of work done in a 10 hour day because I spent so much time blowing in the wind.

For me, Hyper-Scheduling adds a sense of purpose to the day and lets me be much more deliberate with my time and the projects I spend my time on. Either way, while it’s true this technique doesn’t magically give you additional time, it lets you use the time you do spend on important work much more efficiently.

Hyper-Scheduling is Nothing New

These are my favorite emails. I’ve received lots of affirmation from readers that have been doing this in some form or another for years and ask me, in one way or another, “What took you so long?” Some folks call it block scheduling, others call it fancier things like value-based time management. I’m certainly not the first guy to this party, and I find that comforting.

Script Debugger 7

If you spend any time writing AppleScripts, you’re going to want Script Debugger. Script Debugger is the development tools the real power AppleScript users employ and it’s now up to version 7. It has a pile of tools not available in the native Script editor including a much better dictionary, better debugging, code completion, split pane editing, customization and more. 

I know AppleScript is a fairly niche thing these days but if you want to get better at it, this is the tool for you.

Hoban Cards – Sponsor

I’m so pleased to have Hoban Cards back as a sponsor. Hoban Press and Hoban Cards make beautiful letterpress business cards and stationery using their 1902 massive letterpress machine. I use Hoban Press business cards and love the envious look I get from other lawyers when I share them as they hand me back their mass-produced, soulless cards. There is a long history of calling cards and the gang at Hoban Press wrote an informative article explaining it. Did you know that Egyptians had the first calling cards and they were made of clay?

Hoban Cards has some beautiful, typographic designs you can choose from. Hoban Cards doesn’t just operate the heavy machinery, the owner is a graphic designer and can help you make your own custom business card if that’s your thing.

For years I’ve been buying stationery and cards from the Hoban team, and their customer service has been excellent. They’re currently running a monthly contest to win $100 in Hoban Cards. So head over to Hoban Cards and make sure to use the promo code “MacSparky” to get $10 off any order. 

MAC POWER USERS 421: Business Workflows


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In this episode, we share our favorite business workflows including managing email, calendaring, TextExpander tips, reducing paper, managing PDFs, billing, communicating and more.

This episode of Mac Power Users is sponsored by:

  • Squarespace: Make your next move. Enter offer code MPU at checkout to get 10% off your first purchase.
  • 1Password: Have you ever forgotten a password? Now you don’t have to worry about that anymore. Save up to 20% using this link.
  • The Omni Group: We’re passionate about productivity for Mac, iPhone, and iPad. 
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On Focus

Last year I noticed my priorities were out of whack and I spent several months woodshedding the latest productivity books and websites as I sorted myself out. One prevalent theme throughout the productivity world as of late is how to keep yourself focused. Keeping yourself on target is an important skill. Cal Newport wrote a good book about it and Shawn Blanc developed an entire online course around it. 

Luckily, this is one of the few things I’m good at. I’m not sure if I’m a focus savant or it’s just a side benefit of having a regular meditation practice for over 25 years but I’m good at locking in on one thing to the exclusion of the rest of the world. There are actually some pretty funny stories about me growing up and being completely oblivious to the world around me as I read a book or was dialed in on something else. 

Regardless, people are having a lot of trouble keeping their attention on a single task with all of these digital devices surrounding us. There is a whole cottage industry of apps that can do things like dim sections of your screen, hide your social media apps, and even turn off your internet connection requiring heroic efforts to get it back up and running all in effort to avoid distractions. My daughter routinely deletes social media apps entirely from her phone when she is working on a deadline. 

A lot of people are going to some extreme measures in the name of focus and I’m not sure that is necessary or, in the long term, sustainable. It’s like trying to lose weight by not eating. It may work for a day or two but after that, it’s all downhill. Getting better at focus is difficult and it takes time to master. Here’s my list of suggestions for some help along the way. 

Set Your Non-Essential Technology Aside

If you’re working on your Mac or iPad, just put your phone down with the glass on the table. When you get tempted to pick it up, you’ll see it is face down and remind yourself how much more fun Alto’s Odyssey will be after you finish your sales report/spreadsheet/term paper/whatever. Alternatively, put you tech in another room.

Banish Notifications

Nearly everyone, myself included, has let notification bloat creep into their lives. The first time you launch just about any new app, it asks for permission to tap you on the shoulder at will and you, in a fit of optimism, will think to yourself that “This garbage truck simulator app is the one. This is the app that will change my life and of course it should get notification privileges”. You’ll tap the button and then put up with needless notifications from that app forever. I made a video about notifications that show you how to fix that. 

I suggest a notification purge. Why not try turning off all notifications on your phone? It’s not that hard (although I wish Apple would make it easier). Just turn off all notifications and live like that for a day or two and then only add back notifications for the apps from which you absolutely must get notifications. This clean slate approach is exactly the way I reduced the number of daily notifications from about 40 to about 5.

Use Calendars and Timers

The whole hyper-scheduling thing I’ve been writing about is in part my own effort to keep focused on the important stuff. In my case, it is more about the areas of focus than the ability to focus but it’s a similar problem. Blocking time on your calendar or setting a timer is a great way to focus in bite-sized increments. It’s the entire idea behind the Pomodoro Technique. I do think giving yourself a timed focus period is a good way into tricking your brain into getting better at this. Telling yourself to just focus for X minutes makes the lure of all those shiny technology interruptions bearable. Start with as short of an interval you need to succeed and then start moving it up slowly.

The “Not Now” Folder

Make a folder on your iPhone called “Not Now”. Put apps in there that are your frequent temptations. For some people, it will be Facebook. For others, it may be Twitter or even Email. Make opening the “Not Now” a deliberate act that you do only when you are not focused in on getting some work done. If you really want to go nuts, put the “Not Now” folder on page three of your home screen to really keep it out of mind.

Consider Trying a Little Meditation

It’s really not hippie nonsense. A mindfulness meditation practice is not a religion. It’s just a way to help you tame that wild organ between your ears and anyone can do it. You can learn more with an app, like Headspace or through a good podcast. It’s a great way to work on your focus muscles. And speaking of focus muscles …

Think About Developing your Focus like Developing Muscles

It does take practice and time. Even if you take a pass on meditation, try to focus on what you are doing other times during the day. It’s easy to do that while you are mountain climbing or surfing but what about when you are driving, or eating an apple? Can you keep your brain on target then? You need to wear new grooves into your brain and that doesn’t happen overnight.

Don’t Be So Hard on Yourself

There are so many articles on the Internet by people dealing with the focus problem that are beating themselves up about it. That just gets in the way. We have more distractions thrown at us these days than any time before in human history. We’ve all got to come to grips with it and it’s hard. Don’t be so hard on yourself. If you occasionally fall off the wagon, don’t get angry. Just get back on the wagon and keep trying.

Free Agents 42 — Learning Your Creative Rhythms, with Shawn Blanc


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In this episode, we go through the Free Agents mailbag with observations about the legend of the man who outsourced his own job, taking a hobby to the next level, and the menace of imposter syndrome. Then we welcome our guest, Shawn Blanc, creator of The Sweet Setup and shawnblanc.net, to discuss building an independent business with collaborators, solid project planning, and sensible work hours.

This episode of Free Agents is sponsored by:

  • Squarespace: Make your next move. Enter offer code FREEAGENTS at checkout to get 10% off your first purchase.
  • Casper: The Internet’s favourite mattress. Get $50 off select mattresses with the code ‘FREEAGENTS’.
  • Freshbooks: Online invoicing made easy.

Task Management Pain Points – Orphans

One area of trouble for anyone with a lot of projects is orphans. Those are those projects or tasks that somehow fall off the radar and fall apart not because you are actively ignoring them or prioritizing them as “on hold” but instead because you forget about them. An orphan may be unimportant but it may also be mission critical. Ignore them at your peril.

If you follow GTD, you should not have many orphans because the system requires you to review all your projects on a weekly basis. While I use elements of GTD in my planning, I don’t adopt the system entirely and I don’t review all my projects weekly. Instead, I use the OmniFocus review feature to set custom review times depending on a project’s priority. If I’m working with a client on a big contract, I’ll get a review reminder every week. If I’m just maintaining a corporate book for a client, I’ll only get a review reminder every six months. Although my longer delayed project reviews could cause me a problem, I’m pretty good about starting new projects for anything that requires a more frequent review frequency. Another thing I do while reviewing projects in OmniFocus is assessing the project’s current review frequency and consider whether it needs adjusting.

OmniFocus is the only task app I’m aware of that includes a review mechanism but you could put something similar together yourself in other apps. Just add a task inside projects called something like “Review Status” and set it to repeat at some reasonable frequency.

There also isn’t anything wrong with just taking a few hours every month or two and doing a top-to-bottom audit of your task system. This even works for the paper and pencil crowd. Every time I do one of those audits, I feel better afterward. Moreover, during audits I sometimes do find an orphan lurking in my system and, even better, a few projects I can kill. 

iOS 12 Concepts

Last week, 9to5Mac Linked the iOS 12 concepts from Behance.net. While I’m not usually very interested in these alternate reality concepts, I do like a few of their ideas.

Nameless Apps

They mocked up a home screen with no app names, and it looked so much better than a home screen with app names. When is the last time you actually read the name of an app on your home screen? I honestly can’t remember ever doing so.



Information Dense Lock Screen

I also like their mock-up of a lock screen that lets you pull down for weather, although I’d let the user decide which today view information a pull-down gets you. (I’d probably use it for OmniFocus or Fantastical.) Of course, there would be security concerns, but it could be user choice like other lock screen information.



June and WWDC (the Apple Worldwide Developers Conference) isn’t far away, but I wouldn’t hold my breath for Apple doing either of these things.

Solve your Email Problems with SaneBox – Sponsor

This week’s sponsor, SaneBox is the solution to so many of my email problems. SaneBox is the email service that adds a pile of productivity features to your email, regardless of what email client you use. For a lot of folks, email is a constant pain point, and it doesn’t need to be. With SaneBox at your back, you can:

  • Wake up every day to find the SaneBox robots have automatically sorted your incoming email for you so you can address the important and ignore the irrelevant. 
  • Defer email for hours, days, or weeks, so it is out of your life until a more appropriate time. They’ve even added a new feature that can optionally auto-reply to snoozed email with something like, “I’m sorry, but I’m underwater right now. I’ll get back to you in a few days.”
  • Set secret reminders so if someone doesn’t reply to an important email SaneBox gives you a nudge to follow up.
  • Automatically save attachments to the cloud (like Dropbox).
  • Use their SaneForward service to automatically send appropriate emails to services like Evernote, Expensify, and Kayak.
  • Move unwanted email to the SaneBlackHole and never see anything from that person again.

The list goes on, and MacSparky readers love this service. I was just speaking with the folks at SaneBox, and they report that 70% of the MacSparky readers that try SaneBox end up signing up for it. That’s crazy but not surprising to me because SaneBox works. Why not straighten out your email by getting a SaneBox account and bringing a gun to a knife fight. If you sign up with this link, you even get a discount on your subscription. 

Mac Power Users 420: Presentation Workflows

Presentations are on our mind on this week’s episode as we prepare for talks at ABA (American Bar Association) TECHSHOW. We discuss workflows for planning a presentation, tips for making your slides, getting ready for the big day, dealing with nerves, and making sure your presentation goes off without a hitch.

This episode of Mac Power Users is sponsored by:

  • Casper: The internet’s favorite mattress. Get $50 off select mattresses with the code ‘MPU’.
  • Timing: The automatic time-tracking app for macOS. Use this link to save 10% on your purchase.
  • TextExpander from Smile: Type more with less effort! Expand short abbreviations into longer bits of text, even fill-ins, with TextExpander from Smile.
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