Project Status Board

I recently read Cal Newport’s A World Without Email: Reimagining Work in an Age of Communication Overload . One of the things Newport talks about in the book is finding alternatives to email for different kinds of work. He explained that as a college professor, he manages graduate students using a Trello-based Kanban board.

While it has nothing to do with email or collaboration, this got me thinking about how I’m managing my various projects when wearing my lawyer, podcaster, blogger, and field guide producer hats. Traditionally, I keep lists of active projects in a text file (currently in Obsidian). I tag all active projects in OmniFocus as an “Active Project” and then set a custom perspective to surface only active projects.

But I also know that I think visually, and the idea of a Kanban-style status board for my projects does have a certain appeal to me. So over the weekend I went down the rabbit hole of the current crop of Kanban-style apps. There is a lot out there. Trello, monday, and Notion all look like they’re up to the job. But in this case, I’m looking to make something that only I’ll be tracking. (I do my team-based stuff in Basecamp.) Because I don’t need it to collaborate, it doesn’t need to be a web service.

One of the Newport book stories was about the copper works at the Pullman railcar factory and how, in the early 20th century, they made what could be considered a big spreadsheet on the wall of the factory to track projects and labor. Again, because I don’t need to share this with anyone on the Internet, I considered doing something like this with a whiteboard in my studio, but I also wanted to figure out if my solution could show up on mobile devices and link to my projects. Also, I have this gigantic monitor, so I figured I could use all of that screen real estate. I experimented with Pages and Numbers but ultimately built my project status board using OmniGraffle.

OmniGraffle has a great set of alignment tools. I made a standard rounded rectangle box in which I can list the project’s name and, if there is a related OmniFocus project, I included a small OmniFocus icon. Using OmniGraffle’s linking tools (and some contextual-computing-style linking), I added a link directly to the related OmniFocus project on the OmniFocus icon. Then the full project rectangle gets a separate link to the project document in Obsidian. I can re-arrange the blocks as needed and, when done, I put the OmniGraffle document in preview mode (Option-Command-P). This blows the diagram up to full-screen size, and all of the embedded links are live so that I can jump from there to any specific project or OmniFocus document. On the macro level, I’ve also included links to the specific locations in Obsidian, OmniFocus, Basecamp, and Airtable, where appropriate. Here is the final product with a lot of confidential data blurred out. You can still get the idea.

So now I have three screens on my Mac. The left screen is Fantastical in full-screen mode showing the week view with 14 days. This is where I block time and plan future days. The center screen has no full-screen apps. Instead, it has all my windows from my working apps. (How I arrange that is a post for another day.) And the third screen, to the right, is my OmniGraffle generated project status board. I’m only a few days into using this status board, but I can already tell I’ll be keeping it. Another nice benefit of doing this in OmniGraffle and storing it in iCloud is that I’m equally able to view and edit the status board on iPhone and iPad with the mobile version of OmniGraffle.

The Never-Ending Inertia of Habits

I’ve been thinking a lot lately about habits. I think most of us have it wrong about habits. We think of habits as these little behaviors we intentionally build into our own selves when the need arises.

While we may think that habits are intentionally formed, habits are more often unintentionally formed. Things like getting french fries on the way home from the office, planting yourself in front of the TV for hours at a time, and hitting the snooze button are all habits unintentionally formed. The unintentional ones are the most insidious because they check all the habit boxes (cue, craving, response, reward) without the human being conscious of them arising.

Then one day, you wake up and realize you can’t stop eating french fries. You waste way too much of your time in front of the television. You can’t get out of bed in the morning. And you don’t know why.

Put simply, habits are always forming. The train never stops. Perhaps even more important than being intentional about forming new habits is being aware of all the habits you have already formed, many of which are self-destructive. I have tried to pull this intentionality to the front by making a list of all habits I’m observing in myself (some good, lots bad) and then trying to rewire myself where appropriate. This will take a while, but awareness is definitely the first step.

Leveraging COVID Constraints

I can’t help but feel things will be a lot more normal-leaning in the next six months as the COVID vaccines make their way into arms, and we, collectively, finally get the upper hand on this damn virus. Kids will go back to school. People will go back to work. We’ll be more social with one another. At least one can hope.

Assuming that is true, I’ve been taking stock lately of all the changes I’ve made to my life throughout the pandemic due to the constraints it brought. Once life gets back to life as normal, I don’t want to necessarily abandon all of the changes I made during lockdown. Maybe you shouldn’t either.

Several of the changes I’ve made to how I work have turned out to be substantial improvements over how I was getting things done pre-COVID. For example, having my kids and wife back home 24/7 means I had to be very particular about scheduling when I record podcasts, screencasts, and videos. This actually resulted in me getting more consistent recording work done than when I had free reign to do it whenever I wanted. I’m now making a list of the positive changes I’ve made during lockdown and figuring out how to keep those parts when things get more normal.

As far as tech, this is not rocket science. I’m just doing it in a text file. I’ve got the idea to build this list in the back of my mind and, as I go through the days and encounter changes I would like to keep, write them down. Ultimately, I’ll incorporate check-ins for myself to make sure I keep up with the new habits in the future via OmniFocus.

The Essential Weekly Review

Lately, the Focused podcast has been covering planning, goals, and roles. I think, overall, we don’t spend enough time checking in with ourselves. This is true on an emotional basis (which is why I think journaling and meditation are a great idea). It’s also true on a more strategic level, which I is why I do a weekly review every week.

As you go through your days, it is easy to get lost in the weeds with your task lists and calendars. You need to take a step back and make sure that the windmills you are tilting at actually relate to what gives your life meaning. It is so easy to get off track.

I like to think of weekly reviews as compass checks. If you’ve ever been hiking, you know how important it is to make sure you are actually going in the direction you intend. For that, you’ll need to check your compass. The more frequent you check that compass, the more likely you are not to stray.

So once a week I sit down and look at the roles in my life and how I’m doing. I write down a few words, but more importantly, I force myself to do that compass check and make sure I’m actually marching in the right direction.

I also do monthly and quarterly reviews, and maybe I’ll write about those another day. But one of the best ways to keep yourself on course is to adopt your own weekly review. Put simply, once a year (or twelve times a year) isn’t enough. Fifty-two times a year is much more helpful. Moreover, once, you get rolling with a weekly review process, you’ll find it doesn’t take an extraordinary amount of time. My weekly review takes about an hour. Think about all the dumb things you do in a week that take an hour and give one of those up. I guarantee you a weekly review will be worth it.

So here are a few tips if you are interested in trying it out for yourself:

Set an Appointment

Schedule the time, and treat it as you would an appointment with someone else. The weekly review is way more valuable than most meetings. By putting it on the calendar, you are dramatically improving your chances of actually doing it.
Have an Agenda

My weekly review starts with an audit of my roles (as discussed in this week’s Focused episode). How am I doing as a dad, a brother, a MacSparky, a healthy human? I take each role and look at how I’m doing and how I could improve. I also ask myself if I’m generally making progress on that role.

After that, I have some weekly prompts that I ask myself generally. It’s a long list, and I don’t answer every question every week, but instead use the list as a jumping off point when something strikes me. A few of the questions, to give you an idea, are as follows:

What was the best use of my time this week?
What was the worst use of my time?
What’s my biggest challenge right now, and what should I do about it?
What can delegate this week?
What frogs will I eat in the next week? (This is a reference to the Mark Twain quote, “If it’s your job to eat a frog, it’s best to do it first thing in the morning. And if it’s your job to eat two frogs, it’s best to eat the biggest one first.”)
What am I looking forward to?

These questions have changed over time, as has everything else about my weekly review. Once you start doing a weekly review, you’ll find ways to change and modify it to your needs. You just need to start and go from there.

Most importantly, when doing a weekly review, take on the role of a supportive friend and not overcritical parent. It is so easy to beat up on yourself in this process. A few weeks ago I fell into a news-cycle doom-scrolling hell and got almost nothing done. I acknowledged that in my review and made plans to turn things around the following week … and I did! Don’t be hard on yourself, be supportive.

I find it interesting that, for me, most weekly reviews are helpful in clearing out all those background processes in my brain and setting me up for a successful week. But once in a while, a weekly review becomes much more when a prompt question unlocks a problem or issue that was lurking just below the surface. You won’t get to those sorts of problems until you specifically look for them.

If you haven’t tried weekly reviews, I would ask you to commit to a ten-week experiment. Ten weeks isn’t a long time, but will be long enough for you to see the benefit of a weekly compass check.

Boxing in the News

I have always been pretty good about not letting social media get in the way of being productive. For whatever reason, I don’t easily fall into the Twitter infinity pool. I discovered in 2020, however, that this super-power does not apply when it comes to the news. Between COVID and everything else 2020 brought, I found myself spinning into multiple hours of reading and consuming news coverage too many times. I thought I had it licked by the end of the year, but last week relieved me of any such delusion.

The Trouble with the News
A certain amount of knowledge of current events is important and can be helpful. From watching the news, I have been inspired to donate money and time to worthwhile causes. I also think it is important, on a personal level, to understand what is going on in the world. When I was growing up, the news was typically a half-hour program viewed by networks as a civic duty more than a profit center.

That has changed however. Now there are fully 24/7 networks on whatever band of the political spectrum you want. These networks are built around the premises of sucking you in and keeping you there. It is very much a profit thing, and they are good at winding you up to stick around for that next segment/hour/day.

While some news is good, too much news is bad. There comes a point where you stop learning about current events and instead become zombified by them. Too much news can poison you.

So I’ve started taking steps. First, I put a box around the news. I try to keep news consumption down to 30 minutes a day. There are lots of ways to do this, but one way I’ve found useful is the Reuters app on the Apple TV. You can log into it and get the day’s news boiled down to as little as 10 minutes. It then gives you a summary of national and world news, and once it finishes, it finishes. It doesn’t ask you to stick around.
Another practice I’ve been working on when watching the news is to do a little internal check-in once I turn the news off. “How am I feeling right now?” “How agitated am I?” “If I’m wound up, is there anything I can do to make a difference?” I also try to disconnect after watching the news. I’ll go make some music, pull some weeds in the garden, or take the dog for a walk. Then I can get back to work with a clear head.

If you’re like me and susceptible to the news infinity pool, take some times to build your own box for the news.

The Hustle Is Dead to Me

For the longest time, I proudly considered myself part of “the hustle”. I always kept many oars in the water, and they were all paddling, seemingly at once. Time for reflection or rest was for wimps.

I grew up with that work ethic, and I never questioned it. Over the last several years, I have thought a lot more about how I spend my time and what are truly my priorities. As a result, I find myself spending a lot more time on the things most important to me and a lot less time on everything else. I am no longer a rowboat. I am a speed boat with comfy chairs.

It’s only recently, with this new insight, that I have come back to this idea of “the hustle.” With a little wisdom and understanding, I now realize that “the hustle” is dumb.

The rules, as taught to me, were wrong. It is not he-who-works-most wins. It is he-who-focuses-on-what-is-most-important who wins.

The Relationship Between Task Lists and Calendars

I’ve written about hyper-scheduling and using my calendar to keep myself in check when planning tasks. Those posts often get questions from readers about the exact relationship between my calendar and my task list. If you keep both a calendar and a task list, it can get confusing to figure out what goes where. Of course, you know the dentist appointment goes on the calendar, but if you are going to get the most out of that calendar, it should be used for much more.

Your task list should be the keeper of all tasks. It is the full inventory of things you plan to do. If, however, you’re like me, that inventory is pretty full. There is no way I’m going to wake up one day and complete every task on my list. Honestly, there are years worth of work in my OmniFocus database.

The purpose of the task list is to bring order to that chaos and give you a framework to hang current and future tasks and keep them in perspective. The goal is that when you plan your days and weeks, you can easily pull the wheat from chafe in that task list and know that out of all of those things, which are the ones that move the needle for you right now. Figuring out what is essential right now is the entire reason I’ve invested my time in mastering OmniFocus (and made the OmniFocus Field Guide). I want to get to the tasks that need my time with the smallest time investment on a daily basis.

It’s at that point that my calendar joins in the dance. Once I have picked my tasks for the day or week, I need to plan when I will accomplish them. To do this, I need to answer a few hard questions:

How long will this take?
Do I have that kind of time available?
Exactly when will I give it that time?

Let’s break that down further.

How long with this take?

As humans, we are generally terrible at estimating how long it takes to get something done. We usually vastly underestimate the amount of time required. If this is new to you, I recommend taking your initial time estimate and doubling it. Let’s say one of your on-deck tasks is a client proposal, and you immediately think “one hour”. Make it two. You can always scale back later, but if you are using calendar blocks and they are too short, you will fail at it. If it ends up taking one and a half hour to make that client proposal and you have a one hour block, you’ve already crashed. If instead, you had a two-hour block reserved, you can take a break for thirty minutes and play with the dog or work on something else. Bad time estimates are where most people have trouble when calendaring tasks.

You may find that you also have a set of essential but small tasks that also need to get done. I don’t block time for small tasks, but I will block time to handle a pile of small tasks. In my case, I often have a one-hour calendar block called “Legal Flags”. Those are small flagged client items in my OmniFocus database that I can lump together and get through quickly.

Do I have that kind of time available?

This process starts with a small list of tasks and you setting time estimates for them. Even with a short list of tasks, you may find you run out of time. There are only so many hours in a day. If you have realistic time estimates, you may find that you don’t have enough time for all of your selected tasks. That’s okay. It happens to me nearly every week. You then have to decide what gets done now and what has to wait for later. This process is the payoff of combining your tasks with your calendar. It allows you to be realistic about what can (and can not) get done in the time you have. It’s the difference between a realistic list of tasks for the week that you can feel good about finishing and an unrealistic list that may sap all of your energy by Wednesday as you realize you have no hope of getting it all done. I guaranty you will get more done with a realistic list than an unrealistic one.

Exactly when will I do it?

The final step is to put those task blocks on your calendar. They are just as crucial as dentist appointments and will help you keep on track throughout the week in getting those most important tasks done.

So in answer to the question of what goes on my task list and what goes on my calendar, I’d say while all of my tasks are in my task list, only a select few graduate to the calendar. I’d also avoid going through this process for tasks any further than a week out. Everything is continuously in motion, and it isn’t easy to know what will be the priority more than a few days from now.

Want to see what technology I use to pull this off? There’s a post for that.

Personal Retreat Technology

A few days ago, I published a video about my personal retreat experience. Since then, I’ve had many people ask me to explain further what technology I used. I’m about to explain what I did, but before I do so, there is a good argument that you shouldn’t take any technology on a personal retreat. It’s so easy to let the tech take over.

However, in my case I wanted to do a lot of typing and dictating, and tuning out infinity bucket apps has never been a problem for me so I brought along some Apple gear. If you want to bring technology and are worried you’ll be wasting time in social media instead of doing the hard work of a personal retreat, turn off your WiFi and cellular radios. I didn’t need to get that drastic, but if I’d caught myself lurking on Twitter, I absolutely would have done so. (I also did bring along pen and paper, just in case.)

If you are going to use technology, there are three phases to my version of a personal retreat:

Identifying and writing out your roles.
Asking tough questions about each role.
Planning for action in relation to each role.

For steps one and two, you could do this with any tool for managing words. A text editor would be fine. Apple Notes or even TextEdit could get the job done. The next level would be an app that supports headings and organization, like Drafts, Ulysses, or even BBEdit. As I explained in the video, the process is very non-linear. You’ll find yourself bouncing around among roles and questions a lot. For that reason, another excellent tool for this process would be an outliner or mind mapping app with both the ability to add plenty of text and folding branches. My two favorite apps for this process would be OmniOutliner or MindNode.

For this past retreat, I spent the first two days using Roam Research. I’ve been experimentally using Roam for a few months. It’s a powerful tool that combines the ability to turn anything into an outline with the ability to link any outline block in your Roam document (“graph” in Roam parlance) to any other outline block in your Roam graph with no friction. Roam is an excellent tool for this process … except for its immaturity. While Roam is a bit of a mind-bender and makes connecting thoughts very easy, it is still very new, and there are a bunch of parts to Roam that are not ready for prime time. My biggest concern is the lack of security. As I started to pour my heart into the retreat document, I became concerned about lack fo security in Roam, a web app, and ended up towards the end blocking and copying into OmniOutliner, which lacks Roam’s cool backlinks but has better security. (We’re going to be digging in on these research tools on an upcoming episode of Mac Power Users, and I’ve got a lot more on my mind when it comes to Roam and its competitors.)

For part three, turning my retreat ideas into action, I relied heavily on OmniFocus and Drafts. A lot of the process toward the end was writing plans out for myself and my collaborators. All of those started as blank text files in Drafts and grew into much more as I worked through the process.

I also set up a series of new repeating tasks and projects in OmniFocus to help keep myself accountable for some of my planned changes. Using a set of custom perspectives and review frequencies, OmniFocus can help keep me honest.

Looking back, my personal retreat technology wasn’t particularly novel or demanding. You need a place to write words down. You need a place to turn words into future actions. To go much beyond would probably just be a distraction on a retreat.

Mistakes Book

Mistakes: The Foundation of Your Small Business.JPG

Dave Hamilton and Shannon Jean have been making The Small Business Show, a podcast about … well … small businesses, for five years now. It’s a great show, and I’ve even guested on it.

Recently Dave and Shannon released a book called We Love Mistakes that details so many potholes small business people often fall in. If you run a small business, or better yet, are thinking about starting a small business, this is required reading.

Course Corrections

When looking at yourself and how you get through your day, it’s easy to get hung up on big things, but so often the big things don’t happen overnight. They take time, planning, and money. And that is assuming you have any control over the big things.

In contrast, little course corrections can happen every day. They are easy to implement, and they take little effort to put into action. Best of all, small course corrections, even just a 1-degree turn, make a big difference over time.

Whenever I feel stuck and unable to move the icebergs in my life, I try to step back and start making little course corrections, so the iceberg is no longer a problem.