Grounded & Steadfast

est. 2008

I’m currently 40,000 feet in the air as I write this. There’s nothing quite like 6 hours on a plane with no connectivity to allow one to meditate on and process the results of a 7 day team retreat. It also leads a long task list in one’s notebook!

What I found myself meditating this time around was the people. How we’re all so varied, so unique, and yet with striking similarities repeated across a group of individuals. After spending 7 full days in the same house with 22 other people, I’ve realized two things.

First, the topic of introversion vs. extroversion so quickly becomes silly and unproductive. It’s a spectrum, plain and simple. A broad one. We all fall somewhere on the line, with different characteristics displaying where we live along that spectrum. What may classify one person as introverted may be completely different for the next.

Second, in her article titled The Outgoing Introvert, Jenn Granneman poses the idea that some introverts are social and not shy, enjoying the spotlight on occasion and not fearful of meeting others. Yet, when the battery gets depleted, these people need time alone in order to recharge and be ready for the next event.

This is exactly how I found myself. The past week drove that home once more. I love the chance to have some face to face time with my teammates. Getting in front of the team to speak is fun, not intimidating. Voicing my opinions in a healthy team debate is not a problem. And I cherish spending time with the newer teammate I’ve met for the first time, getting to know them a little better (or a lot). The concept of a team retreat for remote workers is critical to my job satisfaction.

It’s also exhausting!

Our last night was a great illustration. As we finished our last dinner together, the topic turned to what we’d do for the rest of the night. When someone mentioned watching a movie, one of my colleagues leaned over and said, “How about talking? To people? That’s what we’re here for.” And he was right.

But after 7 days of being in the company of others from morning to night, as enjoyable as it was, talking was the last thing I wanted to do. My teammate clearly is energized by the interactions. I had nothing left and wanted to just shut down. Neither is wrong; it’s just how we work.

As I looked around my other overtly introverted teammates, I could see the same thing on their faces. And so I enjoyed a good movie with a couple of other folks. Once again, I came away feeling blessed for working on a team that values diversity and allows us to be ourselves. We push each other to do our best, but all while respecting and embracing our differences.

I like that.


How I Use Day One

Day One is one of those applications where I’ve always known I was underutilizing it. For one, I’ve never had a consistent journalling habit. And secondly, it has a lot of functionality that I simply never put to use.

This has been true from day one (sorry, not sorry), but became even more pronounced with the launch of Day One 2. This version brought multiple journals, better support for images, and many other small touches. And to follow that up, they recently announced support for IFTTT. That option opens up a world of automated journal entries.

Now, automated journal entries sounds like a phrase that is ripe for misuse. One can picture a pipe of content that is never viewed or revisited, meeting no purpose. However, with some careful thought, I think this can be put to good use.

How I’m using Day One today

I’ve slowly been increasing my usage of this powerful app since Paul invited me to the beta of version 2. Here’s how …

A work journal

My first step was creating a second journal titled Wildbit. Every day where I’m working on long term initiatives, I open an entry and keep the app on the side of my screen (using Moom for precise widths and spacing, natch).

Tracking what I do each day

As I go through my day, I jot down what I’ve done and why certain decisions were made. This helps me for a couple of reasons. For one, your future self is always questioning why you took a certain approach. As will my team. So it’s nice to have a trail to review and recall why something was done.

Second, our teams shares monthly reports to the entire company. It’s a lot nicer writing those reports when I don’t have to scour through email, Slack, and Paper.

Good writing

Another way I’ve been using Day One of late is a reading journal. Although it’s possible to archive bookmarks here, I already do that in Pinboard. So I do not feel the need for that type of thing in Day One.

However, I have not had a good place to store all the highlights found in my reading. And so I created a Reading journal, hooked up the Day One IFTTT channel, and created some recipes. Now, any time I highlight text in Instapaper, the words and the details of the quote are stored in a Day One entry.

Tracking quotes

The last thing I did here was create a recipe to have article tagged with “like” in Pinboard to be added to a new entry in Day One. Sadly, news just arrived that IFTTT is removing Pinboard from their list of supported channels (here is Maciej’s response).


Last, one nice addition to my journaling habit has been recording all the great beers I’ve tried. Since I love the care put into the labels as well as each brew, Day One’s support of photos is helpful. Every time I try a new option, I take a picture of the bottle and tag the entry “brews”.

Mmmmm, beer

The nice touch here is that my wife doesn’t really care to see beer bottles mixed into the family pictures. And so I can choose to not have photos taken on my phone in the Day One app added to my Camera Roll.

98% of the photos taken on my phone are done so in the Camera app. And if I ever want to add a certain photo of a child or event, I can add it to Day One. But being able to take a photo directly in the app is helpful in that I can keep my iCloud Photos library in a more clean state.

That sums up my current usage. Have any great use cases yourself? I’d love to hear it!


Are product managers a burden to productive teams?

The fine folks at Help Scout asked that question. And co-founder Nick Francis seems to indicate that the answer is yes. I quite enjoy the Help Scout blog, specifically the writing of Gregory Ciotti. But this particular piece didn’t sit well.

It starts with a somewhat inflammatory opening statement. The one in big bold text:

To build a great product, you need design and you need engineering. Somewhere along the way, and especially as companies grow, another mysterious role enters the fray: the Product Manager.

Take the work that someone does and add a drop of condescension and you're suddenly ruffling some feathers. Knowing the Help Scout team, this was not likely the intended purpose. But it does read a bit smug.

Again, I appreciate this team (we use their product, which I like a lot). And I appreciate Nick's overall point. But it's not well made and includes some generalizing statements. If he had taken the approach of explaining "this is what works best for our team", one could appreciate the insight and move on.

But he instead took the approach of attacking a role in our community.

But the Product Manager role introduces a couple disadvantages. It takes ownership away from the people doing the work. Designers and engineers become cogs executing a plan when they should be empowered to solve customer pain. Product Managers also add significant overhead to every project, albeit unintentionally.

To the point of designers and engineers being treated as cogs, it sounds like Nick has experience with bad product managers.

But his main point is that having no product managers is good for several reasons. It keeps the primary creators closer to the customer, is a more efficient process, and distributes some key functions to multiple people instead of just one. As he states:

A magical thing happens when there’s no Product Manager. All of the project planning and ancillary tasks become “everyone’s job.” Designers and engineers have to work together to understand customer pain and come up with a delightful solution.


These “chores” become empowering, rather than a burden, because they give people a sense of ownership and responsibility that didn’t previously exist.

There’s truth here. It can be beneficial for designers and engineers to do these tasks. And it’s good to have people with those skillsets close to the front lines hearing directly from customers. The only issue is that when they’re doing these tasks, they’re not doing their primary tasks. Instead of designing and developing, they’re product managing.

But Nick is making the case that this is more efficient.

As a company grows, product development gets slower, takes more people and requires more effort. We often misunderstand those challenges and insert Product Managers to babysit and make the process more efficient … I’d argue that this role exacerbates the problem instead of solving it.

His entire point of reduced efficiency and increased overhead seems misguided. If a PM adds bloat to the overall process that gets a team to successful implementation, how does taking the important functions s/he performs and having designers and engineers do them make the overall process faster?

It doesn’t.

Every hour a designer spends doing user research is one hour they're not designing. Whether that is low fidelity idea generation or high fidelity iterations of the final solution, the designer is researching instead. The same is true for the developer.

There are certain functions that are vital to successful products. Who performs those functions isn’t terribly important in and of itself. If a team prefers to have designers and developers do user research, write technical specifications, and manage the overall development process, that process can work.

But so too does having one person own the responsibility of those functions. Someone whose sole purpose is to gather all the necessary information, get it into the hands of the creators, and manage communication as smoothly as possible. And most important, someone who spends their time ensuring the goals of the business are aligned with the needs of the customer.

Suggesting that you can take all of that and just add it to the role of designers and engineers is a fallacy. I'd tend to believe this approach often results in a mediocre end solution as people are wearing too many hats to be truly proficient at their primary craft.

An experienced, proficient product manager is an expert on those functions because it's all s/he does, every day. Having an expert in this area frees up designers and developers to do what they do best, as well as empowers them with the right information and focus.

Last, I wonder how the customer success/support staff at Help Scout feel about this statement:

At Help Scout designers always have the final say because they are closest to the customer.


Update: Nick proves he's a class act. He's updated the post based on some feedback he's had with several folks, including yours truly with what you see above.


You may have come across this article from last fall at some point. It’s a long, well thought out piece by Kim Stanley Robinson exploring the actual potential for humans to be able to live on a planet other than this one. His prognosis? Not good!

As someone who spends a lot of time lamenting what we’re doing to this planet, I appreciate a science fiction writer taking the time to add a dose of reality to our consciousness. As he starts out, he reminds us that interplanetary travel is an idea that has been around for not all that long:

Humanity traveling to the stars is an ancient dream, and a late nineteenth and early twentieth century project, proposed quickly after the first developments in rocketry. The idea spread through world culture, mainly by way of science fiction

Since then, due to the explosion in popularity of science fiction, this idea has become a rather integral part of our culture. Not to simply travel to another planet (getting to Mars is obviously feasible), but to find one that could support human life and then begin to colonize it. It’s to the point where most of us believe it’s just a matter of time. Robinson basically takes a detailed approach to say, “Maybe not.”

If you spend much time at all reading about climate change, you may be concerned about timelines. On the one hand, the time it will take us to find and colonize a inhabitable planet has not shrunk much at all (perhaps it’s even expanded). On the other, the timeline where the earth’s environment becomes uninhabitable seems to shrink every time you read about it. We would appear to be running out of time.

Let’s hope a lot of the new science fiction is focused on renewing the state of this planet. It seems to be a far more likely chance of success. Personally, I try not to fret too much, for I have another hope. But I do want to make choices that reflect reality, not fiction!


Moving From OmniFocus

The last time I took an in-depth review of my needs regarding managing tasks and projects was almost two years ago.

My conclusion was that OmniFocus both fit my needs and was the most enjoyable option to use. So much so that when Stephen & Shawn asked me to write about “GTD apps” for The Sweet Setup, it was more an exercise of reviewing the capabilities of each option rather than having to choose a winner.

And that’s how it’s been for 2 years. Until Sven.

Over the past few months, I’ve seen Ben Brooks write about 2Do, some new kid on the Mac personal productivity block. And Ben mentioned that he gave it a look when Federico touted its features. But it wasn’t until I saw Sven give it a test run that I was sucked into giving 2Do a look.

I came away impressed.

Testing a new task management tool is usually more trouble than it’s worth. Moving tasks around is usually less useful than actually doing them! But I had just finished up Deep Work, What’s Best Next, and The Focus Course. I was going through the exercise of evaluating how I work and what I’m working on in all areas of my life. Taking a high level view, identifying my purpose, and listing my roles and responsibilities turned out to be a great chance to put all the small steps in place. Even in a different tool.

After 2 weeks of trialling the mobile and desktop app, I was sold.

What makes this app so good? First, it’s a joy to look at. The interface is clean and well designed; specific functionality of the application is hidden until needed.

As for the feature set, it as just as robust as OmniFocus. But the beauty of 2Do is that it combines the best of both worlds. It’s as functional as OmniFocus, but presents that functionality in a more enjoyable manner, more like Things. But where Things ends in what you can do with it, 2Do delivers all the customization you need.

I’ll use the organization of your tasks as a good example. In OmniFocus, you can add projects and folders. Now, most of us have many roles to play and have tasks related to each. Many OmniFocus users break their “Areas of Responsibility” into folders at the base of their system. You can then add projects under each of these folders. It also allows you to create “single action lists”, which represent those areas where you have things to do with no end date (whereas projects are intended to have an end date).

In contrast, 2Do allows you to create lists and groups to organize the areas of your life. In your lists, you can then add projects and checklists. Both of these can contain tasks. And you can break this down further to include sub-tasks.

At the heart of any task management tool lies how the app will allow you to categorize your core responsibilities. It truly is the flexibility that makes 2Do compare so well to the other options.

2Do Hits All the Sweet Spots

While most of the big players in the personal task management space for OS X are high quality, there are a couple of aspects of 2Do that drew me in.


First, the organizational baseline of 2Do was closer to Things than OmniFocus. Things was the first app I used in this category as a Mac user; it was part of what drew me to the platform. But where Things was rigid in its organization, OmniFocus allowed a little more fluidity. It enabled me to create custom views that fit my work days or contexts (common situations) better.

However, 2Do takes that customization to another level. Where OmniFocus allows you to create Perspectives based on limited options, 2Do’s smart lists are far more flexible and enabling. Where OmniFocus is rigid in terms of where a task can be assigned and located, 2Do adds a lovely method for storing tasks.

Let me give a concrete example. Since everything in 2Do is a list, when you're adding a new task, it can go under one of your main lists. But that list can also contain projects and checklists. Your new task can sit on its own under the parent list, or you can easily add it to any included project or checklist.

2Do has a good overall structure

Sounds obvious, right? But this is something that is not possible in OmniFocus … new tasks must be included in an existing project under a parent folder.


At the same time, 2Do is nicer to look at than OmniFocus. I sure appreciate the work of the folks at OmniGroup, but their apps are not the most pleasing visually. There are no theming options with 2Do, but the UI is already very nice and customization comes with the colour of your lists and the size of the font.

It also boasts a pleasing UI

2Do is very thoughtfully designed. The layout of the information allows for differing densities, and even with all the details in view, there is never a sense of being overwhelmed. This is an especially nice touch on iOS.

Search & smart lists

One of the most powerful aspects of 2Do is the search. You can identify any criteria to create a custom view of what you want to see. Once you have created this view, you can save it as a smart list.

Search is powerful in this app

This is essentially the same as custom perspectives in OmniFocus. But there is a little more possibility and control here.

Odds & ends

There are a few other items that have gotten my attention over the weeks of using 2Do. One is the amazing keyboard support. Everything in the app can be done via the keyboard. The list of shortcut options is lengthy!

Key shortcuts aplenty

Another nice touch is the prioritization of tasks. You can set any task, project, or checklist to have one of five levels of priority. The default is none, the lowest level of priority. The highest is a star. It’s just one more way to allow you to mark and view tasks in ways that make sense to you.

Last is the support for tags. The ability to use tags in 2Do is much like any other application. But in a task management app, this allows you do view tasks across lists. So for GTD lovers, tags can be your contexts.

Where it lacks

Is there room for improvement? Of course. For one, syncing over Dropbox is a tad slow. There does not seem to be any option for background syncing like OmniFocus has. As well, some keyboard actions are counterintuitive and take time to become accustomed to.

The biggest issue could be considered not the lack of functionality, but the abundance of it. You could twiddle knobs all day with this app. Thankfully, 2Do has been designed well so that the functionality is there, but is not in your face and distracting one from focusing on the tasks more than the tool. As Kathy Sierra puts it in Making Users Awesome:

There’s a world of difference between having choices and have to make choices.

Indeed. 2Do strikes the right balance.

Would I advocate moving to this tool? Only if you have a good opportunity to do so and a need for change. OmniFocus, Things, and all the other options are great tools. Hey, pen & paper are a lovely option as well!

But if the opportunity presents itself, give 2Do a look.


Back to the topic of why newsletters are a good choice for writers.

This piece by Simon Owens perfectly sums up my thoughts. In it, he opines that email newsletters are similar to the handmade zines of the 70s, 80s, and 90s. In contrast to carefully edited and displayed content of the web, newsletters are more haphazard:

Many newsletters feature a hodgepodge of unrelated sections, images, and GIFs, and they take a distinctly informal tone in their writing.

What makes this format work for both writer and reader?

It could be that, like those within the zine community, newsletter readers enjoy feeling like they’re in some sort of exclusive club. Sending a newsletter seems more like a private, intimate conversation compared to when you write for the open web.

But he finishes by stating that newsletters could suffer a potentially gloomy future:

Given our renewed obsession with Inbox Zero and the general feeling that we already receive too much email, it might soon become harder for new independent newsletters to break through the noise.

For now, it’s a fun tool to make use of!