Why I Pay for Email (and Domains)

In a world where you can get free email accounts seemingly anywhere, I recently decided to pay for an email service. This doesn’t mean that I don’t still have Gmail, Microsoft/Hotmail, iCloud, and Yahoo accounts–but it’s another step back toward paying for products and service instead of being the product. I chose Fastmail on the recommendation of a friend who has used them for many years.

Fastmail’s value proposition and advertising revolves primarily around security, privacy, no ads, no tracking–all of which are good. But the features I’ve found the most valuable so far are actually their search and mail rules. I have a fairly common first and last name. And unfortunately for me, this has meant receiving a lot of email in my Gmail account over the years that is intended for someone else. The email contents range from the merely annoying (emails from various GOP candidates for political office) to documents with PII and other content that is supposed to be confidential. But Fastmail’s mail rules setup allows me to delete that stuff from my inbox without ever having to see it.

Another feature Fastmail offers is Masked Email. You can use it to create a unique email address everywhere you log in on the web, and block addresses if you start receiving spam from them. What I do instead is use two domains that I own to create unique email addresses on-the-fly. What the setup with Fastmail lets me do is make up an email address on the spot with one of those domains and know that I’ll receive any email sent to it. For example: I go to Walgreens the other day, and made up an email to give to the person at the register for the myWalgreens program so I can get the associated benefits without giving them my real email. The mail rules let me filter these emails (and others like it) out of my inbox.

The email that’s actually intended for me I can label, filter, and receive notifications for if they’re really important. Fastmail also lets you create a rule based on a single message to control how future messages are handled (a capability that can also be applied to blocking senders). Whether I’m using the web application on my MacBook Pro, on the mobile apps on my iPhone or iPad mini, I get the same experience of email actually being useful again–including not missing important ones. It might be nice to have an actual desktop client, so I may try the FMail client someone developed and see if I like that better.

Fastmail makes it easy to onboard with a 30-day free trial where you can use it as the interface to whatever free email account you currently use the most. For me, that’s still Gmail. The import process (which had years of emails to pull over) worked perfectly. Because Fastmail can receive and send Gmail, I’ve had no need to use the Gmail web client or its mobile apps directly for weeks. I’ve even deleted Gmail from my phone and tablet.

I still have plenty of work ahead when it comes to unsubscribing my Gmail email address from so many things! Email lists, newsletters, stores, and all manner of other online services in the nearly 20 years since I first signed up for it. But as I do (and re-subscribe to just the things that matter most), Fastmail is helping make email a useful tool again.

Getting (and Staying) Organized

During the past year-and-a-half as a software development manager for a local consulting firm, I’ve tried a number of different tools and techniques to keep me organized.  As my role expanded to include business development, hiring, and project management tasks, there’s been a lot more to keep track of.  I meet weekly or twice-monthly 1-on-1 with each team member on my current project.  “Move it out of e-mail” is my primary objective for getting organized.  The rest of this post will elaborate on the specific alternatives to e-mail that I tried on the way to my current “manager tools”.
Beyond e-mail and calendar functionality, Outlook offers a To-Do List and Tasks for keeping organized.  Both provide start dates and due dates.  The To-Do List is tied directly to individual e-mails, while Tasks are stand-alone items.  I abandoned the use of task functionality pretty quickly.  I used the To-Do List as recently as July of this year, but I see it as a bad habit now.  I rarely end up clearly the various options to flag an e-mail for follow-up (Today, Tomorrow, This Week, Next Week, No Date & Custom), so they become an ever-growing list where I only very occasionally mark items as complete.  In addition, the search functionality in Outlook never works as well as I need it to when I’m trying to find something.
Once I passed the six month mark with my employer, I felt comfortable enough to introduce weekly 1-on-1s as a practice on my project.  After a couple of weeks of filling out a paper template from these guys for each team member on my project, the need for a better solution became readily apparent.  Lighthouse is the name of the company and their product, a web-based application for managing your 1-on-1s with staff.  After the free trial, I chose not to renew.  While I like Lighthouse, and the cost wasn’t prohibitive, my employer wasn’t going to pay for it.
I liked the ideas in Lighthouse enough that I tried to build a simpler, custom version of it myself.  Increasing work responsibilities (and the birth of my twins, Elliott and Emily) erased the free time I had for that side project.  Lighthouse maintains a leadership and management blog that I’ve found to be worthwhile reading.
I first started using Trello years ago for something not at all related to work–requesting bug fixes and enhancements to a custom website my fantasy football league uses.  I didn’t consider using it for work until I was re-introduced to it by a VP who uses it to keep himself organized.  Once I reviewed a few example boards and set up a board to moderate weekly business development meeting, new possibilities for its use revealed themselves very quickly.  As of today, I’ve got 4 different boards active: 1 for “hiring funnel” activities, another board for business development tasks, a 3rd for project-specific tasks that don’t fall into a current Scrum sprint, and a 4th board as a general to-do list.  The last board turned out to be a great solution for capturing information from my 1-on-1 meetings.  It also tracks my progress toward annual goals, training reminders, and other “good corporate citizen” tasks.
The free tier of Trello service offers the functionality that matters most:
  • create multiple boards
  • define workflows as simple or complex as you need
  • create cards as simple or complex as you need
Markdown formatting, attachment support, due dates, checklists, archiving, the ability to subscribe to individual cards, lists and/or boards and collaborate with other team members of Trello combined with the key functionality above has helped me become much better organized and able to communicate more consistently with my team members and executives in my organization.  The search capability works much better for me than Outlook as well.
I’ve only gotten a handful of co-workers in my organization to adopt Trello so far, but I keep recommending it to other co-workers.  I’d like to see our entire business unit adopt it officially so we can take advantage of the capabilities available at the Business Class tier.

Figuring Out Google Wave

I recently received an invite to Google Wave (thanks Rory).  From the few minutes I’ve played with it so far, it seems to be Google’s next offering in collaboration (Google Docs is probably their first).  I’ve still got some spare invites, so send me an e-mail if you’re interested in trying it out.

One of my bosses from a previous company came across a couple of links that explain Google Wave:



I’ll probably be checking these out when I have time (if I’m not distracted by other “oooo shiny” toys, or life in general).