Mitch's Core Dumps

Last night, I was ranting on Twitter again.

This time it was about task management software. There’s several options out there, but everything I’ve looked at has fundamental flaws. I’ve settled on Remember the Milk for now, but I’m not thrilled with it.

Here’s what I want:

• A clean UI that is fast and optimized for brain dumps of a large number of tasks. Smart tag management.
• Mac-native application.
• A web UI for when I don’t have my Mac handy.
• Storage in the cloud and locally. I want to use it when the cloud is down, when my connection to the cloud is down, on the subway, etc.
• I don’t want to bring my own cloud service. I want to buy a service that someone else runs.
• Integrate with Google Apps: My calendar should show deadlines, the task system should have access to my address book, etc.
• Good iPhone application with emphasis on new task capture and the ‘next’ to do list.
• Nice to have — Outlook for Windows plug-in to sync tasks into Outlook’s to do. I use Outlook 25% of the time for Xobni.
• Nice to have — Integration with BaseCamp. I don’t use the To Do stuff there much, but people assign me tasks in BaseCamp. It would be nice to see those in my To Do list (and be able to click to go to them in BaseCamp).
• Nice to have — Integration with Salesforce. Again, tasks are created in Salesforce and I’d like to see those in my central view of the world (and be able to click to go to them in Salesforce).
• Nice to have — Show today’s calendar item from Exchange / Google Apps. This is particularly important when planning what to do next and identifying how much time I have from now until my next commitment. I often flip back and forth between calendar and the to do list. Neither Outlook nor Google Apps get this view right.

Here’s what I’ve tried:

• Things — I have bought Things for the Mac, iPad, and iPhone. However, after it trashed its database and tech support basically told me “I don’t care”, I haven’t been able to get back into it. Fundamentally, it is missing cloud sync, which makes it somewhat useless for someone who travels a lot. My corruption seemed to be related to syncing with the iPhone, which doesn’t inspire much confidence and so I would stop syncing with the iPhone. However, the Things UI is almost perfect. No one else seems to hold a candle to it.
• OmniFocus — I tried it a few years ago when it came out, but it was riddled in complexity and not as smooth as Things. This might be fixed now. I would like to try it again, but Omni doesn’t offer a production cloud service yet. I generally like Omni products.
• Remember the Milk — I like that I can use it from any computer. However, it’s tedious for dumping in a lot of tasks. Setting a new location on a task requires a manual step of creating a new lcoation. Why can’t I just type in my own locations and let it sort them out? The details for a task are presented on the right side of the window, rather than right next to the task, which leads to a lot of mousing around. In fact, the whole UI is about mousing around and a lot of clicking. For example, I have a task with some notes. When I click the task, it shows that I have 1 note, but I have to click again to see it. Just show me everything. I’d like something that I can control entirely from the keyboard. However, the iPhone app is quite decent based on a cursory examination. No Outlook integration.
• Evernote — Not really a task management system, but I had heard of people using it as such. Great for what it does, not great for task management. But the cloud service, native apps, and sync model are all perfect.

I will keep plodding along with Remember the Milk for now, but I’d really like to see a Things-like UI for Remember the Milk, either as a sophisticated JavaScript UI or a Mac application. For busy professionals, task management is a huge tool and nothing seems to get it right. There’s a market hole here that someone needs to fill. Several people have asked, “so why don’t you write it?” I am very busy with another software company right now and one at a time is the maximum for me.

P.S. If you know of a solution that I missed that might work better for me, I’m all ears! mitch.haile@gmail.com

I recently received an email asking what helps me stay organized. This is actually interesting phrasing, as it doesn’t presume that I am organized, nor does it presume that at one point I needed to “get organized.”

I mulled it over from this perspective and here are a few things I do to stay on top of things while minimizing stress. Most of these tips are about preventing the consequences of forgetting or losing something (stressing out), rather than remembering everything (being organized).

• TripIt Pro — The last ~150,000 miles of travel I’ve done, I did with the help of TripIt Pro. If you are doing any amount of travel, you owe it to yourself to at least get the free account. I felt having the iPhone app was hugely worthy of the subscription price. TripIt lets me reserve hotel, car, and flights using my normal tools (Virgin, US Airways, Enterprise, Orbitz, Hertz web sites) and then forward the confirmation emails to TripIt. The itineraries are generated and appear in my calendar Outlook/Google/iPhone, in the TripIt app (with phone numbers, maps, directions, confirmation numbers). This is a huge time saver. TripIt does not handle complex itineraries involving numerous one-way tickets very well, but it does get all the data in there. It also integrates with LinkedIn, so you can advertise to your connections when you might be around to meet up for coffeee or dinner. Totally worth it. If that wasn’t enough, TripIt also integrates with all the frequent traveler programs. How many Starwood points do I have? Choice Hotel points? United miles? TripIt has the answer in one place.

• Detailed calendar items — when scheduling a meeting, I dump in everything I need to know — the address, phone, email, name, etc. of who I am going to be meeting. This lets me rapidly punch in coordinates into a GPS or phone someone if I’m going to be late without having to dig back into my address book or emails.

• Aggressive calendaring — I set all kinds of reminders for myself in advance on my calendar. I have a reminder that someone needs to trim the roses in the yard in September. I have a reminder about my parent’s cat on days I expect I might go visit (holidays). Oil changes, gutter cleanings — use the calendar system to track everything you need to do, not just the primary objectives in your life.

• David Allen’s Getting Things Done — I don’t use every dimension of David’s system, but I use a lot of it. I bought a really nice label printer and label my files. I file everything I want to keep, even manuals for appliances. I keep proper inboxes and carve out time to dig through them. I use a mixture of Things, Evernote, and Basecamp to organize task items, notes, and collaboration with others. I manage development heavily with Bugzilla.

• Redundancy — I have built a lot of redundancy into my life. I have 4 chargers for my MacBook Air, about 6 chargers for my iPhone, and two GPS units, one on each side of the country. Two sets of clothes — I do all of this to minimize my travel load when commuting between Silicon Valley and Boston. I can go to the airport with my driver’s license, credit card, and MacBook Air and nothing else, go to the other side of the country, and have everything I need. This means I don’t have to remember very much before a trip between these locations.

  As a less extreme example, I keep stacks of business cards in rubber bands in my car, office, home, jackets, laptop bags, so I generally don’t have to remember to bring cards. The point here is to put things in places where you will need them later so you don’t have to remember to bring them with you.

• Connectivity — Even if I forget a file somewhere, it’s often in Basecamp or Evernote. And if not, I have remote access configured for my non-laptop machines in case I need to grab something remotely. I carry an iPhone and also have a Verizon MiFi for when AT&T isn’t working or I need to use my laptop in a customer’s parking lot. I buy Boingo for airport/Starbucks/etc. access to WiFi. Boingo at $10/mo is a no-brainer. The MiFi runs a little more, but it only has to save my butt once a year to pay for itself.

• Capture notes with cameras — I use either a regular camera or my iPhone to capture whiteboards. I’ll use my iPhone to document where I parked my car if I’m in a strange area. I dump notes and pictures of whiteboards into Evernote or PowerPoint depending on what I need (or both).

• Organized phone system — I hand out a Google Voice number for those folks who I never want to hear from. Google Voice cheerfully takes the message, transcribes it, and emails it to me. For everyone else, they get an office number. The office number rings my desk in Silicon Valley and Boston. After 30 seconds, it rolls over to ring concurrently my 2 other lines and my cell phone. This means all my voicemails go into a single inbox, rather than having 3 or 4 boxes to check. This also means I don’t miss a voicemail because I was away from my desk, nor do I need to provide folks a variety of phone numbers to reach me. One number does it all (and can be ignored easily too).

• Outsource personal tasks — There’s probably a lot of things you have to do that you don’t want to do. Cleaning house, grocery shopping, cooking, taxes, organizing, yard work, washing the car. Outsource those things that are not relaxing or that you are not getting done.

Stress can get in the way of making concrete progress on projects, so I use the above to minimize “oh shit” moments. When it comes to gettings things done:

• Decide what today’s 1-2 goals are — I do this first thing. This is part of the Getting Things Done approach (Today / Next buckets).

• Sleep well — Cutting short on sleep is a disaster for productivity. Don’t do it. I have a pair of Zeo units that I use to measure my sleep. It has been tremendously helpful in making me be sure I get enough sleep. Eating well and exercising well go hand in hand here. Don’t ignore the hardware of your body.

• Delegate — No one can do everything. I delegate to other team members as it makes sense, or hire contractors to add bandwidth.

• Watch for distractions — Facebook, watching TV, chatting, blogging, tweeting — These can all be huge time sinks, especially if you’re procrastinating. Limit these activities. Remind yourself of your end goal (I want to get an ‘A’, I want to get paid, I want to finish this project, whatever) and get back to work.

• Recognize that some tasks require big blocks of time — This isn’t true for everyone’s work, but if you need big blocks of time to focus in on a creative or complex project, recognize that need and plan for it.

• Be early — There’s rarely a good excuse for being late. Plan for traffic and logistics — sometimes it can tough to find the right building, the right street, or a place to park. Arrive early and you will have some time to review who you are meeting and what the agenda is. This is 70% of the battle. Internally, I am bad at over-booking my calendar at times, but I’m never late to meet a customer or other business meeting.

My system isn’t perfect, but it’s working well for me. I’m always interested in trying things to improve it. I don’t claim to have the best system, this is just what I’ve gravitated towards. Because my job is really fun and largely what I’d do even if I wasn’t getting paid, burnout is a real problem for which I must be on watch. The above tools have let me get more done than I would have thought possible before I stumbled into these solutions and while keeping stress down.

You may note the above lists are about tools more than skills. Fundamentally, I have a lot of drive and desire to make progress every day — this is why I do start-ups. The above tools just enable me to increase my effectiveness.

For years I have been a huge fan of whiteboards. I like keeping lists on whiteboards, I like drawing on whiteboards–whiteboards are hugely useful in explaining and understanding complex technical concepts, managing projects, and so on. Recently, I discovered that using thin-tipped markers lets me get even more done with the whiteboard in my office. My handwriting is poor at best and this does not translate well to brainstorming with a thick marker. However, in using thin markers, I’ve found that I am able to cram more onto the board, write neater, and generally get more out of the whiteboard. I think this is particularly applicable to small meeting rooms and offices where a whiteboard might be only 4×3 or 6×4 feet.

So next time you’re brainstorming on the whiteboard, try it with a few thin markers and see how it works for you.