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Going paper(less): Web 2.0 Organization For Successful Personal Management

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Going paper(less): Web 2.0 Organization For Successful Personal Management

Written by Jonathan Lambert on

One of the (unfortunate) things that comes with running a company is that the corresponding stream of information that comes with simply owning a computer gets multiplied by how much the company is doing. When your company gets moving, the information you have to deal with radically increases.

As I run an "Open Company," meaning I like to hear from people and don't have someone "handling" our calls and emails, the volume increase was startling - much more than I expected. As <a href="">WorkHabit</a> grew in popularity, staff, and as our project load increased, I found myself increasingly inundated with the day-to-day task of keeping organized. It was getting pretty difficult.

For the record, I was already pretty sophisticated in information handling skills. I was using RSS extensively to track conversations, used Google Alerts to keep me appraised of misses, had everything integrated with Google Reader and working on my BlackBerry handheld, and ran my email through local IMAP so I could sync up everything. I was dealing with the information flow pretty well, and then it started to get personal...

Here are the problems I was really struggling with:

  1. How do I "tie it all together" so that my various devices worked in harmony. My requirements were simple - it had to work over the air (no plug in sync, I knew I wouldn't do it if it was a pain). I wanted calendars and email to work seamlessly, but it would be nice to have contacts work as well. This had to push from the handheld back to the desktop too.
  2. How do I deal with the onslaught of contracts, statements, and other materials generated by my personal life and company life? How do I keep them seperate, but deal with them both?
  3. How do I deal with the 30-50+ voicemails I was getting every day? I was getting so many calls that I was sometimes having a hard time hearing clients on the phone as the call waiting would disrupt my ability to hear them so much (really, not kidding, calls seem to come in waves).

The information was coming at me from all sides - I was getting buried. I found, when I mapped it out, that what I needed to fix was:

  1. Voicemail, how do I deal with it?
  2. Email, how do I keep the spam volume down and make sure I get back to everyone every day?
  3. Calendar, how do I keep things in sync across devices?
  4. Paper documents, how do I keep things organized?

I've managed to get a handle on most of this, or at least I'm on a track that makes me quite a bit happier, after a lot of experimentation. I've actually abandoned a lot of the tools that I started with, namely Backpack, and Basecamp integrated on my Macbook Pro with QuickSilver (which I still use and highly recommend), and other tools like Remember the Milk, etc.

I'm not talking about all of the "small company" tools that are emerging in this post (which Basecamp, and arguably, fit into). I'm talking about my personal organization - how do I deal with the flood of information?

Basecamp started off driving a lot of value for me personally around my professional life, though I was resistant to it. After some months, I began to find several key failings in the product, some of which were disruptive. Information began to get locked up in the system, and in other places, and I had no way to search for it. Documents that were attached weren't indexed, so I was spending huge amounts of time trying to "find that post" that contained the document or files I was looking for.

Basecamp was very interesting, because it's foundation is all about blowing open the company doors - bringing the outside in and blurring the line between internal and external communications. This is it's primary benefit, and it's great! But, the lack of sophisticated organization capabilities means that stuff gets lost in there pretty quickly, and it's hard to get out.

I found Basecamp was a great start, but lacked sophistication, and in the end brought questionable lasting benefit. I've definitely started to find this is true in practical application for a lot of the Web 2.0 tools I've been using: they're "feature" tools, meaning they solve enough of a problem to be very useful, but they don't always solve the problem (and aren't aimed to) completely.

So, I started to get frustrated. And that means I start looking for answers.


The first thing that needed fixing was voicemail. This was out of control, but I still wanted to be able to keep the line open. I just needed to be more effective about it.

So, the first thing I did was set up an Asterisk server. This would give me lots of control, but it turned out to be a super difficult challenge, even with our significant datacenter resources, to get something up and working, due to the fact that most providers are either really small, or expensive.

I tried using as a provider, but after lackluster support experiences, and lots of broken promises and an uncanny inability to communicate, we left.

We then tried, but I had problems with them (for the 30 lines I wanted to get working for our company, I had to set up - get this - 30 separate log in accounts. Hrm. It worked, and I'm currently still using it. It'd give it a b - it works, but it's not architected intelligently for anything more than the smallest of customers. Despite it's difficulty, it works well. And at $6/line, it's hard to beat.

I've been using BroadVoice for a long time, but at $30/line (minimum), and an additional $5.95 for the asterisk box (via BYOD), it's a bank breaker (read $906/mo VS $180/mo with voipvoip). For most small businesses, that's a number you'd notice.

The idea is to set up a personal ACD queue with Asterisk, and then forward all of my business and personal lines to it with standard call forwarding. This enables me to set global policies on all my lines, so I can do things like turn off calls while I'm in a conference, or forward my calls to someone else if I should ever want to take a vacation. This solution works well, but it was hard to set up, and tended to break a lot until you worked all the kinks out - be prepared. I had a lot of people telling me I was hard to get ahold of while I was working the kinks out - it was very frustrating.

I'm still using that system for business lines. The main advantage is that messages can be attached to email as .wav files, making screening them a breeze (for simplicity, Vonage supports the same thing, and works very well if that's all your looking for).

I had previously tried, and I might consider it, but it is a really simplistic 1 line solution that doesn't work well for business. And it doesn't do anything that you can't do with asterisk.

To make sure I wasn't missing things, I decided to hand out both my work line, and my cell phone number. That bypassed the system, so after a little while I was right back where I started.

Enter the coolest tool I've found for phone systems in a long while: Simulscribe. By forwarding all my numbers to Simulscribe, it's transcribing them (fairly well actually) down to something readable in email. This means I can read the voicemail wherever I am, including on the blackberry on the go.

Nothing has revolutionized my day more than Simulscribe. It's $30/mo for a high volume user like myself, and it took me more than two weeks to get Sprint to actually set it up properly, but now that it's working, I'm not sure how I did without it. It's changed the way I work.

So, that's phone systems.

Personal organization on OS X: Paperless just means less paper, please.

The first tool I tried was called Yojimbo. It's awesome for notes. It does some really neat things. This worked really well for about 1/2 a day until I tried to archive a Mindjet Mindmanager mind map. This utterly failed. It also relies on .mac (though apparently there are some unsupported workarounds), which I loath due to Apple's inability to "get it" like Google. Next.

I then went through TinderBox, VoodooPad, StickyBrain, and ended up with DEVONthink, an oddly named, but very useful piece of software. Combined with a Fujitsu ScanSnap S510 (see video here) to do two-sided scanning (and business card scanning, a HUGE win to get it all in one), and a Brother 8870DW to handle office functions, it works extremely well for document organization and scanning. I'm actually looking to buy the ScanSnap s300 (lowest price, potential rebates, review), to do on the spot scanning at conferences and events, and other places where I'm dealing with paperload - I don't know about it's OS X compatability, but that's what VMWare Fusion and Parallels are for. The fact that DEVONthink works natively with Fujitsu ScanSnap products is astounding and awesome. Nice work DEVONthink.

It does almost nothing to put these archives online, or bring my organization towards Web 2.0, but in the end I almost didn't care as long as I had something that worked. There is some serious value not being tapped there right now, however.

Calendaring & Email

Google mail was something I've been using for a long time, but when Google Small Business services came out, it was a rough fit. No IMAP support hampered us at first, but now that we have it, it's working perfectly. I now can access my mailbox on Blackberry, desktop, and the web. It's been so successful, we just implemented it for the entire team. I cannot recommend it enough.

There are still problems (for example, messages sent from your blackberry do NOT go to your sent mail), but

I tried the Mobile version of gmail, but it was SLOW and sucked for my high volume use (no background send, takes forever to pick up messages and draft support was confusing - definitely a failure as far as usability goes. Google needs to go back to the drawing board on that one.

We didn't want to use Blackberry Enterprise Server, mostly due to the fact that we wanted to keep Microsoft out of the core infrastructure of our business. The reason? Well, we tried BES on Intermedia, the leading provider, and the day we signed up it was down for almost 4 hours, and 7 hours of service interruption followed. That was the first day. For our requirements, ANY downtime on email is a problem - multi-hour outages are a complete non-starter. And we also found it was expensive.

In terms of calendaring, there is gcalsync (open source, read thread here (and why do I always find Om Malik on this stuff?), thank you lifehacker), you can publish it internally or externally using gsmcal2html (get creative, this is insanely useful, but brittle in large numbers from an organizational management point of view), saraiya (buggy), a startup named mobion who's soliciting for beta users, companionlink (not over the air), but ultimately I'm planning on using syncml. I do not have a working solution for this right now, other than by desktop (thanks and hello to Alex King). There is something I've found while researching for this article called goosync that I'm considering trying. It's 20 euro a year for something useful (free if you want useless), and claims to do what I want. I'll let you know in the comments.

In terms of blackberry contacts, my 8703e now syncs contacts via it's native client and IMAP. It "just works" out of the box - yes! Finally!

I was able to get Apple to behave properly with a few AppleScripts and this stuff. It was useful way back when, but I'm not using much of it anymore...

There are lots of resources on the subject. There are also a lot of complaints.

My summary at the moment: Argh.


So, I've got email, paper handling, and voicemail handled. I'm close on calendaring. What are your experiences? I'll post a followup when I have all this working - it's become somewhat of an obsession now.