Forward to Paper

I’d orig­i­nal­ly thought to title this post «Back to Paper», but the thing is, I’ve nev­er before real­ly used a paper orga­niz­er or cal­en­dar. I’ve tried a few over the years, of course, but noth­ing real­ly took. In 1993 I gave up on keep­ing a paper address book and began record­ing names, num­bers, birth­days and address­es on my desk­top com­put­er using OS/2 2.0’s «Data­base», a rudi­men­ta­ry form-builder that was part of its col­lec­tion of pro­duc­tiv­i­ty appli­ca­tions, along with sticky notes, notepad, and cal­cu­la­tor. Sad­ly, it was not real­ly meant to last, as the «pro­duc­tiv­i­ty» col­lec­tion turned up con­spic­u­ous­ly absent in OS/2 «Warp» 3. I ago­nized over a means of export­ing the data to some oth­er for­mat, but it was not to be, and I had to start over. It’s fif­teen years lat­er now and there is still infor­ma­tion that was lost in that upgrade: peo­ple I lost touch with, birth­days and anniver­saries I don’t know because they were lost.

A smarter man than myself might have sworn off of dig­i­tal per­son­al infor­ma­tion man­age­ment right then, but instead I dove in deep­er. I tried a vari­ety of dig­i­tal watch­es, all that stored phone num­bers whether they had a cal­cu­la­tor or not. Because in the mid-90s a thir­ty phone num­ber mem­o­ry was a lot and also because enter­ing names and num­bers often meant push­ing a sin­gle but­ton over and over again while the dis­play rotat­ed through the alpha­bet, keep­ing a phone book on my wrist was most often an exer­cise in frustration.

Just as frus­trat­ing, though, was my paper address book, full of scratched out address­es, out­dat­ed phone num­bers, and nev­er real­ly in alpha­bet­i­cal order. 

Lotus Orga­niz­er became my new drug of choice. Not only did it promise to keep my names and num­bers, but I could plan out my whole exis­tance. I’d nev­er miss an appoint­ment again! Of course, I did­n’t car­ry my desk­top com­put­er with me, so it rarely helped. I’d for­get where I’d promised to be by the time I got home, and Org nev­er real­ly made for a good calendar.

All this changed with my acqui­si­tion of a sec­ond-hand Apple New­ton in 1996. At the end of 1996 I was liv­ing in Con­necti­cut and inter­view­ing for a posi­tion in Cal­i­for­nia. The hol­i­days were around, which meant inter­state trav­el to see fam­i­ly in addi­tion to zoom­ing ‘twixt the coasts. The hand­held device was just what I need­ed. Or what I thought I need­ed any­how. That Mes­sagePad 130 gave me a way to do writ­ing on the road, includ­ing email, so that I could keep in touch with every­one that I thought I need­ed to stay in touch with. The real break­through for me was the cable that allowed me to upload and down­load infor­ma­tion into my desk­top com­put­er. All these cal­en­dar items and phone num­bers could go back and forth between my desk­top and a device I car­ried with me every­where. When I got some­one’s con­tact infor­ma­tion it could get added on the spot and auto­mat­i­cal­ly added into Orga­niz­er when I got home.

Even with the New­ton I did­n’t keep appoint­ments or to-do lists for very long. I’d start and stay with it for a few days, but it nev­er real­ly took. I spent a lot of time set­ting up recur­ring alarms for things that I would­n’t for­get to do any­way and to-do list items sched­ul­ing for months in advance when I would take the trash out or do laundry.

There are sev­er­al prob­lems with the approach I was attempt­ing. Prob­a­bly the biggest hur­dle is true of any orga­ni­za­tion­al sys­tem: you have to count on it before it becomes reli­able. One starts with a blank cal­en­dar and a bunch of appoint­ments or com­mit­ments filed only between the ears. There’s a tran­si­tion between trust­ing one’s mind and trust­ing the cal­en­dar. If you don’t check the cal­en­dar before com­mit­ing, you’re bound to dou­ble-book, but if your cal­en­dar is blank, it can’t do much good until after a peri­od of rely­ing on the mish­mash in men­tal space while also writ­ing things down. Stick­ing with a sys­tem is dif­fi­cult when it’s not work­ing yet.

Also true of any orga­ni­za­tion­al sys­tem: no plan sur­vives con­tact with the ene­my. After a week of tak­ing the trash out on the wrong day, the nag­ging cal­en­dar isn’t a help, it’s just anoth­er reminder of a fail­ure to fol­low through, even if I’m actu­al­ly get­ting things done, just in a dif­fer­ent order than I arbi­trar­i­ly planned I should a month earlier.

Next: to-do lists! Oh, these are the most evil. I write down the most impor­tant long-term items and end up doing only the most urgent, which are usu­al­ly not the most impor­tant. It’s a clas­sic Sev­en Habits prob­lem: quad­rant four ver­sus quad­rant one.

This last prob­lem tends to cause the explo­sion of the to-do-list to unman­age­able pro­por­tions. As with most areas of unman­age­abil­i­ty, the best thing is to give up, throw it away and keep mov­ing in the right direc­tion. The most com­mon thing is to sim­ply try hard­er to man­age. In my case this has meant fan­cy soft­ware to orga­nize my orga­ni­za­tion. Heirar­chi­cal to-do lists, task-to-time link­ing, project man­age­ment org and flow chart­ing, for me this has always been like hold­ing on to a greased pig: the tighter you hold, the faster it gets away from you.

Not that I’ve ever tried to hold on to a greased pig. But I digress.

Fur­ther­more, dis­play­ing more and more infor­ma­tion on small­er and small­er screens is a lost cause. The New­ton’s screen is almost 18 square inch­es. My Tre­o’s is three. There were a lot of inter­me­di­ate steps, but just imag­ine the pro­gres­sion of less and less screen real estate as my data and dis­play require­ments increase. Not to say that there haven’t been improve­ments in data pre­sen­ta­tion, but they’ve been infre­quent and ineffective.

So final­ly I have giv­en up. I bought a small Mole­sk­ine dai­ly plan­ner with one small page per day, ruled, and with a very faint num­ber­ing from eight to twen­ty for the time of day. I had first tried a plan­ner the same size with two pages per week, sev­en days on the left and notes on the right. For the num­ber of appoint­ments I have, the page per week was enough, but using the oppos­ing page for my to-do items for an entire week was frustrating.

I real­ized today that I have a sys­tem that’s work­ing. Before I go into more detail, here’s the impor­tant fact I’ve come face-to-face with: I real­ly don’t have com­pli­cat­ed cal­en­der­ing or orga­ni­za­tion­al needs, as long as I don’t make it com­pli­cat­ed. It’s a lit­tle hum­bling to admit that I’m not the pow­er-bro­ker­ing man of wealth and influ­ence who does­n’t have a full cal­en­dar, but the real­i­ty is that while my days are full, my appoint­ments are a small part of what fills my day.

My needs are sim­ple. I don’t need to write down every detail. My mind is actu­al­ly fair­ly good at retain­ing the infor­ma­tion about where I’m sup­posed to be and what I’m sup­posed to be doing. What I have trou­ble with is remem­ber­ing to remem­ber. So when I write next to the gray 14 in the book, «Bob@Bean» I know that I’m meet­ing Bob at the Bean There Cafe at Stein­er and Waller in San Fran­cis­co, at two pm. Almost every time, I don’t need that to be linked to every bit of per­son­al infor­ma­tion I have about Bob, and I don’t need a link to Google Maps to give me direc­tions. I don’t even need to know which of the sev­er­al peo­ple named Bob I’m meet­ing. I know who I have to meet and where, I just need enough data points to remind me of the con­ver­sa­tion when I agreed to be there or the fact that I’ve been look­ing for­ward to or dread­ing that meet­ing all week, or what­ev­er it is. In Perl it’s a ref­er­ence. In C I think it’s called a pointer. 

Since my needs are sim­ple, so is my sys­tem. The left half of each page (where the faint num­bers are) is reserved for appoint­ments. Where I’ve agreed to be and when. Noth­ing about what I’m doing unless it real­ly seems impor­tant. The right half of the page is my dai­ly to-do list, which for the most part gets filled in first thing in the morn­ing. Each item has to fit, so we’re talk­ing about maybe three or four words, tops. When I com­plete a task, I place a green check­mark over the begin­ning of the line, cov­er­ing the first few let­ters of the word. When I decide not to do some­thing, I cross it out with a sin­gle line in black ink, with a loop at the begin­ning, like the proof­read­er’s mark for strik­ing text. If I decide dur­ing the day that a task should be post­poned to anoth­er day, I use brown ink to make a hooked arrow through the first few let­ters, straight to the left and then mak­ing a U‑turn up and to the right. 

If I don’t fin­ish a task by the end of the day, it stays unmarked and in the fol­low­ing morn­ing I write it anew on the next page. Often there will already be an item or two there, either items I knew in advance should be done that day or else trans­fers from a pre­vi­ous day’s «brown arrow» strike.

While I often have items on a day’s to-do list in advance, it’s always one or two items. The list real­ly gets made in the morn­ing, and I have to make a con­scious choice to car­ry a pre­vi­ous day’s item for­ward to the cur­rent day. With my dig­i­tal to-do lists I always had an ever-expand­ing list of stuff I’m nev­er gonna get done along with the revolv­ing door of new and com­plet­ed tasks. What I do on paper is write down only the tasks I expect to rea­son­ably be able to com­plete that day.

I do add to the list dur­ing the day as new things come up, but so far I haven’t had a prob­lem with run­ning out of space. I always have a few items that get car­ried over to the next day, but that’s fine. In the morn­ing I usu­al­ly car­ry a task over to the cur­rent day, but if I have sev­er­al of the same kind of task I’ll push all but one to days lat­er in the week. As an exam­ple, for the past week I’ve been car­ry­ing for­ward the same three blog post ideas, and none of them was writ­ten. This morn­ing (oh, it’s yes­ter­day morn­ing already, isn’t it?) I looked at that and thought, «there’s no way I’m going to write all three of those today» so I wrote one down for the cur­rent day, and pushed the next for­ward to Wednes­day and Thurs­day. Sure enough, it’s kind of short, but the review of David and Mark Shep­herd’s Park­er ‘51’ got writ­ten and post­ed. There’s noth­ing wrong with car­ry­ing tasks for­ward from day to day to day, but it is a warn­ing sign that I can pay atten­tion to and adjust.

I don’t see myself need­ing to get more gran­u­lar than twen­ty lines of tasks in a day. If I do, it’s going to be with sub­tasks. I have anoth­er note­book for that. When I need to write down project require­ments or descrip­tions of a tech­nique that it occurs to me to try out, or plan out how to accom­plish some­thing, it goes in that note­book, which con­tains every­thing from drafts of blog posts to orga­ni­za­tion­al dia­grams to results of per­for­mance tests to work­ing out feel­ings about per­son­al mat­ters to pseudocode. It’s not a jour­nal or a plan­ner, it’s scratch space for work­ing out how to do the things I’ve decid­ed to do. 

When I com­mit to be some­place, I take my book out, check it, and write down what I commit. 

Impor­tant fact: peo­ple enjoy wait­ing while I check my cal­en­dar. I’ve believed it to be rude to make some­one wait while I fum­ble around with my cal­en­dar, but as I move past what amounts to self-cen­tered fear of oth­ers’ judg­ment I come to under­stand that peo­ple appre­ci­ate that I take the time to com­mit what I’ve said to paper. It’s a sign of respect, so long as I don’t take too long with it, to pause first to check that my time is real­ly avail­able since that means I might do the same the next time, and to put the effort, slight that it may be, into record­ing my plans. To just mum­ble, «yeah, I’ll show up» con­veys a cav­a­lier atti­tude about the plans I make with oth­er people.

Address­es and phone num­bers? Yeah, all that stuff is still dig­i­tal, and I think that’s best. I still don’t want to go back to cross­ing out some­one’s address when they move. Besides, with mod­ern phones (and a lit­tle atten­tion paid to mak­ing sure that the phones I get are com­pat­i­ble with my com­put­er and sync soft­ware) I keep my phone book in my phone, which is where it belongs anyway.

So this is not the sto­ry of con­vert­ing to an all-paper orga­ni­za­tion­al lifestyle, it’s the sto­ry of slow­ly adopt­ing the tools that help and drop­ping the ones that don’t. My two-col­umn-per-day plan­ner sys­tem would be ter­ri­ble for many peo­ple and I don’t pre­tend it’s a sys­tem for oth­ers to imi­tate, except so far as it being a sys­tem that meets my needs.

And to those who may argue that I’ve sim­ply adopt­ed a «lite» ver­sion of GTD, well so be it. What I do is way sim­pler than GTD. I do seem to car­ry a lot of note­books around with me, but I’m OK with that. Am I going to miss click­ing on some­one’s e‑vite and hav­ing the even automag­i­cal­ly pop into my cal­en­dar? Not real­ly. Am I going to miss fill­ing out a form with a full descrip­tion, loca­tion infor­ma­tion, and attendee list for every item that goes into my cal­en­dar? Not even a little.