I love milestones.  Times of year that mark change and give you a chance to pause and reset. I think that’s part of why I had such a hard time living in California during college, and why I appreciated the seasons so much when I moved back east.  They provide a very natural rhythm. The time between Christmas and New Years is one of my favorite transition times.  I love the fact that nearly everyone is on vacation, so everything slows down.  In the past I have usually stayed at work during that week and used the time to catch up on everything. With new years, I love the opportunity to pause, take stock of everything, get organized, and get ready to hit the ground running in the new year. For me, this is my “spring cleaning”, more than anything I do in the spring.   Here’s what I’m working towards this week to get cleaned up and ready for 2013:

• Resetting email. I got crushed on email in the last month, and have a lot of open threads (I apologize to anyone I owe an email to).  I am working towards inbox zero by New Years.

• Rebooting my blog — as of yesterday, I’ve merged my blog and my tumblog into one.  I’ve moved my blog archives dating back to 2006 to the Wayback Archive, and am doing everything on Tumblr now.  Fewer things; more focus.

• Mundane things around the house — Yesterday Cescalouise and I cleaned out our basement, and I organized my mess of a closet.  Both feel super good to have done, and help create an overall sense of healthiness.

• Going to get a haircut :)

And as always happens, I’m using this time to get inspired about 2013.  I’ve been collecting some quotes that are getting me fired up.  

It's hard to find the right balance when bringing technology into our lives.  I do think lots of us suffer from some form of internet / social media addiction, and it's getting easier and easier every day to bring all of that with us everywhere we go. This will only continue to accelerate (and I don't even have Google Glass yet).

A few weeks ago, I went to a discussion at the New York Public Library for Steven Johnson's new book -- for the event, Steven's "debate" opponent was Sherry Turkle, author of "Alone Together: Why We Expect More From Technology and Less From Each Other". The thesis of Sherry's book is essentially that we are all addicted to our phones, and that we're trading away our real-world connections for distant digital connections.  She has spent countless hours interviewing teenagers, observing moms and dads in the playground (with their faces stuffed into their iphones, of course), etc.  And basically came away with some troubling, if unsurprising, results.

I am not terrified by all this, but I do think we're at a moment now where we are still forming our cultural norms around all of this, and it will take a while.

For instance, Frannie and I have a rule of no screens in bed (that includes TV) -- it just seems like the bedroom should be a place to unplug, slow down, and relax.  But over the past few days while she's been away, I've been breaking the rule.  On Sunday night, I blew through my email backlog on my laptop (woo!), and on Monday night I followed #Sandy via Twitter on my phone.

Of course, this sparked an argument discussion last night when I continued to break our rule by bringing my laptop to bed to write "one last email".  To make matters worse (better?) I posted a snap poll to twitter to see what people thought about this particular nuance of digital culture. The results were mixed:

Some great gems in there.

I do think that thinking about this in terms of addiction seems about right -- we have this thing with really powerful social pulls drawing us in, and we need to make sure we understand how to live in moderation. I might even argue that the addictive strength of the internet and social media is stronger than that of alcohol or other drugs; at least the social aspect of that addiction. i.e., I may feel some social pressure to drink more than I should, but it's not coming at me 24x7 from hundreds of friends, thousands of acquaintances, and millions of others.

So, this is something we'll have to keep figuring out.

I've always thought of tennis as perhaps the most difficult of sports.  It's like hitting a baseball, but while you're running, and with 90% of the addressable target area out of bounds (in the net, outside the lines, etc).  To top that off, you're a team of one, battling yourself, inside your head.  So it's really easy to get frustrated and implode when things start heading south. I played a lot of tennis as a kid, but basically haven't played at all for the past 15 years or so, until recently.  Over the past few weeks, I've picked it back up and gotten really into it, and it's been really fun and also a challenge.  My playing style has always been aggressive and error-prone.  I have (IM*H*O) beautiful strokes, but go for a lot of winners and tend to make a lot of unforced errors.  Historically, I often lose to players who can simply get the ball back and put me in a position to beat myself.  On serve: it's aces or double faults.  You get the idea. Clearly, this is a frustrating way to play, and to be.  And it puts me into a position to love and hate tennis at the same time, and to get really down on myself for not living up to what I see as my potential. Recently though, I've been working on a way to address this.  I've been going into playing tennis expecting it to be frustrating, and knowing that overcoming that frustration is part of the challenge, and part of the fun.  Seems like a subtle difference, but it's really been game-changing for me. If I go in expecting to have a mental challenge -- and knowing that I'll get through it -- rather than being surprised when it happens, it's somehow way easier to deal with.  It becomes part of improving my game, just like working on my strokes, and it generally helps me relax and get loose, rather than get frustrated and tight. This may seem like a stretch, but it reminds me of what a good friend once said about eating magic mushrooms: that it's a challenge and an adventure;  that he fully expected to get freaked out and scared, but working his way through that, and getting over it, is part of what he liked about it.  Seems crazy in some ways, but I get it.  So, I guess I'm saying playing tennis is kind of like tripping on mushrooms. And of course, it's the same with being an entrepreneur.  Apparently Reid Hoffman characterized entrepreneurship as "throwing yourself off a cliff and building a plane on the way down", which feels right.  And my friend Nick has described the roller-coaster ride of entrepreneurship -- one day you feel like you're killing it and you've got the whole world figured out, and (literally) the next day, you can feel like you're 100% wrong and totally screwed.  That's for real -- in the past, I've felt it on something like 8-hour cycles -- and it's part of the reason why co-founder chemistry is so important; to help you weather that storm. In all of these cases, I think the trick is not letting yourself feel like all is lost -- expecting there to be (sizable) bumps, but understanding that of course there are, and that's part of the challenge and part of the fun.  Somehow, thinking about it that way really changes things for me.  

As I write this, I'm sitting on the platform at the Back Bay Amtrak station in Boston, waiting for the train to New York. At 9am (6 minutes ago), I got a text message prompting me to write a blog post today. It said "Get your blog on!  It's a good thing".  The text message, of course, was sent to my by myself.  I've got a little robot in the cloud whose job it is to help me be a better person.  In this case, it's helping me be more consistent and less stressed about writing here, on this blog. The service I'm using is called IFTTT (If this, then that), and it's a very simple way of wiring together events from across various web services ("channels" in their parlance).  In this case, I have the SMS channel triggered to send me a text every day at 9am.  I also have a 10pm text which prompts me to write to my journal (that one says: "Take a 5 min break and post to brain [the name of my journal blog].  You'll thank me later."  Last night when I got that text, I said to myself: "Self, you're right -- I will thank you later".  And I wrote the post.  And here I am this morning. I've been thinking a lot recently about the difference between being organized vs. being disciplined, and I've been putting a lot of energy into increasing my discipline factor.  Who knows if this will end up sticking, but I hope it will.  At this point, it surely sounds like another exercise in yak-shaving, and knowing myself I'll let that stand as a possibility. But I really do like the idea that it's possible to get more effective by doing less yourself and recruiting more help from others (in this case, from robots).  And in this particular case, there's something particularly nice about being able to make up the wording yourself, knowing exactly what will push your own buttons and get you motivated. I really like IFTTT and will surely find more ways to use it.  There are other services out there too, like Happiness Engines and I'm sure many more.  At this point, I prefer the flexibility and straightforwardness over IFTTT to the slickness of Happiness Engines, but I'm looking forward to seeing where both go, and to experimenting w/ other ways to recruit robots to the cause.

I've been thinking a lot about what it means to invest lately.  I'm not just talking about investing money, in savings or stocks or whatever; I mean investing in a broader sense, in yourself and in everything you do. I am without question an urgency addict -- as a general rule, I procrastinate, let things build up, and then power through with a burst of adrenaline when it gets down to the wire.  This also means, generally, that I'm bad at medium-term planning.  I often rely on my ability to "just figure things out" when I need to, and most of the time it works out.  Lucky for me, I haven't yet had a total blow up disaster, but I definitely flirt with it. More and more, I've been thinking about this approach as a kind of personal debt.  Every time I do something at the last minute, whether it's a presentation, a document, or plans for a trip, I'm burning reserves (cash, time, sleep, social capital) and often going into the red.  While it may work most or all of the time, it's not sustainable and it's not a good way of using resources. Credit cards bail you out when you're over extended and need to get by at the last minute.  Personal and planning debt is the same way. Conversely, investing in yourself, your plans, your friends & relationships, and your health is a longer-term proposition. It takes planning and discipline, and it doesn't pay off right away.  But investing is about building a strong base.  And it's about dedicating resources (time, thought, money) in things that are important, matter in the long run, and will grow into something even more valuable -- to yourself, to your friends, business associates and family. There are all kinds of good reasons for going into debt -- financial or personal -- whether its borrowing against a house or an education, using loans & credit cards to get through a tough time, or getting way backlogged on your work, your email, your exercise, or your family time. What I'm talking about is a general mindset of: "what am I spending my time doing -- am I making an investment right now, or am I burning capital right now -- and if I'm burning capital, am I beyond my reserves?" With that in mind, my new mantra is  "Always Be Investing" (imagining Alec Baldwin coaching me at it).

Last week, I mentioned an article called The Making of the Corporate Athlete (originally published in 2001 in the Harvard Business Review).  If you haven't read it, you should -- it's a short read.  Long story short: successful athletes take a "whole body" approach to optimizing their performance, and other kinds of professionals could benefit from doing the same -- in other words, willpower and brainpower alone are not enough. One idea that stuck with me is the importance of rituals as a training activity.  In each case study, the authors, who are acting as consultants (or therapists) for corporate clients, make a point of establishing "positive rituals" to help train their clients out of old, unhealthy habits, and turn them into corporate (and personal) superstars.  According to the diagram below, rituals are the hand-holds for ascending the "High Performance Pyramid".

I particularly like the idea that rituals create an explicit opportunity for recharging:

Our own work has demonstrated that effective energy management has two key components. The first is the rhythmic movement between energy expenditure (stress) and energy renewal (recovery), which we term “oscillation.” In the living laboratory of sports, we learned that the real enemy of high performance is not stress, which, paradoxical as it may seem, is actually the stimulus for growth. Rather, the problem is the absence of disciplined, intermittent recovery. Chronic stress without recovery depletes energy reserves, leads to burnout and breakdown, and ultimately undermines performance. Rituals that promote oscillation – rhythmic stress and recovery – are the second component of high performance. Repeated regularly, these highly precise, consciously developed routines become automatic over time.

and that they are an important technique for stepping off the daily grind treadmill:

The inclination for busy executives is to live in a perpetual state of triage, doing whatever seems most immediately pressing while losing sight of any bigger picture. Rituals that give people the opportunity to pause and look inside include meditation, journal writing, prayer, and service to others. Each of these activities can also serve as a source of recovery - a way to break the linearity of relentless goal-oriented activity.

This makes a lot of sense to me, and I've started to apply it to my own life.  For instance, blogging here helps me clear my head and recharge, but it's hard for me to find time or space to do it during the regular day-to-day (plus, that's what Tumblr is for).  But I've found that firing up ScribeFire first thing on the mornings when I Amtrak it from Boston to NYC works - so that's what I'm trying to do now each week. Another example: Theo and I have been doing swim lessons together every Saturday morning for the past few months, and that time has quickly become my favorite part of the week.  Thinking about it a bit, I realized that, besides the fact that he and I are spending dedicated time together, there's something particularly comforting and recharging about that time being blocked off from the rest of the week -- no email, no phones, etc -- and the fact that it is the same time and day somehow adds to that recharging ability. And then of course there is my hero-blogger Fred Wilson, whose pattern of writing is entirely ritual-oriented (1 blog post per day, ~3 tumbls a day, weekly series, etc.).  I am clearly inspired by the way Fred writes and you can see that reflected in how my own online presence is set up (and probably even in how I write). At a certain point, rituals can become traditions, which take on a different kind of long-term social value.  For example, my father in law has been having lunch with his friend Bob every Saturday for the last 40 years (maybe longer).  As long as my wife can remember, her dad slipped out for an hour every Saturday.  He also recently told me that his father took him out for breakfast every Sunday when he was a kid.  There is something really powerful about the connections that these ritual/traditions create.  It can be hard to keep them in place, but I suppose that's what makes them so meaningful if you can. So, at risk of caving to my own OCD tendencies and immediately hyper ritualizing my entire life, I will say that I see the value in integrating these ideas.  On a personal level, and also on a company / team level. For instance, at OpenPlans, for the past year or so I have been super focused on external issues -- raising money, developing business, making partnerships, etc. -- to the point where now that those investments are paying off, I really want to refocus on making sure our internal operations are healthy. To some extent, I think that means working to institute some positive rituals into our work week (without digressing into toxic meetings). So, there you have it: this week's personal self-help installment, brought to you by a nice window seat on the Amtrak Acela, somewhere in eastern Connecticut.  See you next week.

Last month, I attended the Massachusetts Technology Leadership Council's annual unconference.  My favorite session, by far, was Bill Warner's "Building a Startup from the Heart". I found Bill's approach to be inspiring, and immediately went home to incorporate his ideas into some OpenPlans materials that I'd been working on (e.g., a new page on our website describing our transportation business -- you can now see Bill's "beliefs / people / intentions" pattern loosely reflected). I won't try to reiterate Bill's big ideas, because that has been done (here is a good overview, and here's a video of Bill's Ted X talk).  Both are worth a read / watch. Since then, one takeaway has really stuck with me: the idea of speaking from the heart. A fairly large part of my job is talking & writing about what we do; to funders, clients, partners, students, the press, etc.  I believe in our mission, and think that we have done and continue to do good work.  At this point, I can speak pretty easily about it, and do my best to weave our complex mission and activities into a (reasonably) cohesive story. But I realized that I don't always speak from the heart as much as I should or could.  It's hard to describe, but it's a difference you can feel -- when I think of speaking from the heart, I feel the focus moving from my head down to my belly.  To the place where you just know the things you're talking about, and why they're important.  You aren't  nervous or worried about getting it right.  To use Bill's language, speaking from the heart brings you back to feeling the connection your people, your beliefs, and your intentions (the feeling reminds me of the notion of the Ideal Performance State, as described in The Making of the Corporate Athlete which is also worth a read). When I think back on the times when I haven't been happy with how I've performed in a speaking gig, I can usually trace it back to being too much in my head and not enough in my heart/belly.  For instance, in September we announced Civic Commons at the Gov 2.0 Summit.  I did a small part of of the announcement, which went fine, but I didn't consider it an A+ performance (and got endless shit from Clay Johnson about it).  According to my wife, who watched the video (I didn't), it was a B; not completely embarrassing, but not particularly great either.  Fine.  Afterward, I realized that I had gotten too far into the weeds -- was too much in my head and not enough in my heart.  Tired, uninspired.  If I were to do it over, I would have focused on the core ideas about why we believed the project was important and why we were part of it. Speaking from the heart gives you energy and confidence.  It gets you back to the real reason why you're involved and why you care.  It's powerful and easy at the same time.  It's an idea that I will keep with me.  

I love seeing people write to their future selves. Here's a note I came across in my very own inbox today, no doubt jotted down on my iPhone while I was half-drunk at a party.

Drake.

Neon Indian

Groove shark - friends playlist

   Darius.  Radius radius

Brother

"Radius radius" is my favorite part.  I can't wait to discover what it means, after I do a little googling.

This week, we're on vacation in Cape Cod with my wife's family.  They've been renting the same tiny cabin by the beach for the past 35 years, and coming here is pretty much the highlight of our summer each year.  Last summer, we brought Theo here when he was just three weeks old.  This morning, he and I took a walk along the harbor in Provincetown at low tide -- he thinks of each beached boat as a giant bucket, just waiting to be filled with sand. The problem is, whenever we're on vacation, I have a hard time finding the right balance between "unplugging" and staying engaged with the real world.  One the one hand, I want to remain connected with work and friends, on the other, I just want to tune out, relax, and be with the people I'm with.  Inevitably, I end up fighting the struggle each day, carving out some time for the important stuff at work, and forcing myself (with limited success) not to stress about it too much the rest of the time.  It's tough, and to some extent I feel like I achieve the worst of both worlds: neither able to fully enjoy my break, nor be fully present for important happenings at the office. This has become more of an issue as technology has evolved.  Here at the cabin there's never been any phone or TV.  Then there were cell phones.  Next, internet down the road at the town library. Then, iPhone and blackberries.  Now, this year we have a mobile broadband connection for our laptops, so we're as connected as we can be.  For certain things, it's great: we watched the World Cup final online last weekend, and yesterday my father-in-law did an interview via Skype, which saved him a day-long trip up to Maine.  But, work email and things to do are now within arms reach at all times. I suppose the vacation case is just a microcosm of the larger question of how to balance real-world face time with online time.  Fred Wilson, one of my favorite bloggers, covers this topic frequently, and I'm really amazed the extent to which he's able to stay engaged with the networked world without driving his family crazy.  In our case, the family is only semi-digitally integrated; it's just not part of our culture to always be connected.  Maybe getting an iPad would push that culture change in a good way. Lastly, I think it also comes back to information fitness -- using online (all?) time to do the most important and productive things, and not just consume endlessly as you might in a less online constrained environment.  And of course, one of these days I'll be able to plan ahead enough so that everything is under control at the office and I don't have to worry about anything.  But I'm sure if I did that, I'd find reasons to plug back in...

This morning, I drove from Boston to Cape Cod, alone with my thoughts except for Theo sleeping in the back seat.  Once we were out of the city and smoothly on the highway, I got to thinking about work, and things really started clicking.  I found myself reaching for my iPhone to record voice memos about once every minute.  I may have even cracked an important nut; we'll see. I can't remember where, but I once heard the phrase the optimism of the traveler, and the idea has really stuck with me.  For me, this manifests itself in the fit of ideastorming I usually find myself in whenever I'm on a plane or train (and sometimes when I'm in a car).  Some of my most creative and productive times have been in these situations.  And it's not just about volume of ideas -- there's a different sort of excitement and hopefulness that happens during these times. So, what is it about traveling that produces such excitement? Is it being away from the internet, and therefore being forced to digest some ideas and not just consume at will?  Or maybe it's less about attention, and more about being in that middle place between destinations, where anything is possible? Whatever it is, it's really great.  Of course, the hard part is putting those ideas into motion once you're feet are back on the ground... // Photo by Tjeerd on Flickr