Writing the ‘Moby Dick’ of MassGOP: 1 year and 250,000 words of activism

It was the year of 1,000 political Facebook posts. Of scores of essays. Of satire and sincerity. Of tweets and comments. Of a fight against the destructive politics of the party’s cast-iron conservative activists that no one thought was a good idea. 2013 was a year where I wrote more words than found in the pages of Moby Dick in an effort to change how the Massachusetts Republican Party thinks about politics.

This essay is about what happened and what can be learned. Those without time for 5,000 words would probably find section 5, “Lessons Learned” the most interesting.


  1. Activism?
  2. Changing How People Think
  3. An Ocean of Words
  4. What Worked Well
  5. Lessons Learned
  6. Did It Work?

1. Activism?

What exactly is “activism” in politics? After all, lots of people love talking about politics, but aren’t activists. The dictionary definition mentions “vigor” for a cause. That sounds better. But talking about politics isn’t enough. You have to spend some time actually trying to change things in your town or at a higher level. Most of the time, people do this by volunteering for a campaign or some kind of organization. But is that valuable? Here in Massachusetts, my Republican Party is quite weak, at only 11% of registered voters. Many Republicans run for office that have no chance of winning. Lots of committees don’t raise much money or don’t spend it wisely. Just about every Republican organization here uses outdated technology and methods. Our state committee is consumed by struggles that are unrelated to electing more Republicans.

So when you have a full time job and two little children, you ask yourself, “What is a good investment of my time? Knocking on doors with inaccurate voter lists, giving a political pitch that won’t be popular – for a candidate who won’t win?” I am not saying there are no good opportunities here. I am saying there are all kinds of activist opportunities that will have zero impact on how our government works. That would be OK if I was 22. But I am 42, and when I do get time away from work and my children, it’s rare and will usually be with my wife.

I thought, “Well, maybe I can do it all on my computer during all the free moments I have between other things.”  As I am a policy wonk, history buff, computer programmer, and experienced writer, I had a lot to say.

But…. what was the goal?

2. Changing How People Think

After the 2012 election defeat, the Republican Party nationally, had discovered it had serious problems: we had moved too far right, we represented the thinking of too few Americans, and our technology had fallen far behind that of the Democrats. Here in MA, things were worse. In addition to local hero Mitt Romney losing, Scott Brown lost his re-election bid, and a new Kennedy commandeered a congressional district he wasn’t even from. In November, I wrote a widely-read article called, “The MassGOP is…dead” that lamented our fate of becoming a regional party. (It was even mentioned in the Boston Globe.) After that, I began thinking about the party’s challenges. I thought to myself, “I know how to address all these problems!” So I decided I would work to help make us a younger, more tolerant, more diverse, tech-savvy party.

In February of 2013, I found out that I wasn’t the only Republican activist who was thinking this way. The NYT Magazine did a long piece about some other people who came to the same conclusion.  I loved the article and more than a dozen people forwarded it to me. The theme of that article brought all the pieces together: we needed to modernize just about everything about the Republican Party so it could be competitive in the year 2013.

However, even knowing what I wanted to do, what was the concrete goal in a non-election year?

I decided it was to inform the thinking of a few hundred Republican activists in Massachusetts so that the right changes would be more likely.

My strategy would be to flood the party with ideas and arguments about how we could change the way we do things. At some point, in their own conversations with others, it would be impossible to just keep doing what we were doing in light of all I had said.

3. An Ocean of Words

Copy of Moby Dick

I will cover what worked below, but here is an accounting of what I did: more than three dozen essays, a few hundred tweets, more than 1,000 Facebook posts, one radio interview, and hundreds of emails and direct messages in social media. A lot of my work was read all over Massachusetts, and a few of the technology articles I did were read all over the country.

I did some rough calculations and I wrote somewhere between 225,000 and 280,000 words. This is on par with the number of words in “Moby Dick”, and half the length of “War and Peace.” My writings in 2013 were, taken together, longer than 95% of all books.

People just didn’t know what to make of it all. They couldn’t believe how much I was saying. I even offered people advice on how they could reduce what they saw of my Facebook postings, and I worked to create private distribution lists so not everyone saw everything all the time. (I worked primarily in Facebook this year, as it is the number one source of how people find political news.)

4. What Worked Well

There were a variety of things I did:

  • Worked to restore the intellectual integrity of the party
  • Fearless and constructive criticism of Republicans
  • Attacked our “grassroots” conservative activists
  • Wrote very long pieces
  • Explained the political technology landscape
  • Accepted people who only liked me a little
  • Found a way to deal with the youngest activists
  • Spoke out against Fox and right-wing media
  • Showed how to argue with the other side, but earn their respect


Worked to restore the intellectual integrity of the party

The political style of Sarah Palin doesn’t work in the most educated state in America, never mind here in Boston. The media is always featuring dumb remarks by Republicans all over the country, whether it is the former Alaska governor herself, comments by Congresswoman Bachmann about the danger of vaccines, and anti-science outbursts from members of the House GOP – who are actually on the science and technology committee. Senator Rubio saying we don’t know how old the Earth is. Global warming is a hoax. Pew Research puts out a poll in December showing that the number of Republicans who believe in the theory of evolution is plummeting. The damage goes on and on and on.


I made a consistent effort to offer scores of posts related to the problem and I encouraged people to take a more intellectual approach to politics and policy. I cited many links of smart thinking about popular issues. I advertised the work of a local free-market think tank, The Pioneer Institute. I also spoke out for the need for people to engage in better forms of argument and to consider points of view other than their own. My point was that of Governor Jindal: we have to stop being the party of the stupid people. And just because the “grassroots” activists love having attractive young women on Fox tell them they’re geniuses – that doesn’t make it so. (More on them later.)

Fearless and constructive criticism of Republicans

One thing we are sorely lacking is good criticism of the party. Thanks to the influence of right-wing media, the only criticism easily found out there is of Republicans who aren’t “conservative enough.” Nobody sees the value in constructive criticism of the methods and ideas of lots of people in the party. We can’t just clap for everything everyone does. The party is in trouble and if we don’t acknowledge mistakes and lost opportunities, we will never reform. People like to think we can improve if everyone just submitted helpful suggestions and never criticized anyone. Nonsense.

Attacked our “grassroots” conservative activists

If there is one thing people really can’t stand about me, it is that I am the first person I know of in the party who decided to attack one of our biggest problems: our “conservative” activists at the “grassroots” level. I put the word conservative in scare quotes because I do not mean people who are part of a long, intellectual tradition of being conservative that goes back to Edmund Burke. I mean the people who think Glenn Beck and other right-wing nut jobs have a lot of good ideas.

The reason that parties are always talking up “the grassroots” is that, traditionally, they have been an asset. These people are the activists who know their communities and can – in theory – help candidates win at the local level. That’s all great – if they really exist at the local level. What’s changed in the past 10-15 years is that lots of these people derive their citizenship from national right-wing media. They watch Fox and think that being a strong Republican is about being Senator Ted Cruz. They develop a political identity that is not only unrelated to Massachusetts, but is offensive to the majority of voters here. They then get involved in Republican politics for the purpose of dragging the party far to the right in the most left-wing state in America. They go online and tear down moderate candidates. They call everyone who doesn’t agree with them a Democrat. They reinforce everything that is wrong with the party. (They still think gay marriage is going to be overturned one day in this state.)

These people are not all of our activists. But they have an outsized influence here and the establishment Republicans have ignored them for too long. They hurt the brand and they relentlessly attack our candidates. Their persistence has even earned them seats on our state committee, which is in a constant state of trench warfare between them and the moderates.

I decided that someone had to take on these bullies and I did it throughout the year, despite cries from naive people who believe in some sort of imagined party unity that the conservative activists don’t actually want. They want heresy trials, not a big tent. (Some of our state committee members even say things like, “The Big Tent didn’t work.”)

But the main reason I fought these people online is that I wanted to show all the normal Republican activists out there that these people and their foolish ideas can and must be defeated. There are ways to use language and argumentation effectively to show that their politics will lead to nothing but more losing. They believe that conservative candidates who lose by huge margins are somehow going to re-ignite the party among the minds of the voters. My famous retort to this in 2013 was: “We cannot lose our way to winning.”

I even had some fun satirizing their politics this year, which no one had tried before. Two pieces I wrote were enjoyed by a lot of people.

The first was an April Fool’s joke: “Right-Wing Groups admit: MA is not conservative”

Here was an excerpt from that short piece:

"The President of the Massachusetts Association of Republican Councils, which calls itself, "The Republican Wing of the Republican Party" said, "We have always advocated that the voters get a clear choice. Unfortunately, they have been grateful for this contrast, and always choose the Democrat." He then went on to address the group's future. "We no longer see the point of trying to influence the Republican party. So, from now on, we will be 'The Republican Wing of the John Birch Society.'"

The head of the Massachusetts Patriots, who was dressed in 18th century clothing made in China, said that he was dismayed to learn that Bostonians today don't really want to live in the America of 1773, and that they actually like government quite a bit. "Our surveys actually show that the reason people in Massachusetts continue to vote for more and more government is because they don't hate it, as our members do. Therefore, we have decided to move to Texas to be part of the secession movement there.”

Only a few weeks later, tired of the calls for a “true conservative” senate candidate, I created an online quiz to test for true conservatism: “New ‘True Conservative’ Candidate Survey”

It had all kinds of funny questions, such as these two on gay rights:

3. Have you ever broken up a gay marriage?

a. No (0 Points)
b. Working on it (5 points)
c. Yes! (25 points)

4. I have personally converted a gay person…

a. To being straight (25 points)
b. To being Republican! (50 points)
c. Neither (0 points)

Wrote very long pieces

As you can see from this piece, I am comfortable writing very long articles. I don’t always do this, but I wanted to make a point that while everyone seeks brevity in a world of people-in-a-rush-on-their-smartphones, that a lot of people like longer pieces and even read them on their devices. There was even some research that came out this year that showed that even young people will read long pieces if they are well written. I think I was probably the first activist to show that you really can succeed with regular, 200-word Facebook posts.

My friends joke about this, as you can see from the post below:

Katie and words

The best example of this was a series of nine long essays – more than 18,000 words in total – in the two weeks before the hotly-contested MassGOP chairman’s election. I wanted to flood the party leaders and activists with all kinds of ideas on tech, organization, an urban agenda, how to reach out to young voters, the advantage of doing a Republican census, and how to do fundraising differently. I prefixed each essay with the word #chair – to encourage people to think big about what a new chairman could use as an agenda. Several members of the SC said they found the content very interesting, even though one of my most respected friends on the SC said they bristled at the condescending and confrontational tone of some of it.

Two samples:

#chair: An Urban Agenda
#chair: Fundraising!

Another unplanned success was a series of very long Facebook posts called “Green Street and Government” – 3,500 words in five Facebook posts about my struggle to clean the graffiti off of the Green Street neighborhood in Jamaica Plain, Boston. Since multiple levels of government had failed to clean the streets, and a friend of mine was moving to JP into her first home, I decided to, over a period of weeks, clean that entire neighborhood. I was there more than 25 mornings cleaning, scraping, and painting, and I had several memorable conversations with the liberal residents and government employees there about the role of government and individual initiative.

These posts were very popular and even some cynical friends of mine were moved at my unique effort to say thanks to a government employee who helped my daughter with her developmental difficulties, all while explaining why private local initiative can make a difference in communities where unionized government employees don’t have the incentive to do the work.

(Unfortunately, those posts are non-public in my Facebook wall. I may turn them into a public article.)

(screenshot of opening of one in the series)

Explained the political technology landscape

Clearly what worked best for me this year was using my technology and writing experience to explain the political technology landscape and the divide between Republicans and Democrats. It is the only activity I engaged in that went way beyond Massachusetts and found a following all over the country.

I wrote at least three pieces that earned a national audience. These were similar, in that each described what the Democrats were doing with technology, and what we should be doing about it. I didn’t take a partisan approach at all, as it was not necessary.

Obama, Romney, and GOP Technology: A Chilling Analysis
A Republican At Netroots Nation
Why the New Organizing Institute is the Left’s New Death Star Aimed at the Republican Party

Also, all year in Facebook, I wrote many posts reviewing interesting political technology, giving tips, and showing what could be done cheaply and easily. This post below was one where I showed interesting things that could be done with maps. It opened a lot of eyes. I advised activists to sign up for free training in mapping. Many did!

Accepted people who only liked me a little

One amusing thing is that lots of my friends don’t like me or the majority of things I say, but still read lots of things. In the hot-or-not world of political commentary, this isn’t common. But because I am a flood of so many ideas and reforms in a party that needs them desperately, lots of people were willing to put up with me because they saw value in a minority of what I had to say – that was not available elsewhere. A fellow activist nicknamed me the “sexpanther” because of this:


I decided this was OK. What mattered most was to get enough quality into what I had to say to keep these people as followers. It didn’t matter that Jeff doesn’t like me that much. He matters in the party – more than I do – and makes the GOP brand look great in media appearances. He, like me, understands that our methods of fundraising and organizing do not work and we need to make the case for reforms there. (We are also both articulate defenders of capitalism in a party that has forgotten how to defend it.) The 30% we agree on would, if realized, totally change our fortunes here in MA, and that’s all that matters.

Found a way to deal with the youngest activists

One of the interesting dynamics of the new world of online politics is that it is heavily skewed toward the young, where traditional politics was the opposite. This isn’t a bad thing, but the newfound freedom of 21-year-olds unleashing their confidence and know-it-all assessments upon older people can be annoying. This doesn’t have to be a bad thing when they really are in possession of uncomfortable truths. (The best example is them telling older party leaders to get real about accepting gay marriage.) But it is often grating and insulting how they make crazy pronouncements and tag party leaders.

It’s really easy to just unfriend, block, or outright ignore them. Many older party leaders do. However, I have made a special effort to be patient and remember that I used to be like them 20 years ago. We need them to develop their skills and knowledge. They need mentoring, even from people they don’t always like. They have been born into an insane partisan era where politicians can’t solve problems and we must take the time to make sure they don’t believe this is normal.

It isn’t that I tolerate everything, or comment on all they say, or make an effort to talk to all of them. But I am willing to put up with a lot more in the name of them becoming better political citizens before they gain power. I believe this has worked out better than just ignoring them.

Spoke out against Fox and right-wing media

Another theme of my activism is to point out that you are what you eat, and a diet of right-wing media is bad for you, and the party. I can’t think of a worse problem we have as activists that gets so little attention. Consuming the attitude, misinformation, style, and words of right-wing media makes you a less effective advocate for our beliefs, and far more likely you will behave in a way that offends people.

Even in MA, we have right-wing commentators who damage the brand constantly. Howie Carr, in a piece just several weeks ago, lamented the fact that we lose statewide races because of big losses in the cities, which he referred to as “the EBT crowd.” Good grief Charlie Brown! Thinking of urban voters as just a bunch of welfare cases is how we got into this demographic mess to begin with. Yet people like him are invited to speak at various events as if they are political sages.

I advocated all year that people need to change their information diet to include more vitamins and less empty calories. I don’t know if I got through to people on this. I do think many of them will be less likely to praise local right-wing pundits in light of my constant indictments. Also, hundreds of my Facebook postings were articles meant to be part of a healthy information diet – especially in areas that the party doesn’t talk about, like how to deal with fading social mobility and increasing income inequality. (It’s my way or Senator Warren’s – should be an easy choice.)

Showed how to argue, but earn the respect of opponents

Right-wing media trains Republicans to fight the other side, never concede anything, and don’t bother trying to gain respect from your opponents as they are wrong about everything. In a state where almost every Republican candidate must win over independent voters by huge margins, this is exactly the wrong approach.

I rarely criticize the Democrats in harsh ways. I don’t engage in the battle against “liberals” as they don’t listen to Republicans and there is no value in these online clashes, especially on the Twitter #mapoli tag. Don’t get me wrong, I will attack some absurdities with righteous fury if I think that an independent voter would agree with me entirely. A good example was when I attacked the Boston Public School system’s decision to give free lunches to all kids, even if their parents were rich. And I really attacked Beacon Hill over the technology tax, of course!

But, in general, I treat Democrats with respect because it makes me more effective as an advocate, because it is antidote for our awful partisan times, and because I have many respected friends who are Democrats. There were some high-profile cases this year of the other side showing respect for me. Some examples: One of the most frequent contributors to Blue Mass Group sent me a private email in February praising me for my views on technology and my respectful tone toward the Democrats. My piece about Netroots Nation resulted in me being invited on a national radio program by a board member of the foundation to discuss the conference and politics. The communications director of NOI complimented me on Twitter for my piece on Rootscamp (NOI’s conference).


Another benefit of not being a partisan maniac is the ability to learn things from non-Republicans. I went to a technology show in Silicon Valley in the summer of 2013, and was introduced to key members of President Obama’s technology team, who were there to talk about their excellent engineering work. The introduction was from a liberal Democrat friend of high status who respects my technical skills and my politics. It would not have happened otherwise, and we all had a fun and fruitful conversation talking shop about political technology.

Also, in December, I decided to write some comments on the increasingly popular Massachusetts political blog, MassPoliProfs. I have tried to be constructive and show respect in what I write, and I haven’t tried to take them on for their opposing views right away, as it is important to build trust before having any disagreements. (Other Republican activists have been very confrontational and I don’t see anything that has come out of it. The professors will probably not entertain any new ideas from that kind of approach.) A week ago, one of the three contributors, Professor Duquette wrote,

“I also want to take this opportunity to thank you for you willingness to read and give thoughtful feedback to our commentary here at Masspoliticsprofs. Your comments always help restore my faith in the possibility of civil and intelligent dialogue in venues such as this.”

In future arguments about the issues, I am sure we will be able to have a spirited debate that will not only be more valuable for others to watch, but one in which both sides are willing to admit they are wrong if warranted. That won’t happen without respect.

5. Lessons Learned

Here is my best advice that came from what I did this year:

You need to calibrate your activism for the present. Yes, there are things about politics that have been the same since the time of Aristotle. But things do change, and Republicans who cling to the bromides of the 1980s will be ineffective.

If you aren’t a great typist, get a book or take an online class in typing. I’m serious. Few things will give you a greater productivity boost than that. When you are in a real-time online discussion and can type twice as fast as your opponent, you will have a real advantage in getting ideas and arguments out without losing tempo.

There is no effective advocacy where everyone likes you. Work that matters must change the status quo and there are many beneficiaries and protectors of how things are. This is not the same thing to say it is a good thing, on its own, to be disliked. It is not.

– The people who work at Facebook say something that most people don’t know: everyone vastly underestimates how many people see their content. Don’t assume a lack of feedback means no one is listening. You probably have supporters who love what you are saying but don’t want to publicly endorse it. Eventually, they will tell you through private channels. (Many have told me that can’t afford to “like” my comments in public.)

– Fight against your opponents online not to win, but to show all the people watching how to fight effectively.

–  How you use criticism and praise is tremendously important: you must learn to praise people with sincerity and criticize people with precision. It is better to criticize people more narrowly on firmer ground than more broadly on weaker ground. Also, most people are not good at giving thoughtful and humble compliments, and should spend time practicing it. (Don’t know what I mean? Browse greeting cards at the store and try to figure out how to get that kind of eloquence into your social media praise.)

(An example of careful criticism)

Your adversaries will hold you to a much higher standard of accuracy and fairness than they do their allies. Accept it, don’t gripe about it, and meet that standard, every time.

Timing of social media posts is crucial, but that is not the same thing as being first.

Effective use of language and images is so important that you must continuously and separately study these techniques. Coming up with the right words is the difference between your ideas being ignored and your ideas going viral.
(example of a slogan I came up with that was clever enough that many people used it)

– Your own media diet matters. You have to stay out of the political ghettos and echo chambers. You must bring the wisdom that is outside of politics into politics, not spread around cliches that already exist there.

Always pretend that every person you are writing about is in the room watching you type, even if you dislike what they are doing. Use formal titles on first reference for all people of status, no matter how awkward that feels. (That technique will change how you treat them.)

– While it often feels important to respond to everything that is said about you, it is sometimes better to just let things go unanswered.

– It matters a great deal which things you do privately, what you do in small groups, and what you do out in public. Not all conversations are best held in the public square. Though all conversations should eventually lead to something presented in the public square.

Try to be fair. I remember once in the senate primary that one of our grassroots activists said that Mr. Sullivan was the best general-election candidate. Ridiculous, and I said so. In fact, I offered a $50 reward to anyone who could find a neutral observer to say anything like that. My friend Paul Ferro, who is among the best of the social conservatives here, found a citation that didn’t exactly meet my test, but was close enough that I felt he should be rewarded. I sent him $50.


6. Did It Work?

I think so. (But that isn’t the same thing as saying every word was needed.)

I know of many examples of people throughout the party taking my ideas – especially in tech – and using them. I also think there is now a greater consensus that the party needs to do organizing and fundraising in a different way. A few of my ideas from the #chair essays have already started happening. I also think that when someone decides to move in the direction of my ideas – even if they came up with them independently – more people “get it” now and are more enthusiastic about participating. As for the too-conservative activists who only want Tea-Party style candidates, they haven’t changed at all – but I think the moderate elements in the party are better-equipped to deal with them, thanks to much of the language I have put out there about what the problem is, why it hurts us, and how to deal with it.

What will I do in now? I don’t know. It will be different and I will have a lot less to say. That will probably make everyone breathe a sigh of relief. 🙂

Happy New Year! May we be a younger, more tolerant, more diverse, more tech-savvy party in 2014.

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