From the Blog

J.Boye logo I’m so excited to announce my first international speaking engagement at J.Boye 2014 in Aarhus, Denmark on November 5th, 2014.

Time: 15.15-16.00 Wednesday, 5. Nov 2014
Session: So Happy Together (Project Managers and Content Strategists are)
Track: Content Strategy

After fifteen years building CMS driven websites, there is one thing I wish more people were aware of: content matters. Sounds silly right? After all, the ‘C’ in ‘CMS’ stands for, well…Content. However, project stakeholders are often so wrapped up worrying about technical risks or marveling over new designs that content can nearly be forgotten or worse…Treated as an unimportant ‘detail’ to be figured out later.

If you’re a project manager, sponsor, or executive stakeholder, this is a far bigger risk than you may realize. However, all is not lost…In recent years the profession of content strategy has grown in size and skill at a geometric rate, while having an inversely proportional affect on the happiness and success of project managers, who were often left to deal with content considerations in the past.

In this session I’ll share a presentation exploring very practical ways to ensure content isn’t forgotten in your next project. We’ll look at 7 content related risks, and the 7 things you can do to mitigate them. Then we’ll open it up to Q&A and share experience, tips, and tricks on how to be more successful with content strategy and project management in general.

Jake DiMare presenting at J.Boye

Presenting at J.Boye 2014 Philadelphia

I’ve been providing professional digital strategy consulting to small & medium sized businesses, non-profits, and individuals outside of my day job for the last five years. I’ve also worked on many strategy engagements for globally recognized brands at my day job, both as a project manager and an individual contributor to deliverables.

However, this Tuesday will be my last day after almost ten years working as a full-time Digital Project Manager. I officially start my career as a Digital Strategist the following Monday. Now that strategy has become the primary focus of my professional contribution to the world, I thought it would be interesting and productive to take a step back and develop a better understanding of the roots of this area of work.

The goal of this self-directed ‘Hackademic‘ exercise is to develop a deeper understanding of the concepts of traditional business strategy, and look for ways to incorporate this knowledge with a current understanding and approach to digital strategy practice. In other words: What tools do traditional strategists use? What processes and frameworks do they follow? What value do they create? And, most importantly, how can I use traditional business strategy to be more effective Digital Strategist?

Follow the leaders

Information is like food: You are what you consume. For this reason, I really like the idea of beginning with a list of leaders I should be paying attention to. Fortunately, Twitter makes this very easy. Because this list isn’t only about understanding strategy in general, it includes individuals focused on digital strategy and content strategy, such as my current colleague Dave Wieneke who leads the Digital Strategy Practice at ISITE Design, as well as industry leading exemplars such as Perry Hewitt, Chief Digital Officer at Harvard University. This list also includes leading business publications such as the Harvard Business Review and Knowledge@Wharton.

Next I went to Amazon and searched on topics including ‘strategy’ and ‘business strategy’. Under the circumstances I believe Amazon will generate better results than searching on Google because the ‘Customers also bought…’ feature will quickly lead to more value. Also, because I believe someone who wrote a best-selling book on topic as academic as business strategy probably gets it. The other obvious benefit to this approach is immediate access to their books.

Here’s what I’ve come up with:

HBR’s 10 Must Reads on Strategy (including featured article “What Is Strategy?” by Michael E. Porter)
About halfway through this one. So far the big take-away is Michael Porter’s defining article ‘What is Strategy?’. The short version of the answer is: Strategy is the creation of a unique and valuable position, involving a different set of activities.At this point you may be wondering: a different set of activities? Different than what? You’ll need to read the article for the answer to that.

The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do BusinessA couple of people I admire tell me Clayton Christensen is an important compliment and counterpoint to Porter’s position on strategy. This one hasn’t arrived yet so I don’t have much to say about the book but I am captivated by Christensen’s contribution to the conversation on disrupting higher education, including this recent article on NY Times: Business School, Disrupted.

The Strategy Book: How To Think and Act Strategically to Deliver Outstanding Results
Rounding out the initial set of books to read, I would like to go with someone a little younger, who I personally identify with. Max Mckeown is a straight talking, engaging author and speaker on the subject, with an approachable and practical sensibility I would like to emulate. I’m about three quarters of the way through this book and I am really enjoying the modern case studies and introduction to standard strategy tools, such as Porter’s Generic Strategies.

Test your mettle, MOOC style

At every inflection point in my career I’ve relied heavily on books to accelerate my climb up the front side of the learning curve, with good results. But today there is a whole new class of resources available, which I’d be a fool to ignore: Massively Open Online Courses. That’s why I’ve signed up for Coursera’s Foundations of Business Strategy, taught by Professor Michael Lenox of the University of Virginia. It promises I will learn how to analyze an organization’s strategy and make recommendations to improve its value creation by building your strategist’s toolkit. Unlike books, I will have an opportunity to discuss what I’m learning with the instructor and the other students who are attending the course.

Open to discussion

I think another vital step in hacking your way to understanding any subject is to discuss it, a lot. In the past this might have been a bit of a challenge for individuals taking a deep dive on something as unique as strategy, without the benefit of a traditional classroom experience. However, today there’s really no excuse for a lack of community. At any moment I have access to online groups, communities, forums, meetups, and literally thousands of open conversations happening on the social web via Twitter, Facebook, LinkedIN and more.

To that end, I’d like to engage in this conversation: Who are the leading voices in strategy you follow? Please leave your comments here, or connect with me on Twitter and let’s chat.


Agency Oasis

It’s official: After almost 10 years of pushing projects for some of the world’s best, boutique, digital design and development shops, I’m taking a big, bold step. I’ve been retained by Agency Oasis to begin my career as a full time Digital Strategist in their new Los Angeles office, and I couldn’t be more excited! I begin working with them on June 16th here in Boston while Jackie and I sell our condo and plan the move to LA. We plan to be there by Labor Day.

Leaving the team at ISITE Design was not an easy decision. I’ve never learned or grown as much as I have during my time working with Jeff Cram and Dave Wieneke and my teammates at ISITE are the greatest group of people I’ve ever worked with. That said, this decision was about my career and where I see it going in the long-term and Agency Oasis has given me an opportunity I simply could not pass up.

Outside of work, life is equal parts excitement, anticipation, and terror…Selling our home, changing careers, moving to a new city…Any of these things on their own would be incredibly stressful. Mixing them together all at once? This is not an experience for the faint-of-heart. But I’ve got an incredible partner in Jackie and I’ve done this before…With far less experience, resources, and wisdom than I have at my disposal today.

Leaving Boston…Also not an easy choice. These last ten years have been the best of my life because of the friends and community surrounding Jackie and I here in our hometown. It’s hard to quantify something like community…But you know it when you have it…And we do. But I don’t just have a job waiting for me in LA…My brother Max and some of my best friends in the world are in Southern California. Plus, they’ve got year round sailing in LA…And no snow. Life is good.

So now, as I make the leap from helping people build their digital customer experiences right, to helping people build the right digital customer experiences, I leave you with this…All the wisdom I have on digital project management summed up in a GIF reaction tumblr:

Posted by Jake DiMare at 7:23 pm

I just finished Alan Price’s ‘Ready to lead?’ on a flight down to Philly and I recommend it. Very quick and easy to read, it follows the journey of a management consultant experiencing growing pains in his career while making making the leap from manager to leader. Perhaps it’s just the timing for me, but there were a lot of great lessons I strongly identified with.

A couple of key takeaways I want to write down so I remember them better:

  • Don’t take anything for granted. Make decisions based on the best possible information.
  • Invest in people.
  • We’re all making it up as we go along. Don’t take yourself too seriously.
Posted by Jake DiMare at 10:04 am

I will be presenting at the J. Boye Conference on Thursday, May 8. My presentation entitled “Digital Project Management and Content Strategy” will be from 11:15 AM – 12:00 PM.

What: J. Boye 2014

When: May 6-8, 2014 | Presentation 11:15 AM -12:00 PM

WhereThe Hub CityView | 30 South 17th Street United Plaza Philadelphia, PA

Cost: Varies

For more details and to register for the conference please visit the J. Boye website.

J. Boye Logo



I’ve been contemplating a 2013 reflection post for a few days but then I feel embarrassed, which is really strange because I don’t have what most would consider to be a traditional relationship with self-awareness, shame, or regret. The problem is I’ve had a genuinely amazing year. Like, whoa…I didn’t think life could get this good. I do want to celebrate my success…But at a time when so many people are suffering in the world it feels a little weird. (Especially if everyone knew how many hours I spent doing little more than sitting around in my boxer shorts, drooling on myself in front of a video game.)

Flower Petals

Tying the knot
That said, there are some things too important not to commemorate. On the top of that list: Jackie and I got married, and it was like a fairy tale. Our closest friends and family traveled to St. Thomas with us and we tied the knot at what could aptly be described as a castle in the clouds on top of Wintberg Peak.  This video montage of the weekend does a pretty good job of capturing the spirit.

As for my bride…Mrs. DiMare (I love calling her Mrs. DiMare)…Charming, beautiful, and intelligent. These are just a few of the words I use to describe Jackie. But anyone who has met her a single time knows these self-evident truths. What you might not know is she’s also witty, hardworking, patient, inquisitive, open to new experiences, elegant, sophisticated, and one hell of a sailor.

Jackie proved to be a perfect first mate during our week long sailing honeymoon adventure in the Caribbean this year. That may sound trivial but nothing could be further from the truth. Jackie’s considerable skill on the water is the direct result of three years of classes, reading, and practice…All so we could have the honeymoon of my dreams…And I love her all the more for that sacrifice and effort.

As it turns out, She’s also a perfect little fish when it comes to snorkeling and you’ve never seen anyone so adorable in a diving mask.

Mi Famiglia
Whenever I look back at the most important moments in my life, my brother Max is always there with me and my wedding this year was no exception. But he has his own life as well, and I really want to take a moment to reflect on how deeply I admire the hard work and dedication that has led him to his most recent in a string of professional successes: Executive Chef of the Wilshire Restaurant in Santa Monica, CA. In his new role Max is leading a complete restaurant re-branding effort in addition to bringing his considerable talents with food to an entirely new menu. As has been the case in fine dining restaurants in California for the last 15 years, the Wilshire will benefit from the old-school, hard-working leadership that drives Max’s success wherever he goes.

Among those closest to me brother Max isn’t alone in the success department. My friends Brian, Julian, Mike, and Duane, all already successful in their own fields, are all taking risks and making moves that I can’t wait to see pay off. But more important than seeing them be successful in business, I love seeing them be successful with their families and friends. These men, and their lovely wives, are all people I feel immeasurably fortunate to have in my life because they show me every day what it means to be a good person, growing in poise, charity, and understanding.

Although getting married and the honeymoon were the high points of this year, there were many other epic moments and I do want a record so I can look back on this in 20 years and remember…Here are the highlights:

  • Traveled to Hawaii and spent an incredible long weekend with Max and Tommy and met Tommy’s family.
  • Traveled to Seattle and spent a weekend with Tommy and his family.
  • Traveled to Los Angeles and attended Alex Santana’s wedding, spent lots more time with brother Max
  • Got my Blue Belt from Back Bay Gracie Barra while consulting on their digital presence.
  • Made lots of new friends in the local sailing and Jiu Jitsu communities
  • Grew even closer to the friends I’ve had for years
  • Spoke at 3 industry conferences including DrupalCon and The Gilbane Conference
  • Sailed in countless regattas and took honors with the Sparkle Pony team
  • Sailed multiple times on the Cone of Silence, including the overnight Beringer Cup.
  • Got Google Glass and as a result hung out with Dana White and Joe Rogan.
  • Consulted on a new Boston area real-estate startup web business called
  • Continued my pro-bono work with various non-profit organizations
  • Helped my friend Lindsey Walsh build her business Soul Flower Wellness in exchange for countless hours of therapy.

So here’s the deal 2014: You’ve got some big shoes to fill. I’m going to keep working hard and doing my best to be a good man. Keeping things ship shape on my end, so to speak. Here’s to fortune continuing to blow a little wind in my sails…

Posted by Jake DiMare at 5:01 pm

Some people like to jump out of airplanes. Others like to climb mountains or shoot the rapids in a kayak. There are many ways to satisfy the need for adventure in life. I find this need interesting because it hints at the lingering power our evolutionary legacy as hunter gatherers, leading dangerous lives not nearly at the top of the food chain, still has over our lives.

When it comes to my own needs in this category, I like to sail. Sometimes it’s for relaxed adventure, like a sunset ride with friends on Boston Harbor, or a leisurely cruise around the Virgins on a big comfy boat with all the amenities of home. But lately I’m more often chasing the adrenaline. Racing is the easiest way to satisfy this need but my newly developing fetish is a rarely accessed combination of overpowered sportboats and harsh weather conditions.

Last Sunday I was invited to help deliver a pretty special boat from Boston to Plymouth where she’ll be hauled out for the winter. I’ve written about previous experiences on The Cone of Silence on my other blog dedicated to sailing. She’s a Reichel-Pugh Super 30 with a lot of victory in her wake and one hell of a ride. A carbon fiber sled, capable of traveling 20 knots downwind without using a drop of fuel, she does amazing things under a spinnaker but, like many hot dates, she’s also notoriously fickle. Every moment under the kite is no more than a single, breathtaking second from a hair-raising broach.

What’s a broach you ask? Oh yeah, well that’s when the entire boat suddenly veers of course, comes to a dead stop, and slams over sideways, turning the deck almost 90 degrees to the horizon and catapulting anything not tethered to the boat into the ocean. This is a difficult situation to resolve under the best circumstances. Add some harsh weather and a few miles of deep blue sea between you and the shore and it becomes a genuine moment for reflection on life.

The conditions for this trip Sunday were perfect for adrenaline seeking. Winds were 20-25 knots out of the north, air temperature was 45 degrees and raining. Big ocean rollers were following the wind with seas 8-10 feet and a couple of breaking waves over 12 feet. Though the fish-eyed lens on my GoPro does a terrible job of translating the massive, quartering waves in the video that follows, an experienced eye will recognize the combers we were crashing through off-shore in Cape Cod Bay.


In a recent post about jury procedure law blogger Scott Greenfield suggests there are many people who haven’t thought very hard about justice.

“People like justice, though few have given it enough thought to realize what a ridiculously meaningless word it is.”

I agree with the notion that people like justice and I don’t disagree with the second part of his statement. Many people give very little thought to anything besides what’s directly in front of their face. We should strive to resent the masses less over this. Western society is not structured in such a way as to leave people with much time or incentive for contemplation while powerful moneyed interests work very hard to ensure most people are as stupid as possible. Fewer still, who ever show any interest in philosophical inquiry, will have the resources to expand their understanding by connecting with other deep thinkers.

I do, however, have a big problem with Scott’s assertion that the word is without meaning. Though, it’s not surprising to me that an officer of the court system in this country would feel disillusioned about what justice is and isn’t. I have given the concept much reflection, and I have decided there are certainly two versions, with very different meanings:

  • The justice of men, established by corrupt institutions such as governments and churches.
  • Empirical Justice

In the case of the former, I certainly agree, it’s pretty hard to put your finger on meaning. After all, this is the justice established by powerful men with rules crafted specifically to ensure they are able to maintain power with impunity. The kind of justice that encourages stealing land from native inhabitants, building fences around it, and determining it should be for private use only. Maybe throw a few slaves out there for good measure. (By the way, if you think slavery doesn’t still exist…you’re not thinking hard enough.) The kind of justice where millionaire gamblers bring the world economy to it’s knees, while ruining the lives of millions of our fellows, and get by with a slap on the wrist while they are bailed out by poor people. Yet men are thrown in cages for inhaling the smoke of burning weeds.

The other kind of Justice, genuine empirical Justice, is certainly not a current trend. It asserts that all men and women are truly created equal (not the bullshit equality in the Constitution…Real equality) and are therefore owed an equal share of their birthright, the wealth and resources of our combined home, this planet Earth we live on. It asserts we are all due equal treatment from one another…Fairness. I can understand why a man who works in the American version of justice may have lost sight of the word’s true meaning…But I hope humanity never passes a point where it is too late for real Justice to make a comeback.

Empirical Justice* is most closely aligned with John Rawl’s Theory of Justice but, I think, even he gets it wrong. A key tenet to his thinking is that we start with people of different class distinctions who must imagine their circumstances from an original position, that is a superposition in which they do not know if they are rich or poor, and decide what the right system of distribution should be.  Again, this is man deciding what is just.

Empirical Justice is far less complicated: You were born, therefore you have rights to an equal share of the gifts and fair treatment we all deserve. Can you work hard, and, through a market free from coercive power, convince others to give you some part of their birthright? Yes. In fact, this would be a necessary system for progress to occur since some people will undoubtedly still be better at making shoes than plowing fields. But it will be their choice to give up some of their inherited wealth in exchange for time to do nothing, or something else. In modern society we all start with nothing…A status which is the result of the coercive effects of society. Not nature.

So I wonder, what does Justice mean to you? Does it matter?

*Originally read: “In my estimation, empirical Justice…” It was rightfully pointed out that something being ‘in my estimation’ devalues the meaning of empiricism and I therefore edited it.