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Part 2: The Contest?!?

This is part two of a continuing series in which I pull back the curtain and reveal some of the wackiness, triumph, tragedy, and a whole lot of ‘huh?” as I make a frightening and risky career change.Without further ado, the second part of “The Teacher, Who Thinks He’s a Fraud/May Be/Probably Isn’t, And The Magical Tale of Him Putting His Ass Out There While Risking a Pretty Damn Happy Life So Far”:

Whenever trying to make a new connection, sell something, or get attention of any kind it is vital to have a story that resonates. Even better if your tale is memorable AND can be told in a minute or two.

This is basically the idea behind “elevator pitches,” stories that entrepreneurs and start-up companies use to woo investors, board members, or co-founders. The pitch is quick and compelling, and aims to convince that an idea is viable, unique, and quite possibly, THE NEXT BIG THING!!!

My personal elevator pitch, as I try to convince someone to hire me, sans experience and all, has continued to be, “Yes, I don’t have a Marketing Degree/MBA/Certificate of Completion from the University of Phoenix… Buuuut, I do sales/marketing/business leadership everyday as I trick teenage boys not only into reading Shakespeare, but also into actually, possibly enjoying it.”

This works sometimes, most of the time, not so much.

So, I have another story that wins folks over and convinces them that maybe, just maybe, I may be a risk worth taking.

This story is called “The Contest,” and it is tale full of stress-filled Google Chrome re-freshes, LinkedIn connection pestering, and twitter twit-tweeting.

The tale begins with a somewhat risky, yet pretty innocuous comment left on the blog of Tim Ferris (who is a guru of many things, but mainly, the number 4).  Ferriss had handed over his blog for the day to LinkedIn founder Reid Hoffman and blogger Ben Casnocha to discuss risk, career change, and the idea that one could apply entrepreneurship ideologies to one’s own life. Hoffman and Cashnocha were promoting their co-authored book, The Startup of You, and were offering mentorship and a whole suite of prizes to whomever them deemed to be taking the biggest career risk.

My comment, among the almost six-hundred left on the site, told what I thought were the riskiest aspects of leaving my teaching career: loss of ‘stability’, passing up an opportunity for my kids to get a very expensive private school education (think what you paid for college and add $10,000 to $5,000), and the ability to pay bills, a mortgage, and two car payments.

I left my comment, didn’t think much of it, and moved on.
Then, in late August, I get this email:

Hi Dennis,

Thanks for your comment on the 4HWW blog on risk.

We’d like to feature your story as one of the top 3 comments from that post — can we include your photo (from LinkedIn profile or otherwise) alongside posting your comment?

Let me know ASAP.

Thanks,

Ben Casnocha
Co-author, Start-Up of You

I mean, pretty cool, right?

What I hadn’t realized was that I wasn’t just one of a “Final Three”, but was involved in a battle to the death for … what again, oh yeah, a great mentorship opportunity! (Exclamation points have lost all power, trust me, I teach English, and my students have no idea what the word emotion means never mind trying to have them identify it in writing!)

It was in the next month that I realized the complete and total addictive nature of the internet and social media, and, probably annoyed a whole bunch of people.

Next Week (Maybe): Part 2 of Part 2 (HA!) Aptly titled, “The Contest?!? – Part II”

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Something I Keep Coming Back To

The words of Seth Godin, marketing maven and though provoker:

Who goes first?

Initiating a project, a blog, a wikipedia article, a family journey–these are things that don’t come naturally to many people. The challenge is in initiating something even when you’re not putatively in charge. Not enough people believe they are capable of productive initiative.

At the same time, almost all people believe they are capable of editing, giving feedback or merely criticizing.

So finding people to fix your typos is easy.

I don’t think the shortage of artists has much to do with the innate ability to create or initiate. I think it has to do with believing that it’s possible and acceptable for you to do it. We’ve only had these particular doors open wide for a decade or so, and most people have been brainwashed into believing that their job is to copyedit the world, not to design it.

That used to be your job. It’s not, not anymore. You go first.

 

I read this a couple of weeks ago and continue to put myself into the category of never “believing” that I am capable of “productive initiative.” Two weeks ago I posted a “Part I” of an adventure I am in the midst of and I feel awful that “Part II” is still sitting in front of me, almost complete. Creating art is not easy and I am sooo impressed with people like Seth, and Leo Babuata who continually churn out new and fresh ideas. Yeah, some of the bits they post online have been sitting around for a lull in creativity to find their place in the world, but they are truly “shipping” their wares.

Yeah, I have a crazy busy life, but, (and maybe you feel the same way too) I really, REALLY don’t want to keep “copyediting” the world.

Designing it sounds so much more fun.

 


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How I Got Here and Where I Am Going – Part I

As 2013 is beginning to unfold, I continue to be excited about what this year holds. I have a lot on the line in 2013, you might say that all of my chips are on the table at this point. For the next few weeks, I am going to share some of the ups and downs that I experienced in 2012 while looking for a new career, as well as the most recent developments in this ongoing story.

Without further ado, I present “The English Teacher Risking Life and (Really Just) Career Stability Because He Has a Hankering to Add Some Meaning to His Life,” in multiple parts.  Here is Part I:

Sitting at my desk, dazed by boredom, sweating because the heater is inexplicably on as the thermometer toes the 85º line, I am generally pleased as my students engage and share ideas to test each other’s creativity.  So, I decide to open my email.  Here’s what I find:

“DB,
Please return your desks to their original rows and out of the non-standard
circle you have been using for the past few days. Thanks.
August Pierce,
Business Manager.”

As a teacher, when you find something that actually works and makes your students more productive and happy, you feel like a champion among educators.  And yet, my good, and pretty widely used idea, in this instance, gets crushed.

Looking back, this was the push that I had needed for a long time.

Although I had been considering a career change for awhile, this call to cease innovating was the last straw.  It was time to make a pivot; to change careers.  This was a very risky proposition seeing that I had all the job security anyone could ever want, as well as the opportunity for my kids to get a very expensive education for free.

What I didn’t count on was how difficult such a transition would be.  I have a degree from a pretty well-regarded college, I have years of teaching experience, and I am damn close to earning a Master’s degree from Harvard.  And yet, the pivot, which I thought would be smooth, has been more like a rusty door hinge; meaning that years of built up corrosion (lack of “experience”) have caused this change of career to creak slowly and barely budge.

Here’s a sample of some of the early frustrations that come while living life in the Rusty Door Hinge:

-I showed up to a job interview wearing my standard “Private School Uniform”,  blue blazer, khakis, scuffed brown shoes (I had removed my tie on advice from a friend who worked at the company and mentioned that they had a very casual workplace attire policy). It turns out that this was even overdoing it; by not wearing jeans, at an interview for a sales job at a suburbia-based “online development platform” company, I had inadvertantly signaled that I was not only a square, but I also unexpectedly projected an air of smug superiority. The interview actually was very pleasant, I think. I didn’t end up getting the job, but I did have a really long conversation about high school football in the middle of what would have been a tedious work day.

-Trying to take the “30 minute”personality test/calculus challenge for a “Marketing Consultancy Samurai Guru” position at a “pretty big deal”, local Inbound Marketing Company. Oh, and I decided to do this on Mother’s Day in the brief interval when may two kids “should” be napping.  This doesn’t seem like much until you factor in that over an hour into this mock-SAT: I am sweating profusely while my two-year old (sans nap)  climbs all over me, and my wife taps her toes in my direction, standing with a baby in one hand and a giant “child management control” bag in the other, reiterating that the car is indeed packed and that we are now late for dinner at “YOUR” parents’ house.

-Grabbing dinner at a local-yokel establishment when the family is out of town and chatting up a technology headhunter who ends up kinda being a big deal. Like most of my discussions with the kind and connected people I have been randomly meeting on this odyssey, I am blown away by the kindness and willingness to help that actually exists in this world. I think the best thing that this whole experience has taught me is how much people want to help others, whether they know them or not. However, in this instance, the connection kind of disappears, Keyser Soze-style, and I never hear from him after multiple emails. The thing is, the whole thing has me questioning whether or not the headhunter even existed (he did-actually confirmed by a co-worker) because he disappeared from my life so cleanly and completely. I am going to send another email in the morning. Keyser Soze didn’t just disappear forever. The car he drove off in had some destination. Right?

Next week: Part Two – The Contest?!?


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Ideas for Business Work Incredibly Well in Various Areas of Your Life

Recently, there was a guest post on Brad Feld’s blog, Startup Life, from  Scott and Cathy Yates. The Yates’s happen to have some pretty great ideas about how communication in marriage is a vital component of successful  entrepreneurial ventures. They should know, they both had roles in creating the well-funded blog content creation site, BlogMutt.

The main idea of the post is that before you can seek out investors to fund whatever project you may be undertaking, you first need to win over your “first investor,” your spouse.

Think about it. If you are starting a new venture, there’s a good chance that your spouse will be investing in the idea pretty directly by supporting you as you work initially without a paycheck. Or the spouse may be sacrificing the time that might have been spent enjoying life with you as you spend all your nights and weekends working on your business.

Scott and Cathy present all the components–particularly the trust, honesty, and faith–that are needed for any entrepreneur’s dream fulfilling mission to be successful. You can read the entire article on Feld’s site: Startup Life-Your Spouse is Your First Investor.

As far as the deeper implications of the ideas presented in the article, they fall into the same category that I believe many thoughts focused on business improvement fall into: they can be applied to more areas than just business. The Yates’s story is not one of a successful business partnership, but that of a great life partnership.

In the mysterious way that some kind of karma works, I stumbled upon this article at just the right time in my life. Over the past couple of months, I have been really calling on my super-awesome wife to go above and beyond the normal duties of being a mother of two fun and rambunctious kids. As I have been trying to deepen connections in the Boston tech/innovation world while beginning a new adventure as a journalist, Sarah has often had to shoulder a greater burden at home.

Although my wife knows that I am so grateful for her added investment to our mutual journey, the Yates’s story made me want to get her more deeply involved in this wild phase of my life. As the article points out, “We think it’s important that you convince the person closest to you that you have a good idea, a good market, that the opportunity is ripe, and that you are the one to go after it.”

So, following the Yates’s advice, I made sure that all the details of my recent endeavors as well as the my plans for how I proposed to proceed on my “what-am-I-going-to-be-when-I-grow-up” odyssey clear to Sarah. It was a great discussion, and her feedback helped immensely. Approaching some aspects of our marriage as a start-up business should be an interesting adventure.

I just hope I did enough to convince her that I’m worth investing in!

Thanks Sarah!  I am so thankful for all you do, you amazing super-Mom!


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Great Night for Timbre, CoachUp at Boston Shark Tank / VentureFizz

 Great Night for Timbre, CoachUp at Boston Shark Tank / VentureFizz

The six finalists of the FutureM/BzzAgent Shark Tank arrived at Microsoft NERD with a promise that at least $100,000 would be committed by a group of investors that included Boston Seed’s Greg Balter, Hubspot’s Dharmesh Shah, and Fred Destin of Atlas Ventures, among others. After each company gave its pitch and the “sharks” deliberated on how to distribute their investments, a surprising $442,000 was committed to local tech/innovation startups.

The highlight of the entire event was the exchange between Intrepid Pursuit’s Mark Kasdorf and the duo of Destin and Balter. Destin countered the terms proposed to invest in Intrepid’s music discovery app Timbre. However, Kasdorf passed on the possible $150,000 to $200,000 offer which led to Dave Balter adding $100,000 to the deal. After some highly entertaining and pressure-filled moments, Kasdorf accepted $350,000 in funding from both Balter and Destin.

CoachUp’s founder Jordan Fliegel gave the most energetic pitch of the evening, taking advantage of the Shark Tank format to put the investors in the hot seat. When prodded by Dharmesh Shah whether CoachUp would expand to other areas, including music lessons, Fliegel responded passionately that they would not. In one of the most passionate moments of the night, he proclaimed, “No, nope it won’t happen, sports is huge, we are not leaving it.”

The evening was a success for Fliegel and CoachUp, as the coaching connection platform received $28,000 in funding from Shah as well as meetings with a couple of investors from the “Piranha Pool”, which was made up of various investors not on the featured panel. The company’s idea of “professionalizing the industry” of coaching was also praised and lauded by audience members covering the event on twitter.

Continue Reading at VentureFizz…


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Check Out my New Webpage

So I just created a new command center for myself at www.dennisbkeohane.com .  I thought it could be a kind of hub for my “professional” self.

Let me know what you think.  Please, comment or send me an email at den.b.keohane@gmail.com.  I especially would like to know what you think about the “Who is Dennis Keohane?” page.  Anywhere I’ve over-exaggerated or anything I’ve left out, please call me on it.

Thanks!


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Do Boston Companies Lack Work/Life Balance? – from Bostinno

Outside Magazine recently posted on its website and features in its latest edition the 2012 version of its annual “The Best Places to Work” based on work-life balance. The list is littered with product manufacturers, breweries, PR firms, and tech start-ups based out of hot bed adventure states like California, Colorado, Utah, Wyoming, and Montana.  Take a guess at how many companies from the Boston area cracked this year’s top 100.

Zero.

- Click Here to continue reading my post at Bostinno.com

 


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Free Advice

A quick note on serendipity.

 

I recently attended an Eventbrite class on setting up courses through the service and, although the class itself was very interesting, some of the people I met and the connections I made were more worthwhile than anything learned from the presentation.

 
I continue to be amazed by how much people are willing to help a stranger simply because of the emotional connection to the shared experience of the job search, career pivot, et al. What I mean is that we all have, at some point, looked into the abyss of possible future careers and everyone understands and can relate to that moment in your life when you have to figure out what you want to be. There is even a respect earned by adding risk to the equation; for example, people admire others who take chances in their lives that they themselves may have once taken or possibly thought of making but never did.

 
After the Eventbrite class, an older gentleman named Peter approached me and wanted to hear more of my story. He was very interested in my teaching career and my quest to figure out my future.  He is a retired architect and now helps to run a non-profit that sends educator to Zambia to teach children and try to curb the spread of AIDS. He was a very fascinating man. However, once he told me about his past and current projects, his tone shifted and his whole affect morphed from a casual business acquaintance to an elder sage. He lowered his voice, looked me in the eye, and mentored me on how to master a career change based on own personal story and the experience he had accumulated over years of connecting with others.
Peter told me that he often passed on advice to young architects who were looking for their ideal jobs, and that every young person he mentored successfully found their perfect job.

 
Here is what I learned from Peter:
When he was right out of college, he got a job working for a door-to-door encyclopedia salesman. He thought a sales job was the path he was going to take and saw his current work as the beginning phase of his future career. One day, the owner of the business, who sometimes went with Peter on sales, took him aside and said, “You don’t want to be a salesman, you want to be an architect, that’s all you talk about, and what you seem to love, be an architect.” So Peter, with no architectural experience, made up a plan for himself on how to get a job in architecture. He went to multiple firms and told each receptionist he met that he wanted to get into the business and asked if there was someone who could show him what the firm was working on. Almost all of the time, someone was more than willing to take Peter along and show him the work they were doing. In many of these instances, the person would show Peter around, tell him how the company worked, and explain the details of certain projects. This would often last for fifteen to twenty minutes. In the last 30 seconds of these one-to-one’s, Peter would say to the guide, “I know your firm doesn’t have any openings right now, but could you direct me to a company or architect who might be able to help me more?” He would follow the recommendation and go to the next connection. By the fourth connection, he had a job working for one of the most dynamic architectural firms in Boston (Walter Gropius’s firm!!). He credits the respect earned by showing up for a face to face with a real person as one of the reasons he got his dream job.

 
Peter suggested that I find some companies that I would love to work for and that I do the same as he did. He said its worked for almost everyone who’s tried this tactic.
So now, I need to figure out whose door I am going to knock on first.


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Don’t Hit the Wall – What Seth Godin, Leo Babauta, and Jeff Camaro have in Common

I believe in Karma.  Although I’m not really sure what that actually means.

I think it is a kind of fate/destiny.  I find that often, I will stumble upon a book/blog/article that serendipitously reflects something going in my own life.

Recently, I’ve read the work of three different writers, internet/life/marketing guru Seth Godin, zen sage Leo Babauta, and, (umm…) mass transit lone wolf Jeff Camaro, all of whom dig into topics that relate to one of the big pink elephants in my life, the prospect and difficulty of seeing a project to completion.  In some way, I’ve fallen into a habit that is quite the opposite of the that kind I referred to in my last post.

For a bunch of years now, I have been in the process of writing a thesis in order to graduate from the Harvard Extension School with an ALM degree in English.  I completed my course work eons ago, and I have been working on the various stages of my thesis project for some time.  I didn’t do myself any favors by choosing an obscure and encyclopedically extensive topic in the writing of Thomas Pynchon.  But that is no excuse; ‘no guts, no glory’ as someone was supposed to have said at some point in history.  I’ve been promised that I will be the first person to complete a thesis on Pynchon in the program’s history.

That is, if I get the stupid thing done.  I am smack in the middle of a massive bout of writer’s block.

I have read all of Pynchon’s massive novels, researched every possible lead for a connection to my topic, and written a twenty-plus page proposal for the project.  Now all I have to do is write the actual thing.  But I keep getting caught in a vicious cycle, some may call is samsara-esque.  I’ll work for a few days, get in the groove, then have life interruption come up and force me to take a break.  I’ll  fight hard to get back involved and eventually make some headway and then, SMACK, life again. Repeat, Repeat, Repeat.

As I am dealing with this great personal fault as well as my inability to overcome minor setbacks in regard to my thesis work, I came across three separate articles that serve as guideposts that reflect different approaches to metaphorically similar problems.  Eventually, I realized I already had the answer hardwired in my system, I just needed to remember how to “break through the wall.”

Seth Godin’s The Dip

So, I am a huge fan of Godin.  His books are short, sweet, and chock full of good ideas on how to live and work better.  The Dip is one of his shorter works, yet it has a very profound message.  Or, a couple of messages.

One premise he delves into is the idea of quitting your job if you are in what he refers to as a “cul-de-sac”.  He uses this term to explain the phenomena of being in not just a dead end job, by one where you feel trapped and don’t feel like you can ever get out.

However, his larger point in the book is about pushing through what he terms “the dip,” the defining moment where we either succumb to a fate of a standard, boring career path or rise above our own expectations and create work that is truly great.  Godin sites multiple examples of  innovators and business folk who have been infinitely successful by fighting through the dip to become truly exceptional.

Leo Babauta and “The Three-Day Monk Syndrome”

Leo Babauta, writer on the zenhabits blog, creates tidbits of advice that are always clear, simple, and seemingly breathless in their delivery.  Last month he wrote about the “Three-Day Monk Syndrome,” a phase which he describes as being, “obsessed with something for a short time, and pour[ing] yourself into it, only to stop a few days (or a week or two) later.”

As I struggled through my thesis work, this really struck a chord.

Leo goes on to give a few suggestions on how to beat the Three-Day Monk, most of it excellent advice.  Of particular note is his suggestion to “Don’t Force Yourself,” and turning a nagging roadblock into an enjoyable challenge.

The Wonderful Jeff Camaro Runs a Race

Around the same time I read Godin and Babauta, I came across an idea that I guess you could loosely say is in a similar vein on the Good Great Wonderful blog.  The blog, which is often full of absurdest rants and good old fashion nonsense, delves into Camero’s psyche while running a 5K.

The points that show up in “5 Kilometers of Anguish” are common to all three of these articles: lack of belief in self, moment of anguish, feelings of failure, and, ultimately, completion of task and understanding that the insurmountable really wasn’t as hard as it seemed while in the middle of the seemingly impossible task.

Camero really does well to explain what many runners and athletes feel when completing any race.  At the start, there is doubt; at the end there is a self chiding sense of feeling foolish for letting fear in in the first place.

What Every Runner Knows About the Wall

To continue with Camero’s story about the 5K, when he writes about the moment, 2.5 miles into the race when he faces, “Deep soul-wrenching questions about the course and direction of my life, questioning the foundations of what makes me who I am.” What he is describing is the wall.  It is a running term for the, mostly mental, moment when you don’t think you can go on, your body has maxed out.  This is very similar to Seth Godin’s Dip.

What most runner’s know about the wall is similar to what all three of these writers say about their related theories:

IT ISN’T REAL.

The wall is imaginary, it is your mind and body trying to trick you into taking too much physical risk.  Once you’ve conquered the wall, you realize that your capacity for speed, endurance, etc. is actually much higher than you ever thought.  Being on the other side of the wall is great, euphoric at times almost.  Finding your true potential on the other side of the wall is what separates good runners from the truly great runners.

I am starting to find that this is true in life.  All the obstacles we create are mostly figments of our imagination. Yeah, there are things that we really can’t do; but for the most part, you can overcome anything, even the wall.

I need to start applying this simple idea to my thesis writing.  Once I get through the wall, I know I will be unstoppable.


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Habits

I can’t tell you how often people like to write and talk about habits.  It seems every self-help guru, zen master, life coach, uber-mentor, or, just anyone with a soapbox or blog has some advice on how to get rid of habits or avoid habits completely.

So, I’ve decided to add to the mayhem by writing a little blurb about my new outlook on habits.

Start a new habit, today!  It doesn’t need to be anything you are going to do for the rest of your life, just think of something that you like doing and try to do them as often as you can.

I’ve picked up a few new habits, they don’t really help me be a better person in any real way, they just make my day more interesting.  And that’s the whole point.

For years, I’ve had a middling interest in Eastern religions.  The ideas of zen, karma, and reincarnation are fascinating.  I took a couple of classes on Buddhism, Hinduism, Confuscisim, et al. in college and found the classes extremely interesting (the professors of these classes were some of the best and most intriguing teachers I ever had the opportunity to learn from.)  And, I have done some yoga in my time; something you shouldn’t knock until you try it.

One of the key foundation of Buddhism in particular has to do with mediation.  Almost anyone who is anyone has at one time or another professed the awesome power that meditiating can have on your health, sex-life, and just generally hipness.

I have never been able to sustain any kind of practice until recently.  I thought meditation might be a good way to gain focus to start the day, and it seems to sharpen the mind a bit.  However, I have not come close achieving any kind of Nirvana.  I just take a few minutes in the morning, when I remember to, while the dog is outside in the yard for her morning exercises.  I sit on the floor in my sunroom with my back against a wall, try to sit in some sort of cross-legged position, and just breathe and let my my wander.  I don’t do this everyday, but it is a habit that I sometimes take part in and I have found that a couple of minutes of mindfullness/mindlessness have helped me get my day off to a better start than hitting snooze twenty times.

The other habit I have started also involves taking the dog out, but only at night.  Thanks to our great new deck (built by the greatest handyman ever, Jeff “Pop” Wadman) I have a place to stand right outside our sunroom while the dog completes her evening exercises.

So, with this opportunity, I have begun to nightly take a few moments and look at the stars.  I mean really look at the stars.  There are few things in this world available to everyone for free that can affect an appreciation of beauty and also inspire ideas and dreams as the cosmic light display every evening.  I have tried, when the sky is not cloudy, to take few moments to get lost in the evening stars.  It is a great way to end the day.

So that’s it, two mindless habits, that take up may ten or twenty minutes of  my time per day, that make me happy.

Someones got to invent better word than HABITS so that everyone doesn’t get confused by the implied negative connotation of repeatedly doing something silly yet rewarding.

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