The Ambitious Life

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  • The Simplicity Paradox: Simple > Complex > Simplicity “When you start looking at a problem and it seems really simple,  you don’t really understand the complexity of the problem.  Then you get into the problem,  and you see that it’s really complicated,  and you come up with all these convoluted solutions.  That’s sort of the middle,  and that’s where most people stop. But the really great person will keep on going and find the key, the underlying principle of the problem — and come up with an elegant,  really beautiful solution that works.” - Steve Jobs. That’s one of my favorite Steve Jobs quotes. It does a great job in capturing the counter-intuitive nature of how simplicity is harder than complexity.I’ll go one step further and create the following framework: Simple > Complex > SimplicityThis framework applies to many facets of life, certainly beyond product development. Simplicity is elegant. It’s easy to work towards. It’s easy to understand and to sell. But there’s a big difference between simplicity and simple in this case. Once you get over the complexity hump, the solution seems obvious, and seems like it could have been achieved without the work of going through the complexity hump. In practice that’s not the way it works. Truly elegant solutions are the result of fighting through complexity, and are rarely single insights. Here are a few examples: The iPhone is perhaps the greatest example of this framework. After the original simple telephone, which let you simply dial and speak, companies went on a feature arms race to continually add new features. Address book, speed dial, calendar, etc. And phones got to be very very complex. And technology companies relished in that complexity and tripped over each other to add features and more complexity. Then the iPhone came along, the result of pushing through the complexity limitation, and ushered in a new era of phones. In politics we’ve recently seen a similar situation. Romney’s Tax Plan is in the “simple” category. Easy to sell and explain and put into sound bites. But it doesn’t have details because it hasn’t started actually trying to solve the problem. On the next step is Obama, who is so mired in details that he can’t convey a vision for his plan. His terrible performance in the first presidential debate last week showed this. He was trapped in the complexity of the details, trying to explain and resolve real deep challenges to make this all work. Now compare this to the polished arguments of Clinton’s DNC speech, where he accurately portrayed the key issues on both sides, in a simple way that people could understand and relate to. The same is true in architecture, one of my passions. All architecture started as simple housing and shelter. Then continued to get more complex and decorative. This decorative trend culminated in the Beaux Arts School (literally and figuratively) of architecture. Architects tripped over themselves to add more details and ornamentation the way Samsung and Acer add faceless “specs” to tech products. Then came the modern movement, led by the Bauhaus school, which focused on simplicity. Elegant solutions to challenging problems. And this style and philosophy remains the most elegant in the world. Have you wondered why an Eames chair designed in the 50’s looks more contemporary and futuristic than an Aeron chair designed in the 90’s? And finally, we see this same trend in the growth of knowledge. Things start as simple: thy sky is blue. Then get complex: because light refracts at that particular wavelength due to the molecular composition of our atmosphere. Then as you really understand things, a new simplicity emerges. The understanding that chemistry, physics, and biology are not separate disciplines, but different ways of looking at the same physical world. As Einstein put it so elegantly: “If you can’t explain it simply, you don’t understand it well enough”.So whether you’re explaining something, designing something, or building something, keep this in mind. Don’t be naive and think things are simple. Don’t be lazy and let yourself stay in the complex. Work towards simplicity. 

    The Simplicity Paradox: Simple > Complex > Simplicity

    “When you start looking at a problem and it seems really simple,  you don’t really understand the complexity of the problem.  Then you get into the problem,  and you see that it’s really complicated,  and you come up with all these convoluted solutions.  That’s sort of the middle,  and that’s where most people stop. But the really great person will keep on going and find the key, the underlying principle of the problem — and come up with an elegant,  really beautiful solution that works.” - Steve Jobs. 
    That’s one of my favorite Steve Jobs quotes. It does a great job in capturing the counter-intuitive nature of how simplicity is harder than complexity.

    I’ll go one step further and create the following framework: 
    Simple > Complex > Simplicity
    This framework applies to many facets of life, certainly beyond product development. 

    Simplicity is elegant. It’s easy to work towards. It’s easy to understand and to sell. But there’s a big difference between simplicity and simple in this case. Once you get over the complexity hump, the solution seems obvious, and seems like it could have been achieved without the work of going through the complexity hump. In practice that’s not the way it works. Truly elegant solutions are the result of fighting through complexity, and are rarely single insights. 
    Here are a few examples: 


    The iPhone is perhaps the greatest example of this framework. After the original simple telephone, which let you simply dial and speak, companies went on a feature arms race to continually add new features. Address book, speed dial, calendar, etc. And phones got to be very very complex. And technology companies relished in that complexity and tripped over each other to add features and more complexity. Then the iPhone came along, the result of pushing through the complexity limitation, and ushered in a new era of phones. 

    In politics we’ve recently seen a similar situation. Romney’s Tax Plan is in the “simple” category. Easy to sell and explain and put into sound bites. But it doesn’t have details because it hasn’t started actually trying to solve the problem. On the next step is Obama, who is so mired in details that he can’t convey a vision for his plan. His terrible performance in the first presidential debate last week showed this. He was trapped in the complexity of the details, trying to explain and resolve real deep challenges to make this all work. Now compare this to the polished arguments of Clinton’s DNC speech, where he accurately portrayed the key issues on both sides, in a simple way that people could understand and relate to. 
    The same is true in architecture, one of my passions. All architecture started as simple housing and shelter. Then continued to get more complex and decorative. This decorative trend culminated in the Beaux Arts School (literally and figuratively) of architecture. Architects tripped over themselves to add more details and ornamentation the way Samsung and Acer add faceless “specs” to tech products. Then came the modern movement, led by the Bauhaus school, which focused on simplicity. Elegant solutions to challenging problems. And this style and philosophy remains the most elegant in the world. Have you wondered why an Eames chair designed in the 50’s looks more contemporary and futuristic than an Aeron chair designed in the 90’s? 

    And finally, we see this same trend in the growth of knowledge. Things start as simple: thy sky is blue. Then get complex: because light refracts at that particular wavelength due to the molecular composition of our atmosphere. Then as you really understand things, a new simplicity emerges. The understanding that chemistry, physics, and biology are not separate disciplines, but different ways of looking at the same physical world. As Einstein put it so elegantly: “If you can’t explain it simply, you don’t understand it well enough”.
    So whether you’re explaining something, designing something, or building something, keep this in mind. Don’t be naive and think things are simple. Don’t be lazy and let yourself stay in the complex. Work towards simplicity. 
    • 7 months ago
  • The Right Solution to the “E-Book Problem”: Putting Students First

    A couple of weeks ago I wrote a guest post on Forbes.com about the future of e-textbooks. Here is the post in its entirety, and you can view it on Forbes here. 

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    Textbook publishers are trying to stay relevant in this increasingly open and digital world–but at what cost?

    Tom Malek’s recent guest post on this site (“Solving the E-book Problem in Higher Education”) details textbook publisher McGraw-Hill’s new plan to accelerate the adoption of its digital texts by forcing students to buy the e-books for their courses, whether they’d like to or not.

    The textbook industry is often called a broken market, as the end consumers do not select the product that they’re ultimately forced to buy. Students are able to choose from a number of options, thankfully, such as used and rental texts, but this compulsory e-book model threatens to make things even worse for them.

    Today’s E-Books Don’t Meet Students’ Needs

     Malek is right about one thing—digital is the future of higher education. According to a recent survey conducted by Wakefield Research, the majority of college students (67%) use digital technology every hour. A startling 40% of students can’t stay away from technology for more than 10 minutes at a time.

    However, his conclusion about why today’s e-books are failing is wrong. Malek blames the slow uptake of digital texts on students’ ignorance of the benefits of e-books and their reluctance to give up the “familiarity” of print. Studies have shown that more than half of students do still prefer physical textbooks to e-books. Yet if you give those students a chance to interact with a great e-book experience on an iPad,75% of them prefer the digital alternative.

    Today’s e-books aren’t the solution to students’ textbook woes because they’re expensive, poorly designed products that students don’t want. Publishers make very high gross margins on traditional textbooks, and since e-books radically reduce the cost of distribution and printing, one would expect prices to drop substantially for digital offerings. Yet thus far, e-books haven’t saved students enough to make switching from print worthwhile. A recent study released by Daytona State College revealed that many students only saved $1 by switching to e-books.

    Malek argues that the high-cost of e-books is due to the fact that physical production costs are “only a fraction of what it costs to produce a textbook.” Yet numerous innovative publishers have found ways to produce high-quality texts for far less than their traditional counterparts. Flat World Knowledge, for example, offers cheap print copies of their textbooks and makes them available for free online.

    Price aside, the reality is that students have never been offered excellent digital products that cater to the way they best study and learn. A quick glance at traditional publishers’ e-books reveals mostly non-interactive PDF files and “innovative learning platforms” that are little more than multiple-choice questions with a shoddy user experience. Malek and the publishers have chosen to ignore the obvious signal of students’ disdain for current e-book offerings, calling it a mere “problem of perspective.” But rather than improving that perspective, their plan is to drive students even deeper into the textbook trap.

    Malek’s Solution: Eliminating Student Choice

    This new “model” is a brazen attempt by publishers to further insulate themselves from market pressure. Malek justifies the forced-purchasing model by setting up a false dilemma: the choice between very expensive digital texts and slightly less expensive ones. He avoids the obvious third option—better and significantly cheaper digital learning tools.

    It’s not a surprising omission: e-books are a publishers’ dream, as they’re often riddled with restrictive DRM and eliminate the booming secondary market of used and rental texts. Despite this fact, Malek claims that this new forced purchasing model will ultimately help students save money.

    Yet by hiding textbook costs in the tuition bill, prices are even MORE likely to increase. According to the US Bureau of Labor Statistics, textbook prices have already risen over 500% over the past 30 years, at 3X the rate of inflation. Only three things have risen faster: tuition, tobacco and hospital stays. Do we really need another excuse to accelerate the rise of textbook prices by bundling them with something that is rising even faster?

    Student loan debt has reached new heights in this country—additional mandatory costs are the last thing our college students need. In fact, this forced purchasing policy would increase the total mandatory cost at community colleges by 33%, where textbooks often make up a quarter or more of tuition, fees & supplies.

    Is it any wonder that Malek doesn’t mention student sentiment in his discussion of the pilot programs of this new model?

    Putting Students First

    The best way to solve the “problem” of e-book adoption is creating MORE of a market, not further restricting competition. The future of education lies in building products for students—after all, they’re the ones whom the educational system is meant to serve. Thankfully, countless innovators and educators are putting in the hard work to realize the dream of a more student-centered design approach.

    The Open Educational Resources movement has created an enormous library of 100% free content for students and professors alike. Open Content understandably does not compute for traditional publishers, as it can be both cheaper and more effective than traditional alternatives. Wikipedia, for example, often contains the same information (and more) than expensive introductory texts in a given subject.

    Education technology companies have seen an unprecedented acceleration of venture investment over the past few years, topping $400MM in 2011 and potentially surpassing that this year.

    New initiatives like MIT and Harvard’s edX are promising to distribute high-quality free content to learners around the globe. Companies like Kahn Academy are creating enormous content libraries that integrate deeply with the “super-adaptive” learning tools Malek praises—for $0. At Boundless, we’re committed to replacing textbooks altogether by connecting students with open content in new and exciting ways.

    The Future of Educational Content

    Desperate attempts to protect antiquated business models are not the answer. The solution is delivering great products for students.

    The seeds of this educational revolution are being sown in classrooms, incubators and coffee shops all around the world.

    It’s time to give students more choice—not less.

    • 11 months ago
    • #JustMigrated
  • The Consumerization of Education

    You don’t have to search far to see the many frustrations with the efficacy or cost of our current educational system. While there are many possible reasons for this, I’d like to focus on particular dynamics of education.
    Traditional education products and services are ‘sold’ to key decision makers who then force the decision onto end-users. It’s no surprise then, that the result of this process are products that are inferior in the eyes of end-users. The products may very well meet some checklist that is deemed important to a key decider, but this checklist is usually different from the needs and desires of the end-users, namely, the students. One example is the oft-maligned “standardized tests”, which benefits states and districts looking for singular comparison metrics, yet often fail students by limiting exploration, breadth, and teaching focus.

    Slowing Innovation in IT
    Another industry that long had similar structural and market dynamics was corporate IT (information technology).
    Just ten to fifteen years ago, technological innovation was driven primarily by business needs. New products were sold into businesses and large corporations, and eventually trickled down into the consumers. Whether it was the fax machine, the copy machine, or even early personal computers. The same was true for software.

    The problem with that model was that the ‘decider’ was usually a different person than the ultimate ‘end user’. Corporate CIOs would make buying decisions of software and hardware for 50,000 employees, who were then forced to toil in terrible user interfaces and inferior hardware. Innovation suffered.
    The Consumerization of IT
    Then something changed. Companies began focusing on end-users, and began delivering terrific products, from software like Basecamp from 37Signals, to the biggest tech success of this generation in Apple. 

    Apple is leading the biggest disruption in today’s IT world by being a consumer-first company. Apple kept their relationship with the end-user first and foremost, and was able to deliver great products, and ultimately great profits. This wave of innovation would not have happened had the business-first technology leaders continued to dominate. 
    Another great outcome of the consumerization of IT and other verticals is the empowerment of the end-user. This new-found decision making and interest in the product can lead to increased productivity, and is evidenced in droves of business users buying and bringing their own iPhones to work, eschewing the corporate issued Blackberry. 

    The Consumerization of Education
    We are in a similar position in education. Innovation in education has stagnated because market forces don’t reward innovation. Market dynamics put very little power in the hands of students. Students cannot choose much today, other than where to go to school. There is tremendous opportunity to serve the needs of students directly, and use that relationship to drive significant and disruptive innovation. 
    Key elements to enable Consumerization 
    In order to really drive ‘consumerization’ of any industry or product, two ingredients are necessary:

    1) a direct relationship to the end user
    2) a desire to build amazing products
    I believe strongly in both, which in education means focusing on the student first, and delivering a delightful learning experience, resulting in a more engaged and empowered consumer.

    The next great wave of companies and platforms, especially in education, will be built with this ethos.
    • 1 year ago
    • #JustMigrated
  • Returning to blogging - with an education focus

    It’s been about a full year since I last blogged. 
    That year has been incredible from a personal and professional standpoint. I’ve gotten engaged, started a new company working with a great team and a great group of investors, and even recently gotten a puppy.

    This startup, Boundless Learning, was the primary reason for not blogging during that time. Not just from a time perspective, but from a mental energy perspective. All of my mental energy (and most of the physical energy) in that time period has gone towards establishing Boundless, working on everything from high level and long term vision, to immediate concerns like hiring, product roadmaps, content creation, etc. 
    One area that has been central to the past year has been education. I’ve always been passionate about education, both my personal education (in and out of school), as well as the education system and what it means for society as a whole. 

    Going forward, I’m going to channel my desire to blog more, with my passion and ongoing experience with education and learning. We’ve been learning a ton about the past and present of education, and are working night and day to help define it’s future.
    Stay tuned.
    • 1 year ago
    • #JustMigrated
  • Strengths and Weaknesses: Two Sides of the Same CoinWe often think about strengths and weaknesses in a vacuum, as if they were completely unrelated to each other. We think about building up strengths and eliminating weaknesses.  That’s a bit disingenuous and logically impossible because you end up stuck in the middle, with no real strengths or weaknesses. You end up averaging out strengths and weaknesses, resulting in an unidentifiable and uninteresting mediocre mix of traits. Instead, we should be thinking about both the strengths and weaknesses tied to a given trait or characteristic.  Every strength has a corresponding weakness, inherent to the underpinnings of that strength. Company size as both a strength and weaknessIf you’re a large company, like Google, you can throw dozens of engineers and other resources to try to a problem. That’s a lot of momentum moving in one direction, but that also means it’s harder to get going, harder to change directions, and harder to react to uncertainties or changing environments. On the flip side, if you’re a small company, you may not have a lot of resources, but you can be nimble, make faster decisions, and out-maneuver larger competitors.  Personal strengths and weaknessesPersonal traits also inherently have strengths and weaknesses. Most of the time, we get feedback throughout our lives about the weaknesses or limitations, and end up focusing on reducing or eliminating those. We don’t realize that we’re also weakening the complementary strength. We end up settling for the lowest common denominator.CompetitivenessI compete in everything I do, big and small, creating competitions out of non-competitive things, keeping score in every game where score is kept. That competitive outlook has helped me in almost everything I’ve done, from succeeding in sports my whole life, to my academic career, to the current startup world I’m in.  But it does have a complementary weakness. Über-competitiveness can be off-putting in certain social situations. But the reality is that it’s not something I can just turn it on and off.  I’m willing to manage and deal with the social awkwardness that may come with being über-competitive.ConfidenceThe power of confidence can create a positive feedback loop of increasing confidence, increasing ambition, and increasing achievement.  But there are also inherent weaknesses of confidence.  The classic is hubris, a self-defeating pride that can lead people to forget their limitations and pursue unattainable and ultimately fatal goals. Another more benign one is that extreme confidence can also occasionally seem arrogant and egotistical, especially in a crowd of non-confident people. Perseverance I don’t give up very easily, will fight to achieve long term goals, and will work hard and summon other strengths (like confidence and competitiveness) to get things done. Like the two traits above, perseverance is so entrenched in my world outlook, that I don’t doubt it will get me through the darkest and most challenging times. But it also comes with a cost, the complement of perseverance is stubbornness. Even the word stubbornness has both positive and negative connotations. It’s important to be aware of both, and to understand the balance, but to realize they go hand in hand.Managing strengths and weaknessesGiven that strengths and weaknesses are different ways of looking at a particular characteristic, the next step is to think about how to manage or deal with weaknesses.  The goal is not to eliminate or mitigate weaknesses, because that would inherently eliminate or mitigate the corresponding strength. Understanding the tradeoffs of each trait is a sign of maturity. Being able to acknowledge weaknesses that are the flip side of a strength is important. Next time you’re thinking about a weakness, think about it’s corresponding strength - somewhere in that weakness is an inherent strength.  Then think about whether it’s worth tempering that strength in order to temper the weakness.  Or even better, how to be aware of both and use it to your advantage. This is also highly relevant when building a team for a startup or other endeavor. Don’t worry about mitigating weaknesses, instead focus on finding a team whose strengths work well together, and whose inherent weaknesses balance each other out.Image Source: http://www.bigbadtoystore.com/bbts/product.aspx?product=IMP10016&mode=retail1

    Strengths and Weaknesses: Two Sides of the Same Coin

    We often think about strengths and weaknesses in a vacuum, as if they were completely unrelated to each other. We think about building up strengths and eliminating weaknesses.  That’s a bit disingenuous and logically impossible because you end up stuck in the middle, with no real strengths or weaknesses. You end up averaging out strengths and weaknesses, resulting in an unidentifiable and uninteresting mediocre mix of traits. 
    Instead, we should be thinking about both the strengths and weaknesses tied to a given trait or characteristic.  Every strength has a corresponding weakness, inherent to the underpinnings of that strength. 

    Company size as both a strength and weakness
    If you’re a large company, like Google, you can throw dozens of engineers and other resources to try to a problem. That’s a lot of momentum moving in one direction, but that also means it’s harder to get going, harder to change directions, and harder to react to uncertainties or changing environments. On the flip side, if you’re a small company, you may not have a lot of resources, but you can be nimble, make faster decisions, and out-maneuver larger competitors.  
    Personal strengths and weaknesses
    Personal traits also inherently have strengths and weaknesses. Most of the time, we get feedback throughout our lives about the weaknesses or limitations, and end up focusing on reducing or eliminating those. We don’t realize that we’re also weakening the complementary strength. We end up settling for the lowest common denominator.

    Competitiveness
    I compete in everything I do, big and small, creating competitions out of non-competitive things, keeping score in every game where score is kept. That competitive outlook has helped me in almost everything I’ve done, from succeeding in sports my whole life, to my academic career, to the current startup world I’m in.  But it does have a complementary weakness. Über-competitiveness can be off-putting in certain social situations. But the reality is that it’s not something I can just turn it on and off.  I’m willing to manage and deal with the social awkwardness that may come with being über-competitive.
    Confidence
    The power of confidence can create a positive feedback loop of increasing confidence, increasing ambition, and increasing achievement.  But there are also inherent weaknesses of confidence.  The classic is hubris, a self-defeating pride that can lead people to forget their limitations and pursue unattainable and ultimately fatal goals. Another more benign one is that extreme confidence can also occasionally seem arrogant and egotistical, especially in a crowd of non-confident people. 

    Perseverance 
    I don’t give up very easily, will fight to achieve long term goals, and will work hard and summon other strengths (like confidence and competitiveness) to get things done. Like the two traits above, perseverance is so entrenched in my world outlook, that I don’t doubt it will get me through the darkest and most challenging times. But it also comes with a cost, the complement of perseverance is stubbornness. Even the word stubbornness has both positive and negative connotations. It’s important to be aware of both, and to understand the balance, but to realize they go hand in hand.
    Managing strengths and weaknesses
    Given that strengths and weaknesses are different ways of looking at a particular characteristic, the next step is to think about how to manage or deal with weaknesses.  The goal is not to eliminate or mitigate weaknesses, because that would inherently eliminate or mitigate the corresponding strength. 

    Understanding the tradeoffs of each trait is a sign of maturity. Being able to acknowledge weaknesses that are the flip side of a strength is important. Next time you’re thinking about a weakness, think about it’s corresponding strength - somewhere in that weakness is an inherent strength.  Then think about whether it’s worth tempering that strength in order to temper the weakness.  Or even better, how to be aware of both and use it to your advantage. 
    This is also highly relevant when building a team for a startup or other endeavor. Don’t worry about mitigating weaknesses, instead focus on finding a team whose strengths work well together, and whose inherent weaknesses balance each other out.

    Image Source: http://www.bigbadtoystore.com/bbts/product.aspx?product=IMP10016&mode=retail1
    • 2 years ago
    • #JustMigrated
  • The Secret Power of Confidence and How to Build ItConfidence is one of the most important traits in life. It is imperative for everything from dating and relationships, to startups and business. Most of the conventional wisdom around confidence and self-esteem is trying to find a short cut. But the reality is that you can’t create real confidence by reading a WikiHow article about how to be confident. You can’t create confidence by simply telling yourself that you are special, smart, interesting, or appealing to others, as some confidence “experts” will tell you. All of that is simply addressing the symptoms not the underlying issue.
Real Confidence
The only way to create real confidence is to succeed in something challenging. Everything else is as empty as a participation trophy in elementary school. Real confidence is built upon a solid foundation of achievement, that you can look back on and know is real when things get tough. True confidence is so humble it’s arrogant, and so arrogant it’s humble. 
The Confidence Cycle
Confidence creates a virtuous cycle. It raises ambition, which in turn means you seek out higher goals, which also motivates you to achieve them, which brings you success, which then gives you more confidence that fuels the cycle.

Building Confidence - Seek out challenges
Since the only way to build true confidence is to succeed in something challenging, you need to seek out challenges, and be motivated enough to complete them. This process can start with small goals, to help build the cycle. The challenges do not have to be related to a core strength or long term goal, and are often more challenging and rewarding when they’re outside your core competency. For instance, if you’re an English-major, all-star athlete, learn to build a website.  Conversely, if you’re a techy non-athlete, run a marathon. If you’ve already run a marathon, run an ultra-marathon. If you’re a social butterfly, read the longest book you’ve ever read. It’s not about over-optimizing for the specific challenge, just find one, get started, and continue until you succeed.

The risk of a single source of confidence
Too often a person’s confidence is tied to a specific source, whether it’s their job, their marriage, their alma matter, or their prowess in a particular skill. There are two risks with this single source. First off, it may not imply ability or confidence in other areas. And secondly, if that single source disappears (getting fired from a job, divorce, etc.), you lose all of your confidence and go into a downward spiral. This is one of the biggest challenges of chronic unemployment. People’s confidence is tied to their job, so when they lose it, they are left exposed. 

The Confidence Portfolio
Real, robust confidence is only attained with a diversified and well balanced confidence portfolio. In order to create that, you need to continue pushing yourself with a diverse set of challenges. Make them diverse, then build on successes and let that fuel your rising ambition. The more diverse your sources of confidence, the more stable it is, because you’re creating balance through excellence in multiple things. Psychological research has shown that increased self-complexity, i.e. the different ways of perceiving oneself and one’s strengths, leads to lower levels of depression, stress, and illnesses:

“Subjects higher in self-complexity were less prone to depression, perceived stress, physical symptoms, and occurrence of the flu and other illnesses following high levels of stressful events. These results suggest that vulnerability to stress-related depression and illness is due, in part, to differences in cognitive representations of the self.”

“Self-complexity as a cognitive buffer against stress-related illness and depression.”Patricia Linville, Yale Psychology Professor, http://www.ncbi.nlm.nih.gov/pubmed/3572732



Get out there and challenge yourself. In a follow up post I’ll share some examples of my own diverse set of confidence.

    The Secret Power of Confidence and How to Build It

    Confidence is one of the most important traits in life. It is imperative for everything from dating and relationships, to startups and business. Most of the conventional wisdom around confidence and self-esteem is trying to find a short cut. But the reality is that you can’t create real confidence by reading a WikiHow article about how to be confident. You can’t create confidence by simply telling yourself that you are special, smart, interesting, or appealing to others, as some confidence “experts” will tell you. All of that is simply addressing the symptoms not the underlying issue.
    Real Confidence
    The only way to create real confidence is to succeed in something challenging. Everything else is as empty as a participation trophy in elementary school. Real confidence is built upon a solid foundation of achievement, that you can look back on and know is real when things get tough. True confidence is so humble it’s arrogant, and so arrogant it’s humble. 
    The Confidence Cycle
    Confidence creates a virtuous cycle. It raises ambition, which in turn means you seek out higher goals, which also motivates you to achieve them, which brings you success, which then gives you more confidence that fuels the cycle.
    Building Confidence - Seek out challenges
    Since the only way to build true confidence is to succeed in something challenging, you need to seek out challenges, and be motivated enough to complete them. This process can start with small goals, to help build the cycle. The challenges do not have to be related to a core strength or long term goal, and are often more challenging and rewarding when they’re outside your core competency. For instance, if you’re an English-major, all-star athlete, learn to build a website.  Conversely, if you’re a techy non-athlete, run a marathon. If you’ve already run a marathon, run an ultra-marathon. If you’re a social butterfly, read the longest book you’ve ever read. It’s not about over-optimizing for the specific challenge, just find one, get started, and continue until you succeed.
    The risk of a single source of confidence
    Too often a person’s confidence is tied to a specific source, whether it’s their job, their marriage, their alma matter, or their prowess in a particular skill. There are two risks with this single source. First off, it may not imply ability or confidence in other areas. And secondly, if that single source disappears (getting fired from a job, divorce, etc.), you lose all of your confidence and go into a downward spiral. This is one of the biggest challenges of chronic unemployment. People’s confidence is tied to their job, so when they lose it, they are left exposed. 
    The Confidence Portfolio
    Real, robust confidence is only attained with a diversified and well balanced confidence portfolio. In order to create that, you need to continue pushing yourself with a diverse set of challenges. Make them diverse, then build on successes and let that fuel your rising ambition. The more diverse your sources of confidence, the more stable it is, because you’re creating balance through excellence in multiple things. Psychological research has shown that increased self-complexity, i.e. the different ways of perceiving oneself and one’s strengths, leads to lower levels of depression, stress, and illnesses:
    “Subjects higher in self-complexity were less prone to depression, perceived stress, physical symptoms, and occurrence of the flu and other illnesses following high levels of stressful events. These results suggest that vulnerability to stress-related depression and illness is due, in part, to differences in cognitive representations of the self.”
    “Self-complexity as a cognitive buffer against stress-related illness and depression.”Patricia Linville, Yale Psychology Professor, http://www.ncbi.nlm.nih.gov/pubmed/3572732

    Get out there and challenge yourself. In a follow up post I’ll share some examples of my own diverse set of confidence.
    • 2 years ago
    • #JustMigrated
  • Losing 20 pounds in 3 monthsTowards the end of this past summer, I had gotten past my comfortable weight, as a result of a fun summer, not working out enough, and enjoying the food and beverage. I was up to 194 pounds, and though I carry it well (on my massive thighs primarily), it’s still pretty robust for my 5’10” frame.

It really pissed me off. And since I don’t believe in moderation, I decided to do something extreme about it, and on August 23, I tweeted the following:


Here I am, 3 months later, having achieved that goal. Looking back, here’s the simple plan and how it worked.

Step 1 - State goal publicly
I’m a big believer in using any means possible to motivate yourself, and committing to something publicly is a great motivator. So I tweeted and posted to Facebook about my goal, told all of my friends, and committed to myself. Not only did this motivate, but it’s also a great way to get other people’s support, especially when you’re turning down food and drink. 

Step 2 - Decrease food consumption
I don’t believe in fad diets. Losing weight is all about a simple equation:
Weight Loss = Calories IN - Calories BURNED (divided by about 3,500, which is the approx number of calories per pound).  
So if you’re running a 500 calorie deficit per day, you’ll lose about a pound a week. Since I was trying to go faster than that, I needed to make sure both factors changed. Reducing food consumption takes discipline, and it reminded me of my days as a lightweight rower. I didn’t skip meals (occasionally breakfast), just reduced what I ate, and ate extremely healthy foods.

Step 3 - Dramatically increase mileage
The second part of the equation is the calories burned. Once I made the goal, I went from running occasionally (5-10 miles a week) to regularly running 30-40 miles per week, every single week. Running 30 miles burns about 4,000-5,000 calories, which is about what I was targeting to lose. 

Step 4 - Profit
Three months later, I’m back at a comfortable 174 pounds, and at a steady point that I can maintain pretty well with some basic working out and healthy eating.  I feel great and look great (according to my girlfriend at least, which is all that counts). Just in time for Costa Rica ;)

Next Goal - Qualifying for Boston Marathon
Now I have to pick a big audacious goal to train for again, so I’ll announce that here. My goal is to qualify for the 2012 Boston Marathon.  For those of you keeping score (and who isn’t), that requires a 3:10 marathon, which is 26 miles at a brisk 7:15 per mile average pace.  The gauntlet has been thrown. 

    Losing 20 pounds in 3 months

    Towards the end of this past summer, I had gotten past my comfortable weight, as a result of a fun summer, not working out enough, and enjoying the food and beverage. I was up to 194 pounds, and though I carry it well (on my massive thighs primarily), it’s still pretty robust for my 5’10” frame.
    It really pissed me off. And since I don’t believe in moderation, I decided to do something extreme about it, and on August 23, I tweeted the following:

    Here I am, 3 months later, having achieved that goal. Looking back, here’s the simple plan and how it worked.
    Step 1 - State goal publicly
    I’m a big believer in using any means possible to motivate yourself, and committing to something publicly is a great motivator. So I tweeted and posted to Facebook about my goal, told all of my friends, and committed to myself. Not only did this motivate, but it’s also a great way to get other people’s support, especially when you’re turning down food and drink. 

    Step 2 - Decrease food consumption
    I don’t believe in fad diets. Losing weight is all about a simple equation:
    Weight Loss = Calories IN - Calories BURNED (divided by about 3,500, which is the approx number of calories per pound).  
    So if you’re running a 500 calorie deficit per day, you’ll lose about a pound a week. Since I was trying to go faster than that, I needed to make sure both factors changed. Reducing food consumption takes discipline, and it reminded me of my days as a lightweight rower. I didn’t skip meals (occasionally breakfast), just reduced what I ate, and ate extremely healthy foods.
    Step 3 - Dramatically increase mileage
    The second part of the equation is the calories burned. Once I made the goal, I went from running occasionally (5-10 miles a week) to regularly running 30-40 miles per week, every single week. Running 30 miles burns about 4,000-5,000 calories, which is about what I was targeting to lose. 

    Step 4 - Profit
    Three months later, I’m back at a comfortable 174 pounds, and at a steady point that I can maintain pretty well with some basic working out and healthy eating.  I feel great and look great (according to my girlfriend at least, which is all that counts). Just in time for Costa Rica ;)
    Next Goal - Qualifying for Boston Marathon
    Now I have to pick a big audacious goal to train for again, so I’ll announce that here. My goal is to qualify for the 2012 Boston Marathon.  For those of you keeping score (and who isn’t), that requires a 3:10 marathon, which is 26 miles at a brisk 7:15 per mile average pace.  The gauntlet has been thrown. 
    • 2 years ago
    • #JustMigrated
  • Fuck Moderation - Balance through ExtremesThis was originally written as a guest post on BostInnovation. There is a general conventional wisdom that everything in moderation is good.  As with a lot of conventional wisdom, that’s bullshit.  Everything in moderation leads to a dull, boring, shapeless, unidentifiable mass.  Moderation leads to complacency. Instead of moderation, pursue excellence.The Importance of BalanceThe irony of the conventional wisdom is that it hides a truly important point, which is the need for balance in life. While moderation is insidious, balance is important and beneficial. Balance creates interesting cross-polination, a diversified interest base, and an ability to use one strength to compensate for another when you need to. Balance creates stability and strength. On an individual level, It’s very fulfilling to have a diverse lifestyle, in the spirit the Renaissance man, but moderation is not the way to achieve true balance.How Extremism Creates StabilityIn physics, the moment of inertia quantifies the ability of an object to resist rotation. The more weight is out on the extreme of a given object, the higher the moment of inertia, and therefore the more stable it is. The best real world example is a long straight pole. With most of the weight way out on either side, it provides a very stable counter-balance that can be very useful when walking across, say, a tight-rope between the Twin Towers.Innovation is ExtremeOn an entrepreneurial level, all real innovation happens at the edge. There is simply no better way to learn an industry and try to fix a problem than starting a company and devoting all your mental and physical energy to solving or improving some important issue. Startups are extreme by definition, and that’s one of the things that makes them so disruptive. Innovation is extreme. Leave the moderation to large companies looking for 5% annual growth. Even within a startup, balance through extremes is important. For early teams, it may mean finding complementary founders, both of whom are amazing and strong in very different areas, like technology and marketing, for instance.Extreme AbstinenceOn the other side of the coin, there are many extremes that can be dangerous. In those cases, I think the best solution is to go extreme in the other direction, by abstaining completely. For example, I don’t gamble or watch TV because I don’t like those extremes.  So I go to the other extreme, by eliminating them completely. It’s not worth watching a single episode of a TV show, and I certainly don’t want to get hooked. In business, what you choose not to do is just as important as what you choose to actually do. It’s much easier to not start a project, or a feature, or a new market, than to do it half-assed.Focus on 1-3 Extremes at a TimeBy definition, being involved in something to the extreme is nearly all-consuming. Therefore, it’s important to focus on only 1-3 areas at a given time. When starting a company, especially in the early stages, it’s difficult to be extreme in much else.  But it’s good to have at least 1 counter-balanace. For me, it was training for an ultra-marathon (50 miles), which I used as an excuse to get me back in shape after 6 months of not working out due to injury. I ramped up my running to 30-40 miles per week, finished the ultra-marathon in just over 10 hours, and had a great time doing it.Vary the Extremes for DiversityWhile I enjoy living in extremes, I’ve found it important to vary my involvements over time to create a diverse perspective. I love staying physically fit and active, traveling, understanding different cultures, cooking, starting companies, learning, and much more.  But in order to gain real depth in each of those areas, I had to really focus on each for a period of time.  By choosing to dive in on a few things at a time, you can afford to be extreme.  As you rotate through your various potential interests and projects, you’ll find yourself with a much deeper knowledge base than if you had moderately pursued them all over a longer period.Choose what you want to do wisely, then do all of those things fully.

    Fuck Moderation - Balance through Extremes

    This was originally written as a guest post on BostInnovation. 

    There is a general conventional wisdom that everything in moderation is good.  As with a lot of conventional wisdom, that’s bullshit.  Everything in moderation leads to a dull, boring, shapeless, unidentifiable mass.  Moderation leads to complacency. Instead of moderation, pursue excellence.

    The Importance of Balance
    The irony of the conventional wisdom is that it hides a truly important point, which is the need for balance in life. While moderation is insidious, balance is important and beneficial. Balance creates interesting cross-polination, a diversified interest base, and an ability to use one strength to compensate for another when you need to. Balance creates stability and strength. On an individual level, It’s very fulfilling to have a diverse lifestyle, in the spirit the Renaissance man, but moderation is not the way to achieve true balance.How Extremism Creates Stability
    In physics, the moment of inertia quantifies the ability of an object to resist rotation. The more weight is out on the extreme of a given object, the higher the moment of inertia, and therefore the more stable it is. The best real world example is a long straight pole. With most of the weight way out on either side, it provides a very stable counter-balance that can be very useful when walking across, say, a tight-rope between the Twin Towers.

    Innovation is Extreme
    On an entrepreneurial level, all real innovation happens at the edge. There is simply no better way to learn an industry and try to fix a problem than starting a company and devoting all your mental and physical energy to solving or improving some important issue. Startups are extreme by definition, and that’s one of the things that makes them so disruptive. Innovation is extreme. Leave the moderation to large companies looking for 5% annual growth. Even within a startup, balance through extremes is important. For early teams, it may mean finding complementary founders, both of whom are amazing and strong in very different areas, like technology and marketing, for instance.Extreme Abstinence
    On the other side of the coin, there are many extremes that can be dangerous. In those cases, I think the best solution is to go extreme in the other direction, by abstaining completely. For example, I don’t gamble or watch TV because I don’t like those extremes.  So I go to the other extreme, by eliminating them completely. It’s not worth watching a single episode of a TV show, and I certainly don’t want to get hooked. In business, what you choose not to do is just as important as what you choose to actually do. It’s much easier to not start a project, or a feature, or a new market, than to do it half-assed.

    Focus on 1-3 Extremes at a Time
    By definition, being involved in something to the extreme is nearly all-consuming. Therefore, it’s important to focus on only 1-3 areas at a given time. When starting a company, especially in the early stages, it’s difficult to be extreme in much else.  But it’s good to have at least 1 counter-balanace. For me, it was training for an ultra-marathon (50 miles), which I used as an excuse to get me back in shape after 6 months of not working out due to injury. I ramped up my running to 30-40 miles per week, finished the ultra-marathon in just over 10 hours, and had a great time doing it.Vary the Extremes for Diversity
    While I enjoy living in extremes, I’ve found it important to vary my involvements over time to create a diverse perspective. I love staying physically fit and active, traveling, understanding different cultures, cooking, starting companies, learning, and much more.  But in order to gain real depth in each of those areas, I had to really focus on each for a period of time.  By choosing to dive in on a few things at a time, you can afford to be extreme.  As you rotate through your various potential interests and projects, you’ll find yourself with a much deeper knowledge base than if you had moderately pursued them all over a longer period.

    Choose what you want to do wisely, then do all of those things fully.
    • 2 years ago
    • #JustMigrated
  • Static Friction > Kinetic FrictionI love analogies, especially analogies between life and physics. On a recent run, I was thinking about the parallel between static friction and the forces that keep us from starting things.  We all remember the physics experiment from 8th grade, where we put a block of wood or plastic on a ramp, and see how high we can angle the ramp before the block starts moving. In order for the block to start moving, it has to overcome the static friction, which is the frictional force at work at rest, when the surfaces have time to settle and create a sort of frictional bond. Once the block got started, it only has to overcome kinetic friction, the friction against the object when it is motion. Kinetic frication is always lower than static friction. This point is reinforced by the experiment. You need to get to a much higher angle to overcome the static friction, but with a slight nudge at even a much lower ramp angle, the block will keep going.Life is very similar. The hardest part of any project or activity is starting it. The status quo is comfortable, it’s easy, it’s known. Something new is uncomfortable, hard, unknown, risky. But everyone knows that. What’s easier to forget is that once you start, the resistant forces, while still present, are actually much lower than what kept (or delayed) you from starting. So whether you’re lying in bed hating the run you said you’d go on, or hemming and hawing about a project you want to kick off, just start it. Trick yourself into starting it if you need. Start small. For example, if you’re having trouble running regularly, just tell yourself you’ll turn around after 5 minutes in the run if you don’t feel like continuing. You’ll likely never actually turn around after 5 minutes, because you’ll be warmed up, and you’ll feel good, but that trick will get you out of bed.  Whatever it takes to overcome the static friction, just do it.

    Static Friction > Kinetic Friction

    I love analogies, especially analogies between life and physics. On a recent run, I was thinking about the parallel between static friction and the forces that keep us from starting things. We all remember the physics experiment from 8th grade, where we put a block of wood or plastic on a ramp, and see how high we can angle the ramp before the block starts moving. In order for the block to start moving, it has to overcome the static friction, which is the frictional force at work at rest, when the surfaces have time to settle and create a sort of frictional bond. Once the block got started, it only has to overcome kinetic friction, the friction against the object when it is motion. Kinetic frication is always lower than static friction. This point is reinforced by the experiment. You need to get to a much higher angle to overcome the static friction, but with a slight nudge at even a much lower ramp angle, the block will keep going.

    Life is very similar. The hardest part of any project or activity is starting it. The status quo is comfortable, it’s easy, it’s known. Something new is uncomfortable, hard, unknown, risky. But everyone knows that. What’s easier to forget is that once you start, the resistant forces, while still present, are actually much lower than what kept (or delayed) you from starting.
    So whether you’re lying in bed hating the run you said you’d go on, or hemming and hawing about a project you want to kick off, just start it. Trick yourself into starting it if you need. Start small. For example, if you’re having trouble running regularly, just tell yourself you’ll turn around after 5 minutes in the run if you don’t feel like continuing. You’ll likely never actually turn around after 5 minutes, because you’ll be warmed up, and you’ll feel good, but that trick will get you out of bed.

    Whatever it takes to overcome the static friction, just do it.
    • 2 years ago
    • #JustMigrated
    • #analogies
    • #Traits
  • The Lower Right QuadrantA few months ago I got together in the old YouCastr offices with a big whiteboard, a few pizzas, a few packs of beer, and some entrepreneurial product folks to chat about various concepts (or schemes) and think about web trends in general. One of the concepts that emerged, admittedly following some mental lubricant, was the “Lower Right Quadrant”.  Being a former consultant, I love frameworks and 2x2 matrices. So as we were chatting about ridiculously profitable dating sites, and how hard we have all worked to create business that don’t throw off nearly those levels of cash, something hit me. Here is that framework: The framework looks at profitability vs. world impact. In the top right are profitable companies that impact the world for the better, like CleanTech (successful ones), and possibly Google (when they’re not being evil). The upper left quadrant are necessary humanitarian efforts that might not be very profitable, either by design (e.g. non-profits, government), or by market conditions (e.g. healthcare). The lower left quadrant is where most companies end up, slightly profitable or unprofitable, with little impact on the world. And finally, the Lower Right Quadrant, is where silly and salacious companies make a ton of money without attracting competition from well-intentioned entrepreneurs looking to make the world a better place.Interestingly, most startups think they’re in the upper right quadrant, and have audacious goals to change the world and enrich themselves and their investors. But most startups are actually in the lower left quadrant, making incremental products that end up not being very profitable.  We continued our discussion, thinking about opportunities in the LRQ, ranging from a Swoopo model for dating, to social games, to online pawn shops. One challenge we faced was realizing we weren’t really in the target market for any of the LRQ products we brainstormed, and had to continuously think outside of ourselves (or have a few more beers).  Another challenge is to get excited about something that is not inherently beneficial.  I do actually want to help the world, but there is probably some supply-demand type curve that relates profitability to world-changingness, i.e. the less utilitarian and world-changing the product / company is, the more profitable it has to be to motivate me to continue working on it.So, before you get all starry eyed about your next big world changing money-printing concept, think LRQ.  And get the shirt in the meantime.

    The Lower Right Quadrant

    A few months ago I got together in the old YouCastr offices with a big whiteboard, a few pizzas, a few packs of beer, and some entrepreneurial product folks to chat about various concepts (or schemes) and think about web trends in general. 
    One of the concepts that emerged, admittedly following some mental lubricant, was the “Lower Right Quadrant”.  Being a former consultant, I love frameworks and 2x2 matrices. So as we were chatting about ridiculously profitable dating sites, and how hard we have all worked to create business that don’t throw off nearly those levels of cash, something hit me. Here is that framework: 

    The framework looks at profitability vs. world impact. In the top right are profitable companies that impact the world for the better, like CleanTech (successful ones), and possibly Google (when they’re not being evil). The upper left quadrant are necessary humanitarian efforts that might not be very profitable, either by design (e.g. non-profits, government), or by market conditions (e.g. healthcare). The lower left quadrant is where most companies end up, slightly profitable or unprofitable, with little impact on the world. And finally, the Lower Right Quadrant, is where silly and salacious companies make a ton of money without attracting competition from well-intentioned entrepreneurs looking to make the world a better place.

    Interestingly, most startups think they’re in the upper right quadrant, and have audacious goals to change the world and enrich themselves and their investors. But most startups are actually in the lower left quadrant, making incremental products that end up not being very profitable.  
    We continued our discussion, thinking about opportunities in the LRQ, ranging from a Swoopo model for dating, to social games, to online pawn shops. One challenge we faced was realizing we weren’t really in the target market for any of the LRQ products we brainstormed, and had to continuously think outside of ourselves (or have a few more beers).  Another challenge is to get excited about something that is not inherently beneficial.  I do actually want to help the world, but there is probably some supply-demand type curve that relates profitability to world-changingness, i.e. the less utilitarian and world-changing the product / company is, the more profitable it has to be to motivate me to continue working on it.

    So, before you get all starry eyed about your next big world changing money-printing concept, think LRQ.  And get the shirt in the meantime.
    • 2 years ago
    • #JustMigrated
    • #business
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