50Plus jobs: micro-entrepreneurs create their own - why wait for "economic development"

$100 Startup Japan Manga Pic.png


"No money, no skill, just a tiny bit of an idea and its good for salarymen, office ladies, students, and seniors."

The book in the picture is the¥10,000 Startup, a 2015 Manga-style, Japanese language translation and adaptation of a very successful book published in English in 2012 by Chris Guillebeau, a fellow Portland resident, best-selling author and life-long micro-entrepreneur. The translation of the banner on the cover, "no money, no skill, just a tiny bit of an idea and it’s good for salarymen, office ladies, students, and seniors", immediately caught my eye. Those words could be the first sentence of my call to arms to anyone in the 50Plus demographic worried about a potential coming shortfall of their financial plan resulting from our unexpected good fortune of living longer than expected.

In a recent blog post, I made reference to current data from BlackRock, the largest asset manager in the world, to estimate the size of the problem facing the 50Plus demographic. The answer: the average Baby Boomer (75 million of the 110 million 50Plus demographic) in the US is likely to fall $36,350 per year short of their own estimate of a $45,500 annual income goal given that they currently have only $136,200 in retirement assets shown in Figure 2. The question stands, can this hurdle be cleared?


Figure 2: from  BlackRock Global Investor Pulse Survey  July/August 2015

Figure 2: from BlackRock Global Investor Pulse Survey July/August 2015

Clearing a $36,350 annual hurdle is achievable for an individual with experience, knowledge, talent and a willingness to work—the key traits of the average 50Plus individual. Chris’ original, English-language version of his book entitled The $100 Startup used the subtitle, "Reinvent the Way You Make a Living, Do What You Love, and Create a New Future", a perfect phrase to complete my call to arms to my 50Plus brethren. Chris was presenting the case for "micro-business" creation based on "micro-entrepreneurship". My only explicit additive would be a simple catalyst: understanding of the power of the Internet to reach almost any other human being on the planet with an offer. That is the basis of success for many "micro-entrepreneurs " today. 

In December 2013, I wrote a blog post entitled “Goal: Job Creation - Scalable Startups vs Micro-Entrepreneur Training.” The $100 Startup was one of three books I referenced. The primary target for the post was my class of millennial students at the School of Visual Arts in the MFA in Design for Social Innovation program. I was using the $100 Startup and Be a Free Range Human - Escape the 9 to 5, Create the Life You Love and Still Pay the Bills, by Marianne Cantwell, to explain the difference between entrepreneurial ventures aimed at launching "scalable" startups, requiring significant financial investment, contrasting them with the "micro-business" model needing, as the Manga translation says, "no money, no skill, just a tiny bit of an idea". Clearly, the first two books carried the micro-entrepreneurship message. The third book I cited was The Startup Owner's Manual by my friend Bob Dorf and his partner Steve Blank which emphasized the “lean” approach to building scalable startups.

A secondary target for the original blog post was government economic development officials. Besides teaching at SVA, I was acting as a consultant to the State of Connecticut’s Department of Economic and Community Development on the creation of a more entrepreneur friendly “innovation ecosystem” in the state. The marching orders of these folks in CT, and elsewhere, is to stimulate the creation of, or the import of, jobs, jobs and more jobs, preferably in fast growing industries. In my experience, when the question of how to do this comes up, the answer reflects economic developer's fondest dream, “we need a Facebook, a Google, an Apple, another Priceline (a CT company), some true high growth companies in this geography. We only need one or two to solve a lot of our job problems”. When pressed as to what they really wanted, the answer in CT was often "just take me to the NY Tech Meetup (where I was active in the Leadership Circle), introduce me to some of your friends and help me steal a few young scalable growth companies".

Lots of public money gets spent trying to seed or create the “conditions” for high growth companies based on the fantasy: they will create the lion's share of the missing jobs. I was challenging this thinking in my 2013 blog post by asking, "why not experiment with some portion of economic development funds by training people to create their own jobs by building micro-businesses"? I pointed out that entrepreneurship is not a genetic trait, it can be learned. Case studies like those in Chris' $100 Startup, Marianne's Be a Free Range Human or about friends of mine who have done it are the best way to teach it. The goal of my challenge: track how many individuals can create their own “jobs” as micro-entrepreneurs by leveraging their existing knowledge, skills and talents mostly via an effective use of the Internet. 50Plus individuals are the perfect test cases for this experiment today. I strongly believe that the “job market,” jobs created by others, especially by "high growth" companies, are not going to be the safety net for the 50Plus demographic. We must experiment. Let's explore the real power of micro-entrepreneurship to understand how it "scales".

This series of posts on the 50Plus demographic has been leading up to the launch of a new website, which I am almost ready to reveal. Historically, I built scalable startups but never a true micro-business. My mission is to build a micro-business in full view, demonstrating to the 50Plus demographic how to leverage one's knowledge, talent and experience, in my case as a serial entrepreneur, mentor and teacher. My goal is to help as many members of the 50Plus demographic as I can create their own jobs. I am not without my own role models. I have been following some carefully over time. They happen to be millennials and young Gen X'ers, folks like Chris Guillebeau, Pat Flynn, Marianne Cantwell and others who took the plunge and figured this out at different points in the last decade and are still doing extremely well. I will hopefully introduce you to some of them along the way. Their stories are amazing. Ours can be too!

If you haven’t done so already, subscribe to my e-mail list to receive notices of my remaining posts in the 50Plus series on this website and the announcement of my new website. I look forward to serving you and getting to know you in the process. Let's do this together!

Serendipity: A Perfect Ingredient to help Solve the Challenges Facing the 50Plus Demographic

   A "serendipitous" four peak day on Jan 10, 2016 near Portland, Oregon on a 2 hour drive never more than 45 miles from my front door all taken from Oregon vistas. Clockwise: Mt. Saint Helens, Mt. Rainier, Mt. Adams and Mt. Hood.


A "serendipitous" four peak day on Jan 10, 2016 near Portland, Oregon on a 2 hour drive never more than 45 miles from my front door all taken from Oregon vistas. Clockwise: Mt. Saint Helens, Mt. Rainier, Mt. Adams and Mt. Hood.

Serendipity was the subject of my first two blog posts in September and October 2013. Both posts were different takes on how we can create our own serendipity. I have been a long time believer in serendipity since I can point to a fair amount of it in my own life. I have had enough of it that I strongly believe there are a number of different ways you can increase your odds of experiencing it. I highly recommend conferences and other well chosen gatherings as starting points since they have been a primary source of serendipitous interactions with people, organizations and ideas that have changed my life. In most cases I likely would not have encountered them in any other way.

In 2015, as my focus for this blog shifted from millennials to the needs of the 50Plus demographic, I hadn't yet thought to touch on serendipity again. It was an article in the NY Times the week before last by Pagan Kennedy entitled Cultivating the Art of Serendipity that put it back on my radar screen. Her subtitle makes a point that caught my eye right away, "Innovation isn't all hard work or dumb luck: It's about paying attention". Kennedy’s timing was itself serendipitous because I quickly realized that I had overlooked that serendipity can be a key ingredient in helping the 50Plus demographic to face its major financial challenges in the coming years.

My message to the 110 million strong 50Plus demographic is this: we have to begin to embrace entrepreneurship to generate the additional income needed to overcome the structural problem of outliving our financial plans. In short, for many, “entrepreneurship will be a necessity, not a choice”. Just to be clear, when I use the term entrepreneurship I start with entrepreneurial thinking. Learning to think like an entrepreneur isn’t based on genetics, it is not a trait that you either inherited or you didn’t. It is a learned behavior accessible to all of us. I am not suggesting it is an easy learning curve, but I can speak from experience as a serial entrepreneur, as well as from teaching others, it can be done.

Tina Seelig, a leader of Stanford University's preeminent entrepreneurship program, provided a definition of entrepreneurship in her book Insight Out. In her words, “entrepreneurship involves building the knowledge, skills, and attitudes needed to see problems as opportunities and to leverage resources to bring ideas to fruition.” In her book, Seelig presents what she has dubbed the four part Invention Cycle. This cycle is  rooted in using curiosity to spur your imagination, which then seeds creativity to allow one to visualize innovations, which finally opens the door to the act of entrepreneurship to bring them to fruition. Seelig doesn’t mention serendipity. However, reflecting on the first part of Pagan Kennedy’s subtitle, “Innovation isn't all hard work or dumb luck”, I would suggest that "cultivated serendipity" is “smart luck”, which I assume is why Kennedy describes it as being, “about paying attention”. I would hold that smart luck based on paying attention is a perfect additive to the Invention Cycle. My gut says Seelig could agree with that.

The 50Plus demographic is loaded with experience, knowledge and well honed skills. Cultivating “smart luck” by paying attention with the right attitude seems like what the doctor ordered to get us on track to solving our own problems. If any demographic can do it, we can.

Having defined the scale of the problem in my last post, coming up with another key ingredient here, in the next few posts in this series I will explain my thoughts on how this all fits together and most importantly why I am confident that if we stay focused we can succeed in controlling our own destinies. It is not too late! I will share more details of my own experiences and those of others, including stories of folks who have cultivated serendipity in various ways to succeed as entrepreneurs. My focus is going to be heavily skewed towards micro-entrepreneurship, starting small to create our own jobs without taking huge financial risks. This is in contrast to trying to fulfill the dreams of economic development officials looking for the next Facebook, Google, Apple or sharing economy startup to create massive numbers of new jobs in their geography. I will emphasize that working smart in this day and age means acknowledging the power the Internet, not ignoring it. A few more posts will take us to the launch of my offering to the 50Plus community based on a new website later this month or in early February. I am excited to share it with you!

Stay tuned a little longer… the meantime please continue to comment here or e-mail me at




Finding Purpose: Good Advice at Any Age

In the past few days a repost of this Brain Pickings article from February 2012, "How to Find Your Purpose and Do What You Love", via a Facebook share, made a direct hit on me. Maria Popova has been a favorite blogger of mine since she and I first met in person on a NYC street corner across from Grand Central in 2009. I read this post in 2012 but hadn't remembered it. The direct hit was because my wife Noelle and I have been sorting through our options since moving to Portland, Oregon in December. We are both asking what's next, what should we do going forward? On the top of our list is "finding purpose", doing something we love, that will make a meaningful impact on the world. We are members of the 50Plus demographic and as we look ahead we assume our lives will span at least another 30+ years of healthy, engaged, active living. Therefore, "finding purpose", doing something we love, is critically important.  

Maria's post is so impactful because she pulled together insights on finding purpose from seven amazing authors. Paul Graham and Steve Jobs are two that I have long been a fan of. I read Paul's writing long before he became well known for Y Combinator and many of the now famous alumni of Y Combinator's acceleration process. I started following Steve Jobs' career in 1981 when I bought my Apple 2+ computer. Maria cites Steve's 2005 commencement speech at Stanford University which has gained fame from his reference to what has become known as "the passion hypothesis". Steve said, "Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven't found it yet, keep looking. Don't settle. As with all matters of the heart, you'll know when you find it." 

It turns out that the most recent book I read this summer, So Good They Can't Ignore You - How Skills Trump Passion in the Quest for Work You Love by Cal Newport, is the first serious writing I have read that dares to question "the passion hypothesis". How can anyone question it, who wouldn't want to find and commit to work that they love and why shouldn't they? Newport starts his cross examination of the passion hypothesis by making a very important point about Jobs himself:

“If a young Steve Jobs had taken his own advice and decided to only pursue work he loved, he would probably have been one of the Los Altos Zen Center’s most popular teachers. But he didn’t follow this simple advice. Apple Computer was decidedly not born out of passion, but instead was the result of a lucky break - a “small-time” scheme that unexpectedly took off.”
— "So Good They Can't Ignore You" by Cal Newport

Derek Sivers, my original source on Newport's book, highlights Newport's broader conclusion - "the passion hypothesis convinces people that somewhere there's a magic "right" job waiting for them, and that if they find it, they'll immediately recognize that this is the work they were meant to do. The problem of course is when they fail to find this certainty, bad things follow, such as chronic job-hopping and crippling self-doubt." A very sobering conclusion.

In the end Newport's well researched message is quite simple. It starts with the admonition not to obsess over your "true calling" rather take time to acquire "rare and valuable skills" which he describes in economic terms as "career capital". He goes on to say once you begin to earn career capital it can be "invested" to gain "control over what you do and how you do it". He finally suggests that it is the wise "investment" of career capital over time that will eventually help you to identify a "life-changing mission". However, that quickly begins to sound like a very long road. It can be for millennials or others who have not had or taken the time to amass sufficient career capital. However, for our fellow travelers in the 50Plus demographic the good news is that we are collectively overflowing with experience, talent and knowledge, lots of legitimate career capital in Newport's definition. Our biggest challenge is how to use it to find "purpose", a "life changing mission" or a "true calling", pick your term, without it taking too long.

On the subject of how to find a "life changing mission" Newport references Little Bets by former venture capitalist Peter Sims who describes his work by saying that Steve Jobs, Chris Rock, Frank Gehry and the story developers at Pixar all have one thing in common. They all have taken small steps, experimental ones at that. They didn't start with a big idea trying to foresee final outcomes but made little bets about what might be a good direction, learning critical information from lots of little failures and some small, but significant, wins that allowed them to find unexpected avenues to arrive at extraordinary outcomes. In Newport's view using the "little bets" approach, supported by career capital, to find a "life changing mission" is the prescription. 

As a serial entrepreneur, I see Sim's "little bets" approach as a takeoff on Eric Ries' lean startup method which I have been teaching in startup accelerator programs in CT, in the MFA in Design for Social Innovation program at School of Visual Arts in NYC and as a mentor to a handful of entrepreneurs in recent years. My shortened version to describe this approach to creating a successful business is, make a series of guesses about what to offer potential customers, which channels to reach them through, testing if they see enough real value in what you are offering to be willing to pull out their wallets. The key is to prove your guesses one at a time, if you are wrong, change direction by making a "pivot", and try again. Once all of your original or revised hypotheses have been shown to be true - facts instead of guesses - you are onto something that will very likely succeed if customers are willing to pay enough to cover your costs leaving you with a sufficient profit. My conclusion is that success in "finding purpose" is basically an exercise in "entrepreneurial thinking" using the "little bets" or "lean startup" approach to test hypotheses along a potential path to a "life changing mission". Done right you will get there.

My advice to my 50Plus demographic is that it is imperative that we all understand and incorporate entrepreneurial thinking as we set out to find purpose this time. I can help you. I will be expanding on this advice in more detail in a series of new blog posts during August and on a new website in early September. Stay tuned.

If you are new here, welcome. If you have read my intermittent postings before, welcome back. In either case please subscribe to receive a notice when I release new blog posts in this series but more important, be the first to know about my new website when it launches.

The Salvage Supperclub - Williamsburg Brooklyn

The Salvage Supperclub - Williamsburg Brooklyn

Salvage Supperclub is an outgrowth of a thesis project on food waste by Josh Treuhaft a student who received his MFA last month in the Design for Social Innovation (DSI) program at the School of Visual Arts where I taught entrepreneurship. Josh teamed with Chef Celia Lam of the Natural Gourmet Institute who prepared a menu that was out of this world all from ingredients donated from many food suppliers who otherwise would have thrown them away as unsalable items ("underused food") for their shelves.