A couple of my readers have asked what I’m going to do ‘for a living’ next. They’re curious how a guy who’s written a book on how to start your own business could be mostly still looking for his next career a year after leaving the last one.

It’s a fair question, and one that has a simple answer: I’m deliberately not following my own advice. If I were 25, just starting out, I’d have decided to set up my own business, and I’d be deep into the research needed to ‘find a need and fill it’. Having advised over a hundred entrepreneurs, I’ve got a pretty good nose for what the ‘market’ says it needs and can afford — these days that’s things like cost and risk management programs, help with outsourcing, assistance with regulatory compliance, exceptional salespeople, and some nose-to-the-grindstone specialists — but at age 53 these business-as-usual ‘opportunities’ don’t interest me in the least.

There’s also a need for the opportunities that do interest me, but the people who need what I wish to offer can’t, for the most part, afford to pay me. This article is an explanation of that quandary, hopefully with some lessons for those who have abandoned, or are thinking of fleeing, a job you hate.

At least until my pension starts (2009), my career choices will be a matter of trade-offs — what I want to do versus what people are willing to pay me to do. I represent these trade-offs on the chart shown above. The position of each of my ‘second career ambitions’ on the X (heart) axis reflects my passion for them, while the position on the Y (dollar) axis reflects how much they are likely to pay, and the colour (green for high, yellow for moderate, red for low) indicates my current competencies to do each of them. I recognize that most people have neither the luxury of time nor the option of trade-offs between what they want to do and what they have to do. I’ve been exceedingly fortunate, and if you’re currently struggling to find a job — any job, or to make ends meet in a position in which you’re under-employed, I feel for you — I’ve been there, and it’s hell.

If any of these alternatives were in the upper right corner of this chart, I would have pursued them first, and neither the chart nor the hours of work I have put into thinking about my next career would have been necessary. Almost all my energies thus far have been spent on projects #1-6, the ones I already have the credentials to do:

  1. Writing: My book Natural Enterprise, my second non-fiction book The Cost of Not Knowing, my novel The Only Life We Know, and also, perhaps, a new magazine and a newspaper column.
  2. Creative Solutions / Critical Skills Centre: Directing a think-tank, solution and training centre that facilitates these offerings for businesses and public sector organizations (including innovation and collaboration services and a mechanism to tap The Wisdom of Crowds) and uses some of the proceeds to extend these same offerings to non-profit organizations to enable them to solve some of the world’s most critical problems, and to school-children to equip them for the enormous challenges they will face in this century.
  3. Innovation Director: A one-to-two-year full-time secondment to an organization to provide its management and employees with, and implement, innovative ideas, training, facilitation and processes that make it a more innovative organization.
  4. Personal Knowledge Management: Working as a full-time consultant to one of the five major players in desktop productivity software, to help them capitalize on the enormous opportunity to provide comprehensive, integrated, simple personal knowledge management software, and hence breach the digital divide and ‘capture the desktop’.
  5. Personal Productivity Improvement and Working Smarter: A one-year full-time secondment to an organization to implement personal productivity improvement, bottom-up, one-on-one, for managers and front-line workers; or, alternatively, setting up an educational organization to offer these services to many organizations, or even to individuals.
  6. Knowledge, Learning & Technology Assessment and Strategy Services

I’ve made some progress on all six of these alternatives, but not enough on any of them to set the others aside and charge full-speed on just the one. Whereas my advice to others is to identify a known, unmet need and develop a product or service that addresses it, I’m taking the much harder tack of trying to persuade the buyers of these six leading edge services that there is a need for them, even though it hasn’t been articulated.

And if that wasn’t hard enough, I’m trying to ‘sell’ executives on services that primarily benefit their front-line workers, rather than the executives personally. Nothing tougher than trying to sell into a market where the direct recipients of the value aren’t the ones paying the tab.

The strategy I’m using for these is to work on all six in parallel, since it takes time to articulate the message and value proposition, identify the customers and make the pitches. And in each case what I’m selling is a novelty, so I need to ensure my audience is either thinking ahead of the curve, or sufficiently motivated by organizational crisis to entertain novel solutions. Without executive sponsorship and/or a sense of urgency, both of which are hard to find, selling an untested service, or creating a job for yourself, is virtually impossible. So I spend a bit of time moving each of the six forward a step or two each week, and I’m confident one of them will eventually ‘catch’. Status:

  • Some of my author contacts have been kind enough to recommend agents to me (and vice versa) for which I am very grateful. I’m just kicking myself for not thinking of this approach to #1 long ago.
  • I have pitched #2 to three organizations that have the wherewithal to pilot the Centre, but they’re hesitant to do so until there is proof of concept, which of course I can’t get until I get some resources — not all that different from the quandary of the first-time job-seeker (do I remember that anguish!) So now I’m looking for Champions — ‘name brand’ people who will vouch for the logic and viability of the process, to push the intrigued but hesitant investors to at least fund the pilot stage.
  • I’m using the Selling to VITO Headline Statementapproach to get the attention of CEOs of my ten targets for #3, using a very creative twist that I’ll tell you about soon — if it works.Meanwhile I’m doing a couple of innovation consulting assignments with a great partner.
  • My PKM approach for #4 is kicking around the intranets of three of the big five productivity software companies, and I’ve had some discussions with all three, but it’s tough. Despite the fact that my article on the subject was nominated as ‘best business blog post of the year’, it’s really tough leveraging that into a meeting with the powers that be in these huge organizations, but I’m still nagging them. If it happens, it happens.
  • I have a meeting tomorrow with some colleagues who I’ve been brainstorming #5 with. I’ve been astonished at the amount of interest there is on Getting Things Done and similar approaches to the ‘workflow management’ aspect of personal productivity improvement, and that employees are undertaking self-improvement on their own time and on their own dime — not waiting for their employer to invest. This is encouraging and we’re now exploring individual front-line workers as a second target customer group for PPI & Working Smarter services and resources. This is still in its early stages and I’ll talk more about it soon.
  • My fall-back is ‘KLT’ services — integrated assessments of organizations’ knowledge, learning and technology infrastructure and processes, and advice on related strategy. This is closest to what I was doing in my last job, and I’m good at it and have all the right credentials, but it doesn’t turn my crank as much as the other options. I’m doing a bit of this work now.
  • At one stage there was a #7 — teaching Natural Enterprise in universities. The prospective students and fellow profs I spoke to were both very keen, but my model (visiting entrepreneurial businesses with on-site Q&A, instead of lectures in class) was just too radical for the higher-ups in academia, who also said my lack of a PhD is also an obstacle. No point banging your head against the wall. This might conceivably still be part of #2 if the Centre wants to get into post-secondary education, perhaps in association with a private educational group like the Waldorf schools, but I’ve pretty much ruled out teaching at ‘established’ educational institutions. And, for now, community colleges don’t pay enough to support me, or this kind of a program.

Most of the advice online about second careers is old-line thinking, unimaginative, and demeaning or depressing. If you’ve found a second career, or made the decision to seek one, what has your experience, or your approach, been? Do you have any advice for others? We’re all taught to be dependent on the system, to participate in humiliating and nerve-wracking beauty contests for jobs where the odds are stacked against us — what methods have you found that help stave off the quiet desperation that is inherent in this loathsome and ego-destroying process? And if that’s not enough to prompt you to start your own business, what’s holding you back?

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  1. Dave;I think that you should apply to be an “Ashoka Fellow”. Here’s what they require:Ashoka Fellows must undergo a rigorous search and selection process in which they demonstrate the following attributes: * A big new idea * Creativity * Entrepreneurial quality * Social impact of the idea * Ethical fiber way you can follow your heart :-)

  2. Dale Asberry says:

    Dave,You “talk” too much! Get out there and just DO it. Regarding option #2… you’ve got a very diverse group of readers that are clearly savvy in their life pursuits. Your “place” for your think tank should be virtual and, as a start, you could possibly model it after the Iowa Futures Market. You could then use the think tank as a springboard for creating educational programs and consulting opportunities — or vice versa!

  3. Dave,I’m for Project #1 all the way. I think you should focus on writing and advocating by writing fulltime. You are simply too good and too insightful to be anywhere else right now. I believe that this blog is your entry point and that, as you have so well implied in “AMUSING OURSELVES TO DEATH? – MAYBE NOT,” your growing readership will likely be your best validator and your best advocate.The networking potential that the internet affords us is infinitely expansive. Likewise, the Conservation/Solar economy that is being restrained by the narrow and constrictive Corporate Empire is also infinitely expansive.Most of us who come here and dare to read and think are powerful pioneers and we shouldn’t discredit our potential. Keep giving us the benefit of your insight Dave. If you stay relevant, we’ll keep coming and we’ll bring our friends.If you need immediate funds, seek them through writing in more actionable laymans’ terms. Focus and intensify your intellect and its applicability. Promote yourself as a writer for progressive organizations and outlets. What about or the like? At any rate, keep expressing your talents openly. Future “think-tanks” come along, and will need people like you as staff leaders and representatives. Don’t try to make the wave. Position yourself to catch it when it comes.I know you know all this… and I don’t know half of what you know, but as a loyal reader, I think I know what you’re best at.

  4. Dave Pollard says:

    Harold, Dale, Dave: Thanks for the moving and wise advice. I guess the one thing I should have clarified is that I have a wife who’d like to retire, a dear sweet dog, and (although I have no mortgage), a house in a neighbourhood that I treasure, which requires some expenditure and upkeep. My wife’s more conservative than I am, and not interested in pulling up stakes and going out and changing things, which I respect, so both the physical commitment and low remuneration of Ashoka, and some of the other things I might otherwise be inclined to do if I had no personal commitments, are in a practical sense out of reach for now. Once ’09 comes, anything is possible, but that’s too far ahead to be thinking about right now. And while Dale is right that my constant analysis borders on anal, I’ve found research, doing my homework, has saved me from making serious mistakes more than once. Dave, thanks for the FT article — I’ve done some research on Soros et al and his dual focus right now is short term: getting Democrats back in power in the next four years, and helping humanitarian orgs deal with the immediate crises their facing especially in the Third World. There’s not much appetite to sponsor projects that are taking a longer view, which is understandable, and human nature. I really do appreciate the counsel, including that from those who e-mailed me in response to this post.

  5. Derek says:

    Well, I’m working on a second career in metal work, so at this point I’m just building skills and accumulating tools (metalworking & welding have *lots* of tools). To get the experience, I’m building anything I can think of and helping other students with their work. Down the road I expect to be able to point to past projects as a way of qualifying me for work. Another thing that goes a long way in my community is personal contacts, so meeting people and making friendships in the business seems to help too.

  6. Alex says:

    Hey Dave,I’m 25, looking to start my own business and these ‘bussiness as usual’ opporunities totally interest me, so if you have any ideas you are discarding feel free to get in touch :)-alex

  7. Jon Husband says:

    You’ve accomplished a hell of a lot in one year, and no doubt you know yourself better than ever … no mean achievement, that.

  8. Tes says:

    I like the idea of creating a market for stuff that interests you combined with getting paid (well) for what you are good at (think Bill Gates). One challenge I’m having with your blog (I discovered it not long ago) is that there is SO MUCH EXCELLENT STUFF, I’m struggling to synthesize it all. Echoing the sentiments of one of your readers, I’d like to see you focus and intensify your intellect into something that is readily applicable. I don’t know what that means, exactly, but I trust that you will figure out what to do with this input.

  9. Dave, your struggle is more common among people in their fifties than society wants to acknowledge. Interests and frustrations with career aren’t the only factors creating the need to recreate our careers. Social pressures that favor young adults fresh out of college, high on energy and chutzpah, and natural beauty also affect the flip side of the career coin. Our age, baggage, mortgages and cautionary tales make us less appealing on the “beauty circuit” as you call it. I’m also making a career change and am discovering the power of “leveraging”. My interests are secondary to how i can leverage my resources in a new direction. The quiet earthquake that happens in a career around age 50 is part of a natural cycle… when a forest fire burns off the productive vegetation, the bare earth is then vulnerable to “normal rains”. The landscape loses the wildlife that spreads the seeds…etc, etc. etc. We need to look at nature’s regenerative powers and apply them to our own human productivity careers. By burying seeds for times of emergency, we can then sprout those seeds when opportunity (time, forced solitude, etc.) give them space in which to sprout. That’s where leverage comes in. Making the most of what we have. Starting with small sprouts, taking time to grow, sinking roots deep in our layers of long-term, nurturing soil. My own career shift is into movie making. I’m appying my marketing skills to independent movie making. (Your feedback on my new web site is welcomed and will be helpful.) I’m finding that storytelling is a vital link in our social chain and that indies are struggling to bring diversity to our consciousness when studios and networks are narrowing their views. And that marketing is one of the indie producer’s highest barriers to thriving. I’m leveraging location (in Los Angeles), contacts, past experience, cultural knowledge, new media, creativity, and lots of networking to sprout a productive gardenspace in this new career space.One of my early alliances is with a fellow career changer and we are forming a production company to produce our own projects (break out of the established “beauty pagent” system). We have a combined slate of 9 screenplay projects and have now produced our first short. You can track our progress at And if anyone knows of anyone who believes in the value and power of storytelling as “continuing education” in our modern culture — we’d love to connect. Indies need investors and patrons who want to help fertilize diversity, quality and a shared vision of tomorrow. My marketing services and production activities will help connect people with compatible visions….both through our productions and those of other indies.

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