Dreaming about the future is bad for your career

Carl Sagan once said,

Imagination will often carry us to worlds that never were. But without it we go nowhere.

I write a great deal about the future: the future of tools, the techniques we use to harness them, and the way the world will wag just over the next sunrise. I do so because I think this is helpful, and cracking open people’s minds to let those ideas seep in can have immense impact on them, and by extension, on the organizations where they spend their energies. But all too often, companies seem closed to those imaginings. Why?

One reason is that companies don’t really like dreaming and dreamers. Dan Pontefract relates the tale of his recent encounter with a friend, “Aaron”, a person with great ideas who gets knocked on his performance reviews for dreaming:

I asked how things were going in his role. (He works for a rather large organization.) That’s the precise moment his ear-to-ear smile shifted to a glum, forlorn frown.

“Dan,” my friend questioned me with a palpable display of meekness.

“Why is it I get penalized for dreaming on my performance review?”

It was at this moment I wished our lattes might have been mistaken for Irish Coffees.

“I’ve got ideas and thoughts for the future of this company — and for our customers — and yet my performance review stinks,” he explained further. “I’m told to focus on my presentations and my deliverables, but I never get rewarded for my ideas.”

He then added:

“I’m punished for dreaming.”

My heart sank.

Aaron is gifted. He’s a dreamer. He’s an innovator. He’s a thinker. It was clear to me his role if not career growth is being stunted and his ideas are being ignored. I can’t begin to fathom what fantastic and positive contributions he would make to his company if only he were permitted to dream; if only a portion of his performance development plan (ie. his objectives) were re-engineered to dream.

Dan goes on to make this a cautionary tale for business leaders. But I believe the issue isn’t just managers and leaders: it’s everybody. People are afraid of creativity in general, and especially in times of stress, where traditional approaches to problem are strongly favored, even when they don’t work.

And creative people are uniformly considered unsuitable leaders unless they couple that with high degrees of charisma, as I detailed in The cultural bias against creatives as leaders. In fact, this bias has been suggested as the root cause of why so many leaders fail, and why groups seem to resist change. We continue to select for leaders that are uncreative, who strongly favor tradition over innovation, and who inspire a culture that follows that lead.

The answer? Alas, I am not sure that there is one. Being a dreamer may be something like ‘following your passion’. As Cal Newport has observed, following your passion may be terrible job advice. In his thinking, passion has to be earned, over time:

Different people are looking for different things in their work, but in general, if you study people with compelling careers, they enjoy some combination of the following traits: autonomy, respect, competence, creativity, and/or a sense of impact. In other words, if you want to feel passionate about your livelihood, don’t seek the perfect job, instead seek to get more of these traits in the job you already have.

The problem, of course, is that these traits are rare and valuable. Just because you really want a job that allows you to autonomously tackle respected creative projects doesn’t mean that someone will hand it to you.

These rare and valuable traits require that you have rare and valuable skills to offer in return, and building these skills requires time and deliberate effort. If you’re unfulfilled in your current position, therefore, start by asking how you can become more valuable.

So, before you can get a job where you get to dream about the future, you need to sharpen your skills and share a lot of dreams that matter to others. Share your dreams, hone them, but don’t be surprised if you are sidelined because of them. You may need to intentionally take on the techniques of charisma to be considered a leader if you lead with ideas instead of traditionalism.

Sagan is right, that we rely on those who can imagine new worlds, devices, tools, or practices, but many of those dreamers pay a high price, and many of those dreams never see the light of day.

Leanership trumps leadership

Two university professors interested in entrepreneurship wanted to test the assumption that entrepreneurs are motivated by the potential upside of starting a gazillion dollar business. Hongwei Xu and Martin Reuf polled 60,000 people — entrepreneurs and normals — and what they found disproved the assumption:

Alvin Lee, The entrepreneur’s motivation

The study […] looked at two groups of people: those who have just started their own businesses versus the general population. To gauge their risk tolerance, these two groups were given three options for venture investments: “a profit of US$5 million with a 20 percent chance of success” (option 1); “a profit of US$2 million with a 50 percent chance of success” (option 2); and “a profit of US$1.25 million with an 80 percent chance of success” (option 3).

General perception of the risk-seeking, nothing-ventured-nothing-gained entrepreneur would dictate that most business owners would plump for option 1. But the study proved otherwise. More nascent entrepreneurs opted for option 3 – a higher chance of profit, but less of it – than the general population, while a higher proportion of the general population actually opted for option 1 instead of the business owners.

So if money alone isn’t enough to make someone start their own business, what would? “Creating a business is very risky, it’s very uncertain,” Xu told INSEAD Knowledge. “Non-pecuniary motivations are more important than monetary motivations for people to start a new business. One is autonomy: People want to be their own boss. The other is identity fulfillment, which is more about people having a vision about a product or a service. But their employers do not give them the freedom to develop within the company structure. That is a key driver.”

Intrigued, Xu corroborated that desire for autonomy and the self-identity that comes from being your own boss, heading your own way. He got lots of positive feedback from entrepreneurs.

Morra Aarons-Mele suggests that those who don’t know — the normals in the study above — are often intoxicated by the concept of entrepreneurship, or ‘entrepreneurship porn’. But the motivations of many of those drawn to entrepreneurial start-ups are in fact what Xu and Reuf discovered: they are seeking autonomy and are actively repelled by the idea of a soul-sucking job following someone else’s vision for a company.

Her stats are frightening, and stand as a condemnation of work culture today:

I’ve come to suspect that the rise of “entrepreneurship porn” is at least as much about escaping a company as starting one. Most Americans don’t like their work. Data on Americans’ dissatisfaction regarding their work – in corporate environments, in particular, show:

  • 2 million Americans voluntarily leave their jobs every month (Bureau of Labor Statistics)
  • 74% of people would today consider finding a new job
  • 32% of employees are looking for a new job
  • Only 47.3 percent of currently employed Americans are satisfied with their position (Conference Board)
  • The majority of American employees are disengaged from their work (Gallup)
  • Entrepreneurs are more likely to have an optimistic view about their futures than other employees (Gallup).

My hope is that we can attack this the other way. Instead of 75% of workers quitting their jobs, how about a revolution in work? What if companies adopt common sense, but radically innovative ways to get people reinvested in their own work, and through that to crack the code of socially-scaled engaged work across the company.


The deeper form of entrepreneurship is to put aside the mythic know-it-all genius founder archetype and adopt the new way of leadership: leanership. To adopt lean principles across the board, in the core tenets of work culture, and not just about the product cycle.

What is largely missing is an acceptance by today’s leadership to embrace a new open work culture: one that is deeper and broader than the inauthentic and propagandized closed organizational culture of most businesses. This new deep culture is based on the core principle that the people doing the work of the business are as important as the work being done, and whose wellbeing is as critical as the imperatives of the business. And, among other outcomes that means far greater autonomy, more opportunities to develop mastery in new skills, and a social climate in which people can earn and benefit from the respect of their peers.

I have a second concern about ‘entrepreneurial porn’, which often takes a dark turn once companies grow past the three-guys-and-a-dog-in-a-garage stage. The sense of being on an endless sprint — a demanding but noble mission — can lead to a stress factory, where people work ridiculous hours, and everyone is supposed to subordinate everything in their lives to the company’s vision. And by ‘company vision’ I mean the vision of a small management elite. In the evil twin version of inspired entrepreneurial culture, people that don’t ‘fit’ get fired. And culling all the misfits can be simply restated as closing off dissent and disenfranchising employees that want to have a greater say in the work they do and what it is supposed to be about.

I often characterize today’s standard organizational model as the entrepreneurial company. The hierarchy has been flattened, but there are at least two ranks: those at the bottom and those at the top. The vision for the company comes from a handful of people, and others are there to execute against that vision. Preaching about great culture in such companies is often a form of indoctrination, and ‘consensus building’ is actually intended to crush dissent, and organize everyone around the gamble the company’s leaders want to make with the companies capital and people’s labor.


This new deep culture is based on the core principle that the people doing the work of the business are as important as the work being done, and whose wellbeing is as critical as the imperatives of the business.

Taking a step back: the entrepreneurial marketplace is something like the way that fish and reptiles produce offspring. They create a lot of eggs and spend very little investment in them. This is how Silicon Valley and today’s start-up marketplace works these days: thousands of entrepreneurial companies are created, and 99% go out of business in short order. Which is fine at a macroeconomic level, but is hard on the people involved.

But mammals — especially the primates and other social mammals — work the opposite way. We have few children and we invest a great deal of time and energy to raise them to adulthood. So, if you are starting a company — to build software, wash people’s cars, or sell tickets to the Moon — you might want to run it — at least in part — like a start-up, using lean notions like experimentation instead of opinions, and testing markets by conversations and working with prospective clients instead of creating a five year business plan. But if you are as committed to people as you are to following your own Pole Star, the deeper form of entrepreneurship is to put aside the mythic know-it-all genius founder archetype and adopt the new way of leadership: leanership. To adopt lean principles across the board, in the core tenets of work culture, and not just about the product cycle. This may well be what Tony Hsieh is doing as he steers Zappo’s toward the adoption of Holacracy, which is a highly formalized approach to leanership, and which has also be adopted by Ev Williams at Medium.

We have a great deal to learn from lean thinking, and if applied to the the greatest extent, it undoes the conventional notions of a leader-centric business, where collective behavior is demanded and imposed through top-down consensus building (or squashing dissent). As I recently wrote in Today’s business organization is an oligarchy, and that needs to change, we need to move to much more democratic organizations, and soon:

There is still room for visionaries, as much as before. There will still be founders, and leaders, and owners. But in order to be fast-and-loose the notion of direct supervision — and the strong ties involved — must be diffused. Increasingly high performing staff will demand greater autonomy, and not for selfish reasons, but to get things done quickly. Companies will create, find, and retain top performers, and create the context for high performance. As before, the narrative will be legitimacy of the organizational structure by efficiency, but a much greater degree of democracy will be involved since all work participants will voluntarily select the work to be done, and who to work with, rather than being told.

So, in the final analysis, if we want to fix what’s broken in business — where 74% are disengaged at work — we can’t just start fungineering, or buy yet another new social tool. We need to rethink the foundations of work, and get people reengaged. Entrepreneurial zeal is both a help and a hindrance in this case, so we need to be clear on its two-edged nature.

Perry Hewitt falls right into her own trap

Perry Hewitt, the Chief Digital Officer at Harvard, recently produced a listicle for HBR, Five Mistakes to Avoid When Managing Digital Teams, and in the article she manages to fall smack dab into one of the mistakes she’s warning us not to make.

The last mistake in her list:

Mistake #5: Underestimating the speed of change. In 2003, blogging was still new in the mainstream, and mistrusted by corporations wedded to large CMS installs. In 2005, it was understood that video would never be a dominant form for readers. In 2007, mobile was mostly a development afterthought. In 2012, people insisted ephemeral content was a fringe use case, before Snapchat’s ascendancy among both preteens and Wall Street bankers. Managers must develop digital teams strong not only at rinse and repeat, but with adaptable skillsets and mindsets. Set the stage for expansive thinking about what’s possible through tactics as varied as shared bookmarking sites, lunch and learns, and guest speakers from different industries. Digital is full of examples of the unthinkable becoming the inevitable — and a default-open approach to new ideas helps your team adapt for these shifts.

Just to pull out the salient point, she says “Digital is full of examples of the unthinkable becoming the inevitable — and a default-open approach to new ideas helps your team adapt for these shifts.”

And in the previous list item, she says this:

Mistake #4: Prizing communications control over collaboration. When many managers entered the workforce, the company dictated the terms of communication. Paper memoranda were the top-down coin of the realm, and feedback upward was limited to select channels like town hall meetings. Woe to those managers who think that world still exists. While hierarchies of all kinds are alive and well — and will be with us always — work-related communications flows have changed dramatically. Ask your digital team the best way to communicate. Successful teams will likely use a flavor of collaboration software, whether that’s an explicit project tool like Apollo or a Google doc structure. Periodically, re-evaluate this decision. Has information sharing moved to instant messaging? To Twitter? Let your team vote with their feet, apart from security essentials. You have a better shot of retaining team knowledge if you’re optimized for the real ways information travels, and aren’t waiting for updates to the company intranet.

So, “While hierarchies of all kinds are alive and well — and will always be with us — work-related communications flows have changed dramatically.” I agree with her idea that managers should let people vote with their feet on what tools to use (and a lot of people aren’t waiting to be told to do so). But what about the possibility that hierarchies are not necessarily going to be with us always? Perhaps she is falling into the trap of underestimating the speed of change in the work revolution.

That may be unthinkable to a Chief Digital Officer who is used to working through a hierarchy, and whose leadership is based on power instead of trust and regard.

She’s so wedded to the cultural foundations of hierarchy that she probably never even considered that hierarchy is not a law of the universe but a social convention, like slavery or the divine right of kings, once central to civilization but no longer. And I bet she won’t invite me — or others — to be a guest speaker to discuss the inevitability of hierarchy’s fall, and the rise of the network.

Eddy Cue promoted to Apple SVP, Internet Software and Services

Apple’s executive team is undergoing some changes, and one of those changes is a promotion for Eddy Cue to Senior Vice President of Internet Software and Services. Cue will continue to oversee Apple’s online stores and iCloud and take on the challenge of iAd, too.

Tips for being a happy and satisfied web worker

It’s important to be proactive and figure out for yourself how your strengths and weaknesses drive your web working preferences. You can improve your job satisfaction and make you happier in your work by finding projects and jobs that play to your strengths and preferences.

ClusterShot: How a Startup’s Pet Project Became Profitable

clustershothomepageWhen Canada’s Silverorange started developing ClusterShot, a web site through which people can upload and sell their photos online, in May of 2008, it was nothing more than a side project members of the 14-person web development firm worked on in the evenings and on weekends. Today the service consumes up to 25 percent of Silverorange’s development time and is profitable.

ClusterShot earns revenue from selling annual Pro subscriptions, which cost $20 and provide users with their own personal photo store. So how did ClusterShot achieve profitability just eight months after it launched last November? I spoke with Silverorange CEO Dan James to learn about the company’s recipe for success. Read More about ClusterShot: How a Startup’s Pet Project Became Profitable

What is Remote Leadership?

lilduckThe barriers to working from home are usually human, according to Rosabeth Moss Kanter, who presents remote working as a solution for “business growth, working families, and a green future.” Kanter, a Harvard Business School professor, cites leadership as an important factor in successful remote working, saying, “People need clear goals, deadlines and performance metrics. Team members need trust and the ability to rely on and fill in for one another.”
This got me thinking about the leadership and teams I’ve worked with remotely. Most of my remote working experience has been in small teams or solo — there has been little of what I think of as traditional leadership. Read More about What is Remote Leadership?