As a career management advocate turned Entrepreneur Evangelist, I recently had an epiphany that clarified some of the change I’ve experienced over the past two years, as I’ve moved from my old life to my new one.

I’ve been lacking an effective metaphor to describe both the process and my present (and potentially future) state.  This has been tremendously frustrating (for both me and my husband), because my state of mind on this journey radically colors the choices that I am (or am not) comfortable making.

I think I finally figured out how to define it more effectively  We often talk about a “career path.” I think this is inaccurate. I think the right phrase is a “career highway.”

Right Lane = Stability-Motivated Employee

• One career and as few employers as possible.
• Stability reigns supreme.
• Even calculated risks are uncomfortable.
• Large enterprises and government positions often appeal most to this category.
• A single employer career with a stable retirment plan and reliable benefits is the Holy Grail, and boredom is acceptable at work in exchange for stability.
• Any necessary excitement can be sought outside of work when needed.
• “Progress” is most frequently measured in proximity to retirement, more than rungs climbed up a career ladder.

Second Lane = Migratory Employee

• The modern normal.
• An employee who will have 2-4 careers in a lifetime, and an average of 12-15 different jobs.
• Stability is important, but not above all else.
• Calculated career risks are worthwhile, if not occassionally exciting.
• Jumping to a new job is always a possibility if a more appealing opportunity presents itself.
• This employee is often heavily motivated by autonomy and new challenge, secondarily by money.

Center Lane = Freelancer

• The newest class of employee, often placing a premium on freedom and flexibility above stability.
• Often easily bored, and prefering variety with risk to stability with stagnation.
• Commonly enjoys being a solo entity, and is disinclined towards growing a business that requires taking on the responsibilities of having employees.
• Collaboration with other freelancers is often a successful and preferential model.
• “Dollars for hours” is the most common financial model, which can cause business development challenges.

Fourth Lane = Self-Employed

• Small businesses, often family or small-team owned/managed.
• Frequently limited in scalability.
• Often heavily reliant on founder(s) for success.
• Lifestyle businesses and brick-and-mortar neighborhood businesses often fall into this category.
• Not uncommon for an owner to discover that they ‘own a job’ rather than ‘own a business.’
• Freedom and wealth-building often started out as core priorities; over time, the realities of business limitations can undermine those objectives if this was not the intended final growth state of the business.

Left Lane = Business Owner

• Scalable businesses of all sizes.
• Owner/founder has decentralized systems, processes and critical knowledge enough to allow for empowerment and delegation among staff.
• Vacations and sick days for the founder are possible and cause little in the way of organizational chaos.
• This business is a strong candidate for potential sale, since success is not wholly dependent on the original founder for success.
• Owners/founders who build this type of business can/do often build more than one over the course of their lifetime.

Obviously this isn’t an entirely clean mapping, and different combinations can blend a bit to create a bit of a hybrid. But I think that the most meaningful part of the highway metaphor is the idea that people can change lanes over time. Different life factors can influence which lane someone chooses.

• I have seen dozens of female Second Laners have children, and then suddenly switch into either Right or Center Laners (depending on both their personality and their skillset).
• I have watched numerous Second Laners get laid off and decide to take on an entrepreneurial opportunity by moving immediately to the Center Lane, sometimes working their way farther over as time goes by.

This has been my path. I was an obsessive, workaholic Second Laner who was finding a ton of meaning and fun in the career that served me well, paid me nicely, stroked my ego constantly and took me on great professional adventures for a decade. When I hopped off the highway to move to a new town, I (arrogantly) assumed that I’d be able to just hop onto the new road in my new town without any trouble, and slide right back into the Second Lane again.

Unfortunately, my timing sucked. We left New York for Texas the week that Lehman Brothers decided to implode under the weight of their reckless decisions, and all of my pre-move job interview work collapsed with it. While not technically laid off, I found myself in the same position as many people who were: I was suddenly at loose ends with an inability to find a company that would let me do what I knew how to do. So, I shifted to the Center Lane.

The reality, though, is that at the time we started our business, I used the language that I knew my husband wanted to hear: and it was all Left Lane language. That’s what he wanted, that’s what he was going for, and that’s how we discussed it. The problem, of course, was that — like many new Center Laners — my hope was to bide my time until I could jump back into the Second Lane.

After a rough few months, I was finally given that chance. And, as luck would have it, it was on a trial basis. My new employer wanted the chance to check me out, and I certainly wanted the chance to check them out. As it turned out, that was the best thing that could have happened to my Career Highway Navigation. Going from the Center Lane back to the Second Lane suddenly felt painfully confining. Stifling, even. I was miserable within a week. I never saw that coming, and was a bit shocked to finally get what I’d wanted only to discover that I didn’t want it anymore.

So, after informing my employer that I didn’t foresee being able to sufficiently fill their needs, I stayed around to help them hire my replacement and then ultimately left. Back in the Center Lane again, I was at loose ends once more, but this time with a purpose. I just had to figure out how to make it work.

During this time, my husband began working on his startup. Everything about my husband is Left Lane. The idea of any other kind of business simply doesn’t make sense. And as a deeply collaborative person, he recognizes that he’ll need help to build a business that fits the bill.

Yet when it comes to me, in my professional life, I’m still in the Center Lane. I know that I don’t want to be in the Fourth Lane. But I’m honestly not sure that I want to be in the Left Lane, either. There are variations of the Center Lane model that are more lucrative and more sustainable than a strictly ‘dollars for hours’ model (which I also don’t want), but I’m not at all convinced that I can’t attain the degree of freedom I am looking for, accomplish the wealth-building I seek and manage to stay in the Center Lane.

But then, that’s part of the point: my A-#1 priority is freedom, above all else. I am not risk adverse (obviously), and I enjoy primarily being an individual contributor who occassionally collaborates on larger projects with others; I also don’t want to go back to managing people, projects, processes or products (been there, done that)… but I also don’t want to go back to working for anyone else. Given that, I don’t really see a solution other than the Center Lane for me.

My husband’s priority is to change the world, build a team of empowered collaborators and inspire the people who come into contact with his business to find creative solutions to large-scale problems. This is a goal he could never accomplish from the Center Lane. To do this on the scale that he wants, he needs to be in the Left Lane.

I always like the way the Left Lane looks. But I am increasingly less convinced that I’ll ever necessarily make my way all the way over there. But I’m also increasingly less convinced that I necessarily need to. With some proper planning and organizing, I could find that the Center Lane is the place that I’m happiest. Only time will tell. I just hope that next time I find myself switching lanes, I’m aware of it in time to turn on my blinker.

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Last spring, I was reading the annual WorldBlu list of the most democratically run organizations in the world. One of the companies that caught my eye was one whose democratic organizational practices included eliminating a formal vacation day policy.

I remember making a mental note of the idea, because I liked it and wanted to keep it in mind as part of our plans for developing our business over time.  To me, it seemed like a logical extension of the Results Only Work Environment (ROWE) concept, which has proven very effective at large companies like Best Buy, while having always been — at least to some extent — a natural part of my career DNA at almost every company I’ve ever worked.

This debate has recently been kicked into the spotlight, thanks to Netflix fairly high profile stand on this position — what started off as a simple presentation (see below) describing their corporate culture, quickly turned into a big debate on the specifics of their vacation policy.

A recent article in Business Insider, Henry Blodget inspired a great deal of commentary when he asked readers what they thought of the idea — most of the responses are in opposition to the idea of a no-policy policy around vacation days. On Entrepreneur.com, author Tanya Payne added a fairly dismissive comment by asking, “Is Netflix run by a bunch of hippies?”

I’m fascinated by this debate, in large part, because in my experience as a white collar, tech professional is that — whether or not it’s “official,” every place I have ever worked has done precisely this. The reality, however, is just that: this is not something that places with hourly staff, or huge organizations are likely to find either appealing or even terribly practical.  So, for me, the question is not, “Does a ‘no vacation policy’ policy make sense?”  But instead, “When does a ‘no vacation policy’ policy make sense?”

As someone who works in a geographically independent profession on dynamic, project-specific, virtual teams with entrepreneurs and small organizations, this is sort of an obvious no-brainer. Even more importantly, what I like best about the idea of a ‘no policy policy’ when it comes to vacation time, is the fact that forces team accountability: either the person taking a vacation makes the necessary arrangements to be covered while they are out, or the person who hired them has to acknowledge that their staff is not mature enough to handle the responsibility of being treated like an adult — in which case, whether or not that person should stay needs to be asked and answered.

I also like that it eliminates what can seem like arbitrary favoritism in a crisis. Several times in my career, I have seen different sides of this equation, and all of them support the reasoning behind a no policy approach:

• A co-worker’s husband had a massive heart attack and, as a result, she was out of work for about a month. She had neither the vacation nor sick days accumulated to cover her time off, but no one for a second questioned that. She needed to be home with her family, and — even more importantly — now that their income had just suffered a massive (and indefinite) hit, the last thing she could afford to do was to have to chose between paying the bills or taking care of her husband and kids in the wake of a family crisis.
• As I was leaving another company, my final paperwork indicated that I had a negative number of vacation hours, based on my accrual rate and the amount of time I’d been with the company. However, the person handling it “wasn’t going to make a big deal” about it, and let it go without docking my final paycheck the even out the number of hours in my vacation bank.
• During a particularly high stress time in my years with another company, my boss — being both perceptive and prudent — recognized that I was overly taxed and at the end of my rope. With a non-negotiable Thursday morning instant message, he effectively kicked me out of the office for the following week and told me to clear my head, get some rest and that he didn’t want to see me until a week from the following Monday.

In each of these cases, the “official” policy said one thing, but the culture of the organization over-ruled it when circumstances arose. I think that doing this is far more dangerous — and potentially rife with conflict — than simply stating, “We do not count your vacation hours. Be a grown up. Plan accordingly, and work with your team to make sure your responsibilities are covered.” Because at least that policy sets the expectations.

The problem with exception-based end-runs around official policies is that you can’t prevent them. But, worse yet, they are fickle. It depends on the people involved, their relationships, the timing, their responsibilities, etc. That is where I see the vast majority of unfairness playing out, because there is no way to stop someone from working out a special arrangement because of “special circumstances.” The trouble with that, though, is who defines what the special circumstances are, which ones warrant a special deal, and what happens when someone else’s “special circumstances” are dismissed as less worthy of special arrangements?

Of course, the flip side in my universe is that I am a workaholic who seeks out high-chaos environments where no one ever only works 40 hours per week. I also specifically work in smaller organizations with a lot of flexibility, where working from home is standard, and where expectations are different. If there is one thing I learned working in the airline industry, it’s that there are different rules for hourly customer service teams than there are for backoffice salaried teams. Is that fair? Probably not. Is it avoidable? If it is, it’s probaby only possible while an organization is still small. (And even then, I’m not sure I’d be willing to bet the ranch on that.)

So, while I find the debate over the no vacation policy issue intersting, I guess what I mostly find is that it’s ignoring a tremendously important factor: it depends on your team, your culture, your services and your business. As with many things, the smaller the organization, the easier some of these things are to manage this way. Often times, stricter, formal policies arise out of a need for clarity that comes from too many different managers managing too many different teams that have too many different people. Clarity is a security blanket.

I think there are better ways to accomplish that clarity that are both more fair and more respectful, but a formal policy can definitely have its value. But then again, so too is there value in a boss recognizing that a member of his team is burned out and needs some time off, whether or not they have the official hours banked to take it.

I guess the real key boils down to three vital questions:

1. What kind of business do you want to run?
2. What kind of people do you want to hire?
3. And what kind of boss do you want to be?

It is probably only with a specific combination of answers that a no vacation policy can make sense. But, I’d venture to say that where it does make sense, it’d be hard to find a really good reason not to do it.

This post originally appeared as part of my Entrepreneur Evangelist series on WorkingPoint‘s Small Business Blog.

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As my year-end consumption of ‘top ten lists‘ continues, I came across one on Chicago Now called “The Top 10 Small Business Trends of the Decade” by Barry Moltz.  In the list he mentions several things that have all dovetailed together to define the changing nature of work — most centered around the pros and cons of mobility.

While I certainly wouldn’t argue that his list is wrong, it is very similar to several others I have seen, and I continue to think these lists are only peeling back the first layer of the onion.  Barry’s list includes items in three basic, separate categories:

Mobility:

• The internet allows geographic independent sales and marketing.
• The movement to reduce costs and commuting by working at home.
• Mashing of work and home spaces.

Social web:

• We are more easily able to network and keep in touch with people from our past.
• Size no longer matters.
• Customer Service makes a comeback.
• You are your own brand.

New economy:

• Less credit, more cash is king.
• Less benefits, higher deductibles.
• A new class of employee appears.

The details that Barry highlights in each of his bullets just grazes the surface of these bigger buckets.  And, even more significantly, these are revolutionary social changes that effect all business, not just small business.  What I find more interesting is their unique influence on small business versus their broader social impact.

Mobility
Obviously there is no one who has to be convinced that the second generation of the internet, with it’s capacity for permanent mobility, has changed everything.  Socially it means that states and municipalities have to pass new laws about using cell phones while driving; large business has to implement both policies and infrastructure to support workforces that are increasingly likely to be conducting work outside the corporate firewall; and small businesses can get up and running without having to see their opportunities limited by where they prefer to live.

But the bigger implication about mobility for small business is, I would argue, “the cloud.” Cloud computing (in its broadest definition), and specifically Softward as a Service (such as WorkingPoint, VerticalResponse and Business Online Payroll), is a double-edged sword in the world of small business.  Not only has it made tools and resources that used to only be available to big companies financially accessible to small businesses, but many of these companies are themselves small businesses.

The fact that a couple of developers with a great idea and some solid experience, can now leverage enormous outsourced technology infrastructure to build, host, manage and ultimately distribute their product to anyone in the world is revolutionary.  The cloud has extended everyone’s reach and has eliminated several of the biggest barriers to entry that existed when I started working on the technology space back in 1996.

The Social Web
This, of course, is this year’s hottest topic.  The social web went from being an outlier, specifically and uniquely for either early adopter tech geeks or Gen Y young’ins, to being super hip mainstream, ‘cutting edge’ mass media.  As Barry notes in his list, this has made a huge impact on how brands need to function in order to maintain their integrity — both on a personal and a business level (re: his points about customer service and company size).  But what’s the real seismic shift here?

The true impact of the social web is privacy.  Or, more accurately, the line between private and public.  Never before has it been more blurred, and it’s going to get more confusing before it gets less so.  Therapists will often point out that it only takes one person in a relationship to change the entire relationship dynamic: if you change your behavior, then it forces the other person’s behavior to change as well.  This principle is seen daily on the social web.

When customers change their behavior, it forces business to change.  Hence changes we see in the realm of customer service: a person can complain about a brand experience they had on Twitter, and see anything from immediate resolution to a lawsuit, depending on how the brand in question decides to handle things.

When employees change their behavior, it forces employers to change.  Businesses cannot reasonably ask their employees not to participate in the social web.  So how do they handle react when one of their employees becomes a bit of a social media celebrity, whose personal brand radically out-shines the company brand?

When citizens change their behavior, it forces the government to change.  “Transparent government” and “Gov2.0″ are two other key watchwords from 2009 that were nearly unheard of a year ago.  But now that individuals have come to expect to know things about the companies they deal with by virtue of online information, that expectation has transfered to government activities as well. Two years ago, who would have thought that Congress would have it’s own YouTube channel?  Or that a presidential candidate’s success could have been largely impacted by the use of Twitter?

Where is the line between private and public?  Tools that started out as personal use tools (e.g. Facebook and Twitter) are now platforms for business innovation.  The line between the two is different for everyone, and that creates a challenge, because the choices that one person makes will impact other people, whether those other people like it or not.  How many times have you seen someone post a picture to Facebook or Flickr that includes other people who may not have wanted the picture posted?

There is a certain amount of privacy that a social web automatically steals from us.  The questions are how much is necessary, and then how much is comfortable.  The tricky part is that depending on the application and the person, those answsers change.  And only being in the first generation of the social web, we are a long way from sorting out those pesky little details.

New Economy
My favorite topic of all, is the new economy (which I would define as the economic realities inherent to our modern lives as a result of, among others, the two factors above: mobility and social web).  But this is also the one that is routinely most difficult for people to get their heads around, because the ripple effect is pervasive, throughout every facet of our lives.

Old definitions no longer apply: “conservative” versus “liberal” are ill-fitting labels in a world of updated economic and social conditions that re-draw the political lines without even trying.  Words like “stability” and “security” are no longer applicable to the job market, after three decades of being considered the corporate Holy Grail.  And in a nation that was spurred to global dominance on the back of an Industrial Age economic engine, a nation of “knowledge workers” now routinely offshores work to less expensive parts of the world on a daily basis.

There are some pretty enormous downsides to the new economy — no more pensions, no more covered healthcare, no more job security.  But there are also some amazing opportunities in it — no more being stuck having to live someplace you don’t want simply because of its proximity to your job, no more expectation of having to let someone else define your rise up the corporate ladder on their terms and timelines, no more wistfully dreaming of being your own boss because it costs too much to start your own business.  Think of it like sky-diving: for some people it represents the most terrifying nightmare imaginable; for other people it is the single biggest thrill they could ask for.

As with most change, the pros can be just as compelling as the cons, depending on your point of view.  Socially speaking, the new economy means that goods and services that used to be out of reach for the average person are now vastly more affordable — everything from international travel to high tech toys.  For large enterprises, the ability to offshore entire divisions of your business means huge cost savings, and leaner in-house talent able to focus on the most high-value added functions.  For small business, the ability to dynamically pull together freelance, geographically distributed teams to execute on projects as needed, means being able to compete with larger firms without having to take on the overhead of formal staff.

So, yes, Barry’s list of small business trends is technically accurate.  But the reality is that the changes his list represents are even bigger.  And the reason they have such an enormous impact on small business is that these factors have already fundamentally shifted the social foundations on which small business is built.

This post originally appeared as part of my Entrepreneur Evangelist series on WorkingPoint‘s Small Business Blog.

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I love startups. I love the chaos. I love the insane hours. I love the energy. I love the types of people who are attracted to work on high-risk ideas with long odds. I love the culture that evolves around them. I love it all. I have spent my career hopping from one startup to the next, because there is nothing I love more.

But every startup hits a tipping point, and it’s rarely articulated as clearly and beautifully as Steve Blank does in an article posted to VentureBeat today. The transition from a ‘scrappy startup’ to a mid-sized company trying to be more mature is always infinitely more painful a process than anyone seems to think is reasonable.

This surprises me every time I see it. In his story, Steve recounts watching a new CFO to a mid-sized firm implement a ‘no more free soda’ policy and inadvertently spark an exodus of the founding team of engineers. What’s more interesting, though, is that some of the comments posted on the story miss the point: the engineers didn’t leave the company because the company started charging them $.50 for a Coke. The engineers left because being charged $.50 for a Coke was a sign that the company was no longer the same organization that they’d previously been willing to sacrifice for.

That’s a subtle distinction, but a vital one. More than once, I and many of my colleagues, have been willing to take significant pay cuts to work in environments that had a culture (or other intangibles) that made the trade-off worthwhile. Eventually, though, most organizations change enough to where that trade-off ceases to be worth it. The part that is often upsetting, however, is that those changes are frequently sparked by someone coming in the door more intent on shaking things up than on understanding the culture they are walking into.

Steve’s story is one that I can relate to over and over again. It wasn’t until I had a truly remarkable executive come into our organization, and refuse to act precipitously, but instead insist on watching and interviewing the entire staff for his first 60 days, that I had the slightest hope of someone making positive changes without unraveling the cultural elements that held us together, even in the face of the chaos. So now, when I go into startups, many of which are at the transition point between early-stage/founding team, and their second generation, I have a five step approach I follow:

1. Recognize that, for founding teams, everything is personal. The people who build a new organization take on a lot of risk and chaos to do it. They have to believe in it. It’s almost a religious experience, and you can’t come in a year or two later and expect them not to take your changes personally. Because, whether it makes sense to you or not, everything is personal. They’ve sacrificed too much for it not to be.
2. Understand the evolution. You have to be a bit of an archaeologist when you go into a new business. Do not make assumptions about how they got where they are. If you look long and hard enough, talk to enough people, and do your research, you’ll find that even the craziest things you see have a reason for having evolved the way they did. Unless or until you understand that reason, anything you do to try to “fix” the situation runs the risk of alienating people unnecessarily.
3. Respect the sacrifices made by the people who came before you. Unless you know that the people who are there when you walk in the door are dead wood and you want them to quit, make sure you demonstrate some respect to what they were able to accomplish — especially if they did it under tough circumstances. The single biggest source of alienation I have ever seen has been when new people come in, hot-to-trot, making changes and the people who built the company in the first place are treated like morons who simply got lucky.
4. Work on depersonalizing the business. It is reasonable that early stage startups are often personal sacrifices for people — they need to be. But a maturing company has to pass the point where that is no longer true. Not all of the early stage team will be able to handle that transition, but many of them can and will if they do not feel kicked in the teeth by new leadership brought in from the outside. Slowly building in an ethic of, “It’s not personal, but this is where the business needs to go now” is actually often much easier than people assume it to be. Founding teams want the business to be successful. That was the whole point for their sacrifice. If you want or need them to stick around, then help them learn to take a step back and not see the evolution of the business as an emotional affair.
5. Facilitate relationships between the old guard and new guard. Not all of the old guard is (or should) make the transition to the new phase of the business. And not all of the new guard is capable of showing any respect for what the old guard has done. But if you focus on individuals, their talents, and understanding what drives them, it is often possible to help connect people in ways that build strong teams to move the company forward. But you must keep in mind that there is often an automatic lack of trust between both groups, a tendency to point fingers, and a common tradition of resentment that you must work through before you are going to see progress.

Businesses are made up of people. And not every person is right for every business at every stage. Some really do need to move on as an organization grows. But that should be a deliberate, well-considered decision, not a haphazard, expensive mistake spurred by a short-sighted, penny-pinching reason. Unfortunately, that’s the cause I’ve seen most frequently throughout my career. And it’s a bit tragic, because a lot of dynamic organizations have lost a lot of amazing talent that could have helped grow the business and make it successful.

(This post is part of my Entrepreneur Evangelist series and was originally published on WorkingPoint‘s Small Business Blog.)

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As my year-end consumption of ‘top ten lists‘ continues, I came across one on Chicago Now called “The Top 10 Small Business Trends of the Decade” by Barry Moltz.  In the list he mentions several things that have all dovetailed together to define the changing nature of work — most centered around the pros and cons of mobility.

While I certainly wouldn’t argue that his list is wrong, it is very similar to several others I have seen, and I continue to think these lists are only peeling back the first layer of the onion.  Barry’s list includes items in three basic, separate categories:

Mobility:

• The internet allows geographic independent sales and marketing.
• The movement to reduce costs and commuting by working at home.
• Mashing of work and home spaces.

Social web:

• We are more easily able to network and keep in touch with people from our past.
• Size no longer matters.
• Customer Service makes a comeback.
• You are your own brand.

New economy:

• Less credit, more cash is king.
• Less benefits, higher deductibles.
• A new class of employee appears.

The details that Barry highlights in each of his bullets just grazes the surface of these bigger buckets.  And, even more significantly, these are revolutionary social changes that effect all business, not just small business.  What I find more interesting is their unique influence on small business versus their broader social impact.

Mobility
Obviously there is no one who has to be convinced that the second generation of the internet, with it’s capacity for permanent mobility, has changed everything.  Socially it means that states and municipalities have to pass new laws about using cell phones while driving; large business has to implement both policies and infrastructure to support workforces that are increasingly likely to be conducting work outside the corporate firewall; and small businesses can get up and running without having to see their opportunities limited by where they prefer to live.

But the bigger implication about mobility for small business is, I would argue, “the cloud.” Cloud computing (in its broadest definition), and specifically Softward as a Service (such as WorkingPoint, VerticalResponse and Business Online Payroll), is a double-edged sword in the world of small business.  Not only has it made tools and resources that used to only be available to big companies financially accessible to small businesses, but many of these companies are themselves small businesses.

The fact that a couple of developers with a great idea and some solid experience, can now leverage enormous outsourced technology infrastructure to build, host, manage and ultimately distribute their product to anyone in the world is revolutionary.  The cloud has extended everyone’s reach and has eliminated several of the biggest barriers to entry that existed when I started working on the technology space back in 1996.

The Social Web
This, of course, is this year’s hottest topic.  The social web went from being an outlier, specifically and uniquely for either early adopter tech geeks or Gen Y young’ins, to being super hip mainstream, ‘cutting edge’ mass media.  As Barry notes in his list, this has made a huge impact on how brands need to function in order to maintain their integrity — both on a personal and a business level (re: his points about customer service and company size).  But what’s the real seismic shift here?

The true impact of the social web is privacy.  Or, more accurately, the line between private and public.  Never before has it been more blurred, and it’s going to get more confusing before it gets less so.  Therapists will often point out that it only takes one person in a relationship to change the entire relationship dynamic: if you change your behavior, then it forces the other person’s behavior to change as well.  This principle is seen daily on the social web.

When customers change their behavior, it forces business to change.  Hence changes we see in the realm of customer service: a person can complain about a brand experience they had on Twitter, and see anything from immediate resolution to a lawsuit, depending on how the brand in question decides to handle things.

When employees change their behavior, it forces employers to change.  Businesses cannot reasonably ask their employees not to participate in the social web.  So how do they handle react when one of their employees becomes a bit of a social media celebrity, whose personal brand radically out-shines the company brand?

When citizens change their behavior, it forces the government to change.  “Transparent government” and “Gov2.0″ are two other key watchwords from 2009 that were nearly unheard of a year ago.  But now that individuals have come to expect to know things about the companies they deal with by virtue of online information, that expectation has transfered to government activities as well. Two years ago, who would have thought that Congress would have it’s own YouTube channel?  Or that a presidential candidate’s success could have been largely impacted by the use of Twitter?

Where is the line between private and public?  Tools that started out as personal use tools (e.g. Facebook and Twitter) are now platforms for business innovation.  The line between the two is different for everyone, and that creates a challenge, because the choices that one person makes will impact other people, whether those other people like it or not.  How many times have you seen someone post a picture to Facebook or Flickr that includes other people who may not have wanted the picture posted?

There is a certain amount of privacy that a social web automatically steals from us.  The questions are how much is necessary, and then how much is comfortable.  The tricky part is that depending on the application and the person, those answsers change.  And only being in the first generation of the social web, we are a long way from sorting out those pesky little details.

New Economy
My favorite topic of all, is the new economy (which I would define as the economic realities inherent to our modern lives as a result of, among others, the two factors above: mobility and social web).  But this is also the one that is routinely most difficult for people to get their heads around, because the ripple effect is pervasive, throughout every facet of our lives.

Old definitions no longer apply: “conservative” versus “liberal” are ill-fitting labels in a world of updated economic and social conditions that re-draw the political lines without even trying.  Words like “stability” and “security” are no longer applicable to the job market, after three decades of being considered the corporate Holy Grail.  And in a nation that was spurred to global dominance on the back of an Industrial Age economic engine, a nation of “knowledge workers” now routinely offshores work to less expensive parts of the world on a daily basis.

There are some pretty enormous downsides to the new economy — no more pensions, no more covered healthcare, no more job security.  But there are also some amazing opportunities in it — no more being stuck having to live someplace you don’t want simply because of its proximity to your job, no more expectation of having to let someone else define your rise up the corporate ladder on their terms and timelines, no more wistfully dreaming of being your own boss because it costs too much to start your own business.  Think of it like sky-diving: for some people it represents the most terrifying nightmare imaginable; for other people it is the single biggest thrill they could ask for.

As with most change, the pros can be just as compelling as the cons, depending on your point of view.  Socially speaking, the new economy means that goods and services that used to be out of reach for the average person are now vastly more affordable — everything from international travel to high tech toys.  For large enterprises, the ability to offshore entire divisions of your business means huge cost savings, and leaner in-house talent able to focus on the most high-value added functions.  For small business, the ability to dynamically pull together freelance, geographically distributed teams to execute on projects as needed, means being able to compete with larger firms without having to take on the overhead of formal staff.

So, yes, Barry’s list of small business trends is technically accurate.  But the reality is that the changes his list represents are even bigger.  And the reason they have such an enormous impact on small business is that these factors have already fundamentally shifted the social foundations on which small business is built.

(This post is part of my Entrepreneur Evangelist series and was originally published on WorkingPoint‘s Small Business Blog.)

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In a recent blog post, author Scott Ginsberg recently asked Have You Executed These Ten Essentials of Entrepreneurial Excellence? He then listed off the ten things he highlights as essential for entrepreneurs to be truly successful:

• Prestige requires pandemonium
• Confidence requires congruency
• Fame requires flexibility
• Success requires surrender.
• Creativity requires curiosity
• Originality requires murder
• Serendipity requires strategy
• Dominance requires discomfort
• Matchlessness requires relentlessness
• Remarkability requires reinvention

Scott’s list reminds me of a principle called Open Beats Closed, by an old friend and former colleague, Joshua-Michele Ross.

Much like Scott, Josh posits that in an information economy — particularly that fueld by the social web — the old constructs, objectives and means of accomplishment need to be re-examined and, in many cases, tossed for radically different approaches.  What comes out of these changes are a new set of social guidelines that are based on how our social interactions currently work, instead of how they used to work 5, 10 or 20 years ago.  And while these are most definitely “social” guidelines, they ultimately must also evolve into business guideliness.

Scott’s list is similar, insofar as that most of what he is talking about is the relationship between two seemingly unrelated concepts (in most cases) as being essential to success.  What is great about this list, though, is that it makes you think.  If you read Scott’s entire post (Josh’s, as well), the examples he highlights are all very relatable, and it doesn’t take long before your brain is scrambling for similar memories that make the same point.

To my mind, this begs the following questions:

• What assumptions are you taking for granted today?
• What historical conditions are you still artificially imposing on your life and your business, and can you spot them and let them go?
• And if you do, what does that mean?

One of the biggest ones I see entrepreneurs stuggle with is the “dollars for hours” problem — building a “practice” that is centered around their time, rather than building a business that can run without them.  What assumptions are at the root of this?  And do they still apply?  If no, what is the underlying reality now?

I find both Scott and Josh’s points tremendously valuable because everytime I review them, I am forced to acknowledge that some of the things I spend my time on are not valuable.  While that is frustrating in the moment, calling that out is the only way for me to make both my life and my business better.  And isn’t that why I started my own business in the first place?

(This post is part of my Entrepreneur Evangelist series and was originally published on WorkingPoint‘s Small Business Blog.)

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Scott Shane‘s recent article on Business Week is called, “Beware the Freelance Economy.”  In it, he posits that cheering for the increased number of new businesses is premature, since so many of them are really solo practitioners (a.k.a. “freelancers”).  His point is that, because of this, these firms are not realistic sources of new jobs and are unlikely to generate true wealth.

I think Scott’s analysis of these numbers is overly simplistic and missing a few critical considerations.

For starters, it is a mistake to compare solopreneurs with the traditional definition of a new business.  The more meaningful comparison is between solopreneurs and employees.  Entire segments of the solopreneur population are only capable of doing freelance work as a result of modern changes in technology.  Without these advances, many of these individuals would have no choice but to remain beholden to an outside employer for work.

I find fault with Scott’s assertion that says it is fundamentally better for the economy for that individual to work for someone else than to work for themselves, even if they are not directly employing anyone else.

While I will absolutely concede Scott’s point that there are drawbacks to an economy with a wide proliferation of freelancers (such as the implications to both our taxation structure, as well as our health care and insurance infrastructure), I think his concerns are rooted in Industrial Age models that lack a direct one-to-one application in an Information Age.

Migration patterns within the United States in recent years have increasingly seen the population moving from the Northeast and parts of the West to Texas and the South.  While the reasons can be debated or speculated upon endlessly, there are some basic facts that come with this migration: people are moving to warmer climates and lower-cost-of-living communities.

These migration patterns, coupled with the rise in freelancer enterprises, are why I consider this trend to be infinitely more positive than Scott is portraying it: once upon a time, it was necessary to live near a job.  As a result, communities clustered around large employers developed high costs of living.  It was the cost of doing business to be forced to contend with everything that went along with living in those environments: high rents/mortgages, long commutes, expensive food, pollution, etc.

Now that we are in an era where geography does not have to be the end all/be all of revenue, those of us who want to get out of that high-population density rat race have more options.

Case in point:

When we lived in NYC, my husband and I paid $500 per month in commuting expenses (combination of tolls, public transportation, parking fees and fuel; not counting the actual car payment and insurance).  We also spent a combined 3.5 hours per day sitting in traffic.  Particularly during the winter, we would be up and out the door while it was still dark, and we wouldn’t be home at night until it was dark again.

Now that we are in Texas, our commute costs are less than $75 per month.  Our ‘average commute’ is less than 15-minutes each way, and we almost never leave the house before the sun is up or come home after it has gone down (unless it’s for something fun).

So, my response to Scott’s concern about freelancers not being good for the economy is that, for some people, going freelance is an opportunity to go after a much healthier, happier lifestyle.  One in which there are still opportunities to support one’s family, without the trappings of being beholden to a single employer whose will could change one’s income status at any moment.

Even more than that, I would find it difficult to buy the argument that the over-all economy does not benefit from some of the perks to my freelancer schedule, which allow me far more community involvement, allow me to avoid contributing to gridlock and collaborating with other freelancers on projects that none of us would have previously been able to do if we were all working for someone else.  A lower income can be easily off-set by being able to live in a community with a lower cost of living, and has lifestyle benefits that go with it that can be extremely beneficial to both the freelancer personally and the economy generally.

Last but not least, is Scott’s contention that freelancers are unlikely to generate substantial wealth.  Again, the flaw I find in Scott’s argument is that he is comparing ‘the freelance economy’ to an Industrial Age definition of what a new “business” is supposed to be, instead of comparing them to traditional employment models.  And, once again, once you shift the comparison, then I still think freelancers win.

Why?  Because being an employee is almost never wealth generating (with rare exceptions of founding teams at startups or high-level executives).  Freelancers at least stand the chance of generating true wealth — or have the possibility of a healthier, more balanced lifestyle in the meantime that helps make the tradeoff worthwhile.

I do not disagree with Scott’s point that understanding ‘new business’ stats is not black and white: none of the information should simply be taken at face value.  The freelance model is somewhere in between traditional employment and traditional entrepreneurship.  As a result, none of the “traditional” metrics directly apply.

But we live in an age where the democratization of data and the mobility of the workforce allow new ways for people to work together without having to incur the costs of a full-scale firm to support their business.  The rules have changed, and so should our interpretation of the metrics.

In a long tail economy, I think there are far more important factors to consider than the ones that Scott has laid out.  So, as one of the people who fall into the category he finds concerning, I challenge his one-sided view of the numbers with this: I have done more work in the past year as a ‘freelancer’ that has helped create jobs, revenue and wealth for more people than I did in the previous five years of being an employee for other firms.

And I am very proud of that fact.

(This post is part of my Entrepreneur Evangelist series and was originally published on WorkingPoint‘s Small Business Blog.)

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I grew up in a family-owned business.  I remember, back in the early 1980′s, when my mother (the bookkeeper) got her first computer for the business: it was a Data General and it was bigger than our dishwasher.  It had five-and-a-quarter floppy disks; it had virtually no RAM to speak of; and it came with the classic DOS-based single color screen.  It was cutting edge in 1982.

I actually recount that memory quite frequently when I speak with entrepreneurs and technologists.  I love that story, because it illustrates how far technology advances have brought small business capabilities.  Thanks to solutions like WorkingPoint, Google Apps, Basecamp and WordPress, the world of small business is capable of competing in a global economy in ways that my parents could have never envisioned back in the early Reagan Administration.

This is the subject of Ross Dawson‘s post yesterday on My Venture Pad.  Ross highlights six specific ways in which technology is revolutionizing small business:

1. Findability
2. Customer communication
3. Productivity
4. Collaboration
5. Outsourcing
6. Online revenue

Ross’ points are all central elements, and ones that I discuss frequently when working with entrepreneurs, but there are three additional technology-enabled advancements that I routinely see making a huge difference to small businesses and their ability to be as competitive as possible.

Metrics
This one is one of my favorites: the democratization of data in the Information Age has amazing implications to small business.  Once upon a time, it was only the largest companies who had the ability to really dig into any metrics — whether they were numbers about their customers, their sales or their employees, information was expensive, and most small businesses had to do without.

The advertising industry is a great example: how do you calculate whether or not a television commercial or a print ad is worth the money it cost to produce?  That is complicated math that is based on a lot of assumptions (many of which are so baked-in that they are rarely questioned).  On the web, there is no question: if you serve someone an ad that compels them enough to click on it, you know.  Immediately.

Whether it is Google making data findable (as per Ross’ first point) or whether it is new startups like InfoChimps making a business out of building a marketplace for the buying and selling of data, the world now revolves around the flow of information, and that includes figuring out what to measure and how.  And then how to use that data.

Commoditization of Technology
When I first got online, it was 1993.  It was my college’s BBS system.  The vast majority of students could only access it when physically on campus, using a school computer lab.  And it was anything but user-friendly.  While the limitation in functionality was not insignificant, what was a bigger deal was the perception that you had to be super technical to figure out how to use it. People who didn’t view themselves that way couldn’t be coaxed near it.

Those days are gone.  Thanks to the proliferation of user-friendly, web-based technology, it is now possible for entrepreneurs to focus on the business of their business, rather than the technology of their business.  This opens the door to possibilities that, even as little as five years ago, were still too intimidating for the vast majority of non-tech entrepreneurs.

Mobility
Whether it is a satelite wireless card, a laptop or an iPhone, the expectation of mobility is now commonplace.  More and more, businesses that do not leverage the mobile capabilities and expectations of both employees and customers are not only missing opportunities, but are fast falling behind their competition.

In a world where your employees can Skype into a conference call from a coffee shop half a continent away, or where your customers are finding your office on their cell phone using Google Maps, mobility is central to how we both consume and disseminate information, both inside and outside of our businesses.

This is an exciting time for entrepreneuers for all of the reasons listed above — both Ross’ list, as well as my additions.  Never before has it been so easy for small businesses to access the types of goods and services that used to be exclusive to large corporations.  These types of changes make small business ownership possible for more people than ever before.  What could be more exciting than that?

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Well, I can’t say that I’m sorry to have seen 2009 go. Personally and professionally, it was one hell of a rough year. On the other hand, it did bring with it some changes that — despite fighting pretty voraciously at first — have ultimately proven to be profoundly valuable. The biggest and most obvious being the beginning of my formal entrepreneurial journey.

The year also saw several other things of note in my life:

• Making a new home in Texas. This is one that I can’t say I ever predicted. Of all the places I ever envisioned myself living, Texas was never once on the list. But the reality is that both my husband and I love it here, which only surprises the people who have never been to Austin.
• My husband has found a professional passion of his own (to be formally announced soon), after spending years merely tolerating work as an evil necessity. This has been magnificent for me to watch, and it’s been a truly great experience for both of us.
• I have started to redefine what type of lifestyle I truly want, and am now setting about how to create a business that supports that. Major lifestyle factors (such as remaining childfree) are baked-in parts of my life already, but other things — like being location independent and spending at least six months per year traveling — are part of my long-term goal, but until recently have not been part of my active, focused plan for our immediate future.
• I have spent the past several months working on redefining my relationship with time. This is a major source of conflict between me and my husband (and always has been), and so as he works to develop a higher sensitivity to and awareness of time, I am doing my part by trying to relax a bit and not be such a time Nazi. Small things like not nagging him when we are running late (and just accepting it), not wearing my watch every day, and eliminating daily use of an alarm clock are all things that I am attempting to help change how uptight I’ve become about time over the past decade.
• I got to attend my first SXSW and met my favorite blogger in person.
• Acknowledging that the satisfaction I used to get out of being a project manager is gone, and that it’s time for a new career. And while I do not doubt that project management will continue to be a part of whatever the my next career is, it no longer fuels and satisfies me the way it used to, so it can’t be the end-all/be-all anymore. More importantly, whatever my new career is going to be, it’s something I haven’t necessarily figured out yet. I’m working with a few different entrepreneurs here in Austin on some different opportunities, some of which have some very interesting potential. And I am optimistic that at least one of them could crack open and provide me the opportunity I am looking for.
• I have a newfound optimism about the economy, the socio-tech landscape and my place in it. I love writing The Entrepreneur Evangelist for WorkingPoint, because it gives me the opportunity to talk about the things I really care about while helping to promote a product that is part of a larger macro-economic shift that I not only believe in, but that I also find really exciting.
• I have recognized that my personal entrepreneurial journey has several more steps to go through. My husband has been strongly focused on trying to make sure we work on our business, while I’ve been busy working in our business. Much as I recognize that a dollars-for-hours trade is still essentially a J-O-B, I have also come to realize that I’m not entirely to a point yet where I can emotionally or psychologically move past that. I am looking for opportunities to do that over time, but for right now, that model is what I know that I know how to do successfully, and it’s my security blanket in an entirely otherwise insecure world. I’m working on it, and I’ve come a long way over this past year, but I’ve got more work to do to make the next few steps that are in front of me.
• Out of sheer financial necessity, I have learned to cook with beans (which is something I never, ever used to do), figure out how to live and eat on an insanely small weekly grocery budget, get creative about comparison shopping and making money stretch farther than I’ve ever previously even tried to manage… and finally come to the conclusion that as much as I hate all of that, I’d rather do that than go back to being someone’s employee.
• I have discovered that blogging for someone else makes it nearly impossible for me to keep up with my blog the way that I want to. So, I will start sharing my Entrepreneur Evangelist posts here as well. However, I do request that if you would like to comment on them that you do so on the original on the WorkingPoint site.

So, while it is most certainly not the year I had envisioned, it’s been a truly transformative one.

Finally, in tribute to the new year, I have changed the name of my blog. While I had enjoyed The Pragmatic Contextualist, to me that had very strong project management connotations. My brief experiment with The Pragmatic Entrepreneur never quite seemed to fit. And so now I have stripped out everything else, and just adopted “The Pragmatist.” We’ll see if that one sticks.

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I was reading an article this weekend, on Entrepreneur.com, and it actually made me a little snarky. In Health Insurance, a 401(k) and…Facebook?, author Justin Petruccelli discusses a new Junior Achievement/Deloitte Teen Ethics Survey in which 58% of teenage respondents stated that the ability to use social networks would be a factor in their decision-making process when it came to employers.

Since Justin and I are the same age (34), it’s probably easy to assume that my source of pissiness was the same as his: Get over yourself, you big babies.

In point of fact, though, my source of pissiness is him being pissy about these survey results. Because, while I may have nearly two decades on the participants of that survey, add me into the group for whom that would make a difference. And while my reasons may not look the same on the surface, I’d venture to say that they probably aren’t as far off as some of my old fart peers might assume.

During my entire career, I have only spend three and a half months working at a company that was neither a startup nor a tech company. You know why I only lasted 3.5 months? Because the 30 year old company had a 30 year old culture that hadn’t seen any modern influences since the Nixon era.

What became crystal clear to me in that environment — an environment, by the way, when even during the NYC public transportation strike, when some of us had absolutely no means of getting to the office at all (depending on where you lived) vehemently prohibited anything as ‘lax’ as working from home — is that the technologies and business practices a company adopts speak to who and what they are as a business.

Here is what it says to me about a culture, if a business blocks access to social networks:

• You don’t trust your employees. If you have employees who are abusing the problem, then grow a set, fire them and leave the rest to do their job in the way that makes most sense for them.
• You are not allowing your employees access to valuable tools for business. Whether it’s current events, industry news or general networking with peers in other companies, Twitter is the single most powerful tool I have in my daily arsenal. I get complex questions answered faster, find out industry-specific news more quickly, and generally manage to navigate my knowledge worker day far more effectively with Twitter than I ever did without. If an employer didn’t let me have access to it, I wouldn’t work for that employer.
• You are sticking your head in the sand and may as well paint a great big target on your ass. If you are restricting access to social media, then you are deliberately choosing to ignore changing trends in the marketplace around you. As an employee, any employer who deliberately did that would be someone I would think twice about working for, because I would read that as an indication of their attitude toward change and innovation in general.
• You are being capricious. Blogs are social media. Are you going to block access to those, too? If so, that would include most major news outlets (after all, NYT is on WordPress), and source of current events. And what about Delicious, Digg, StumbleUpon, Yelp, YouTube, Flickr, Trippit or LinkedIn? They are all social networks. You going to block them, too?
• You are misallocating resources. Does your IT team really have nothing better to do with their time than to lock down the firewall to prevent me from getting to Twitter? IT talent is expensive (I know: I’ve spent a well-paid career in that space), if you can’t think of something better for them to do than that, they you are not the type of company I want to work for.
• You are missing the point. Social networking (and text messaging) is how that age group communicates. Cutting them off from that would be like cutting me off from email and expecting me to be as fast, as accurate or as deft at navigating my day. Just because you and I have different preferred methods of communication does not make yours more valid than mine.
• You are setting a bad precedent. If you are summarily blocking social media, what other innovations can I expect that you will dismiss as having no value, despite the fact that your staff could find them profoundly impactful?
• You are fighting an unwinnable battle… which just makes you look lame. Business 101: Pick Your Battles.  The more time goes by, the more of your employees will have the same ability to ‘waste time’ via their smart phone as they do via a web browser. Are you going to confiscate their phones when they come to work, too?

So yes, if I was exploring working for someone, one of the things I’d want to understand was their social media policy. Absolutely. Just like having the ability to work from home when necessary, I consider that essential for my ability to be able to do my job well.

For those of us old enough to remember the internet before the web, I recognize that what is transformative about social networking is that it has made things that used to be hard much, much easier. I, for one, am not going to volunteer to hop in a time capsule and go back to making things harder again. Not if I can help it.

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