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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For any entrepreneur, the value of a mentor can almost never be overstated.  Whether it’s building your business plan, defining your market, figuring out a product strategy, or trying to sell your spouse on the idea that giving up a steady paycheck from someone else is a sane thing to do, a mentor is one of the single most valuable things any entrepreneur can find.  Sometimes they come out of the woodwork when you least expect it; other times, you have to go on an aggressive hunt for the right one.

One of the best places for many new entrepreneurs to start is SCORE. (Disclaimer: WorkingPoint is a SCORE sponsor.) SCORE is an organization comprised of small business owners — some actively running businesses, others retired — who work together to build a community to support other small business owners.  While some parts of the country have locally grown networks to support entrepreneurs, SCORE has more than 350 chapters across the US, dedicated to providing counseling and advising services to small business owners.

This week, on SCORE’s Ask an Expert blog, advisor Steve Bloom posted an article on a recent experience he had working with an entrepreneur whose idea was not something he felt had sufficient market to be a viable business.  In the post, Steve recounts the conflict he felt between wanting to encourage the entrepreneurial spirit and the strong sense that this particular idea had extremely long odds of success.

Ultimately, the real point he endevours to drive home, is that whether or not the idea is successful, the entrepreneur can still learn a tremendous amount from trying to get his venture up and running.  The value of the lessons one can learn through failure is something that every entrepreneur must always remember.  In the blogosphere “failing fast” is a common topic, but in reality, most of us are so terrified to fail that we will often turn ourselves inside out in an effort to avoid that experience.

This is one of the places that a mentor can help: a mentor who has been through the process before can not only offer their insight and perspective to help navigate pitfalls, but they can also help remind you that, even in the event of failure, you still get value out of an experience.

One of the most important exercises one of my earliest mentors walked me through was a process of defining my ‘worst case scenario.’  And, amazingly enough, I quickly realized that once I defined my biggest nightmare, it wasn’t anywhere near as scary as it was when it was a nebulous, ill-defined gray cloud hanging over my head; even better, it became much easier to insulate myself from the worst of the possible ramifications once I was clear about the details.

The flip side of Steve’s lesson is equally important: a mentor does not know everything.  And while it’s always nice to have a mentor who understands both you and your idea, the fact is that everyone has different strengths.  Just because a mentor may not consider your venture to be the world’s greatest idea, doesn’t mean it isn’t worth doing.

Part of the test for a mentor is to give you the best advice and encouragement they can; part of the test for an entrepreneur is to listen, process the information, and then make a final determination based on what you know to be true.  You won’t always agree, but that doesn’t make the advice bad, or the mentor wrong.  And hearing those concerns raised is always important, because it helps a new entrepreneur re-examine assumptions and ideas, to make sure there are no holes that have been over-looked.

So, if you have or are looking to start a business, and you do not already have a mentor, I’d strongly recommend looking for one.  There are plenty of different approaches to try (serial entrepreneur Penelope Trunk isn’t above being slightly annoying to snag the one she wants), but whatever you do, start looking for one — check out a local SCORE chapter, Chamber of Commerce, startup incubator or entrepreneurial Meetup.

Wherever you look, just remember: someone who has done it before, always has insights of value for someone just starting out.  They may not all fit, but there is always the chance for some great gems that can help you side-step a landmine.

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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Tim Berry has a recent post on MyVenturePad that is highly worth reading.  He takes issue with a VentureBeat post that essentially recommends to entrepreneurs that they sacrifice their life until they get their business successfully built.

Tim hits the nail on the head right out of the gate: the absurdity of that recommendation is the idea that once a business is successful, it is somehow going to miraculously be easier for an entrepreneur to walk away from it to start building a life.  He gives a list of very useful things to do to avoid falling into this trap.

For me, though, the real problem with this advice is the assumption that it is only business that it hard — having a life is easy.  Anyone who says that has never tried to shift gears and go from being a workaholic to being a romantic partner.  As someone who has spent five years working on that transition, I’ll tell you: it’s much harder than it sounds.

If you spend your twenties — and worse yet, also your thirties — focusing on building your business while neglecting your life, why would anyone assume that suddenly starting to focus on having a life at 40 is going to be a cake walk?  There are days when I am convinced the reason we live so long is because that’s how long it takes to practice to even start getting our lives right.  If we don’t even begin until it’s half over, then we’re out of time before we begin.

One of my favorite bloggers, Penelope Trunk, writes about this regularly: as a serial entrepreneur, she moved her family from New York City to Madison, WI for their life.  She founded a tech startup in a city with virtual no tech industry because that was where it made sense for her family to live.  Has it been a struggle?  Sure.  Was there reasoning in her logic?  Absolutely.

Everyone wants to know that their legacy has an impact — for some people having kids is enough.  For others, leaving behind impressive business accomplishments is enough.  But if what you want is both, then you can’t delude yourself into thinking that you can ignore one for half your life and suddenly make up for it in the second half.  Time doesn’t work that way.

So many entrepreneurs I know start their own business because they want a lifestyle that allows them what working for someone else never has: opportunity and flexibility.  And most of the reasons they want those things are because they have, or want to have, a life.

I’m with Tim: waiting until your business is successful to start building a life is asking to have a lop-sided legacy.  And that may be fine for you, but make sure you know that going in.  In business these days we spend so much time discussing how hard it is to build the necessary relationships to be successful.  Does anyone really think it’s easier to build successful relationships in the rest of your life?

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

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As a content strategist one of the things I spend a great deal of time discussing with entrepreneurs is SEO.  As I’ve written here before, my first goal in any SEO discussion with someone is to help educate them on what SEO is and isn’t, and what it really can do versus what it really can’t.  (Can: help people who know what they are looking for find you; Can’t: wash your dog, change your oil or solve all of your sales and marketing problems.)  And then from there, we can discuss what a reasonable SEO strategy would look like for a small business.

In the end, though, I always end up advocating one thing: valuable content.   And while I often get a lot of ‘yes ma’am’ head nodding around that topic, there is a single critical reason that I continue to make that point: the world of search is on a roller coaster at the moment, and trying to play the SEO game with the current set of rules is only going to get you a short-term win (if that) without putting your focus on strong, valuable content. This is a great untapped opportunity for entrepreneurs, because they are better equipped to move faster than large businesses, full of teams of people whose job would be in danger if they were not longer perceived as critical.

People who are unfamiliar with the online search space often do not understand what I mean when I talk about the imminent changes to the the industry.  Today I’ll cover a few examples, thanks to some new releases that Google has just made. (Examples from Google’s official blog.)

• Personalized search
• Real time search

What is “personalized search“?

For example, since I always search for [recipes] and often click on results from epicurious.com, Google might rank epicurious.com higher on the results page the next time I look for recipes. Other times, when I’m looking for news about Cornell University’s sports teams, I search for [big red]. Because I frequently click on www.cornellbigred.com, Google might show me this result first, instead of the Big Red soda company or others.

What is “real time search“?

Now, immediately after conducting a search, you can see live updates from people on popular sites like Twitter and FriendFeed, as well as headlines from news and blog posts published just seconds before. When they are relevant, we’ll rank these latest results to show the freshest information right on the search results page.

These are two great examples, because they demonstrate why having relevant content on your website is important.  Focusing your SEO energy (and budget) on building link-backs and fine-tuning your keywords has limited value in the long-term, because search engines are going to increasingly focus on other things to establish relevancy.

Just these two changes alone mean that two different people can type in the same keywords but get different results, depending on their personal search history and when they look.  And, if you factor in the increasingly popular localized search, what city those users are in could also impact their results.

What excites me most about these changes is that it further helps in taking the focus off the means and onto the end: your web presence should be about engaging your customers in a meaningful way, finding new customers and enhancing your existing relationship.  Far too many people focus on jockeying for a good SEO position in spite of their content, instead of focusing on the content first and using it as a foundation for successful SEO.

The tidal wave of changes in the search space is going to make it increasingly hard to duck the real question for all businesses on the web: are you saying anything worth paying attention to?  If you are, then these updated techniques will only help you.  If you are not and have been playing SEO-peek-a-boo, then these changes are going to expose that.

I see far too many entrepreneurs who have been taken to the cleaners by unscrupulous “SEO consultants,” and one of my chief missions is to help prevent that wherever possible. So before you look to hire SEO help, ask yourself if you are prepared to actually create (or pay for) good content for your website.

In the modern web-based business world, there is an updated version to your grandmother’s old saying:  “If you don’t have anything relevant to say, don’t say anything at all.”  These new changes by Google will continue to make that point.

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

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One of my favorite things about the information economy is the extent to which a highly commoditized, social web lowers the barrier to entry for prospective entrepreneurs.  While some of us elect to dive into owning our own business head-first with little or no safety net, that’s not the best way for some people.  Many people need to ease their way into entrepreneurship, and one of the ways I most enjoy watching is through their hobbies.

Daniel Kehrer of Business.com recently wrote about the new trends of hobbyists-turned-entrepreneurs, and their increasingly noteworthy impact on the small business space.  In reading the six reasons he lists as catalysts for this phenomenon, it makes me think of three different friends of mine who have spent years dancing on the edges of entrepreneurship with hobbies they enjoy.

The Painter
For years The Painter has paid the bills by being a project manager leading development teams in web application environments (which, naturally, is how we met).  She is smart, creative, a great integrator of complex project solutions and very well-respected by her peers.  But her love is painting.  So, as a side business, she not only sells her paintings, but she also does commission artwork: she paints customized pet portraits.

The Engineer
Ironically, “the engineer” is a double-entendre for my second friend: while we used to work together when he was a system engineer for the ecommerce site I worked on, his hobby is an online model train community that includes an ecommerce business.  What started out strictly as an enjoyable past-time has, over time, become an increasingly viable business in its own right.

The Event Planner
Did you ever have a friend who was the go-to person for something for everyone they knew?  My friend is the go-to person if you want an event planned.  Whether it’s one of her best friend’s weddings, my 30th birthday, or the company Christmas party, if there is an event to be planned, she is the person you want to draft.  Not only does she know how to get it all done, but she can even make sure it comes in on budget.

While all of her friends have spent years telling her that we’d love to see her own her own business to do this professionally, it wasn’t until she got laid off and started volunteering for local non-profits that her decade-old hobby started to morph itself into an actual business.

What I love about each of these three examples is that none of them went out looking to start a business, first and foremost.  What they started with was something they simply loved to do.  Over time, the business aspect evolved.

The six reasons that Dan lists are things that, in essence, amount to much of what “the long tail” is all about, and it’s at the heart of the opportunity that the information economy provides.  So while not everyone is going to see the type of run-away success that passionate entrepreneurs like Gary Vaynerchuck experience, what this trend does is remind us that the age-old saying has a modern day variation: “Where there is a passion, there is a way.”

As entrepreneurs in a new era, that’s an exciting opportunity.

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

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CNN recently reported that researchers from Harvard Business School, Insead and Brigham Young University have just completed a six-year study of more than 3,000 executives and 500 innovative entrepreneurs, and say they have identified five skills that drive innovation:

Associating: The ability to connect seemingly unrelated questions, problems or ideas from different fields.

Questioning: Innovators constantly ask questions that challenge the common wisdom. They ask “why?”, “why not?” and “what if?”

Observing: Discovery-driven executives scrutinize common phenomena, particularly the behavior of potential customers.

Experimenting: Innovative entrepreneurs actively try out new ideas by creating prototypes and launching pilots.

Networking: innovators go out of their way to meet people with different ideas and perspectives.

I find the results of this study interesting, if not earth-shatteringly shocking.  What’s even more interesting, however, is that CNN’s article also comes with some recommendations about how to develop those skills, even for those of us who don’t consider ourselves tremendous ‘innovators’ to begin with.

Recommendations:

• Teach yourself to think differently by deliberately taking opportunities to act differently
• Identify a problem and writing nothing but questions about it for 10 minutes a day for 30 days
• Identify a business, customer, supplier, or client, and spend a day or two watching how they work so you can better understand their issues
• Build a diverse network, and understand people’s backgrounds, interests and strengths; and then make sure to remain in touch with them regularly

Since most of us are creatures of habit (to one extent or another), taking opportunities to break behavioral patterns and act differently can be hard.  But it is the corollary to the old saying, “The definition of insanity is doing the same thing over and over again and expecting different results.”

So, sane or not, if you want different results, then make sure you do something different.

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

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