I have a confession to make: by the time we moved out of New York in 2008, I was burnt out on the Big Apple.  I was so excited to get away, that I couldn’t run fast enough for the George Washington Bridge.

In fact, I was so burnt out on NYC, that I was dreading coming back to town this week.  It’s been three years, and the idea of coming back to the city actually filled me with anxiety and not just a little bit of resentment.

As the week is wrapping up, though, I have to admit a couple of surprising things:

• I would absolutely be willing to live in NYC again… though, only on a part-time basis.  If I could come up with a way to live in the City from May through October, I would not hesitate.  For as much as this week has re-invigorated my love of the City, I am still past the point in my life where my love of the city over-shadows my loathing of snow.
• I would absolutely be willing to live in NYC again… though, only if I lived in Manhattan.  As much as I was ready to leave Manhattan when I moved to the Bronx in 2006, at this point, the only appeal to NYC is Manhattan.
• I would absolutely be willing to live in NYC again… though only if we can find an apartment with two bathrooms.  Honestly, this is something that most people in the suburbs take for granted, because most homes (hell, even a lot of apartments) have at least two bathrooms.  Having to go back to sharing one tiny little bathroom with no counter space again this week has been just about the only downside to being here.
• Working from home sucks about 80% less when “home” is in Manhattan than other places.  And, quite honestly, this came as a shock to me.  I didn’t really think it would matter that much.  But the overwhelming sense of isolation, the consistent energy drain from lack of interaction, the craving to be in an office, etc. is all mitigated considerably by looking out of the window and seeing Broadway, and by passing 300 people in the 4 minutes it takes me to run downstairs to buy a cup of coffee.
• I would definitely need to live in a mature neighborhood.  I am a homebody.  I am actually very surprised at how little I have strayed away from the UWS (Upper West Side) this week.  In fact, I have stuck so close to home that I didn’t even need to buy a MetroCard this trip… now that I think about it, I’m on day five and I haven’t even been south of 47th St., except for when we drove in from the Holland Tunnel.  I’ve really enjoyed this neighborhood, and the fact that I haven’t actually needed to go anywhere else.  An up-and-coming neighborhood couldn’t offer that.
• I am not sure I could do more than four floors of walk-up.  The part of me that knows I need to exercise more is proud of how much less huffing and puffing I am doing now vs. on Tuesday by the time I make it to the fourth floor, but logistics like carrying groceries and luggage, and stuff like that make walking up more than four flights of stairs seem a bit onerous.

Naturally, that first bullet point is the real challenge.  Apartments in Manhattan are hard enough to come by, but only wanting one on a funky schedule is probably worse.  (I need to find a time-share option with a student or a professor who wants to leave the city during the summers, or something like that.)

However, all in all, I am pleasantly surprised to discover that my childhood fascination with NYC is still intact.  After my last stint living in the city, I thought it had been mugged, stabbed and tossed into a rat-infested gutter, never to rise again.  I was so desperate to get the hell out of dodge by the time September 2008 rolled around that it never occurred to me that I’d ever again even entertain the thought of a potential return to the Big Apple… even if only as a flight of fancy.

Thanks for a great week, New York.  You reminded this California girl why I fell in love with you in the first place.  I needed that… even if I am (happily) returning home to Texas now.

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Twenty years ago, I was a sophomore at Ursuline High School. Just writing that phrase disturbs me, because I have no idea where the time has gone or how so many years have lapsed without me realizing it.

I spend so much of my time dealing with demographic information that it has become easy to forget that whether I’m discussing Gen Y mobile usage trends, or Baby Boomer social network adoption, or Gen X career management patterns, that I actually do fall into one of those categories. And we’re getting older.

In many ways Facebook actually makes this worse for me. I see a stark difference between my former classmates in elementary school and junior high than my classmates in high school. That’s not shocking: I attended public school (in the under-funded side of town) until 8th grade, and then I switched and started Ursuline as a freshman in 1989 (Class of 93). They were different worlds, and they produced different populations.

In a rough anecdotal comparison, just based on what I see in Facebook alone, I see that my high school classmates almost all ultimately moved away from Santa Rosa (in many cases we left for college and never returned), have far more lucrative careers, and generally took longer to get married and have kids than the people I went to school with during my K-8 years. As is often the case, those who came from money often married those who also came from money. Those who were destined to be successful by sheer force of will and intellect married the same. The inverse is also (usually) true.

But one of the other things that I see on Facebook is that many of my (female) classmates have only recently started having kids — many of them have none over the age of 5. I think this has made it easy for me to forget that we are all now 35, and that it has been 20 years since we roamed the halls of Ursuline High School in our blue and white uniforms during the George H. Bush Administration. As one of the few deliberately childfree one of my classmates, I don’t have growing kids to look at every day to remind me of my age. (Hell, my dog turned 9-years-old last week, and I still can’t believe it.)

Maybe that is part of why I find it so sad that, after 130 years, Ursuline High School announced that they would be closing their doors at the end of this school year. As the world’s least sentimental person and a staunch anti-traditionalist, I wouldn’t have thought that this news would be as disturbing to me as it is. But the more I think about it, the more I suspect that the real issue isn’t sadness about Ursuline closing than it is sadness about getting older.

The truth is, I hated high school. Especially by the time we got to the end of senior year, I was dying to get out of there. The last day I had to wear my uniform, I went home from school that day, changed my clothes and proceeded to light a bon fire in the fireplace and watched in satisfied glee as the white Oxford shirts and herringbone skirts were engulfed in flames.

However, to be fair, there was very little I hated about high school that was Ursuline-specific. Mostly, I just hated high school. There was very little about the ages of 14-18 (24, actually) that I didn’t find painful, and which I wasn’t eager to forget. Part of it may have been my Mom’s death the year before high school started, but whatever the reason, like a Pat Conroy character, I swore I’d never trust anyone who ever thought of high school as a pleasant experience (which just made it highly ironic that I married someone who loved high school).

As a result, I have very few memories of that time in my life, anymore. I see names on Facebook that I know I should know, pictures that seem vaguely familiar if I squint hard enough, who’s biographical information clearly says we were classmates, but I can’t place them. (And since I threw away all of my year books, I can’t even look them up.) With a class of less than 100, I imagine that my poor memory has more to do with choice than overload.

And yet, hearing that tuition at Ursuline has climbed to more than $11k/year shocks me enough to make it obvious why the school can no longer attract enough students to be able to afford to stay open. Yet that saddens me, too.

My husband and I watched Bottle Shock this weekend. For those of us who are old enough to remember growing up in the California wine country when it was still a farming community, it is a great movie to watch. But, like the closing of Ursuline, the movie also reminds me that time has marched on and that my slightly hazy romantic memories are wildly out-dated.

Sonoma, Napa and Mendocino Counties are now the home of big money wine industry agribusiness with the overly-trendy, high-priced tourism and expensive cost of living to match. And while my father’s neighborhood has become more and more gentrified over the years, it’s still the under-funded side of town where you are at least four times more likely to hear people speak Spanish than English.

It’s been almost six years since (the last time) I moved away from Sonoma County. There is something cruelly romantic about the stagnant snap shot created by time and distance. It’s easy to think of things the way they were when you left, and find yourself surprised to discover changes during brief holiday visits. Friends you keep in touch with may work their way out of the frozen image — they get married, divorced, have kids, change careers. And if you are in touch, your mental picture of them can change.

Places are harder, though. You don’t keep in touch with a place. It doesn’t send you Facebook status updates or Christmas cards with this year’s picture on the cover. A place stays the way it was in your mind, no matter how much the individuals you knew there may have changed. So that makes this week’s new about Ursuline a bit of shock (and not even just for those of us who are gone). Of course places change. We know that the individuals all have; we know that our families have; we know that we have. The place felt permanent, though. It felt like it wouldn’t, shouldn’t and hadn’t ever changed (sometimes to our dismay). And now it has.

So thank you to the Ursuline Sisters. You set out to create generations of young women who would take their place in the world with confidence and grace. And for whatever our differences may have ever been (and there were plenty), I still believe that yours was a worthwhile goal, which I’m sorry to see dim.

And as an aging, Generation X alum who takes a lot of comfort in the marketing b.s. about ’50 being the new 30,’ I thank you for one final, educational lesson: fight it though we might, no matter how far away we move or how successful we become, eventually we all do become the older generation who can’t help but ask, “Where has the time gone?”

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Hunting Dog

The past several weeks have been very eventful around here (hence the lack of updating). They have led to a couple of really powerful revelations that I’ve been working through, as I have been trying to get my feet under me in the new job.

I’ve spent so much of the past year writing about life as an entrepreneur that I was a little surprised to finally come to the realization that, no matter how hard I try, I am actually not one. At least not at this point in my life, anyway. And, ironically, there was no real way for me to know this until I tried to do it and then went back to working for someone else.

My first week at my new job, I flew to San Francisco (Yay!) to spend most of the first week in the office. It took about two hours of me being there to be deliriously happy. And not for the steady paycheck, or the socialization of working around other people again, or even being home for a visit. What made me happy was getting to focus on doing what I do, instead of the business of what I do.

I realized that I am the classic E-Myth example: I am the woman who loved baking pies, so she opened a pie baking business… only to grow miserable at having to run a business instead of baking pies. And the moment I started working for someone else, all of a sudden, I found myself able to focus on what I do again.

I have made such a career out of multi-tasking that it never occured to me that, under certain conditions, I simply couldn’t do it. Multi-tasking at a task-level is one thing; multi-tasking at a higher level — e.g. working in my business and working on my business — has proven to me to be something else entirely. Even crazier was, that I didn’t realize it until I stopped. Over the past two years, I’d grown so accustomed to feeling the pressure of owning and running my own business that it wasn’t until I shed myself of it that I realized it was suffocating me. And as soon as the business of the business became someone else’s problem and I got to go back to being a specialist, suddenly not only could I focus again, but I could also BREATHE.

I spent four days in San Francisco taking ridiculously deep breaths, feeling my lungs fill with the cool Pacific air, feeling the oxygen rush through my bloodstream and generally feeling a sense of relief that only comes from being confined in cramped quarters for too long, and suddenly feeling the rush of fresh air as you step into sunlight. It was like taking off the tight dress clothes after an over-the-top Thanksgiving dinner: all of a sudden, your lungs instantly feel capable of working again.

This realization was fascinating to me for another reason, as well. I’d lost touch with something in myself over the past two years — thanks to the ego pounding of not being able to find a job, the emotional roller coaster of not knowing what I wanted to do for a living anymore, the isolation of working from home, and the increasingly frequent homesickness I’d been unable to shake. I lost the confidence I’ve always had in my ability to tackle damn near anything.

There was a great line in the movie “Julie & Julia” where Julia Child is writing to her friend while living in France and attending cooking school at Le Cordon Bleu. She says that, despite being surrounded entirely by male classmates and a headmistress who can’t stand her, she discovered something key about herself that she’d never known before: she was fearless.

That was always me. Until I ran my own business. And, while I’m sure that if the circumstances around starting the business had been more empowering and less desperate, things could have been different. In the end, for me running my own business managed to obliterate my sense of fearlessness. Even worse, I didn’t know it until my second day back to work for someone else.

My husband — who is an entrepreneur to his core — asked me how my trip was going. I felt guilty. From the time we’d met, he’d always discussed us having our own business. And while the idea never held any appeal to me, I didn’t ever really say anything, because that was his dream and I didn’t want to quash it. But sitting in the office in San Francisco I knew the time had come.

I told him that I felt awkward about telling him, but the truth was, I knew this is where I was supposed to be. I knew this was what I was supposed to be doing. And I felt myself finding my sea legs almost immediately… and that once I had them back, it was now clear that what had been holding me back wasn’t just the market or my directional challenges or the nature of my work making it hard to work alone. What had been holding me back was the fact that I was really one of Cinderella’s step-sisters, and that no matter how hard I tried, her shoe simply didn’t fit.

The image that popped into my head later was that of a hunting dog. (Leave it to a dog person to resort to canine metaphors, I realize.) I don’t want to own the estate. I just want to hunt. But as a business owner, it was my responsibility to tend the land, manage the horses, pay the taxes and hire the staff — all that before anyone gets to load the rifle. You know what? That’s not me. I’m a hunting dog. And I’m better at it than most.

But if I have to spend my time and energy on things that I’m not good at and that I don’t like and which I do not feel are worth the effort that they require for the benefit I get out of it, then all of a sudden, I’m trying to turn the hunting dog into an accountant — which is absolutely absurd and counter-productive. I make a hell of a hunting dog — if I can focus on the hunt.

And I realized that’s what I have now. I have an extremely entrepreneurial company — which is the kind that I like — with tons of opportunity, blue oceans all around us, and a need for a multi-faceted, slightly ADD, very hungry hunting dog. My new CEO recognized that immediately. And the reason I wanted the job immediately is because I saw it, too.

So, do I regret the past two years? Yes and no. I regret what I’ve put my husband through. He’s put up with a lot as I’ve been on a roller coaster that I didn’t understand how to get off of, and I put him through the ringer on more than one occassion by doing everything 180 degrees opposite from what he needed me to do just for him to be able to sleep at night. I am sorry for the ulcers, the fights, the aggravation and the anxiety I caused because, for an articulate person, I couldn’t find the words to express what was wrong, what I needed or how I was feeling.

On the other hand, I spent since early 2008 — long before we left New York — miserable, not knowing what I wanted to be doing, not enjoying anything about work, and questioning everything I thought I was supposed to be doing with my life. That confusion followed me to Texas and cursed our business from the moment we started it. And so the sudden shock of clarity feels amazing — much better than it could have ever felt if I’d never been lost in the first place.

So, whether I identify as a hunting dog or Cinderella’s step-sister… it doesn’t matter. The fact is, I’m back to being me again. And the part of me that I like, who loves her job, who feels capable of contributing again, and who can be comfortable saying, “I am not an entrepreneur — but I sure as hell love working with them!”

And being married to one.

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We are now almost officially at our two year anniversary in Austin.  I can say, without a doubt, that it’s been an amazing rollercoaster — not one that I ever would have knowingly signed up for, but one for which I am immensely grateful, in spite of its rockiest moments.

In the past two years, we moved to a new town, started a consulting business, began building a web startup, and adopted a cat (which, for anyone who knows me, knows that is the most bizarre thing on this list).  In addition, I’ve been through more not-quite-fits as potential jobs, decided I didn’t want to work for someone else, then decided I did at least five different times.

I’ve learned what made me love my favorite past jobs, what made me hate some of my previous roles, and what kept me in some places longer than I should have stayed.  I’ve identified the things that motivate me, the things that demotivate me, what I used to want that I no longer want, and what I used to be good at that I now can’t stand doing.  I am now clear on where I want to go, what I want to learn, where I want to focus, and what I want to learn to do better.

I couldn’t say any of these things a year ago. (Or hell, even six months ago.)

I’ve figured out more in the past two years than I set out to do.  It sucked more than I wanted it to.  It was cooler than I thought it could be.  And it’s brought me to the end of one very difficult chapter… which has, quite happily, brought me to the beginning of a new, exciting one.

I am delighted to announce that, as of September 13th, I will be returning to my roots without actually back-sliding: I will be rejoining the never-dull world of ecommerce in my beloved Emerald City by joining the awesome team at SysIQ as an Engagement Manager.

In addition to being a multi-platform integrater of several of the market’s leading ecommerce engines (which is cool, but not necessarily novel), they are also practitioners of well-honed online marketing principals and my methodology of choice, Persuasion Architecture.  In fact, one of their key value propositions is that they can leverage the power of Persuasion Architecture, regardless of ecommerce platform, through a combination of process and technology.

As someone who’s spent the past year studying, working and learning more and more in this space, the opportunity to marry what I know well (ecommerce) with what I want to know better (Persuasion Architecture) by working with a team I like (SysIQ) in a place that I love (San Francisco) was too much to actually hope for.  Happily, it happened, anyway.

(And to pre-emptively answer the first question I keep getting asked: No, we are not currently planning to move to San Francisco. BrainMatch is still here, so Austin will remain home for the time being.  My life will be spent traveling and telecommuting, both of which are A-Ok with an ADD, antsy-pants like me.)

I am spending the next two weeks wrapping up most of my larger client engagements, and shifting the nature of my Indigo Heron products to being largely virtual in nature.  This will take time, of course, but for as much as I am excited about the opportunities that await me at SysIQ, I also feel very strongly that both my husband (who is my business partner), my clients and my business deserve the respect of my continued support, even once I am back to a full-time job.

So, that’s the news.  I am extremely excited by this change, because it represents a lot of work over the past two years (three years, in many ways). It is a move with an enormous amount of potential, and it balances my varying and seemingly conflicting needs in a way that I didn’t dare hope was possible.

And as I look forward to a new array of fun and exciting professional challenges ahead, I find myself profoundly grateful.

• I am grateful to Kevin, Jonas, Lisa and Austin for the past year at Tech Ranch.
• I am grateful to TW, Chris and Pam for some great lessons out of Praxsys.
• I am grateful to my friends and family back home for being so gracious about my tendancy to fall out of touch for long periods of time at a strech.
• I am grateful to Sherry, Ryan, Tim and Kate for helping make me laugh and keep me (mostly) sane through the ups and downs.
• I am grateful to Abdul and Kirra for their amazing ability to be strong contributors to the upswing.
• I am grateful to all my clients over the past two years for their faith and their business.
• I am grateful to John for being generous beyond words, filled with endless support, always taking the opportunity to make connections and being an amazingly good sport when I’m at the end of my rope.
• I am grateful to Donna, Dani, Sara, Kari and Maija who reminded me this weekend during my first visit home in a year and a half that when I’m doing work that I love, I am more likely to develop meaningful, long-lasting friendships with amazingly talented and brilliant people.

And I am especially grateful to my husband, Charles Andretta, II, who is the most patient, generous person I know, and who has rolled with my mind-changing, direction-flipping, emotionally conflicted, career crisis self with a degree of understanding that no one could ever reasonably ask of another human being.  And I am eager for a new chapter where, for the first time since we’ve met, we both feel good about each of our professional direction.

Now, I think it’s time for a glass of wine.  I feel like celebrating.

xoxo

~Alora

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Like many of my peers in Generation X, my parents and my grandparents have never really understood what I do for a living. My parents use the web, so it’s not entirely outside their comprehension, but when it comes to my grandparents: I may as well be communicating with aliens via mental telepathy. Being an knowledge worker in a digital economy is a bit of a leap for people who don’t watch TV or listen to the radio and who rely almost elusively on a paper copy of a newspaper for their information consumption.

I think that’s part of why I am often fascinated by generational research: I see how big the difference is in my life versus my parents and grandparents, and I am riveted at the idea of what subsequent generations are going to experience that I am not even capable of imagining. I was thinking about this as I was reading a great list on YoungEntreprener today: 27 Inspiring Young Online Entrepreneurs.

When I look at the companies these entrepreneurs started — Mashable, Volusion, Digg, Box.net, 99Designs, iContact — I can’t help but think that this may be one of those interesting examples that I’ve been looking for when it comes to ways in which Generation Y will be different than Generation X. I think we tend to dismiss many of these success stories as anomalous. And while they certainly are in terms of their success, I am not so sure they are when it comes to what motivated them to embark on their “pet projects” in the first place.

And in the end, I think this really may be Generation X’s most exciting legacy to Generation Y: an internet-driven economy that has made it much more possible for a teenager to have the tools on-hand to build a business that is worth seven-figures even before the first day of freshman year of college. Sure, not all teenagers are going to take advantage of that opportunity; and not all who try to take advantage of it will be successful. But the fact that option is so much more readily available than at any previous point in history is just… well, really, really cool.

My husband’s new startup is about pairing businesses with high school students to crowdsource project work. And while most people love the idea and are eager to get involved, the one consistent source of pushback we do hear is, “What kind of business value do high school students really have?” It’s been a fascinating lesson to me, to see how deeply entrenched that perception is among so many people. Most people don’t have a concern about trusting college students, but the idea of high school students is just jarring enough that some people can’t quite get their head around it.

Personally, I think that lists like this are encouraging. For too long, too many of us with creative talents and inspiration believed what we were told when someone said to ‘wait’ — until after college, until later in a career, until some nebulous date off on the horizon — to pursue our dreams. I love that these young entrepreneurs just considered it normal to start young. It didn’t occur to them that they shouldn’t. It’s further evidence of what (creativity and education specialist) Sir Ken Robinson says: we ‘educate’ kids out of their creativity over time, and teach them not to stand out, not to differentiate themselves from their peers, and to stick to the safest, most boring and most conventional path.

I think it’s sensational that these 27 young entrepreneurs bucked that trend. And I think it’s fantastic that they are high profile enough to help set an example for those who come after. And I think it’s cool that in just my lifetime alone, we’ve gone from 8-track tapes to the iPad, and that there are eager young entrepreneurs who automatically dive in to find their niche. It makes me fabulously curious about what more is to come.

While plenty of people — usually older — scoff at the idea of a 24-year-old CEO of a multi-billion dollar enterprise, I say good for them. Life is short. The only value in “waiting” is if you don’t know what you want to do. If you know, go for it. After all, if you’re going to trip and fall, I always figure it’s best to do that when you’re young enough that you don’t have to worry as much about the dangers of breaking a hip.

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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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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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Many people don’t think about it specifically, but know it intuitively: if you want good customer service, skip the big guys and go to a small company. In Small Business’ Competitive Advantage, I discuss that Customer Service is the magical pixie dust for small business.

Think about your normal daily experience: if you need to deal with your bank, your insurance company or your utility provider, you call an 800 number, where you are greeted with an automated message, a phone tree that routes you through a series of menus, as much automated information as they can possibly prepare, and then — if you’re problem is too complicated to automate — eventually you may get a person.

And then what happens?

You have to repeat your account number, despite having entered it already (at least once); you have to answer questions to validate your identity (or, worse yet, you don’t, which always begs the question: who else can get into my account?); and then you can get around to your question.

In many cases, by the time you get to speak to a real person you are dealing with a call center on the other side of the planet, non-native speakers (who sometimes struggle mightily with English), and in worst case scenarios, people who are clearly reading from a script with very little real understanding of either the nature of your problem or how best to handle it.

And when it’s all said and done, how often do you go through all of that, and get off the phone feeling totally confident that your issue was resolved? Rarely. More often than not, most of us get off the phone feeling like we just got the run around so badly that we need to double and triple check our next round of statements to make sure no one messed anything up.

All in all, because of the economic needs for businesses to automate and off-shore customer service functions, the general state of Customer Service is often crap.

This is where small business owners can be Superman. Seriously. For most small businesses, we don’t have the volume to go through all of that expense and hassle. Our customers often have our direct phone number. They know where to find us, how to reach us and what our specialty is. And while that may not always be great for our daily productivity (and it can certainly be abused at times), it gives small business owners the chance to leave our customers with a far, far better customer service experience than the one they just had with their credit card company.

We talk so much about business that we often over-look the most important fact of all: business is conducted between two or more PEOPLE. Sure, there are functions that can be automated and there are often good reasons to do it. But when you leave your customer feeling like less than an actual person, you’ve just provided a lousy customer service experience. Small businesses, because of logistics, have a built-in advantage. And it’s one we should all remember to take advantage of.

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I’ve been feeling nostalgic this week. After so many years in ecommerce, supporting catalogers and retailers whose year entirely revolved around the Christmas season, I am almost at a loss for what to do if I’m not running around putting out fires from Thanksgiving weekend up until the week before Christmas.

Strange as it seems to most people, I loved the chaos of the holiday season back in my MarketLive years (2000-2005). I really did. It was high drama, high anxiety and high chaos. All the delicious things that a good single workaholic who lives four blocks from the office craves.

And what was even better was that we knew it was coming, so we got to anticipate it for months before it happened. It was like standing on a beach, watching a huge wave build and build as it rolls towards you and just standing there, bracing yourself, waiting to see if you’re going to be able to keep your footing.

Since so many of my core strengths come to the surface when it’s time to put out fires, it was a natural time for me to hit my stride. In hindsight, I can clearly see that some of the reasons I enjoyed it so much played into some of my less healthy habits. It was still a hell of a lot of fun, though.

Hub in the Wheel
Particularly during my years running point for IT Hosting and Operations, I always got to be in the middle of everything. If I’d had what is euphemistically referred to as “a healthy work-life balance” (a term that makes me crazy), then I wouldn’t have considered that a perk. But, since I didn’t have a life outside of work and since I had a huge ego, being in the middle of everything all the time worked very nicely for me.

Troubleshooting

When things go wrong on an ecommerce site during it’s busiest weeks of the year, any minute of outage is a potential disaster. So every second counts. What I loved about the holiday season is that we ran at a fever pitch, so when anything went wrong, the best troubleshooters in the company were all collected together to figure out what was wrong and how to get it fixed.

At the age of 27, that was one of the greatest experiences I could have asked for. Not only did I learn how to troubleshoot better than almost any professional I have ever worked with since, but I did it with other brilliant, creative, talented people who were also good at it. Part of me wishes I hadn’t taken that skill for granted so much back then. It would be years later before I understood how remarkable a team we had, and how amazingly gifted they were at it.

Making Things Happen

There is nothing I find more gratifying than progress. Like many project managers, I love making lists — simply so that I can cross things off of them. It’s something I find profoundly satisfying. One of the greatest things about the holiday season in my ecommerce days was that suddenly process took a back seat, obstacles were knocked down, priorities were re-oriented and all that mattered was getting something DONE.

Friends

To this day, I have never worked in an environment where I had as many close friends. It was the foxhole mentality. It’s common in the military and political campaign teams. And startups.

Those of us who used to deal with the fires spent insane amounts of time together: we ate together, we argued, we got punchy with each other, we got punch-drunk until we cracked up laughing at 3:00 a.m., we worked 24+ hours straight together, we called each other in the middle of the night to get help with issues. We made each other crazy, we made each other laugh, we made each other smarter. It was awesome, and I’ve missed that rare combination of talent and circumstance ever since.

Like many people, the older I get, the more nostalgic I get about times gone by. I’m lucky that for much of the craziest part of those times, I actually really loved it in the moment — not just after the fact.

It never fails now, though: I see the polished world that ecommerce has become — all marketing and very little tech — and I see the predictions about what kind of sales Cyber Monday is going to see, and I think back to my late 20′s when that was my life.

It makes me proud to think about all the crazy things we managed to pull of with no safety net. It makes me sad that I don’t go to work with those same phenomenal people every day. And it makes me happy, now that I’m a little older and a tiny bit wiser, that I don’t have to be on-call, anymore.

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