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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I had a plan. I was going to spend my 30′s moving up the professional food chain, to snuggly position myself in a COO or CIO position at a small to mid-sized technology firm by the time I was in my early- to mid-40′s. I was going to that until I was around 50, and then I was going to make a career change and shift into professional coaching and consulting.

That plan included several assumptions:

1. I would have another source of income at the time I switched to coaching that could compensate for me going from a cozy 6-figure salary to a low 5-digit salary over night. (My husband’s business, probably.)
2. I was going to continue to love managing operations.
3. I was going to want to continue to be the boss.
4. I was going to continue to want to work in technology.

I always considered the biggest risk to that plan to be point #1. Never in a million years did it occur to me that the real problem was going to be items #2-4.

I absolutely love my current job. I adore my bosses. I enjoy my co-workers. And I am pleasantly surprised every single week by incredible, positive attitudes and the amazing results that they can produce — all from within my current company. It’s someplace where I have no problem trying to recruit friends to join, because I have no doubt about my bosses’ sense of integrity, priorities or values, and I do not worry that I’ll feel bad about pulling my friends into an awkward situation — and I have had more than one job where I could not have said that.

But last night, during a great conversation with my boss, he surprised me with a piece of interesting news. I started laughing and said, “This is why I’m here: you will never give me the chance to get bored! Every time I think I have figured out what to expect, you come up with something new.”

It was a totally spontaneous, sincere moment and I absolutely meant it (and still do, more than 26 hours later), but as those words came out of my mouth, I had an epiphany: part of the reason that I love this so much is because, in my heart of hearts, I know this is the last job I will have in this space. And like the 11:45 rush to ride Space Mountain one last time after a full day at Disneyland, I am in the interesting and unique position of knowing that I want to relish the experience, because it’s going to be my last one.

I have only ever made a living at a keyboard. Like anyone who has been in this space since before the 2000 Bubble Burst, I have now been on this rollercoaster ride more than once. The climb is exhilarating, and the fall is both devastating and empowering. But this time was different for me, and as I watch the business climate around me change, I see very clearly why I am not the same 28-year-old who eagerly looked forward to the bounce-back last time.

That time I knew there was more I wanted to do, to learn and to see in the space. I was still in love with it. I was still addicted to the adrenaline. And I was still the young junkie looking for the next great professional rush.

I’m not that person anymore.

The things that I used to care about and enjoy — technology, process, systems, models and concepts — do not interest me in and of themselves anymore. When the web was the Wild West, it was exciting and new and untamed. Now it’s overly polished, overly researched, overly commoditized, and overly sterilized.

It’s like in “Pump Up the Volume,” when Christian Slater’s character said: “All the great themes have been used up and turned into theme parks.”

For three years, I’ve been fighting it. I thought that if I moved to a new city, or found a new job, or worked for a new company, that I could revitalize my flagging interest. And I couldn’t figure out why none of it worked. But now I get it. It’s the people who interest me. And that’s why I can love my current job, and give it my all, even though I never want to look at another Gannt Chart or sit on another conference call ever again: because I just adore my bosses.

It’s interesting how much easier it is to seriously consider the future possibilities once I let go of the past. I have been truly blessed to be able to sincerely say that I have loved my career. I have been able to make a wonderful living doing something that I loved, and meeting people who (with the exception of my husband) only ever came into my life because of work. But I don’t love it anymore. For me, for now, the people are enough to help keep me motivated, but I recognize that time will eventually change as well.

I have some ideas about what is coming next for me — whenever that is. It’ll be a while, because my current boss knows how to play up to my ADD inclinations and will keep me fascinated and entertained for quite a while. And as long as that is true, and as long as I end each day able to say to myself, “I adore who I work for,” then I’m not going anywhere.

But whether it’s a year from now or five years from now, the day will come when even adoring my bosses and constantly finding myself surprised at work won’t be enough. And when that happens, the next job won’t be a re-hashed version of this one. It won’t have anything to do with project management. It won’t have anything to do with technology. I won’t spend my day at a keyboard. And I won’t have to carry my phone with me at all times to respond to emails within a minute of their arrival.

I’m still not exactly sure what it is going to be, but it’s going to be physical and lifestyle-based. It’ll probably have something to do with food (or maybe dogs… or both!). It’s going to be one-on-one and individual. It’s going to be personal and inspiring. It’s going to be about change and transformation. I think about it a lot, now that I’ve stopped trying to fight it. And like the perfect, dream vacation that you roll around in the back of your mind while sitting in traffic, this is something that I mull over slowly and languidly, debating options and weighing permutations.

Eventually I’ll figure it out, and start actively planning for that transition. But for now it’s still just past the horizon. But instead of filling me with dread, it now fills me with peace of mind. Because it means that I can be truly present in my current job, without constantly looking towards what must inevitably come “next.” So I can enjoy it for what it is: smart people, complex technology, and the dance between the world of business and the world of bits and bytes.

I can let myself be pleasantly surprised by a boss who is always planning something new, and I don’t feel the need to second-guess or anticipate his next set of plans. I can sleep at night knowing that my efforts are contributing to the success of a business founded by men I both like and respect. And I can laugh over trivial crap, and amusing ironies, with incredibly smart people who are genuine, inspiring and endlessly enjoyable.

Eventually I’ll figure out what my next career is going to be. And, at some point, I’ll figure out when it needs to be. But for now, I’m focusing on savoring the last job I’m going to have doing the only thing I’ve ever done.

I had a plan. It’s gone now. I’m going to need another one. But I’m going to take a very Zen-like approach, and just have faith that when the time is right, I’ll figure it out. And in the meantime, I’m going to enjoy the rush of that one last, good rollercoaster ride.

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I’m an anti-traditionalist. I firmly believe that most “traditions” were born out of need, and over time we’ve romanticized the past and sentimentalized things that started off as purely pragmatic. Join me for a story that illustrates my point:

A newly wed couple prepares for their first Christmas together. While preparing other items for the meal, the wife makes a request of her new husband. “Honey, would you please cut the shank off the ham?”

The husband responds, “Cut the shank off the ham? Why?”

The wife stops, slightly thrown by the question. “Because… we need to remove the shank.”

Equally perplexed the husband arches his eyebrows. “Why? I’ve eaten ham at the holidays my whole life, and never cut off the shank.”

Returning to her chopping, the wife shrugs, “I don’t know. That’s how I learned to do it from my mother.”

“If there is a reason we should, that’s fine with me. But I’m curious about why.”

“There’s the phone,” the wife nodded her head towards the wall. “My parents are home. Why don’t you call her and ask?”

Picking up the phone, the husband dialed his mother-in-law. After recounting the conversation, the wife’s mother paused. “Hhmm. You know, now that I think about it, I am not really sure. That’s how I learned to cook a ham from my mother. You should give her a call and ask her directly.”

On a mission, the new husband phones his wife’s grandmother. He quickly recounts the unsolved mystery he is trying to uncover. Much to his surprise, Grandma begins to laugh. “What’s so funny?”

Grandma clears her throat, and with a lingering giggle says, “Sweetheart, I only cut the shank off the ham because we were too poor to afford a pan big enough to fit the whole thing!”

I was a pre-teen when I first heard that story, but it made an enormous impression. This has been at the heart of what I look to understand when I get involved in organizational change efforts: Do we do things this way for a valid reason, or one that no longer applies?

Of course, the trouble I never considered as a child was that, for some people, the mere fact that there was once a reason is often good enough of a reason to keep doing something. I suppose I can sort of understand that when it comes to what you eat at Christmas dinner or where you like to spend your Fourth of July holiday, but in business that reason is the Kiss of Death.

At DrupalCamp in Austin recently, the head of a local development firm mentioned that, once per quarter, his company shuts down for the day, and spends the whole day working on internal processes. Each member of the business is charged with keeping a running list all quarter long on existing processes that need improvement or new processes which need to be developed. And then the company turns off the phones for a day, and collectively re-works the processes that need to be fixed.

It’s a fascinating approach to the old saying “working on the business vs. working in the business.” And it’s a very tactical example of how to build an organization that is always asking, “Why?” And then making sure that the answer is something better than, “Because that’s the way we’ve always done it.”

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Someone recently commented to me that the MBTI was the “astrology of the consultant set.” The comment amused me, but I realized that (as a member of said “consultant set”) I was taking for granted the value I found in it, in large part because I spend my days surrounded by other people who also consider it valuable.

In parallel, I had a conversation with a co-worker about the requirements documentation for a client project we are currently working on. I keep bothering him to ask how something is supposed to work because, even though it is documented in the requirements, I have a huge amount of difficulty getting what I need out of them. To me, this is what the requirements documentation looks like:

The Matrix Code

Occasionally, if I work at it long/hard enough, and once I get familiar enough with the context, I can sometimes get to the point that it looks like this:

The Matrix Agents

But in more than a decade in this business, I have never once seen this:

The Woman in the Red Dress (The Matrix)

This is why I find value in the MBTI: after 14 years in this industry, surrounded by people for whom this type of information makes perfect sense, I struggled with the fact that I can’t be as productive as I need to be — and/or as my colleagues are — because, in this format, this information doesn’t make enough sense to me to be actionable.

Understanding the difference between N’s and S’s in terms of a basic orientation to the world has been enormously valuable. There is a demonstration conducted by Dr. Nick Grant (who is a therapist and consultant who specializes in applying the MBTI in practical settings, teaches at UT and uses the Myers-Briggs to help build high-performing teams for businesses) at the Wizard Academy that Roy likes to use as an illustration of how the two groups differ in their perceptions.

Dr. Grant divided the room by S and N types, and then showed them an object and asked them to describe it. The group of S-types came up with an organized list of it’s physical characteristics: size, shape, color, etc. The N-types described it in terms of it’s applicability, similarities and difference to other items, etc. (And they were not as organized about how they collected and presented the information, either.)

The S-types described the thing itself, in physical, tangible, material terms. The N-types described it as part of a larger context, and part of broader patterns and uses. Both groups were right. The question isn’t of right or wrong. The question is around orientation. Both sides could see and recognize the accuracy of what the other group was saying. The point is that each of them had their own starting point for how they perceived the object, and what information they considered relevant in describing it.

Of course, for people who don’t buy into the Jungian notion that there are four basic personality types (which is a concept that pre-dates Jung, just with different terminology), then of course the idea of the Myers-Briggs probably smacks of astrology. In which case, there’s not really anything I’m going to be able to say to change your mind. (Even assuming I were inclined to try.)

However, for those of us who find applicability in the data — both personally and professionally — there are some very valuable lessons to be take from it:

• The same information must be presented in multiple ways in order to be properly understood by your entire audience. This creates an enormous amount of work up-front, but it makes buy-in and implementation of a new initiative go far more smoothly. (This is especially true for consultants or anyone managing a change initiative.)
• Process by itself is not the solution. (Hardcore S-types might have a stroke at this notion, but just bare with me.) Process is about the deconstruction of an end-result to be able to consistently reproduce predictable results. The trouble is that people are not machines, so giving them steps to follow does not necessarily provide them with the necessary context to provide good results. This is especially true for knowledge workers: if your business depends on the creativity, adaptability and specialized expertise of individuals, then how different people process information is of vital importance to your success.
• Once you understand your default orientation, it is possible to identify ways to improve on your weaknesses and enhance your strengths. Like most things, though, understanding just how strong or how weak you are in any given area will determine how much work you need to apply, and just how much you can really expect to improve. (This idea is at the heart of strengths-based psychology.) For some functions and at certain times in your life, it might make sense to focus on getting better at something you normally struggle with (e.g. if you are starting a business, and have to wear all the hats yourself); at other points in your life, it makes more sense to focus on what you do best, and leave the things that weigh you down to someone else (e.g. once you are making enough money in your business to outsource the functions that distract from your core expertise).

At the end of the day, business is about individuals doing something — often in collaboration with others — to deliver results. We can build systems and tools and processes until we’re blue in the face, but they only work if they meet the needs of the people. All it takes is for a key person to have a bad day to change the entire course of a business — he could get mad and fire someone who goes off and gets a job with his competitor, he could snap at a reporter and bring down a torrent of bad press on his business, he could throw back a couple of drinks at lunch and wrap his car around a tree on the way back to the office. As much as we like to pretend that business is not about individuals, it really is.

The key is that a successful business is about a collection of individuals working together — and there is nothing about that process that isn’t made better by understanding how different people’s strengths, weaknesses, and perceptions come together. Quite often, the difference between a winning team and a losing team is just one critical member (and not even necessarily the official “leader”). A weak team makes bigger messes than it can clean up. A strong team is greater than the sum of its parts. And sometimes the only difference is the role the team members are trying to play. Assuming that any person should be able to fit any role is the fast track to mediocrity.

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At the Wizard Academy a couple of weeks ago, my hubby was talking to Roy Williams about accomplishment. Roy made a very interesting observation that applies to both my husband (an INTJ) and to me(an ENTJ). He said that it’s not at all uncommon for (Myers-Briggs) NTs to spend just enough time living in their own world that once they think something, in their mind it’s now done and so there is no need to actually do it in real life.

This is particularly interesting to me, because this has been my curse since I was a child. And it’s something that haunts me to this day: if this blog had HALF the articles on it that I’ve written for it in my head, it’d compete with HuffPo for volume. The trouble is, once I work through what I’m going to write in my head… I’m done with it, and never get around to actually sitting at the keyboard and writing it out.

As the absolute Queen of Unfinished Projects, I’m fascinated about how to mitigate this. From the time I was a child, I love ideas: the idea of a project, the idea of a trip, the idea of an event, the idea of whatever — and yet, the second I fall in love with an idea, I end up combatting one of two problems:

1. Either the reality never comes close to the version in my head, and always ends up being a supreme let down, or
2. I don’t have the patience and tenacity to stick with it to make it happen.

Because I’ve already accomplished in my head, the tedium of accomplishing it in real life quickly becomes more trouble than it’s worth. After all, why spend all that time and effort actually doing something, if I get the same sense of satisfaction just by thinking through it and mapping it out in my head?

As I continue to work through the next phase of my career, this insight is incredibly valuable to understand why project management has been getting harder and harder for me over the past few years. I simply don’t find the details needed to get a project all the way to the finish line worth the effort.

I have a self-fueling demotivational problem, because project management — which is really an SJ-type of profession, not an NT one, anyway — requires supreme attention to details. This is not my strength under any circumstances. But, when you factor in Roy’s observation, it makes even more sense.

For example, I have a new blog that I’m interested in setting up (or, maybe it’s just a new section on this one — I haven’t entirely decided yet), chronicalling my efforts to get healthy. The focus being, not only my new experimentation with meditation and yoga (and, hopefully, soon to include Muay Thai and/or Brazilian Jujitsu), but also how my husband and I can eat healthy on a $60 per week grocery budget. The unique slant on the blog is to be a look at the investment need for this effort: does it cost time, money or health quality?

The problem, however, is that last Friday evening, I mentally did it. I walked through the set-up of a new WordPress install. I picked a theme. I set up all of the plugins that go with a new site. I identified the categories. I designed the icons I wanted to use to represent my cost triangle. I did all of it. In my head. In my head, it is a great success that helps me stay focused, and which helps me find other people who have ideas that are very usable in my effort.

Of course, this poses a problem, because — in the reality that exists OUTSIDE of my head — I haven’t done anything on it. And yet, because I feel like it’s been done, now the actual act of doing it just becomes too tedious to bother with. It takes the fun out of it. And since this isn’t intended to be a chore, there is no point in doing it if it isn’t fun (and helpful).

So… I haven’t done it. And I don’t know if I actually will at this point.

What to do about this? Well, the first thing, I guess, is to stop mentally mapping these things out all the way. Don’t allow myself to do it until I sit down to a keyboard and start writing. This is the obvious solution, but I can’t imagine anything more difficult. Despite spending most waking hours per day in front of a keyboard, the fact is that I usually do this type of mapping while I’m AWAY from a keyboard — while I’m in the shower, driving, running errands, etc.  It is often my version of a “break” from work: it’s the intellectual equivalent of going for a walk or (ironically) going to a yoga class.  So this is an exercise that I often find very refreshing and gratifying.  Which, I guess, means that I need to reserve these types of mental gymnastics for projects that I do not actually have any real intention of doing.

Of course, this is far easier said than done. However, it is sort of reassuring to know that this is a fairly common problem for NTs in general, and not unique to me (and my hubby).

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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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For some people entrepreneurship is a philosophy. For others, it’s the price we pay for an idea we are passionate about. But what’s the difference? And, even more importantly, why does it matter?

I think it matters most if you are in a B2B business yourself. As a business that serves the needs of other businesses, understanding the motivations of your customer can go a long way toward understanding how to sell to them, when not to, and where their comfort levels are.

It also matters socially. Birds of a feather will often flock together, and that is often true of entrepreneurs. Entrepreneurs tend to have slightly different lifestyles than people who are content to be employees, and as such, they tend to find it easiest to relate to other people with a similiar outlook on life.

Entrepreneurship as a Means

What do I mean when I say ‘entrepreneurship as a means’? I mean that entrepreneurship is the means by which someone can accomplish something worthwhile. Owning your own business may not be your main goal, merely the vehicle to help make your real goal possible.
For entrepreneurs who fall into this group, there are often a myriad of motivators:

• Lifestyle
• Wealth-building
• Passion around an idea

Any of these things can lead someone to set aside the relative ‘stability’ of a J-O-B, strike out on their own, and start building their own business. For these people, while entrepreneurship may be an adventure with its own series of challenges and rewards, it also may not be in their bones, and if circumstances changed, these are often the people who could be content to go back to working for someone else again.

Entrepreneurship as an End

The other side of the coin are the real evangelists. These are the die-hards who will move from venture to venture, opportunity to opportunity, and for whom working for someone else is the psychological equivelant of being buried alive.

This is a completely different mindset, and one that I would guess is in the minority among entrepreneurs, though they are often more high profile. This group tends to have a tenacity that keeps them moving on to a new idea after the last one crashed and burned. This is the group that writes blogs, starts conferences, builds incubators, hosts Meetups, and sponsors competitions.

One of the most important reasons to stop and consider this question is really for yourself, however. Is your entrepreneurial journey a means or an end? The reason I find this question particularly compelling for business owners is that it helps set priorities.

If entrepreneurship is an ends in and of itself, then bouncing from one idea to the next, building multiple businesses at once and having a social circle that is largely composed of other entrepreneurs is probably a common sight.

However, if entrepreneurship is merely the means, then your other goal should be clear. Why? Because entrepreneurship takes sacrifices that being an employee doesn’t. While the payoff potential is greater, the investment is far steeper — sometimes at great cost to the rest of your life. Any new entrepreneur needs to understand than before diving into the pool.

Understanding what motivates you is how you know what things to outsource vs. what things to manage internally; it’s how you figure out what are the priorities for your time and how to focus your business objectives; and it’s how you identify your own personal tipping points where the sacrifices are not worth the price.

Entrepreneurs who never stop and consider these points can end up like hampsters on a wheel, with no progress and no recognition of their lack of progress. Knowing why we do what we do, what we hope to get out of it, what we’re willing to pay to get it, and how long we are willing to keep it up is how we build a plan — for our business and for our life.

And, in the end, whether we meet the goals or not, at least sorting out the motivation helps us keep marching on the days when it’s hardest to get out of bed.

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