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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Job hunting is rough for oh-so-many reasons. One of the things that is hardest about it, though, is managing your own attitude and spirits. If there is one thing that is liable to get you into trouble during a job hunt, it is unmanaged anxiety.

I’ve written before about some of the things that I discovered were helpful during a job hunt, but in talking to other people, some more questions have come up that I want to offer suggestions about.

Time is Like Money: You Can Only Spend it Once
This is one of those things that is really obvious, but that most of us need the occassional reminder about. Time is precious, and you have to consider when you are spending it wisely, versus when you are just blowing through it on the temperal equivelant of Twinkies.

A really, really great thing to do while you’re hunting for a job is finding local organizations to get involved with. It might be a non-profit, it might be a Meetup group, it might be an internship at a local company. Whatever it is, consider that volunteering your time gives you the following:

• you are (theoretically) doing something that can go on your resume to help fill in an employment gap
• you are networking with people you wouldn’t normally have access to
• you showcasing your skills to a new assortment of people who might have entirely different ideas that might be helpful for you
• you are working on things that can give you a sense of accomplishment and pride, which come across in your attitude when speaking to prospective recruiters/employers

The first thing that people say when you talk about volunteering their time during a job hunt is to counter with the ultra-important point: but I need to make money. Of course you do. No one is disputing that. But the point is that you cannot spend every possible second of the day job hunting. Aside from your mental health requiring a break, look at volunteering your time as time spent networking. If necessary, do it instead of something else (like watching TV).

You Are What You Eat
This one is hard, because when you are looking for a job, it’s often more comfortable to socialize with people who are either in the same boat or with people we know and with whom we feel safe. But there is no more important time to work on expanding your social networking than when you are job hunting. And, even more importantly, it’ll help keep you sharp.

Just like the food we consume helps determine our physical help, the information — including the attitudes, personalities, data and social cues — we consume will determine our mental health. People look like their friends and associates more often than not. If your friends and regular social circle are not providing you with the support and motivation you need, then start expanding your horizons to include some new influences.

Is your mother a downer who depresses you for days every time you talk? Then pick up a couple of cards at the dollar store so that you can write her quick “Thinking of You” cards for a while instead of calling her and letting her bring you down.

Is your best friend miserable in their life and only ever want to complain over drinks about how lousy a day they’ve had? Then shake things up a bit. Use being unemployed as an excuse to avoid going out for drinks (too expensive!), and drag them out to do something else instead. A game of bowling often costs the same as a single drink and lasts longer. It’s also a physical activity that will get you both moving a bit, provide some good people watching, and give you other things to talk about.

There is no need to “dump” the people you care about. Just don’t let them bring you down. And if some of the most important people in your life are not being helpful when it comes to keeping your spirits up, then it’s also fair game to tell them that you need their support and help in staying positive. Most people don’t realize when they start becoming a downer to be around. Often times, just pointing out that you are counting on them to keep your spirits up is enough to help them become more aware of their own habits.

I had some other valuable tips I learned that you may want to check out, too. But the keys I’ve found are not slipping into old habits, because no matter how comfortable they may be, they are often the embodiment of that old saying: “Insanity is doing the same thing over and over again and expecting different results.” If you need a new outcome, don’t rely on doing the same old same old to get there.

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Ask anyone who got into an internet-based business prior to 2000, and you’ll hear nostalgic “good old days” stories, the way my grandparents talk about ‘when Kennedy was President.’ It’s hysterical to hear, and it saddens me endlessly to think about how long ago that was, but it really was an exciting time — and not just for the massages and catered lunches (which we had, too).

What was exciting was doing something new. Being a small group of people, pushing a boulder up a hill together was an amazing experience on so many levels.

Personally

On a purely personal level, it provided both opportunity and comradery that I absolutely soaked up like a sponge. There is no bond between co-workers like the bonds built while firefighting in the middle of the night for days on end. People are tired, punch drunk, but our brains were flying like trapeze artists trying to find solutions. And the best part? Every single time we eventually figured it out.

That built huge faith and trust in and among the team, because you quickly learned who was good at what, and who you needed to pull into a room when something was blowing up. I learned that technical trouble-shooting was an art form, and the fine-tuned dance we could do as a team when it came to examining the performance of complex systems would make the Bolshoi envious. To this day I find a kind of agonizing beauty in pulling together a talented team of people to trouble shoot a truly baffling problem; and to this day, I’ve never worked with full teams of people who were as gifted at it as the people I worked with in my early career.

And some of the most important people in my life to this day, were the people from that time and place in my life. I wouldn’t trade it — or them — for anything.

Intellectually

When you are trying to build something new that not everyone understands or cares about (or understands why they should care about), you have to learn to be very quick on your feet. You have to be able to discern what is truly important to them, and then draw them a map of why what you are offering will lead them to where they want to go. Sometimes it’s an obvious leap; other times it’s total bullshit. But either way, it’s an intellectual challenge that is invaluable to master, because you have to do it quickly, while you’re ‘on stage’ and you have to be sincere enough to be convincing.

It sounds like I’m saying that I learned to be a salesperson, doesn’t it? In truth, I did. To be sure, I don’t enjoy “sales” in general and I’d never want to make my career at it, but all business is selling. And if you want to be good at business, you have to learn this — the earlier the better. Whether you are selling yourself and your skills to a potential employer, or you are selling your product to a potential customer, anyone who can’t figure out what someone wants and how to give it to them won’t make it very far in business.

The sooner you learn this, the better off you’ll be.

Commercially

When I first got online way back in 1993, the internet was still a playground. It had not yet become ‘the new frontier’ of business. But I loved it, and since the web was beginning to emerge as a viable business environment, I knew I wanted to find a way to do that professionally. I just didn’t know how or what exactly that would mean.

Being in ecommerce from 2000-2005 was a great time. And targeting the small- to mid-sized cataloger and retailer (which was our demographic) was what kept us alive when the bubble burst. It also proved to be highly valuable for other reasons.

While other ecommerce software providers were busy trying to sell into the top end of the market — the Fortune 1000, who had millions of dollars to spend on a site — we were aiming at a higher volume of smaller clients. Of course, this was one of the reasons that we couldn’t continue to be a services company — we had to have a product in order for our business to scale this way. But it also meant that we had a much bigger pool of potential customers. All we had to do was to streamline our own processes to be able to take advantage of some economies of scale.

What is still one of my favorite parts of this whole experience, though, is when I remember back to conversations that we used to have with C-level executives (usually either CEOs or CIOs) about setting up an ecommerce site. Many of them were still unconvinced that it was actually necessary. The old school, brick-and mortar retailers and catalogers were often not ready or able to see that their world was about to be completely transformed, and that the internet was going to be the heart of the future of their business.

Often times there was an internal evangelist (and in family-run businesses, it was quite often the founder/owners’ twentysomething kid who was working in the family business and trying to push things forward) who convinced the CEO to at least listen to the pitch. But even after they heard it, they were still frequently not convinced that the internet wasn’t just a fad that would go away in a couple of years, and that any investment made in the meantime would ultimately be a waste.

Looking back on it, these conversations always make me smile, because they are classic examples of adoption resistance that all new technology breeds. At the time they were highly frustrating and (from my standpoint) ridiculously short-sighted. But now I think about them and chuckle.

To be sure, each one of the reluctant CEOs did eventually have to cave to their internal evangelist and outside market expectations of their customers who truly wanted them to make their products available online — whether they chose our product or not. And, in the end, they did all come to recognize that, over time, ecommerce was essential to the health of their business. But in some case it took a while.

That experience was illuminating for me, though, and it is probably the single biggest reason that I have very little patience for the whining currently going on in the automotive and newspaper industries. To paraphrase Ricardo Semler: if you bury your head in the sand, not only do you miss vital opportunities, but you also leave your ass in the air as one hell of a big target. Those who’ve spent the most time and effort burying their heads in the sand end up screaming the loudest when they get shot in the behind. And truthfully, I have no sympathy.

Any thoughts on other value to being on ‘the bleeding edge’ of a new space?

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People who did not meet me until at or around my 25th birthday would never believe it, but in school, I was the Queen of Slackers. Truly. School was too easy, too routine and I spent too long doing it to be able to breath new life into the experience. I could dodge classes, do my homework at the last minute (assuming I did it at all), skip out on reading assignments and skate through tests in my sleep. As a result, I got very, very lazy. I couldn’t see the point of exerting effort on something, if by doing almost nothing I had nearly as good a result.

And then I got a job — that ultimately turned into a career — at a start-up. Pay dirt!

The transformation that sparked in me is still an endless source of amusement among my friends. It took me a while to realize why, but eventually it was clear: the problem with school is that there was an upper limit on what I was capable of achieving. It was an artificial cap on how well I could be scored. I found that inherently disincentivizing. In business, however, there is no upper limit. You can take something as far or as high as you can push it (given the right environment, of course).

And, even better, in a scrappy, entrepreneurial, risk-taking startup (especially one trying to survive an economic downturn) someone who is hungry, talented, teachable and willing to dive into the deep end of the pool head first has tremendous opportunity for growth. The first three years of my career were the most educational, exciting and energizing time of my life — all of my years of school combined couldn’t compare to those three years. Everything was new, everything was interesting and I never once had the slightest bit of doubt that I could conquer anything that came my way.

Ah, the hubris of youth!

Of course, there were downsides. Like many young people, I didn’t know my limits and was constantly pushing the envelope in ways that I probably shouldn’t have (and in ways that I’ve since learned not to do). Whereas many 26-year-olds may be more inclined to do that with parties, I did it with work. I ended up missing a lot of important events in the lives of friends and family because of that.

I was also still extremely idealistic about a great many things. Instead of The Pragmatic Contextualist, an appropriate blog title would have been something along the lines of The Snarky Idealist or Bring it On and Get Out of the Way! (Which, ironically, is still how some people tend to view me, though I have toned down considerably with age.)

But that idealism was invaluable to me, because it made me fearless: if anything is possible and I’m extremely capable, then what do I have to be afraid of? I don’t tend to be very risk-adverse in general, but I have become more cautious with age (though, not quite enough for either my husband or father’s tastes). Back then, though, it would never occur to me that I wouldn’t figure out a way to succeed at whatever I did — which meant I was a hopeless volunteer junkie.

My biggest rush came from fixing problems, and in a post-bubble burst start-up, there were plenty of things to be fixed. So I had an endless supply of opportunity, and endless confidence in my own success. Happily, I also had bosses who went from having nothing to lose by letting me try, to truly believing in my ability to make a positive difference.

As was inevitable, a few kicks in the teeth later, and I stopped being quite so cocky. The pragmatist in me was ultimately born of those experiences, and the eternal idealist retreated to the back, only to come out for the occasional political event.

One of the biggest, most valuable lessons I learned was how to deal with chaos. More recently in my career, I had a bizarre moment when a senior IT Director — who was easily 25 years older than me — groused that we were working in “the most chaotic environment” he’d ever experienced in his life.

I wanted to laugh and call him a weenie (I restrained myself — though barely). The environment we were working in at the time was easily the least chaotic environment I’d ever experienced, and his inability to roll with the punches made him a particularly weak and frustrating leader in my opinion, because he got frazzled very easily, whined constantly and was tremendously rigid. It never occurred to me until that moment that my ability to handle chaos was all that unique.

Naturally, one of the dangers of getting a bit too used to high volumes of chaos is that you can become a drama junkie. This did happen to me, and it took me a while (and outside circumstances) to curb it. But what I have seen of most drama junkies (and trust me, I wasn’t the only one I knew) is that, the older we get, the less tolerance we have for that same constant fever-pitch of insanity.

This is another reason that I have often recommended aimless twentysomethings seeking career advice to explore startups: because by the time people are settled in their career, married or have kids, startups can be a bit too rough on the lifestyle. So if you’re going to do them, best give them a shot while you’re young, energetic, single and have as few external obligations as possible.

But when I look back on that time now, I am profoundly grateful. I was drinking from a fire hose, and it never occurred to me there was any other way to work. I got to sample a spectrum of potential opportunities and figure out which ones held some appeal, and which ones didn’t. If I had found myself in a more stable, structured environment back then, I can’t imagine where I’d be now, because the lessons I learned there, and the all-you-can-eat-buffet of opportunities that I had available to me at the time are how I found my way into a career.

In the scheme of things, I look back on the most pivotal, impactful decisions of my life and the day I left the famed O’Reilly Publishing — which is where I thought I’d wanted to work for years — and went to MarketLive (at the time it was still called MultimediaLive) was one of them. And since then, I have found myself encouraging twentysomethings who do not know what they want out of a career to look at startups, because as long as they can develop a bit of tolerance for chaos (which I firmly believe everyone should do), they’ll usually find opportunities they never knew existed.

What do you think? Are startups a good or bad place to start out your career?

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I had a couple of discussions this week that got me thinking back to the early days of my career. Aside from leaving me feeling older than I care to think about, it did spark a pleasant memory or two that I’ve been mulling over since.

Specifically, I’ve been thinking about how early career choices can really set the stage for the directions we take in life. As is often the case, many of the largest influences on our lives are not obvious until many years later. And while I am as likely as anyone to take them for granted, every once in a while something will happen to make me stop and consider the series of events that brought me to where I am now, and what the unintended consquences of seemingly small actions or events have ultimately provided.

There were three defining elements of my early career that I have been noodling on, because they had much larger impacts on me than I ever would have predicted at the time:

• Getting your start in a startup. What is the value to launching a career in a startup environment?
• Being in the ‘wild west’ of a new market space. What does it mean to be in a new space?
• Transforming a company from being “a services company” to “a product company.” What are the differences and why are they important?

Undoubtedly, the first two of those are a bit sexier than the third. However, all three ultimately shaped me in ways I never fully realized at the time. The lessons learned were a bit rough sometimes, but when I compare some of my experience to that of my peers, I realize that I had the opportunity to be involved in some things that have served me extremely well and that I wouldn’t trade in for anything.

Over the next couple of days, I’ll cover each of these topics in a separate post (each one is too long to combine them).

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It’s been years since the evangelism for Agile development started truly gaining momentum. Super sexy buzzphrases phrases like “reduce time to market,” “improved ROI,” and “lower development costs” have all been invoked to support the case for adopting an Agile methodology over the old-school Waterfall approach.

The fact is, most experienced professionals have lived through enough project pain that they don’t typically need a huge amount of convincing that Waterfall is often inefficient — particularly for longer, larger, more complicated projects. In a fast-moving world, the risk of constantly changing requriements is ubiquitous, and a Waterfall project does very little to insure against that danger while still delivering a valuable product to users.

However, the problem with the “Agile Development” argument is that, in order to work properly, Agile can’t just be for software development. In fact, Agile can’t even just be for your project teams. Your entire business needs to be ready to adopt an Agile methodology.

The trouble is, this conflicts with standard business-model thinking. In his book “Maverick,” Ricardo Semler outlines the critical success criterial for modern business: “To survive in modern times, a company must have an organizational structure that accepts change as its basic premise…” He goes on to discuss the more ‘agile’ approach at his company, Semco, and why: “[W]e take an operation view of six months, because we found that in a conventional one-year plan people will invariably believe that conditions will improve just enough to compensate for the problems they know they’ll have in the first half of the year.”

How many of us have seem Semler’s point in action? In annual budget processes? In project planning? Somehow, some way we convince ourselves that whatever conditions that exist today will be “resolved” and we’ll be able to make up lost ground later. And so our plans are based on figuring that we’ve got a brief rough patch to get past, but once we do that, we’ll have 100% clear sailing. How often does that actually happen?

Of course, just looking out six months isn’t sufficient, either. At Semco, Semler and team have two plans: one with a five-year view to keep an eye on strategic planning, will the six-month view focuses on tactical execution. But isn’t this what we have come to recognize as the definition of “Agile Development”? A long-range goal that we approach in short bursts, one piece at a time.

But if we change “Agile Development” to “Agile Leadership” it not only allows us to approach application development with flexibility and agility, but also the way we look at the bigger picture. Development efforts — whether they are for back office systems, B2C web sites or client engagements — are a means to an end, not an end themselves. We recognize that changes to business conditions are a big part of the reason we get value out of Agile Development, but then we continue to approach management of our actual business as though it were static.

I was recently approached about a “four-year project.” Horrifyingly (yet predictably) enough, this was a Waterfall technical project (for a government agency). In technology terms four years is an eternity. The idea that any team (or group of teams) would be spending four years and tens of millions of dollars on developing and implementing a technical solution for anything is insane, because no matter how good your requirements are this year, by the time the project is complete (assuming it is actually complete in four years) the entire world will have changed. Four years is an ice age when it comes to technology, and it’s at least a lifetime when it comes to business.

So what would need to change if we applied “Agile” methodology to an entire business, intead of just the development teams? Consider this:

• Evaluate the business from end-to-end and examine how much is truly “operational” and how much is “project-based.” Your operating models, staffing, budgetary and expectations are all different for the different sides of the organization. And, in many cases, most people should have a mix of both to keep business moving while also getting new work done and keeping employee engagement as high as possible. But we need to truly stop and look at this, because without first understanding how much time people have to dedicate to project work, we never build realistic project schedules. How many project plans assume each team member spends 8 hours per day on the project? Does that ever really happen?

• All projects would be time-boxed to ensure that, even at their longest, nothing dragged on for more than six months. This could be done by breaking large-scale projects into multiple smaller projects all organized as a program, or by breaking a single long project down into phases. But no matter what, no one phase should ever last too long. And at the end of every phase, a re-evaluation is done before proceeding to the next. How often have we worked on a project only to realize half way through that the work was really no longer necessary? Aside from being an irresponsible financial sink hole, this is also extremely bad for team morale.

• Consciously examine the value of ‘domain expertise’ versus ‘fresh blood.’ As a career project professional, I can tell you that most leadership underestimates the value of giving a project team a new project — even if it’s the second or third phase of someone else’s project. The assumption that it is better to keep the “experts” in place rather than to get fresh blood looking at a problem is often assumed instead of explored. And while there can be some value, is the value found simply because the original team didn’t do a good job of documenting their work? Or is it just a simpler resource model. In my decade of project management experience, I’ve seen keeping the same team on a project for a long time do more harm than good. And I’ve seen very little formal evaluation done to ensure the decision was actually being made instead of merely assumed.

• Strategic initiatives like new product development make an agile approach particularly valuable. Market conditions change rapidly and outside factors can move a low-priority, nice-to-have product from the bottom of the list to the top of the list over-night. If you’re planning too far out in too much detail and with too much rigidity, then you are not leaving your team the ability to react quickly enough to stay ahead of the curve. In fact, even worse, if your planning goes out too far, you end up inadvertently discouraging your people from staying abreast of the latest trends and changes, because they get into a ‘heads-down’ mentality, focusing on the long list of things they know are going to be occupying their time for the next year plus. This is one of the ways that companies lose their edge entirely.

Budgetting may be the biggest one of all, because we have been conditioned by most modern business practices to think in terms of quarters and years. Quarter-by-quarter planning is often too frequent to be efficient, but year-by-year is often too far out to be realistic. And, worse yet, it’s not far enough out to be strategic. It’s a combination of timelines that often work at cross purposes: we scramble like crazy for end-of-quarter numbers, and then we speculate wildly when building out year-long budgets. And in the end, neither is usually very valuable to getting things done.

How many organizations with large expenditures on gasoline and/or natural gas of some kind had to stop what they were doing in the middle of 2008 and completely level-set their budget for the year, because the unprecidented cost of oil had made all of the year’s original numbers (no matter how conservatively planned) entirely meaningless? Trucking companies, airlines, agribusiness, shipping companies, etc. All of them, because at the end of 2007 when planning the 2008 budget, you would have been hard-pressed to find anyone who would have predicted that gasoline would top out near $150/barrel. (Hell, most people thought they were being generous if they budgeted for $100/barrel.)

I have seen two common outcomes to this process: either everyone spends weeks creating their budget for the next year based on wild speculation and generally accepted (often inacurate) assumptions, and then they are held to it kicking and screaming, missing one opportunity for market adaptation after another; or the organization stamps the budget as “FILED,” puts it in a drawer and never looks at it again, rendering the entire exercise valueless.

And while the 2008 oil roller coaster is an extreme example, this type of thing happens on smaller scales all the time. And so we plan optimistically and then make exceptions for all the things our plan didn’t account for. Josh Ross has an interview (ironically, shot the day after the mother of all recent unplanned disasters: the collapse of Lehman Brothers) called We Design For Possibility and Retrofit for Risk. And although he is specifically talking about Web 2.0 and information security, in reality that title applies to business in general.

We plan aggressively, assuming all will go acording to plan, and then we try to put out fires that errupt en route to our goals. Instead of sprinting in shorter bursts that allow less time for disaster to erupt, we take a marathon mentality that gives the world around us time to throw obstacles in our path over and over again.

Like so many other normal, mundane facts of our daily lives, the way we approach business is still largely rooted in Industrial Age thinking — it’s a model for which the Waterfall method makes sense. The time and cost to build something new is so high that you better make damn sure you know what you’re doing before you start. But as we transition from, as Chris Anderson puts it, the ‘economy of atoms to the economy of bytes‘ we trade in more and more investment cost for higher and higher opportunity cost. If we don’t start pushing ourselves to thinking, planning and acting like products of an Information Age, we will continue to pay the price for a lack of innovation and agility. And the more time goes by, the more of our competitors will make the change around us, the more we have to lose by burying our heads in the rubble of the Industrial Age.

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The hardest thing about leaving JetBlue last year was giving up the travel benefits that helped ease the difficulty of living 3,000 miles away from my family and so many of my friends. One of the things I’ve realized lately is that, even though I am really loving being in Austin, I have been horrendously homesick. This is the longest I’ve ever gone in my life without setting foot in California, and I’ve missed it. (Last time I was here was last year for my birthday, after our wedding in Las Vegas.) My family, my friends and the familiar sights that are always “home” to me have been calling to me recently more than usual, and it’s so nice to be here that I can hardly stand it.

It took a while to pinpoint the source of my acute homesickness, but I think it has a lot to do with working from home. It might not do it if I actually liked it, but since I really hate it a lot, it’s been weighing very heavily on me. When I’m working in a more traditional office environment, I find myself getting the social interaction that I need to be happy, and then I am less likely to be as homesick. I fear that, no matter what happens with our business, our clients or any potential employment opportunities, that if I don’t find a way to spend my days working in more dynamic, social environments soon, that I’ll go nuts.

I envy people who can work from home happily – starting with my husband, who vastly prefers it to working in an office. It’s just not something I am finding even remotely pleasant – to say nothing of it being highly unproductive and uncomfortable. It really saps my energy, it requires time management skills that I simply don’t know how to acquire, and it’s isolating and depressing in a way that I never honestly expected. Even worse, it’s starting to make me dread both work and the sight of my lovely, sunny, bright apartment because I’m starting to feel like it’s a suffocating prison with really big windows.

Web 2.0 Expo

I am looking forward to the Expo. I find it more than a little ironic: O’Reilly is in my hometown. When I graduated from college back in 1999, I spent a year doing everything I could to get a job there with little success. Finally, I landed a temp job in the call center with the hope that would get my foot in the door and I could use the opportunity to find something inside on a more permanent basis. Unfortunately, what I discovered is what a lot of people in call centers discover: being in a call center is often very pigeon-holing, and it is hard to convince anyone to let you do anything else. So when an opportunity at MarketLive (back in those days, it was called Multimedia Live) came up in early 2000, I jumped at it.

I didn’t particularly expect that nearly a decade later, I’d be back in a field so heavily dominated by the O’Reilly brand/presence. I’m eternally amused at the cyclical nature of life.

However, in addition to getting to see John (whom I speak with almost daily, but whom I haven’t actually seen in person in about a year and a half), this week does give me the chance to see the brilliant and talented Joshua-Michele Ross. During my last year at MarketLive, Josh, John and I shared an office together, while we were trying to get the Organizational Development team off the ground. Of course, Josh has gone onto some very cool things since leaving MarketLive back at the beginning of 2005 (just a few weeks before I left for New York), and though we’ve generally kept in touch online, I haven’t spent any real time with him since.

I always enjoy spending time with Josh because he’s one of those awesome people who always makes you look, feel and sound smarter than you thought you were. I honestly think that’s what makes him such an awesome interviewer (see his video interviews to see what I mean). Josh has so many IQ points to spare that he almost seems to inadvertently loan them to the people he speaks with, and no matter how brilliant someone is to start with, Josh manages to bring out the best in them.

It’s an amazing quality that I firmly believe is at the heart of why Josh will always be phenomenally successful at anything he does: because he has true humility, brilliance and generosity of spirit that makes brilliant, creative people flock to him, because they just want to collaborate with someone capable of enhancing their own abilities to a degree rarely possible on their own.

Of course, the fact that Josh has a fabulous sense of humor, is a great artist, a wonderful political mind and generally an extremely cool person to hang with doesn’t hurt. He’s also one of the only men I’ve ever met in my life who has truly spectacular taste in shoes.

Food, Friends and Family

As always happens when I come home – especially after it’s been a while – is that just about every meal during my stay is tied to a visit with someone. This is both awesome and a tad problematic at the moment, given that a newly self-employed person is not necessarily able to spend ten days in the Wine Country eating out at all of the delicious restaurants that scatter the rolling hills of my beloved hometown.

So, in the interest of not being a total mooch on my friends, and in the interest of helping keep from being an excessive burden to my parents, I always seem to come home and turn my father’s kitchen into Alora’s Restaurant. Happily this is an unspoken trade-off that no one seems to mind.

There is something truly satisfying about cooking for friends and family. I am very lucky in that I have a wonderful husband who never takes my cooking for granted, and understands that it is a sign of my love for the people in my life to make truly creative and delicious food for them to eat.

But when we were in New York, I didn’t have the opportunity very much because NYC apartments aren’t designed for cooking (so the few times I cooked for larger groups were usually at hubby’s sister’s place in Westchester); and in Austin we don’t know enough people (or have furniture for them to sit on), and so I haven’t had the chance to truly play hostess the way that I love. I may be looking forward to that aspect of this next week more than anything else.

Which means, maybe I should start my trip by visiting my own personal shrine: Trader Joe’s. You think they’d mind if I pitched a tent in their parking lot for the week, just so I can get my fix?

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Well, I have officially wrapped up my first SXSW experience. So, true to my project manager DNA, here are my lessons learned and highlights. First, the Highlights:

The person I wanted to meet most was Penelope Trunk. Penelope is probably the only blogger I read for entirely personal reasons on a regular basis (I guess it sounds weird to say I read a career blog for personal reasons, huh?).

She is also one of the few people who tends to give advice that I bears any resemblance to the type of work environments I’ve had in my life (tech startups, largely); and we have a number of other things in common, such as being the primary breadwinner for our family (and the associated sense of pressure and/or responsibility), being a reasonably a slightly bitchy and extremely sassy ENTJ who doesn’t really make any bones about liking to have things go her way; she has an inclination towards being a workaholic that has not always been helpful in her personal life; and her direct approach to damn near everything makes her an anomaly among her peers. She is also one of the only people who writes about finding and building relationships with mentors in any kind of tactical way.

Not only did I get to see her on a panel (full of men, of course) where she was routinely trying to bring up points that were too tactical for their taste, but the next day I got to spend a few minutes with her to do an interview that I’ll be writing for SCM tomorrow.

The ‘entertainer’ or bigger “social media celebrity” I wanted to see was Gary Vaynerchuk. Mission accomplished. As always, he was awesomely entertaining and tremendously energetic. Thirteen hundred people bounded out of that auditorium after he was done speaking on a high simply because of his contagious energy. Aside from being extremely enjoyable, it was an awesome study in the importance of presentation style and crowd interactivity.

From a business standpoint, the person I wanted to see was Tony Hsieh, CEO of Zappos. He’s a little shy and a little nervous and a little uncomfortable on stage, but it’s been a really, really long time since I felt inspired by a CEO and I really needed that. I needed to hear a leader talk about something that was meaningful and compelling and touchingly human. His difficulty entirely relaxing in front of a crowd just made him more authentic.

Intellectually, the person I wanted to hear speak was Chris Anderson (Editor-in-Chief of Wired Magazine, author of “The Long Tail,” and author of the not-yet-released book “Free”). I love hearing what smart people think. And so much of my current study is directly supported and implicitly explained by much of his work, so it’s always a shot in the arm to know that I’m not totally off my rocker.

In the ‘getting great ideas from smart people’ category, the list is too long to count — but the panel highlights for me were:

• Ditch the Valley, Run for the Hills
• Beyond Aggregation
• Politics, Technology and Pop Culture
• OpenID, OAuth, Data Portability and the Enterprise
• Cloud Computing: Defending the Undefinable
• Democracy, Design, and the Future of Work

Socially, I was delighted to see my old pals Morgan and Ryan, from my JetBlue days. Ryan is now with WMG, so Morgan is the only one of us left at JB, but it was great to even just get a few minutes with them to see what’s going on in their lives and hear some of the cool stuff they are working on. It was a great reminder that, despite the fact that I in no way miss New York, I do miss my friends there.

And that’s not even starting in all the people I got to meet face-to-face after reading their blogs and/or emailing with them. All very cool.

Now, Lessons Learned:

Happily, I followed all the advice and not only wore comfortable shoes, but the first two days I wore my sneakers with my inserts. Amazingly enough, my feet were really pretty good all four days.

Room A in the Austin Convention Center is about 86,000 miles away from the hub of Interactive activity on the 4th floor. You have to walk through Montana to get there. It takes forever.

Whoever designed the elevator/escalator/stairs situation at the Austin Convention Center needs to be shaken until his teeth rattle. Seriously, dude, were you on crack?

There is no good solution for the electronics situation at SXSW. They provide machines at several public stations, which is nice. (Though, they only have them at ACC and not at the Hilton, which is not as nice.) But if you are a writer, you really need your own. But when the battery dies, there aren’t enough plugs to go around. All in all, we were all struggling with the same problems. No real resolution unless someone builds a 16 hour battery.

Food options are great if you’re not ridiculously broke from trying to get a new business off the ground. If you are, then eating shredded wheat out of a ziplock bag in your purse has to make do.

If you arrive at ACC before 9:00 a.m. each day, not only do you get rock star parking, but you get plenty of time to get some coffee, get settled, catch up on email, and re-do your schedule for the day for the 12th time.

So, that’s all of the direct stuff. I’ll spend the next couple of days distilling several of the things that came up in more detailed posts. My mind is racing, but my body is wiped.

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Today seems to be the opposite of my previous two days. After deliberately taking everyone’s advice on taking a ‘go with the flow’ approach to the SXSW experience, somehow today has proven crazy-ass busy.

10:30 panel: Beyond Aggregation
This was a great panel where we got to hear wonderful speakers, including blogger Louis Gray, discuss some very tactical tips and tricks they use to sift through excessive amounts of online information, make their own content more findable, and how they track down the best content available for their own blogs/sites. There was a LOT of great stuff in this standing-room-only panel, and I’ll write it up in more detail in the next few days, once I’ve had the chance to test drive a few of the things they discussed. Very cool stuff, though, and one of the most practically useful panels I’ve been to so far.

11:00 panel: Start-up Management (technically a “Core Conversation”)
This was actually my back-up, because I had wanted to go to the CMS ‘showdown’ between WordPress, Drupal and Joomla. Unfortunately for me, so did a TON of other people and they were smart enough to get there early enough to get in the door. C’est la vie. However, having said that, Start-up Management was also worthwhile. The founders of Dogster.com (where I have a page for Zeka, and have for 2 years this week) discussed the growth of a startup where the founders go from developers to managers. Some great dialogue, and much of the same advice (on a micro-level) to what Tony (Zappos CEO) said on Saturday during his keynote: protect your culture; hire slow and fire quickly if you realize someone is a bad fit; don’t fall into the trap of ‘just find a warm body’ because you’ll regret it. Also some good advice for small company layoffs, working with partners, and managing a product roadmap.

Some of the interviews I couldn’t get slotted in yesterday are scheduled for today.

This afternoons panels (which I’ll update about later) are scheduled to be “SEO for Startups” and “Tools to Know Your Users” — of course, this is SXSW, so anything could change.

More later!

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Well, things have been crazy as I’ve been learning the ropes for my new roles: Principal & Co-Founder of The Indigo Heron Group, Inc. and Managing Editor of Social Computing Magazine.

Lots to learn and lots to do, much of which has taken it’s toll on my blogging efforts. I’m working on some new time management techniques to help handle this a little better, since I am constantly struck with great ideas I want to blog about, but then get frustrated at not being in control of my schedule enough to make it happen.

So, to that end, I’ve had a few interesting things happen lately, that impact both my new business ventures and this blog:

• I’ve been learning a ton about the Enterprise 2.0 space. Much to my surprise and delight, I realized that just about every job I’ve had in my career was in the field (in one form or another) — I just hadn’t thought about it that way. Aside from making me feel much more confident in my ability to tackle my new role, it also made certain pre-existing relationships very valuable and cast them in a whole new light.
• I had coffee with Susan Scrupski of ITSinsider, and in talking about a very exciting new project she is tackling, I had another realization. While everyone in this space has different underlying interests when it comes to 2.0 capabilities within business, what my main interest is in how SaaS and Cloud Computing have revolutionized small business — and not just by creating a ton of tech startups (though, that is a particular love), but how these new tools have changed the time to market and the reach of organizations that have previously been unattainable.

  What I love most is that something like QuickBase or NetBooks make it possible to help someone like my father run his small business without an unrealistic up-front investment; and that something like Twitter, YouTube or WordPress can allow him the opportunity to access the viral marketing capabilities that did not exist during all the years when I was growing up and my family was running other businesses.

• I have found some interesting opportunities, and have been making plans to do one of my favorite things: attend professional conferences. In addition to helping out with and attending Interactive Austin, I am also scheduled to be at South by Southwest here in Austin in March, and then make a trip home to attend Web 2.0 Expo (which is a triple bonus, since not only does it mean getting a visit home for the first time in a year, but it also puts me at precisely the right time to celebrate the birthdays of two of my dearest friends). And with any luck, I’ll also be able to attend the Enterprise 2.0 Conference in Boston in June. (I knew I’d miss working for an airline, but at the moment, I miss it more than I even imagined!)

So, in addition to working on all kinds of fun and exciting new endeavors (some of which I’m not entirely ready to announce yet), I’ve also decided that I’m going to write a series for Social Computing Magazine on (mostly small) business for whom “agile” is more than merely a development methodology. It is an operating philosophy for their entire business. And, as such, how does this influence the technology tools they use. Often times, we see this is a huge driver in the adoption of SaaS and cloud computing solutions, and so this is something I am interested in exploring.

If you have, work for or know of a business that has good examples of this — either as a consumer or as a provider — please shoot me an email letting me know. I’d love an introduction, because I’d like to speak to some different people who have found business value in this arena and who would like to discuss it so that I can write about it.

In the meantime, I’ll post more as soon as I have a few more things lined up. But for now, there is never a dull moment here in Austin!

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