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?

Grant me strength to accept the things that I can’t change, the courage to change the things I can and the wisdom to know the difference.

Since 2003, I have been working really, really hard on changing the things I can change. Everything from my work-over-life habits, to my physical health, to my determination to stay in my hometown because it was too easy to bother doing anything else. “Change” has been my mantra.

But it’s also been my addiction, and this gets me to where I am now. I got in the habit of changing things just because I could. I was enjoying the novelty of that, and was finding it invigorating. I still do a lot of times. But, now I have a husband who likes things to be a bit more stable than that, and I have realized that — much as I like to think otherwise — there are some things that I haven’t really changed, no matter how much window dressing I put up to try to make things look different.

This is particularly true in some of the most frustrating areas of my professional life. In the past, I have been notorious for being passionate, a bit volatile (a “bit”! Ha!), inclined towards taking things personally, having no boundaries, etc. Since late 2003 I have been working on all of those things, and some of them have been harder than others. But there is one area that no matter how much effort I put into it, my internal needle doesn’t seem willing to budge. And that is my ability to fake how I feel about something.

One of my strengths is that, when I feel strongly about something, I am a force of nature. My commitment level is unparalleled, my ability to motivate anyone is unmatched, and my energy level is uncontainable. My husband, my former bosses and co-workers and my friends all tend to enjoy seeing me this way, because my energy and enthusiasm is contagious, and they all have found themselves swept up in my tidal wave of excitement.

Of course, it is the other side of that coin that tends to be a problem. When I am unhappy in a given situation, I have a near impossible time containing it. I really try, but I could never be an actress, because the one thing I can’t do convincingly is fake emotion on demand. And the more unhappy I get, the less I can contain it. This gets me into huge, huge amounts of trouble. It has caused me to leave jobs, even when it was not necessarily in my long-term best interest. It has caused me to burn bridges I didn’t necessarily need to burn.

But, because it is something that I have been adamant I need to control, I have spent years trying to convince myself that it is only a sheer force of will that stands between my normal patterns and new ones. And now I’m not so sure.

I look around me at the people who make awesome consultants. They are people who can fake interest and enthusiasm so well they deserve an Oscar. Because I have spent years wanting to be a consultant, I have tried convincing myself that I was capable of that, too. But the more time goes one, the less convinced I am of that.

I have some dear people in my life — husband, mentor, friends, father — who have ridiculously challenged relationships with time. And no amount of effort fundamentally changes that. So the shift moves from CHANGING it, to MANAGING it.

I think this is where I am when it comes to my ability to fake my emotions. After years of trying to convince myself I could CHANGE this about myself, I think I have now arrived at the conclusion that the best I can hope to do is to MANAGE it, instead.

So what does this mean? First and foremost, this means that I start listening to my gut and not trying to convince myself that, by sheer force of will, my brain will be able to over-ride all of my emotional reactions. When I feel that familiar feeling that I am setting myself up for a disaster by trying to force a situation that fundamentally makes me unhappy, I need to stop and GET OFF the bus. For years I have continued to let myself be boxed in tighter and tighter, and then eventually, I end up exploding. And when that happens, I make a bigger mess than I ever needed to.

If I had walked away when I first noticed the signs, an amicable parting has always been possible. It’s only waiting too long, until tempers are running hot and patience is running out, that things become unsalvagable.

So, now I find myself in a strange position: because, like I’ve written before, I don’t like to quit, am I being a quitter by accepting that I may not be able to change this about myself, and focusing instead on management? Or am I being a pragmatist who is owning her short-comings and recognizing that some things really aren’t ever going to change?

Probably a little bit of both. I know I’m not going to give up and just universally accept that just because it’s hard that I can’t change something; but I also need to recognize that some things just need to be managed, and deluding myself into thinking that I can bulldoze my way through something is arrogant and impractical — and tends to make life more complicated than it needs to be.

So, for now I focus on management. And, the truth is, when there is something that I get truly excited about, my inability to fake my emotions serves me very well. And I’d be afraid that changing one side of that coin could have an adverse impact on the other, too.

“I don’t really care about it, as long as it works.”

The IT Version: “We don’t need more help desk staff. Make do with one person per shift.” The first time someone with a “C” in their title has to spend 45 minutes on hold to have their network password problem resolved, suddenly the importance of support desk headcount takes on new significance. Or (another favorite) what about the exec who thinks the top-of-the-line SLA package is “too expensive” — until a mid-day outage doesn’t get resolved “fast enough?”

The Government Version: “Tax cuts! Tax cuts! Tax cuts!” And then after standing in line at the DMV for two hours in the middle of the week, all you hear from the frustrated people watching their day slip by is, “How long does this have to take?” And, “I can’t believe they only have two people on shift when there is a line out the door!”

The problem: The things in life that we take for granted are often the ones we most resent paying for — and then we get mad when we are inconvenienced because of it. How many people surf on their neighbors’ wireless and then get upset when it goes down and they suddenly have no internet access? Ditto with pirated cable, or free coffee at the office that suddenly goes away when times are tight. We develop a sense of entitlement that makes us react very emotionally to change.

“It’s a bottomless pit with no ROI.”

The IT Version: Email Servers and Corporate Network integrity are the “plumbing” items in an organization that people often forget need constant care and feeding to stay healthy. But organizations rarely have a good way of calculating the cost to the business if either one of things fail. People have become so used to taking them for granted, that they stop thinking about them as systems with risks that need to be managed. Even worse, when times are tight we get in the habit of cutting back as a “temporary” measure, and end up neglecting routine maintenance. And then when things eventually blow up, we have a much bigger bill than anyone was expecting.

The Government Version: Public works are the government version of “plumbing” that people just expect to be there, but never seem to be ok having to help pay for. We all want smooth roads that don’t mess up our car’s alignment, we want to turn on a light switch and have the electricity work as we expect and we all want to know that when we turn on the faucet that the water coming out of it isn’t going to give us cancer. And the idea that we should continue to waste billions of dollars per year in electrical outages due to an over-taxed, patch-worked national electrical grid that we’ve outgrown instead of building a modern, more efficient one that more closely meets our needs is somehow a “dangerous” sign of “big government run amok.”

The problem:Infrastructure is not a one-time cost. It’s a big up-front cost followed by on-going maintenance costs. And after a while, it’ll take another big up-front cost, because whatever solution you put in place will eventually be so out-dated or so far beyond repair, that there will be no choice but to replace it. Duct tape and bailing wire are short-term band aids, not permanent solutions. We often make penny wise, pound foolish decisions as a result of procrastinating tackling big problems — and then get upset at the cost. (“Who needs to pay $40 every three months for an oil change? What a rip-off!” Until, of course, you’re stranded on the side of the road in a blizzard waiting for AAA to haul your car to a garage where you find out that your warranty is void because you haven’t had an oil change in a year.)

“It’s too expensive. Why can’t you do it for less?”

The IT Version: Hardware is expensive. Software is expensive. Trained staff is expensive. So we cut back. We outsource. We consolidate roles to hire fewer people. We buy off the shelf instead of customizing. We learn to work around inefficiencies in order to ‘make do’ without stopping to calculate the cost to the business of each employee wasting X hours per week on something that could be automated for $Y. We focus on tactical, short-term need instead of strategic, long-term value.

The Government Version: Programs are expensive. Staff is expensive. Systems are expensive. Taxes are unpopular and tax cuts are always popular. So we cut trim programs to cut taxes. And then we get upset when, after standing in line for two hours at the DMV, the frazzled clerk behind the counter has to fight with a 15 year old dot matrix printer feed jam and we can’t just be on our way. Even worse for all of us is the fact that, when it’s time for an organization to hire new employees, most of the best candidates are going to look around and decide to take the job or not at least based in part by the environment. And environments where they are going to have their hands tied by ten year old technology or are being told that they can’t get to Google to look things up as part of network security procedures is something that drives the best candidates away.

The problem: For the first time in history, people have better technology available to them at home than they have at work — and part of the reason for that is cost. The ‘personal use’ versions of technology solutions are often small enough that we gradually get used to incorporating them into our regular budgets (think cable TV or cell phones: once upon a time, no one would have thought paying for either would be “normal” for the average person). However, the enterprise versions for solutions are often very, very pricey and many times organizational leaders (in private industry and government) never quite recover from the sticker shock.

“What do you mean we need to implement something new? That current solution is only ten years old!”

The IT Version: “We paid $10 million for that solution back in 2002 specifically so that we wouldn’t have to replace it until at least 2012. Why are you asking for money to replace it now?” This may be the hardest ones for non-technical leaders to understand, but we do not live in a mainframe world anymore, where you can make a single investment like that and then expect to nurse it until you’re old and gray. IT investment now, though in many instances much smaller on an individual basis, is more constant, because disruptive technology (to say nothing of an entire wired workforce) forces adaptation at a rate previously unknown.

The Government Version: Government has a double-whammy in this regard, because in addition to facing this argument when it comes to traditional government services (i.e. rising health care costs for agency employees and Veterans) that are blowing out previously committed budgets, but they also have the IT problem within government itself: citizens are used to being “customers” who have access to a certain degree of services (many of which are technology driven), and then get frustrated when they walk into a government agency and have to fill out a form by hand, in triplicate, so that someone can crawl around a storage room for two hours to find a box that has the record we are looking for, and them make us a low quality photo copy for us to take home.

The problem: The budgeting process, in both government agencies and most corporations, is reflective of a long-dead set of business and technology models that no longer apply to how organizations work — largely because of end user expectations. Yet anyone who has been in either a large company or a government agency is all too familiar with the painful process that demands a lot more creative writing than actual concrete predictions, and usually for too far out. Sure, we can predict roughly how many Windows licenses are reasonable to expect for the next year or two, but saying that we are going to redesign the website this year with the expectation of not needing to touch it again for five years is ridiculous.

I’m sure that many of these parallels can be applied to other industries, as well, but as a political junkie and a technology professional, these are the ones that are most readily visible to me. And, as with most things, what this often leaves me with is a sense of resigned frustration at the predictability of the human animal — because these issues, at their core, are about attitudes, resistance to change, and sticking to doing things the way they’ve always been done, regardless of any real track record of success. And those are always the biggest management hurdles, no matter what your industry.

Agree? Disagree? Did I miss any other parallels? Leave a comment to let me know!

For starters, it quickly became very clear how many of the core themes and values David Neeleman took directly from his experience at Southwest and used when founding JetBlue Airways. (“Treat your employees right and they will treat your customers right” is one of the core tenants of JetBlue, and it came directly from Southwest.)

What was equally clear, though, was that Southwest has more infrastructure in place to support, maintain and develop those underlying themes and objectives. They have more resources dedicated to those efforts full-time, and they aren’t as reliant on just SAYING that something is a certain way and assuming that if they say it enough, it will automatically make it so.

While I found the entire presentation extremely powerful, I also found it a bit sad and frustrating: the things that make JetBlue a great place to work are the things that seem to be most taken for granted, like the culture and the values. And it’s not that those things are actively promoted and encouraged, but they are ill-defined, unmeasured and unmanaged.

Maybe I’m just too much of a business geek, but how can you promote something that you aren’t consistently and actively quantifying?