As the old joke says, “There are two kinds of people in the world…” In my corner of the universe, there are those who love working in/with startups and those who don’t. Those to love it never question why someone else likes it. Those who have either never done it or who have low tolerance for chaos rarely understand it.

This question came up again today, and I found myself — once again — struggling to provide sufficiently insightful answers to the questions about why I like highly chaotic startup environments. And, once again, I have found that the people I speak to are often convinced that their startup is the most chaotic in the world. There is often enough of a badge of honor built into that assumption that I try to avoid disillusioning people by pointing out that it’s probably pretty unlikely that their brand of chaos is any “worse” than that of other startups.

But the fact is that everyone assumes their brand of chaos is the worst. I spent five years at a self-funded ecommerce startup and most of the time I was there I had two official jobs. Every couple of years I would change roles, but yet it would take more than a year to offload my old one. But, I was young and hungry for opportunity, eager to prove myself and perfectly willing to take on that insane level of work (despite my staggeringly small paycheck).

Later in my career, at another startup — this time an airline — I found myself (along with all other employees who worked in HQ) standing at JFK international for five days dealing with irate customers in the most face-to-face manner you’ve ever seen in your life. Those five days cost the company over $30 million. The results of that, of course, were more chaos: the Board ousted the CEO, and the entire organization set about a massive set of initiatives designed to prevent that level of chaos from ever impacting customers again.

And yet, despite years of sleeplessness, no social life, below market rate salaries, extreme stress and constantly disrupted vacation plans, I keep coming back to startups. Why? Because, as one of my former bosses always used to say, there is opportunity in chaos. Tons of it. There is always far more opportunity in chaos than in calm.

People who seek out calm, mature, stable environments do that because it is important to be able to walk out of the office every night at 5:00 p.m., it’s not because they are looking for unforeseeable opportunity born out of crazy left turns and unpredictable technology shifts.

Everyone I’ve ever known who has an attraction to startup environments does so because the surprises and opportunities are addictive. Knowing that things can change on a dime, that a large new client can change everything, or that a new product will open up all new markets, knowing that the person on your left is the entire sales team and the person on your right is the entire QA team means that some days you’re going to have to pitch in an help someone who does something different than you do just to make it through the day.

To be sure, people who like clear roles and responsibilities, defined priorities, clear-cut areas of expertise, and a regular, stable schedule that they can easily predict and painlessly plan around should avoid startups.

But in all my years of going from startup to startup to startup, the two kinds of people I have seen who thrive the most in highly chaotic, rapidly changing startup environments are:

1. People who bore easily, and who need a constant influx of stimuli to stay interested and engaged. These people are usually extremely smart and creative, and seek out environments that are unlikely to box them into anything too confining.
2. People who don’t know what they want to do. I most frequently see this among recent graduates who are not yet sure what career direction they want to take. They are often interested in a number of different things and are looking for a professional buffet they can sample from for a while before settling in on something specific for the long haul. This is often easy to maintain while you’re young, single and full of energy. But often this group settles into a discipline, gets a little older, starts a family and becomes a little less drawn to the chaos.

I fall into both camps. I started off in the second group: young, eager and entirely unclear what I wanted to be when I grew up. And then after doing it for a while, I discovered that was the type of environment that was providing me the level of stimulation and motivation I needed in order to really love going to work every day. And the times I’ve tried working in environments that did not meet that need all ended quickly, because no amount of cushy paycheck could make up for being bored out of my mind.

Of course, I’m not 27 anymore; 18 hour days take their toll more than they used to and I’ve got a husband who is most certainly not a workaholic and has this crazy expectation of actually seeing me from time to time. One could generally argue that I should have probably grown out of my addiction to the chaos by now.

Perhaps. But the fact remains that until I can find another type of environment that provides even a fraction of the array of opportunity, I’ll keep gravitating back to startups specifically for their chaos.

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This is something I’ve been thinking about more and more recently. The fact that we started off as a services company is what allowed us to get started and to avoid having to rely on outside funding. But it was transitioning to a product company that allowed us to grow and scale, and to ultimately attract funding. However, the transition from one to the other was brutal. And looking back, I can see a thousand opportunities where we could have done a better job.

When the bubble burst back in 2000 it was because speculation had driven realistic performance expectations, sanity and reason out the window (keep throwing endless piles of money at most people, and eventually most of us will get stupid). The industry itself, as well as those watching and investing in it, had bought into its own hype, and then it was crushed under the weight of it’s own hubris and lunacy. (Not unlike what is currently happening to the financial services industry.) Critical lesson: watch the hype and don’t drink the KoolAid. (A caution I would also issue to the current level of hysteria going on in the social media space.)

What this meant, of course, was that companies that had not yet become profitable or did not yet have a self-sustaining business model were S.O.L. VC money evaporated over night. Gone were the massages and catered lunches and lavish holiday parties. Suddenly we were awash in pay cuts, layoffs and absorbing the workloads of people who’d left because we couldn’t afford to replace them.

We were lucky. At that point, we were still a services company (though we were working on our product; it just wasn’t done yet), and that bought us a little bit of time. Not a lot, but — as it turned out — enough. And we sold our asses off. Everything we did for clients was billable. Everything was custom. Everything was a one-off.

Naturally, this presented problems in the scheme of things, because while this was providing us with live-saving revenue, this was not at all scalable. And our leadership knew it. So we continued to push forward with our plans to transition into being a product-based business that offered additional, ancillary services.

The troubles here were strategy, communications, education and execution. For those of us who were living on the services side, we had a culture that was services-centric — not product-centric, and there is a huge difference. In a services-centric culture, your answer to clients is always “yes.” And clients expect your answer to always be “yes.” It never occurs to either of you that the answer could or should be anything else. There is a culture of expectation that must be transitioned, and it must be done thoughtfully and carefully in order to avoid alienating the very people who are keeping you in business.

Now, to be sure, you aren’t going to have a business if you get in the habit of saying “no” to your customers, but there is a big difference between being an order-taking organization whose response to “Jump!” is always, “How high?” and an organization that provides expertise and consultation to customers, as suppliments to a core product offering. The culture, the relationship, the value brought to the table are all very different. And shifting from one to the other is a significant change that needs to be managed carefully in order to keep both your staff and your clients onboard.

Furthermore, our problem was compounded by the fact that the product team was very insulated from the rest of the business. That include socially. They literally sat in a different building. The two groups barely knew each other, so not only did both sides feel misunderstood and taken for granted, but we did not have the opportunity to really find any solid common ground. The services teams thought the product teams were snobs; and the product teams thought the services teams were cowboys. And we were probably all at least a little bit right. But what we weren’t seeing is that each group had a different mission, and that we were each very much in-line with what we needed to be doing at that time.

What we didn’t do was actively execute against a long-term strategy to bring both teams in-line with each other. To whatever degree that did ultimately happen, it was more by brute force of circumstance than by much in the way of active planning or cultivation. Looking back now, so many of the conflicts, headaches, and missteps are painfully clear. And, since hindsight is 20/20, I see so many opportunities that were missed, that would have made all the difference — both when it came to the internal culture, as well as in our relationships with clients.

Of course, looking back, I also now realize that this was one of the early seeds that sparked my interest in change management. This was a big change that had do-or-die implications for the business. The sense of urgency and relevance needed to be truly understood by the services team to get their buy-in, and it simply wasn’t. Without that comprehension, managing client expectations was an endless series of bungled missteps that were constantly needing to be corrected. The services teams needed a roadmap; and we didn’t even have a compass.

Another reason that I love startups is that, given enough time, I know that I’ll have the opportunity to tackle this type of problem again, and be able to apply some of the hard-won lessons from last time to doing it better.

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I find it amazing that the times when I typically realize I am having the best days are the days when I am peddle-to-the-metal, no-holds-barred, hair-on-fire busy as hell. Why is that?

Today was spectacular… and I’m not entirely sure I can adequately quantify precisely why. I think the bottom line was that I had one specific meeting with my boss in which, not only did I get good insight into his plans for me (and my career development), but I had one of those moments that led to a bit of an out-of-body experience, in which I heard myself and our conversation and I was blown away by the fact that I just sounded GOOD.

And, given the conversation we were having and the project we were working on, I absolutely loved being involved. It was a tremendous sense of collaboration, which I’ve missed. Even more, though, was the access. One of the things that has been hard for me at this job is that I am used to being a much bigger fish in a much smaller pond. Here I am a little fish in a big pond. The CEO has never heard my name, couldn’t pick me out of a line-up with a gun to his head, and probably doesn’t have the first idea what an IT Project Manager really does. I’m used to sharing an office with my VP and having weekly meetings with my COO. It’s a world of difference. And — aside from the logistical realities that go along with no longer having that kind of access — it has been just generally hard on my ego.

Now, while I still don’t have that kind of access — hell, I couldn’t even swear that my CIO could pick me out of a line-up — the fact that my relationship with my Director is getting better and better, that I’m becoming more and more involved in strategic development and organization, and that I am finding myself involved in conversations that are truly exciting and interesting about how we are going to manage the division going forward, absolutely gives me goosebumps.

I look at the three Managers on my team who are technically two rungs higher up the food chain around here than I am, and two of the three of them are less mature management stock than I am. And the third one suffers by virtue of geography, because she is 2000 miles away, and not in a position to be involved in the impromptu types of efforts that evolved quite naturally, and which are rife for this type of relationship cultivation opportunity. The two boys, though, are each very strong in some areas, but also very clearly in need of some extensive development in some other areas. And while both of them definitely have the potential to be good, strong leaders, in the immediate term, they are not always in a position to help with some of the brainstorming and organizational development analysis that I’ve suddenly found myself in a position to become engaged in — which is phenomenal, because that is what I love more than anything.

In any event, today was a really, really great day and I’m finding that I am still on enough of an adrenaline high that I am not ready to go home yet, which I should do, because I have a ton of work to do that I am suddenly re-motivated to tackle.

It’s been since mid-2003 since I’ve had a day that got me this pumped. I almost forgot what it was like. Now that I am feeling it again, this is a reminder to me how I found myself working 80 hours per week. It’s like a runner’s high: you get addicted to it and then you push yourself longer and harder and faster than you should to try to get your fix. Unfortunately, just like with runners, you can take it too far until you just collapse (which is what I did). It’s been 3.5 years since then, though, and now maybe it’s time to see if I can dabble a bit without finding myself totally hooked and out of control drunk with the adrenaline again. Should be interesting to see.

One thing is for sure, though, and that is that there is a reason that I was single back when I was in that pattern. It does not work with a love life.

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