Opportunities in Chaos
This is my site Written by Alora on September 16, 2009 – 8:22 pm

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.