Today’s New York Times had a brief but attention grabbing article on its cover page titled “In Web World of 24/7 Stress, Writers Blog Till They Drop.” Greg Sterling responded before the sun came up in Oakland, Om Malik also responded, and Michael Arrington is quoted in the article saying, “At some point, I’ll have a nervous breakdown and be admitted to the hospital, or something else will happen. This is not sustainable.” It’s truly shocking to me sometimes how so many people I know, or know of, who are also so bright and intelligent, choose to work themselves to … well, to death. Don’t get me wrong, I’m including myself in at least the later half of that statement. I work 90% of the time I’m awake, and I, like Michael Arrington, have a sleeping disorder. I’ve been to neurologists for it and I’ve undergone sleep studies and the doctors ultimately conclude that I need to relax and get into a more consistent sleep schedule. So I’m guilty of it too. But I like to think that I’m getting better at it and that I do have some perspective.

Work can quite literally become one’s life, making the delineation between “work” and “life” nearly undetectable. Many of my own friends and family would say that CitySquares is Ben, and some might dare to say that Ben is CitySquares. Frankly, I find both of those assessments bordering on offensive, but I do understand their perspective.

What drives me might be different from what drives, say, Om Malik. What drives Om might be quite different from what drives Mike Arrington. And as an entrepreneur on my second business, and knowing many other entrepreneurs in varying stages, I can comfortably say that I know what drives me, but I cannot profess to know what drives them.

Over the past few year I’ve learned a good amount about balance too though. Sometimes a death in the family brings you back to earth, or the birth of a child – whatever it may be, but usually a major life event has a way of doing that – giving one perspective. I’d like to think that I don’t need a life event to remind me. Om Malik needed a heart attack to bring him back to earth. I’ve had some of my own personal wake-up-calls that I frequently use to keep my feet on the ground. I am constantly reminding myself that nothing is more important than family and health. And ironically, it’s precisely those two things that I’m working so hard for!

I’ve forced myself into a pattern of a fairly regular sleep schedule, which has significantly lessened the symptoms of my sleeping disorder. I’ve also learned to set time aside for the most important people in my life as well as time for myself. I’ve been practicing turning off the Blackberry, closing the lid on my laptop, taking a deep breath and just – letting go. But if I don’t practice balance, and it does take practice, than I start to forget why I’m doing all this, why I’m working so hard, why I choose this life – rather than this life choosing me.

This blog, Your Suspect, is most often about these very themes – these struggles between my own identity and Self, and my identity as an entrepreneur. I hope that this blog will tell a story one day, a story that I am living and that I plan on sharing with my own child.

I’m reminded of a line from John Lennon’s “Beautiful Boy”, Life is what happens to you while you’re busy making other plans.


A Tough Week

On a personal and professional level, this was one of my toughest weeks since the company was launched in the autumn of 2005. It was made especially hard because this week saw the departure of an employee who’s been with us since the start. It was awful in many ways and I found myself physically affected by it to the point of nausea, loss of appetite, sleeplessness, and when I could sleep, I had nightmares. It was truly a shitty week.

Additionally, I had to pitch the board on something and it didn’t go over with showers of rose pedals and applause. C’est la vie – I get my 2nd swing at it in a couple of days.

On a broader level, not just isolated to this week, we’ve had a hard time finding qualified sales people and in a couple instances made offers to people who just decided to not show up on their first day. Nice huh? It seems, though, that the dust has settled now. We’ve a couple new people who started with us this week and they appear to be taking well to their jobs and to the company culture – two things I watch very closely in those first few days.

Yet, Tuesday we had our monthly company lunch and morale is good and healthy! At lunch we went around the table and told stories about our most embarrassing work moments, or most demeaning jobs. There were some good stories told!

We’ve got a marketing intern starting with us on Monday and I’m actively interviewing to fill the newly opened role. We’ve got two more sales people scheduled to start over the next few weeks.

Anyway, the point of all this is that my job, for the past couple of years at CitySquares, has been entirely about building a business and a company, and it still is. We’re in ‘build’ mode, there’s no two ways about it. I enjoy that work greatly. Now that our staff is in the double digits my job is becoming increasingly more about managing the organization. I also enjoy that work greatly. I think I’m good at both of these things, which is why, ultimately, I enjoy being an entrepreneur and CEO. My previous company saw about 12 full time staff at it’s peak, but dozens of contractors around the country, nearly all who reported directly to me. I also was the direct contact for most of our customers. I greatly enjoyed that work, the hustle of it all. It makes me wonder too though, about those entrepreneurs that aren’t able to make the transition from founder/builder to manager/CEO.

So back around to tie it all off – it was a tough week, the worst yet. Unfortunately, as a manager, tough decisions need to be made. Unfortunately as a CEO sometimes you gotta take a few jabs from your board. But at the end of the day, this is a business, that’s the bottom line. And at the end of the day I need to be able to look at the books, look at my board, and look at my staff confidently – knowing that I’ve done the best job they expect from me. I have to be accountable. It’s not easy, I didn’t sign up for easy. And I also need to be able to look at my own reflection and know that I’ve done the best job I expect of me. And the two are not separate – they are the same.

So to wrap it all up I thought I’d share a funny video that someone sent me on Monday – the timing was great. This person had no idea that I was entering a shitty week either, just really good timing on their part.