Photo Credit: Chez Andre on Flickr.

Entrepreneurial Priorities if You Don’t Want to Despise Yourself at Age 80

With the exception of a general, “We’re hiring” post a few days ago, my site has been largely neglected for the past year. It’s not that I don’t want to write. I do. And it’s not like I don’t have things to say because, if you know me, I do. I really do. And it’s not even that what I’d like to say isn’t all that important…. because it generally is.

I feel the need to write today, however, because it directly relates to why I don’t write as much as I used to. And it directly relates to why I, in the eyes of the typical startup founder or venture capitalist, am not a great entrepreneur. In their eyes. I’ll admit that I’m a terrible day to day running a business guy. I’m a terrible “take care of the basics” like health care and witholding taxes” guy. I’m actually a pretty decent entrepreneur though. Put me on the phone with a prospective client, and I can speak their language and close a deal. At the end of the day, being an entrepreneur is all about making money so you can live to play another day.

Or is it?

It’s also about life and lifestyle.

I feel really compelled to write about this because, though I sorta took a mental break from the tech startup world for a bit while I focused on my job and my new life back in on the east coast (and, you know, survival and keeping a roof over my head), I’ve dipped my toes back into the water.  I am as alarmed today as I was two years ago about the entrepreneurial scam that is peddled by basically everyone.

There’s an entrepreneurial scam?

Funny you should ask! Yes. And it goes something like this: “If you’re not willing to give 24/7 to build your startup or company, you shouldn’t be an entrepreneur”.

Jason Calacanis, famously, said in one of his listserv emails on September 27, 2008, eight days after the market crash of September 19, 2008 and two days after the FDIC seized Washington Mutual Bank, that the sign of someone (paraphrasing here) worth being hired/invested in in the startup world is the person who will gladly come in on Sunday. This was the actual passage from that email:

Hold an optional off-site breakfast meeting on a Sunday and see who shows up: If folks don’t show up for you to grow/save the company on a Sunday for a two hour breakfast, they probably aren’t going to step up when the sh#$%t really hits the fan. You need to know who the real killers on your team are and you need to get close with them now. Again, it’s fine to have 9-5ers on your team–if you’re the Post Office. You can’t have them at a startup company. Note: if you reading this and saying I’m anti-family, save it. Folks don’t have to work at startups and some of the hardest working folks I’ve met have families and figure out how to balance things.

UGH. So much wrong with this sentiment. This sentiment screams, “I am what I do” and that is simply the most self-loathing sentiment you can have. It is neither something to be proud of nor is it healthy mentally or physically. I have a lot of respect for entrepreneurs who will go to the Farmer’s Market on Sunday morning. Or who take their kids to the park. Or who go to brunch with their husband/wife/girlfriend/boyfriend. Not so much for the person who opts to work instead of doing these things.

Here’s what that mentality of roughly 2003-2008 got me. It got me a career, yes. It also got me a divorce and years of my life I will never get back. At nearly 38 years of age, that is a lot to bypass in the service of the almighty dollar, ego, prestige and “fame” (whatever the fuck that means).

While I worked my corporate 9-5, I was coming home and then working another 8 hours on client works, building a company or other nonsense. I neglected my son (who fortunately still loves me to death) and my wife, at the time, by working every night until 3am just to pass out exhausted and wake up at 6:30am to go to work again.

Those lost opportunities to be present were squandered because I bought into the charade that if I work longer and harder, I’ll succeed more and have a better life. Rubbish, hogwash, nyet, NO!

After my ex-wife and I split, I naturally did some soul-searching. Work wasn’t our only problem. But I’d say it was a contributing factor to all the problems I could see. I decided to do a 30-day “work cleanse”… For 30 days, work normal business hours – 9-5, 10-6, whatever… and then put my work down and find something to do to occupy my time. That was a hard thing to do since my work was my identity and my habit. However, after 30 days, I realized I was feeling more energized. I got more sleep. This enabled me to focus better on my work when I was doing it. It helped me get things done faster. I felt more alive.

By and large, this 30 day drill has become my lifestyle now six years later. I typically still work Monday through Friday, 9 to 5. I avoid after hours work or weekend work if I can help it. Though I still take side work, one project at a time in digestible portions, because… a little extra cash every month is nice. But, today, I spend time with my girlfriend, cook dinner sometimes, and do stuff that is fulfilling to my life (usually!) instead of investing all my energy into something that will ultimately fade away.

My greatest fear is that, in my latter years, I will look back on my life with regret, building something that doesn’t last while sacrificing the things that really matter on the altar of snake oil salesmen. You are not what you do. Your time spent does not define your character.

In the words of Trent Reznor Johnny Cash, three months before his wife’s death and seven months before his own:

What have I become 
My sweetest friend 
Everyone I know goes away 
In the end 
And you could have it all 
My empire of dirt 
I will let you down 
I will make you hurt