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Thanks Wayne!: My interview on Blog Talk Radio

Wayne, you ask really good questions. As for me, two words: Chatty Cathy. To listen to our hour-long chat about the challenges of soloing. Check out Wayne Hurlbert's radio program on Blog Talk Radio. We talk about Living without a Net, Entrepreneurial Sins, and BlogHer. It was a pleasure!

Entrepreneurial Sin #6: Getting too wrapped up in the lead of our business story

More on the issue of trust, a continuation from my last Entrepreneurial Sin post.

A primary issue while at all of the jobs I've had--entrepreneurial or corporate--is a tension that my Midwestern ears can sense with deafening clarity; the disconnect between two people of different "power levels" within a company--sometimes determined by title or authority, other times by the stake or ownership of a company--where the "higher" level party assumes the other party is untrustworthy, or dishonest, or incompetent. I've heard statements like these that suggest that a relationship might rupture when it doesn't need to:

--"She didn't call me back when I asked her to; she's totally uncommitted."

--"I didn't like his tone when I asked for an update."

--"What do you mean, you're not sure? We need you on-board. If you're not sure you shouldn't be here."

And the uber-vague:

--"She's just not feeling me. I'm not getting a good vibe from her."

By the way, I commonly use the last phrase above. I fully confess, in my less-reflective moments, I've made sweeping judgments based on vibes, which are often influenced by previous, unrelated experiences and lunar cycles. But I digress...

The point is, we do a huge disservice to ourselves and to the people that we rely upon to achieve our visions because we question loyalty, interest, and, perhaps, our ability to make people passionate about our vision. At the end of the day, however, this needn't be an issue of trust. This is really about your story lead. Let me explain...

Entrepreneurial Sin #5: Failing to trust others as much as you trust yourself

I spent the first decade of my career ignoring my Midwestern tendencies. From the very first day that someone laughed at my flat pronounciation of the name "Eric," I was convinced that I needed to denounce my heritage of twangy vowels, blushing modesty, and blind trust in the good intentions of others. The last bit, I learned, was called "gullibility" out East.

I came home from work one day nearly a decade ago, my first week at a new job, sharing with my roommate the odd behavior of my boss, who had sat down with me and gave me what I only later identified as a veiled threat.

She explained to me how important it was that I "get it". I nodded in agreement to appease her but didn't truly understand what she meant. I noticed that many of the other people in our department were constantly present for our boss, practically camping outside of her office in order to get face time with her. I noticed that some people got things done with minimal effort, while others had to write proposals and get eighteen approvals before taking a first step. All of this struck me as inefficient.

"People who 'get it' are the ones who do well here," my boss said.

Back then, I could only feel subtext but not identify it. I knew there was a reason why my boss had said that repeatedly. I sensed that she was asking me "Can I trust you?" but I didn't really know how to seem trustworthy, just how to do my job. Meanwhile, someone who had started the same day that I had immediately "got it" and played along with our boss's whims. She checked in with our boss constantly, visited her office several times a day, shared vacation pictures and anecdotes, and adhered to what I was later to learn was the accepted behavior of someone who was trustworthy.

I decided to mind my own business and take what my boss said at face value. I also assumed that she hired me because she had faith in my abilities and in my intentions to do good things for the company. My actions would speak for themselves, I assumed. And yet, so much at that company existed beneath the surface. My decision to not give my boss the cues she required to trust me made me very isolated and lonely.

Entrepreneurial Sin #4: Assuming the worst

In honor of my Mother's 60th birthday today, perhaps she'll get a kick out of this installment.

My mother told me once about a recurring dream of hers, where she's standing on top of a skyscraper and her four kids--all under five years old in the dream--are falling off the building. Allowing any of us to fall is not an option; my mother finds that her limbs can stretch in Plastic Man fashion to catch each child. But rather than marvel at her ability to catch us when we fall, her underlying emotion in the dream is panic. What if we all fall simultaneously, and she runs out of appendages and can't catch us? She ended up waking up from her dream, not because she dropped any of us, but because she was so worked up over the prospect that she might.

God love my mother. She will always go down in history as a dedicated friend and devotee of her kids. Looking back on my childhood, her parenting goes down in the positive column of my life ledger, with a few tiny flecks in the negative. Those flecks are single moments in time, particularly in high school--a time when most teens attempt to spread their wings--when she reminded me of the many noxious fumes that a bird may encounter on the way to adulthood.

Mom didn't worry about the usual teen traps: sex, drugs, and general disinterest in safety. She tended to freak out about other things, that were more, well, unlikely.

"You're going to go into the city with your friends?" I want you to call me the MINUTE you get there. There are weird people in the city..."

"You're going to fly to Florida for spring break! But so many people are flying now; the plane's going to be SO HEAVY!"

Later in life, not much changed:

"You're moving to New York? What if you take the wrong subway to work and get lost?..."

"You're moving to California? There are EARTHQUAKES in California!"

All of her feared outcomes were possible, I suppose, but not likely, and, in my opinion, not worth mentioning to your kid. Rather than heed my mother I just brushed off her concerns as paranoid and did what I felt I needed to in order to satisfy my curiosity and thrive.

I used to joke about my mother being so crazy, but that's the cosmic joke that you don't discover until therapy or until you become an entrepreneur: Even the parental traits that you think you never adopted stick to some extent. What you resist persists.

I've never considered myself a paranoid person, though as an entrepreneur I have to wonder if I've become my mother.

Entrepreneurial Sin #3: Thinking too much

Anyone who knows me knows that I'm a planner. Planning is a habit that has had enormous benefits for me in the past. I recall, several jobs ago, when I was a Web producer and launched a Web site with a team of exhausted writers and developers. I spearheaded the content launch, which included integrating a content management system with the reams of content we'd been generating for months prior. Though the team was too busy to worry about making our VC-induced deadline, I fretted over it constantly. I was the thorn in management's side, asking, if we only have x weeks left till launch, we need to do y and z. I often sketched out workflows and had documentation--a map for management of what needed to happen to make our deadline.

We celebrated our soft launch at a San Francisco brewery and toasted our outstanding effort. One of the founders of the company remarked at how organized I was. "It's quite amazing," he said.

"Actually," I said, "it's quite chronic."

Sure, always being aware of where things are in a process is helpful in accomplishing a goal. But even after being successful as a planner, I knew that being so controlling of outcomes had a downside. Even though I had an answer for everything, but I wouldn't have called myself the happiest person in the world. I couldn't schedule Mr. Right to come into my life. Nor could I plan for anything truly visionary.

Entrepreneurial Sin #2: Postponing Joy

I met with a mentor of mine who founded a firm 20 years ago, and is now enjoying the fruits of her prodigious labor as a chairman, but no longer a manager, of her company.

"I'm making up for it now in my 50s," she said. But I wish I'd done things differently. My company almost ended my marriage and permanently affected my relationship with my daughter."

She'd started her business with a young child in tow. Twenty years later, she was still working on revitalizing the relationships that fell to the wayside. She was also making up for the physical damage of years of no exercise and unwholesome eating--she never had time to prepare meals or take care of herself.

Now, many pounds leaner and with ample free time to travel and take classes, she seems younger than me, certainly lighter physically and mentally.

I had to ask her, "What can I do now to prevent that from happening? How do I achieve more balance?"

Entrepreneurial Sin #1: Assume the world will end when you stop working

I have a lot to say about the Entrepreneurial life, I realize. Including what NOT to do. I'm particularly expert at that. This is part I of a series on Entrepreneurial sins. As with all of my series, I make no claims regarding how many installments this one will have. Enjoy the ride, however long it lasts...

I've always found that the most introspective periods of my life have occurred when I've had time for them. Back in 2002, when the start-up I worked at went under, and I had nearly a year of "consulting" and thumb twiddling, I read stacks of self-help books, wrote a book, meditated and went on long walks that ended with me grokking something new about myself.

Intermittently in early 2005, when I quit my job to take on meaningful work (without knowing what that was), and before BlogHer, I had days that were fully open to me for nothing else but writing and jotting down inspirations.

But lately I've been in a distressed state. I've never been busier than I am now, and yet I'm equally introspective, and the two are duking it out for supremacy in a death match that's begun to eak its way into my consciousness. The first signs were small meltdowns, pissiness, and then moments of downright despair over the course of my life. I had a few months when I could blame it on planning a wedding, but now I don't have any excuses. Friends would ask, how's business? And the answer is always the same, "Fine." And it's true. But ask me, "How are YOU," and the answer is "Confused."