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Encounters: People who don't live in "phases"

A very close friend insisted that I meet a woman she'd just met. She just had a feeling we'd get along. After many fits and starts--business trips, cancelled opportunites and challenges getting into the city at the same time--we finally managed to be in the same place at the same time. I'm all for serendipitous encounters, but I've made far less time for these encounters than I used to.

I recall the salad days of the Dot Com bomb, when we had plenty of time and nothing to lose from meeting people who may or may not be helpful to us. I met people on searches, some similar to my own, and could listen to them talk about their endeavors for the sake of listening. Years later, with a small business to help run, time was at a premium. I've learned a new skill lately of folding in these occasional encounters with official business meetings.

This friend of my friend's was traveling far out of her way to meet me. She'd moved to the Bay Area not long ago and had some challenges navigating suitable places to park in the city. I could have gone to her, I thought, feeling a tad guilty.

Over coffee (or an iced latte; it was a hot day) we talked about what we were up to. Clearly our mutual friend thought to put us together for a reason. I knew that my coffee date was working on her third book. I guessed that my friend hoped I would be a potential reviewer of it when it was ready, or could help her with a blog promotion strategy. As she spoke, I realized she hardly needed my help. She'd practiced medicine as an OB/Gyn for years, then decided to follow her passion for art. After creating a national following (she shows in galleries across the country), she thought to expand on her passion for writing. She is now working on her third book, which had received competing bids from multiple publishing houses. She didn't need my help with online promotion; her growing online community was thriving. She had a staff to help her maintain it. Three years ago she had  a daughter, and her husband, a Harvard MBA, had stopped working to explore his own possibilities and now spent his days at their home near the ocean.

I thought to myself, she has everything she wants. What can I possibly do for her? Perhaps, it became increasingly apparent to me, it was SHE who would help me.

What this "traditional media" expat has to say about the way the wind has blown

I am an ex-pat of traditional media. I came to my first job hoping that I would see my name in magazine bylines and book covers. Maybe I would get to share my work on TV, God willing. I left "print" by accident, not by any prescience on my part of its eventual declining significance, but more from an inability to fit in.

I'm sure if I had stuck it out a bit more and not taken a new media job five years in I might have made more of a go of it. But things discouraged me about traditional media. It had an established power structure that made it nearly impossible to get noticed. I wrote things I was proud of on the side, while editing more established writers in the waking hours and writing uninspired copy as a freelancer. But I hadn't really established a voice that was worthy of cashing in favors from editor friends of mine.

I didn't crackle with potential; I tended to get sleepy at work while copyediting and often had my edits edited. My favorite part of my job was reading magazines--a nice perk of working at a print media company--and going to parties, where a lot of people asked me for my card. Being employed by a large media company, I didn't have to go after editors looking for print work. But I had no ability to get published within my own company. When I was told I couldn't write good headlines it felt more like a sentence than a criticism. It was an indication of my inability to do well in this world. I wouldn't get to do what I really wanted--to write--because clearly it wasn't in my blood.

I read with fascination Lesley M.M. Blume's piece in Slate, "The Media's Lost Generation" about the travails of traditional media refugees who are being forced to have to re-invent themselves in mid-career. Her piece opens,

Last month, a media executive met with a headhunter to plan his next career move. With years of experience at a major media organization, the executive figured that he had some good ammo to jump to the next level, even in the current economic climate.

The meeting did not go well.

"The headhunter essentially told me not to even bother trying," says the executive. "He told me, ‘The old media model is broken.' The message was that there really isn't a next step to take."

I read articles about the challenges of print and television all the time, but this one really resonated with me, perhaps, because I'm relieved that through no particular flash of insight other than just a feeling to go where I can make a difference, I veered to where the action is. A direction now deemed "correct" in the world. I recall my decison to leave New York to take a new media job, ten years ago, and asking a trusted mentor whether it made sense for me to leave and relinquish my somewhat low, but higher than rock-bottom, place on the media ladder.

"You'll be back in six months. Don't lose any numbers," he said. My decision to go was one of the first logically inexplicable ones I'd made. It came from the gut and a voice that said, "Do it anyway."

I share this because I am not taking a self-righteous stance on the new relevance of new media, or social media. I make a living from it, I believe my company rides along the edge of best practices everyday, but I can't say that I knew this would happen; I'd only hoped I would be able to pursue this growing interest in a model counter intuitive to the people I used to work for. A model that democratized media, to a large extent, and made possible a notion terrifying to most people like me who hinged their self-worth on "making it" in traditional media: that there's a whole helluva lot of talent out there and it ain't all on the Hearst, Conde Nast, or Time Warner payrolls. Traditional media just took in whom they could fit, who matched the pedigree, or who had an uncle who could introduce you to the editor, or who had this random bit of luck and was seen for what she could produce, and sometimes bonafide talent. But so may others could not even make it to the filter, let alone make a living at it.

Back in my print days, there was something so alluring about being one of a few selected, whose name would be committed to print. And there's a whole community of folks, I'm sure, who still hold print sacred. I'm one of them, even as someone whose name has only made it via her work in new media. I fretted so long about being a part of it that even while it's suffering I promise to someday return -- if it will have me. Many bloggers who are doing just fine building platforms online still look at the book deal as the summit of success. I'll know I'm fully evolved when I couldn't care less about hardcover, softcover, or any cover.

Blume writes of executives who have dedicated their careers to traditional media and who now have no idea what's next. I recall from back in my editing days that the most likely way to "move up" in traditional media was to jump to a new company. I had friends whose resumes made me dizzy--they moved, often laterally, to a company, then another, sometimes even back to their original company. Anything to extricate them from a previously untenable working situation (untenable, meaning with blocked or unclear paths to promotion). Often their situation wasn't any better when they moved, but even the possibility of shaking lose a few additional thousand per year, or removing the word "associate" from their title was worth it. Movement in itself meant relevance.

But now, after swinging from tall building to tall building like Spiderman, these execs are finding themselves in freefall: The buildings have crashed down.

It's been difficult to share my thoughts on the overarching change that's going on, because it would be so easy to accuse me of advocating for the side on which my bread is buttered. But could any of us really read Blume's piece and think that we've ended up on the "right" or "wrong" side? I read it, felt lucky for a second, and then realized, no matter which side we're on, we can't stop moving. We must simply learn to love the freefall, even when at times someone throws us a net.

What I'm grateful for is not having ended up where I am, but for the voice that had told me, when I thought I should stay in the realm of the known, "Do it anyway."

The Accidental Entrepreneur

I never planned on being an entrepreneur. Independent contractor, yes. Freelancer? Uh huh. But an entrepreneur? I never thought I had it in me.

I don't consider myself a risk taker so much as a demander of work I feel passionate about. I'm ambitious, but you don't have to be a risk-taker to be ambitious. You can get all A's in school, graduate from college early with honors, get a graduate degree and thereby hedge your bets that you will be "successful" in the more superficial sense of the word--money and job opportunities. I've always been a hard worker, but that, too, doesn't mean risk-taker. Just why, then, am I an entrepreneur?

It was an accident. I found myself in a situation where the mission, the people, and the timing were right. We didn't think that the market was ripe for us, we just wanted to do what we did. We didn't think about positioning ourselves at that time. We just created what we thought was missing. We had the time and the energy. Considering all of these factors that just fell into place I'm amazed that I became an entrepreneur. The opportunities where pure passion meet a market where it can be leveraged is SO rare.

I'm reading a book, the Entrepreneurial Imperative. I've just started, so no major takes on it yet. But I am struck by the author's premise, which is we will only help ourselves through entrepreneurism. It's the only way, not only in business but in philosophy. We must be willing to take our futures into our own hands.

This can be interpreted in many ways: we can become entrepreneurial by bringing our passions to the workplace, or creating our own workplace if we can't bring them to our current ones. We must allow intrapreneurism (Nina Simosko writes an interesting piece about the origins and true meaning of this word) in our companies.
 
Applying this imperative to the current world situation, we need to allow each other to think our way out of what isn't working. Waiting for cycles of change isn't effective. What will happen if we all take our career lives into our own hands? Make our jobs. Think of our best way to serve.

Perhaps, then, being entrepreneurial would not seem so risky.

Back to my Roots: The Ladies who Launch Conference

For the past year now, I've spoken quite often about crossing the chasm between advertisers and bloggers. Earlier this year I was asked to sit on a panel for a Ladies Who Launch event in San Francisco to speak about, well, me, and my entrepreneurial journey--such a departure to discussing the merits of blogging, or the power of word-of-mouth marketing!

And yet, this event appealed to me in a way the others didn't. It reminded me of my days of yore, when I actually wrote about the seeds of creation, what brought me to starting a business with Lisa and Elisa, a pivotal time when your foundation for moving forward is built. A time when your previous world has blown up--it has to be blown up, or you'll spend too much energy trying to keep the past intact and not moving forward.

The event was not in any way a traditional conference-like format. Sure, there were panels and interviews, but in back were small businesses selling merchandise and lots of shopping. It turned me off initially--why do we always assume that if women are involved we need to have jewlery and cute things lining the place? But as I got to speaking to the women in the booths I realized they were a re-enforcement of the message behind this event: Anything is possible, and we can help each other get there. What better way of telling the story of your business than having your business brought to the event?

I spoke on a panel of media experts, including the hilarious Randy Peyser, CEO of her own business and author of Crappy to Happy, and The Write-a-Book Program: How to Position Yourself as an Expert by Writing a Book, and the epitome of Chutzpah. She told her story of following her dream and having nothing to show for it initially--except for a single box of baking soda in the fridge (been there!)--she opted to stand out on the highway with a sign "Editor seeking publisher." Incidentally, it worked.

The lesson from her story: It usually takes an act of faith (and insanity) to make a dream happen. And by the way, I could tell that being crazy was not a typical thing in Randy's life; she had to aspire to being crazy. A lot of people think that some people are born with the crazy gene and some aren't. I subscribe to a different theory, we are all born meant to be awake and alive, and those who go through this life without asking themselves if they are passionate about what they do are the ones who are crazy.

When asked about advice I had to making an entrepreneurial vision happen, I had a fairly amorphous answer; this is what I wanted to say: We are born with an obligation to ourselves to do what we are meant to do. Seeing our lives failing to commit to ourselves is often what pushes us over the edge. Personally, I couldn't stand myself any longer, and neither could the people who worked next to me. I brooded and complained once a quarter about not being utilized fully. Be warned: expect to be utilized on the entrepreneurial journey, OVER-utilized, in fact. Expect to have to do some outlandish things like get on airplanes and talk about things like you are the expert. Realize you are the expert and just do them.

Also on the panel is a woman I've been wanting to meet for quite some time--Kate Everett Thorp of Real Girls Media. Being the head of a digital media company, I thought I knew her story, but I didn't. Hearing Kate describe how her mother was instrumental to helping her commit to things at a young age, and how her husband left his work as an engineer to take care of their three children, I realized there are no easy peasy ways of becoming an entrepreneur. Some of us sacrifice more than others, some of us get funded sooner, but none of us had an easy ride. None of us did this without help. The more we tell our stories, the more we free up other women to take the plunge.

A handful of women came up to me, I had assumed, to ask me about blogging. Some did want advice. And three asked me, with shyness, what's a blog? I had to laugh appreciatively; I came equipped to tell of how blogging would increase entrepreneurs' visibility, but it seemed that my expertise was less interesting than my experience. The part I don't share in keynotes--how freaking hard it is to start something no one has done before. Working through uncertainty and learning much more about what you want through discovering what doesn't work for you.

One woman approached me whom I hadn't seen in years. I found it ironic that she'd approached me, since years ago I'd seen her speak, and later she'd become one of my inspirations. In fact, I wrote about her when I embarked on a previous entrepreneurial journey. Here's a snippet:

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 #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?"

A Reality Check for Female Entrepreneurs

My post on BlogHer about a women entrepreneur who makes my obstacles seem like boogers in comparison.