From Here to Autonomy

Aliza Sherman's confessional post makes me wonder: How Am I As a Boss?

This week Aliza Sherman gets my Entrepreneurial Cojones Award for her post on Work It, Mom, "I was the boss from hell." In this post, Aliza--an entrepreneurial superpower in my book, whose candid take on building a business and a personal life are inspiring--takes on a ghost from her business past: her first business. More specifically, her ineptitude as a manager.

Ten years ago, I was running my first company, and I was in a bad place in my life despite being in an excellent place with my company, at least on the surface. Although I still don’t have a full picture of how my employees at the time saw me, I get bits and pieces as I reconnect with some of them over time, and the picture is not pretty.

Some suitable words to describe me as a boss at that time would be:

    * impatient
    * paranoid
    * angry
    * frustrated
    * bitchy
    * demanding
    * irrational
    * emotional
    * disempowering
    * unpredictable
    * insensitive

Aliza uses this post to apologize for this behavior (something I dream about seeing from bosses in my past, but that's another post), and to point out the stresses in her life that made her a bad boss. The point of this post is not to excuse her behavior, but to allow other entrepreneurial women to understand how some common, and not so common, stresses can lead to bad managing. Frankly, I suspect Aliza is being somewhat hard on herself, but I appreciated this candid, useful piece.

While I don't have the same issues as Aliza did, I could relate to the fact that not all of us go into business for ourselves because we want to be great managers. Usually entrepreneurs go into business to get something done, and they realize they need others to help them do it.

Still, as Aliza says, if you are going to hire people, you must address how you will manage them:

"Being a boss, like it or not, is kind of like being a parent. If you can’t do your absolute best when managing other people, just don’t do it. Find another job. Put someone else in charge. Because bosses can have such deep impacts on the people in their employ, and no one should take that responsibility lightly."

In my current business I've had direct reports and then not. When I was managing I took my role very seriously, but I often felt like a bad mother being on the road and unable to work with my staff as directly as I'd like. I had a discussion with my partners about my best use, and realized that in order for me to fulfill my role in the company I would need to work cross functionally more, and manage less. I still like to catch up with those who were on my team; I feel a special connection. But I no longer oversee their work. Rather than a "mother", I'm an "older sister".

This has had a mixed effect: On the one hand, I'm freed up to manage my work. I don't have to worry about "checking in" with the team. On the other hand, as someone who craved mentoring in my career, I have less opportunity to directly affect their learning. They're doing more than fine without me, but there remains a hankering to be more impactful there. It's a feeling for me similar to being childless. I know it's a choice, not a condemnation, but I also ask myself, is this how it is because I would be a bad mother?

Are People Who Sleep Less More Successful?

Early in my working life in New York City I read a feature story, I think it was in the Times Business section, about the sleeping habits of top-performing media executives. The common thread among all of them: They slept no more than 5 hours a night. Most slept less. This tendency to not sleep was positioned in this article as a competitive edge, even a requirement to being successful.

I remember feeling discouraged. I had been slogging it out at magazines and was looking for some way to distinguish myself, but I wasn't an early riser. As a teenager I often slept until 10 or 11 in the morning. An early-bird class I had one semester nearly did me in. In college, I dropped the one class I had that began before 10.  I was fortunate to work in an industry where people ambled in between 9 and 10am. I never minded working late.

But the luminaries in this article--many of whom I forget now, interestingly, though I do recall book publisher Judith Regan--often worked long hours. A typical routine: Wake up at 4am; jump on the treadmill (these folks had the money and the space in their Manhattan apartments to have exercise equipment in their homes, something I aspired to have); shower and get dressed; read all of the dailies; and still manage to get into the office before everyone else.

For a while I tried to wake up early--around 6am--to fit in a workout before going to the office, but the effort was short-lived. My body much preferred working out in the evening and the scramble to and from the gym took too much time. I loved to read, but I could never get through all of my material on a subway ride. I figured I was just too inefficient and lazy.

Years later I still wonder how it's possible to hold to this kind of schedule. I work longer days now, but I can't function if I can't sleep at least 6 hours (insomnia notwithstanding). If I have to get up early for a meeting, or to catch a plane, I'll get up; I have to. But it's been only recently that I've accepted that all things being equal, I prefer to sleep in.

A job I want someday: Chief Culture Officer

The American Corporation sucks at culture, says Grant McCracken. His agent, a professional friend, sent me his book and asked me what I thought. Immediately upon reading McCracken's take on corporations' lack of cultural common sense I was convinced that the Chief Culture Officer (his term, and the name of his book) would be a position of the future.

McCracken backs real case studies into his assertion that the CCO is the missing component of the 21st Century Executive team. Some companies have had defacto CCO's that have made a difference, but these individuals took on more than their job descriptions. They made decisions based not on financial analysis, but on something not as easy to measure (and yet obvious to those who look for it): cultural trends. What would the companies be like if we institutionalized this job?

"Quaker Oats paid $1.7 billion for Snapple. It sold 3 years later for $300 million. Best Buy paid $700 million for Musicland, a retail music store, just as kids were embracing peer-to-peer file sharing. It had to give the store away two years later. Facebook decided to take ownership of the billions of photos its users had lodged there. Millions took umbrage, and the Facebook franchise was suddenly at risk.

In a turbulent marketplace, culture feels a little like the stormy North Sea. We never know what it’s going to throw at us. Culture matters. Get it wrong, and we miss opportunities..."

Among the opportunities McCracken cites as one missed is social media. Microsoft, which was always first to the table in tech, is scrambling to catch up.

This is in the opening passage of the Change This summary presentation for McCracken's book (read the PDF, but also read the book, which is chock full of examples that make you wonder why you hadn't thought of things his way before.) Sure, hindsight is 20/20, but you have to wonder what business blunders could have been avoided with a Chief Culture Officer, someone empowered to observe the cultural marketplace thoroughly enough to think beyond what makes business sense.

I think about my own company, and how lucky we were to be so fully ensconced in a movement (blogging, and more specifically women's blogging) that we could define a pulse as it was beating. The challenge now is maintaining such a close connection with our community as well as with the trends in marketing and social media, to not lose that intuitive knowledge. But it gets harder as you get bigger.

This year we hired a creative director, but I swear he's actually McCracken's CCO. Sure, we're not as big as Microsoft, but he's helped us define what we accidentally bottled when we built our event so that we can remain true to what we created. We run decisions by this definition--business partnerships, programming and editorial direction, relationships with sponsors, and our Website redesign, which will launch in a few weeks.

Some of McCracken's examples were stretches, or not as obvious as others. The reasons for failed product launches or businesses that lose relevance are nuanced and complicated . But on the whole I was in absolute agreement that many of these missteps can be tied to a failure to align culturally with the market.

My evolving definition of Working Smart

2009 was the year of getting organized. Sort of. I spent the latter half of my holiday vacation last year training myself to work differently. Don't get me wrong, I've managed to do things somewhat right over the past 16 years of my working life, but more than ever in my career I felt like I needed a working makeover--a new framework for productivity.

If you'd sat down with any of my past bosses (including myself, as I've had numerous stints of self-employment), all of them could say I was organized. They may not have praised my communication style, or how I presented, or my problem-solving skills, but dang-it I was ORGANIZED. But as an entrepreneur I've found that being organized is just the ticket to admission into the stadium. No one gets a front-row seat, or to even perform on-stage, unless she's strategically organized.

There's been a quantum shift in the type of work that I do. I've always had busy work, information gathering, creative work, and what I call "social time", when I must actually interface with people, whether on the phone or in-person, what Tony Bacigalupo refers to (quoting the uber-smart start-up supporter Paul Graham) as "Management Time". But in the past few years I've had much less control over when I can schedule these types of work. I attribute this shift to three circumstances:

Because I am a Bad Person: I'm blogging my holiday card

I was working on a typical post today when the mail arrived. Jesse plunked down a bunch of holiday cards.

"These are for you," he said.

That's actually not correct; they are for us, but Jess isn't really the greeting card type. When we received a card from my mother for our wedding anniversary in October, he read it, said with sincerity, "That's nice," then promptly put the card in the recycling bin. (Don't worry Ma, I fished it out.) Holiday cards are not keepsakes to him, whereas I save everything from cards to the "To:/From:" stickers I get on Christmas Gifts. It just seems like the least I could do for someone's kindness.

I grew up with a mother who finished everything "holiday"--the house decorations, the cookies, the cards--the weekend after Thanksgiving. She did not question whether she would send out holiday cards, like she did not question paying the mortgage, or making dinner. For years I was much the same way. I may have been busy at work; busy at home with myriad holiday parties and gifts to buy, but the holiday cards were signed, sealed, and delivered before December 15. Each one even had a custom, hand-written note.

I never sent photos, but I used to stage in my head my perfect photographed holiday card--Jesse standing sideways, his hand extended to my shoulder; I am standing sideways, my hand extending to the nonexistent shoulder of our cat Ginger. We're all in Shetland sweaters, even Ginger, and her paw is flattening some toy mouse in a Santa Hat. 

"We'd never get Ginger to sit long enough for that," Jesse said, when I shared with him my vision. He was never a holiday dreamer like me.

Perhaps it's Jesse's influence that creeps up on me now, as I flip through notes of Season's Greetings and pictures of adorable children, spouses and pets. People who put in the time to send us cards. I know it would make them happy to get a card from us. But until cards started coming in, I hadn't even thought to send any this year.

Perhaps it's a perfectionist thing: No major news to speak of, so why bother? Perhaps it's a time thing: I spend so much time working that holiday tasks I used to plan in advance like vacations are no longer appealing to me. Perhaps it's a phase. I certainly don't love my friends and family any less.

I've been putting a lot of emphasis on this new blog as of late, so perhaps I will provide a note here, for all of you:

The Accidental Entrepreneur

Though I’ve quit jobs and worked as an independent contractor before, I hadn’t aspired to be an entrepreneur until co-founding BlogHer. It just wasn’t me, being an entrepreneur, or so I thought. I was too much of a professional soloist, an INTJ if you will, to actually build a business from my singular efforts. I enjoyed creating, dreaming, planning, not number crunching or managing--activities that you’d associate with running a business.

What happened?

BlogHer was for me initially a response to something I wanted as a blogger that hadn’t been created. If it had already existed I would have joined it and tried to get a business development job. It wasn’t a business concept that I cooked up with my co-founders, thinking, “if we capitalize on this blogging thing …”  It was more a question I felt compelled to help answer: “If we kept connecting more women who loved to blog …” And this, I believe, made all the difference.

Some entrepreneurs are like carpenters; they like to build the foundation of a business—wire it for electricity, but don’t actually provide the power. They are more concerned with building four walls than what is discussed in them; whereas, the walls really don’t interest me. This is an important distinction, as entrepreneurs must essentially ask themselves, what is it you love about building a business, if we are to be successful. Is it the nuts and bolts of building it, or seeing the physical manifestation of your work, or is seeing the propagation of the ideas generated by it? Some entrepreneurs know they are carpenters and will only be happy building foundations. Once they’ve built a strong one they can move on to another business. I like to see the ideas catching on, and spreading those ideas. People like me need carpenters or we don’t get around to making our ideas stick. Alternatively, we are so driven by an idea we are willing to pick up the hammer until someone who knows what they are doing takes over.

I thought about this today because I was asked how I grew my business, and did I know I wanted to be an entrepreneur. There’s a tactical answer to the first question; I could walk you through the story of how I met my partners, and how we created a space for bloggers, and the decision we made to formalize our passion for the community by building a business around it. Though I think it’s not adequate to answer the question without addressing the accidentalness of it. Speaking  for myself only, if we had built the company from what was in my head at the time, in 2005, it never would have been realized, because I had yet to fully understand it what we were building. It was by chance that circumstances allowed me and my partners to be in a place where we could engage a community we loved and serve it while building the business case for it. I don’t know how you do that by design, honestly. That piece, I feel, is more luck than anything else.

Certainly passion is not the only requirement for being an entrepreneur: How many people attempt to build businesses that enable their passions and fail? But for Accidental Entrepreneurs like me it’s critical. We don’t like to build just to build if there are no ideas to perpetuate. And we can’t just make up these ideas. They have to grab us first, and cover our eyes while we are led down a path we wouldn’t choose to take otherwise.

Though I thought previous periods of “1099” work were entrepreneurial, they were really more about self-employment, freedom, and using my solo talents to further someone else’s vision and earn me something (money, visibility) in the process. But entrepreneurism is not about “freedom” in the way that people escaping corporate life envision it. It’s responsibility. It’s doing things you love, and things you don’t, for something you see as fundamental. If you have delusions of sitting in your kitchen and creating a business from all that you know in this instant, you are not an entrepreneur. You are self-employed.

The Entrepreneur's Mission: Infusing love into work

I took a walk with a friend today, a practicing physician with enough right brain influence that she often questions bigger-picture aspects of her profession that no longer make sense to her.

"Most of us go to Med School with the best of intentions--to heal people," she said. But an unfortunate and all-too-common outcome is the de-personalization of medical care. Sure, young doctors are trained to take emotion out of their approach so that they can treat their patients effectively, but this often means that there's little empathy and no ability to see beyond scientific rationales for causes behind symptoms.

This reminds me of my recent round of treament for the nagging jaw pain I have from grinding my teeth. I've been wearing a "deprogrammer" (aka: a retainer) for the past few weeks that supposedly makes it impossible for my back teeth to grind. And yet my teeth have figured out how to get around this contraption and grind anyway. My dentist's solution: Sand down the back teeth until they no longer touch. After two of these treatments and more discomfort I had to say, enough. Maybe I need to look at WHY I'm grinding my teeth all the time and be more cognizant of when I'm doing it so that I can train myself to stop it. I appreciate that the experts are trying to treat the problem painlessly and with little effort on my part, but in the end, I need to address the source of the problem some other way than tactically, more mindfully.

My friend agrees that this occurs often in her profession: There is often a pill or procedure meant to treat but not cure. Doctors don't see their patients holistically, but as a series of issues, and they are hired to solve just the one the patient can articulate. "We've been trained to take the love out of what we do," she said.

It's possible, I've concluded, for well-meaning, well-educated professionals to be smart and stupid all at the same time.

This discovery I made while walking through Golden Gate Park with my friend translates across countless industries and business in general. In the new media world that I live in the question of properly measuring the effectiveness of online advertising pervades all long-term discussions of its future. We have "smart" technology that can tell us when users are exposed to ads, when they click on them, and sometimes when they do something in reaction to these ads. Yet we can't properly measure the value of these clicks and of the places where these clicks come from that might have encouraged a purchase or a positive brand association. I love to point out that an incredibly influential blogger could host the most eye-opening discussion on her blog, generating priceless word of mouth, leading to sales, and yet this discussion could conceivably count as a mere page view using our current system. And even using the most premium rates available to compensate for placing ads on this site, the monetary value of this conversation is pennies. This may sound wonderful to the media buyer, but consider that this same buyer could be spending so much more--thousands of dollars--to advertise on sites that in effect game the system by being rich with page views but devoid of authentic, actionable content. This is why the industry is bent on establishing metrics that better indicate bloggers' influence and the quality of engagement on sites. They are trying to measure love.

Likewise, back to health care. Doctors are increasingly paid for the drugs they administer, expensive procedures they may or may not do themselves, and are versed in "moving patients" as quickly as possible. The current system does not compensate them for sitting with patients who have just been told they have cancer, for telling patients that they do not recommend pills but rather self-esteem to help them with their hypertension. Everyone must be treated clinically (without love) making it too difficult to adequately diagnose those who truly need a medical approach. Instead they insist on grinding our teeth to the nubbins (sorry, I'm still bitter).

My friend was passionate about her desire to apply love to medicine and was stumped on where to begin. I have no doubt that she will figure that out, and I won't be surprised that in the process she builds a new business. That's what entrepreneurs do: discover how to infuse love into what we do. And that's our dilemma: once we discover how to infuse love into what we do, how do we continue to do that, as we take on administrative issues, new people that must internalize the mission, and new desires that request our precious time?

Infusing love into our work, this is the luxury we ultimately have over our corporate counterparts, and it's the first thing we stand to lose when we become successful at what we do.