From Here to Autonomy

Real Advice on Public Speaking

I got a kick out of reading Tim Ferriss's post on how he prepares for a public speaking gig. Ironically Ferriss, author of The 4-Hour Workweek, could take up an entire four-hour work week with just his recommended prep alone.

Still, I appreciated his no-nonsense approach to getting things done, and in this post his candid admission, despite much acclaim and speaking opportunities, of not being a natural public speaker. I can totally relate. People who know me probably think that's disingenuous coming from me, an extrovert, a Gemini, a communicator. But it's true. Sure I love to talk, but talk in an organized, engaging manner? That takes practice.

Five years ago, if someone asked me if I had a strategy for public speaking, I would have said something about winging it and going with the flow. I am oddly more comfortable with being asked to share something off the top of my head than a practiced response with chunks of sound bites. Unfortunately for me these days that ain't realistic. So I did what I had to, built a speaking prep routine.

Over the past few years I've established best practices that work for me, and maybe for you:

Encounters: The Exit Strategist

Ten years ago I moved to San Francisco from New York. I had been bitten by the start-up bug, having worked for a hybrid start-up (one that had the chaotic feel of a start-up but had already gone public) and was intrigued by the notion of starting something from scratch. I finally got my chance, though it meant moving across the country.

A few weeks into the job I was asked to meet with potential editorial partners. Co-marketing relationships, I was to learn, were a dime a dozen for Web start-ups in the 90s. Non-exclusive, often cashless transactions where you linked back to a partner's Website and vice versa in an attempt to expand your Web traffic. These kinds of deals still exist, but in general I think we as new media professionals have become a lot smarter about when these partnerships actually make sense. I think about some of the deals I did back in '00 and cringe (Online therapy? Really?), but I digress.

What occurs to me now is that these deals didn't need to be particularly sustainable--they just needed to provide a quick burst of traffic, or even just the promise of traffic. The goal was to appear to be growing so that when the time came to exit, the optics were there.

The fellow I met was roughly my age--27 or 28 years old. He'd started his career in San Francisco and seemed much more comfortable with the start-up ethos than I.

"Is it me, or do people seem not to care as much about work around here?" I said, half-joking. I had a small staff of writers that ambled in and out as convenient, and rather than see this as a management issue on my part, I opted to demonize these people for not having enough drive. I don't think this guy understood.

"We work around the clock," he said. I suppose that was true of many of my co-workers as well, despite my complaints. Staff might have come into work at 10 or 11 in the morning, but they often stayed on call through the night. They just didn't have the intensity I would have preferred. It seemed that they could be doing what they did for any company; ours was just the one that had hired them first. I was used to making my company my cause d'etre.

"It's fine for now," he continued. "Once we sell I'll just chill out."

Now here's the part of this story that people don't believe, despite the fact that I knowingly moved across the country to work for a new media start-up, despite the fact that I had a stock option package, I really didn't understand exit strategy. The thought of working your ass off to someday stop working sounded so foreign, even ludicrous, to me that I wasn't sure I understood.

"What do you mean, 'if you sell?'" I asked him. "Is that why you are doing all of this work? To stop working at your company?"

"Of course," he said.

"But what will you DO after that?" I asked.

"If I play my cards right, I'll never work again," he said. A few things went through my head at this point: Fear that perhaps in my haste to secure this job I hadn't paid enough attention to the stock option portion of my compensation. And I felt a more enveloping fear: What if it should ever come to pass that I don't need to work for a paycheck? I had always been validated by work; I would just keep working, would have been my default answer. But this guy felt differently. Who's the chump? Him or me?

"But seriously," I asked again, "what would you DO?"

Now he looked at me like I was nuts. "I'd sleep in, go to the beach, surf more. I don't know; I would just figure it out."

It didn't seem possible to me that he wouldn't want to continue to build on his success at his current company, or maybe even another one. The thought of just stopping didn't make sense to me. Why would someone stop working? I thought of what I would do if I had the option of not working. All of my aspirations were related to work; I couldn't think of anything. I might travel, but then I would have stopped after a few weeks and started working again. Work was my only compass.

This is a rather dramatic example, but I think this encounter gave me an early glimpse into where I needed to be aspirationally before becoming an entrepreneur. We represented two ends of a spectrum of motivation; each on its own could be disastrous to entrepreneurs. Some of us may be more lifestyle-motivated, and some of us more achievement-oriented, but survival as an entrepreneur must borrow from both sides: A life you want, plus a desire to make things happen.

PowerPoint Confessions #1: A Week in the Life of an Entrepreneur

PowerPoint Confessions, Vol 1: A Week in an Entrepreneur's Life

View more documents from JoryDJ.

UPDATE: Major disappointment with SlideShare. All the notations I've put in the deck, which are meant to give you some insights into how I plan my week, are not viewable. Will see if I can get some help from SS, or this first installment of PowerPoint Confessions is a bit of a fail.

Back in November I was in DC, visiting New Media Strategies and chatting with their Director of Engagement Leslie Bradshaw, who turned me onto a cool idea--something she had been doing on her own blog--PowerPoint posts.

I have a love-hate relationship with PowerPoint. On the one hand, I hate when people over-rely on it to relay a message. However I love it as a stimulator of thought. Visuals can often make a point more powerfully than words. For instance: I can tell advertisers about the power of the BlogHer community, or I can show them pictures of women bonding at the conference, their Tweets and comments upon engaging with a brand, and a chart of the increase in brand awareness that ensued. These are more powerful than just taking my word for it.

I speak a lot to marketers, media professionals, and reporters who want to better grok the social media space. At some point this year it occurred to me that the creativity I once reserved for my previous blog Pause was now going into PowerPoint slides describing trends on the Internet. What if I brought these two worlds together, and created visual posts detailing anything from media analysis to the mundanities of the workday?

I was sold on the PowerPoint Concept; I just needed topics. Tresha gave me one in my comments section:

a simple request: a blogpost that offers your schedule. there's no typical schedule but what's a day in the life of Jory look like 5 am - 1 am? 4am to midnight. or 11pm? what? how you a lot time each hour? my why behind that? I think it's just a supportive hug to one another. We are all getting much done and have different demands. 

Initially I thought, who really cares about when I eat breakfast, or if I even bother to eat breakfast? But then I thought of what I tend to ask entrepreneurs I meet: Not "How did you grow your business?" but "What time do you wake up?" "When do you go to bed?" "Do you make dinner?" "Who tucks the kids in?" To me, addressing the everyday and learning how to make it work is the key to entrepreneurial longevity.

So here, my first installment in PowerPoint Confessions, with a nod to both Tresha and Leslie, a week in my life--the first installment of PowerPoint Confessions. It truly is confessional, because I offer up the often nonsensical way I plan things in Outlook (nonsensical to others, not to me). No laughing, please.

Overcoming the need to be ubiquitous

I tend to be attracted to other entrepreneurs; whether they're running their own ice cream shop or running Google, I love to hear their stories. I just met a former entertainment executive, now business soloist, who reached out after reading the blog. Her energy I found exhilarating and her openness to sharing her experiences drew me in.

There are some dead-giveaway characteristics of people who have taken the leap into either working for themselves or creating a soloist venture; in no particular order:

• You crackle; the mouth cannot keep up with the constant flow of possibilities. Everything reminds you of a potential business opportunity, or someone you should introduce to a contact. You are so immediately connected to your expertise, even as you are developing parts of it that you can postulate and strategize on the spot. The biggest concern is not whether it can be done, but if you've captured all that you've just conjured. You've never had so much to say.

• You sound like Alanis Morissette (sing with me, or just play the harmonica): You're broke but you're busy, you're smart but a newbie, slayed corporate dragons but you need toner, yeahahhh! You speak in seeming contradictions; your reality, to non-entrepreneurs, seems a little nuts. You often hear comments from these people after sharing aspects of your day, "Really? Are you OK?" or "You can always get a job." What they don't get is that while you've never been more scared you've never lived so meaningfully.

• You're multilingual: When you speak to a doctor, he'll share information through a medical prism. Likewise, when people asked you questions in the past, you spoke through the prism of your industry or department (publishing, marketing, online sales, manufacturing). Now you speak through many prisms because you've been opened to them. It's disorienting (as my new friend said at one point: "I feel like I've become stupid.") but it's actually a mind-expansion, not a contraction, that you are experiencing. In this one conversation my friend invoked the music industry, social media community, and a psychic as sources of inspiration and learning.

I resonated with all of her struggles and triumphs: the initial plummet of income coupled with the most personal satisfaction she's experienced in her career; the contradiction of being in charge of her life but completely overwhelmed by things that need to get done. The fear of failure despite the constant buzz of opportunity. 

"I just don't know where the time goes," she told me. "I'll hop on Twitter to check something, and end up on it for two hours. It'll be movie night and I'll end up saying (to my husband) bring soup to me here."

Now THAT I can relate to--the sense of discovery that occurs with entrepreneurism, soloing, this journey. Pieces of information become keys to doors that have to be opened, not tomorrow, but today. You learn of meet-ups, live events, bloggers, trends, and need to pursue these keys, with no guarantee of what they will unlock.

"I would go to the opening of a condom now," my friend said, half-joking.

I have occasional conversations with my partners about events, projects, things we did early on, things we can no longer do, because we need to be focused, and because we'd been down similar roads enough times to know that while no road is worthless, some are better bets than others.

I have no pre-emptive strategy for how not to waste your time, other than to realize that there is no such thing as wasting time at first. It all matters. What I would offer up is to notice when things start to feel like a waste of time, when you have a suspicion that you will feel depleted after attending that monthly mixer--again. When you can't seem to be able to schedule a call with someone who has stopped adding value to your day personally or professionally, but with whom you told yourself way back when you'd stay in touch. When you stop feeling like you are learning from a source of previous inspiration and start to resent it.

Because when uncertainty becomes more an expected friend than something to overcome, and paying your mortgage is no longer the most immediate goal, time becomes increasingly more valuable. You become more protective of it and are less willing to just see what happens by spending it with abandon.

There are times when I yearn for the desire I once had to be everywhere at once. I joke now that I'm getting old. What I really know, though, is that I'm learning to be an entrepreneur.

Creatvity On-Demand: Is this possible?

In my efforts to get more creativity out of my work and not wait until the weekend for divine inspiration, I've been capturing ideas for the blog and interesting pieces to read as I find them and store them for when I can fully digest and interpret them later.

This is meant to save me from what often happens when I am inspired at an inopportune time and run down a rabbit hole with an idea, blowing off work I need to do and disorienting myself for the remainder of the day.

So how is it going? OK. Not great. Just OK. I've noticed that when I go back to these pieces that inspired me, I have lost the thread of thought on which I wanted to elaborate or the piece just doesn't interest me like it did. Sometimes I'll scribble some thoughts down to help trigger me later. For instance, in my inspiration file I see terms that in some cases only I understand: "MPT, Chris Rock, legacy building, Tweet--sleep is for the week." I wish myself luck piecing it together. (By the way, these terms will be incorporated into a post coming soon; they actually mean something to me.)

Despite the fact that creative geniuses like Twyla Tharp are successful with programming periods of creativity into their day, and happiness is strongly linked to having outlets for creativity (this was cemented for me when I took this quiz),  I find that managing the flow of creativity is often pretty difficult. It's tough to be creative on demand.

This year I hosted a sponsored video show called TheJuice, in which I got to speak to experts about all aspects of life balance. My partners thought it would be right up my alley, possibly because of my obsession with studying, if not achieving, balance. One of the experts, Jennifer Lee, of Artizen Coaching is an expert in inspiring creativity. She works with entrepreneurs who rely heavily on it to do their jobs. She provided some great insights for bloggers, who have to pull rabbits out of their hats regularly. Still, I wonder, even after blogging all this time, how do some people have the ability to always be in the flow of creation?

A friend of mine, a documentary filmmaker, told me once that creativity is like running. The first few times you go out, you feel awful, like you are out of shape and incapable of enjoying the process, but through ongoing practice you eventually get your footing and even start thriving on running. It worked for me that way when I started blogging back in '04--I stumbled to find concepts, and eventually had to tear myself away from my laptop I was so infused with ideas and conversations in my head. I also had the luxury of hours to spend on my writing, during which I could fidget, fart, check email, and wait for words to come to me naturally.

Few entrepreneurs have this luxury, even those who write books as a big part of their living. I'm always amazed by pals who are writing books and running a business. How do you segment your day to get the most out of both endeavors?

I've had to settle for a hybrid form of creativity--proposals and presentations. This requires summoning ideas that meet a set of criteria, as client needs are not always what I'm moved to impart, but I can choose how to impart them. I never thought of this sort of thing as creative until I witnessed how others did them poorly. You know who I'm talking about, the person who reads off power point bullets pulled from the sales deck, or proposals that are so disjointed you wonder how a client could put the pieces together? It's a new pride that I have in my creative abilities, even if I'm not writing the great American novel that I am helping people connect the dots. I'll take this form of creativity ... for now.

Other mini refuge periods: Flights, and a blogreading period I've inserted into my mornings. Yes folks, I'm getting up earlier these days. Something I never thought possible. I'm still training my body to fall asleep earlier so I'm not exactly bursting with energy, but I'm more satisfied with my day by carving out this time.

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.

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: