From Here to Autonomy

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.

5 bad reasons to become an entrepreneur

1. Because you really need a job: Even as the economy is showing signs of life, the job market still sucks. I get it. I've been one of those people who, months into a downturn, thought "Hmmm, what if I started my own business?" But I should have looked a little deeper. Back in 2002 I teamed up with a woman who had run her own business for years to start a marketing consultancy for professional gurus. I figured, I loved to be around smart people, had a Rolodex of contacts and strong background in media, and I had a partner who knew the ins and outs of running a small business, so why not? But what I really wanted was work on my own terms.

We needed capital to pull together marketing materials--something that I really didn't have. We needed to invest in a designer, an accountant, and the legal procedures to properly incorporate our business--expenses that felt like amputations. All I wanted to do was the business development and the client work, none of this business-planning stuff. After six months I had a heart to heart with my partner and realized: I don't want to start a business, I want to be hired to do work I'm good at. Big difference.

Sure there are businesses that have sprung from necessity, but unemployment is one of the worst reasons to become an entrepreneur. You are spending your resources at a time when you need them the most. The best time to consider entrepreneurship is when you are employed and drawn to doing something else. Then you can truly answer the question of whether you are committed enough to provide steep outlays of time and money to give your business the care it needs.

There's nothing wrong with wanting to take the bull by the horns when you are unemployed and drumming up your own work, but determine what it is you want: a paycheck, or your own business?

2. Because you want to work less. More flexible work schedule? Check. Fewer hours? Not exactly. Despite what I've read from people who have whittled down their workweeks to four hours, I still think that people who start businesses for a more leisurely lifestyle are not crazy, just delusional.

Some people eventually achieve a momentum and can allow others to do much of the heavy lifting, but by no means does this happen without a whole lot of elbow grease.

When we first formalized our business, my partners and I enjoyed the freedom of creating our own hours, but that didn't mean we could reduce them. And frankly, the more established our business became, the harder it became to do things on our personal schedules. Clients and investors could not be slotted in when it was convenient for all of us. Opportunities happen when they happen. Later when we received venture capital and hired staff to help us, we still had a lot of work to do--just a different scope of it. As we built a workplace that allowed for such things as varying commute times and child pick-ups, we still needed to adhere to the same general hours our employees did so that we could be available when they needed us, and then for everything else that came up.

The entrepreneur's challenge is not "How can I make money doing not very much?" It's "How do I fit the rest of life into my day?"

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.

The Emerging Entrepreneur's Dilemma: When do I close the door?

Ten years ago I suffered a romantic setback; that's what I call it now. Back then it was more like a breakup. I was old enough not to feel particularly nostalgic about the person I was breaking up with--it wasn't a fit. What was more disturbing to me was the pattern of unavailable types I was attracting. Despite my seeming efforts to find someone "right" for me. I was pursuing the wrong people. Or allowing the wrong people to pursue me.

Fortunately for me I had a cadre of pals in the personal development space whom I could take out for coffee and conversation. One of them, a life coach, always insisted to me that the sooner I could move on from these wrong relationships the quicker I'd get to the right one. You know the saying: By closing a door, you open a new one.

Initially this was counterintuitive to me. On the career side I had learned that you never quit a job without having another one lined up. Of course, as life complicates, this becomes far more difficult to do. If you don't actually quit and move on in your mind, you cannot fully embrace the new, unless you expect to repeat a pattern of settling for less.

During an especially disappointing relationship I recall laying in bed, thinking to myself: "I'm sick and tired of this, I'm done," and went to sleep. I broke off the relationship the next morning, with none of the drama or emotional afterbirth usually associated with my messier breaks. And while I was scared--even a bad relationship can provide a sense of security--I felt hopeful, like I was ready to have the right thing come to me. It did. And it felt different, uncertain and unfamiliar. But I was so thoroughly sick enough of the wrong thing that I was willing to stick it out and see where it took me.

I started to get good at closing doors quicker, in all aspects of my life. I had experienced a number of career breakups--most of them not that memorable; I was unhappy at the job, interviewed for other jobs during lunch, and then moved on when I got the offer onto something different but eventually equally dissatisfying. I had some experiences with what I thought was "The One," the job that would give my life purpose and direction. These usually involved breaking with the corporate world for a spell, until the uncertainty and loneliness got to me so much I clawed my way back to a matching 401(k).

Eventually, after a few cycles, I quit for good, with no bad feelings for my boss, no gig lined up, only a willingness to embrace what came, and it worked. It was life altering and life defining. Every day I acted with intention and embraced what came to me. Everything was a sign, something to be explored, until I was far enough on my path to determine when it wasn't.

Still I think back and wonder, if I had known how hard it would be, how many times I would question whether I needed to do something "responsible," would I have done it? I remind myself that's a bad question, like asking yourself that if you had known how uncomfortable being born would be, would you have done it? For entrepreneurs, entering self-employment is an inevitability.

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.

A Travel Resolution: Spending more quality time on the road

I've been thinking a lot about my business travel rituals while I've spent the last week at home on vacation. I hadn't realized I had some, but over the past few years it's become inevitable.

Before we had secured venture funding, travel was done on the founders' dime. As we started to build revenue we had a bit more budget to work with, but mostly it meant finding the cheapest air and hotel rates, hoping to get some freebies from miles, and researching how to get to and from airports using subsidized transportation.

With our office manager's help, I still try to find decent rates where I go, but I realized how much time and precious energy was lost trying to skimp on basic travel expenses. Now I take cabs or order car services and avoid redeyes. It just makes more sense to have more time to work, not commute, and to be effective at meetings, not just show up for them.

I've also made more emotional expenditures. I go to New York often and stay with my sister, which in addition to saving the company from astronomical room rates also grounds me. If I'm not working late I'll read to the kids before bed, or eat with my sister and watch a TV show. When I'm in Chicago I stay with my mother and like to go to dinner. I may have to get back on email afterward, but at least we can catch up over a meal. 

When I'm not with family and on the road I try (try, being the operative word here) to get in some TV or reading at night. I try to work out and read the newspaper in the morning.

I do what I can, but I think there's more to be done. Perhaps I have to think about spending less time with my "other family."

It's a joke, even if twisted, my husband's reference to my "other family". He uses this term to make light of my incessant business trips. When I leave on one he'll often say, "Off to see your other family?" When I call him from the road and tell him I have to make our call short to get some shuteye, he'll say, "Yep, gotta spend time with your other family." He says it lightheartedly, but I know that there's a tinge of regret in there. I know he misses me.

Sometimes I have fun with this "other family". I'll call him, after coming home late from a business dinner on the road and tell him I was out with my other family and calling to check in. Rarely do our conversations last very long, and I attribute this to having more to do before bed or sheer exhaustion. He knows it's not personal--we have better conversations in person than over the phone. But when you spend a lot of time away that's a lot of small talk.

I'm curious to hear about others' travel rituals. How do you stay connected when you are with your other family?

Who Can Live on Airplane Food Alone? When Life is Up in the Air

Up in the Air, starring George Clooney, as I was sure to relate to the lead character's obsession with airline loyalty program status (see some examples of said obsession on my blog Pause). I did chuckle at the parts where Clooney is comparing loyalty program perks with another road warrior/paramour. I thought to myself, Lord that's how I sound sometimes. Though I have much less of a need to reach the 10 Million Mile Club. That sort of honor would make me feel like I really don't have a life, and at some point in my travels I realized perks were not badges of honor, but simply ways of enjoying the less-than-ideal situation of spending time away from home.

There were parts that unexpectedly resonated with me. The Northern Wisconsin restaurant where Clooney meets his sisters for a rehearsal dinner before his younger sister's wedding was eerily similar to one I went to last year for my cousin's wedding in Wisconsin. The tech conference Clooney crashes with a colleague and a woman who becomes his no-strings attached hookup could be Ad:Tech (loved the inclusion of Young MC here as the nostalgia-inducing act). I've also honed my security screening routine to an efficiency that's less balletic than the film's version, but not dissimilar.

(Spoiler alert: if you are more interested in underlying messages than plot) Clooney's character not only has client engagements while on the road--he is a gifted speaker who talks about how to live "without baggage". His topic justifies the way he lives. His physical home, where he spends only a sliver of his time, looks different than you would imagine a businessman to have: It's spare, almost dorm-room-like in soulessness. It reminded me of an extended stay suite, only more empty. Clearly this character has not invested in, nor cared to have, a personal life. A series of random events makes him aware of this imbalance, and he feels the pain of being disconnected.

I am lucky to have a family and network of friends who stay in my life, but certainly, while single, I had no desire for connection. Perhaps I was a late bloomer; I had different priorities from others my age, who seemed to live for their weekends, were saving up for houses, and wanted life partners. I just wanted a promotion. My work was my connection, and I was good at it, while being less good at relationships outside of work. There were always people around, I was hardly lonely. I assumed that being good at work would address all of the other areas that were being neglected--in due time. This doesn't happen. It happens when you decide it will.

I see many real-life foils to Clooney's character who make work and life work, perhaps not with the balletic efficiency Clooney's character has while packing his bag and embarking on the next business trip, but with far less regret.

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