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.

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.