Forcing Function: 90 Days to a Decision

As mentioned previously, it has taken a long time to settle on my next full-time role. Following a period of professional experimentation that turned into full-blown commitment phobia, I have finally given myself a firm deadline: 90 days.

While these past nearly four (!) years since I left my last CEO position have brought the kind of freedom I once dreamed about, I’ve also learned that the risk of paralysis between projects is real and dangerous. With no forcing function to choose a next step, I was guilty of over-analyzing all options and comparing each of them to previous gigs.

No longer the broke, hungry young entrepreneur, I now live in beautiful Marin county, surrounded by soccer games and middle-aged triathletes. I’ve had a whole football team of people to support the navel-gazing lifestyle: therapist, trainer, yoga instructor, life coach, chef (trust me, it goes on in even more embarrassing directions). I had become one of the lotus-eaters from Homer’s Odyssey.

Now whosoever of them did eat the honey-sweet fruit of the lotus, had no more wish to bring tidings nor to come back, but there he chose to abide with the lotus-eating men, ever feeding on the lotus and forgetful of his homeward way.

While some of my guy friends tell me I’m suffering from a severe case of “affluenza,” I’d argue that my problem is not about money, but too much comfort. I had the same issue when I had a “comfortable” job early in my career. The underlying question is: how do you break out of crippling patterns of ease and security. Where does the catalyst come from? I could go on forever in the beautiful ether with no grounding, but would end up medicated in one way or another, possibly becoming the Hunter S. Thompson of greater Marin.

I thought I had checked the box on success and was on to other bucket list items (“Invent next turducken” still not complete), but slowly became miserable. I was at home more often, but less happy when I was there. Outside of family, purpose was fuzzy (no “homeward way”) and I was trapped in the American Dream, filling in life’s gaps with empty-calorie activities.

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And I wasn’t paying enough attention to life’s bank statement to see the shrinking balance. As Seneca said:

“It is not that we have so little time but that we lose so much. … The life we receive is not short but we make it so; we are not ill provided but use what we have wastefully.”

Pity is the last thing I expect. I’m not that self-absorbed. Instead, I’m hoping you’ll help hold me accountable to my time frame and my goals.

I’ve only been “on the clock” for a week, but so far, so good. (“Bought whiteboard: check, Publish blog: check, Have second thoughts about arbitrary timeline idea: check.”)

Reservations aside, I’m awake, purposeful and have numerous interesting conversations going. Instead of considering all options, I am forcing myself to whittle down the list aggressively – make choices, stick with them and figure out what matters most.

I want to get back at it. I miss the fight, the blood and sweat. Climbing a mountain with a tribe. The burning desire to build something is still in me at 41, and I can’t meditate my way past it. And frankly, I don’t want to.

Wine, Women and Why We (Should) Start Companies

It’s been 3 years, 8 months and 3 days since I stepped down as CEO of Jive to decompress, fix the mess at home and figure out my next move. I’ve kept myself respectably “40 hours” busy on many projects, but have had an annoyingly tough time deciding on my next full-time pursuit. In countless conversations about potential opportunities, most of the ideas have been as exciting to me as working on my taxes while standing in line at the DMV.

I keep getting wrapped around the axle on my real desire for doing it: is that really how I want to spend my life?

During my time at Jive, I spent more time considering which brand of conditioner to use than delving into my deeper motivations and desires. Like a lot of first-timers, I wanted to “build something great,” “change the world” and “lead an awesome team,” but the reality was that it was exciting, new and (at least half the time) working. That was more than enough.

And let’s be honest: as much as I talked about how money wasn’t the motivation, it certainly wasn’t absent from the equation. My Mom recently sent me a story I wrote when I was nine in which the main plot was how I was paid $20 million a week to live on Mars for a month. Not much happened other than me living on the planet and then getting paid. Clearly money was an early obsession of mine, along with including my name as many times as possible (below). But I knew intellectually it shouldn’t be.

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Cover to My Mars Story

For something that takes up half to two-thirds of our waking lives, shouldn’t we be crystal clear about why we’re doing it? And more importantly, why should we be doing it?

Enter an unexpected source of guidance: Plato. (It should be noted that I got a C- in my freshman philosophy class. But my Dad is a retired philosophy professor who spent much of my childhood using Hegel and Kant to help me think through issues like football and college, so something stuck.)

Around 385 B.C., Plato created what many call his masterwork: The Symposium. A “symposium” was a wine-fueled party where participants each give speeches on the same topic. At the end of the evening, one less slurry and more brilliant speaker is declared the winner (it pays to get the early speaking slot).

Plato was not at this particular party, which took place in Athens many years prior, but that didn’t stop him from presenting the arguments in dialogue form to make his case on the ultimate purpose of desire. Each historic figure presents appealing arguments and adds to the book’s overall theory–even the guy who can’t stop hiccupping (really).

At the end of the evening, Socrates emerges as the winner. But in his speech, Socrates actually recounts a conversation with a priestess named Diotima, who gave him the essence of his argument. So while women aren’t even invited to the event, it’s still a woman who manages to make the most thoughtful case on the purpose of desire.

Diotima tells Socrates how the God named Eros (Desire) is the son of Resource and Poverty. This is a God who is always hungry but also tough and resourceful in making things happen; he’s always seeking, never truly finding. (Sound familiar?)

Diotima’s main point (spoiler alert) is that the purpose of desire, and what all humans seek at our deepest level, is to “be impregnated by ideas and give birth out of the pregnancy of the soul.” In other words, the same drive behind physical love (procreation and extension of the species, which are the closest we get to immortality) is even more powerful when applied to our intellectual lives.

Yes, this is a bizarre metaphor to bring up in a business blog, but stick with me. The idea here is that the purpose of our human endeavors should be to take in (be impregnated by) outside ideas, and then to give something beautiful back to the world through our own unique lens. To live a balanced intellectual life, we need to be both receivers and senders of ideas.

Unfortunately most entrepreneurs are much better at sending, not receiving. We want to be the smartest in the room. We have trouble listening. Left unchecked, this tendency will lead to an innovation-less company taking the path of least resistance. These people may make money, if that’s the goal, but they do not represent an authentic or original voice in the world. As the philosopher said, “Where is the Love?”

Steve Jobs (un-original alert) famously brought together technology and the humanities. He was remarkably open to being impregnated by outside ideas like calligraphy and furniture design, and using them to create beautiful products. He didn’t make “sugared water”.

I’m not proposing to be Steve Jobs (reality alert). But I found Plato’s thesis to be the “first ice cold beer on a hot day” of my confused life planning. If you step back and consider the purpose of entrepreneurial desire as being impregnated by ideas and giving birth to something good and beautiful out of your (and your colleagues’/company’s collective) soul, then it might open you up to a more satisfying experience and actually make the world a bit more interesting.

Re-reading this section of Plato empowered me to stop striving for perfection, but find inspiration instead from a broad range of perspectives, surround myself with like-minded people and give birth to new ideas (big, small and everything in between).

And it made me realize that hunger / poverty comes from many places. Being open to inspiration from unexpected sources leads to discovering hungers I didn’t know existed.

Think about all that the next time you refer to your company as your “baby.”

Where have you found motivation and inspiration for your biggest entrepreneurial moves? Do you feel like you have a good grip on why you’re doing what you do?

Would love to hear. Keep the great comments coming here, and through the social links below – thanks!