When do you know? I mean, really know?

Slumped into my couch, pale from a lack of sleep, nose red from the cold he can’t shake, the CEO shook off my suggestion about this being the time to hire an assistant.

“I know, I know,” I said, “you’re a cheap bastard,” and we both laughed.

“It’s not that,” he said after a pause, “it’s just that—well I know we should be hiring for what the company is going to look like in six months but what if it turns out I have to fire them down the line. What if I’m ahead of the game?”

I told him: “You’re at that point when, if you don’t hire enough firefighters, you’ll never get out of firefighting mode.”

“This little start-up of yours,” I continued, “is about to become a company.”

And he looked at me with a mix of relief and sheer terror—and just a touch of nausea.

Later that week, I got an email from another client returning from a board meeting.

“We’re not dead,” he said in a slight nod to Monty Python. They’d given him one more quarter before they’ll decide if they’ll fund that last half million everyone thinks will take the company to break-even. Of course the problem is this is the third “half-million to break even” the company has needed in the last year.

Still another client calls. He’s preternaturally calm. Spooky, even.

“Well my man…we’re burning a quarter million a month and I’ve got a million in the bank. If we don’t close this deal [a deal that will net the company a few million as the result of a sale of an asset], then it’s all over.”

But then he says the really spooky thing; he says: “I think.”

When do you know it’s time? When do you know it’s really time to start the business, shut the business, expand the business, invest in the business, quit your job, end the job search and take the offer on the table, leave your spouse, marry your girl/boyfriend, move to Australia, come home from Australia? When do you know?

“A warrior accepts,” writes Pema Chodron in Comfortable with Uncertainty, “that we can never know what will happen to us next. We can try to control the uncontrollable by looking for security and predictability, always hoping to be comfortable and safe. But the truth is that we can never avoid uncertainty. This not-knowing is part of the adventure. It’s also what makes us afraid.”

I think the only answer to the plaintive poignant question of “When do you know?” is embedded in the bit of Buddhist wisdom: You can’t know–not really, anyway.

Maybe the hardest part of leadership—be it leading a company, a family, a relationship or simply your own life—is that often times you don’t know and you still have to act. Leadership in some ways is built on learning to be comfortable with not knowing, with imperfect knowledge, with the inherent uncertainty of it all.

My mother always said he had massive hair on his shoulders from carrying blocks of ice up the stoops of Brooklyn. As I grew up, I began to doubt that ice causes hair to grow, but I never doubted my grandfather’s strength.

We lived in the ground floor apartment of a three-story limestone (a cheaper version of a brownstone) on East 26^th between Avenue D and Clarendon Road, in Flatbush, in Brooklyn. My grandfather owned the building (as he did several others around the neighborhood).

Dominic (no “k”) Guido, I believed, could do anything. I knew it ‘cause of the rats.

One day, as I was passing through the areaway under the stoop and getting my purple Stingray bike out of the shed to go for a ride, I saw this nose poking through a wall. “Rat!” I screamed and ran out. An hour later, Grandpa showed up. He stuffed the hole with steel wool and broken glass and patched the hole with cement. Rat problem solved. He could do anything.

He also remains to this day my ideal entrepreneur.

He’d left school after the sixth grade. He’d come to America from Palo del Colle in Bari and starting with nothing but a pushcart, he built a mini-empire of two or three trucks (and three or four buildings) selling ice in the summer and coal in the winter (and homemade illegal wine all year long during Prohibition).

He’d made enough money to raise seven kids (some of whom even went to college). And, most important, at the end of the day he always had more money than he had at the start.

I’ve met thousands of entrepreneurs over the years. I get the mindset. I’ve been there, done that; I’ve struggled, celebrated, laughed, and mourned with dozens of them. And when I was an investor, the ones who reminded me the most of my grandfather were the ones I was quickest to fund.

I thought of him, with his gnarled hands, suspenders, perpetually rough cheeks the other day when I was meeting with D.

“At least,” started my client, “at least I can say I raised a lot of money.”

Really? I thought. What would Dominic say?

I get that fund-raising is hard. It’s probably the most frequent topic in my sessions with CEOs. I also remember vividly sitting on a board of a company as it struggled to raise its next round.

But I also remember another client—T. T’s worked at his business for nearly four years.  He’s built his business selling his software product one customer at a time.  This year, he’ll clear $300,000 in revenue and be able to pay himself livable if not great wage as well as the salaries of a developer, a business/sales jack-of-all-trades, and a representative in the UK.

And he has no debt. And he owns 100% of the equity in his company.

Clearly not all companies can be built this way. And clearly, too, T’s business might be able to accelerate rapidly if it had a decent infusion of cash—if for nothing else than to improve his SEO ranking.

Nevertheless, there’s something sweetly endearing about the hand-built, boot-strapped business…something that Dominic would appreciate.

Grandpa’s Rules of Business

1)   Debt? What’s Debt?

2)   Always have a secondary income plan. Sell ice but don’t be afraid to sell a little wine as well.

3)   A nap in the middle of the day is a good thing. A nap at the movies in the middle of the day is a very good thing

4)   Figs are best when eaten right from the tree

5)   Chicks dig Old Spice

6)   Don’t take off your long underwear until the spring.

7)   When in doubt, go ahead and buy the extra truck

8)   Find out what your customer needs and sell it to them

9)    Work harder than your competition

10)   Laugh

11)   Eat lemon drops

12)   Families are good; big families are better

13)   Always remember who you are and where you came from

14)   Always have more money at the end of the day than at the beginning.

I think I’ve finally adjusted to the fact that I’m never going to be a war correspondent. I’m never going to live out of a backpack, drop everything and travel around the world to be where the action is.

I’ve also finally internalized that I’m also never going to spend a few months floating on a river with my best friend Jim. I’m never going to light out for the territories…at least not the way I’d expected. Huck’s learned to close the door softly.

Men at Forty

by Donald Justice

Men at forty

Learn to close softly

The doors to rooms they will not be   

Coming back to.

At rest on a stair landing,

They feel it moving

Beneath them now like the deck of a ship,   

Though the swell is gentle.

And deep in mirrors

They rediscover

The face of the boy as he practices tying   

His father’s tie there in secret,

And the face of that father,

Still warm with the mystery of lather.

They are more fathers than sons themselves now.   

Something is filling them, something

That is like the twilight sound

Of the crickets, immense,

Filling the woods at the foot of the slope   

Behind their mortgaged houses.

When I wrote about disappearing into the fire, I spoke about the emotional burden of being an entrepreneur. But David, and others, eventually wrote about the burden of not being an entrepreneur, of not doing what’s been in the hearts for years.

One woman wrote about the sense of time being wasted, of the dream deferred drying up like a raisin in the sun (I’m feeling the poetry today.)

We all feel it, men and women: the poignant pain of closing the doors on the dreams. And yet, some rail, some fight back, some fight on.

“How do you know when to give it up?” one reader asked, plaintively. He’s worked for years on the system, the implicit architecture. He knows—with absolute certainty—that if adopted, his architecture will radically and inalterably change the way we all interact with information. He knows with the same certainty that he knows his name, knows the way his kids smell after a bath, or the way their laughter drifts down the hall after they’ve supposedly gone to bed, gone to sleep. He knows. But no one will fund it.

I tell him that the most difficult obstacle seems to me that there are simply no investors in the idyllic community he lives. And he knows that’s true; knows it better than I do.

I tell her that as much as she believes her vision to be true, it won’t work unless she has the capital to fund it. And she wants to know why lesser ideas get funded when hers languishes.

And I tell them both that I can’t tell them when they should give up. Only they can answer that question.

Pulling back, I think about my own dreams—those realized and those deferred. I think of Jung and his notion of unlived lives…and how each  of us faces the realization that there are aspects of us which must, simply must, be realized, be lived if we’re going to rage against the dying of that light.

When we find ourselves in midlife depression, suddenly hate our spouse, our job, our life—we can be sure that the unlived life is seeking our attention. When we feel restless, bored, or empty despite an outer life filled with riches, the unlived life is asking for us to engage. To not do this work will leave us depleted and despondent, with a nagging sense of ennui or failure. As you may already have discovered, doing or acquiring more does not quell your sense of unease or dissatisfaction. Stuffing down these rogue feelings or dutifully serving your life’s routines will not suffice. Neither will “meditating on the light” or attempting to rise above the sufferings of earthly existence. Only awareness of your shadow qualities can help you to find an appropriate place for your unredeemed darkness and thereby create a more satisfying experience. To not do this work is to remain trapped in the tedium, loneliness, agitations, and disappointments of a circumscribed life rather than awakening to your higher calling.” Robert A. Johnson and Jerry M. Rhul, Living Your Unlived Life.

For David, for the woman, for the others…walking into the kiln is living that unlived life; it’s awakening to that other life that’s out there, beyond the ennui. Yes, the emotional burden of being an entrepreneur is high–just as high as  the cost of not disappearing into the fire.

Maybe it was the stale pastry. Maybe it was the lack of sleep. Whatever it was, though, when I heard my fellow board member say it, I felt like puking. “What we need,” he bloviated, “is a ‘world-class’ CEO.” There it goes again, I thought, the myth of a new CEO as silver bullet. Too often … (continue reading)

The ease with which they finished each other’s sentences, completed each other’s thoughts was so graceful, seamless that they could have been sisters. They’ve worked together for years and as they sat on the couch in my living room, on that Sunday afternoon, they nervously fingered the agenda they’d brought. It was a list of … (continue reading)

The late afternoon, mid-winter sun had already begun setting. My office, normally bright when the sun is high in the sky, took on a warm, almost eerie glow. As the sun set, he seemed to slink even further into the couch. Head back, legs thrust out in front him, he looked exhausted. He sighed out: … (continue reading)