The 5 Day Reboot

We’ve got to help each other. Тhat’s why we’re so glad you’re here. We’d love to hear from you as you take this journey. You can reach us on Twitter @reboothq, engage with fellow participants using the #5dayreboot hashtag or connect directly to the team with an email at

– The Reboot Team

“Work is where we can make ourselves; work is where we can break ourselves.”

David Whyte

David Whyte


Adrenaline is addictive; it’s such a rush to, well, rush from task to task. Moreover, it can also feed a sense of superiority: “Geez what I’m doing must be so important, look at how fast I’m moving. Look at how slowly you’re moving.”

More deeply, it’s also fed by the enmeshing between work and identity. I am what I do and if what I’m doing is fast and, therefore, important than I must be worthy enough to have earned your respect, your love.

While everyone—myself included—can fall prey to using work as a prop for self-meaning, I find that founder/entrepreneurs are particularly susceptible to this loss of self. This despite the fact that the ultimate expression of the trend is a narcissism that borders on socio-pathology; think of the many, many asses in business whom we admire precisely because they have a single-minded focus on execution, causing everyone around them to pant their way through the workday.

Of course we don’t put it that way. We admire them, we say, because they are successful.

Unfortunately then we never get around to debating the meaning of that word: successful. We too infrequently pause and consciously, and with all of our adult awareness, define for ourselves success.

One of my most popular blog posts is titled Disappearing into the Fire…the seductive lure of losing one’s self in work. This enmeshing, this panting, this forever chasing higher and tougher goals is yet another form of Disappearing.

But, but, but…there is a power in reaching; “Ah, but a man’s reach should exceed his grasp,” said Browning, “or what’s a heaven for?” There’s an audacity in reaching, in dreaming of a new way to change a light blub, search for something on the internet, connect people across time and space. And we should never lose that audacious reach.

But to lose one’s footing in the reaching serves no one.


When I rush from task to task, I a) experience an adrenaline rush b) feel superior to others who are “not working as hard” c) get affirmation from the rushing d) expect that people will respect me more.

Who would you be more likely to turn to for advice: a hard-charging “successful” person or a person who you feel is “thoughtful”? Are there advantages to one or the other?

Coming tomorrow: Most startups fail. To survive, most CEOs adapt the mentality that “It won’t happen to me”. Why is this so difficult to digest?

Defining Your Work and Your Life
Why I Quit Being a VC

“We are not devastated by failing to obtain a goal. We’re only devastated when our sense of self esteem and self worth are dependent upon achievement of that goal.”

William James

William James


He looked up at me with frustration. He was pissed. He’d hired me, he said, to help him get his life in order. And he was still not getting things organized, still not getting to the gym, paying his bills on time, meeting women.

Two months before he’d come in for his first session: “I’m 30 years old,” he’d told me, “and I have no idea what I’m supposed to do with me life.”

And when I’d probed that question he’d said: “I don’t want to deal with that ‘inner child’ crap.”

And so here we are. Two months in and he’s gone through a ream of spreadsheets and host of systems—Gmail-based reminders to get him to do his workouts and file his quarterly taxes; an iPhone app, even, to remind him to eat and to take a break from email during the day. He’d read dozens of books from the likes of David Allen, Ram Charan (all wonderful and helpful resources). Damn, he’d hired a coach in order to help him clear his desk.

And none of it was working. And he was angry. With me.

Recognizing and releasing myself from the fear that had arisen in response to his anger, I said, “Well, it’s about time.”

There comes a moment in everyone’s process when we’ve finally had enough. The tools we’d used for so long to prop up a view of ourselves breakdown. The systems, the limiting beliefs, we use to maintain our precious point of view about ourselves start to fail and we face that delicious, juicy, frightful, gut-wrenching existential realization that it’s just not working.

And so…

There are other Now What? moments, of course. Getting fired is a big one. Breaking up is another–little and large deaths, all of them. When Things Fall Apart is a GREAT resource for when, well, things fall apart.

But even those moments, as painful as they can be, pale in comparison to the moment when you realize that most of what you believe to be true about yourself is false or, at least, deeply flawed in its logic. And the bubble of who you are bursts.

“Alongside our greatest longing lives an equally great terror of finding the very thing we seek. Somehow we know that doing so will irreversibly shake up our lives, our sense of security, change our relationships to everything we hold as familiar and dear. But we also suspect that saying no to our deepest desires will mean self-imprisonment in a life too small. And a far-off voice insists that the never-before-seen treasure is well worth any sacrifices and difficulty in recovering it.

And so we search. We go to psychotherapists to heal our emotional wounds. To physicians and other health care providers to heal our bodies. To clergy to heal our souls. All of them help–sometimes and somewhat. But the implicit and usually unconscious bargain we make with ourselves is that, yes, we want to be healed, we want to be made whole, we’re willing to go some distance, but we’re not willing to question the fundamental assumptions upon which our way of life has been built, both personally and societally. We ignore the still, small voice. We’re not willing to risk losing what we have. We just want more. And so our deepest longing is never fulfilled.” From Soulcraft by Bill Plotkin

As he looked at me, his anger dissipated slightly, letting his fear come up. Then, facing his fears with his head slunk into his hands, he connected with what Trungpa Rinpoche called the genuine heart of sadness. And that’s when we began coaching.


Where are you right now?

a) I think the bubble of who I am is about to burst, and I’m not sure I want it to

b) My want-it-all voice is overpowering the still, small voice which is saying, “the never-before-seen treasure IS worth the sacrifice of discovering it.”

Coming tomorrow: ⅔ of all CEOs are struggling. Feelings of frustration, disappointment, irritation, and overwhelm are the norm. There is a cyclical connection between physical, mental and emotional that can empower us to thrive or expedite our demise. Scientific research shows that to be extraordinary requires downtime. If you don’t take time, your company will fail.

Most Startups Fail

“I don’t have a problem with what you’re doing, that’s your choice. What I have a problem with is you lying to yourself about why you’re doing the things you’re doing. You have a choice.”

Jerry Colonna

Jerry Colonna


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.

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.


Has there been a significant time in your life when you “closed the door softly” on one of your dreams? Did someone else help you make that decision, or did it just come from “your gut”?

Coming tomorrow: We have a choice: What kind of adult would we like to be? What kind of leader would we like to be? To answer this question you must courageously look inward with honesty.

Problem of the Potter

“Some of the hardest things to improve are the hardest things to admit.”

Bijan Sabet

Bijan Sabet


They often come to me, their coach, because they don’t have any place else to put the feelings. They’ll sit on my couch, or pace while they talk on the phone, pausing as we grapple with issue after issue after issue. The common denominator is always people. When I first take on a client I warn that I don’t have a magic wand. Nevertheless their wish for some elixir to mend their relationships is heart-breakingly visceral.

When they start, they often think the hardest part is figuring out what to do but they’re inevitably knocked on their ass by the task of leading. And when they make mistakes–when they fail to lead–their identity, self-esteem, and ability to provide—as David Whyte notes–sometimes explode.

We all too often break ourselves in the work of becoming a CEO, a manager, a leader.

The only answer, the only balm against the inevitable existential pain of becoming the leader we were born to be is to see the lessons implicit in the practice of becoming.

“In the course of studying how geeks and geezers became leaders,” writes Warren Bennis in the introduction to his classic, On Becoming a Leader, “…I discovered that their leadership always emerged after some rite of passage, often a stressful one. We call the experience that produces leaders a crucible…the crucible is an essential element of the process of becoming a leader…Some magic takes place in the crucible of leadership…The individual brings certain attributes into the crucible and emerges with new, improved leadership skills. Whatever is thrown at them, leaders emerge from their crucibles stronger and unbroken.”

The magic, the alchemy, occurs when what we do mixes with who we are and is cooked by the heat of what we believe.

Take as an example a client I worked with intensely over the last few weeks. She and a co-founder have been killing each other (okay, I have a flair for the overstatement…still, they have both been getting sick with a host of ailments—migraines and stomach problems). The arguments had gotten so bad that neither could stand to be in the same room with the other. Even I was exasperated. During one late night call, I asked my client to forget, for a moment, whether her co-founder was right or wrong. “I don’t care who’s right,” I said with my voice rising. “The only thing we have to focus on is what are you supposed to be learning from this.”

There was a long silence. I thought, “Okay. You’ve really pushed her too far. You and your woo-woo ‘lessons in the pain’ crap.” But then: alchemy. She opened up. “This is really shameful to admit,” she began, “but I know I’m a pain in the ass because I have to be right, all the time. I know it’s wrong but I can’t stop myself.”

And with that we had something to work with. I pressed her: Given this tendency, what do you really believe? What values do you hold? What kind of company do you want to build? And what kind of adult do you want to be?

Over the next few weeks, on guard for her need to be right, we carefully went to work changing her approach to the co-founder. For her, the crucible moment came in facing her shame, acknowledging who she really has been and as a result she got to choose how she wanted to manage and who she wanted to be.

We forge our truest identity by facing our fears, our prejudices, our passions, and the source of our aggression.

The Buddhists teach that for the steadfast warrior to emerge, we’ve got to break open our hearts to what is.


Like the co-founder who painfully admitted that she “had to be right, all the time,” do you have a belief, a value that you so cherish that it’s hurting how you lead others?

What would it take for you to dredge up that truth? An intervention? A empathetic, listening friend? A threat of being fired by your VC/director/chair/CEO?

Coming tomorrow: Running a startup is running a marathon every day. To survive, you have to build and maintain a base that supports you.

Crucible of Leadership

“If the first thing you reach for in the morning isn’t yourself or your partner, you have a problem.”

Jerry Colonna

Jerry Colonna


One day, a blood test reveals a suspiciously high PSA count. Your doctor says he’s “99% sure it’s not cancer” but, to be safe, go see the urologist. So you see the urologist who, after the thorough exam, rules out simpler issues and says you’ve “a 20% chance of cancer.”

So, to be safe, you take another blood test. That test comes back and now there’s little chance there’s any problem; looks like the first test was wrong.

Or then there’s the client, whose teenaged daughter was diagnosed with Lupus the day his $10 million financing closed. Or the other client whose lead investor decided he should be fired the day before the company received a term sheet for a new $5 million investment. Or the woman who, on Friday, agrees to marry her boyfriend only to decide on Monday that he’s not her soul mate.

“How do you do it?” he asked over the phone. “How do you go into the office when all you can think about is what’s happening at home?”

Or in your relationship, I think, or, even, your own body.

Dramamine,” I tell him, making him laugh.

Up. Down. Down. Up. How do you ride the roller coaster?

How do you survive the everyday, ordinary craziness that defines life?

Meds can help I suppose. But, the only real chance we’ve got of surviving, indeed maybe even thriving in, the chaos of ordinary life is to develop a centered core: A set of beliefs, rituals, and inner-knowledge that not only remains unshakable with every gut-wrenching drop but, in fact, deepens over time into a philosophy that is at once unique and lasting.

I think of my own ritualistic behaviors–rising before dawn, journaling, exercise, and meditation—and see them not only as manifestations of my own beliefs (journaling develops a greater self-awareness; exercise provides the short-term benefit of anxiety-release while promoting long-term fitness, and meditation as a practice of accepting things just as they are), but as a means to create order out of the everyday chaos.

Regardless of the inevitable drops, such core systems of belief steady the self and make the everyday possible.


If surviving the Roller Coaster Life requires something unshakeable inside us to point the way, would you say you

a) are so busy vomiting from the ride that you can’t think straight
b) have a shaky compass that doesn’t always seem to point True North
c) have some great rituals, if only you would dust them off

Can you say why?

Work- Life Balance
The 5 F’s

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