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Fear Is A No No – Except at Night

By - May 20, 2010

I love Fred’s thoughts on being an entrepreneur – he backs some of the best. I don’t write often here about my own experiences, but I can tell you, I certainly will, once the dust settles and I am not actively running a company. Upon reflection, I realize I’ve been doing this a long time. In fact, I’ve been starting companies since 1987, though my first real startup as a founder was in 1992. (That was Wired).

In today’s post, Fred writes:

If I look back over 20+ years of entrepreneurs I’ve backed, the ones who were anxious and afraid of failure most certainly had worse outcomes than the ones who were agressive and confident. You simply can’t be tentative in a startup. You have to go for it at every chance you get.

And if the leader of the organization is anxious, his or her fear pervades the organization. Everything comes from the top in a company. So it is best to have to have a leader who exudes confidence….So if you are starting a company or building one, face your fears and move past them. It’s critically important to your company.

I agree – in the day time, at work, in front of your staff, your investors, and your partners – you must exude confidence. They are looking at you as True North – and your company is the ship sailing by that particular bearing.

But what Fred doesn’t reference – though I know he is well aware of it – is what happens in the dead of night – at least for just about every successful entrepreneur I know. As dark gathers and you attempt to put the work away to steal a few hours of sleep, you are inevitably visited by questioning spectres – waking apparitions of failure dancing in the shadows of your doubt, dodging your attempts to force them into the light of reason. For more nights than I (or my wife) care to count, I’ve entertained and processed a thousand failure-filled scenarios, each frolicking endlessly in my mind, each disappearing as quickly as they came, unless captured, quickly and with mixed results, in scribbled notes on index cards, or, if I truly capitulate, in the gloaming of my newly awakened computer monitor.

It’s enough to make you mad. But then again, this particular madness is embraced, again and again, by a certain breed, and folks like Fred keep giving us money to embrace it. Were I more devious, I’d call Fred a pusher of sorts, a dealer in madness and joy. In fact, I’m quite certain that’s what he is.

I’ve been starting companies for a solid 18 years now, and for at least half of those years, I’ve been visited by these spirits nearly every single night.

May they never yield.

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13 thoughts on “Fear Is A No No – Except at Night

  1. Without having been in your position, your writing here rings as true as things I’ve felt on and off throughout my adult life. The best leaders are beautifully, tragically human. Humans quake with fear when no one is watching. Humans doubt themselves. Leaders compartmentalize this doubt and fear; they suck it the hell up and soldier on, if not for them, then for the people that look to them for guidance.

    Thanks for writing this, John.

  2. John says:

    Thanks Ian. I rather liked writing it. I’ve been thinking about this for a while now. Wondering how it is I got to some sort of peace with the nightly dance of a thousand options.

  3. Perry says:

    John you’re spot on, and I agree that the perspective Fres espouses is really about the “outward face” skills of an entrepreneur.

    Showing blind faith and ambition to your team bullds their confidence and focus; steadfastness in the face of Rapid and semi-predictable change is the hallmark of tech industry leadership and damn good bus dev results IMHO.

    I personally find that the dead of night fears you illuminate breed some of the most creative and productive business decisions. I’ve found myself time and time again waking fully energized from those sleepless nights, go figure!

    And hey, call me some night; i’ll probably be up ;)

    it is a critical success

  4. Elie Seidman says:

    Brilliant.

  5. David says:

    Have you read reWork from the guys at 37Signals? What do you think about “work smarter not harder” discussion. Running 2 start-ups I tend to have to do both :)

    Great post (replying at 4:48 am in NYC ;) )

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  7. Lester Puppo says:

    It is great to see an article of this kind ecpressing such a realistic and sometimes neglected idea of what happens when business causes stress. As a matter of fact, it’d be strage if you were really excited and willing to achieve a goal and you managed to sleep like a baby. However, keeping a healthy life style is a must, especially if you are planning to continue running your business, and therefore, it is important for you to try to relax and think about business with a fresh mind.

  8. Hi John
    Thank you for this post; it is incredibly timely advice for me.
    Onwards and upwards…

  9. AO says:

    great post

  10. andreaitis says:

    beautifully said. i’m stressed just reading it, reminding me of the thing i thought of in the middle of the night that i didn’t get up and write down because i told myself i would absolutely remember it and then of course i wake up unable to pull the crystallized thought from the brain fog.

    i get that feeling in my chest, kind of like heartburn. Entrepreneur burn. But that’s right, because that’s where the madness and joy live. It’s all in the heart.

  11. andreaitis says:

    beautifully said. i’m stressed just reading it, reminding me of the thing i thought of in the middle of the night that i didn’t get up and write down because i told myself i would absolutely remember it and then of course i wake up unable to pull the crystallized thought from the brain fog.

    i get that feeling in my chest, kind of like heartburn. Entrepreneur burn. But that’s right, because that’s where the madness and joy live. It’s all in the heart.

  12. Cowicide says:

    Courage is resistance to fear, mastery of fear – not absence of fear. – Mark Twain

  13. Tom Nocera says:

    “Fortune favors the bold.”