Why I Fired Myself to Have a Baby

Kiff Gallagher daddy-o

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Last Thursday, walking back to my office after a business lunch, conversation turned to life status. I told my lunch partner that my wife and I are due soon with our first.

“Congratulations–are you ready?!” she asked. “It’s amazing how much new parents need to know these days.”

“Seriously” I said, mentally drifting into a list of afternoon to-dos. “What are you thinking?”

“Well, apparently babies don’t use blankets anymore.”


“They go in sleep sacks,” she said.

A jolt of fear shocked me into the moment. What the…is a ‘sleep sack’?

The next evening at a fundraiser, after a brief presentation, I was ready for a drink. I joined my wife on a couch in the lounge. She was with a friend who turned to me.

“Dude, are you psyched or what?!”

It had been a great event, but I sensed he wasn’t talking about the nonprofit. I nodded rapidly and took a large sip of my cocktail.

“You’ll be great,” he added. “My only advice: warm the butt wipes before you use them…especially in the middle of the night. It’s a lifesaver.”

“No kidding! Thanks man.” I took another gulp to blunt the second reality shock in 24 hours.

I had clearly repressed the fact that we’re due in a matter of weeks, and I have no effing clue how to care for an infant! I am about to descend into a world in which “warming butt wipes” might actually save my life.

I do have some practice in the art of managing the unknown. As an entrepreneur, I’ve learned how the right intentions, strategy, and hard work blend with serendipity to generate a sort of creative tension that produces results.

Since the results of any new venture are never known until they are “born,” I’ve always tried to operate with a vocabulary, a vision of possible scenarios, and a view of what it would take to get the job done.

But as a daddy-preneur, I’ve got almost no vocabulary, little vision of how things might go and, clearly, no clue what it will take to get the job done. Butt wipe-warmers are just the tip of the iceberg. Something has to change.

I need to fire myself as dad of my current work-baby, MusicianCorps, in order to enroll as daddy for our real baby. I expect with service as my new home gig, soon I’ll have to charge market rates for my work in the world.

It’s a fine time for the nonprofit to mature anyway, as older siblings must, in preparation for baby. By pivoting to organizational succession and transition at work, Mom and I can better position our home product for launch in February 2014.

It might seem a bit late in the career game to fire myself…for a newborn. But life is short. I don’t want to miss critical innings. Soon enough, I’ll be back on the field of dreams, busting ass for a big vision. Somewhere.

In the meantime, call me at the home office.

I’ve never used security blankets anyway. I was late as an artist, late as a start-up guy, late in becoming a husband. As a stock trader, though, I’ve learned the value of not being too late.

The time that feels the scariest and craziest to buy is often right when you have to step into the market. Right now, I’m scared. I say: buy, buy, buy–it’s baby time.

The humble vulnerability of loving something more than anything in the world–knowing that all good intentions, strategies and hard work will still render uncertain outcomes–is a bond among parents I’m actually starting to crave.

Yes I am clueless; but I’m ready (to get ready) to join their club. Babies don’t need security blankets anyway. They need sleep sacks.

About the Author

Kiff Gallagher

is an entrepreneur, investor and founder and CEO of .

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