Help! When the Entrepreneur Boss Asks for the Impossible

I once had an entrepreneur ask me to produce a Flash Mob similar to the one he had seen during the Black Eyed Peas performance on Oprah.

He wanted it for the up-coming weekend.

Another entrepreneur wanted to concept, develop, manufacture and launch an energy drink.

He wanted it for a trade show in one month.

Really, guys?

Anything that makes Oprah squeal like a one of her audience members on free-car day, will take more than a week to produce. And consumable products? Well, they typically take more than 30 days to get to market. What is it they say about the building of Rome?

Work in the Colosseum
Such is life when you work for an entrepreneur. You’ll be expected to do the impossible. In fact, the expectations set for you will be as high as the seemingly impossible goals the entrepreneurs set for themselves. Remember entrepreneurial thinking, as crazy as it sometimes seems, changes industries. It changes the way we live our lives and do business. To produce all this change, a few employees may be thrown to the lions. So gear up.

Help when your entrepreneur boss asks for the impossible

Follow me. I know the way.

Life Savers (not the candy kind)
To help you rise to the challenge I’ve added a resource section to this blog. It includes a list of suppliers and vendors that have saved my neck in the past. From advertising veterans like the folks at Kidvertisers, to specific contacts at large research companies like Mintel. The people on this list understand what an S.O.S. call is, and they react appropriately.

My Gladiator Score Card
Sometimes at the end of the battle there’s singing and dancing in the streets. Sometimes the lions win. Although we did pull together a miracle launch plan for the energy drink, the entrepreneur had already changed his mind before we pulled the trigger. Figures.

As for the Oprah-style Flash Mob? Defeat. There simply aren’t enough Life Savers in Willy Wonka’s factory to pull that one off. Sorry guy.

Working for Wonka? Know this: The impossible may just be possible with the right resources. Arm yourself well and get in there to fight. You might be surprised by what you can accomplish.

[Photo credit: Katrina Brown via Shutterstock ]


  • Tara

    Reply Reply November 4, 2010

    I hate it when people set unrealistic targets, worse still is when they set deadlines before they even give you he information you need to do the job. Usually there is some sort of compromise that can be made. I just wish people would think ahead more – you always know the project has been sitting on their desk or running around in their brain for ages before telling you.

    • admin

      Reply Reply November 4, 2010

      Tara: I think with entrepreneurs it is more about the idea running in their brain more than the entrepreneur intentionally keeping details secret.
      If we could just get the hampsters powering the wheel that runs their brain to start sending us memos, we’d be golden!

  • Corinne Edwards

    Reply Reply November 4, 2010

    You are going to laugh, Kathy, but –

    I love it when a client wants the impossible.

    One I worked on –

    “My package did not arrive from Florence.”
    What did you buy?
    “I don’t remember.”
    Do you have receipt?
    “No, I don’t remember the store.”
    When did you buy it?
    “Maybe six months ago.”

    I found it. The shipment was up for auction in US customs in Miami.

    ( Hint: I called every store listed on her credit card)

    It is challenging. In my next life, I would like to be a private eye.

    • admin

      Reply Reply November 4, 2010

      Oh my goodness. Classic example Corrine.

      Oh, and I’ve lost my car keys…can you help?

      • Corinne Edwards

        Reply Reply November 4, 2010

        Sonia Choquette, the famous psychic, says we all have a helper angel.

        Not our usual Guardian Angel.

        Ask. It works for me.

  • RM

    Reply Reply November 4, 2010

    I LOVE LOVE LOVE a challenge so I guess that’s how I’ve survived 10 years of working with an Entrepreneur Boss. I’ve seen people come and go and I think a successful employee with this type of boss needs to embrace challenges and enjoy working under pressure. Otherwise it would really suck to come to work every day.

    • admin

      Reply Reply November 4, 2010

      Sounds like you’re the ideal entrepreneurial employee. Did your entrepreneur boss just get lucky by hiring you, or were there some good screening questions?

      I think the key to a good entrepreneur employee is finding someone with your enthusiasm for the challenge. Lots of people think they have it. But when actually put in the center of the storm, they fold like a cheap umbrella.

  • Vickie

    Reply Reply November 4, 2010


    I love this post. I have been reminded how many times I have demanded and demands have been put on me. Your right, when we push through demands it alters how the world thinks it can function. It is GREAT that you provide resources for the assistance that work with the crazy people as we are…imagination and organization..that spells success. Great Post most definetly tweeted.



  • Larry Clark

    Reply Reply November 9, 2010

    Great post, I know the feeling, I work for that guy, Me.
    But it does shed some light on the way things really are, things take time, my wife keeps reminding me of this. a year and a half ago, when I was pulling in maybe 100$-200$ per month, I got pissed when I launched a product that didn’t take off the first day it was launched. It took about 2 weeks before I got the first sale. My wife says, relax, you’re laying the foundation, things happen in their due time. She was right, the product wasn’t something that was made to make a million over night, it was a sort of set it and forget it niche website, and it still does bring me in a nice little sum of cash each month.

    That video rocks BTW, kinda got me in the middle of the throat kinda feeling, shhh, don’t tel anyone. 🙂

    • admin

      Reply Reply November 10, 2010

      Glad your wife could bring you back to reality (I’m assuming it’s a place you’ve been before). I wonder what you would have done if that site hadn’t ultimately taken off? How/where would you have burned off steam? Or would the energy go directly into the next venture in an “I’ll show you” kind of way?

      I hear ya on the video. I think I’ve watched it a dozen times. Half with total amazement; the other half thinking OMG, he thinks we can do that by Friday?!?!

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