Guest Post

What’s the Worst That Could Happen?

by Kate Lister

I've owned three businesses over my thirty year career and without nerve, none of them would have happened, much less been successful.

Twenty years ago, I was running a successful consulting business and after falling in love with aviation and a particular pilot, I traded my business suit for a flight suit, bought a 1920's open cockpit biplane, flew it from Sonoma to Philadelphia without radios or navigating equipment, and started hopping rides. Everyone thought I'd flipped my lid. Some advised I see a shrink. Even people in aviation said it was crazy. The few others around the country who had tried it were barely making ends meet. What made me think I'd be any different? The answer — a big dose of nerve and a lot of planning; call it an informed leap of faith. Sixteen years later, having built the business into the largest of its kind in the nation, and against the consensus of several business brokers who told me I'd never be able to sell the business, I did — in three days. Why? Part nerve, and part adverse reaction to being told I couldn't. My husband (and business partner) knows that the best way to get me to do something is to tell me I can't do it.

Oddly, I'm not a very confident person, but when it comes to business, something kicks in that gives me the nerve to do things even I think are bold sometimes. I think it comes from that fact that my father brought me up to be a downside risk kind of gal. "What's the worst that can happen," he'd ask. "If you can live with whatever that is, go for it."

Since selling the business, without any income alternative by the way — something nervy all by itself, I've continued to ignore conventional wisdom. Everything I read said it's impossible to get an agent, let alone a publisher. When I decided to write Undress For Success—The Naked Truth About Making Money at Home, I made a list of the top twenty agents in the country and sent them each my pitch. Within a day I had three offers of representation. Within a week, I had eleven. Within a year, the book was written and in the hands of one of the top business book publishers in the country.

Next time you're feeling timid about picking up the phone and calling someone you perceive to be "too important" to be willing to talk to you, or you find yourself bidding for work against far more experienced candidates, or a job posting comes up that's just perfect for you except you know everyone's going to be applying for it, ask yourself, what's the worst that could happen. I'm not saying, be reckless. Reckless and nervy are two different things. If you plan for the worst, and hope for the best, you'll never be disappointed or troubled by the thought: "if only I'd tried."

By the way, I don't always follow my own advice. Remember the MasterCard commercials that showed the wild adventures and ended with: If you go, be sure to bring your MasterCard...? I stressed for months over whether to pitch the biplane ride business for one of their spots. "I'll never be able to find the right person to talk to," the face in the mirror said. "They'll never be interested in us with big ad agencies probably pitching them right and left," it continued. Finally I worked up the nerve and actually connected with the right person on the first call. She said, "oh geez, what a neat idea, but I'm sorry, we just shot the last piece on that theme." ARGH! What's the worst that could have happened?

Kate Lister, a serial entrepreneur and co-Author of Undress For Success—The Naked Truth About Making Money at Home (Wiley, 2009), Finding Money—The Small Business Guide to Financing (eBook, 2009 -- formerly published by Wiley), and companion web sites,, and

  1. I don’t think I will ever have the same amount of nerve you possess! But I do like your approach and will take your advice. From now on I will ask myself “what is the worse that can happen” but more importantly “if I can live with that then go for it!”

    Comment by Deb Evans — 11/18/2009 @ 6:23 AM

  2. I was one of those first three literary agents that responded to
    Kate’s e-mail.

    Happily for me.

    I made the sale to John Wiley & Sons.

    Bob Diforio
    D4EO Literary Agency

    Comment by Bob Diforio — 11/18/2009 @ 10:20 AM

  3. Loved you comments!
    By applying this notion in the manner you suggest the worst that could happen is that I be told “no”. I extend that notion to my teachers who I employ to deliver the COMPUTER EXPLORERS technology program at schools. I encourage them to always feel free to ask me for what they need. The worst that can happen is I will say “no”. Jointly, we often come up with a better alternative. It is not unusual that bringing their request to fruition makes our team better. But, if they do not share with me candidly and honestly then we have a barrier to delivering the highest quality service possible to our clients. My challenge is to create a safe environment where they feel free to share and ask for what they need to do a better job.

    Comment by Collette Howell — 11/19/2009 @ 7:22 PM

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