What three business problems are keeping you up at night?

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business problemsI belong to a forum of business owners that meets for a few hours once a month to share stories, solve problems, and keep each other accountable. During last week’s session, the forum leader asked: What three business problems are keeping you up at night?

Your task today is to take 2 minutes to ask yourself that question. Grab a pen and paper, and scratch out your three answers. Go ahead, I’ll still be here.

Now, I’m going to take a guess: The first two came relatively easily, but the third required a bit deeper thinking, right? That’s what happened to me, and to everyone else in the group.

As the forum leader pointed out, that third sleep-stopper is likely the most important problem to solve for your business. Whereas the first two are ever-present in your mind and on your to-do list, #3 often lurks in the background. It may be that you don’t want to acknowledge that it’s an issue, or maybe it’s a more difficult, complex, or long-term problem that can’t be addressed easily or quickly.

Sales Tip: Ask Your Clients “What 3 Business Problems Keep You Up at Night?”

In addition to using this question as a reality check on your own freelance business, it makes a fantastic exercise to incorporate in your discussions with clients and prospective clients. For the former, it provides insights on the business problems they’re having that you might be able to help with. For the latter, that’s applicable too—but more important, you’ve probably made them think about something that they hadn’t considered. In fact, that’s my favorite comment I ever hear in a client meeting: “Huh. I haven’t thought about that before.” There’s no tool more powerful than that when it comes to selling your expertise and services.

Photo courtesy of Pexels.

In the comments: Did I guess correctly that the third item was more difficult to generate—and probably the most important one to solve for your freelance business?

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  1. says

    Hmmm… OK, let’s see:

    1. Get clients
    2. Get noticed
    3. Make a compelling case for illustration and humor

    I thought of them all in pretty quick succession, probably because they’re all related!! Great post, Jake, and I thought using “What 3 Biz Problems?” was a great tip. Many thanks, always wishing you success!

  2. says

    Oh, you guessed it!

    The first two really are the same old, same old:
    1. Find more work
    2. Gain new clients

    The third one, on reflection, has to be to continue to bolster my reputation and keep clients coming back. That’s my third one at the moment — if you’d asked me on April 15th, it would have been to keep current with my tax payments. 😉

    • Dr. Freelance says

      Thanks for commenting, Lori–and thanks for tweeting, too. Reputation-bolstering is a great one! For the record, I filed an extension on my taxes, so that one’s still lingering on my to-do list, if not the insomnia list.

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