Dr. Freelance

  • HOME
  • BOOKS
  • WEBINARS
  • BLOG
  • PUBLISHING
  • ABOUT
    • CONSULTING
    • ABOUT DR. FREELANCE
    • ABOUT JAKE POINIER
    • CONTACT US
  • Get New Clients
  • Make More Money Freelancing
  • Manage Your Freelance Business
  • Videos
  • General

What three business problems are keeping you up at night?

April 24, 2019 by Jake Poinier

Like this post? Please share it!

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.

Favorite comment in a 1st meeting w/ a #freelance client: “Huh. I haven’t thought about that before.”

Click To Tweet

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?

Like this post? Please share it!

Filed Under: Get New Freelance Clients Tagged With: business problems, prospective clients, reality check, relationship strategies, sales strategies

Like What You've Read? Subscribe to Dr. Freelance

* indicates required

Comments

  1. Mark Armstrong says

    April 24, 2019 at 11:26 am

    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!

    • Jake Poinier says

      April 24, 2019 at 11:30 am

      Thanks, Mark. Always appreciate your positive comments. Happy Humpday!

  2. Paul Perry says

    April 25, 2019 at 2:15 pm

    Motivation. It’s difficult to keep a consistent level of positive motivation when working alone. Starbucks anyone?

    • Jake Poinier says

      April 25, 2019 at 2:40 pm

      True story, my friend!

  3. Lori says

    May 9, 2019 at 10:32 am

    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

      May 9, 2019 at 10:53 am

      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.

  4. Elvis Michael says

    September 16, 2019 at 4:15 pm

    Interestingly, my business problems are usually related to my abundance in creativity. You probably know what im talking about as a fellow freelancer: A lot of us are exploding with creativity at any given time.

    We want to try new ideas, tweak existing ones, and generally obsess and daydream about them. So these days i write down the most promising ones for future reference, while (trying) to discard the rest.

    Thanks for the good, short read, Jake!

    Elvis

    • Jake Poinier says

      March 26, 2020 at 10:16 am

      Thanks for the thoughtful comment, Elvis — sorry I didn’t reply sooner!

Subscribe to Dr. Freelance

* indicates required

Books by Jake Poinier

Follow Dr. Freelance on Twitter!

Tweets by @DrFreelance

Categories

Recent Comments

  • Jake Poinier on A freelance pep talk and open-line Friday on 3-26
  • Joy Drohan on A freelance pep talk and open-line Friday on 3-26
  • Jake Poinier on What three business problems are keeping you up at night?
  • Jake Poinier on A freelance pep talk and open-line Friday on 3-26

Your Prescription for Success

Looking for better paying freelance jobs? Trying to improve your flow of referrals? Tired of marketing strategies that don't work? Join Dr. Freelance for one of his upcoming webinars! READ MORE.

Search

Book Better Freelance Business

Three Dr. Freelance Guides offer professional business advice for freelance writers, editors, designers, and other solo creative entrepreneurs. Whether you want more clients, better pay, more referrals, or all of the above, you've come to the right office. READ MORE.

Healthy Connections

Dr. Freelance enjoys talking shop on social media. Check him out on Twitter, Facebook, Google+, or LinkedIn to hear his latest diagnosis or ask a question about your business.
  • HOME
  • BOOKS
  • WEBINARS
  • BLOG
  • PUBLISHING
  • ABOUT

Dr. Freelance: Healthy Business Prescriptions for Freelance Creatives.
All contents Copyright © 2023 by Jake Poinier. All rights reserved. Privacy. Fair Use of Content.
Dr. Freelance® and More Cowbell® are trademarks of Boomvang® Creative Group, LLC, and More Cowbell Books, LLC, respectively.