Don’t be a Shouldy Business Owner

I know you’re intrigued… Shouldy business owner – What’s that?

Should What by 416styleLet me sum it up for you – “I should have” and “I should” are a shouldy business owner’s favorite expressions. Rather than actually doing or delegating tasks, he or she is should-ing them. Yup, shoulding.

How do you know if you are a Shouldy Business Owner? Here are a few clues:

  • You have been sticking receipts into a folder all year, knowing you should hire a bookkeeper so you’re not scrambling come tax season. Guess what?! It’s December 5! You should’ve hired help months ago!
  • Your voicemail is full of messages you should respond to but you don’t have time.
  • Your cloud based calendars aren’t syncing properly. You know you should do something about it but all your time is being taken triple entering your appointments into Salesforce, TimeTrade and your Google calendar. Yup, that sounds like a GREAT use of time.
  • Links on your website aren’t working properly and you should call your IT person.
  • Your business’ social media pages are stark naked, and you haven’t posted a word since you started the accounts…  Two years ago…  Yup, you should hire someone and you know it.
  • Your business contracts were admittedly borrowed straight off the internet. You merely copied the text and slapped it onto a Word document. You knew you should, at some point, put the contracts onto letterhead, but even now, five years later, you don’t have letterhead. Hmmmm…

So what is it that you SHOULD be doing right now? Obviously we LOVE the fact that you are reading our blog, but we want to help you, not hinder you. So bookmark this article in your browser and go tackle an item on your to-do list. Or, give us a shout out so we can discuss how we can help you with our virtual assistant services. You know all those clues above? We could help with each and every one of those items so it is no longer a Should item.

Come on, don’t be a Shouldy Business Owner. Take a big step forward and hire the help you need to take your business to the next level. You’ll thank us (even if you don’t hire us), I promise.


I have to admit, “Shouldy” isn’t our creation. I (Kim) have to thank my brother for introducing me to Shouldy. Jeff Newland was committed to helping individuals and businesses reach their maximum potential, and on a podcast with Dan Klass of The Bitterest Pill he discussed “Shouldy.”

Unfortunately, Jeff was taken way too soon by a senseless act of violence on October 21, 2013. My family is still looking for answers, and ask that if you or anyone you know has answers about Jeff’s death, that you please contact the authorities.


Kim SuttonKim Sutton is the Managing Partner and Chief Everything Officer of The Sutton Companies, including Sutton Strategic Solutions and Sutton Creative Studios.  She is a graduate of The School of the Art Institute of Chicago where she earned her Bachelor’s Degree in Interior Architecture.

An avid reader and passionate learner, Kim is constantly researching, studying and developing business improvement strategies. When it comes to client work, Kim especially enjoys helping her clients develop innovative marketing strategies and sales funnels, particularly when they are using Infusionsoft to automate all the heavy lifting. To find out how you can further develop your company’s marketing and automation strategies schedule a 1-hour Business Boost Strategy Session by clicking here.

In her free-time, Kim cherishes the time she gets to spend with her husband, Dave (her business partner), and five children. She also enjoys reading, knitting, writing and playing video games.

Get a copy of Kim’s FREE guide, “10 Top Tools for Small Businesses” by clicking here.


About Kim Sutton

Kim is the CEO of The Sutton Companies, including Sutton Strategic Solutions and Sutton Creative Studios. She is married to her best friend and soul mate, Dave, and together they have six children.
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