This post is part 4 of a 5-part series for the Retail CEO Challenge. Read the other parts here: part 1, part 2, part 3, part 5

I’ve gotten some amazing feedback from the Savvy Shopkeeper community on the Retail CEO Challenge! As a refresher, here’s what we’ve covered so far in the challenge:

  • Why CEO time is important
  • How systems & processes can simplify your business while saving you time
  • What tracking can do for you as the CEO of your business

Along with the worksheets we’ve covered during the Retail CEO Challenge so far, there are other valuable resources included in the challenge bundle. Some of these include the year-at-a-glance calendar, which shows you the major holidays and retail dates for 2021, as well as a full-year marketing calendar, and goal setting worksheets.

Where We’re At in the Retail CEO Challenge

If you’ve been following along with the Retail CEO Challenge, here’s what you should have completed so far: 

  • Created & personalized your CEO binder (episode 56)
  • Printed all the worksheets that you want to use and added them to your binder
  • Prepped some of the worksheets for the year, such as the monthly sales tracking worksheet (episode 57

Next Steps: Set a CEO Date  

Now that we’ve gotten all of the above set up, I want you to set a true CEO date with yourself, your business partner, or your store manager. 

Take a half or full day off from your shop and create some quiet time—if this means asking your spouse, kids, and employees to not disturb you, then so be it! Remember, you have to set boundaries and people will need to start learning how to respect those boundaries.

Make your favorite beverage, go into your favorite room or sit in your favorite chair, and make this CEO date special!

Filling Out the Business Health Checklist

During your CEO date, you should work through the Business Health Checklist that I’ve included in the challenge bundle. This worksheet has evolved over the past three years, with the most recent revision resulting in a comprehensive 2-page checklist with all the categories you need to check in on. With this worksheet, you can truly take a good look at your business.

An important note: as shopkeepers, we don’t always take the time to really reflect and determine the true health of our business. We also tend to focus on revenue above all else. But the truth is, revenue should not be your only focus! Of course it’s important, but it isn’t the only measurement of your shop’s success.

The Business Health Checklist is made up of 15 categories. For each category, I have several sentences that will help you have a conversation with yourself about that category in your business.

For example, category #1 is Business Happiness. “Work Less. Profit More” truly epitomizes the mission of Savvy Shopkeeper. I sincerely want shopkeepers to work less—I often see how unhappy they are that their business consumes too much of their lives. And I want them to profit more because I see some shopkeepers working for years without collecting a single paycheck.

So category #1 is “BUSINESS HAPPINESS: My business allows me sufficient freedom to pursue everything that I want. I have sufficient time for friends, family, and leisure activities. My business energizes me and compensates me financially.”

Another category is “RESILIENCY & BUSINESS CONTINUITY: I have business insurance that will cover accidents and disasters. I have a recovery plan that will allow me (or a designee) to continue to run my business. All my business records are regularly backed up. If applicable, I am setting my business up to successfully sell it.”

You can put a checkmark, a grade, or a simple smiley/frowny face in the checkbox for each category. Whatever you may do, the important part is that you take the time to reflect on each category.

Other categories on the Business Health Checklist cover social media and marketing, cogs and expenses, your POS system, your online presence and website and more! That’s why you’ll want to allow for at least 2 hours of time on your CEO date.  

Set Your Goals for the Year

After you complete the Business Health Checklist, you’ll take the Goal Setting Worksheet to set your goals for 2021 and the future.

If you review the Resiliency & Business Continuity category and realize it’s been years since you looked at your insurance policy, it’s time to set a goal to review your policy and call your insurance agent. This is also true if you’ve recently looked at your policy and you’re underinsured—maybe you’ve grown from 30K in inventory to 100K+ in inventory over the past few years. 

When you’re done, you might have lots of goal setting worksheets to complete. What’s nice about the goal setting worksheet is that there’s an area on it where you can DELEGATE the task.  If you have team members, please utilize them.  Don’t try to tackle all of your goal setting worksheets yourself! You have a team for a reason.

There’s also an area on the worksheet where you can assign a timeframe for the task. Maybe you’ll handle some tasks in Q1, others in Q2, and you might even assign some to 2022. That’s okay! I personally know we can’t do it all and we certainly can’t tackle 1 year of goals in 1 or 2 months.  

Be realistic, give yourself some grace, and just START. Progress in this instance is better than perfection and the health of your business is too important to neglect.

And remember, I DO THIS in my own business. This isn’t just some random idea that I came up with or something that doesn’t serve me well.

Sign Up for the Retail CEO Challenge

It’s not too late to sign up for the challenge! 

Not only do you get all the worksheets I’m talking about, but you’ll get the Year-End Retail CEO Report (check out part 5 of this series for details). 

PLUS I’ll be teaching a one hour masterclass followed by a one-hour Q&A session on February 8, 2021 at 1 PM. If you can’t attend live, you will get a link to watch the replay!

Don’t forget if you’re in Master Shopkeepers, you already have access to all of this information and if you’re a Shopkeepers Lab member, there’s a special discount code listed in the Announcements in the Facebook Group.

The 2021 and 2022 Retail CEO Challenges are now closed. However, all of the worksheets, including the Business Health Checklist and Year-End Report are available in the Shopkeeper’s Lab. Members can find these in the CEO Time + Worksheets module. Click HERE to learn more.



  • [01:22] Where We’re At in the Retail CEO Challenge
  • [06:39] Next Steps: Set a CEO Date
  • [09:28] Filling Out the Business Health Checklist 
  • [15:39] Set Your Goals for the Year
  • [19:19] Sign Up for the Retail CEO Challenge

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