Earlier this year, I launched the Savvy Shopkeeper Quiz. After taking the quiz, you’ll know what stage of your shopkeeping journey you’re in and get a few free resources hand-picked with shopkeepers like you in mind. It’s beneficial for shopkeepers to understand WHERE they are on their journey, and the quiz gives shopkeepers that clarity! 

The quiz also helps ME understand where you are. It helps me empathize with what you’re going through, teach in a way that resonates with your stage, and allows me to steer you toward the resources and podcast episodes that are the most useful for you.

Haven’t taken the quiz yet? Click here to learn what stage of your shopkeeping journey you’re in!

The Five Stages of Every Shopkeeper’s Journey

There are five stages to a shopkeeper’s journey: Aspiring Shopkeeper, Savvy Starter, Profitable Planner, Growing Retailer, and Retail CEO.

At this year’s retreat, all of the attendees had a blast meeting shopkeepers from their stage. I broke attendees out into smaller groups based on their shopkeeping stage. I grouped Aspiring and Savvy Starters in one group, and each of the other stages had their own groups.

As I walked around to each group, listening and checking in, it became clear that these shopkeepers craved more time talking with each other and bonding over their shared experiences. It was incredible! 

Since launching the quiz, I’ve also learned that the amount of time a person has IN BUSINESS doesn’t matter. For example, some shopkeepers have been in business for 25+ years and aren’t at the Retail CEO Stage, and some shopkeepers have been open for less than one year who ARE at the Retail CEO Stage.

I often tell shopkeepers to create the type of business that works for THEM. You can hear about this in Episode 96: Retail Success is Subjective. It explains why the length of time in business is irrelevant. 

The Final Stage: Retail CEO

Recently, I’ve been speaking more with the Retail CEOs in Master Shopkeepers and identifying what makes them and their stage unique. Their perspective is really insightful, and I’m excited to share more about the type of business owner that reaches the Retail CEO stage. 

On the whole, Retail CEOs are risk-takers. They’re visionaries who can think outside the box. 

They keep growing because they aren’t bogged down with the daily details of their businesses. This doesn’t mean that they don’t occasionally clean toilets in their stores or take out the garbage themselves, but maybe this isn’t a regular occurrence. 

Retail CEOs aren’t better than anyone else—they’ve just become strong delegators and have learned to let go of what doesn’t matter.

Here are ten words I use to describe the Retail CEO.

1. Freedom

Yep, Retail CEOs have free time. They’re freer than most shopkeepers in other stages. 

2. Flexibility 

They started their businesses to do what they want when they want, and they’ve earned this. They have a sick kid, no problem. If they want to go to lunch with friends or take a long weekend for a girl’s trip, they can! It’s all because they have a team running the business.

3. “Passive” Income

Some Retail CEOs may only be in their stores occasionally. The store is a well-oiled machine; they only need to go in when they want or as required. 

4. Large Team

Retail CEOs tend to have larger teams of 10+ employees.

5. “Well-Oiled Machine”

Their businesses run pretty smoothly. There are the occasional bumps in the road, but overall, everyone knows their roles, and stuff gets done!

6. Systems 

Systems support those well-oiled machines! Retail CEOS have their systems and processes in place. Most are documented, and there aren’t many unknowns.

7. Expansion 

Almost all Retail CEOs have expanded. They’ve taken up more space next door, opened more locations, or even opened sister stores. And they definitely have LOTS of storage, sometimes in the form of a warehouse.

8. Profit AND Pay 

Yes, Retail CEOs definitely pay themselves AND turn a profit. They’ve learned to improve margins and get out of debt. A bookkeeper, CPA, or both supports them, but that doesn’t mean they’re hands-off with their finances—Retail CEOs know how to read their P&L! Shopkeepers in this stage know how to be profitable.

9. Risk Taker 

Retail CEOs are natural risk-takers, even if they don’t see themselves this way. They step into discomfort rather than resist it because the return on investment is worth trying. They don’t want to be the “what if” person.

10. Visionary 

These high-level shopkeepers have TIME to think. They’re always considering how to scale, grow, take on other ventures, and give more value.

To put it simply: Retail CEO is truly a BOSS UP stage. 

Finding the Shopkeeper Stage that Feels Right for You

Not everyone wants to be a Retail CEO, and that’s okay! For example, many shopkeepers prefer to work alone and are not interested in hiring. Retail CEO probably doesn’t sound aspirational to them (in fact, it might sound more like a nightmare!). 

But if reading these characteristics fills you with excitement and inspiration, then you know this stage is for you. 

Whatever stage you’re in and whatever stage you want to work towards, please know that there is NO judgment here. I am here to cheer on and support you, no matter what stage you’re in or what stage you want to grow into.

If you haven’t taken the quiz yet—or if you think things have changed for you in your business over the past few months—go take the quiz

You’ll learn what stage you’re in and what that means. Plus, you’ll get a curated list of 4-6 podcast episodes for your stage, free resources, and lots of helpful information. 



  • [05:37] The Five Stages of Every Shopkeeper’s Journey
  • [09:43] The Final Stage: Retail CEO
  • [15:26] Finding the Shopkeeper Stage that Feels Right for You

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