Working On Your Business

I’ve talked to a lot of business owners through the years. And one of the most common things I hear is, “I don’t own the business, the business owns me.” Often, an entrepreneur gets trapped into doing everything, from A-Z — “chief cook and bottle washer.” In the life cycle of a business, a business owner needs to work on growing a business, but usually gets sidetracked by the minutiae.
There are two ways to look at how you’re addressing your work operations: working in your business and working on your business. Michael Gerber coined the phrase, “Work on it, not just in it” in The E-Myth Revisited in 1995, and it’s been a part of business jargon ever since. So what does it mean?
Working IN your business is anything that is a job and also the management and execution of that job. This includes the activities that make your business run: product creation, how services are delivered, team training, and marketing/sales.
Working ON your business refers to anything that involves strategy. Think business strategy, marketing strategy, sales strategy, product development, and research. When you work on your business, you make time for the important aspects of your business before they become an urgent need. Practicing critical thinking, which is the top skill the World Economic Forum believes will need to grow by 2025, gets you in the mindset of planning ahead with strategy in mind. And that’s the key to a business’s success.
I spend more time these days working on my businesses than in them, and that’s allowed me to create efficiencies, reduce costs, recruit talent, and develop a strategic plan. There are a lot of resources out there to help you with strategic planning, but the best advice I can give is to invest in people who can take care of time-consuming tasks that allow you to focus on the core business.
In July, I hired two virtual assistants from Red Pen Virtual Assistants. Heidi helped me with a lot of tasks like research, vendor management, and administrative tasks. Bobbie was able to provide a food cost analysis for my restaurants and helped our managers with recruitment — managing Facebook and Indeed.com leads, phone interviews, and scheduling appointments.
It was a good decision and a good investment. (Bobbie’s work will save me thousands in food costs next year.) Take a tip from me and call or email Melissa Thurston, the CEO at Red Pen Virtual Assistants. She has a team of teachers and other educational pros that work as VAs for busy professionals. They’re smart, hard-working, and will save you both time and money. Start working on your business and let one of their VAs help with the rest. #GoodAdvice #TrustMe
MONDAY:
NATIONAL BOSS’S DAY
On Monday, our client CowanGates held a Boss’ Day Brunch in honor of National Boss’ Day. Their support staff threw a thoughtful celebration and provided a delicious-looking spread of food for their dedicated team of attorneys. Nothing says “Thanks for your hard work” like a table full of food. #FoodForThought
I got lots of texts and emails from different team members Monday acknowledging National Boss’s Day, but none of them bought me a new car. #Sheesh
TUESDAY:
PHOTOSHOOT FUN
On Tuesday, Creative Director Art Webb and Senior Graphic Designer Erin Rebmann coasted on down to Chesapeake for a photoshoot. While there, they got to work, snapping shot after shot of different places for our client Chesapeake Economic Development. Here are some behind-the-scenes photos featuring a very happy Art:
This week, I got to spend some quality time with members of my Virginia Council of CEOs Roundtable in beautiful downtown Lynchburg. Lots of great fun, food, and drinks, and I had the opportunity to work on my businesses. They even got a tour of the legendary Texas Inn and delicious grub.


WEDNESDAY:
PRESERVING HISTORY
Our client Fort Monroe Authority was awarded one of the largest grants they have ever received to rehabilitate one of their oldest buildings. They received a $372,437 grant from The National Park Service (NPS) to use toward the rehabilitation of the Building 14 Officer’s Quarters, a 142-year-old historic structure. Check out the full story!
THURSDAY:
THEY SAID YES!
On Thursday, a few of our Madison+Main-iacs spent the day at our client Atlas 42 finalizing their wedding guide. After many months of hard work and great feedback from their end, they were ready to say “I do” to our crew’s work. Keep your eyes out for the final product!

FRIDAY:
YOUR WEEKEND UPDATE
This morning, I gave WRVA listeners my weekend events update on Richmond’s Morning News with John Reid. It’s festival season and there are lots of great events in and around RVA this weekend. ICYMI: here’s the segment.
Also, this morning, Finance & Operations Manager Katie Rossberg and Account Executive Rochelle Sommer hit the road to head to Williamsburg to meet with our client Two Rivers Country Club. On the way down, Katie and Rochelle prepped for their meeting by listening to the new Taylor Swift album for the duration of the ride. (The Madison+Main-iacs love music in the mornings.) Once there, they took a tour of Two Rivers Country Club’s gorgeous waterfront country club and were very tempted to stay for a 9-hole round on their top-rated, Tom Fazio-designed golf course.
A FEW OF OUR FAVORITE EVENTS
Chesapeake Restaurant Week
Chesapeake, VA 23320
October 14-21
Get a taste of the local flavor during Chesapeake Restaurant Week! Chesapeake Economic Development has helped many local businesses get their start or expand their services to the Chesapeake area. Eat at and explore the city’s restaurants starting today!
RVA Bacon Festival
17th Street Market
Richmond, VA 23219
October 23 | 11 a.m. – 3 p.m.
Everything is better with bacon, including your weekend plans! Head out to the RVA Bacon Festival on Sunday and see what’s sizzlin’.
Ghost Walk At Night
Hanover Tavern
13181 Hanover Courthouse Rd.
Hanover, VA 23069
October 24 | 7 – 9 p.m.
Is the Hanover Tavern haunted? Find out for yourself at their Ghost Walk At Night! For only $15, you can tour the Haunted Hanover Tavern, Historic Courthouse, and Old Stone Jail. Guided tours begin at 7 p.m. and the last tour departs at 9 p.m. Get your tickets today!
“Most entrepreneurs fail because they are working IN their business rather than ON their business.” — Michael Gerber