"Come to me, all you who are weary and burdened, and I will give you rest” (Matthew 11:28).

Hello! My name is Elise Gallagher and I’m the co-founder and president of Catholic Women in Business. A few weekends ago, I shared that I took my first “CEO Day,” and because several women showed interest, I thought I’d share more with the CWIB community!

The Inspiration

Over the last few years, I’ve dreamed of taking a CEO Day. I first heard about the concept from Tim Ferris’s book, “Tribe of Mentors.” Many of the entrepreneurs interviewed in the book take a day or weekend to themselves each quarter (some even take time each month) to review their company’s priorities, sit with the last quarter’s analytics and financials, and plan for the following quarter. Even more so, they use this time to step away from the company’s day-to-day operations and give themselves the space to dream of “what could be” for their company.

I currently own two companies: RINGLET and Catholic Women in Business. To say 2020 was a difficult year for small businesses would be an understatement. I found myself on Jan. 1, 2021, feeling completely drained and uninspired. Although I had enjoyed holiday time with my immediate family, I still hadn’t had the time to step back from the hustle and bustle of end-of-year responsibilities and plans. I knew that it was finally time to invest in a CEO Day. It was on the first day of the year that I booked myself a room for one night in a hotel room in Annapolis, Maryland, in mid-January. I was excited, and a bit nervous, to jump into a whole 24 hours devoted to my companies.

Weekend Agenda

Going into the weekend, I was aware that I only had 24 hours, so I took some time in the week leading up to my CEO Day to plan out how I was going to spend my time. I know I wanted to do four things: pray, journal, reflect, and ideate. Driving down to Annapolis (I only live 30 minutes away), I still wasn’t 100% sure about the weekend’s agenda. Here is how the weekend shaped up:

Saturday:

1 p.m.: Arrived at the hotel

2 p.m.: Prayed a rosary, then journaled

3 p.m.: Sat (alone and distanced!) at a coffee shop to “brain dump” into this Hatch notebook

5 p.m.: Attended Mass

6 p.m.: Ate dinner

7 p.m.: Did bit more journaling, then it was a movie and early bed time for this pregnant mama

Sunday:

8 a.m.: Ate breakfast and took a walk around town

9 a.m.: Did some more organizing in the Hatch notebook

10 a.m.: Created a calendar outlook for the year

11 a.m.: Checked out of the hotel and headed home

Takeaways

There were a couple of key takeaways that I learned from my first CEO Day. Firstly, I would have ideally had more time. Being seven months pregnant, in the middle of a pandemic, and on a limited budget, I could only get away for 24 hours. However, in the future, I’d like to extend CEO Day into a whole weekend. This approach would definitely give me more time for brainstorming and creativity, and I would love to add a museum trip, time for sketching or water color painting, or some sort of art or craft activity into the agenda next time.

Secondly, having the right tools for your CEO Day is crucial. I used several books, including: my agenda and calendar for the year, my personal journal, and the Hatch notebook. I bought the Hatch notebook just for the occasion, and it was amazing. The notebook walks you through the process of organizing ideas from conception to planning projects. I found it helpful in creating timelines and a tangible plan for each of my ideas for RINGLET and CWIB for the year. I walked away with a clear understanding of the next steps to make these dreams a possibility (although 2020 reminded us that being flexible and ready for change is necessary in business!).

Lastly, prayer was an integral part of making my time away successful. It was refreshing to have an opportunity to offer my businesses to the Lord, ask for His guidance, and have dedicated time to hear His answers. I loved having time to pray for my teams, my clients, and our efforts for the year.

I would love to have a CEO Day every quarter! I’m not sure if I’ll be able to get away every couple of months, but blocking time off to have a change of scenery and get away for a weekend is definitely an annual goal.

Have you done a CEO Day yourself? Have you found it helpful? Are you planning one for 2021? Comment in our Facebook group to let us know!

Elise Crawford Gallagher, co-founder and co-president of Catholic Women in Business, is the founder and CEO of RINGLET, a digital marketing and brand management agency that works with women business owners in the Washington DC area. Elise graduated with a master’s in communication from Johns Hopkins University. She worked in the Catholic non-profit world before starting RINGLET. Her concentrations were in public and media relations and digital communications. She currently lives in Maryland with her college-sweetheart-turned-husband, who is a high school theology teacher and law student.