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“5 things I wish someone told me before I became a CEO” With Lora Kellogg of Curious Jane

Drop the idea that you have to be constantly working or grinding to be successful. Embrace the concept that rest, recovery and reflection are essential parts of the progress toward a successful happy life. For more than 10 years now, I have rented a condo on the beach with my family for the entire month […]

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Drop the idea that you have to be constantly working or grinding to be successful. Embrace the concept that rest, recovery and reflection are essential parts of the progress toward a successful happy life. For more than 10 years now, I have rented a condo on the beach with my family for the entire month of July. Everyone in the agency knows I’ll be working remotely in July. I come back rested and full of ideas, and I will never regret the time I spend with my family and friends.


As a part of our series about strong women leaders, I had the pleasure of interviewing Lora Kellogg, CFE. Lora is the president and CEO of Curious Jane, an ad agency specializing in franchise marketing. A frequent contributor on franchise trends in such publications as Forbes, Entrepreneur, Franchise Times, Franchising USA and Brand Quarterly, she was named by Entrepreneur as one of “16 Businesswomen Who Can Be Counted on to Provide Their Own Seat at The Table.” With a natural curiosity about how to elevate franchise brands in a rapidly changing market, Lora and her team make it their mission to help franchises grow and entrepreneurs succeed. She is an entrepreneur herself and is currently working on a book about entrepreneurship. Lora is on the Forbes Agency Council and is an active member of IFA (International Franchise Association).


Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

I originally thought I wanted to be an English teacher because I loved to write, but when I had to create my first bulletin board as part of my grade, I hated it. I am creative but not crafty, so I knew pretty quickly I needed to change my major. I had been awarded a full scholarship to be a teacher, so I had to pay all the money back. I paid the entire amount off my first three years working in marketing.

Can you share the most interesting story that happened to you since you began leading your company?

I was at the beach one summer thinking about how our agency could grow and what we needed to do to take it to the next level. At the time, about 50% of our business was healthcare clients and 50% were franchise clients. I decided it was time to put our stake in the ground and choose to specialize in one vertical so we could truly be the best at what we did. After going back and forth, many ups and downs and some trial and error, we picked franchise marketing, and we committed 100% of our efforts to building our brand. That meant eventually losing 50% of our business, which was millions of dollars, to gain new work with franchises. Our specialization and our brand took off, and now we represent some of the biggest franchise brands in the industry and absolutely love the lane we chose. In fact, our mission and the reason we exist is to “help franchises grow and entrepreneurs succeed.” It’s a mission our employees really believe in and get excited about. This year, we were listed by Entrepreneur as one of the top franchise marketing agencies in the United States. This taught me to not be afraid to change and after you decide which way you want to go, to give it all you’ve got.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Only a few years after I started the agency, we designed an ad to run in a small Caribbean newspaper for one of our clients. They printed the newspaper and then told us that one of their employees called the number on the ad and found out it was incorrect. Instead of calling the brand we were working with, it was a porn number. We had transposed a number. We had to pay almost $10,000 to reprint that section of the paper. Now we have at least three to four editors on staff to ensure something like that never happens again.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CEO or executive that most attracted you to it?

I’ve always been a leader and loved a challenge. What attracted me to be a CEO was having the ability to work with highly intelligent people. In fact, my business coach asked me to name the top five people I wanted to surround myself with in the coming year to help myself grow. I named four, then told him the fifth was “my leadership team at work.” They make me better.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

As John Maxwell says, everyone can be a leader because leadership is influence. I think the difference between a CEO and other leaders is that a CEO should be influencing but she must also hold herself and her team accountable to a very high standard. The final decisions, direction, vision and lifeblood of the company is ultimately the responsibility of the CEO.

What is the one thing that you enjoy most about being an executive?

I love working with, mentoring and coaching others to be better leaders, to be strong, to handle pressure and to use their leadership to influence others for good.

What are the downsides of being an executive?

It’s a lot of weight on your shoulders at times, and you have to really learn how to be decisive and handle pressure when life brings you unknowns and curve balls. And with many decisions you make, you won’t be very popular. You have to be OK with that.

What are the “myths” that you would like to dispel about being a CEO . Can you explain what you mean?

I think there’s a myth that CEOs have it together all the time — that we’re strong, we don’t worry and we don’t let things get to us. I had one of our directors who has been struggling with juggling her load and handling the pressure ask me how I handled so much pressure. I told her: “I have a sign by my bed that says, ‘Give it to God and go to bed.’ I used to wake up at 3 a.m. on the dot every night worrying about something. I would go through every ‘what-if’ possible as it related to the company, my life, my kids, etc. I have learned that there are some things we can control in our lives and many others we cannot. So each night I try to give those things to God and go to bed with peace and start over the next day with a clear mind.”

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

I think women executives put more guilt and pressure on themselves than men do. We are executives, moms, sisters, friends and daughters, and we’re trying to make time for everyone and everything. We think we are supposed to hustle, grind, learn, advance, pick up kids, work out, cook healthy food and be fully present with those we love. But often what we do is wear ourselves out and set an unrealistic expectation of ourselves to be superwomen. We need to loosen the reins some on how hard we are on ourselves and learn to enjoy and appreciate the season we are in.

What is the most striking difference between your actual job and how you thought the job would be?

I think I pictured my job more on the work side, looking at numbers and P&Ls and balance sheets, which of course I do, but much more of my job is on the people side, with employees and customers.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive, and what type of person should avoid aspiring to be an executive?

I think drive and actually wanting it has a lot to do with it. I know people who are very content being a leader and influencing others who don’t want the responsibility of being an executive and the pressures and responsibility it brings. One of the hardest days in my career was when I bypassed an employee for a VP position, but I knew ultimately, she would be more content and good at her role as a director than she would in the VP role. She was devastated and very upset with me. But now this person has been with me for more than 15 years and she understands why I did what I did and is much happier in the role she’s in.

What advice would you give to other female leaders to help their team to thrive?

I think more females need to have confidence and quit second-guessing themselves. I wish I could give shots of courage and confidence juice to many women I know, because I know that when they are confident and on their best game, they can help the teams around them thrive even more. There are brilliant, amazing women who need to believe what others see in them. I think female leaders also need to realize they don’t have to prove to anyone that they can do it all. They need to trust their teams and delegate everything they can so they can focus on higher level things.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My junior year of college I had the privilege to intern for Tom Morris at the corporate office of a hardware chain called Scotty’s in Florida. Tom was the former head of marketing for Sears for the U.S. and Canada. He took me under his wing and let me go to every meeting with him, and I’m confident I learned more from him that summer than I did in all four years of college. He hired me my senior year and three years later, he fired the advertising director and put me over the entire Advertising Department. I remember the day vividly, because it was April 1 (April Fool’s Day), and I was 23, and he announced to everyone that I was the new advertising director and I was over the entire department. I was scared to death, and I honestly wasn’t prepared to lead that big of a department, but he believed in me and helped me every step of the way. I figured things out quickly and over the next 10 years became the first female vice president in the company’s 75-year history. When my son turned 2, I went to Tom to see if I could work part-time because I wanted to start my own marketing company, and he let me. More than 15 years later, my agency is bigger and better than ever. I owe much of the success of my agency and my professional growth today to how he mentored and groomed me. We are still great friends.

How have you used your success to make the world a better place?

I think my biggest contribution to the world is to be an encourager and mentor to others. I believe in having real authentic connections with our employees and with our customers. I hope in some way people see love, faith and kindness in me, in the way I run my business and in the way I treat people.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. If you want to make everyone happy, don’t be a leader. Sell ice cream. I had to learn early on that if I was going to be a leader, I could not be a people-pleaser.
  2. Be careful of who you listen to in your life. Carefully pick three or four people in your life who will tell you the truth and hold you accountable. Don’t ask 10 people what they think about things. Be able to make decisions and be decisive, and when you do need guidance or a “gut check,” have some solid strong people in your life that you admire and respect, and then listen to them when they give you advice.
  3. Drop the idea that you have to be constantly working or grinding to be successful. Embrace the concept that rest, recovery and reflection are essential parts of the progress toward a successful happy life. For more than 10 years now, I have rented a condo on the beach with my family for the entire month of July. Everyone in the agency knows I’ll be working remotely in July. I come back rested and full of ideas, and I will never regret the time I spend with my family and friends.
  4. Talk less and listen more. I am naturally a talker, so I’m continually refining and realizing that I need to listen more. I think as leaders we need to ask clarifying questions before we’re so quick to give our opinions.
  5. I wish someone had challenged me and asked me what my definition of success was. I think so many people want to job-hop and get raises and move up and be promoted, but they really don’t even know or haven’t defined what they want to do and what success truly means to them. Many people think of success in terms of money and advancement, but it’s also about happiness and contentment and living out their own individual, authentic life.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I would encourage everyone to find people you can mentor. The more we can give back to others and help other people succeed, the better the world will be. The business world needs more people who are willing to invest in others’ success with no ulterior motive.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life? “Be the change that you wish to see in the world.” — Mahatma Gandhi

This really reflects my commitment to mentor and encourage others. I appreciate my mentors so much and I believe everyone needs that sort of guidance and encouragement to reach their full potential.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to have breakfast or lunch with Dina Dwyer-Owens with Neighborly, a service-based franchise company. I’ve been watching and reading about her career and life for years and think she’s an incredible leader and inspiration to so many women. I remember watching her on the hit show “Undercover Boss” and thinking that she is someone I would love to meet one day. Plus, I think she lives in Waco, Texas, so maybe we could also ask Joanna Gaines to join our party. Go big or go home, right?

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


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