Following is part three of an interview with Cheryl Benton, owner of 747 Marketing. Their website says, "We've built a consulting business that helps our clients gain unfair competitive advantages by outwitting the other guys." Visit Cheryl Benton’s website simply by Googling 747 Marketing.

Q. In 2005, you launched The Three Tomatoes free e-newsletter. What gave you the inspiration for The Three Tomatoes?
A. That came from marketing. I looked around and realized that advertisers, marketers and the media were pretty much ignoring people over 45. And, in particular, they were ignoring many women working in New York City -- which I call the land of size 0's and smart thinking twenty- and thirty-somethings.

I was thinking, "We're starting to feel like the invisible women." Then, looking around, I had so many great friends who are very accomplished women -- successful in their lives, and successful in their careers. They still look great, they have great disposable incomes. And, they're the people who actually get to go out and spend money on a lot of things.

I thought, "This is silly that no one is talking to us." So, I had this idea for this newsletter that I call The Three Tomatoes. It has a very New York City edge to it, in terms of voice and content. But, it's beginning to gain a lot more appeal across the country, which is really interesting. I had the idea, and I thought, "This will be fun, I'm just going to see what happens."

I love interactive marketing -- watching how things virally happen. So, it started as a weekly e-mail newsletter to 60 friends, and today we have over 3,000 subscribers. And, it's starting to grow exponentially. The website was initially there to house the archives, and to be a place for people to sign up for the newsletter. But, we're starting to build some more content.

In the last year it has started to grow, we're getting more media attention, and we started to create some events around this. And, I love doing that. It's my passion -- it's such a fun thing to do.

Then I realized, "If I was going to be really serious about The Three Tomatoes, I should start to treat this like a real client." So, it has become my number one client. You talked about putting in all the hours -- I put an enormous amount of time into this. But, I can do it anywhere. Today happens to be a miserable rainy day, so I'll do this today instead of doing something fun.

Now, I'm in the process of looking at revenue models, and I'm seeing what kind of potential this really has. And, that has been great fun, and terrific.

Q. Your website is aimed at "fabulous ladies in the prime of their lives." What pressures does a lady encounter?
A. Often, if you have careers in advertising, entertainment, or whatnot, you're starting to feel the pressures of youth orientation. Somehow, you become irrelevant. Ironically, this is a great time for you to leverage all your experiences. And, it's a more interesting time in your life. We're more interesting people, because we've learned a lot of interesting stuff along the way.

The women I know are at the pinnacles of their careers. Or, they're trying to make that next transition, and say, "What do I want to do next, and how do I want to make that happen?" And, they have a better understanding of what is important and what isn't.

The Three Tomatoes is about fun and irreverence, and really celebrating women at this stage of our lives.

Q. When people talk with you about making a transition, what are their concerns?
A. For a lot of people who have had successful careers, they become their careers. We all know that syndrome: "We are what we do." And, it gets a little scary. There are times we've all been caught up in that. So, we start to think, "OK, if I'm not doing this any more," or, "I don't have this title, or these kinds of perks, then who am I?" That's tough -- that's probably the biggest hurdle. You start to say, "OK, what next?" It takes thinking. And a lot of people have no idea. Then, something will happen. Either they'll be forced out of a situation, or they do that willingly. Then, they ask, "Now what?" And that is scary.

Think about it. You're not going to be in your current job forever. What are the things you love? What are you passionate about? Be successful in something you love. Maybe you want to get involved as a volunteer. Sit back and think, "What do I like, what makes me happy, what are my interests, and where are my passions?" Then, follow all that into whatever the next thing is.

Q. What are the signs that a person should transition -- that the person should go for something new?
A. When everyone around you is 30 years younger! (Laughs.) No, not necessarily. It's really fun being around young people.

I think it's when you're so caught up that you don't have a life. You look at yourself and say, "I've totally lost sight of anything except what this job is, and I'm working 80 hours a week." I know people like this -- they don't take vacations. If they do take a vacation they're constantly checking their Blackberry. There's no downtime, there's no relaxation time. They're so caught up in this thing they are doing, it becomes who they are. When you are at that point, it's time to say, "I need to look at my life today. What am I about?"

Q. Do people need to find more balance with family time?
A. We did a survey in The Three Tomatoes. We asked, "Looking back, would you have spent more time on your career, your family and relationships, or yourself?" The answer was, "More time on myself." The lowest one was, "My career." There's a positive here, because at this stage of life, the person can feel, "Now I can spend more time on myself. I've always wanted to write." Or, "I've always wanted to work with children."

Q. Why don't women spend enough time on themselves?
A. Probably, because they've been very focused on other people -- either on their careers and/or their families and relationships. But, this is a great time to explore who you are, and what you want to do.

Q. How can a person make a successful transition?
A. It's a process. It's sitting down and re-figuring who you are, where you want to be at this phase in your life, and where you want to go -- with all the talent and wisdom you've accumulated over the years. Ask yourself, what do you want to do with that next? For most of us Boomers, it's not playing golf seven days a week. We're different than our parents' generation in that regard. They did retire. We're much more do-er. We're active and adventuresome.

Q. A person says to you, "I have big fears about my future." You should say to this person…
A. Yes, change is scary. That's what I would say. Change is scary. What are the things that scare you about that? Make a list of them. For some people it's, "I'm scared about financial security." Or, "I'm scared I'll get sick." Realize that there are things you can control and things you can't.

I've always found, in any situation, it helps to say, "Here are the pluses and minuses. And, what is the worst thing that can happen?" Put that on the table and get over that. But, being scared is a normal thing. I would say, "Of course you're scared. You're doing something new, you're stepping off the cliff and you're not going to know all of the answers."

I have a vision of where I want things to go, but you have to be flexible. You have to figure it out as you go along. For example, if you've left some fabulous career, you may start out and say, "This is what I think I want to do." Then, you spend the next year trying to do that thing and you find out that isn't at all what you want to do. I think the answer is being flexible and being open to trying new things and figuring out what works best for you. I would say it's anti-methodical thinking -- getting over fears, making a list and becoming less scared about it. Look forward to challenges.

Everyone is trying to figure it out. We're all trying to do it in different ways. I've always been an optimist. I've always been willing to jump off a cliff and try it. What is the worst thing that can happen? In most situations, the worst thing isn't that awful. So, try new things.

Q. Did you have times where you thought, "I'm going to need to make a transition."
A. My transitions have evolved. I've made a lot of transitions, like we all have, to get to different phases in my life. It's an evolutionary thing. The difference with people who transition more successfully than some other people: The other people are ignoring that little inner voice -- they aren't dealing with it. Then, they get to the point where they're forced to make a transition. Then, it does seem like the bolt of lightning came down, and they think, "Now what?"

The successful people listen to that voice a little more. You think, "In two years I want to do XYZ." Or, it's done on a more subconscious level. Like with The Three Tomatoes: That was rolling around in my brain for a year and one day it took force. Then, I thought, "Let's do it and see what happens."

During that rolling around time, I was seeing my friends. I saw places to go and different concepts. You hear yourself talk, maybe about that great little shop, and that evolved into other things that are interesting. Now, every week, the newsletter is a conversation with friends.

Author's Bio: 

James O. Armstrong, who serves as Editor and President of,, which is The Resource for Job Transitions over 40, also wrote "Now What: Discovering Your New Life and Career after 50." In addition, he is the Cofounder with his wife of Armstrong Solutions Inc.,, which is a Counseling, Coaching and Career Management Practice with a reduced fee schedule to expand their services to a larger group of men and women with needs. Armstrong also serves as President of James Armstrong & Associates, Inc., which is a national and international media representation firm serving Central US and Canada out of his Suburban Chicago base.