– By: Greg Brown,

I was substitute teaching, because there was such a glut of English teachers. I was there until the end of the school year, and I thought, “I’ll have to go back to substituting in the fall.” I thought, “I’ll get some kind of summer job.” But, if you told businesses you were going back to teaching in the fall, they wouldn’t pay anything.

So, I thought, “The next place I go, I’ll act like I’ll stay here forever.” And, that turned out to be a 10 year summer job in a technology firm. I got into advertising there. I became the Ad Director, and then the Marketing Director. After 10 years, I left there and started my own ad agency on Long Island. I had that for 10 years, and it was acquired.

Q. What made you decide to start your own agency?
A. I was on the client side, and we were working with agencies. I was at a point where I wanted to try the agency side. It would be more interesting and challenging. And, ironically, people were saying, “Even though you’ve been a marketing person for 10 years, you haven’t had experience on the agency side.”

So, I was finding that the agency door was tough. At that time, some of the big agencies had training programs, but my time for that had long since gone by. I thought, “At this point, I don’t want to start all over in my career.” So, I said, “I’m going to start my own agency and figure it out along the way.”

Q. Did you find it fairly easy to pick things up, or was it challenging, or stressful?
A. Yes, all of the above. Whenever you’re starting something new — and especially when you’re going from something very secure — all of a sudden, you take this giant leap into uncharted waters. This is particularly true when it’s an entrepreneurial project. But, there’s a lot of adrenaline, and you have to believe you can do it.

My first client was the firm I was working for, and then I had a couple of clients. That was terrific, because they all believed enough in me to allow me to do that. They were enormously helpful.

I learned, and part of growing and doing anything is making mistakes. And, saying, “OK, what did I learn from that?” Then, you pick up and move ahead.

For example, when you’re starting up something, any client who came your way, you say, “Oh, I can do that,” or, “I’ll take that on.” Then, you start to realize that you have to focus your effort more.

I found that it took as much time, if not more time, to handle a very small client with a very tiny budget, than it did to pursue clients with bigger budgets. That was a big lesson: When to say no, and when to say, “OK, I’m not going to say yes to this kind of client — even if it would provide some short-term income. I need to focus on the bigger things that will ultimately be more beneficial.”

Q. You’ve worked in Manhattan most of your career. What strengths are required to succeed in this competitive environment?
A. You’ve got to be willing to accept failures, pick yourself up, dust yourself off, and start over again. In Manhattan or Boise, if you love what you do, and you keep at it, you will succeed.

Q. The Manhattan work world has changed since you started. Tell us a change that affected you, and how you adapted.
A. Now, with computers and the Blackberry, it’s the total commingling of your business and personal life. You’re always on 24/7 call, even on vacation. You’re getting off a plane and checking your Blackberry.

And, there’s a good and bad side to that. The good side is: You can work remotely and you can handle certain business things a lot easier than you could 20 years ago, when you had to physically be in the office to do something. The downside is: You’re never free! (Laughs.)

Q. You’ve been active in many associations and groups. Did they help you with transitions?
A. Yes, it’s been great to be in them. I’ve been involved in advertising industry associations. They’ve been great for a number of reasons. Early on in your career it’s fantastic because you can reach out to other people. It expands your network. I’ve been in the B/PAA (Business and Professional Advertising Association) and the BMA (Business Marketing Association). Some of my very closest friends are from those organizations. We’re friends to this day.

You find you have a nationwide network. And that is so critical because when you’re ready to do something new, you sit down and say, “Who is in my network?” I would say to anyone at any stage: Get involved with groups in your industry. In your younger days you’re taking from those groups. And, when you get more experienced in whatever you do, you will give back to those groups.

Q. You continue to have a very successful career. To you, what is career success?
A. I think it’s loving what you’re doing. I’ve always felt very fortunate that I’ve always loved what I was getting paid to do. I always loved advertising, I loved marketing, and I love what I do now at The Three Tomatoes Newsletter, http://www.thethreetomatoes.com.

I think that’s the key to anyone’s success. I think you would be hard pressed to find anyone who has been successful in an endeavor who has hated what they do. It doesn’t mean every day you get up saying, “Oh, my gosh, this is great.” Obviously, there are lots of days you get up and say, “Oh, gosh, I have to face this client or that challenge.” But overall, it was loving the business I was in, and the people in that business, and feeling that adrenaline. And yes, I loved doing that.

Q. What’s next for you?
A. Who knows! (Laughs.) I have no idea. I love The Three Tomatoes. That’s the thing I’m having the most fun with these days. I’m spending a lot of time on it, and we’ll see where that takes me.

I started out teaching, so kids and education have always been very important to me. So, I’ve become very involved with a couple of non-profit groups that work with New York kids and education. That has fulfilled that other piece of me. And, that goes back to figuring out what has been important to you all along. Look at what you are passionate about.


Part 2: How 747 Marketing Took Off

Q. In 2004, you launched a firm called 747 Marketing, http://www.747marketing.com. Did you identify a market need that inspired you to start this firm?
A. Yes, the marketing need was my own. (Laughs.) I was at a point where I needed to have more flexibility. I needed a lot more time and a lot more control over when, where and how I wanted to work and the kinds of assignments that I would find challenging. It was really my own personal need to do that.

The decision to do this was more of a lifestyle issue. So, I have to always remind myself why I did that, so I’m not back into the 80 hour work thing again. Now, I look at projects — at the scope of them, and how long term they are — and I see how much of a commitment I’m willing to give before I’ll say, “Yes, I’ll do that.”

How do you find projects that won’t be so time consuming? It’s tough. It’s looking at the scope of the effort and asking, “What is this going to be,” at the beginning of the project. You move on in life and you use your experience, your wisdom, and maybe your past connections, in order to make wise decisions. You don’t want to be put on this 80 hour treadmill, which is the game that gets played when you’re in your 20s.

When I get into a consulting project, I base the project on how much time is required and what is the timeframe. For example, if it’s a three month assignment, I might say, “OK, I will devote two days a week of my time to this project.” And, I set that up. I think a lot of it is setting up that expectation in advance. You have to do that, particularly when you’re consulting. Otherwise, you end up making 50 cents an hour. It’s not worth doing that. Setting it up right isn’t perfect, but you have to go into it with that kind of discipline.

I’ve turned down projects because of the time commitments involved. They would have been very intense timeframe projects.

Also, when you’re working as a consultant (and people are paying you as a consultant) and they do know you are on that clock, I find it’s easier for them to become more disciplined because they realize there is a clock. But, we all want to help and I am flexible.

I do a lot of seminars with the ANA (Association of National Advertisers). One of the seminars I teach frequently across the country to clients is called, “The Client-Agency Relationship.” I spend a lot of time talking about how to be a good client and how to manage expectations.

Q. Did your work experience cause you to structure 747 Marketing, http://www.747marketing, differently?
A. It’s different in that it is truly consulting. I started an agency that was full service. And then of course for many years I managed in full service agencies, where you actually have products you produce: It’s an ad, or it’s a brochure.

My particular talent and the things I really liked doing, were on the strategic side of the business. I helped people to be better, smarter marketers. “Here is the issue. Let’s come up with a solution.” I realized that is the piece of the business, where I wanted to focus. When we get to the point where the client needs other services or other people, we help the client find those professionals.

Q. Tell us about a time where you had to move a client to a new way of thinking.
A. I was very fortunate in the 1990s. I was with an agency and it was probably the first agency that became involved with the Internet and interactive marketing in a big way. I was working with some very large clients who only had used traditional media. I was helping those big consumer companies figure out what the interactive world was going to be like for them. That was a huge leap in the late 1990s and, for a lot of companies, it’s still a big leap.

Q. What types of challenges did it take to move people into electronic marketing?
A. In the consumer world during the 1990s, the 30 second TV commercial was still king. But, the Internet was starting to change it and cable was changing it. So, the smarter, consumer marketers realized they had to at least experiment in some different spaces to see where this whole new Internet thing was going. And, the ones who got in early are doing it really well and others are playing a catch-up game.

Some of the companies stepped into the waters pretty early. They were starting to go from a world where their consumers were mass consumers to beginning to understand that there were opportunities to build relationships with different kinds of intimate target audiences. And, it takes time to figure out how to do that and how to turn some of these big ships around.

Other companies finally said, “Oh gosh, we need to do this. We can jump into this tomorrow and we’ll have this all figured out in a year.” But, it doesn’t work that way. So, yes, there were still people, who were fighting the new media, and not just on the client side. There were people who wanted to produce a 30 second, big budget TV commercial on the agency side.

Q. Why did people want to do that rather than create a web page?
A. I think it’s fear of change. It’s fear of the unknown. We’re all comfortable with what we know and what we like and for some people and organizations, it’s harder to identify and accept what you’re going to bring to it.

Q. Why are you different from those people?
A. I’m an entrepreneur at heart. For some people, it’s in your DNA so, you’re less afraid. I’ve always been curious about new things and I’ve always loved technology. I spent 10 years initially in a technology company. Not that I’m an in-depth technology person, but I’ve always liked what technology can do for us. Curiosity is a lot of it.

Q. How do you convince a resistant person to change?
A. I think it’s doing something in a small way. It’s saying, “Don’t give me your entire budget, but let’s try something small here. Let’s put a little bit of money into it, let’s try it and we’ll see what happens.” That gives people a comfort zone. They don’t feel like they’re rolling the dice on one big bet.

Q. Does this require an investment on the agency side?
A. Sure, because there’s a lot of education that has to go on, if you’re trying to get people to do something. You’re investing that this thing is going to work and there will be more money to follow.

Q. Is it difficult to get a commitment from the agency leadership?
A. It depends on the organization. If you don’t have that kind of support upwards, I suggest to people not to do it because if you can’t at least get the initial buy-in — “OK, we’re willing to experiment here” — your chances aren’t good later.

But, if you don’t change in the world, you’re going to become a dinosaur. There were agencies that didn’t change at all and they went by the wayside.


Part 3: The Three Tomatoes Grew in Manhattan

Q. In 2005, you launched The Three Tomatoes free e-newsletter, http://www.thethreetomatoes.com. 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, http://www.thethreetomatoes.com, 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.

Greg Brown is with NowWhatJobs.net, Inc. http://www.nowwhatjobs.net NowWhatJobs.net is the resource for job transitions after age 40. It provides information about companies and other organizations, colleges, continuing education, franchises and relocation options. NowWhatJobs.net, http://www.nowwhatjobs.net, also provides opinions that Baby Boomer & Active Senior men and women will want to check out.

By Rosie

I am a blogging boomer who wants to promote and provide all things boomer.