Speed Bump In The Fast Lane (a career story)

My career journey starts with pure serendipity.

My father, who worked for IBM his whole career, became aware of the Johnson O'Connor Research Foundation, which gave people a battery of aptitude tests that have been mapped against career satisfaction. Once they assessed your aptitudes they recommended careers that fit best. My father loved this approach. I was in high school and he arranged for me to take the aptitude tests. One of the best-fitting career paths recommended for me was advertising.

At the time I was running the golf pro shop of a country club. As serendipity would have it, one of the members who had an advertising firm liked what he saw in me and he offered me an internship. I jumped at that, and worked there all the way through college. He happened to work in a field of advertising called direct response, which asks the customer to take an action—for example, to send in a reply card. I loved not just the creative side of that approach but also the measurability of it. Based on the responses, you knew if the ad worked.

Being offered an internship in none other than advertising—yes, that was pure chance. So was the good fortune of being born into a wealthy community and attending some of the best public schools in the country.

But truth be told, I also made my luck. I was a hard worker and a high achiever from way back.

As a Girl Scout I set my sights on earning every badge available and was the only one in my troop to do so. I had a paper-delivery route, I babysat, I was a mother's helper. I worked as a cashier in a grocery store, I scooped ice cream at Baskin Robbins. I also excelled academically, won fistfuls of awards, and graduated co-valedictorian of my high school class.

I was probably born motivated but I was also influenced by my parents, my father especially. My father was my idol. He was a fighter pilot in the Marines. He got his undergraduate degree at Cornell in the electrical engineering program, which was very demanding, and he went on to get an MBA and CFA. He was also my mentor. He still mentors me even though he has been dead for 16 years.

But I could never have foreseen that the very qualities and mentality that made me a high achiever would come back to haunt me later. I would only come to learn that, as I travelled the arc of my career.

Like my dad, I too went to Cornell, where I was able to design my own major—on the influence of language on thought. I took courses in communication, psychology, sociology and linguistics. All of that turned out to be great fodder for a career in advertising.

After graduating, I sent my resume to the top ten direct-response firms. I included a reply card along with a self-addressed stamped envelope. Only one sent back my card. I went in for an interview with that firm, and I was hired on the spot.

They made me an assistant account executive, initially working with just one client. I had to understand each client's business well enough to come up with an advertising strategy. Once that was in place, it fell to me to bring together a constellation of expertise—copywriting, art direction, ad production, media planning, results-tracking, and more—to produce ads. I didn't realize it at that time but, in effect, I was a general manager, someone who led people in a variety of disciplines. That turned out to be my core skill.

My first day on that job I was at my desk promptly at 8:00 a.m., having taken the train into New York City, and I didn't get home until midnight.  I kept that up, and that meant I didn't have much time for anything else in my life, but at that stage that was just fine with me. The achiever in me was in heaven.

Soon I was responsible for multiple clients. I loved the variety. But after a couple of years, I had a level of dissatisfaction. I was restless. An ad agency gets to work on just a sliver of the client's business. I wanted more influence on a business than that. Heck, I wanted to be the one that hires the advertising agency!

As it turned out, one of my clients, Time Life Books, a division of Time Warner, came along at that time and offered me an opportunity to do just that, to go inside. My job was to market their books, series of books, as many as 20 volumes in a series, on subjects like "The Old West," "Home Repair," and "Mysteries of the Unknown." Each book in the series was sold one at a time—using none other than direct-response advertising. Which is why they wanted me.

Indeed now I was the one who hired the ad agency. But that was just the start. I had to come up with the advertising campaign for each book series and then mount the campaign. That meant learning to work with functions new to me like product design, production, warehousing and logistics, and telemarketing. If the campaign flopped, it was on me. I loved it, every bit of it!

Before I outgrew that job, I was promoted to marketing director of a new function, new product development. It was my job to generate ideas for new books and to pilot those ideas. That was wonderfully exciting. But then it wasn't.

I applied for a job at Disney, a fast-growing company I admired, but I didn't get the job. The hiring manager told me I had a fantastic resume but she chose the candidate with an MBA. That did it. I enrolled in an MBA program, which gave me the theory and science behind what I had learned from experience.

In the meantime, Amazon had appeared on the scene. I thought to myself, gamechanger! At the time, Amazon was selling books but on that platform they could easily sell other things. The possibilities seemed limitless. And I was working for a business, Time Life Books, that didn't even have a website. A dinosaur in the making, I said to myself, I'm getting out.

Right down the road from where I worked was none other than an internet start-up, America Online (AOL). At the time AOL was the only game in town. If a company wanted to operate on the internet, AOL was their only option. The deals were big, each on the order of $50-$100 million. They were looking for a direct-marketing person; I applied and got the job.

I ended up owning a portfolio of web channels—the travel channel, the music channel, the computing channel, the games channel—and my job was to make sure the channels had enough traffic. Again, I was responsible for various disciplines, all new to me: web-product development, html coding, marketing and content creation. The metrics were new too: "pageviews," "eyeballs on a page," "ad units." Oh, the variety!

In my heady seven years at AOL, it grew from five million to 38 million members. What a wild ride!

Then, of all things, AOL acquired Time Warner. New media swallowed old media! Because I knew both companies, I was selected for the integration team, assigned the unlikely task of bringing those two wildly different worlds together. From the very start, you could cut the tension with a knife. AOL took the attitude, we have you over the barrel. Time Warner, for its part, never felt it was paid what it was worth. Time Warner had chosen to be paid entirely in AOL's stock, no cash, and almost as soon as the deal closed AOL's market position was weakened by competitors—its revenue forecast dropped and so did its stock price.

I remember very clearly driving to work one day, and it hit me: I didn't want to go to work! I'd never felt that way before. It wasn't just the unpromising merger. I had pressing personal reasons to take a break from work period. My daughter, a juvenile diabetic, was 13 and needed more of my support, and my dad at 65 was dying of cancer. I was free financially to take a break thanks to stock options I had been granted by AOL.

I was also going through something of a mid-career crisis. I had just turned 40 and suddenly climbing the corporate ladder didn't excite me anymore. I found myself wanting to do something more meaningful, something that would make more of a difference—a chance to give back. I'd also always strongly believed that "when much is given, much is expected."

It was no accident, then, that I chose a place--Big Brothers Big Sisters (BBBS)—that served the under-served. From a young age I could sense when someone was sad. I always felt for people who were bullied or lacked confidence, or who I could see were marginalized. I wanted to comfort them and make them feel better.

I had grown up in the wealthiest county in the United States and it was also the county with some of the greatest inequities in the country. I don't know why but from an early age I could see that inequity, that injustice. It seems I was born with eyes of empathy and a heart of compassion. In my earliest thinking and my earliest politics I was a "progressive."

It also turns out that I myself was an "other." In college, I clued in to the fact that I am gay. Perhaps the knowledge that I was "different" was always in me and it helped me even more to feel for others who were also different.

I was so fortunate to wind up at BBBS. It's a unique nonprofit: it enables the service but it doesn't directly provide the service. Instead, BBBS recruits, screens and trains adult volunteers then connects them with the right children who can benefit from a mentoring relationship, and then it supports those mentoring relationships over time. It's a sophisticated service delivery model that in this sense was corporate and well-suited to me. I often thought we at BBBS could just as easily be managing the production of cars as mentoring relationships.

I had the good fortune to start out as the head of service delivery, which meant I got to see the service model in action and learn the difference between managing in the nonprofit versus private sector.

At Big Brothers Big Sisters, I had to again learn an entirely new industry. I had never worked in a community-based human services organization. I had to learn to "start with the mission" when I engaged with staff because they are driven not so much by hitting certain targets than by making a difference in people's lives. I had to learn how to be an effective CEO, how to work with a Board of Directors, how to be an effective fundraiser, how to be the "face of the organization," how to engage with the media.

Coming in, I was told that perhaps the CEO, who'd been in that role for twenty-four years, would retire in five to six years. But I didn't plan to be there for that long so it didn't matter. Then the Great Recession of 2007-2008 hit, and the CEO retired. The board contacted me while I was on vacation in Switzerland, asking me to come back earlier and take over as CEO. I hadn't ever envisioned myself as a CEO but I said yes. It turned out to be the most challenging role I'd ever had. Fortunately, I could draw on my operating skills and people skills gained from my GM jobs.

It was late 2008, the organization was in crisis. To survive, it had to reduce expenses. Which meant I had to reduce staff by 40 percent. Painful. But once we survived the recession, my mandate switched to rebuilding the enterprise so we could serve more kids. That meant several things. One, reestablish best practice—what does good look like? Two, get the service delivery model really humming and find efficiencies to reduce expenses. Three, raise vastly more revenue. BBBS had raised money by staging events, fundraising benefits, but we hadn't approached prospective donors individually. That kind of top-to-top fundraising now fell to me.

The CEO role had stretched me in many ways but this was different. It was very personal.

First, I realized that I wasn't in the right relationship with the board. Coming in, I thought that the board was the boss—or at least a peer—and I was the facilitator to help the board arrive at decisions. I was operating naively from the viewpoint that the board hired me to help them, as opposed to realizing that I'd been appointed as CEO to drive the organization. Before Big Brothers Big Sisters, I had always worked in structures with people above me.

The same dynamic played out with donors, especially big donors, billionaires. I'm not a billionaire: who am I to be approaching these people? Both with the board and with big donors I had, without quite realizing it, put myself in a one-down position. They hadn't done that to me, I had done that to myself. Even to role-play being on a par with board members or billionaire donors was a stretch for me.

That brings me to a related speed bump, which came to light very subtly. I'd engaged a leadership consultant, actually two—they worked in pairs—who did a 360-degree study on me. When we met to go over the findings, they noticed I focused on the negative feedback and underreacted to the positive. Why was that, they asked. Simple: my mind was closed to it. Not just closed: it was as if I had my shoulder pressed against the door. And why was that, they asked. Because I'm fixated on not being good enough, I told them; I'm a pretender to this throne and any day now I'm going to be found out.

From my earliest days, I had worried that I wasn't smart, that my good grades in school were only because I worked hard, that, horror of horrors, I was just another overachiever. In middle school I dreaded the start of a new school year: what if I couldn't pull it off again, what if I my work ethic wasn't strong enough.

The consultants gave me some time to reflect. Sitting quietly with my eyes closed, it hit me out of the blue: you're plenty good enough! It was like snapping out of a bad dream. Ironically, I didn't want to do the 360 work. I was too busy; I didn't see the need. But a board member I respected and who cared about me strongly recommended it.

The realizations I came to allowed me to operate from a place of confidence and "fill my suit" as CEO.  I took the reins and began to lead the Board. I imagined myself as a tyrannosaurus rex and all my experience, knowledge and skills were lodged in my giant tail. Walking into a Board meeting or a meeting with a billionaire donor, I swished my imaginary tail and thumped it—a reminder I've got what it takes.

The Board applauded the shift, my hit rate with donors increased, and the resulting jump in funding fueled the jump in scale we aspired to.

But after ten years in the role and fourteen years in the organization I felt it was time to step down. I'd had my chance to raise up BBBS and I felt it was time to step down and let someone else take the operation to even greater heights. The board would have been happy if I had continued. But the time had come; I had made up my mind.

The only remaining challenge was to effect a CEO succession, a natural transition that would engender stability in an inherently fragile organization. Ultimately it took a year and my successor was chosen from within. I am confident the best days of the organization lie ahead. 

I feel proud of myself for making the several turns in my career. I could never, for example, have contemplated running a nonprofit. I have only one regret, that I didn't recognize earlier in my career those deeply personal changes that needed to be made.

As I contemplate the next step in my career, I'm excited about the possibilities—there are so many things happening in the world, so many problems to solve, and places where my expertise would fit.

But there's also absolute terror. Will I ever find something as challenging and exciting as my last job? Will I, a 58-year-old white woman, ever get hired again? And there's a deeper fear born of a new awareness: I want to change my life, I need to change my life, but I'm afraid I can't. My work ethic and drive to achieve have made my life at work and outside of work a living to-do list, and I don't want that to continue. I don't want work, unending tasks, to crowd out everything else. Another speed bump, the biggest yet.

I could be absolutely gunning for the biggest job I could bite off. That's very compelling, very exciting. But there's no way I can justify taking a big job unless I can set limits—draw the boundaries.

Here I am between jobs, presented with a lovely opportunity to enjoy the rest of what life has to offer. All the things I love to do I'm finally free to do: read for pleasure, learn for learning's sake, play music, take photographs, cook, get exercise, walk outdoors, meditate, plan unique experiences, heck just sit and relax. Not to mention lavish time on my wife, Claudia, and friends. And yet, even with the freedom and the desire to do anything I want, I still put getting things done first.

This goes all the way back to my childhood, to how I was shaped and formed. I had a wonderful childhood in many ways. I grew up in a close and loving family. And yet how did I get love from Mom and Dad? By achieving. I was fortunate that my parents had an unwavering belief in my ability, but there was no tolerance for less than perfect. If my father felt I had underachieved, his disappointment was crushing.

So what did I turn into? An achievement junkie. To this day I find it almost not okay to relax. Because it's not productive. Because it's frivolous. Because it's selfish. I know better but a loud voice in my head says, get back to work. I have availed myself of coaching and have started to make the turn. It isn't easy, but I believe that "fully Wendy" as opposed to "work Wendy" will be a more whole, more creative, and ultimately more capable person.  I'm determined to figure this one out and I have faith that I will.

I don't want to die without living fully.