Breaking In
When I left the University of Chicago in 1958, I was only eighteen and not entirely sure where I belonged—two years of college had given me confidence but no clear direction. So I packed my bags and moved to New York City, where I found my first real job as a clerk in the actuarial department at New York Life Insurance Company.
That is how my career began, not with a grand plan, but with a desk, a stack of ledgers, and a curiosity about numbers.
At the same time, I started studying for the actuarial exams. I attended evening classes sponsored by the New York Actuaries Club, held in the insurance offices along Madison Avenue. The first exams were pure math, plus one on English proficiency, which still makes me smile. I passed the first three exams in May 1959 and then the next two the following year.
By 1960, just before my twentieth birthday, I became an Associate of the Society of Actuaries, one of the youngest ever at the time.
It was heady stuff for a teenager pretending to be a grown-up in the heart of Manhattan. I had been promoted into the actuarial student program at New York Life, which meant a raise, rotations through different assignments, and camaraderie with the other students. They played bridge at lunch, and I joined in. It helped me fit in, and passing exams helped even more. I was doing better than some who had been formally hired into the program, and that gave me confidence.
Exams were very different then. Everything was written by hand: long, detailed math problems with essay-style answers—no multiple-choice. No computers. You could only take them once a year in the spring. I did not pass any in 1961, but I passed the rest in 1962 and 1963. That year, at age twenty-three, I became a Fellow of the Society of Actuaries.
That was also the year I appeared in The New York Times. Mademoiselle magazine listed me among ten promising young women. I remember feeling surprised. I did not quite understand what I had done to deserve the attention, but I appreciated it all the same.
A Career and a Baby
Those early years were full. My daughter, Jennifer, was born in 1960, right after I became an associate. My husband was in law school, and we were juggling rent, tuition, diapers, and actuarial tables all at once. I worked full-time and helped put him through school.
Then came one of those moments that defined an era. When I became pregnant, New York Life terminated my employment. Pregnant women were not considered suitable for office work. The company did not like their appearance. So I left, not by choice.
I soon found a temporary job at George B. Buck Consulting, but I did not enjoy the consulting aspect of the work. After Jennifer was born, I agreed to return to New York Life on the condition that they change the rule that barred pregnant women from working. To their credit, they did, though not without resistance.
I will never forget what the company’s medical director told me when I came back:
“Young woman, you belong at home with that child.”
That was the world we lived in. Patronizing. Rigid. Blind to potential. Still, I stayed two more years because I loved the work and I needed the paycheck.
Standard Security: Learning Everything
In 1962, I moved to a much smaller company, Standard Security Life of New York, and stayed there for eleven years. Looking back, that move changed everything for me.
At Standard Security, I was part of a small team of four in the actuarial department, which meant I handled a wide range of work. Pricing. Product design. Financial reporting. Talking to brokers and agents. Helping shape marketing materials. It was like earning a second degree, but this time in how a business actually works.
The company was innovative, selling term insurance through independent brokers instead of a traditional sales force. It was lean, fast-moving, and full of ideas. For someone who liked thinking across boundaries, it was an excellent fit.
Small insurance companies in those days rarely survived in the long term. Many were undercapitalized, and eventually Standard Security was absorbed by a larger company. But by then, I had already learned more than I ever could have at a big firm.
The Shift to Equitable
By 1973, I moved on to The Equitable Life Assurance Society, now known as AXA. My role there felt like a dream. I was part of the actuarial department, but my focus was on the future. I studied markets, demographic trends, and long-term business issues. I was encouraged to imagine what financial services might look like in 10 or 20 years.
It was the beginning of a pattern that would define much of my career: connecting technical expertise with social and economic context. Not just the math, but the people behind the math.
My next steps after Equitable led me to Mercer and eventually deeper involvement with the Society of Actuaries.
Seeing the Future
Working at Equitable felt like stepping into a laboratory for ideas. The company had hired a small group to focus on long-range planning. For me, that was extraordinary. I was naturally curious about what was coming next, and there I was, being paid to study it.
My work revolved around futurism, though I did not use that word at the time. I immersed myself in demographics. I studied how the population was aging, how more women were entering the workforce, and how household structures were shifting. These were not abstract statistics. They were early signals of what would shape insurance, retirement systems, and financial security.
Equitable did not immediately act on my findings, but the habit of watching trends before they became headlines stayed with me. It shaped my thinking for the rest of my career.
Shifting Focus
One of the studies I worked on analyzed how the life insurance industry served different income groups. Some companies focused on the upper-income market. Others in the middle market. A few still sold small industrial policies to working-class families, collecting premiums door-to-door. Even then, I could see the tension between access and profit. How to serve lower-income households remains a challenge today.
After three years at Equitable, I knew it was time to move on. I wanted more direct work with organizations that design retirement and benefits plans. In 1976, I left New York and joined Mercer, relocating to Chicago.
The Mercer Years
Mercer, then part of Marsh and McLennan, gave me a global platform. Some actuaries preferred smaller partnerships, but I immediately saw the benefits of a large publicly traded company with access to capital. Mercer could acquire firms, expand internationally, and build a consulting network unlike any other.
When I arrived, Mercer focused on employee benefits and retirement plans. I started as a traditional consultant serving corporate clients, but soon gravitated toward broader questions. Policy. Demographics. Economics. How all these forces combined to shape financial security.
At the same time, I stayed actively involved with the Society of Actuaries. I had served on the Board and was Treasurer when I joined Mercer. Those ties kept me embedded in professional conversations and helped bring new ideas into the firm.
Over the years, my role at Mercer changed. I moved from client work into shaping intellectual capital. Writing. Teaching. Training. Helping people see around corners. I found that I loved being a mentor as much as being an analyst.
A Period of Growth
The late 1970s and early 1980s were a transformative time. Congress passed primary pension legislation that reshaped retirement plans. Mercer organized a series of nationwide seminars to help employers understand the new rules, and I helped develop and present them. Eventually, we expanded the program internationally.
Those years taught me an important lesson. Influence is not always about title. It is often about ideas and the ability to help others see the bigger picture.
Turning Foresight into Practice
By 1976, I already had a reputation for looking beyond formulas and funding ratios. I had co-authored two papers with Peter Plumley, including one on social and demographic change in financial services. Mercer hired me partly for that broader perspective.
In 1978, three significant regulatory changes created the perfect moment to apply it. These included the Pregnancy Disability Act, changes to the Age Discrimination in Employment Act, and another nondiscrimination rule affecting benefit plans. Employers needed guidance. A regional manager suggested seminars. The idea grew quickly.
We eventually held thirteen seminars across the country. They were holistic and unlike anything most clients had seen. We opened with an overview of social and demographic change. Then came sections on compensation, Social Security, pensions, and health benefits.
I remember sharing the platform with Hayworth Robertson, the Chief Actuary of Social Security, who explained demographic pressures on the system. Clients were not used to this kind of framing. Some were intrigued. Others resisted. One executive from Ohio disliked our message so intensely that he told me so at the time. Twenty-five or thirty years later, he approached me at a conference and said, “I really hated what you said back then, but you were right.”
That comment stayed with me for years.
Broadening the Work
Those seminars reinforced something I had long sensed. People often make decisions without understanding the larger social forces that shape them. Once they saw how demographics, aging, and societal change fit together, the work took on new meaning.
At Mercer, I worked with a wide range of clients, large and small, domestic and international. I led some projects and supported others in different offices. I spent much of my time writing, teaching, and helping articulate the firm’s intellectual direction.
It was not a traditional consulting path, but it was deeply fulfilling. There were frustrations, naturally, but in retrospect, I am glad I stayed twenty-eight years. The work gave me variety, purpose, and a professional home that valued ideas.
By the time I retired from Mercer in late 2004 at age sixty-four, I felt grateful and also ready for a new chapter.
Reinventing Purpose
In 2005, after reflecting on what I wanted next, I founded Anna Rappaport Consulting. My work focused on research, writing, and presentations, with occasional consulting projects that matched my interests.
In the mid-1990s, during my term as President of the Society of Actuaries, we had begun rethinking retirement planning. Most conversations focused on saving enough to retire, not on managing life and money afterward. I believed that gap mattered. That belief eventually grew into a decades-long research effort on post-retirement risks, one that continues to evolve.
I often smile when I think about it. I started my career studying life expectancy tables and eventually found myself exploring what it truly means to live those extra years, both financially and emotionally.
A Life in Phases
By the 2000s, I began to think of my life in phases. Not chapters that ended, but shifts in emphasis. I sometimes call myself a phased retiree because that is how it feels. My time is divided among family, professional work, and art, and the rhythm changes from year to year.
Peter and I had a blended family with five children and seven grandchildren spread across the country. Travel became part of life. So did intentional moments. I set a quiet goal for myself: quality time with each grandchild every year. One of the most memorable trips was to Norway in 2010 with my daughter and her children to celebrate my seventieth birthday and her fiftieth.
Creativity expanded during this phase. I leaned into painting, collage, and photography. I experimented with color, movement, and unexpected textures. Some of my work became part of the Artuaries charitable project that supports the Actuarial Foundation. It still delights me that my two worlds found a way to meet.
Even in this phase, I remained professionally active. I chaired the Society of Actuaries Committee on Post-Retirement Needs and Risks and continued supporting research that would help older Americans navigate a longer life. Women’s issues became even more central to my advocacy. Women live longer, earn less, take more career breaks, and carry more caregiving responsibilities. These realities shape economic vulnerability, and I wanted to help address them. Serving with WISER, the Pension Research Council, the ERISA Advisory Council, and the GAO Retirement Security Advisory Panel gave me meaningful avenues to contribute.
Community mattered too. The Chicago Network became a grounding space where accomplished women shared ideas and encouraged one another.
And of course, I continued writing. Pension Section News became a place to reflect on lessons learned and insights gained. In 2013, I wrote about phased retirement from the perspective of someone living it. That piece felt like a marker of where I stood at the time and what I hoped to share.
If there is a thread that ties these years together, it is the belief that retirement should not mean retreat. I wanted my work to continue mattering. I wanted to keep contributing.
Today, I remain curious, creative, and engaged. If you would like to learn more about my current work and reflections, I spoke about many of these themes in the Women Over 70 podcast, Episode 345.
I also did a conversation on the future of phased retirement with Casey Weade. That conversation is available at: https://howardbailey.com/podcast/anna-rappaport
These interviews capture the questions I continue to explore, the issues that still compel me, and the ongoing evolution of my life in this phase.