Midlife Career Change Advice From Baby Boomers to Millennials

Millennials are "lazy, entitled narcissists," according to Baby Boomers. Hold on Millennials, before you make this about yourselves you should know that Baby Boomers contemplated and made midlife career changes long before you felt the need to take a semester off to find yourselves in Europe. When workers make the critical decision to leave one career for another, where do they end up?

We spend our entire life planning for our careers. From kindergarten on, we never stop contemplating what we’re going to be when we grow up. Professions are a part of our identities as individuals, beginning at a very young age. Additionally, the number of years spent in training and education for any profession makes it increasingly difficult to change fields once we’ve started on a career path.

With the growing student loan debt and high level of specialization needed in many professions, the opportunities to switch career paths are becoming narrower. While the goal varies by individual – several fields routinely see a substantial influx. Some of the most common and popular industries for career changers to leap into today are information technology, nursing, real estate, and teaching. The ability to earn a decent entry-level income is also important. Professionals don’t want to have to start over at the bottom or move too far away from their financial comfort zone. This means that many career hoppers are looking for professions with a decent entry-level salary and limited educational requirements.

Some of the best jobs for midlife career changes include interior design, small business owners, financial services, artistic endeavors, and business consulting. But before you decide to jump the gun, Baby Boomers who made the changes offer points for Millennials to consider when contemplating midlife career changes.

Real Life Experience

The corporate world of New York television seemed light years away to Nancy Royce. She was tired of the hectic and stressful pace of her job as director of the division that ran ABC's group of owned and operated stations, her dream began when she was 43 – as she sat in a friend's apartment and heard her complain that she couldn't afford tiling. "I told her jokingly, 'I've been looking for something creative to do, so I'll make some for you,'" she recalled. After leaving her position in 1987, Royce packed her belongings and headed off in search of new surroundings. Eventually, she settled in Atlanta and got a job three days a week as a communications consultant, leaving her time for her newly discovered love: painting and designing china and porcelain tile. "All of a sudden, out of nowhere, it dawned on me," said Royce. "I remembered that incident back in the city and realized that doing this kind of work would combine my longstanding desire to be creative with my proven abilities in the business world." Under the guidance of a teacher, Royce mastered the craft, started her own manufacturing business, and co-authored a book on the subject with her instructor.

The same opportunity to fulfill a career fantasy came to Alfred Romagnolo many years ago, when the Dallas-based computer executive left his position to sail off into uncertain waters with his wife on their yacht, The Gracious Lady. They started their own charter business on St. Thomas in the Virgin Islands. The (then) 47-year-old boating enthusiast, a native Philadelphian, decided it was time to make that drastic and ambitious move when the company he was a part of decided to sell out. "We had been talking about trying that kind of venture when we got older, but my decision to leave the company only made us look at it sooner," explains Romagnolo. "It seemed an excellent time to try it out. After all, running this kind of business demands that you be vigorous and in good shape. And I didn't want to reach 65 and look back and say, 'Why didn't I do this 20 years ago?'" After a year in business, the company became increasingly successful, as Romagnolo and his wife (who acted as a chef) ferried small groups of tourists around the islands while offering them snorkeling, water-skiing, and diving. However, Romagnolo eventually sold the operation and returned to the United States to start a third career.

Midlife Career Crisis

Such dramatic midlife vocational shifts no longer seem so unique in today's business world. Bill Morin, a former chairman and CEO of Drake Beam Morin Inc., which was a leading career management firm, reports that of those executives who came to his firm for new job counseling, a solid 40 percent opted for a major shift in their occupational direction. And, according to Morin, such changes are not all that unusual in today’s job market. His company saw the average college graduate make three such major career switches in his or her lifetime. Aside from the external pressures of a compressed middle-level job market, the movement for change seemed to also be precipitated in large measure by the maturing of the baby­boom generation whose members looked to work not as an end in itself, but as a means to a satisfying lifestyle. Halik Walfesh, former president of Retirement Advisors – what used to be a New York-based counseling firm with clients that ranged in age from their 40's to the later years, explained: "People who were traditionally in the midlife career crisis were those who were affected by the Peggy Lee syndrome that asks, 'Hey, is that all there is?' Many of them woke up one day and realized that they were tired of the daily work grind and of the three-hour commute from Connecticut. They said to themselves, 'I don't feel fulfilled. That's not what I wanted to do when I grew up.' And more and more people focused on that aspect."

To Each His (or Her) Own

Still, many experts warn that such dramatic career shifts may not be right for everyone. They advise the individual to determine if he or she is truly a risk-taker or someone who prefers the structure and security of their present position. They also suggest taking a self-inventory that assesses skills, aptitudes, and interests, and encourage an honest look at financial resources, which will be needed to successfully cushion the hard times that may occur when the transition is made. One such authority on job-changing is Richard Bolles, whose often-used What Color Is Your Parachute? presents a concrete road map for identifying one's mission in life and then reaching that goal. Said Bolles: "The major fallacy today is that people always want to know the answer to the question, 'What's hot and what's not?' Instead, people need to search their heart to see what they most love to do. If one is religious, one assumes that God not only gave us a particular talent, but that he gave us a love for using that talent, too."

Many specialized counseling firms help mature executives unlock that new career door, offering batteries of tests to determine one's vocational direction along with in-depth sessions to help the individual market themselves in their newly chosen field. And former organizational-psychologist-turned­ author Marsha Sinetar offers an intriguing developmental approach to help the individual find his or her true life's calling in her career guide Do What You Love, The Money Will Follow. Her advice includes this method to help focus on the areas that might lead to a personally rewarding vocation: "I suggest that you run a mental scan of your entire personal history. Find the times when you engaged in tasks that were so totally absorbing that you’d start working on them in the morning and didn't realize what time it was till you looked at your watch and found it was 4:30 in the afternoon. You said to yourself, 'Where did the time go?' – you've lost that time and space factor. Then start to play detective to see what it was about those activities that made them so special for you."

Explore Your Options

For some, this preference has been known but has been suppressed by the realities of their particular life situations. As a young woman, Carol Isackson's desire to become a lawyer was thwarted when officials at the law school she was to attend dissuaded her from entering, arguing that women would find limited opportunities in that profession. Instead, Isackson opted for a master's degree in social work, which led her to her last job as a psychiatric social worker, a job she held until her old desires could no longer be repressed. Following a divorce, Isackson quit her job and began attending law school full-time, graduating at the age of 36. She now practices in San Diego, specializing in hospital and doctor defense litigation. Despite her success at starting over, she offers words of caution for others whose newly discovered career preferences may also involve considerable retraining. "I think you have to be really very motivated and clear this is something you want to do and is something you're going to completely love," says Isackson. "If you're not, there's a lot of stress associated with going back to school prior to making your change. It's an enormous adjustment and very demanding." To learn whether or not one can succeed in a totally different field; experts suggest that it's best to start training for the desired job area while still employed, if possible. That enables the individual to not only learn what the career area actually involves, but to also receive valuable preparation. This total commitment to learn needed new skills and investigations of the day-to-day challenges of the targeted career was successfully undertaken by Scott Lakis, who left his job as a bank's personnel officer to open a wine and food shop, along with a more recent gourmet specialties store.

Suggests a retired San Franciscan: "Don't leave any stone unturned in terms of talking with people. Most people in any business are more than happy to talk about what they do because 99% of them are at it because they like it. I spent a lot of time talking to people in the bar/restaurant/food area and just listening. People say a lot of things they don't really mean to say, and the important thing is to listen to that and glean from it the things that are important to your goals." Yet even in the best of efforts, many career switchers can face a long and difficult start-up period, and one where their old, comfortable lifestyle is a thing of the past – at least for a while. That's why some counselors, such as Jerry Johnson, former vice president of a major human-resources firm and host of the Bay Area talk-radio show Man to Man, says it is vital to include one's family members in any job­ change decision. "If someone is married to an executive officer of a big bank and the breadwinner doesn't want to do that anymore, obviously the family is going to be affected after being in that same lifestyle," says Johnson. "It's very unusual that the individual is going to be successful in making that change if he or she doesn't have the support at home. That can be the beginning of the end for many marriages if not handled properly."

Have Desire – Talent and Luck Don't Hurt Either

However, if the desire is truly there – along with the talent and some luck – many experts like Sinetar feel that midlife career changers have an excellent chance of succeeding in their new personal vision quests. "Remember as a kid, spinning around and spinning around and rolling on the grass and the whole world seemed to move, or running on the street and it almost seemed you could fly? That's the kind of experience you can get through truly rewarding work," says Sinetar. "If you put 100 percent of yourself into it, you really do, fly beyond yourself. It's very important that people capture that joy and happiness and liberation they felt as a child. I've had people tell me 'You can't be that happy,' and it's just not true."

Certainly agreeing with that upbeat assessment was 53-year-old government-administrator-turned-lawyer Morris H. Ordover. Like Isackson, he wanted a legal career in his earlier years, but had to suppress the desire for economic reasons. At the age of 40, that all changed; Ordover began night law school and graduated four years later. After taking early retirement, he practiced condominium and co-op law in New York full-time. Ordover recalled, however, that making the change wasn't easy: "I remember visiting my law professor one night to talk about some academic and personal problems I was having at the time. He looked at me and asked if I knew how far I could reach out my hand. I told him I didn't. 'That's right,' he answered, 'you don't know how far you can reach till you try.' And that's been the story of my life ever since. I still don't know how far I can reach, but I'm still reaching."