When Thomas Gallagher was 17, he worked as a clerk on the floor of the New York Stock Exchange and put $10 a week into an account at Irving Bank. “That was my discipline, my savings,” Mr. Gallagher said. “Back then, the goal was to have enough money to buy Christmas presents.”

Mr. Gallagher, who is retired from his position as vice chairman of Canadian Imperial Bank of Commerce World Markets, is a member of Tiger 21, a network of over 570 members who collectively manage more than $50 billion worth of personal investable assets.

At age 72, he is a multimillionaire. Even so, “I still feel, to some extent, that I don’t have enough money,” he said. “Emotionally, I don’t come from money; I got very lucky on Wall Street. I’ve been dealing with a myriad of psychological issues since I retired. I have more money than I had ever imagined, but I still worry — do I have enough, if I live longer than I thought?”

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The psychology of wealth is knotty. On the surface, being wealthy can make people believe they have more control over their lives, but it can also control them emotionally, said Olivia Mellan, a psychotherapist in Washington who specializes in money issues and is the author of “Money Harmony: A Road Map for Individuals and Couples.”

“If someone doesn’t have that money growing up, it’s like being shot through with too much energy,” she said. “There’s this undercurrent that money equals love, power, security, control, self-worth, self-love, freedom, self-esteem — all those loaded things that money supposedly can do, but doesn’t.”

Wealth frequently comes with a bundle of expectations — anxiety and pressure to make smart money decisions, for example, about how it is managed, spent, passed on to future generations, or used to create a legacy.

There is a degree of fear. “People are afraid of the money, how it might corrupt them, or make them insensitive to other people’s plights,” Ms. Mellan said. “They worry about their kids having so much money thrown at them that they will not be motivated to work for money and have a meaningful life.”

Eric D. Bailey, founder and chief executive of Bailey Wealth Advisors in Silver Spring, Md., said possessing wealth was an uneasy feeling for many of his clients, a combination of business owners and mid- and upper-level executives whose average net worth is $3 million to $15 million. “They don’t take it for granted,” he said. “They never do feel they have enough. It takes some coaxing to get them to spend money.”

He said he helped them understand that under any combination of scenarios, the odds were very low that they would outlive their money.

What many people who become wealthy are not prepared for is the emotional difficulty of dealing with money, said James Grubman, a psychologist and founder of FamilyWealth Consulting. “For more people than you would think, the adjustment to having money is quite stressful,” Mr. Grubman said. “No one gets a lot of empathy talking about these things.”

This is easy to understand if you think about the stereotypes that society generally has about the rich, he added. “If you grow up hearing money messages like rich people only care about themselves or other negative beliefs about the wealthy and then you become wealthy yourself, how are you going to reconcile what you believed about those people with the fact that now you are one of them?”

Another worry is that if you are rich, you have a target on your back, and people are always going to hit you up for loans and gifts. There is the security and the stability and the success that wealth represents, but people just do not want the identity and the downside of what they associate with being rich, he said.

One way to combat the apprehension about wealth is financial education. “The anxiety that comes with having acquired wealth is alleviated by having the confidence you can learn what you need to learn,” said Charlotte Beyer, author of “Wealth Management Unwrapped Revised and Expanded: Unwrap What You Need to Know and Enjoy the Present” and founder of the Institute for Private Investors, a provider of educational and networking resources for ultrahigh net worth investors and the nonprofit Principle Quest Foundation, which supports education and mentoring for girls and women.

“You need to decide what do I want this money to do?” Ms. Beyer said. “How you spend your money is the ultimate representation of your values, and you should do it with joy and fun and love.”

Inherited wealth comes with some different worries.

Susan Remmer Ryzewic, 66, came into a fortune after her father died and his engineering business was sold for $100 million. “The biggest anxieties were working out the differences with my siblings on how the family wanted the money invested and what they felt the money should represent,” she said. “If you don’t manage the emotional and family aspects, the money doesn’t matter.”

When the family’s fortune landed, it was overwhelming. “We found we couldn’t move forward initially because we were all so concerned about our own agenda that we were not really listening to each other,” Ms. Remmer Ryzewic said. “It took awhile for us to be speaking the same language.”

Ms. Remmer Ryzewic, her brother and two sisters spent a lot of time in the first few years getting educated. She took a number of courses on fixed income investments and aspects of portfolio management so she could be a reasonably informed consumer.

And there is that nagging feeling of being taken advantage of. “In the beginning you are thinking all these people are so wonderful and nice and then you realize everybody wants a piece of something,” Ms. Remmer Ryzewic said. “You get sort of cynical. And I started feeling I was being defined by it. Now I just feel so fortunate that it provides me with choices. Initially, it was way more responsibility; now I am comfortable with the responsibility.”

One highlight of their good fortune: Ms. Remmer Ryzewic, her sisters and mother, who is now deceased, set up The Remmer Family Foundation, a private charitable foundation, with some of the proceeds. One of the foundation’s goals is to reduce poverty for women and youth by helping disadvantaged adolescent and preadolescent girls take ownership of their lives. The foundation also encourages environmental stewardship by improving the sustainability of the world’s fisheries.

Acquiring wealth from the sale of an entrepreneurial venture has its own set of mental gymnastics.

“First generation wealth creators who sell their business and now are investing their wealth and dealing with their wealth are different than second generation, or someone who got it by the lottery,” said Michael Sonnenfeldt, founder and chairman of Tiger 21, and author of “Think Bigger: And 39 Other Winning Strategies From Successful Entrepreneurs.” They have finally made it from modest beginnings and are now in a brave new world, he added.

“They’re in their sweet spot, and then they sell their business and they’re adrift,” Mr. Sonnenfeldt said. It is like jumping through the looking glass, he said. You are going back to square one.”

Then too, for many entrepreneurs, they spent a lifetime reaching just beyond their grasp, always reaching for the next goal, he said. “It’s a really lucky person who can say I have enough. I am comfortable with what I have.”

By KERRY HANNON