REGINALD K. BRACK JR. graduated from Washington and Lee University in 1959 and headed west to St. Louis to take a job selling advertising for The Saturday Evening Post. Three years later, he was sitting on an airplane and struck up a conversation with a man who turned out to be the publisher of Time Magazine.

“A lot of life is serendipity,” Mr. Brack said of that seat assignment.

But then came the hard work. Mr. Brack was recruited to join Time a few months after that flight, and he stayed there for the next 37 years. In 1986, he was named chief executive of Time’s magazine division and chief executive of Time Inc. in 1990. He retired as chairman in 1997 and stayed on for two more years as nonexecutive chairman.

Mr. Brack’s rise through the corporate ranks was a classic self-made-man story — his father worked in the airline industry in Dallas — and it was also accompanied by great wealth, in salary and stock. Yet even though his earnings increased over the years, he said he paid little attention to it. Now in retirement, he is faced with some choices.

As a member of Tiger 21, an elite investment club, he has at least its minimum of $10 million — the net worth that currently makes a married couple subject to the federal estate tax — but he does not want to say how much he has beyond that amount.

“I don’t have near the wealth people think I do,” he said. “I’m certainly not poor, but I don’t count myself as a great, wealthy American.”

Mr. Brack would rather talk about his working years than money any day. He was the first person to run the company who had not gone to an Ivy League college and also the first chief executive who started his career in sales, not journalism or finance. He also appointed the first female publisher at any Time magazine.

But now that Mr. Brack, 73, is working less, he has time to think about his wealth. He sits on several boards, including that of Fieldpoint Private Bank and Trust, which he helped found, in Greenwich, Conn., where he lives. But he is less busy than he was in his days at Time. Financially, he thinks about his cash-flow needs, his charity and his family; he is married with three grown children.

Self-made executives often delay wealth planning, said Sharon H. Jacquet, managing director in J. P. Morgan Private Bank, who runs a team that works with senior executives of public and private companies.

“Not thinking about finances until retirement is not uncommon,” she said. “Really successful C.E.O.’s put the priority on doing their job as a C.E.O. They have a comfortable lifestyle and adequate financial resources, and they don’t focus on it.”

In his professional life, Mr. Brack said he concentrated on work during the week and his family the rest of the time. This helped him be successful, but it also left him in his 70s with a seemingly diffuse financial plan.

Early on, he started with an adviser in Allentown, Pa., who persuaded him to sell some of his high concentration of Time Warner stock ahead of his retirement. This diversification helped Mr. Brack, and he remains loyal to his adviser.

Mr. Brack chose the Royal Bank of Canada to create his municipal bond portfolio after a search many years ago to determine which firm had the top muni management team. He credits that part of his portfolio with helping him sleep during the financial crisis. “I was frightened, but I was comforted by that muni bond portfolio,” he said.

His third adviser, after the team at the Royal Bank, works for Fieldpoint Private Bank and Trust and counsels him on estate issues, equities and new managers.

While three advisers may seem like too many cooks in the kitchen, Ms. Jacquet said it could work if one of them had the entire financial and legal picture, even if someone else was managing the assets. Mr. Brack said Fieldpoint has the full picture of his finances.

Estate planning is crucial for Mr. Brack and his wife. When they die, there will almost certainly be money left over. But they do not have so much that he feels comfortable taking advantage of the generous gift tax exemption of $5 million per person that is in effect for the next two years. (This is separate from the annual gift exclusion of $13,000.) “That would be a serious diminution to our lifestyle,” he said.

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