Before reporting to prison, every smart white-collar criminal knows what to do: hire a consultant.
There are so many details to work out -- being sent to the cushiest possible jail, handing over control of personal finances, coping with the psychic shock sure to set in when the cell door bangs shut and freedom, even if for just a few months, is snatched away.
Martha Stewart, sentenced on Friday to five months in prison for lying to federal agents about a stock sale, has one of the best-known consultants in the business in Herbert J. Hoelter.
Hoelter, who has helped such people as financier Michael Milken and Sotheby's chairman A. Alfred Taubman adjust to prison life, said in an interview that the biggest challenge often is making formerly powerful clients understand that Bureau of Prisons rules do not allow them to conduct business from prison and that their contact with the outside world will be severely restricted.
The message doesn't always get through.
Hoelter said a client in California recently got tossed into solitary confinement after guards caught him trying to sign some closing papers he'd been sent for a real estate sale. Another lawyer said one of his Wall Street clients demanded to know what his e-mail address would be in jail. Inmates cannot use e-mail.
"The transition from being outside to being an inmate is a dramatic one," said Hoelter, who runs the National Center on Institutions and Alternatives in Baltimore.
Stewart, has already taken care of a major real estate deal, selling a luxury apartment in Manhattan. Over the past few weeks, she has also sold several million dollars worth of stock in the company she founded, Martha Stewart Living Omnimedia Inc. But, as other white-collar criminals have found, there are other matters to consider.
In 2002, weeks before he was set to report to a federal prison camp in Florida to serve a 41-month sentence for fraud, shoe designer Steve Madden decided to take care of a few painful loose ends: his teeth.
Madden's lawyer petitioned a judge for a short delay in the start of his sentence so he could get a root canal, fill some cavities and have surgery to fix a deviated septum.
"Every lawyer who has a client on his way to a federal institution should advise his client to take care of all his dental and medical needs before they get there so they won't have to resort to care from people they don't know, and it's probably substandard care," said Joel Winograd, a New York-based lawyer for Madden.
Winograd said Madden's business has continued to do well because Madden arranged for a good team to run things in his absence. "The company is bigger than any one person -- same with Martha Stewart," Winograd said.
Beyond personal and financial matters, consultants and lawyers strongly recommend that prison-bound former executives prepare themselves psychologically.
Sentencing consultant David Novak, who served a year in prison on a mail-fraud charge, said that applies to Stewart despite her tough talk outside the courthouse on Friday about not being afraid.
"Of course she's afraid," Novak said. "Any human being would be."
Novak added that Stewart "needs to get to the point where she can look in the mirror and say what she did was in fact a violation of the U.S. code. She wasn't coerced. These were simply poor choices she made. . . . Immediately after incarceration she needs to recognize that she is no better or worse than any other inmate."
Veteran Washington defense lawyer Henry W. Asbill said the attitude adjustment can be very difficult for those accustomed to giving orders, not taking them.
"You want to be showing up there primed to not be a problem, to not be unusual, to not think you are still in control," Asbill said.
Stewart will have plenty of time to prepare.
U.S. District Judge Miriam Goldman Cedarbaum granted a stay of Stewart's sentence while an appeal proceeds, which could take more than a year. If and when Stewart does go to prison, Cedarbaum recommended that she be sent to Danbury Federal Correction Institute in Connecticut, a women's prison that has a minimum-security camp.
Inmates at such facilities do not have access to e-mail or computer modems, their regular mail is closely monitored and they get only 300 minutes a month in phone calls, according to Dan Dunne, a spokesman for the Bureau of Prisons, the federal agency that determines where convicts serve their time. Visits are allowed as long as the guest is on an approved list.
Prisoners in the federal system must work 71/2 hours a day unless they have medical excuses, and they are paid less than $1 an hour. The jobs are typically in the food service, grounds crew or sanitation areas. Inmates wear khaki outfits with steel-toed black shoes during work hours. Sweat suits are allowed during non-working hours.
It is not certain that Stewart will wind up at Danbury. Novak said the Connecticut facility does not usually take inmates with such short sentences. He said Stewart instead could be sent to a temporary facility in lower Manhattan known for its decrepit condition.
Hoelter said that was unlikely and that he was confident Stewart would serve her sentence in Danbury.
Wherever she goes, Jeremiah Donovan, an Old Saybrook, Conn., lawyer who represents several convicted business executives, said Stewart will have to go through a lengthy checklist of pre-prison activities.
"In the time just before you go to prison, there's a bunch of little things you need to do, practical things," he said.
For example, he said, you can't even bring your address book with you. "Whatever you go in with, they're going to take away from you," Donovan said. "I have clients write themselves a letter that will arrive that day or the day after, to write down all the names and addresses of their friends."
Donovan said he also tries to make introductions if one of his clients is going where another one is already serving time. "I'll look to see if I know anybody from the prison and write them to say, 'Hey, this is a good guy, look after them,' " he said.