"I hit 30 and said, practicality be damned," Cobb says.
Despite the seemingly quixotic venture, Cobb did have some grounding. His father, Steven Cobb, a Scottsdale, Ariz., ophthalmologist and now-retired financial planner, advised his son on every aspect of living with a precarious income - from shedding credit card debt to saving on reeds for his instrument. Together, they plotted a budget based around a month-to-month apartment lease, so Cobb knew he would have a few months to start earning before he was forced to live in his parents' basement.
Four years after moving to New York, Cobb is now a part-time graduate student of music at New York University and lives in a group house with other artists. He supports himself as a program officer at the New York Foundation for the Arts, where he helps set up financial boot camp for artists - including an upcoming seminar run by his father on planning for artists.
"And I'm putting away for retirement," the younger Cobb says. "It's not an approach every artist wants to take, but I appreciate that he's given that [guidance] to me. I'm probably better set up, with a better structure in place, than a lot of my contemporaries."
Retirement planning is challenging enough when clients have steady paychecks. But how does an advisor help people whose incomes swing up and down, year after year? When the money is rolling in, how does an advisor keep a client from looting the entire windfall?
Planners who specialize in working with writers, artists, athletes and entrepreneurs preach a consistent mantra of savings, savings, savings. They also help their clients make lifestyle choices that can be maintained for decades and manage client expectations to help avoid the unwise decision that a big paycheck can support a new way of life.
"While retirement savings is important for all, it's particularly important for people with a variable income stream," says Phillips Ruben, a CFP in Newton, Mass., whose clients include writers, artists, teachers and entrepreneurs.
Ruben helps his clients maximize their savings, inject some discipline into their lives and keep spending at bay. Planners who work with this crowd must also understand that there may be years when such clients will not be able to contribute to their retirements, he says. "Money is a secondary consideration in realizing a dream in becoming an artist," he says.
He urges people pursuing their artistic passions to be open to having a regular income - taking teaching jobs, perhaps, or working part-time in family businesses. The goal is to "at least alleviate some financial pressure if there's some regular income coming in."
Entrepreneurs are a special case: Although they tend to be quite accepting of financial risk in their business lives, he says, they are more risk-averse when it comes to investments. "They worked so hard for their money," Ruben says. "I tend to be more conservative in managing the assets they do have, so there are no wild swings in the portfolio."
He suggests to his clients: "Find a sustainable lifestyle that you're comfortable with. Define a reasonable, sustainable lifestyle and stick with that." Living below their means helps "so when times are bad they don't have to ramp down their lifestyle."
John Valleau, a financial planner in Chicago, sees his job working with actors and entrepreneurs as "trying to add structure to their lives." He has a stable of voice-over artists, jingle singers and music producers who find steady work through advertising agencies. Valleau helps them apply the same diligence to their finances.
"To be successful with an uneven income you've got to live below your means, because you have to have more of a cash cushion than an employee," Valleau says. "You may go months at a time before the next job. You may make a ton of money for next five months and nothing for a year."
To create that structure, Valleau, a principal at ShankerValleau Wealth Advisors, asks each of his artists and entrepreneurs to create corporations so that expenses are deducted directly through those entities. He directs his clients to create separate bank accounts for their businesses and pay themselves a monthly salary, rather than just raiding the business account every time cash is needed. "You'd be surprised how many people commingle everything and then it all gets mixed up and you don't have that discipline," he says.