Thoughts on a Thriving Life

In 1991, land use attorney Timothy Tosta was on fire. The 41-year-old attorney had a wildly successful practice, a reputation for sealing some of San Francisco’s most impossible development deals, and a future that could only get bigger. On the cover of a 1988 edition of California Executive, the attorney appears under the headline “Tim Tosta: Pit Bull or Polly Pure?,” his face revealing both his determined nature and youthful demeanor.

Then he received a phone call from his dermatologist with news that the lump on his back was a malignant melanoma. Tosta, father of three children under the age of 10, was told he had two years to live.

Tosta speaks openly of his brush with mortality, recalling the weeks after the prognosis. “It was basically a blur of dread and sadness,” he says. He underwent surgery and came out to receive some unlikely good news. The tumor had been removed with “clear margins,” indicating the melanoma might not have metastasized. “I felt that my death sentence had been commuted, and I would never look at life the same way again,” he says.

Since the initial surgery, Tosta has had two melanomas, both caught early enough so as not to pose a substantial risk.

Today, an enthusiastic Tosta sits in his office at Luce Forward, brewing and pouring green tea into delicate Japanese cups. There are few spills despite Tosta’s booming laughter and lively gestures.

“I used to be so focused on my career that I would actually say to myself, ‘I’ll live my life later,’” he says. Now 61, Tosta is singing a different tune. Literally.

“The first thing I did after I was told I had two years to live was go out and get a guitar,” he says. Along with playing music, Tosta meditates, practices yoga and studies philosophy and mysticism. He spends time with his family. He volunteers weekly in the hospice ward at Laguna Honda, a public hospital serving San Francisco’s indigent population, and has written a series of stories based on his experience called Lessons for the Living, along with the recently published book #DEATHtweet: A Well-Lived Life through 140 Perspectives on Death and Its Teachings.

Concerning his career, Tosta is resolved to use what he’s learned about life and bring it into his practice.

“I’ve started to see the legal profession as similar to Aikido,” he says. Both hone the ability to absorb and use the energy of one’s opponent rather than fight it. “If you can really take in the ideas from the other side of the table without the emotion and battle mentality, not only can you understand your own position more clearly, but you have a better chance of coming to a successful solution. The conflict becomes opportunity for collaboration and creativity,” he says. 

Tosta’s approach is paying off and affecting others. A certified life coach, Tosta speaks frequently at legal events, including conferences for the California State Bar Real Property Law Section and the Urban Land Institute. He encourages his audience to use self-inquiry to find meaning in work and to transform a career into an expression of compassion and purpose.

Tosta also writes a column for the Daily Journal, blending his real-life legal and personal experiences with notes from positive psychology, coaching, sociology and science. The articles appear in a collection titled Thoughts on a Thriving Life.

A Santa Cruz native, Tosta was born across the street from the ocean in the same hospital where his mother was born. His father owned an auto-parts business, and his mother was a homemaker. It was a quaint upbringing. “I just thought everybody grew up riding their bikes down to the beach to surf before first period at school,” he says.

Then, in 1967, en route to his first semester at Princeton, Tosta landed in Newark. “The city was literally burning,” the attorney recalls. “The National Guard was there and it was complete chaos.” Tosta was wide-eyed. And hot. “My parents thought I should be well-dressed when I arrived at college, so I was in a heavy wool three-piece suit in July.”

Things cooled off for him once he made it to campus, where he immediately felt at home. “I had always been plagued by being identified as a smart kid,” he explains, “but at Princeton I was allowed to dive into that aspect of myself to the fullest.” Tosta soaked up everything from religion and music theory, to sculpture, foreign language and architecture.

He went on to law school at Boalt. While other students spent summers interning with big firms, the young maverick worked for the Coast Guard. And at 24, fresh out of law school, without knowing anyone in San Francisco, Tosta rented an office in Jackson Square and started his own law firm. “If you want to fall on your face, go rent an office straight out of law school,” he laughs. But through a fortuitous partnership with an accountant, and some youthful tenacity, he was soon working with a number of medical doctors interested in investment opportunities in real estate.

A few years later, Tosta found himself representing a large-scale developer in a bid to build a 1,000-room Ramada Hotel in the Tenderloin. Amid competition with two other large hotel projects and an outcry of community activists, Tosta negotiated a cutting-edge deal that accommodated all parties involved, including the competition, and created permanent affordable housing in the area.

“I was into being the first one to do something—the power of the original idea is where the momentum comes from,” he says.

Tosta since has procured land use entitlements for some of California’s most complex and controversial development proposals in some of the state’s most treacherous political environments. The list of his successes is staggering, and includes negotiations for Rincon Center, the Infinity and 1.3 million square feet of development in Santa Fe.

When the entitlements that he’s procured face a courtroom battle, Tosta, though conciliatory, doesn’t back down. He represented developer Jack Myers in a battle with the Transbay Joint Powers Authority over 80 Natoma Street, and argued before the California Supreme Court in Citizens of Goleta Valley v. the County of Santa Barbara, one of California’s most significant Environmental Quality Act cases.

“I love this part of the law—it involves politics, community, culture, architecture, environmental issues and species protection,” he says. During the past several years, Tosta has even found that his hospice work come into play. “It might sound like a stretch,” he says, “but in my work I’ve seen that people’s response to large-scale development has reflected the same kinds of fears that I saw in people who were dying.” Tosta encourages his legal clients to approach a community with the intention to engage and listen. He jokes about the “aggressive, hormonal, take-over-the-world attorney” of his younger years, and says, laughing, “I know where my buttons are now—if I start to swear a lot then I’m out of my range.

 “I really don’t think this career was created so we could have a bunch of jerks in the room,” he says. “I think the job of a lawyer is to listen, be wise and mostly importantly, to be of service.”

CORRECTION

The article that ran in our print magazine incorrectly stated that Timothy Tosta worked for the Coast Guard. Rather, he was employed by the Coastal Commission. Furthermore, the land use entitlement for the development stated in the article as Santa Fe, N.M., is located in San Jose, Calif.

We regret these errors.