5 Things to Know if You Have Stock Options
Included:
• 3 different types of options
• How to know when to sell
• Terms to know
• How to reduce risk
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If you've been dreaming about early retirement in the San Ramon/Bay Area, you're in good company. Professionals in their 40s, 50s, and early 60s—especially those in tech, are increasingly trading commutes and the corporate grind for passion projects, travel, and personal fulfillment. But retiring early in one of the most expensive regions in the U.S. requires more than just savings—it takes strategy, savvy tax planning, and serious clarity about your goals.
The concept sounds alluring. But is early retirement in the Bay Area a ticket to freedom—or a financial misstep waiting to happen?
People here aren’t just chasing a fantasy—they’re responding to burnout, job volatility, and a growing desire for time autonomy. The pandemic made many reevaluate priorities. The average 50-something engineer in San Ramon isn’t just tired—they’re thinking: “What if I only have 20 good years left? Shouldn’t I spend them how I want?”
Silicon Valley’s demanding culture doesn’t age gracefully. Long hours, constant upskilling, and ageism often leave experienced professionals feeling squeezed. So, the appeal of stepping away is real—especially for those with equity windfalls or high savings rates.
The FIRE(Financial Independence, Retire Early) movement has a significant following here, but it's a different game when you're trying to FIRE in a zip code with$2M homes and $12 avocados. Still, with smart planning, it's not impossible.
The Bay Area consistently ranks among the top for cost of living. Housing, healthcare, groceries—all significantly higher than national norms. That means yourretirement dollars simply don’t go as far.
Let’s consider this: retiring in Texas with $3M might make you feel rich. In San Ramon? That could be middle-class at best.
Inflation isa retirement killer—and it compounds over time. Add to that the reality that you might live to 90 or beyond, and you’re looking at funding 40 years of living expenses. That’s a long time without a paycheck.
They had$4.2M in net worth and assumed they were safe. But after accounting for taxes, inflation, market risk, and healthcare, their planner told them they needed to scale back spending or risk running out of money by age 83.
What are the biggest tax pitfalls in early retirement?
Failing to plan for capital gains, early withdrawal penalties, and suboptimal Roth conversions can cost you six figures.
Should I move out of California to retire early?
Many do. States like Nevada, Arizona, and Oregon offer lower taxes and cost of living—but emotional and lifestyle considerations also matter.
Is health insurance affordable before Medicare?
Not always. Expect to pay $1,200–$2,500/month for a couple, unless you qualify for subsidies.
How much should I budget monthly in early retirement?
That varies, but many Bay Area retirees aim for $10K–$15K/month, especially if staying local.
Can I retire early if I still have a mortgage?
Possibly. It depends on your other assets, interest rate, and comfort with risk. But for many, downsizing is a smart move.
Early retirement in San Ramon is not impossible—but it’s certainly not simple. It requires intentional planning, clear goals, a dynamic strategy for taxes and income, and sometimes, tough lifestyle choices.
Done right? It’s a beautiful second act in one of the most dynamic regions in the country.
Done wrong? It's a slow drain on savings with regret baked in.
The smarter move? Let us help you build a roadmap—with professional guidance—that lets you retire your way.
· Retire Smart in the Bay Area. A Financial Checklist for Professionals 50+
· 5 Big tax challenges of retirement planning
· Using Equity Compensation in Retirement Planning
· Retiring Early? How Volatility Impacts Savings
· Social Security Early Retirement Guide
The information contained herein is intended to be used for educational purposes only and is not exhaustive. Diversification and/or any strategy that may be discussed does not guarantee against investment losses but are intended to help manage risk and return. If applicable, historical discussions and/or opinions are not predictive of future events. The content is presented in good faith and has been drawn from sources believed to be reliable. The content is not intended to be legal, tax or financial advice. Please consult a legal, tax or financial professional for information specific to your individual situation.
Included:
• 3 different types of options
• How to know when to sell
• Terms to know
• How to reduce risk
Helping busy professionals simplify their financial lives
2603 Camino Ramon, #200
San Ramon, CA 94583
925-271-9331
paul@collabriacapital.com
