Is your company stock helping you build freedom or holding you back?

You’ve spent years building a career in tech. Maybe you joined early, took the equity, and held on. The stock soared. Or maybe it is a mix of employers, pieces of your story tied up in each company’s ticker. What started as compensation has quietly become wealth.

Now, you’re sitting on a concentrated position and asking a smart question: What is the right move?

There is no single formula. But there is a better way to think about the problem, one that blends math with self-awareness.

The Hidden Risk in Loyalty

When we first met a client who had spent more than five years leading a team at a well-known tech firm, she had already seen her company through an IPO. When the pandemic hit, the stock price tripled. It felt like validation for years of work and long nights. She called it her "golden goose."

We recommended a plan to sell gradually and diversify, but the emotional pull was strong. Each quarter the stock climbed higher, and selling felt like walking away from potential. Recency bias told her the stock only went up. Then the momentum broke, and the company’s share price was suddenly worth half of what it once was.

That moment changed everything. Together, we reset. We chose a clear percentage of her net worth to hold long-term and agreed on annual price targets for sales. The goal was not to abandon her success but to protect it. A few years later, she used part of those proceeds to build her family’s dream home. Her wealth felt less like a windfall and more like a foundation.

Concentrated stock positions are often built on loyalty and optimism. You know the company. You have seen its wins and weathered its mistakes. Maybe you helped make it valuable. But markets do not reward familiarity. They reward diversification.

A single company’s stock can fall 30% in a day for reasons that have nothing to do with your talent or work ethic. Leadership changes, earnings misses, regulation…these are risks no employee can control.

When one stock makes up more than 10% of your liquid net worth, you have entered a zone where a single earnings call can change your financial trajectory. That is not a strategy. That is luck management. And wealth built on luck deserves protection.

The Tax Reality Check

Selling stock means paying taxes, and taxes create friction. It is tempting to delay action until “the right time.” But waiting is its own form of risk.

Here’s what matters:

Capital gains: Stock held for more than a year qualifies for lower long-term rates. Sell too soon and you will pay more.

Tax brackets: Large one-time sales can push you into a higher bracket. Strategic, phased selling can help keep you in a lower one.

Overlapping events: Option exercises, RSU vesting, and bonuses can all overlap, creating surprise tax bills.

Taxes should not dictate your plan, but they should inform it. That’s why we always recommend coordination between your CPA and your financial advisor before a single share hits the market. Once you sell, the decision is irreversible.

Smart Ways to Unwind

Different people have different comfort levels with concentration risk. The right approach balances discipline with flexibility.

Option 1: Gradual Selling

Sell portions of your position on a set schedule: monthly, quarterly, or annually. It smooths volatility and tax exposure while building momentum toward your goal.

Option 2. Tax-Loss Harvesting

If parts of your portfolio are down, those losses can offset the gains from selling concentrated stock. It is a tactical way to reduce your tax bill while rebalancing.

Option 3. Donor-Advised Funds (DAFs)

Charitably inclined investors can donate appreciated shares to a donor-advised fund, skipping capital gains taxes and taking an immediate deduction. You support causes you care about while reducing portfolio risk.

Option 4. Direct Indexing

Replace your concentrated stock with a custom-built portfolio that mirrors a broad index. You retain market exposure but eliminate single-stock risk. It is modern diversification, optimized for taxes.

When Selling Early Pays Off

Not every success story begins with a crash. Another client we worked with joined a tech company as an engineer before its IPO. Like many early employees, his RSUs became the core of his wealth. By the time we met, that single stock accounted for nearly three-quarters of his liquid net worth.

We built a plan together, setting price targets and defining a long-term goal for how much of his net worth would remain invested in the company. It was not an easy decision to sell. Every time the stock rose, headlines and peers reinforced the idea that holding meant winning. But he stayed disciplined. Over time, he sold in stages, reinvested into a diversified portfolio, and used the proceeds to take a sabbatical. He spent that time traveling, exploring new cities, and reflecting on what kind of work he wanted to do next, without the pressure of watching a stock ticker.

Two years later, the company’s share price is right back where it started on IPO day. The volatility in between could have easily shaken anyone’s confidence. Instead, his portfolio has grown, his net worth has increased, and his sense of calm is unmistakable. When he talks about it now, he says the clarity of his plan kept him grounded. The market may move, but his life moves with intention.

From Wealth to Freedom

Money tied to one company can feel exciting and a little dangerous. Selling can feel like giving up on a story that shaped you. But the goal is not disloyalty; instead, it’s independence.

Your concentrated position got you here. A thoughtful plan gets you to what’s next.

Maybe that is early retirement, a sabbatical, a new home, or the freedom to say yes to something that does not come with a paycheck. Whatever your goal, your stock is just the fuel. You are the driver.

At Mana, we help clients turn concentrated wealth into durable freedom, with clear strategies, careful tax planning, and deep alignment to what matters most.

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Stephanie Bucko and Cristina Livadary are fee-only financial planners based in Los Angeles, California. Stephanie is the Chief Investment Officer and Cristina is the Chief Executive Officer at Mana Financial Life Design (FLD). Mana FLD provides comprehensive financial planning and investment management services to help clients grow and protect their wealth throughout life’s journey. Mana FLD specializes in advising ambitious professionals who seek financial knowledge and want to implement creative budgeting, savings, proactive planning and powerful investment strategies. As fee-only fiduciaries and independent financial advisors, Stephanie and Cristina never receive commission of any kind. Stephanie and Cristina are legally bound by their certifications to provide unbiased and trustworthy financial advice.