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Microsoft Retirement, Microsoft Early Retirement, Microsoft 55/15 Rule, Microsoft RSUs, Microsoft Tax Tips Glenn Rossman Microsoft Retirement, Microsoft Early Retirement, Microsoft 55/15 Rule, Microsoft RSUs, Microsoft Tax Tips Glenn Rossman

Early Retirement for Microsoft Employees: Pros & Cons

Microsoft doesn’t set a retirement age — you can leave when you’re ready. For some, “ready” means as early as 55, especially with benefits like the 55/15 rule for RSU vesting. But while early retirement can mean freedom and fresh starts, it also comes with some risks and trade-offs.

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Microsoft Retirement, Microsoft Phased Retirement, Microsoft Roth IRA, Microsoft Deferred Compensation Plan, Microsoft RSUs Glenn Rossman Microsoft Retirement, Microsoft Phased Retirement, Microsoft Roth IRA, Microsoft Deferred Compensation Plan, Microsoft RSUs Glenn Rossman

Financial Tips for Phased Retirement from Microsoft

For longtime Microsoft employees, retirement isn’t always an all-or-nothing decision. Many professionals want to step away from full-time work but aren’t quite ready to retire completely. Fortunately, Microsoft employees have several options to ease into retirement and make a smooth exit. Here are some financial strategies to help you phase out of Microsoft on your own terms.

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Microsoft Retirement, Microsoft Delayed Retirement, Microsoft RSUs, Microsoft Deferred Compensation Plan Glenn Rossman Microsoft Retirement, Microsoft Delayed Retirement, Microsoft RSUs, Microsoft Deferred Compensation Plan Glenn Rossman

The Hidden Costs of Delayed Retirement at Microsoft

For many longtime Microsoft employees, the company has provided a fulfilling career, strong financial rewards, and valuable benefits. But as retirement approaches, an important question arises: When is the right time to leave?

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Microsoft Retirement, Microsoft Rule of 55, Microsoft Early Retirement, Microsoft RSUs, Microsoft 55/15 Rule, Microsoft 401(k) Glenn Rossman Microsoft Retirement, Microsoft Rule of 55, Microsoft Early Retirement, Microsoft RSUs, Microsoft 55/15 Rule, Microsoft 401(k) Glenn Rossman

Microsoft’s Rule of 55 and Early Retirement

For employees hoping to retire early, Microsoft’s “rule of 55” offers some major benefits. This rule lets long-term employees keep vesting their unvested stock awards even after leaving the company. This can be a game-changer for your retirement income, especially when paired with smart 401(k) withdrawals.

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Microsoft Retirement, Microsoft Stock, Microsoft RSUs, Microsoft ESPP, Microsoft Tax Tips Glenn Rossman Microsoft Retirement, Microsoft Stock, Microsoft RSUs, Microsoft ESPP, Microsoft Tax Tips Glenn Rossman

Tax-Smart Tips to Sell Microsoft Stock for Retirement

As a Microsoft employee, your nest egg probably features plenty of company stock. While MSFT is a great stock choice, it’s always wise to diversify. But what about the tax bite from selling shares? Here’s how to exit Microsoft stock in 2025 without a major tax hit to your retirement fund.

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Microsoft Retirement, FIRE Movement, Microsoft Early Retirement, Microsoft RSUs, Microsoft ESPP, Microsoft 401(k), Microsoft Tax Tips Glenn Rossman Microsoft Retirement, FIRE Movement, Microsoft Early Retirement, Microsoft RSUs, Microsoft ESPP, Microsoft 401(k), Microsoft Tax Tips Glenn Rossman

The FIRE Movement for Microsoft Employees: Retiring Early

Retiring early might sound like a pipe dream, but for many high-earning professionals, it’s entirely possible with the right strategy. That’s where the FIRE movement comes in.

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Microsoft Retirement, Microsoft Tax Tips, Donor-Advised Funds, Microsoft Employee Giving Program, Charitable Remainder Trusts, Charitable Lead Trusts Glenn Rossman Microsoft Retirement, Microsoft Tax Tips, Donor-Advised Funds, Microsoft Employee Giving Program, Charitable Remainder Trusts, Charitable Lead Trusts Glenn Rossman

Smart Giving: Tax-Efficient Charity for Microsoft Employees

While writing a check for charity might feel good on its own, it isn’t always the best way to support your favorite causes. As a Microsoft employee, you have a unique opportunity to help the world through tax-advantaged charitable donations. Here’s how to give more effectively, optimize your taxes, and integrate real-world philanthropy into your broader financial plan.

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Microsoft Retirement, Microsoft Tax Tips, Microsoft RSUs, Microsoft ESPP, Microsoft 401(k), Microsoft Roth IRA, Microsoft Stock Glenn Rossman Microsoft Retirement, Microsoft Tax Tips, Microsoft RSUs, Microsoft ESPP, Microsoft 401(k), Microsoft Roth IRA, Microsoft Stock Glenn Rossman

6 Costly Tax Traps for Microsoft Employees to Avoid

Working at Microsoft comes with some serious financial perks, from stock awards to great retirement benefits. But with those perks come some sneaky tax traps that can catch you off guard if you’re not careful. Without a solid tax plan, you could end up owing more than expected.

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Microsoft Retirement, Microsoft Tax Tips, Microsoft ESPP, Microsoft Mega Backdoor Roth, Microsoft Roth IRA, Microsoft HSA, Microsoft RSUs, Microsoft Deferred Compensation Plan Glenn Rossman Microsoft Retirement, Microsoft Tax Tips, Microsoft ESPP, Microsoft Mega Backdoor Roth, Microsoft Roth IRA, Microsoft HSA, Microsoft RSUs, Microsoft Deferred Compensation Plan Glenn Rossman

Tax Tips for High-Income Microsoft Professionals

For high-earners at Microsoft, tax optimization is more than just a good idea — it’s a financial necessity. With the right strategies, you can significantly reduce your tax burden while growing your wealth.

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Microsoft Retirement, Microsoft Level 67, Microsoft Deferred Compensation Plan, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP Glenn Rossman Microsoft Retirement, Microsoft Level 67, Microsoft Deferred Compensation Plan, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP Glenn Rossman

What Reaching Level 67 at Microsoft Means for Your Finances

Reaching Level 67 is a major career milestone at Microsoft. This advancement brings additional compensation and new ways to save for the future. Here’s what you should know.

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Microsoft Retirement, Microsoft Pension, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft Deferred Compensation Plan, Microsoft ESPP, Microsoft HSA Glenn Rossman Microsoft Retirement, Microsoft Pension, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft Deferred Compensation Plan, Microsoft ESPP, Microsoft HSA Glenn Rossman

Does Microsoft Have a Pension Plan? [2025]

Understanding your Microsoft retirement plan is key to saving more. Here’s what to know.

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Microsoft Retirement, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft Deferred Compensation Plan, Microsoft ESPP, Microsoft HSA, Microsoft Tax Tips, Donor-Advised Funds Glenn Rossman Microsoft Retirement, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft Deferred Compensation Plan, Microsoft ESPP, Microsoft HSA, Microsoft Tax Tips, Donor-Advised Funds Glenn Rossman

How to Optimize Your Taxes as a Microsoft Employee

As a Microsoft employee, your benefits package can significantly reduce your tax debt for the year. Here's how to make the most of these opportunities.

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Microsoft Retirement, Microsoft 401(k), Microsoft RSUs, Microsoft ESPP, Microsoft Deferred Compensation Plan, Microsoft Tax Tips Glenn Rossman Microsoft Retirement, Microsoft 401(k), Microsoft RSUs, Microsoft ESPP, Microsoft Deferred Compensation Plan, Microsoft Tax Tips Glenn Rossman

Estate Planning Guide for Microsoft Employees

Estate planning ensures that your wealth is managed and distributed according to your wishes. When planning your estate, Microsoft’s unique compensation structure takes special consideration.

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