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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, 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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Microsoft Retirement, Microsoft HSA, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP Glenn Rossman Microsoft Retirement, Microsoft HSA, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP Glenn Rossman

Planning for Healthcare in Retirement: 11 Tips for Microsoft Employees

Planning for healthcare expenses is a crucial part of any retirement strategy. For Microsoft employees, robust benefits can help build a strong foundation for retirement, but it’s essential to plan strategically. Here are key tips to prepare for a smooth and financially stable retirement.

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

Life After Microsoft: How to Plan for Retirement

The key to a comfortable retirement is planning ahead. From understanding your Microsoft retirement benefits to assessing your finances and making a budget, here are the steps you should take to build a better future.

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

Microsoft Compensation and Benefits Guide

Microsoft offers employees a great compensation package designed to attract and retain top talent. In this guide, we’re going to look at how Microsoft pays employees so you can make the most of your salary and benefits.

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Microsoft Retirement, Microsoft Early Retirement, FIRE Movement, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP, Microsoft Deferred Compensation Plan, Microsoft RSUs Glenn Rossman Microsoft Retirement, Microsoft Early Retirement, FIRE Movement, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP, Microsoft Deferred Compensation Plan, Microsoft RSUs Glenn Rossman

Microsoft Early Retirement Guide

Planning for early retirement is a major decision. As a Microsoft employee, how can you be sure it’s wise? Here’s what you should know.

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Microsoft Retirement, Microsoft 401(k), Microsoft Roth IRA, Microsoft ESPP, Microsoft RSUs, Microsoft Deferred Compensation Plan, Microsoft HSA Glenn Rossman Microsoft Retirement, Microsoft 401(k), Microsoft Roth IRA, Microsoft ESPP, Microsoft RSUs, Microsoft Deferred Compensation Plan, Microsoft HSA Glenn Rossman

25 Microsoft Retirement FAQs

As a Microsoft employee, understanding your retirement benefits will help you optimize your finances and plan for the future. Here are the answers to all your most common questions.

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Microsoft Retirement, Microsoft 401(k), Microsoft Roth IRA, Microsoft Mega Backdoor Roth, Microsoft ESPP, Microsoft Tax Tips, Microsoft HSA, Microsoft Deferred Compensation Plan, Microsoft RSUs Glenn Rossman Microsoft Retirement, Microsoft 401(k), Microsoft Roth IRA, Microsoft Mega Backdoor Roth, Microsoft ESPP, Microsoft Tax Tips, Microsoft HSA, Microsoft Deferred Compensation Plan, Microsoft RSUs Glenn Rossman

Maximizing Your Microsoft Retirement Benefits

Microsoft’s retirement benefits are some of the best in the tech industry. From a robust 401(k) to a generous employee stock purchase plan, employees have several opportunities to optimize their savings. Here’s a breakdown of the key retirement benefits and how to make the most of them.

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Microsoft Retirement, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP, Microsoft HSA Glenn Rossman Microsoft Retirement, Microsoft 401(k), Microsoft Mega Backdoor Roth, Microsoft ESPP, Microsoft HSA Glenn Rossman

How to Maximize Your Microsoft 401(k) Employer Match

As a Microsoft employee, you have access to one of the most generous 401(k) matching programs in the tech industry. If you aren't taking full advantage of this benefit, you’re leaving free money on the table. Here’s what you need to know to maximize your Microsoft 401(k) match and retire with more.

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