Wealth Management Insights

Kristin McKenna, CFP® covers a range of financial planning and investing topics with an emphasis on stock options and sudden wealth events.

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Stress testing a financial plan
Financial Planning

Stress Test Your Retirement Income Plan

Don’t stress out about every headline, stress test your retirement plan instead.  Markets move every day and the news cycle is 24-7. Unfortunately, headlines often leave investors wondering what the news means for their portfolio and financial outlook. We can’t predict the future, but we can control how we prepare a

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Fee-only fiduciary wealth management near me
Choosing a financial advisor

How to Find a Fee-Only Financial Advisor

When starting to search for a financial advisor, investors may not realize the different types of advisors out there…and they’re not all trying to sell you something. If you’re looking for a fee-only financial advisor or wealth manager, it’s probably because you know fee-only advisors don’t sell products. Finding the

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Live off dividends
Early Retirement

Can You Live Off Dividends In Retirement?

The idea of living off dividends in retirement sounds nice, but investors often don’t realize how much money they’ll need invested to generate enough income from dividends to cover lifestyle expenses. Over the last 30 years, the S&P 500’s average dividend yield was 1.98%.¹ So historically, every $1 million invested

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financial advisor for executives
Stock options

Exercising Stock Options

When’s the best time to exercise your stock options? With stock options, employees have the right (not obligation) to buy the shares. When you exercise your stock options you purchase company shares. Though early exercises are possible, the default setup is for employees to first have the options to exercise

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How to buy a new home before selling the old one
Mortgages

7 Ways to Buy a New Home Before Selling Your Current House

Can I buy another house before I sell mine? Updated for 2025. Because who wants to move twice? To buy a new house while selling yours (or selling and buying a home at the same time), you need cash and potentially the ability to carry two mortgages. Although challenging, here

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Best thing to do with inherited money
Inheritance

What’s The Best Thing To Do With A Large Inheritance?

After receiving a large inheritance from a loved one, you may wonder: what’s the best thing to do with it? As you consider what approach is right for your situation, it’s important to understand the complexities of managing a financial windfall and the various ways an inheritance can be taxed.

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How stock options are taxed
ISOs

How Stock Options Are Taxed: ISO vs NSO

Tax implications of exercising and selling stock options If you have stock options as a large part of your income, taxes are especially important. There are two types of stock options: incentive stock options and non-qualified stock options. How stock options are taxed depends on the type of options you

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Wealth Management Needham MA
Retirement Planning

Why Non-Deductible IRA Contributions Aren’t Worth It

Updated for 2024 – 2025. Investors often ask: should I be making nondeductible IRA contributions? In the vast majority of cases the answer is no. Why non-deductible? Because many taxpayers earn too much to make pre-tax IRA contributions as they have a 401(k) at work. Although any investor with earned

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Qualified Small Business Stock - Section 1202
Business owners

Qualified Small Business Stock: The Section 1202 Gain Exclusion

Includes QSBS changes from the July 4, 2025 OBBB tax bill. If you invested in a startup or small business (founders, employee exercise of stock options, business owner), you need to know about qualified small business stock. If eligible, you may be able to exclude up to 100% of the gain

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Fiduciary Investment Advisor
Choosing a financial advisor

How to Find a Fiduciary Financial Advisor

Looking to find fiduciary financial advisors and wealth managers? Only fiduciary advisors are legally bound to act in your best interest at all times. Here are five ways you can find a full-time fiduciary financial advisor. What is a fiduciary advisor? A fiduciary advisor is a financial professional who is

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How are stock options taxed
Tax planning

2025 IRS Contribution Limits For IRAs, 401(k)s & Tax Brackets

The IRS released the 2025 401(k), 403(b), and SEP IRA contribution limits, including a new special catch-up contribution for workers age 60 to 63. The IRA and Roth IRA contribution limits are unchanged but income eligibility for tax-deductible IRA contributions and Roth IRA contributions have changed. Also updated: health savings

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Financial advisor for stock options
Investing

How Often Should You Rebalance Your 401(k)?

Rebalancing your 401(k) and investment portfolio is an important part of a successful investment strategy. Your asset allocation is the percentage of your portfolio that you distribute between different asset classes, like stocks and bonds. Without periodic rebalancing, your investment mix will change as the market fluctuates, falling out of

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Wealth Management for Executives
Business owners

What To Do With The Money From The Sale Of Your Business

Selling your business for cash? Deciding how to allocate and invest the proceeds after the sale of your company is a big decision that requires careful planning. If you are expecting a sudden windfall, develop a plan to allocate the proceeds and reinvest in your future. As you weigh what

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stock options company bought out
Stock options

What Happens to Your Stock When a Company is Bought?

If your company (e.g. the target company) is getting acquired, you’ll want to understand what happens to your stock. When a company buys another company, what can happen to your stock depends on several factors, including if you own stock outright or vested/unvested stock options/RSUs. Here’s more on what happens

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Sudden Wealth Financial Advisor Invest a Windfall
Sudden Wealth

Sudden Wealth: Managing a Large Financial Windfall

Next steps after a sudden wealth event or cash windfall Wondering what to do with a sudden financial windfall? Whether the windfall was expected, perhaps from the sale of a business, or unexpected, you’ll want to build a team of professional advisors and make a plan for the future. While

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Retirement planning and tax planning to minimize tax on required minimum distributions
Estate Planning

Should I Put My Assets in a Trust? Top 3 Benefits of Living Trusts

Do I need a revocable living trust? Choosing whether to fund a trust with your assets is an important decision in the estate planning process. Since a trust is different from a will, many individuals need both. Here are three main reasons you may want to consider putting your assets

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