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Big Questions for Money Moments

Now that I’ve received a windfall, I’d like to take some time off from working and potentially work differently going forward. Can I do that? How should I think about it?


Money is a means to an end, not an end in itself. We believe priority should be given to identifying ways to enjoy it and use it as a tool to accomplish other life goals or objectives. For some, taking time off from work to travel or simply change gears for a while is top of mind.

For others, the ability to work differently, such as start a company, work in an entrepreneurial setting, or change industries, would be a dream come true. Often, all of these options are completely doable. The key is to work with an advisor to help you outline a clear picture as to what it will look financially and determine what works and what doesn’t.

We find that financial modeling of various scenarios (including stress testing) around life expectancy, investment returns, and income and spending assumptions, etc., can serve as an effective roadmap and help clients make big decisions with confidence. In addition to solving the money equation, it’s also important to think through and successfully navigate insurance coverage, tax withholdings, and logistics around cash flow from month to month during a work hiatus. Moreover, low-income years may present financial planning opportunities, such as taking advantage of Roth IRA conversions at low tax rates or reducing a concentrated stock position at more favorable capital gains tax rates. You’ll want to work with someone who is not only equipped to help you plan for the long term but also proactive year-to-year to help you take advantage of tax and other planning opportunities along the way.

Cerity Partners LLC (“Cerity Partners”) is a registered investment adviser with offices in California, Colorado, Florida, Illinois, Ohio, Michigan, New York, Massachusetts, and Texas. Registration of an Investment Advisor does not imply any level of skill or training. This commentary is limited to general information, and should not be construed as personal investment advice. There is no guarantee that the views and opinions expressed in this piece will come to pass. The information is deemed reliable as of the date of this commentary, but is not guaranteed, and subject to change without notice. It should not be considered as an offer to sell or a solicitation of an offer to buy any security.

Meet the Author

Aaron Waxman


Aaron is a Partner based in the San Francisco office. He provides comprehensive investment and planning advice to individuals. While Aaron works with a wide array of clients, he has expertise in working with multigenerational families, business executives, and entrepreneurs with above average income and estate tax planning needs.

Before joining Cerity Partners, Aaron was a Principal at B|O|S and served on the firm’s Board of Managers, strategizing firm-wide initiatives and making critical decisions on the day-to-day functioning of the firm. Prior to B|O|S, he worked for PricewaterhouseCoopers LLP as a Manager in the Private Client Services Group.

Aaron placed on the Forbes “Best-In-State Wealth Advisors” list for the San Francisco region in 2019, 2020, and 2021. In 2019 he also ranked on Forbes “Top Next-Gen Best-in-State Wealth Advisors” list for California and on its “Top Next-Gen Wealth Advisors” list. Additionally, in 2017, Aaron was the recipient of a “40 Under 40 Award” by the San Francisco Business Times.

Aaron earned his Bachelor of Science in Finance from Santa Clara University. He holds both the Certified Financial Planner (CFP®) and Certified Public Accountant (CPA) designations as well as a Series 65 license. Aaron is a member of the Stern Grove Festival Association Board of Directors. He previously served on the Board of Directors for the Headlands Center for the Arts, Step One School, and Blind Babies Foundation.

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