Financial Milestones for Every Age: A Retirement Roadmap

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Hunter discussing financial milestones.
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What better birthday gift than to let a friend or family member know they’ve hit a new tax or retirement milestone? In this video, we’re going to run through the major tax and retirement milestone ages. Hi, I’m Hunter Brockway, founder of Boca Retirement Strategies, here to help set you up for a successful retirement while spending more money and avoiding being killed in taxes. If you’d like to skip through this video to a particular age, we will break it up in the bookmarks, or you could join me for the ride and see if you knew each of these milestones, starting from ages 0 to 18, look for opportunities to leverage kitty tax rules, especially for business owners. At age 18+, carefully watch and document requirements for continuing to claim adult children as dependents. Age 18 to 20, state-specific, prepare for UTMA and UGMA investment accounts to revert to the adult child’s legal control. At age 26, prepare for adult children to fall off of parents’ health insurance plans.

Retirement Planning for Middle Age At age 50, adjust or increase contributions to retirement plans like 401(k)s, IRAs, and Roth accounts to capture increased catch-up contributions. At age 55, you are eligible for HSA catch-up contributions. Also, at age 55, review company retirement plans for the option to take an in-service distribution or roll over to an IRA account. Also, for 55, evaluate the ability to retire early and access applicable retirement accounts without the 10% early distribution penalty (that does not apply to IRA or Roth Accounts). At age 59 and a half, begin evaluating penalty-free distributions from retirement plans, IRAs, and Roth accounts.

Understanding Social Security Benefits At Age 60, if applicable, evaluate when to claim Social Security widow benefits. Remember, the same taxation rules apply to all non-minor Social Security benefits. At age 62, this is the earliest age for you to claim your own social security benefit. You can evaluate the best strategies for claiming Social Security benefits and the related tax issues. We also have a video on that; you can check the description below for that link.

Medicare and Full Retirement Age At age 65, you’re eligible to claim Medicare and begin watching for the means-tested Medicare penalty if your income exceeds certain limits. Age 67, full retirement age for Social Security claiming.

Planning for Required Minimum Distributions Around age 68, begin planning for required minimum distribution starting in a few short years. Roth conversions are often the best hedge. Age 70 is the max social security benefit age. Age 70 and a half, if charitably inclined, begin using untaxed IRA dollars for all eligible charitable contributions, officially known as Qualified Charitable Distributions or QCDs. You can check the description below for our video on QCDs. Between ages 73 and 75, depending on when you were born, begin taking required minimum distributions. Mistakes can result in a 25% penalty.

So, there you have it, a lifetime of tax strategies laid out within a couple of minutes. You can imagine how much I nerd out when working with clients for years. Take action, note your next retirement milestone, and incorporate it into your 10-year tax plan. I’m Hunter Brockway, founder of Boca Retirement Strategies. If you’d like an individualized financial plan to include a tax plan, you can book at no cost, no obligation call on our website at or email us at We are based in South Florida, Western Massachusetts, and work with clients scattered throughout the US. Enjoy your successful retirement, and thank you for watching. Bye!

One last thing, we are also slowly setting up a retirement mastermind group I am calling RetireMentality. If you don’t know what a mastermind group is, it’s a group of like-minded individuals getting together to help each other solve common problems. We plan to run this group in a roundtable format so peers can help each other. We might talk about things like healthcare, travel, local effects. If you are interested in joining this group, you can send me an email at This will be a completely anti-sales group designed purely for helping you help others retire.

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