Milestone Money

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But the most important financial decision we will ever make is when and how to retire. For many, the word "retirement" conjures up endless green golf courses or blissful afternoons with grandkids, but we know that this reality doesn't just happen. Retirement is an iterative process that actually requires careful preparation and ongoing planning. Which investments should you sell to fund various li

Couples’ Financial Planning: Creating a Shared Path Forward - Milestone Money 02/03/2026

While money may not be the most romantic topic, neither are the arguments that often arise because of poor communication around household finance and investments. Commingling of funds, saving vs. spending, and investments are topics that every couple should discuss if they want to maintain healthy finances and a healthy relationship.

Couples’ Financial Planning: Creating a Shared Path Forward - Milestone Money Learn how couples can align values, improve financial communication, and build a cohesive long-term wealth strategy together.

Guide to IRA Types: Traditional, Roth, SEP & SIMPLE 11/11/2025

Since 1974, when the individual retirement account (IRA) was created by Congress, these accounts have become a mainstay for many individuals who want to save for a more secure retirement. Since their creation, however, IRAs have received many refinements and additions, making them an even more versatile tool for long-term savings. Milestone Money founder Randy Dippell provides some helpful basics.

Guide to IRA Types: Traditional, Roth, SEP & SIMPLE Learn about the 4 main IRA types and their tax benefits. Discover which retirement account—Traditional, Roth, SEP, or SIMPLE IRA—is right for you.

07/09/2025

Retirement planning doesn’t have to be overwhelming. At Milestone Money, we focus on making the process simple, clear, and effective—so you can feel more confident about your future and focus on what matters most.

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2000 N Racine Avenue , Suite 2180
Chicago, IL
60614