When Too Much Tax Deferral Becomes Counterproductive
Most of us have been told from early on in our careers to defer as much income as possible to ensure we’ll be properly prepared for retirement. While not bad advice, most of these strategies involve only qualified deferrals, meaning all income tax gets punted until the distribution phase. Now, if you end up in […]
Simplify Budgeting to One Key Number
“Where does the money go?” is a question we, unfortunately, hear all too often when discussing budgeting and cash flow. Often the only thing simple about a family’s cash flow is that it is simply confusing. Let’s look at how we help simplify complicated family finances into one key number. Often times we see clients […]
Student Loan Forgiveness Best Practices
Key Takeaways: Federal student debt cancellation up to $10,000 ($20,000 for Pell grant recipients) Cancellation limited by income ($125,000 single, $250,000 for married couples) Limited PSLF Waiver ends October 31, 2022; review your eligibility This past Wednesday, the President announced a student debt cancellation plan. Unfortunately for borrowers hopeful to log in to their […]
A History of the Individual Income Tax in America
Key Takeaways: Taxes have been part of our country’s history from the very beginning – No Taxation Without Representation! Some have said that the only two constants in life are death and taxes. Today, the tax code has become so complex that you could spend as much time as you wanted to be buried in resources […]
Most Couples Shouldn’t BOTH Delay Social Security

Key Takeaways: Two-income households have more complex Social Security timing decisions The higher-earning spouse generally benefits from delaying payments The lower-earning spouse generally benefits from starting payments early We’ve written a previous breakdown on the Social Security timing decision. Briefly, between ages 62-70, if you delay taking income, your monthly benefit grows. We discussed that […]
Tax Savings on Company Stock
If you work for a publicly traded company, chances are you can own company stock inside your 401(k) retirement plan. We’ve seen many workers nearing retirement who have accumulated substantial shares of company stock. These workers are often unaware that they have an option with the tax treatment of these shares that could potentially result […]
Putting a Value on Your Social Security Benefits
Key Takeaways: Most retirees don’t think of Social Security as an asset and therefore exclude it from their balance sheet. The present value of Social Security payments over an average life expectancy can easily be several hundred thousand dollars. We can’t predict what will happen with Social Security down the road, so it is important […]
Evaluating the Benefits of Flex Spending and Health Savings Accounts
Most employees face countless and confounding options each year when they select their benefits. There is no unanimous choice in any benefit area, it really comes down to what the employee needs and will benefit from most, particularly long-term. Flex spending accounts and health savings accounts are very common options these days, particularly as employers […]
Takeaways From a Week at the Chicago Booth School of Business
As all the children in our community are getting ready to go back to school, I am reflecting on my week back in the classroom this summer. I was lucky enough to spend time at the Chicago Booth School of Business learning from the country’s leading practitioners in estate and tax planning. Earlier this year, I set […]
Social Security: Whether to Wait to Start Taking Retirement Benefits
Key Takeaways: You could be facing up to a 30% reduction in your PIA by taking Social Security retirement benefits at age 62. By waiting until age 70, your retirement benefits will be roughly 32% higher than your PIA. The breakeven for taking Social Security retirement benefits at age 70 compared to age 66 is […]
Social Security Income: Not-So-Simple Basics
When I first started writing this article, my introductory sentence was “Social Security on the surface is a very simple concept.” However, as I began to write about all of the “simple” information, I have to conclude that Social Security is not very simple at all if you are not continually dealing with it. Below, I […]
Educating Your Next Generation
Key Takeaways: Our most successful planning relationships are those in which we work with our client’s other professional advisors – and their children and heirs as well. Involving heirs in your financial and estate planning makes the next generation’s estate administration job much easier. You do not have to tell them every detail, but at […]