Retirement Education
Five Mistakes Pre-Retirees Should Avoid
“Pre-retiree” is too broad. Theoretically, everyone is either a pre-retiree or a retiree. For the purposes of this column, I’m defining a pre-retiree as a person in the final five years before retirement. In my experience, this is the point when a light bulb flashes,...
Ten Reasons To Stop Doing Your Own Taxes
I do not do my own taxes. That will shock a lot of my readers and clients who know that I own a business that offers tax planning and tax preparation. Also, I am an IRS enrolled agent, licensed to prepare taxes and represent taxpayers in front of the IRS. I did my own...
Four Situations That Call for a Second Opinion on Your Financial Plan
A financial plan should be just that, a step-by-step guide to what you need to do to reach your goals with your money. The irony is that financial plans go stale almost immediately. Goals shift. Assumptions change. Life is constantly moving. Two years ago, I would...
Strategies 6–10 for That Stock You Have Too Much Of
Seemingly every week now I have someone reach out with this “good problem.” Mary’s company went public last year and now makes up 60% of her balance sheet. John bought AAPL stock in the 90s and decided after the iPhone came out that he may just never sell. Today,...
Five (of Ten) Options for That Stock You Have Too Much Of
A childhood friend recently called me looking for some guidance post-IPO of the company she joined as an early employee. A dream! Employee stock used to be the most common reason I saw concentrated stock positions. Things have changed in the past four years as tech...
Three Reasons To Stay Put in Retirement
Recently, after putting down our 14-year-old dog, my wife and I took our kids to Florida as a sort of distraction trip. Immediately, it became evident that this income tax-free state was no longer any cheaper and, in many ways, was more expensive than the DC suburb we...
Four Ways to Avoid RMD Penalties
Vanguard just answered a question I’ve long had. A question only someone who lives and breathes retirement income planning, like me, would have: What percentage of people miss their required minimum distributions (RMDs) entirely or take less than the minimum amount?...
I Am Retired. Should I Hang On to My Rental Property?
On the list of things I hope to someday own, a rental property may just be last. My parents owned rental properties near a college campus in the early 2000s and through the global financial crisis. I still have nightmares from the maintenance calls that the world’s...
Three Ways to Plan for the Post Retirement Surge
In 2020 I spoke with a client who had lost much of her mobility. I asked her if she were to go back ten years, what she would have done differently. Her answer was simple, yet wise: “more.” Perhaps it was the fact that she couldn’t do what she was once able to....
Tax and Estate Planning Is the Main Dish for High-Net-Worth Retirees
I spend more time within our tax planning software and on the tax tab of our financial planning software than anywhere else in our tech stack. Significantly more time than I spend in our investment analytics tool. Probably the only thing I spend more client time on...
Why “I’ll Work Until I Die” Is a Terrible Plan
I recently met with a business owner who seemed less than thrilled to have this meeting that his CPA insisted upon. I used to ignore the elephant in the room in these situations but, with three young kids, I have little time to waste. I just asked why he was taking...
Five Things You Shouldn’t Do After You Sell Your Business
You did it. You just crossed the finish line of the longest, hardest race you’ve ever run. Probably the most fulfilling, too. There is a line of people like me around the corner offering you a whole host of products and services. It’s easy to say “yes.” Below are the...
Three Ways To Push Off RMDs
I started to focus on retirement income planning about fifteen years ago. One thing that stuck with me early in this journey was just how much our clients detested required minimum distributions (RMDs). I think a large part of this was the pre-covid, local nature of...
How To Make Sure Your Son-in-Law Doesn’t Get Your Daughter’s Inheritance
The awkward part of a prospective client’s planning meeting has arrived: the husband and wife are tiptoeing around the estate planning conversation. They look at each other, then back at me, and in unison say, “Well, we don’t love our ____.” I finish their sentence:...
Navigating Retirement Threats
In the retirement courses I teach, I always tell the soon-to-be retirees that getting to retirement is a volume game. Volume of savings, volume of returns and volume of time for those things to compound. As savings grow, so do the dollar values during market swings....
Should You Give Your Kids Stock Instead of Cash?
I recently wrote two surprisingly long and complicated columns on the strategies available today to minimize the tax hit that comes when you press the “sell” button on an appreciated stock. If you’ve just filed your taxes, you know the pain of capital gains is real,...
Four Ways Women Retire Differently
My wife and I don’t take the same vitamins. We don’t follow the same workout plan. We don’t have the same diet. The last one is on me. I should eat healthier food. Think of retirement planning for women and men as a daily vitamin. They should be different by design....
Four Terrible Times To Do a Roth Conversion
Roth conversions are trendy. So much so, that I know if I write on the topic, you’ll click. Welcome! There is a strong case for this powerful strategy, just as there is for Ozempic. But like Ozempic, Roth conversions aren’t for everyone. Here are situations where I...
Five Financial Items To Prioritize When Your Spouse Is Sick
In 2011, we brought on a client on the verge of retirement. Six months into retirement, her husband died of brain cancer. While the wife had what most people would consider to be an estate plan in place, the financial nightmare that followed the human tragedy totally...
Four Tax Changes if You Are in or Near Retirement
As of February 5, software stocks are getting annihilated. That is my highly technical description of companies, like Salesforce, that are sitting about 40 percent below their highs. The theory: AI is going to make these exorbitant subscriptions unnecessary. I am not...