5 Planning Mistakes I See All the Time (and How to Avoid Them)

Avoid these common missteps

Simple shifts you can make today to avoid common pitfalls and build a stronger financial future.

One of the best parts of my work is getting to walk alongside people at all different stages of life, and I’ve noticed a few patterns that tend to pop up again and again. These aren’t major failures or irreversible decisions. They’re simply areas where a little more awareness (and a bit of planning) can make a big difference.

Here are five planning missteps I see often, and how you can stay ahead of them:

1. Assuming Your Accountant Is Handling Tax Planning

This one comes up a lot. Most people bring in a CPA during tax season, and that’s exactly what they’re focused on: getting your return filed accurately and on time. But filing your taxes is different from planning for them. Tax planning is about looking ahead and thinking strategically. It can help you decide when to sell stock, how to time retirement income like Social Security, or whether to shift savings into a Roth account. If you want to lower your lifetime tax bill, that kind of planning needs to happen proactively, and ideally year-round.

2. Waiting Too Long to Put an Estate Plan in Place

Estate planning often gets pushed off until there’s a health scare. But that’s rarely the best time to make big decisions. In fact, there are situations where it may be too late. To execute estate documents, you must be of sound mind. If someone is facing a serious diagnosis like dementia or has already begun experiencing cognitive decline, it may not be legally or practically possible to finalize their wishes.

Getting a plan in place early brings real peace of mind. A basic estate plan typically includes a will, health care directive, and power of attorney. For parents, this is also how you legally name guardians for your children, one of the most important (and most often delayed) decisions families make.

It’s not just about passing on assets. It’s about protecting your wishes and the people you care about most.

3. Overlooking Employer Benefits

It’s easy to gloss over your benefits packet during open enrollment, but doing so can mean leaving real money on the table. One of the most common examples is the 401(k) match. Many employers will match contributions up to 3% of your salary (sometimes more). If you’re earning $200,000 and not contributing enough to get the full match, that’s potentially $6,000 per year you’re walking away from. Over ten years, that could be more than $80,000 with compounding - all from just one missed opportunity.

I also see people miss out on things like Health Savings Accounts (HSAs), which offer triple tax benefits, or valuable after-tax contribution options that can allow for a mega backdoor Roth conversion. These features aren’t always well advertised, and even HR teams may not highlight them clearly. But they can make a meaningful difference in your long-term financial picture.

Taking the time to really understand your benefits, or reviewing them with a planner, can help you take full advantage of what your employer offers.

4. Not Keeping an Eye on Spending

It’s important to have a clear sense of where your money is going. Without tracking your spending, it’s easy for small expenses to add up without you noticing. One common example is lifestyle creep: when you get a raise or bonus, it might feel like you suddenly have more to spend. But by the end of the month, your bank account doesn’t reflect that extra income because little purchases quietly ate it up. Staying intentional about your spending helps you avoid this and keep your savings goals on track.

5. Not Thinking About Retirement Early Enough

Retirement planning can feel far off when you’re in your 20s or early 30s, but starting early makes a huge difference thanks to the power of compounding. For example, if you save $500 a month starting at age 25 and continue until age 67, assuming a 7% average annual return compounded monthly, you could end up with about $1.5 million.

But if you wait and start saving the same $500 a month at age 35 instead, you might end up with around $710,000 - less than half the amount.

That extra decade gives your money more time to grow, which is why even small contributions made early on can have a big impact over time.