The Brindle & Bay team has helped hundreds of families navigate the road to retirement. We know it can have potholes, detours, and misleading signs along the way. Just as there are certain clear tasks to complete in order to tee up a successful retirement, there are a number of things you should specifically not do.
Here are five common missteps we help our retirees avoid completely, as well as how to avoid them yourself.
1. Stop Treating Retirement Planning as a “One-and-Done” Task
Too many people treat their retirement plan like it’s a backyard chore: mow the grass, check the box, forget about it. But retirement isn’t static. It changes right along with your health, your values, the markets, and tax laws.
Think of your retirement plan more like a well-tended garden than a static, fixed document. It may require more work early on, but once the systems are in place — automatic withdrawals, investment allocations, tax strategies — it becomes easier to maintain.
That doesn’t mean you can neglect it, though! You’ll still want to:
-Monitor spending (are you over or underspending?)
-Check your portfolio allocation and rebalance regularly
-Stay on top of RMDs and tax-saving opportunities
-Adjust for life events (relocations, healthcare, etc.)
If you're already working with a financial advisor, they’re probably reviewing your plan every 3–6 months. That means you should at least revisit it annually, especially in the early years of retirement.
2. Stop Trying to Relive Your Peak-Earning Lifestyle
One of the most liberating truths about retirement is that you don’t have to live the way you used to. But many people cling to the identity and spending patterns of their peak earning years, sometimes at the expense of their own financial well-being.
We’ve seen clients trying to maintain (or even elevate) their lifestyle into retirement, even if it’s not financially sustainable. It’s often a sign they haven’t yet defined what really brings them joy.
So make a list of what you want more of. Slow mornings? Walks in the park? Time with your grandkids?
Then make a new list of what you want less of. Financial stress? Hectic schedules? Clutter?
Then distinguish between your wants from your needs.
One couple realized they were only using 1,000 square feet of their 3,500 square foot home. They knew they could be just as happy somewhere else for a fraction of the cost. Try not to think about retirement as some sort of downsizing. It’s about “right-sizing” your life.
3. Stop Delaying Lifestyle Decisions
Retirement brings a flood of new decisions about housing, travel, relationships, health, and more. It’s normal to feel overwhelmed. But too many people delay the very decisions that would bring them joy.
We often hear, “I know I want to spend more in the early years of retirement while I’m healthy, but I don’t know how.” That’s where planning comes in.
One helpful concept here is the retirement spending smile: higher spending in early retirement while you go live your life, a dip in the middle years, and an uptick later for healthcare expenses.
Of course you don’t have to go straight from the height of your career to full-blown retirement. Many people “tiptoe” into retirement by reducing hours, trying out new part-time work, or simply simulating retirement for a few weeks while still employed.
However you approach it, don’t let fear prevent you from making the decisions that would improve your life now.
4. Stop Avoiding Estate Planning
Estate planning is like the broccoli of retirement: it’s not glamorous, but it works hard for you. Most people avoid it because it feels overwhelming or morbid. But skipping it can have costly, painful consequences for your family.
For example, we’ve seen assets go to the wrong heirs due to outdated beneficiaries, large retirement accounts mistakenly sent to trusts with poor tax treatment, family tension and confusion due to vague or missing documentation.
Estate planning doesn’t have to be hard. It’s about answering a few key questions:
-Who should receive your assets?
-When should they receive them? Now, or spread over time?
-Do you want to avoid probate and maintain privacy?
Start with the basics: review your beneficiaries, get a simple will or trust in place, and keep your records organized. Your future self (and your family) will thank you.
5. Stop Ignoring Healthcare Costs
Healthcare is one of the most misunderstood aspects of retirement planning. Many assume it’ll just “work out.” But even with Medicare, there are premiums, out-of-pocket expenses, and long-term care to consider.
Don’t think of healthcare costs as one giant number. Think in terms of monthly costs, just like your cable bill. Your premiums (which are predictable) typically cover 73–81% of annual healthcare costs.
It’s the unplanned out-of-pocket costs (like dental work, vision, or prescriptions) that catch people off guard. (And Medicare does not cover long-term custodial care. You’ll need a plan for that.)
A Better Retirement Is Built on Fewer Regrets
If you stop doing these five things, you’ll create space in your retirement for what really matters: living a life you actually enjoy.
At Brindle & Bay, we help people just like you plan for a retirement filled with clarity, confidence, and meaning. If you're ready to take the next step, we invite you to book a no-cost consultation with our team today by clicking here.
You bring the questions — we’ll bring the plan.
The client stories shared in this blog post are intended for illustrative purposes only. While inspired by real-life experiences, these examples are composites drawn from a range of client situations and do not represent any one individual. They may be considered indirect testimonials. Actual client experiences will vary. No clients were compensated for sharing their stories.
