Even the most financially successful individuals can make costly mistakes when planning for retirement. Having a high income or a sizable investment portfolio doesn’t automatically mean you’ll glide into retirement without financial stress. In fact, wealth often adds complexity—tax implications, investment strategies, estate planning, and withdrawal timing all become more intricate at higher income levels.

Studies show that working with a financial advisor can make a dramatic difference. According to Vanguard, expert guidance can increase net returns by 3% per year, which may not seem like much at first glance. But over 20 years, that can add up to more than a 60% difference in overall wealth—a massive impact for those who want to maintain their lifestyle, fund generational wealth, or give back through philanthropy. That’s why it could be huge to work with a financial advisor.

Unfortunately, many affluent retirees still fall into common traps that can cost them hundreds of thousands—or even millions—of dollars, even though there are free services to match with advisors with ease. Here are five silly but avoidable mistakes that could put your retirement at risk.

1. Assuming High Net Worth Means You Can’t Run Out of Money

It’s easy to assume that having a a lot of money in the bank means you’re set for life. But even a large fortune can evaporate if not managed correctly. Retirement today lasts much longer than it did for previous generations, and with people living well into their 80s and 90s, a poorly structured financial plan can result in outliving your wealth.

Spending patterns also shift in retirement. Many high-net-worth individuals ramp up discretionary spending early on—luxury travel, second homes, hobbies, and family gifting—only to realize too late that their portfolio isn’t growing fast enough to sustain it. Without a long-term investment strategy that accounts for market fluctuations, inflation, and tax efficiency, even a robust nest egg can dwindle faster than expected.

Partnering with a financial advisor can help ensure that your portfolio is structured to sustain your desired lifestyle indefinitely, accounting for both planned and unexpected expenses. This isn’t just about saving—it’s about making sure your wealth works for you in the most strategic way possible.

Use this free service to match with up to 3 top financial advisors now.

2. Underestimating the Tax Burden on Retirement Income

One of the biggest mistakes high earners make is assuming their tax burden will decrease in retirement. In reality, without careful planning, taxes can eat away at your wealth more aggressively than during your working years. Required Minimum Distributions (RMDs) from tax-deferred accounts like 401(k)s and IRAs can suddenly push you into a high tax bracket. Capital gains from investments, rental income, and estate taxes can further complicate your financial picture.

Strategic tax planning is essential. For instance, many retirees overlook Roth conversions, which can significantly reduce tax liability in later years if done correctly. Additionally, charitable giving strategies—such as donor-advised funds or Qualified Charitable Distributions (QCDs)—can lower taxable income while maximizing philanthropic impact.

Wealthy retirees who work with financial advisors don’t just minimize their tax burdens—they often save millions over their lifetime by structuring withdrawals and estate plans efficiently. Getting expert guidance on tax-efficient income streams can prevent Uncle Sam from taking more of your retirement money than necessary.

3. Ignoring Inflation and Failing to Adjust Investments Accordingly

Many affluent individuals assume that their wealth automatically protects them from inflation, but failing to account for it can be a major financial misstep. Even at a modest 3% annual inflation rate, purchasing power can decline significantly over a long retirement. A lifestyle that costs $500,000 per year today could require $900,000 annually in 20 years just to maintain the same standard of living.

Yet, many retirees shift too much of their portfolio into ultra-conservative investments like bonds and cash, mistakenly thinking that a “low-risk” strategy is the safest approach. While reducing volatility is important, neglecting growth-oriented assets can be just as dangerous as taking on too much risk. The key is striking the right balance—ensuring your portfolio continues to grow while maintaining the flexibility to weather market downturns.

Working with an advisor ensures your investment strategy evolves alongside economic conditions, keeping your portfolio structured for long-term growth without exposing you to unnecessary risks. It’s not just about preserving wealth—it’s about ensuring it continues to grow at a pace that outpaces inflation.

4. Failing to Structure Wealth for Multi-Generational Impact

For many affluent retirees, retirement planning isn’t just about personal financial security—it’s about creating a legacy. Yet, a surprising number of high-net-worth individuals fail to implement a proper estate plan, leaving their heirs vulnerable to excessive estate taxes, probate complications, and financial mismanagement.

Wealth transfer is more complex than just writing a will. Without a thoughtful estate strategy, as much as 40% of your assets could be lost to estate taxes. Trusts, tax-efficient gifting strategies, and family governance structures are all crucial tools that can ensure your wealth transitions smoothly to the next generation.

Additionally, educating heirs on wealth management is essential. Sudden inheritance without financial literacy can lead to mismanaged investments, overspending, or unnecessary legal disputes. Many financially savvy families engage advisors not just for wealth management, but also for generational financial education. An advisor with expertise in estate planning can ensure that your wealth is protected and passed down efficiently, aligning with your long-term vision.

5. Hiring the Wrong Financial Advisor

Even the most sophisticated investors can make the mistake of choosing the wrong financial advisor. Many assume that all financial advisors are the same, but the reality is that some prioritize selling high-commission products over acting in their clients’ best interests. Choosing the wrong advisor could mean paying excessive fees, getting suboptimal investment advice, or even falling victim to conflicts of interest.

A crucial distinction is whether an advisor is a fiduciary—a legal obligation requiring them to act in your best interest at all times. Shockingly, not all financial advisors are held to this standard. Many operate under a suitability standard, meaning they can recommend investments that are merely “suitable,” even if better options exist.

That’s why  a company like WiserAdvisor rigorously vets financial advisors to ensure they are fiduciary professionals who put your needs first. By working with a vetted advisor, you can be confident that their advice is aligned with your financial goals—not their commission incentives. Finding the right financial advisor can make a significant difference in the long-term success of your retirement strategy.

Find out if you are ready to retire

Figuring out the right time to retire doesn’t have to be hard. The free questionnaire from WiserAdvisor matches you with three fiduciary financial advisers in about 2 minutes. Each adviser has been vetted by WiserAdvisor and is legally bound to act in your best interests. If you’ve got $50,000 or more in cash, stocks, bonds, other assets, or a combination of these and are ready to be matched with advisers that would like to help you achieve your financial goals, answer the questionnaire now.