Avoid These Common Investing Mistakes Before They Cost You  [Ep. 23]

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When it comes to investing and wealth management, most mistakes aren’t about picking the wrong stock. They’re about lacking clarity, structure, and foresight. In this podcast conversation, we unpacked the most common—and costly—missteps people make with their money and what they can do differently.

Here’s a breakdown of the key themes, along with practical takeaways you can apply today.

Mistake #1: Not Having a Plan

The number one mistake investors make is surprisingly simple: they don’t have a plan.

Without a financial plan, there’s no clear goal, no target, and no way to measure progress. Investors often make decisions based on headlines, influencers, or gut feelings rather than intention. When asked why they made a particular investment, the answer is often, “I read it somewhere,” instead of a reason tied to a long-term objective.

A solid financial plan acts as your North Star. It defines:

• Your goals
• Your timeline
• Your risk tolerance
• How success will be measured

Without that framework, it’s hard to know whether you’re actually making progress—or just spinning your wheels.

If you fail to plan, you plan to fail.

And just as important: a good plan should be flexible, able to adjust as life, income, and markets change.

Mistake #2: Avoiding Estate Planning

Estate planning is often pushed aside because it forces people to confront uncomfortable topics. But avoiding it can create serious financial and emotional stress for loved ones later.

Without a proper will or trust:

• Courts may decide how assets are distributed
• Family conflicts can be more likely
• Costs can increase due to probate
• Financial details can become public

We’ve seen firsthand how prepared families are able to grieve properly—while unprepared families are left navigating confusion, anxiety, and even vulnerability to scams.

Estate planning isn’t just about money. It’s about clarity, privacy, and peace of mind.

Mistake #3: Ignoring Tax Planning Opportunities

Tax planning is one of the biggest areas of missed opportunity. Many investors unknowingly give up thousands of dollars simply by not understanding the rules.

Common examples include:

• Selling investments just days before qualifying for long-term capital gains
• Triggering wash sales and losing tax deductions
• Overlooking tax-loss harvesting
• Failing to evaluate Roth conversion strategies

With the right analysis and technology, investors can see the long-term impact of tax decisions—often revealing substantial savings and even estate planning benefits. Tax strategy shouldn’t be a one-time decision; it should evolve as income and circumstances change.

Mistake #4: Overconfidence and “Winner’s Bias”

Past success can be dangerous.

Whether it’s selling a successful business or owning a stock that performed exceptionally well, many investors assume success is repeatable. This mindset, often called winner’s bias, can lead to excessive risk-taking.

Sometimes gains are driven by skill. Other times, they’re driven by luck. The problem arises when investors can’t tell the difference.

Smart investing requires honesty:

• Was the success repeatable?
• Was it based on research or speculation?
• Does the risk align with your broader plan?

Mistake #5: Overconcentration

Concentration can create massive gains, but it can also destroy wealth just as quickly.

Putting a large portion of assets into one stock or one idea can increase volatility and downside risk. While this may be acceptable for younger investors with long time horizons and high risk tolerance, it’s rarely appropriate for long-term wealth preservation.

Diversification may not create overnight millionaires, but it dramatically reduces the odds of catastrophic loss.

Mistake #6: Letting Emotions Drive Decisions

Research consistently shows that investor behavior, not investment selection, is one of the biggest drags on returns.

A long-term study by Dalbar, Quantitative Analysis of Investor Behavior (QAIB), found:

• The market averaged roughly 10% annual returns
• The average investor earned closer to 4–5%

The gap came from emotional decisions:

• Trying to time the market
• Selling after downturns
• Sitting in cash during rallies

Successful investing isn’t about avoiding volatility—it’s about staying disciplined through it.

The Final (and Most Important) Lesson: Learn From Others

One of the most powerful ways to improve as an investor is simple: learn before you make the mistake.

Read. Research. Ask questions. Learn from people who’ve already lived through market cycles, mistakes, and recoveries.

As the saying goes:

• Fools never learn
• Average people learn from their mistakes
• Wise people learn from others

You work too hard for your money to leave its future to chance.

Final Thoughts

If you take nothing else away, remember this:

• Get an estate plan in place
• Be honest about past successes
• Avoid emotional decision-making
• And above all—have a plan

A clear, flexible strategy doesn’t just have the potential to improve returns. It creates confidence, clarity, and control over your financial future.

Ready to Take the Next Step?

If you recognize any of these mistakes in your own financial life, the good news is this: they’re fixable—with the right plan.

Whether you’re just getting started or want a second opinion on your current strategy, working with an experienced financial advisor can help you bring clarity, discipline, and confidence to your decisions.

A thoughtful financial plan can help you:

• Define clear, measurable goals
• Align your investments with your risk tolerance
• Reduce unnecessary taxes
• Protect your legacy through proper estate planning
• Stay disciplined during market volatility

If you’re ready to stop guessing and start planning, consider scheduling a conversation with a trusted advisor to see how a personalized strategy could help you move forward with purpose.

Your future deserves a plan.

GDS Wealth Management (“GDS”) is an investment adviser registered with the Securities and Exchange Commission (“SEC”). Registration does not imply a certain level of skill or training. This podcast episode and recap are for general informational and educational purposes only and do not constitute personalized investment advice. The views expressed by the hosts are their own and may change over time. Any examples or illustrations discussed are hypothetical and for explanatory purposes only, and they do not reflect actual investment results. Investing involves risk, including the possible loss of principal. Past performance does not guarantee future results. No investment strategy— “boring” or otherwise—can ensure a profit or prevent a loss. Discussions of private or alternative investments are not recommendations and may not be appropriate for all investors. Listeners should consult a qualified financial professional before making any financial decisions. For additional information about our services, fees, and disclosures, please visit www.gdswealth.com.