When Do DIY Investors Need Help?

When Do DIY Investors Need Help?

Table of Contents

Key Takeaway:

DIY investors need help when complexity grows—such as feeling overwhelmed by choices, struggling to align investments with long-term goals, facing tricky tax rules, letting emotions drive decisions, or navigating major life events like inheritance, divorce, or retirement.

Do-it-yourself investing became popular many years before the Meme stock craze.  With apps, zero-commission brokers, and endless online resources, the barrier to entry has all but disappeared. Anyone with a smartphone can buy stocks, crypto, and maybe even alternative investments (alts) in seconds.

The appeal is obvious: lower fees, full control, and the sense of empowerment that comes with managing your own money. Many DIY investors see it as a way to avoid Wall Street sales pitches and keep more of their returns.

This might sound somewhat unusual coming from Porter Investments, a Strategic investment management and portfolio risk management firm, but we’ll be the first to say that many people can be successful investors on their own. With discipline, patience, and a simple plan, investors can build some wealth without ever hiring professional help. In fact, most people have already heard the commonly advised strategies to help do that: save consistently, diversify broadly, and stay invested through market ups and downs.

But success doesn’t mean it’s always easy. The stock market is a humbling teacher. Complexity can grow as savings accumulate, tax rules shift, and emotions and financial goals evolve. Even investors who start out confident can find themselves second-guessing portfolio decisions, wondering if they’re taking too much risk, or overlooking opportunities.

That’s where the harder question emerges: When do DIY investors need help? At what point does independence cross into overwhelm? And how can investors know when bringing in a financial planner or advisor is not a sign of failure, but simply a smarter way to protect wealth and align with long-term goals? The right answers will vary among individuals.

This guide will try and unpack those questions, so that you can get closer to deciding what is best for you. We’ll explore the benefits and pitfalls of DIY investing, the mistakes to avoid, and the complex situations where professional guidance adds value. In the end, you want to strike the right balance between independence and expert advice.

Do-it-Yourself DIY Investing: The Appeal and the Risks

At its core, a DIY investor is someone who chooses to handle portfolio management, research, trades, and financial planning on their own. That means building an investment strategy, making portfolio decisions, and dealing with the ups and downs of the stock market without outside help.

For many, the appeal of DIY investing is irresistible:

  • Accessibility: Online platforms and apps like Fidelity, Schwab, and Robinhood make it easy to open investment accounts and trade in minutes.
  • Cost savings: By avoiding financial advisors, many DIY investors hope to save on fees.
  • Control: Investors make their own decisions about stocks, bonds, mutual funds, and other asset classes.
  • Independence: There’s no worry about any hidden agendas that a financial representative may have with their employer.


And for beginners, the DIY approach can work, especially when investing is simple. Buy a broad market index fund, set up automatic savings, and let compounding do the heavy lifting. Warren Buffett himself has said that most people would be better off buying low-cost index funds than trying to pick individual stocks.

But what feels straightforward in the beginning can grow complicated fast. As wealth grows, complexity multiplies. Tax issues arise, portfolios need rebalancing, and the stock market doesn’t always cooperate with your risk tolerance or operate on your time frame. Suddenly, the simplicity of “I’ll do it myself” may begin to feel more like “I’m in over my head.”

The Potential Benefits of DIY Investing

DIY investing has real advantages, especially for those who are detailed, disciplined, self-aware, and have their biases in check. One of the biggest benefits is cost savings. By avoiding advisor fees and managing their own investment accounts, investors keep more of their returns. In a world where every percentage point compounds over decades, lower expenses can make a meaningful difference in long-term wealth.

Another benefit is control. DIY investors make every decision, from asset selection to when and how to exit positions. You don’t have to rely on someone else’s timeline. That level of control can feel empowering and keep investors close to their money.

For people who are honest with themselves about their limitations and biases, DIY investing also builds financial literacy. Researching potential investments, learning about things such as correlations, proportional performance, martin ratios and standard deviations, as well as confronting your emotions during volatile markets all create valuable lessons.

In short, if an investor is detail-oriented, willing to learn, and disciplined enough to acknowledge their blind spots, the DIY approach can absolutely work. Many have built strong portfolios and met their financial goals without ever hiring a financial advisor.

When Do DIY Investors Need Help?

Here are the clearest signals that it may be time for DIY investors to seek professional guidance:

  1. Feeling Overwhelmed by investment choices
    The marketplace is flooded with investing options: mutual funds, ETFs, stocks and bonds, real estate, even alternative assets. Many DIY investors freeze under the weight of too many choices, unsure which strategy matches their goals and risk tolerance. Paralysis by analysis.
  2. Difficulty aligning investments with long-term goals
    Owning a portfolio is one thing; aligning it with financial goals like retirement, education, or building a nest egg is another. Without a clear investment plan, many investors chase performance rather than building a durable strategy. Sometimes we think we are tracking ourselves to a plan when we are not.
  3. Struggle with tax implications and their continual change
    Capital gains, Roth IRA conversions, retirement withdrawals, and tax-loss harvesting all require more than a surface-level understanding of finance. Small mistakes here can cost thousands of dollars. The recent “One Big Beautiful Bill, or (OBBB)” introduced new tax related considerations for your investments.  
  4. Emotional investing leads to poor timing decisions
    Buying at peaks, selling in market downturns, or letting greed drive portfolio decisions is one of the most common mistakes DIY investors make. Volatile markets test everyone’s nerves, and emotions can undo years of disciplined saving.
  5. Life events that add complexity
    An inheritance, marriage or divorce, selling a business, or nearing retirement are times when financial needs change dramatically. These situations often require expert planning to avoid costly mistakes.
  6. Research/Software costs


Some advanced and comprehensive portfolio management and retirement income planning software licenses are just not available to an individual investor. In addition, many financial advisor firms can use analytical tools and services where monthly subscriptions can run $2000+ per month, making the cost hard to justify unless a portfolio is well into seven figures. 

You should always remember: asking for help doesn’t mean you’ve failed. It means you’re serious about protecting your wealth and future.

DIY Investing Pitfalls and Mistakes to Avoid

While DIY investing can work, many DIY investors fall into predictable traps:

  • Overconfidence bias: Believing you can consistently outperform the stock market without the right tools, research, or discipline. One problem is that very often you can outperform in the short term, thereby reinforcing that overconfidence. 
  • Lack of diversification: Holding too many individual stocks or concentrating on one sector or asset class. Modern portfolio theory teaches that many times diversification across asset classes helps balance returns and risks.
  • Chasing returns: Buying into hyped ETFs or stocks during bull markets, then panic-selling when the market drops.
  • Ignoring taxes: Forgetting about capital gains, Roth IRA rules, or retirement withdrawal strategies.
  • Neglecting the big picture: Many DIY investors focus only on picking investments, not on financial planning, estate needs, or social security claiming considerations.
  • Misjudging risk tolerance: Thinking you can handle a 20% market downturn… until it does happen. Risk tolerances and feelings can change often. Knowing today how you will react to the future is based on how you feel today, not the future. 
  • Overlooking expenses: Even “free” investing carries hidden costs in taxes, spreads, and opportunity cost.


The appeal of DIY is real.  But unfortunately, so are the mistakes. And mistakes in finance compound in the wrong direction.

The Limits of Going It Alone: Complex Situations That Require More Than Google

There are areas of finance and investing where Google searches and AI summaries aren’t enough. Professional help becomes important in situations like:

  • Advanced tax planning: Multiple state taxes, charitable giving strategies, and small business deductions.
  • Retirement distribution planning: Deciding which accounts to withdraw from first to minimize taxes and keep money compounding longer.
  • Equity compensation: Stock options, RSUs, and incentive plans from employers can create big opportunities but possibly big tax headaches.
  • Business succession: Planning how to pass on or sell a business requires coordination across legal, tax, and investment advisors.
  • Estate and legacy planning: Coordinating investments with wills, trusts, and insurance coverage.
  • International investments: Cross-border assets add another layer of tax and legal complexity.


These situations move beyond the comfort zone of even financially literate investors. It’s not about lacking intelligence; it’s about recognizing that finance is as complex as medicine. You wouldn’t perform surgery on yourself. Sometimes, you shouldn’t perform surgery on your portfolio either.

How Professional Guidance Complements DIY Efforts

Here’s where nuance matters: hiring a financial advisor doesn’t mean giving up control. Many investors imagine that once they bring in help, they’ll be told what to do with every dollar. The best advisors will partner with you. They enhance your strategy rather than replace it.

Professional advisors provide:

  • Specialized investment focus: it’s hard to be an expert on more than 1 or 2 specialized investment approaches. 
  • Comprehensive financial planning: tying together investments, savings, retirement, and estate goals.
  • Tax-efficient portfolio design: helping investors keep more of their returns by minimizing tax drag.
  • Accountability and coaching: reminding investors to stay disciplined during volatile markets instead of chasing returns.
  • Integration of insurance and estate planning: ensuring your wealth protects not only you, but your family.


Some DIY investors use some type of hybrid approach. One approach could be
managing their own investment portfolios for day-to-day decisions, while relying on a financial planner for complex areas like retirement income planning or tax strategy. Another option could be managing the strictly “buy and hold” portion of your portfolio on your own. You then use a financial advisor or money manager for that portion of your portfolio where you want to implement a more labor-intensive approach.

The key advantage here is perspective. Advisors bring objectivity to financial decisions that are often clouded by fear or greed. Sometimes just having a second set of eyes can prevent costly mistakes.

DIY Investing FAQs

What’s the difference between a DIY investor and a robo-advisor?

DIY investors make all the decisions themselves. A robo-advisor automates portfolio management based on your goals and risk tolerance but lacks the personal touch of a human advisor.

Can a DIY investor succeed without ever hiring help?

Yes, particularly if they stick to simple, diversified strategies like low-cost index funds. But as wealth grows, so do the stakes and the complexity.

What tools or platforms are best for DIY investing?

Brokers like Fidelity, Schwab, and Vanguard offer strong platforms. Many investors also use third party apps that provide research, portfolio management tips, and financial planning tools.

When is it best to hand things off to a professional?

Major life events, tax complexity, and retirement planning are key moments. Also, when emotions are consistently leading to poor investment decisions.

Do DIY investors really save money in the long run compared to hiring help?

Sometimes yes, but not always. Fees do matter, but mistakes from emotional trading can cost far more than a reasonable advisor fee.

Striking the Right Balance Between Independence and Guidance

DIY investing has real advantages. It builds financial literacy, gives investors direct control, and avoids unnecessary expenses. But independence has limits.

The smartest investors aren’t the ones who do everything alone. They’re the ones who know when to defer on a particular expertise. 

So, ask yourself:

  • Are my investments aligned with my long-term financial goals?
  • Do I truly understand my risk tolerance in volatile markets?
  • Am I confident about taxes, estate planning, and retirement income?
  • Do I feel more in control or more overwhelmed?


Success in finance isn’t about ego. It’s about process. For many DIY investors, the best outcome comes from a blend of independence and guidance. It’s about taking ownership of money decisions while knowing when professional support can reduce risk, improve results, and deliver peace of mind.

Conclusion

The real question isn’t whether DIY investing is good or bad. The real question is: when do DIY investors need help?

The answer depends on your financial goals, complexity, and comfort level. Some investors will thrive with a DIY approach, especially early on. But as portfolios grow and life events multiply, the balance shifts. What once felt like a simple hobby can turn into a full-time job with real financial consequences. The trick is knowing when to call help. 

Remember, investing is personal, and every investing strategy has tradeoffs and opportunity costs.  We must always be brutally honest with what we want, and if we are willing to do what it takes to achieve the desired outcome. What worked for your neighbor or coworker does not mean it is right for you. Before making any changes, preparation and approaching it with realistic expectations is the key. Spend a few minutes with us to see if we are a good fit for each other and to learn more about our passive investment strategies and active investment strategies.

Investment Manager | Houston | Bob Porter
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The Porter Investments Strategies were developed by our President and founder, Bob Porter. His prior work at Fidelity Investments allowed him the opportunity to advise and study a diverse group of investors.

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