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Investment questions to help you become a better investor

Investment questions
Categories Investing

Almost all successful investors have a very strong analytical mind. One of the best ways to stimulate and direct your analytical mind is to ask the right questions. When you ask yourself the right questions, you can think optimally and make better decisions.

The same goes for making good investment decisions. Asking yourself the right questions can lead to better analysis, which in turn can lead to either smarter investment decisions or an improvement in your attitude toward investing in general.

To help you become a better investor, we have looked at what we believe are the six most important investment questions. At the end of the article, we have also included a list of 30 investment questions that you can use as a checklist before making any investment decision.

Table of contents

1. How differently would I have to think and act so as not to miss an investment opportunity?

It has happened to each and every investor. A great opportunity that was completely missed. The most popular general example of the last decade might be Bitcoin, the Monster baverage or SPY during the initial COVID-19 panic, where there was a big drop and then a twofold increase.

We would all buy a few dozen Bitcoins or the Monster stocks if we could turn back time, but of course it’s easy to be a general after the battle.

best performing stocks
Source: Charlie Bilello, 2022

However, instead of feeling sorry for yourself, there’s a much better way to think and learn from missed opportunities. Once such way is to ask yourself how differently you should have thought and acted at the time to avoid making an investment mistake.

Ask yourself sub-questions like:

  • What did you not understand at the time?
  • Did you take enough time to study the opportunity?
  • Why were you closed-minded about the investment opportunity?
  • What would have led to making a better decision?
  • How would your day have looked if you had invested? (wiring the money, clicking the “buy” button…)?

Try to imagine as vividly as possible all that would have had to happen for you to take the opportunity.

  • Would you have needed to take a day or two to study the opportunity in more detail?
  • Would the right community of people have encouraged you to make the right move?
  • Were you too overwhelmed or too narrow-minded, maybe because you were struggling in some other area?
  • Or perhaps you did not have enough money left over to invest?

Answering these questions should also provide you an answer to another key question: how can you change your attitude, environment, or circumstances to prevent the same mistake from happening to you again?

Perhaps you can establish a rule to invest at least one day in studying similar investments. Perhaps you could create a small fund that you can risk on similar investments; or maybe you could join a new community, change your decision-making process, or something similar.

2. Which risks are the most likely to produce the biggest returns?

Let us now move from missed opportunities to the proper attitude toward future opportunities. There are almost unlimited possibilities as to where you can invest your money.

The basic question that can help you narrow down the choices is: which risks are most likely to yield the greatest returns? When you decide to invest your money, you also take the risk of losing some of that money (in some cases, you may even lose all of it).

Different types of investments come with different risks.

The goal in investing is to find the investments that have as low risk as possible and a high potential for profit. The best investors seek investments with a high enough margin, so the risks are very small compared to the upside potential.

If you already take risks, you want to make sure those risks pay off, but it’s impossible to make only profitable investment decisions. Studies show that even the best investors in the world are wrong about half the time, but when they are right, they are exceptionally right.

The point is, if you want to answer the question of which risks are the most likely to produce the biggest returns as correctly as possible, you need to:

  • Have a solid and proven investment strategy that helps you frame each opportunity
  • Understand the asset class and specific investment in detail (and how it compares to other asset classes)
  • Know, understand, or recognize something that the majority of investors don’t (having a framework and process for picking specific investments)
  • See the big upside potential that can happen, and in what timeframe

As an investor, you must be able to categorize and compare different investment opportunities. You must develop your mind to think in terms of risks, rewards and odds.

All this will also greatly help you to develop your analytical mind, become better in business, train your decisiveness, and, in the end, you will get an opportunity to choose a winner and outperform the market.

3. What’s my edge in this investment?

Keeping winning investments in mind leads us to the next question, and maybe the most important one when it comes to being a successful investor – what is your edge in this play?

If you don’t have a competitive advantage, don’t compete. Investing is not easy and it’s super competitive. That’s why you always need an edge. There are many different edges you can have in investing:

  • Informational edge – having unique or new information
  • Analytical advantage – having an ability to better analyze stocks or read charts
  • Emotional / Behavioral edge – being able to act differently from the masses
  • Being an early adopter – there’s constant innovation in the finance world
  • Industry expertise – a superior understanding of a certain industry
  • Tech / IT skills – leveraging programming skills to better analyze opportunities
  • Geographical – having local experience and understanding
  • Social – having friends or family that have one of the edges above and will let you join in
  • Long-term orientation – this can be an important edge when indexing and investing in individual companies

As you can see from the list above, most often you need to have some unique type of know-l-EDGE and insights. If you don’t know right away what your edge is, you probably don’t have one. But don’t let that stop you.

It’s never too late to start developing your investing edge, and Equito academy is here to help you.

4. What could go wrong and how hard would I be hit?

One of the worst personal characteristics in investing is to be naïve. As the book The Psychology of Money explains, the worst money decisions are made based on excessive optimism and emotions like greed, insecurity, and fear. That’s why the author Morgan Housel recommends that you be a sensible optimist in life.

Sensible optimists don’t believe everything will always be great, because it won’t. They believe that the odds of good outcomes are in their favor over time, while being sure to have the financial margin and competencies to face the setbacks that occur along the way.

Being a sensible optimist also means you should be okay with a lot of things going wrong, because that’s the natural course of life.

That leads us to two important investment questions to ask yourself before making an investment decision:

  • What could go wrong with this investment?
  • How hard would I be hit in the worst-case scenario?

And remember, as Carl Richard said, risk is what’s left when you think you’ve thought of everything. Ask yourself what would happen if your investment declined by 30 %, 50 %, 80 % or 100 %?

  • Could you financially survive?
  • Could you keep paying the bills and have positive cashflow?
  • How would you hold up mentally?
  • How would that influence your spouse or your family?
  • What if you also lost your job?

A very important part of successful investing is having outstanding risk management in place, making sure you don’t overstretch yourself on a single investment, and ensuring that you don’t get consumed by emotions such as greed or naïve optimism. There’s no point in investing if you can’t sleep at night.

5. What could go right?

You want to be a smart, sharp investor, but not pessimistic. You must never forget about the other part of the risk equation, and that’s what can go right – the upside potential.

At every moment there are numerous investments out there that are bringing great returns to investors. Just as things can go wrong, they can absolutely go right. Your job as an investor is to find a few investments that will go extremely right.

This section is especially useful for investors that are pessimistic by nature. If you are one of those, you should ask yourself several sub-questions in this regard, such as:

  • What is the upside potential of the investment and is it in line with the risks?
  • How much do you expect to earn on the investment? How realistic is it?
  • How many months, years, or even decades would it take for the investment to go right?
  • What sequence of events must happen for things to go right, and where can you help?
  • How will you make sure you are not exiting the investment too soon?
  • What will you do with all the additional money?

6. What kind of emotions are driving my investment decision?

The final investment question on our list addresses self-awareness and introspection abilities when it comes to investing. A very important part of successful investing is being able to understand and manage your emotions.

As an investor, you must often act differently from what you are feeling. The best way to dealing with your emotions is to map them, in other words, write them down. The recommended way is to use a pen and paper (instead of a computer).

The main idea is to explore your emotions every time you are on the brink of making an investment decision. The following questions should help you explore your emotions:

  • What am I feeling at the moment? Use the wheel of feelings.
  • What kind of mood am I in?
  • How strong are my emotions from 1 to 10? Am I over- optimistic or pessimistic?
  • Am I in a rush, greedy, or over competitive?
  • What thoughts are triggering my emotions?
  • What would [enter your favorite investor] do?
  • How are my emotions aligned with a logical analysis of the opportunity?
  • If I invest, do I act in accordance with or against my emotions?

If you sense that you’re making an emotional decision instead of a logical one, explore further. Try to find the root cause of the emotions that are trying to drive your investment decisions. Many times, our investment decisions can be driven by causes such as:

  • Rushes of greed because of troubles in personal relationships
  • Fear of missing out and being left alone
  • Lack of discipline or feeling overwhelmed, and thus taking shortcuts
  • Suffering from low confidence and assuming we just deserve a win

This might sound cheesy or far-fetched, but managing emotions is one of the most important parts of successful investing. That’s what emotional management really means, to map and account for your emotions.  

The ultimate list of investment questions

To conclude this blog post, we have listed the most important of the above-mentioned investment questions and added more standard investment questions that can help you make better choices.

You can use all of these questions as a checklist before making an investment decision.

Here is the list of all the important investment questions:

  • How does the investment opportunity work? Do you understand it in detail?
  • Did you take enough time to study the opportunity or are you rushing?
  • Can you gather additional information about the investment, or have you maxed out everything?
  • Who are people behind the investment and are they reliable?
  • Is the investment regulated or not? What does that mean in terms of risks?
  • Is your investment protected if the provider/adviser goes out of the business?
  • What is your edge when it comes to this investment?
  • Is now the right time to make an investment – in general in your life and considering the timing of this specific investment?
  • Does the investment fit your investment strategy?
  • Are you breaking any of your investing rules?
  • How does the investment fit into your overall portfolio and investing goals?
  • Are the risks in accordance with the potential reward?
  • What could go wrong and how hard can you afford to get hit?
  • How hard would you be hit in the worst-case scenario? Would you financially survive?
  • How would you hold up mentally in the case of a hit?
  • How would a hit influence your spouse or your family?
  • Do you have a risk management policy in place (exposure, stop loss etc.)? Write it down.
  • What could go right? What is the upside potential of the investment?
  • How much do you expect to earn on the investment? How realistic is it?
  • How will you make money – dividends, interests, capital gains etc.?
  • Do you have any better investments on the table?
  • For how long do you plan to invest? How many months, years or even decades would it take for the investment to go right?
  • How liquid is the investment? What’s the probability that you will need to liquidate the investment before that? What does that mean for returns?
  • What sequence of events must happen for things to go right and where can you help?
  • How will you make sure you are not exiting the investment too soon?
  • What thoughts are you associating with the investment?
  • What kind of emotions are driving your investment decision?
  • Are you in a rush, being greedy or over competitive, or driven by FOMO?
  • What would [enter your favorite investor] do?
  • What are the related costs with the investment? Do you know the total fees? Can you optimize the costs?

Well, we hope all these investing questions will help you stimulate your analytical mind, become a better investor, and better in business in general.

Just make sure all these questions won’t lead you to analysis-paralysis. In the end, you must gather the courage to invest your money, just be sure to do so cleverly.