10 Powerful Investing Lessons from the World of Trading
Legacy Food Storage

10 Powerful Investing Lessons from the World of Trading

83% discount on VPN
Share on facebook
Share on google
Share on twitter
Share on linkedin
Share on pinterest
Share on reddit
Share on whatsapp

Surprisingly, while trading is very different from investing in many aspects, the two share some important similarities as well. In this article, we are going to explore 10 powerful investing lessons that we can apply from the world of trading!

While I am primarily focused on long-term investing, I do enjoy trading—despite the horrifying statistics and studies that posit less than 5% of traders are actually profitable over time (and some place the number at closer to 1%).

Over the years, I’ve discovered that my trading (options and swing trading) has actually provided me with a number of practical lessons that I have been able to integrate into my passive-income investing approach—insights that have added material value to my investing.

To be clear, trading is a brutal business and I do not recommend most folks dip their toes in those waters. For most, it is a wealth destroyer rather than generator!

My hope is that, by sharing some of the best investing lessons I’ve gleaned from trading, I can add some additional value to your investing activities—without you having to pay the high price of admission to the trading world!

So, grab yourself a cup of coffee (or Jack and Coke if you prefer) and take a few minutes to peruse these 10 insights—you may be surprised to find some valuable insights that you can take away and apply to your investing today!

Table of Contents

Lesson #1: Document Your Investing Activities

The first investing lesson we can learn from trading is that we should document our investing activities.

In trading, we learn to thoroughly document everything through effective journaling—setups, trade designs (position, size, stops, targets, risk-reward-ratios, etc.), signals, our reasoning for taking the trade, and even our mood at the time. The reason is simple—you can’t repeat what you don’t define.

Accurately and thoroughly documenting our trades allows us the opportunity to (1) identify both positive and negative trends (i.e., what appears to be working and what is not) and (2) leverage that knowledge to improve our trading effectiveness and efficiency.

This analysis involves outward/quantitative factors, as well as internal/qualitative ones. After all, trading success is materially influenced and impacted by both our process and our psyche.

Investing is no different!

We should be able to analyze our moves (actions) over periods of time in order to identify strengths and weaknesses in both our investing plan/process and our mindset.

In the world of trading, feedback is immediate—we know very quickly whether something worked or was a bust. Thus, we can build a rather large depository of trading data in a relatively short period of time—enabling us to refine our strategies on both a macro and micro level.

This is a significant difference between trading and investing. In the investing world, it can take 3-5 years (or even longer) to recognize how well a particular action performed. However, this does not mean that we can’t extract value from journaling when it comes to our investing!

To the contrary, it provides us with tremendous value at the macro level—meaning it helps us answer the pivotal question: Are we adhering to our overarching investing plan—both in terms of process and mindset?

This is critical for long-term investing success—whatever strategy or strategies you personally employ.

Specifically because of the length of the feedback loop, it is important for us to stay the course and avoid deviating to quickly from it.

Journaling (or documenting or investing moves) serves a critical role in keeping us on track.

Due to all the short-run noise, it is easy to suffer from something akin to “spatial disorientation” in the world of aviation, such as what JFK Jr experienced and led to his tragic crash. Little by little, we lose our orientation and unknowingly stray from our intended “flight” path (aka investing plan).

This noise is the equivalent of haze or fog that can negatively impact and cloud our vision and judgement. As such, investing requires us to operate much like a pilot flying in IFR (instrument flight rules) conditions.

Our journaling serves as our “instruments” to keep us safely on course and maintain our long-term orientation. Without it, we are all susceptible to allowing our emotion (or feelings) to begin influencing our short-term decision-making process.

Spatial disorientation (typically caused by untrained and/or inexperienced pilots flying into IMC conditions) is a leading killer of pilots—and, in a similar way, failing to document our investment actions can lead to investing disorientationa leading cause of long-term investing failure for many inexperienced retail investors!

The outcome for investors is no different than a pilot unknowingly entering a graveyard spiral. The only way to escape an inevitable “crash” is to ignore our emotions and trust our instruments—in our case, monitoring our actions, progress, and decision-making process via our journaling!

Over time, proper documentation can not only help us to stick to our investing plan (i.e., portfolio management, investing process, and mindset) but enables us to identify when and what adjustments are warranted.

As such, documenting our investing is a critical lesson we can borrow from the world of trading!

Legacy Food Storage

Lesson #2: Investing Success Requires a Consistent, Systematic Approach

The second investing lesson we can glean from trading is that success requires a consistency.

One of the reasons so many folks fail at trading is that they lack a consistent, systematic approach—they are all over the place.

Once again, investing is no different!

While most retail investors feel as though they are being consistent—in reality, they are all over the place as well. Again, this can lead to investing disorientation and, ultimately, to failure.

Unlike trading, investing is fairly simple and straight-forward. It doesn’t require a complex process—but it does demand a systematic approach.

Like traders getting involved in a multitude of technical setups and strategies, it is easy for us to lose focus and chase the noise and/or herd.

As Buffett stresses, it is critical for us to stick to what we know—whether that is an investing style or a particular sector or industry. We can expand the scope of our investing over time; however, it is important to master one thing at a time—providing us with a stable foundation upon which to build.

Furthermore, we need to develop a clearly defined process… and then stick to it!

Long-term investing success is all about two things: (1) process and (2) mindset.

When it comes to the process component, it needs to be simple (efficient), effective, and systematic. I highly encourage you to read our article Harness the Power of Quant Investing in Our FIRE World to learn more about developing a sustainable, systematic, winning process for your investing.

Like trading, a fundamental key to our long-term investing success is being consistent and systematic!

Warren Buffett Investing Quote
83% discount on VPN

Lesson #3: Keep It Simple to Achieve Investing Success

The third takeaway from trading that we can apply to investing is that the best path to success is to follow the KISS principlekeep it simple stupid!

The world of trading is filled with a limitless number of technical indicators, signals and patterns. The key to success lies in being able to minimize your required exposure to them. The more complex your strategy is, (1) the more moving parts you have that can break, (2) the harder it is to analyze your performance (i.e., what adds value and what doesn’t), and (3) the harder it is to by consistent (i.e., replicate your trades).

Unfortunately, there is a limit to that simplicity when it comes to trading. If simple worked in and of itself, then 90% of traders would be successful rather than 10%.

When it comes to fundamentals-based, long-term investing, simple works even better!

Over-complication does NOT add value to long-term investing. Keep things as simple as possible.

Our success lies in finding a healthy balance between passive index investing and PhD-level quant algos!

As long-term investors, we fall under the domain of chaos theory (aka the butterfly effect). Unlike trading, we aren’t interested in the minutia. Over longer periods of time, it is impossible to predict their impact—it’s just noise.

Rather, we want to focus on large fundamental drivers of long-term performance—precisely why simplicity works so well with investing.

Furthermore, we don’t want to be active “traders”—we want to be passive investors! Over complicating things nearly always leads to too much action—or churn. This portfolio churn is the enemy of long-term investing success.

By keeping our process streamlined (efficient), we limit the workloads and time demands we place on ourselves—again, we don’t want to be active traders, glued to our monitors.

Thus, by keeping things simple, we not only improve our investing performance, but we also increase the likelihood that we will consistently stick with that process and stay in the game over the long run!

Lesson #4: With Investing—Like Trading—Context Matters!

The fourth investing lesson we can take from trading is that context matters.

When it comes to trading, we rely on technical analysis. However, while this may appear to be a purely quantitative pursuit, the reality is that it is far more qualitative (subjective) than most are willing admit. Stated differently, it is much more of an art than a science!

As such, context matters—and matters a lot!

Those technical indicators (though quantitative in and of themselves) can mean entirely different things depending on the context the present themselves in.

Again, investing is no different!

While I highly encourage you to employ a comprehensive and systematic investing process that is predicated on an objective, quantitative analysis of financial metrics—context (i.e., the qualitative nature) still matters.

For example, sustainable competitive advantages (aka moats), management, secular dynamics, and long-range outlooks must be thoughtfully considered. They represent the broader canvas (or background) upon which those quantitative metrics are painted—and that context matters for long-term investing.

Context Matters with Investing

This is why we recommend utilizing a qualitative capstone within your investing process.

We can’t rely completely on our quantitative analysis—there is an inherent human (i.e., subjective/qualitative) element that is always required of us when engaged in long-term investing!

We must always be willing to invest the time to do our homework and understand the context of what we are investing in—at every level (e.g., the broad market/economy, sector, industry, and company).

83% discount on VPN

Lesson #5: Investing Success Requires Knowing When to Say No

The fifth thing investors can learn from trading is that success requires knowing when to say no.

One of the biggest contributing factors to failure in trading is not knowing when NOT to trade (aka over trading). Inexperienced traders—filled with enthusiasm and enough knowledge to be dangerous—see opportunity everywhere and lack patience.

This leads most to snatch defeat from the jaws of victory!

Investing is no different!

Let’s be crystal clear… we don’t need to partake in every potential investment opportunity.

As Buffett has so eloquently asserted, there are no called strikes in investing! We don’t have to swing at anything. Instead, one of the keys to long-run success is to patiently wait for the best pitch and then swing for the bleachers.

We need to employ the proper investing mindset—one that seeks to identify opportunities that best fit our own unique wheelhouse or sweet spot. These are opportunities that fit within our clearly defined investing plan and are a solid match for our knowledge, skills and abilities.

Over-investing leads to bad outcomes, contributes to excessive churn, and results in a poor allocation of our available investment capital.

We must have the discipline to stay within our circle of competence. When we become too active and swing at pitches we shouldn’t, we get ourselves into trouble.

Stanley Druckenmiller’s disastrous foray into tech stocks in the 90s is a perfect example of this—one that resulted in a $3-billion loss in just six weeks!

We must maintain a proper mindset—one that is patient, sticks to our plan, and avoids the emotional Siren’s call of FOMO and herding!

One of the greatest parallels between trading and investing is the need to know when to say no and avoid over trading or investing.

Lesson #6: Know When You’re Wrong!

The next lesson we can take from trading and apply to our investing is that we need to know when we are wrong.

In the world of trading, we always define our risk at the time we enter a trade—never afterwards.

This involves both position size and stops. In trading, the margin for error (or risk) is inherently small. We determine a point at which the reason we got in the trade is no longer valid and the goal is to enter a trade as close to that point as possible. If we’re wrong, we want to be wrong fast and small!

Legacy Food Storage

The same applies to investing, albeit in a slightly different context.

With long-term investing (especially with a value component), we want to allow our investments plenty of time for our underlying investing thesis to play out. Because we are looking at much longer time horizons than with trading, we need to allow our investments to have more room to breathe.

We don’t want to be trigger happy and constantly exit our positions based on short-term noise.

However, this does not mean that we don’t want to minimize our losses—losses matter. Hence Buffett’s top two rules for investing are never lose money and never forget rule number one!

We don’t want a bad investment to just compound into a worse investment!

We need to enter our investments with a solid margin of safety and a knowledge of why we are in the investment (aka our investment thesis).

Without a clearly defined reason for being in an investment, we have no way of knowing when it is no long valid and we need to get out.

Furthermore, beyond the thesis itself, we must employ a mindset that is (1) capable of identifying when that thesis is no longer valid and (2) willing to accept that reality and exit the position.

Warren Buffett Never Lose Quote on the Importance of Defense

Finally, our investing plan should include a clear set of rules for exiting positions. For example, this may include a dividend cut, change in the underlying fundamental story, or a specific change in a financial metric.

This is another reason why documenting our investments (see lesson #1) is so critical. It helps us to determine whether we are following our rules—or holding onto positions when we shouldn’t be.

As with trading, it is critical in investing that we are able to minimize our losses in order to maximize our long-term success. This requires (1) being able to identify when we are wrong and (2) being willing to accept that reality and exit the position devoid of emotion—thereby taking a small (rather than large) loss.

Lesson #7: Always Conduct After-Action Investing Reports

Another powerful trading lesson that can be applied to our investing is the need to perform after-action investing reports.

In trading, I always analyze a trade after exiting it. I compare the actual performance to my original expectations and setup. The goal is to identify what worked, what didn’t work, and why. I can then take that knowledge and apply it to future trades.

Investing is no different!

After we exit an investment position—whether it was successful or not, we should conduct a brief but thorough after-action analysis.

Primarily, we should seek to identify whether the outcome was consistent with our initial expectations. If there was a variance (positive or negative), we want to identify why.

This is why documenting our investments (see lesson #1) is so critical. We can’t analyze the outcome and gain any valuable insights if we don’t have a record of how and why we initiated the investment!

Specifically, we need to identify if the variance was the result of (1) a problem with us (mindset), (2) a problem with our process, or (3) simply an unavoidable outcome based on probabilities.

For example, we need to determine if the outcome was the result of a mindset problem. Did we experience too much volatility and bailed? If so, we may want to (1) reduce our exposure to volatility in the future or (2) work on our ability to trust the process and persevere (i.e., ignore/withstand short-run volatility) in the future.

This is where it is also helpful to revisit the report after six months to a year and compare it to how the stock is performing after a sufficient period of additional time. Doing so will help us to identify if we were simply dealing with short-run volatility—meaning we should have stuck with our investment.

Did we succumb to FOMO or herding? We need to identify if our reasons for entering or exiting the position were emotionally based rather than process driven.

We also need to determine if we deviated from our plan, strategy or process. If so, why? If this was a negative, we want to try to avoid that behavior in the future. If it was a positive, we may want to consider adjusting our plan, strategy or process.

Is there a flaw in our process that contributed to the outcome? For example, is there a variable that we believe is a success driver (and is built into our process) but may not be? Was there a variable in play that we didn’t recognize? If so, we may want to consider that in future investments.

83% discount on VPN

For example, maybe the company’s fundamental story deteriorated due to its inability to manage its debt. Are we including debt (leverage) in our quant process? If not, we may want to consider doing so.

Finally, what role did luck play? Sometimes, probabilities just play out and outcomes occur that we couldn’t have anticipated—both good and bad. The problem is that we can’t repeat luck!

Improving our process requires the ability and willingness to identify when our results were the product of luck (random probability) and not our plan or process.

For example, we may have deviated from our process (e.g., a company with a debt load that exceeded our defined limit) but experienced a great outcome.

If that outcome was the result of luck (i.e., we can’t identify a driver), then we don’t want to do that again—we can’t verify that we can repeat the outcome! Meaning, the next time we invest in a high-debt company, we may lose big—we just got lucky this time.

As we repeat this process over time, we will begin to identify trends that we should mitigate (negatives) and opportunities we can leverage and exploit (positives).

This is how we effectively improve our investing mindset and process—systematically and rationally.

Like trading, doing so requires documenting our actions and then analyzing them against our actual outcomes.

Legacy Food Storage

Lesson #8: Review Your Overall Investing Performance Regularly

The eighth investing lesson we can take from the world of trading is that ultimate success requires reviewing our performance regularly.

Building on lesson #7 (after-action reporting and analysis of individual investments), we need to expand the scope of our performance reviews to include our entire portfolio.

I have found in my years of trading that I can miss the forest for the trees if I fail to step back and regularly review my overall performance.

While documenting and analyzing individual trades can provide a lot of valuable insights, I can miss larger trends if I don’t look at the big (macro) picture.

For example, my individual reviews of trades with a particular trading setup may indicate that my process is working. However, when I look at the performance of all those trades against my performance with other setups, I may find that they tend to significantly underperform.

Thus, it may be a better (more efficient) use of my capital to avoid that setup and focus on the more rewarding ones.

This is no different with investing!

We need to step back and examine our overall investing performance regularly. Because we are dealing with longer investing time horizons, we can do this quarterly, semi-annually, or even annually.

We don’t want to overdo this by employing too high a frequency—it is time consuming and adds little to no additional value. Furthermore, it can actually negatively skew our perspective due to short-run volatility!

The goal with these reviews is to help us identify broad trends. This means which components of our investing plan can be correlated to positive outcomes, negative outcomes, or neither.

Obviously, we want to eliminate negative items. However, we often overlook the components that are neutral—and there are typically far more of these than the clearly negative ones.

Those components that can’t be tied to positive or negative outcomes represent things that are not adding or subtracting value to your investing. We should seek to eliminate them in order to simplify and streamline our investing approach (see lesson #3).

Furthermore, it is important that we evaluate our performance based on the right metrics. This means that passive-income strategies should be primarily examined (weighed) based on cash flow performance—not capital appreciation (or depreciation).

This process can take years to fully implement but that’s what long-term investing is all about. However, we can glean critical insights from this approach that would otherwise be missed—insights that can have a tremendous impact on our long-run return on investment thanks to the power of compounding!

Lesson #9: Long-Run Investing Success Requires Realistic Expectations

Another critical trading lesson that we can apply to investing is that success requires realistic expectations.

A large percentage of failure in trading can be directly tied to unrealistic expectations (e.g., the belief that it is easy or a path to fast riches).

The same holds true for investing!

Whether you are a dividend-growth or dividend-value investor, passive-income investing is a long-term strategy. We must understand and embrace that—meaning we must have realistic expectations.

One of the biggest reasons that folks bail on passive-income investing is that they have unrealistic expectations and get disillusioned when they aren’t seeing rapid growth in their portfolio.

The strategy will work for you. In fact, I strongly believe it is the most effective approach to building both passive-income and wealth. However, it will take time and patience. Compounding is incredibly powerful—but it takes time to get that flywheel spinning and build momentum.

Once you build that momentum, the outcome is exponential—but in the beginning it will be excruciatingly slow and painful!

There is no free lunch, nor is their gain without pain. If you want to achieve a meaningful goal—such as financial independence, then you are going to have to have the perseverance to put in the work before you start to see the results.

That is the realistic expectation you must have!

A corollary to this is do not invest with money you may need in the next 3 to 5 years! That is not long-term investing capital.

Doing so will influence your expectations and very likely (1) put pressure on you to deliver unrealistic results or (2) limit your ability to absorb and weather short-run volatility—volatility that is inevitable and unavoidable in investing.

Furthermore, you need to be realistic about your own financial position. You may need to find ways to increase your income or decrease your expenses in order to expand your discretionary capital—additional capital you can then invest to increase your passive-income and total returns through compounding.

It’s a long-run game… not a short-run sprint!

To learn more about the proper mindset and expectations for long-term passive-income investing, I encourage you to read these great Wicked Capital articles on the topic:

Lesson #10: Don’t Shortcut the Process!

The final lesson we can take from trading and apply to our investing is that we should never shortcut the process!

Becoming a successful trader requires years of study (quantitative) and building experience (qualitative). It’s a process—one that takes time to accomplish.

Yet, folks jump into trading every day and attempt to shortcut that process in order to get ahead—oblivious to the fact that they are actually ensuring they will only fall behind and likely seal their fate as yet another addition to the failure statistics.

They don’t invest the time to study and learn technical analysis or how to properly manage trades and risk. Instead, they jump right into penny stocks (the worst place for them), go way too big (ignoring risk), trust ridiculously absurd trading “systems” obtained from a quick visit to YouTube, and blow-up their trading accounts.

It’s all about the process and investing is no different.

Investing is not difficult. It is really quite simple, and I believe anyone can be successful at it.

However, it requires a thoughtful, clearly-defined plan, effective process, and proper mindset. These three components are non-negotiables for ultimate success.

Just like trading, I see folks jump into dividend-growth investing who try to shortcut the process. They are unwilling to study and learn the craft. Instead, they resort to speculating—typically based on the “picks of the month” by some random shmuck they see on YouTube.

And when they fail and fall short of their unrealistic expectations, they blame the market, the stock picker, or the DGI and/or passive-income investing communities (and you can throw the FIRE community in there as well for good measure).

They blame everyone and everything else… except themselves. They refuse to accept personal responsibility for ignoring the process.

Benjamin Graham Investing Quote on Discipline Consistency and Thought

I have complete confidence that you can be successful and achieve your financial goals through passive-income long-term investing…

But you will never do it if you shortcut the process.

This lesson really encompasses everything we’ve discussed above.

Like trading, if you want to find success in investing, you will need to develop (1) a clearly-defined investing plan, (2) a simple but effective process (one that is predicated on quantitative analysis but supplemented with a qualitative component), and (3) a proper mindset.

Yes, this will require work and effort. Yes, you will have to invest that effort up-front. However, the return on that investment will surpass your greatest expectations over the long-term.

If you don’t take away anything else from this article, sear this into your mind: Don’t ever shortcut the process!

The temptation will always be there—avoid it at all cost. Your future you will thank you!


Trading is very different from investing. However, that doesn’t mean they don’t share some similarities.

As we’ve seen, these similarities provide as with some practical and beneficial insights that we can glean from the trading world and apply to our investing.

Specifically, we’ve explored 10 powerful investing lessons that we can garner from trading:

Again, my intent is NOT to encourage you to consider trading. Rather, I think my experience in trading over the years has provided some valuable insights that you can apply to your long-term investing.

Stick to your investing—it will pay huge dividends (figuratively and literally) in your future!

Take the time to build a solid foundation—develop your investing plan, process, and mindset. It is time well spent—time that will provide a huge return on your investment.

Finally, the best laid plans are meaningless if you don’t follow them! Document your investing activities and then analyze, review, and adapt your plan over time as needed. Don’t become distracted or lose your long-term focus and become a victim of investing disorientation—stay on course!

It’s a winning ticked if you’re willing to put in the time and effort!

Finally, if you’re interested in dividend-growth investing predicated on a value framework—you’re in the right place! We focus exclusively on helping others be as successful as possible with this passive-income approach to investing and we hope you’ll continue to return to our site to learn, grow, sharpen your skills, and find effective and positive ideas and motivation!

Soak it all in, take and use what you want, modify it to fit your unique situation, and keep building that portfolio with a solid process and winning mindset!

We also encourage you to follow along with our public Wicked Capital Passive-Income Portfolio (PIP) through our monthly updates on the website and by viewing the portfolio on M1 Finance at https://m1.finance/1zUclN2JL

It’s a great way to learn from a real-world example of building and managing a dividend-growth portfolio predicated on a value investing framework!

If you’re interested in starting your own portfolio using the M1 Finance platform (which we highly recommend), please consider using our referral link https://mbsy.co/sZVS3 and we’ll both get some free cash to invest!

That’s just one more reason to start your dividend-growth investing today! It’s never too soon to start working towards your financial freedom!

Legacy Food Storage


Doug is the founder of Wicked Capital. He holds an MBA, BBA (Summa Cum Laude), and AAcc from Liberty University and has over 20-years of corporate finance, accounting, and operations management experience--spanning the public, private and nonprofit sectors. He is a member of Sigma Beta Delta International Honor Society in Business Management and Administration, Delta Mu Delta International Honor Society in Business, and Tau Sigma Academic Honor Society. He is also proud to have served his country as a member of the 82nd Airborne Division. His professional wheelhouse is corporate financial reporting, analysis, and forecasting—buoyed by his passion for fundamental analysis and valuation. Doug has been actively engaged in trading and investing for several decades, with a focus on value and dividend-growth investing. He has authored several books and, when he's not busy living the corporate dream, trading and managing investment portfolios, he enjoys playing the drums and spending time with family--especially in the Outer Banks of NC.

More GREAT Educational Articles

Click HERE to view a current listing of all our portfolio updates!


Always remember, investing involves substantial risk of loss and is not suitable for everyone. The valuation of investments may fluctuate, and, as a result, you may lose substantial amounts of money. No one should make any investment decision without first consulting his or her own financial adviser and conducting his or her own research and due diligence.

You should not treat any opinion expressed on the Wicked Capital website as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of opinion for entertainment purposes.

The opinions are based upon information we consider reliable, but neither Wicked Capital nor its affiliates, partners and/or subsidiaries warrant its completeness or accuracy, and it should not be relied upon as such.

Past performance is not indicative of future results. Wicked Capital does not guarantee any specific outcome or profit. You should be aware of the real risk of loss in following any strategy or investment discussed on this website.

As noted above, strategies or investments discussed may fluctuate in price or value. Investors may get back less than invested.

Investments or strategies mentioned on this website may not be suitable for you. The material presented does not take into account your particular investment objectives, risk tolerance, financial situation, or needs and is not intended as recommendations appropriate for you. You must always make an independent decision regarding investments or strategies mentioned on this website. Before acting on information provided on this website, you should consider whether it is suitable for your particular circumstances and strongly consider seeking advice from your own licensed financial or investment adviser.

Copyright © 2019 Wicked Capital. All Rights Reserved