Planning to fail
"Everyone has a plan until they get punched in the face." –Mike Tyson
Because people (ourselves included) don’t always say what they mean or mean what they say, plans won’t always go according to plan. But any plan is better than no plan…so long as you act.
In this one:
Planning
Plans
Illusions
Also, some discomfort and some ‘magic’. Let’s glow.
STORY
Don’t play yourself
You can strategize, you can plan, you can do everything to the letter. Or at least convince yourself that you have all bases covered.
But plans don't always go according to plan.
Many people believe that the perfect plan is a guarantee for success. But the perfect plan is the one that leads to action. Plans are worthless without action.
Without action, planning is a mirage that tricks you into thinking you’re making progress when you’re not.
“To think too long about doing a thing often becomes its undoing.” —Eva Young
The greatest trap in planning is the illusion of progress—mistaking preparation for action and confidence for certainty. It’s a double-edged sword that cuts many both ways.
On one side, planning can give you courage to face uncertainty. On the other, it can keep you in situ while time marches on. And as you wait to perfect it, new variables emerge.
We like to take credit for our genius when things go as we planned. But when they don’t, we find it easier to blame everything but ourselves.
Taking ownership of your actions means owning all outcomes.
In an uncertain world, it's impossible to prepare for every scenario. You didn't plan your own existence, yet you tell yourself you can plan how everything in it will unfold.
Here’s an uncomfortable truth: Planning can masquerade as productivity when it’s really just avoidance.
It can quickly become the impediment to action and a disguise for indecisiveness. It’s the perfect excuse because, after all, if you’re ‘still planning’, you never have to risk failing.
Plans exist to guide your actions. To focus your energy on what matters because you can’t do everything. Rely on them too rigidly, and you’ll miss the bigger picture.
The best plans are tightly knit but loosely held.
At their core, plans are simulations designed to prepare you, not predict the future.
Even when things go “according to plan”, there are innumerable external factors that you can’t or don’t account for that influence the positive outcome.
Planning limits surprises. That's all.
So plan, by all means, plan. But don’t let planning lull you into a false sense of progress. Planning happens in place, progress happens in motion.
EXPLAINER
Bond vs bond fund pt. 3: Plan, plan, execute
If your investment strategy defines what you aim to achieve, your investment plan answers how you will execute it in the real world.
An investment plan ensures that your investments align with your financial situation, risk appetite, and long-term goals. While investment planning can be broad, we’ll address five areas today: allocation decisions, investing frequency, selection criteria, rebalancing & exit, risk management.
Applying Your Plan
Now, let’s bring this back to the original question:
“Does it make sense to invest in a bond fund if you’re already buying bonds directly?”
The following 5 questions give you a structured approach that simplifies the decision, ensuring each choice is intentional rather than reactive. Your investment plan refines the answer by applying key execution factors:
How much will you invest?If you’re working with smaller amounts, a bond fund allows diversification without needing a lot of capital.
If you have sufficient capital, buying individual bonds gives more control over returns.
How often will you invest?If you’re making regular contributions, bond funds provide an easier way to invest consistently.
If you’re investing in lump sums, individual bonds let you lock in specific rates.
Which specific bonds or bond funds will you choose?If your strategy prioritizes stability, a high-quality bond fund or government bonds may be better.
If you’re seeking higher returns, corporate bonds or actively managed bond funds could be an option.
How will you adjust over time?If you need flexibility, bond funds allow automatic reinvestment and adjustments.
If you prefer to hold to maturity, direct bonds offer more predictability.
How will you manage risk?If you want to reduce the risk of default, government bonds or high-quality corporate bonds may be ideal.
If you are concerned about interest rate risk, shorter-duration bonds or actively managed bond funds can help navigate rate fluctuations.
Beyond the Basics
While these questions help structure your decision, an investment plan can go even deeper, depending on your needs. Other considerations that come to mind are taxes, liquidity and reinvestment planning.
You don’t need to address all these factors at once, but keeping them in mind ensures your plan is holistic and adaptable as your financial situation evolves.
From Planning to Action
At this point, your investment strategy and plan should be shaping a clearer decision. Ideally, your plan should be structured to support your strategy. But there’s one more step: understanding the trade-offs and risks of each option.
In the next part of this series, we’ll look deeper at key differences between individual bonds and bond funds, helping you contextualize how to evaluate which approach best fits your needs when choosing between two assets.
CURIOUS
Who’s fooling whom?
We like to see what we want to see. Sometimes it’s intentional. Other times, it’s simply how we’re wired.
As humans, pattern recognition is fundamental to our survival. But life itself is a subjective experience. And what we perceive isn’t always what’s there.
I recently had to explain to my 9-year-old daughter that our brains don’t just passively receive reality, they simulate it. To illustrate this I used one of my favorite illusions, Troxler’s fading, where an image seems to disappear if you stare at it long enough.
That conversation got me thinking about an even more common illusion. One we fall for daily, often without realizing it: apophenia.
Apophenia is our brain’s tendency to find connections and patterns where none exist. It’s why we see faces in clouds or believe unrelated events are meaningfully linked.
But this pattern-seeking instinct doesn’t stop at visual illusions. It extends to how we think about the future. Just take a peek into the rabbit hole in the short video below.
Just as our brains trick us into seeing meaning where there is none, they also trick us into believing a well-structured plan guarantees a predictable outcome. It doesn’t.
Planning is useful, until it becomes a crutch and an illusion of certainty in an unpredictable world.
Look out (and look in).
"The eye sees only what the mind is prepared to comprehend."
— Robertson Davies
I disappear
Perfection is an illusion, and waiting until you're ‘absolutely sure’ is just another way to avoid starting.
If your mind can create certainty where none exists, what else might it be convincing you of?
Believe your eyes and have the best week visible.
AG
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