"What Do I Buy (Or Sell) Next?"

And Why This Is The Wrong Question

Introduction

“Just tell me…what do I buy next?!” This is the wrong question. The right question is: “What’s the best way to achieve my investment goals?”

Think of investing like grocery shopping. We (usually) go to the store with an idea of what we need, based on who we’re feeding, what is best for those are eating (a menu) and a financial boundary around how much we will spend.

Imagine going to the store and buying whatever “felt right” or things that your friends (or Instagram influencers) were buying. At one moment you know you need some bread, then in another you’d really want some cookie dough!

Grocery shopping without a plan is ridiculous.

Same with investing. Skip straight to “buying stocks” without a plan, and you’ll end up with a cart full of junk.

Instead, let’s consider a better investment plan that leads to sustainable investing.

“Just Tell Me What to Do!”

This is the most common plea I’ve heard in 25 years of working with high-net worth investors: “Just tell me what stock to buy.” Or sell.

This seems like a shortcut. But in reality, it’s a treadmill.

• You buy Stock A → it drops → you sell.

• You buy Stock B → it rises, along with Stock A → you regret selling A.

• You chase Stock C because someone smarter (or louder) says it’s “the one.”

“Investing” becomes an endless loop, that would any wonder what it’s all about. The market is a pro at making people feel lost and humiliating us while it’s at it.

Why Obvious Answers Don’t Always Work

When you are stuck with the question: “What next?”, the obvious answer is often to just do something…anything.

But every investor has a unique situation: goals, timelines, cash needs, fears. Giving you “my top stock pick” doesn’t just fail to solve your problem, it actually creates new ones.

That’s why brokers, advisors, and “finfluencers” love our dilemma. It’s the perfect sales funnel. If you’re asking “What should I do?” someone will happily sell you an answer.

The real solution isn’t a better answer. Often the best answer is found with a better question: “What’s the best way to achieve my investment goals?”

The Grocery Store Test

Picture this: You walk into a supermarket with no plan. You ask the first stranger you see, “What should I buy?”

They say apples. You buy apples. Tomorrow you need pasta. But you didn’t buy pasta. OK, you come back and ask again. The stranger say “Oreos.” Your fridge looks like a toddler stocked it.

That’s what investing without a plan looks like. A mess.

Instead, you probably shop like this:

• Budget: What’s realistic this week?

• Meals planned: What am I actually cooking? How many meals? Over how many days?

• List made: What’s a must-have vs. nice-to-have?

• Store chosen: Where can I find the right stuff?

And yes, you probably make that simple plan all in under 10 minutes.

Investing works the same way. Here’s the “shopping list” framework.

Step-by-Step Framework

The typical investor usually starts by trying to find the perfect stock, mutual fund or ETF. But we don’t buy groceries that way. Instead of going bottom-up (i.e., stocks first), go top-down.

1. Invest-ability (Budget): How much can you invest after all expenses? Golden rule: don’t invest money you’ll need within 12–24 months. Just $100/weekly or even monthly, done consistently, can turn into serious wealth.

2. Suitability (Menu & Restrictions): What fits your situation? Goals, risk tolerance, time horizon? Here’s a quick suitability “fit test” you can take. [Note: this opens in a new browser tab hosted by Canva. Content by The Other Side of Obvious.]

3. Allocation (Ingredients): If you’re making a cake, you don’t only buy frosting. Same here: balance stocks, bonds, cash, and other ingredients, based on your suitability (goals, time horizon, cash needs, etc).

4. Portfolio Holdings (Shopping Cart): Finally—you start buying. Now, picks matter, but only inside the structure of your plan.

Takeaway: The stock pick is the last step, not the first.

By going top-down, you make the important decisions first. Believe it or not, the gains you achieve are mostly a result of your allocation decision (i.e., stocks, bonds or cash), NOT which stocks you buy! If the allocation decision is wrong, your goal will take longer to reach.

Photo by Ashkan Forouzani on Unsplash

Why This Works

This approach transforms investing from a guessing game into a repeatable process.

It removes the pressure to “get it right” every time. It gives you a framework you can return to whenever markets feel chaotic (or your portfolio seems out of whack). And most importantly, it makes investing sustainable.

Because the truth is, the market will always throw curveballs. And your situation will change along the way. The difference is whether you’re reacting to chaos or sticking to your plan.

Your Turn

Take a few minutes and walk through this guide on investor suitability. It's like a fit test that you can take yourself.

Then ask:

1. What are my investment goals?

2. How much investable assets do I have to invest (or do I have that is already invested)?

3. What mix of stocks, bonds, cash will best help me achieve my goal? For most with a goal of growth, at least 70% stocks will be appropriate.

4. What is the best way to balance (or re-balance) my portfolio to achieve my goals?

Still have questions? You can Comment, DM me or Chat on the Other Side of Obvious Substack page and I am happy to respond.

So next time you feel the itch, “Just tell me what to do!”, picture yourself following a stranger around the grocery store, tossing their favorite snacks into your cart. Would you trust that dinner plan with your family? Probably not.

Investing is no different. Unless you really like a steady diet of Oreos.

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This publication is for brains, not bets. The Other Side of Obvious shares ideas, stories, and general financial information—not personalized investment, tax, or legal advice. Investing comes with risk (including losing money). Talk to a pro before you act. Please take time to read these important disclosures before you get started.