💰Your 2026 Investing Calendar - Month by Month

Hi friend,

Something that happens to almost all of us in January — we make a bunch of financial goals, and by March they’ve all gone out the window.

You tell yourself you’re going to:

And then life happens and you fall off the proverbial wagon.

But not because you’re lazy or ‘bad’ with money. It’s because you’re trying to do everything at once.

If you’re anything like me, you get overwhelmed, and decide instead of sitting down and really looking at that monthly budget again, there’s a Netflix show calling your name.

And before you know it, another year is gone and you’re still in the same financial situation you were when it started.

But I’m about to help you change all that.

Today I’m giving you a complete 2026 Investing Calendar. Every month I’ll share one or two specific tasks so you have a clear path forward to help you conquer that anxiety and make sure nothing slips through the cracks.

And while some months may not seem like they relate to investing, I promise, it’ll all make sense at the end.

Let’s dive in…

Task: Calculate your current net worth

How: Net worth = Assets - Liabilities

Take anything you OWE, and subtract it from what you OWN.

Things you OWN include but are not limited to:

Things you OWE include but are not limited to:

Knowing your net worth and recalculating it every so often will help you know if you’re trending in the right direction financially.

Task: Pull your free credit report

How: Can do this through your credit card company (AMEX, Capital One, Chase etc.), or go to annualcreditreport.com for a one-time pull.

Check for any errors, accounts you don’t recognize, address changes, late payments that shouldn’t be there, and dispute anything that’s wrong immediately.

⭐Pro Tip: set up credit alerts via text or email so you always know what’s going on.

Task: Create a plan to pay off all your high-interest consumer debt

How: Choose a debt repayment strategy. There’s lots out there, but some popular ones are the debt avalanche and debt snowball methods. One method has you paying off your highest to lowest interest rate first, while the other has you tackling the account with the smallest balance first. Choose whichever method works best for you.

I feel like a broken record, but you can’t out-invest your high-interest consumer debt.

Even if you have a healthy retirement/investment account balance, any interest you’re paying on things like credit cards, car payments, payday loans etc. is eating up most, if not all, the gains you’re getting in the market.

The math simply doesn’t math.

A 12% return on your S&P 500 ETF is getting destroyed by that 24% interest rate on your AMEX Platinum.

Task: File the previous year’s income taxes (unless you qualify for an exception)

How: Gather up all your W2’s, 1099’s etc. and DIY (TurboTax etc.) or through your CPA

We all hate it, but we all have to do it. April is tax month and we all have to file them.

But there are (legal) ways you can do this strategically to keep more of your hard-earned money in your own pocket rather than Uncle Sam’s.

You may love that big tax refund you got last year, but the truth is — that just means you paid too much in and gave the government an interest-free loan, when you should’ve been taking that extra money each month and investing it. No bueno.

So instead, adjust your withholdings on your W4 so that you’re paying just the right amount.

Task: Price check every policy you have (home, car, renters, life etc.)

How: Call your insurance companies and ask them about any current offers or discounts they’re offering.

If they push back, tell them you’ve been in contact with their competitors and you’re not afraid to jump ship. It’s amazing the deals you can get when you threaten to leave!

Task: Review your retirement contributions — are you on track to max out that Roth IRA or 401K?

How: If you can, bump up your contributions through your paycheck or automatic investments so you hit the max now, or by the end of the year

For 2026, the max contribution limits for IRA’s are $7,500/year if you’re under age 50, and $8,600 if you’re over 50.

Limits for 401K’s are $24,500 if you’re under 50, and $32,500 if you’re over 50. There’s also super catch-up contributions if you’re in your 60’s - so take advantage of these if you can!

If your income is too high to qualify for a Roth, consider doing a back door Roth. A strategy of converting nondeductible contributions into a traditional IRA/401K, so you can still take advantage of tax-free withdrawals when you hit age 59 1/2.

Don’t forget you can also invest your Health Savings Account (HSA) if you’re under a High Deductible Health Plan (HDHP) for triple tax advantages — money that goes in is after-tax, tax-free growth, and tax-free withdrawals.

And if you’re self-employed, make sure by now you’ve set aside those Q1 and Q2 estimated taxes — don’t wait for year-end surprise!

Task:

How: Go back to your January budget where you figured out your net worth.

Are you sticking with it? Where are you overspending?

If you wanted to save $10K this year, you should be at around $3,500 by now. Are you close or way off? If you aren’t, ask yourself why.

Look at your income as well. Did you receive any bonuses or raises this year? Did you start a side hustle?

Do you still have that new income saved so you can invest it, or did you let lifestyle creep get in the way and eat up all that new money?

Task: Compare your own investments’ performance against certain benchmarks or ETFs you believe in like the S&P 500, the NASDAQ 100, the total U.S. stock market etc.

How: Use features within your account(s) like comparison charts, or Google Finance, to see how your own investments are doing compared to the actual index they’re supposed to be tracking.

It’s also a great time to rebalance if you need to.

Let’s say you had an investment really take off the first 6 months of the year and it grew dramatically to make up a large portion of your portfolio — don’t forget to redistribute those profits elsewhere in your portfolio so you’re not invested too heavily in one specific stock or sector.

⭐Pro Tip: also evaluate the fees you’re paying for your investments. Because even 0.5-1% in management or advisory fees can end up costing you a ton of money over the life of your portfolio.

Task: Audit your spending category by category

How: Pull your last 3 months’ of statements, categorize every transaction (or update your budget app if it does this for you). Once you have the real numbers, you’re going to make real decisions.

If you’re ok with $400/month on restaurants and eating out that’s fine, but then cut somewhere else so you free up more money to invest and become an asset, not a liability.

The point is having accurate data so you can be intentional with your money. Make it work for you, instead of the other way around.

Task: Find ways you can increase your income or optimize it

How: If you have a 9-5 job, go to websites like Glass Door, Pay Scale and others to figure out your market value. If you find your salary is 10-20% below average, build a case and negotiate with your boss on a potential raise whenever your company usually does them.

If you’re not able to get a raise at your W2 job, consider starting or building up your side hustle. If you’re not sure where to start, watch some YouTube videos, or listen to podcasts to get a feel for what skills are most sought after in the marketplace right now. Then take some time to go learn those skills to increase your value and marketability.

Ex. Uber/DoorDash, grocery deliveries, consulting, teaching, freelance/contract work.

If you can find an extra $200-$500/month, and do that for a few years, if you invest that money correctly in the market with an average 8% annual return — in 5, 10, 20 years, that’s going to turn into tens of thousands, if not hundreds of thousands of dollars in retirement.

⭐Pro Tip: Do NOT go spend a ton of money on a side business right away. Start with resources you have available now, learn the skills, and then if people are validating your ideas through offering to pay you money, then think about investing some capital into equipment upgrades, mentorships, certifications etc.

Task: Look for ways you can reduce your current year’s tax bill

How: If you can, max our your 401K, IRA or HSA in the last two months of the year. Or open a Donor Advised Fund and donate appreciating assets (like your investments) to causes you believe in, while also reducing your taxable income. It’s a win-win!

If you have taxable investments, look into tax loss harvesting. Sell losing positions to offset gains elsewhere inside your portfolio. Then buy a similar investment to maintain your exposure to that industry or sector.

If you’re self-employed, go talk to your CPA now, rather than waiting until they’re ready to pull their hair out, so you can discuss things like year-end deductions, estimated quarterly taxes etc.

Any one of these things could help you save thousands, maybe even tens of thousands of dollars in taxes depending on how large your income or business is.

Task: Create your holiday shopping budget

How: Make a list for everyone you’re buying for and assign dollar amounts.

This is the month that can make or break your entire year.

You’re not being a Scrooge by limiting your holiday spending. You’re actually setting yourself and your family up for future financial success, and avoid going into January stressed and broke.

Ideally, start this the end of November, before Black Friday and Cyber Monday hit so you can get deals on things you were already planning to buy.

⭐Pro Tip: If you have high-ticket items you’re buying online, put them in your cart and wait a few days. Over half of all ecommerce businesses have ‘Abandoned Cart’ email marketing where they’ll send you a discount to encourage you to actually hit that checkout button.

The old adage is true:

If you fail to plan, you plan to fail.

I hope this calendar gave you some direction, and things to think about to make 2026 your best financial year ever!

And if you really want to accelerate your wealth-building, join the waitlist for my next Quiet Wealth Small Group Investing cohort. Inside, you’ll get 4 weeks of live training with me and a small community of investors just like you, looking to set themselves up for future success.

Everything from making sure you have your accounts set up properly, to knowing what investments are right for your risk tolerance and money goals, to building a long-term plan going forward, so you can continue investing with confidence.

As a special thank you for joining, I’ll send you three of my most requested investing resources that will kickstart your growth:

Charlie’s Pep Talk Audio Files.

To remind you when things get tough that you CAN do this and I’m always here in the background cheering you on!👇

Margin trading is a form of borrowing. It lets you leverage securities you already own, to purchase additional securities, protect your account from overdraft, or access a line of credit.

Example: Let’s assume you want to buy 1,000 shares of of Apple stock at $10/share. You would need $10,000. But say you only have $5,000 in cash available in your investment account.

With a margin account, you can use your $5,000 in cash and borrow the other $5,000 “on margin” to make the purchase. Without a margin account, you’d need to have the entire $10,000 in cash in your account to make this trade.

So how does a margin loan affect your investment?

Assume Apple stock rises in value from $10,000 to $11,000 and you sell it.

You would pay back the $5,000 margin loan and realize a profit of $1,000. That’s a 20% return on your $5,000 investment. Without a margin loan, you would’ve spent $10,000 in cash and only realized a 10% return instead.

What happens in the event the stock price falls?

Let’s look at the flip side of the example above.

Assume the market value of the Apple stock you purchased with a $5,000 margin falls from $10,000 to $9,000. Your equity - which is the value of your position minus the loan balance of $5,000 - would fall to $4,000.

That’s a 20% loss from a 10% decrease in market value.

What about interest?

Just like with any loan, you will begin accruing interest charges on the date your trade settles. The rate you pay depends on your outstanding margin balance - known as the margin debit balance.

Margins loans also have no set repayment schedule, but do require a minimum “margin requirement”.

As long as you maintain the required level of equity in your account - or your margin requirement, you are good.

Typically the initial margin requirement is 50% - this is the amount of cash or other securities you must maintain in your account for your purchase.

Once you start buying stock on margin, you’re required to maintain a certain level of equity in your margin account. This requirement varies depending on the type of security.

For example, a stock usually has a maintenance requirement of 25%, but your brokerage may require a higher amount.

What securities are eligible for margin trading?

While most types of securities are eligible, CDs and money markets are not.

Bottom Line:

Margin accounts provide a great opportunity for you to leverage your investments to help you increase your return.

But always weigh the benefits and risks in your own personal situation, and consult a professional before investing in this type of account.

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Disclaimer: this content is for educational and informational purposes only, and is not legal, financial or investment advice. Always do your own research before investing, and consult a licensed professional. Charlie and OJD LLC are not responsible for any losses or decisions made based on this content.