Five-Minute Win
This week’s Five-Minute Win: Automate one financial task.
Pick one thing you’ve been doing manually and put it on autopilot.
Maybe that’s setting up automatic credit card payments, transferring money to your investment account every payday, increasing your 401(k) contribution automatically, or sending part of each paycheck straight to savings.
I’ve become convinced that automation is one of the greatest financial superpowers. Every decision you no longer have to make is one less chance to procrastinate, forget, or simply be human.
Take five minutes today. Future You will thank you.
What financial decision could you make once instead of every month?
The Tax Superpower Nobody Talks About
One of the things I’ve been thinking about lately is that we spend a lot of time talking about how to save for financial independence, but not nearly enough time talking about what happens after you get there.
I think one of the biggest hidden benefits of FI is that you gain far more control over your tax return.
While you’re working, your taxes are largely determined for you. Your paycheck shows up every two weeks. You can contribute to retirement accounts, claim a few deductions, and that’s about it.
Once you reach financial independence, everything changes.
Instead of asking, “How much money did I make this year?” you start asking, “Where should this year’s spending come from?”
Should it come from a taxable brokerage account? A traditional IRA? A Roth IRA? Should I realize long-term capital gains while they’re taxed at 0%? Should I convert some traditional IRA money to a Roth while I’m in a lower tax bracket? How much ordinary income should I recognize this year?
Those aren’t questions most people ever have the opportunity to ask.
Having money in taxable accounts, traditional retirement accounts, and Roth accounts doesn’t simply give you three different buckets of money. It gives you three different levers to pull every year.
For many financially independent households, that flexibility can produce surprisingly low effective tax rates. The standard deduction shelters a meaningful amount of ordinary income. Long-term capital gains may be taxed at 0% if your taxable income is low enough. Roth withdrawals can provide additional spending without increasing taxable income. Traditional accounts can be drawn down strategically or converted to Roth over time.
None of these strategies are particularly exotic. The real advantage comes from having choices.
That’s why I don’t think financial independence is just about escaping a paycheck.
It’s about replacing a life where your income is dictated by an employer with one where you get to decide how your income is created.
That shift is easy to overlook, but I think it’s one of the greatest financial advantages available to people who achieve FI.
Financial independence doesn’t just buy your freedom. It gives you the flexibility to make the tax code work the way it was designed to work.
A Few Things…
A few things I found interesting this week…
šļø WhatsApp Voice Messages
If you travel internationally, you probably already know this. For everyone else, WhatsApp voice messages have become one of my favorite ways to stay in touch with friends and family. Instead of typing out a long text, you simply press and hold the green microphone button in the bottom-right corner and talk.
I love that voice messages preserve so much of what gets lost in a text. You hear the laugh, the excitement, the pause before someone says something meaningful.
My favorite feature, though, is that you can listen to voice messages at 1.5Ć or 2Ć speed. Somehow hearing someone’s actual voice is still more enjoyable than reading a text, even when they’re talking twice as fast. š¤£
š½ A Love of Learning
When we were in Ohio visiting Erin’s family, they were harvesting sweet corn from their property. I must have asked her parents fifty questions. That night I spent another twenty minutes asking AI how corn works.
I don’t know why that fascinates me so much, but I’ve realized I genuinely enjoy learning how things work. Once you become curious, the world starts revealing interesting details everywhere you look.
š Grocery Delivery
We’re continuing to experiment with grocery delivery, and when we got home from Ohio I ordered from Costco before we even unpacked the car. Two hours later the fridge was stocked and we completely skipped that familiar “there’s nothing to eat” feeling after a trip.
I’m surprised how much mental energy it saves. As a bonus, Costco has become my favorite place to stock up on Oikos Triple Zero Greek yogurt. Fifteen grams of protein for only 90 calories is hard to beat, and the price is usually about half of what I’d pay at the grocery store.
šļø Voice-to-Text
I can type pretty quickly, but speaking is always much faster. I’ve been using a tool called Wispr Flow that lets me dictate almost anything on my computer including emails, documents, any text input box I find, etc. What surprised me most is how well it formats everything automatically.
This has been one of the biggest productivity upgrades I’ve found in a long time. If you want to try it, here’s my referral link, which gives you a free month of the premium version (I get the same).
ā½ World Cup Withdrawal
I watched somewhere around 60 of the 104 matches during this year’s World Cup, so I’m going through a little bit of withdrawal now that it’s over.
Fortunately, I looked at my calendar and realized Arsenal’s Premier League season starts in just a few weeks. An added bonus is that my free Peacock subscription through Instacart+ means I’m already set to watch.
The Slightly Harder Choice
Someone shared a simple idea with me recently, and I haven’t stopped thinking about it.
When you’re faced with two reasonable options, choose the slightly harder one.
Not the dramatically harder one. Just the one that requires a little more effort.
That might mean taking the stairs instead of the elevator, walking instead of driving, cooking dinner instead of ordering takeout, or putting another hundred dollars into your investment account instead of spending it. None of those decisions feels particularly important in the moment, which is exactly why they’re so easy to dismiss.
Over time, though, I’ve started noticing a pattern. The slightly harder choice today often creates the easier life tomorrow. The workout makes getting older easier. Saving money makes work optional sooner. Cooking at home makes taking care of your health a little easier.
I’ve realized this applies to much more than money. Whenever I’m torn between two reasonable options, I find it useful to ask one simple question:
What’s the slightly harder choice?Ā Not because it’s always the right answer, but because it’s right often enough that it’s worth considering.
Around ChooseFI
A few things happening around the ChooseFI community…
š Community Wins
One of the most-loved parts of the newsletter is the Taking Action section, and it only exists because you share your wins. If you’ve made progress, Iād love to celebrate it. Hit reply to this email and send in your win.
š Local Groups
If you haven’t already, take 30 seconds to join your local ChooseFI group. You’ll automatically receive email notifications about meetups and events in your area, making it easy to connect with other people on the path to FI.
šļø Continue the Conversation
Have thoughts or questions about this week’s podcast? I’d love to hear them. Join the discussion on Episode 609, where Harvard psychologist Dr. Jasper Lee shares research-backed ways to have better conversations about money and financial independence with the people who matter most.
š Book Club
Our next book is Happy Money: The Japanese Art of Making Peace with Your Money by Ken Honda. Ginger will be discussing it with Jillian Johnsrud next month, so now’s a great time to grab a copy from your library. I’ll share details on how to submit questions and join the conversation in an upcoming newsletter.
āļø Travel Rewards
My Top Ten Recommended Travel Rewards Cards page is always up to date, including current welcome offers. If you’re thinking about your next travel rewards card, that’s the first place I’d look.
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