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The Hidden Cost of Playing It Safe
ChooseFI Weekly

The Hidden Cost of Playing It Safe

Brad Barrett
By Brad Barrett · · 8 min read
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Five-Minute Win

This week's Five-Minute Win: Step outside within an hour of waking up.

Spend 5+ minutes outside tomorrow morning. If you've listened to Dr. Andrew Huberman's podcast, you've probably heard him talk about morning sunlight as one of the simplest ways to set your circadian rhythm and help your body know when it's time to sleep later that night.

I try to take a 15-minute walk each morning, which lets me get some steps in while getting that morning light.


Be Conservative Intentionally

I've noticed something interesting when talking with people who are getting close to financial independence.

They'll start with the 4% rule, but decide that's a little too aggressive, so they'll use 3.5% instead. Then they'll assume their investments will earn significantly less than historical averages, just to be safe. They'll estimate that their spending in retirement will be higher than it is today. They won't count Social Security because they don't trust that it'll be there. And then they'll keep a couple of years of expenses sitting in cash in case the market crashes. 

Let’s be clear: every margin of safety has a cost.

If you assume higher expenses, lower returns, a lower withdrawal rate, no Social Security, and a large cash buffer all at once, you can create a financial plan designed to survive a future that's dramatically worse than almost anything we've historically experienced.

That's certainly safe. But it might also tell you that you need another $500,000 before you can retire. And if saving that additional money takes another three or five years, the margin of safety wasn't free. You paid for it with three or five years of your life.

I'm not arguing that we should build financial plans with no margin for error.  But if I’m going to be conservative, I want to be conservative intentionally.

If I'm using a lower safe withdrawal rate, what risk am I protecting against? If I'm also assuming unusually poor investment returns, am I protecting against a different risk, or have I just accounted for the same bad market twice? If I'm ignoring Social Security entirely, what am I assuming happens to it? If I've already built plenty of flexibility into my spending, do I need another enormous buffer on top of that?

The goal isn't to create the most conservative spreadsheet possible. The goal is to build a plan that gives you enough confidence to actually use it.


A Few Things...

A few things I found interesting this week...

✈️ PointsYeah Daydream Explorer

Most of us search for flights by deciding where we want to go and when we want to go, and then trying to find a decent flight to make it happen.

But what if you don't really care where you go?

That's why I love PointsYeah's Daydream Explorer. Instead of searching Richmond to Paris on a particular week, I can essentially tell it: Here are the airports I'm willing to leave from. Show me where I can go with my points.

From there, you can filter for things like business class, the points programs you have access to, how many points you're willing to spend, taxes and fees, number of stops, and even how many seats you need.

And this is where FI flexibility becomes a real travel advantage. If I don't really care whether my next trip is to Amsterdam, Copenhagen, or Madrid, I'd much rather see where there's an incredible points deal and let that help determine the trip.

I've been using PointsYeah for years, and somehow when I first wrote about Explorer I buried one of the coolest ideas in travel rewards: Instead of deciding where to go and then searching for an award, sometimes it's more fun to find the amazing award and let that decide where you go.

🧾 Check Your Social Security Record

I saw a post from The FIRE Playbook listing websites retirees should bookmark, and one of them prompted me to do something useful: log into my Social Security account at SSA.gov.

It takes just a few minutes, and there are two things worth checking.

First, look through your earnings history. Social Security has a year-by-year record of the income credited to you, and those numbers ultimately feed into your benefit calculation. It’s worth making sure nothing looks obviously wrong or missing.

Second, take a look at your personalized retirement estimates at different claiming ages. One consideration for the FI community: you can adjust your expected future earnings in their calculator. If you’re planning to stop working early or substantially reduce your income, that may give you a more realistic estimate than assuming you’ll continue earning at your current level.

A genuinely useful five-minute financial check.

🎮 StarCraft Is Still Ridiculously Good

I’ve been playing the original StarCraft again lately, a game I loved back in college and have returned to off and on for years.

I’m reminded every time I play how demanding it is cognitively. You’re gathering resources, building units, expanding your base, scouting, defending, attacking and constantly deciding what deserves your attention next. It feels like I’m making dozens of tiny decisions every minute.

I don’t know whether it technically qualifies as “brain training,” but it certainly feels that way to me. I have to stay focused, make quick decisions and constantly adjust when my carefully constructed plan falls apart.

Mostly, though, it’s just incredibly fun and challenging.

🎓 A Student Loan Deadline Worth Knowing

I talked with Travis Hornsby from Student Loan Planner on the podcast recently, and one deadline is worth knowing:

If you have a Federal Direct Loan originated after July 1, 2012, enrolling in autopay by September 30 can reduce your interest rate by 1 percentage point through June 30, 2028, instead of the normal 0.25% autopay discount.

If you're already enrolled in autopay, you don't need to do anything. The increased discount should happen automatically.

A full percentage point isn't insignificant. On a $50,000 student loan balance, that's roughly $500 of interest per year before accounting for the declining balance.

If you have federal student loans, it's worth checking before September 30.

💰 Expectations Are a Liability

Sahil Bloom said something on the Afford Anything podcast that I've never thought about quite this way before:

“Expectations are your single greatest financial liability. If your expectations rise faster than your assets, you will never feel wealthy. You will never be rich. Because you'll just be chasing whatever more you convince yourself will lead to your future happiness.”

We spend decades accumulating assets, but if every increase in income and net worth is accompanied by an increase in what we believe a wealthy life is supposed to look like, the finish line keeps moving.


This Company or the Field?

Years ago, I used to religiously watch Pardon the Interruption on ESPN, and they had a question that I've always loved:

This team or the field?

Would you take one team to win the championship, or every other team combined?

It's such a simple question, but I’ve come to use it all the time when thinking about probabilities in investing and life.

Let’s look at Tesla.

Whatever you think of the company or Elon Musk, Tesla's accomplishments to this point are extraordinary. It helped force the automobile industry toward electric vehicles and became the dominant name in the category. If you recognized that possibility early, you were spectacularly rewarded.

But investing is always about what happens next.

Tesla's valuation today depends on much more than selling cars. A significant part of the story is what Tesla might become in autonomous driving, humanoid robotics, AI, energy, and other enormous future markets.

Instead of asking whether Tesla can succeed in those industries, I've started asking the old PTI question:

Tesla or the field?

In autonomous driving, would you rather bet on Tesla, or Waymo and every other company in the world working on autonomy?

In humanoid robotics, would you rather bet on Tesla's Optimus, or Unitree, Figure, Boston Dynamics, the rapidly growing Chinese robotics industry, and everyone else who will enter the market over the next twenty years?

Even in electric vehicles, where Tesla has already been wildly successful, I'd take the field. If Tesla still controlled 15% of the entire global automobile market twenty years from now, that would be an astonishing accomplishment. It would also mean the field controlled 85%.

The current valuation seems to require extraordinary success across several of these categories.  If you use The Field Test, that seems unbelievably unlikely.

The Field Test is useful far beyond Tesla of course:

When an investment thesis requires a company to dominate an enormous future market, you need to compare it with everyone else in the world combined.  And know that those companies aren’t sitting still waiting for this presumptive winner to take a bow.


Around ChooseFI

A few things happening around the ChooseFI community...

🎉 Community Wins

One of the most-loved parts of the newsletter is the ChooseFI Community Taking Action section, and it only continues to exist because you share your wins.  Hit reply to this email and send in your win.

📍 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.

Marina, one of our admins in LA, posted this after their latest meetup:

“Investor Policy Statements in the books… this will be a continued conversation in future meetings…”

I loved this. They turned the meetup into a brainstorming and accountability session around their own investor policy statements.

🎙️ Continue the Conversation

Have thoughts or questions about this week's podcast? Join the discussion on Episode 616, where Sean Mullaney, Cody Garrett, and I talk about the many different ways to give money and invest for your children.  This was an important episode, and Sean and Cody will be in the comments answering your questions.

✈️ 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. 

If you apply using our links, ChooseFI earns a commission at no additional cost to you. This is how we're able to keep the podcast and newsletter ad free. For nearly a decade, we've made the deliberate choice not to interrupt the podcast with traditional ad breaks, and I'd love to keep it that way. If you're going to apply for one of these cards anyway, using our link gets you the same offer, costs you nothing extra, and helps us keep ChooseFI ad free. We're incredibly grateful.


ChooseFI Community Taking Action This Week

Christopher

My wife and I went to a fundraising event in Spring of this year. We knew in advance that they would have a silent auction that would go toward a great cause. We had one item that we both agreed we would like to bid on. It was a 4 night 5 day stay in Park City, UT in a really nice town home. We both agreed on a number that we did not want to go over.

Fast forward to the last few minutes of placing our bid we hit our number and in the last 5 seconds were outbid by $25! We were both a little bummed out about it because we thought we had won.

Two weeks later we reached out to the family that had the place in Park City to see if they had any openings for the summer. Turns out they did. Here is where it gets good.

We got the place for 6 nights and 7 days and we paid less (by $1,000) than what we had originally bid on. On top of that this family covered the cleaning fee and it was remodeled right before we got there! God had other plans for us that were much better!

Anand

My recent 1% win is reaching the 6-month milestone of early retirement at age 45 and realizing that the biggest transformation wasn't the math—it was the total elimination of the "Sunday Scaries."

After more than a decade of diligent saving, investing, and listening to ChooseFI, I finally stepped away from my corporate law career earlier this year. The initial buildup was intimidating: setting up our automated withdrawal pipeline (living off a high-yield cash buffer fed by a ~3.2% withdrawal strategy) and navigating the bureaucratic maze of ACA marketplace health insurance with pre-existing conditions.

During week one, my brain was so wired to the corporate grind that I kept waking up early to check an empty work email inbox.

The real breakthrough hit on my first Sunday evening post-retirement. For nearly two decades, Sunday nights meant mental exhaustion—reviewing meeting agendas, tracking deliverables, and dreading the upcoming workweek. Looking at my calendar and realizing there were zero meetings to prepare for was the most freeing feeling of my life.

Six months in, our portfolio has continued to hum along on autopilot, and my days are full of things that actually matter: unhurried mornings with my young daughters, playing competitive league pickleball, and sitting down with a camera to record oral history interviews with my mom so our kids know their roots.

For years I thought financial independence was about reaching a final number, but the real win is getting complete ownership of your time.

I put together a transparent video breaking down what our first 6 months of early retirement actually looked like—from the psychological disorientation to our withdrawal setup: https://www.youtube.com/watch?v=JXprqkelSMw

Cindy

My 1% this week is that we paid off our car loan. It was costing $1,100 in interest a year but we didn’t feel comfortable shelling out a lump sum when we first bought it, despite being FI at the time (the psychology of money is tough!) Fast track to yesterday when I walked into the bank and paid it off in full. Partner and I are officially RE and realized it didn’t make sense to carry that additional APR.

Emily

Hi! One small change that has made a surprisingly big difference for me is using ChatGPT as an interactive life coach. I do brief daily check-ins where I brain dump everything I’m thinking about that day. ChatGPT organizes it, helps me identify priorities that will most move the needle on my goals, and challenges me on where I’m wasting time or energy. What I especially like is that I can tell it about improvement areas I’m working on (like active listening) and it incorporates timely reminders about when and how to focus on them into my daily check-in. The process is effortless, which makes it easy to keep doing. I’ve only been doing this for about a week and I’m genuinely shocked by how much progress I’ve made on some long-standing personal goals in such a short time.

Alexa

I was thinking about moving this fall when my lease was up but I wasn't finding a good rental in my price range. I used Claude to write a rent negotiation script which resulted in my rent going down by $100 a month at renewal instead of the $20 increase they initially quoted me ($120/mo in savings). The best part is that I can save the difference monthly to cover moving costs for when I eventually decide to buy or rent another place. It never hurts to ask!

Joseph

I decided to quit my dead end job and travel the world at 29, I am currently in Australia on a working holiday Visa and my frugal win would be that I have recently increased my savings from A$4000 to A$15,000 in 2 months of working as a bartender and not having to pay accommodation fees due to staying in one of my employers studio hotel apartments. Before finishing this working stint I’m on track to save a total of A$20,000! I do this by allocating 20% of my wage to spending, and the other 80% gets split into various saving pots for my longer term goals and travel plans.

In 4 weeks time I’m going to spend about half of what I’ve saved travelling the country and then move on to New Zealand to start my next phase. Which is to save NZ$100,000 so that I can travel for 2-3 years without working a day! All whilst still investing into my future every month via my global funds.

I especially enjoyed the episodes where you have spoken about where you can save money and making small almost unnoticeable changes sometimes to save a lot more money in the long run and also where you use your personal experiences and personal examples of what you do in your lives and what mistakes you made along the way on your path.

I would give the following advice to anyone who will listen:
Life is good, and if you’re not feeling that yet it’s only around the corner so keep going! Also don’t let yourself be the person who gets older saying “I wish I’d done ….” Get out there and seize!

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