Recently, I’ve been experiencing a bout of financial hopelessness that’s been surprisingly hard to shake. Rationally, I know I’ll be OK, but mentally, I’m stuck in this negative loop.
It started after I decided to save money by flying Basic Economy to surprise my father for his 80th birthday. Saving ~$180 off Economy and ~$1,300 off First Class felt like a small win – something frugal, efficient, and strategically aligned with the whole Financial Samurai mindset.
Then we got into a small fender bender. The repair will cost our insurance company around $4,200, and we’ll likely face higher premiums when renewal time comes. I have no doubt my insurance company will try to get their money back, despite not having any accidents for over 10 years. It’s the same insurer that showed little grace after I made a terrible life insurance error.
In a single moment, one careless driving mistake erased the equivalent of 23 times the effort I had put into saving. After the incident, I was left wondering what the point was of trying so hard to save money.
More Financial Pain
Then I recently spent $1,900 fixing my car due to various mechanical issues. But the biggest problem – my malfunctioning electrical system – still isn’t fixed. After two mechanics, including a specialist, a brand new main battery, and even a 70-minute highway drive after a full Battery Management System reset, the “Low Battery” light still came back the next day.
Are there sudden electrical vampires lurking around? The last thing I want is for my car to shut down on the highway with my family inside. I'm completely at a loss and feel demoralized. My remaining hope is that I just need to go through several more morning cold-starts to get the battery management system properly recalibrated.
As a problem solver, this inability to solve my electrical problem is driving me bonkers. At this point, it feels like I’m shoveling $100 bills into a fire. My responsible “gamble” to repair the car and squeeze a few more years out of it has backfired. Instead of throwing $1,900 into repairs, I should have traded it in and leased a new vehicle.
Layer onto that the need to sell Treasury bonds to cover a surprise $20,000 capital call, plus more than $50,000 in property taxes for the first installment, and the financial burden starts to feel suffocating. At least I sold one property earlier in 2025, saving me ~$17,000 in taxes for this installment.
Maybe you’re carrying a heavy load of financial responsibility too. If so, I hope this article gives you the encouragement you need to keep moving forward. You are not alone.
Your Financial Independence Journey Will Be Full Of Doubt
Ever since I started writing about FIRE in 2009, I’ve made it a point to share the good and the bad. The bad parts matter more as they help people prepare mentally and emotionally for what’s ahead.
And here’s the reality nobody talks about: The moment you negotiate a severance package and retire early, you will second guess your decision. Immediately.
As the years go by and you encounter cash crunches, bear markets, pandemics, unexpected expenses, personal setbacks, and bizarre “bad luck clusters,” you will find yourself wondering whether it’s time to get a full-time J.O.B. again. During these times of misfortune, all you want is to regain a sense of stability and optionality.
The unfortunate reality is that the longer you’re out of the full-time workforce, the harder it becomes to jump back in. This is why I recommend doing something productive while FIRE. Try consulting at least once every three years, or building a skill, or maintaining a network connection. Just in case.
You Feel More Hopeless When You Lack Energy
Whether you’re still working or retired, financial hopelessness hits harder when you’re exhausted.
For most of my adult life, I’ve viewed financial setbacks as challenges I could overcome through grit. Higher rip-off health insurance premiums? Fine. I’d write more freelance articles, teach more tennis, give more Uber rides, or take on extra personal finance consulting.
But lately, even thinking about those activities has felt draining. As a result, I’ve paused my personal finance consulting offering until the new year. I also want to avoid any more car accidents, and I have no desire to push myself to write more than four times a week. On top of that, the hours I already spend teaching my kids tennis each week are plenty.
The two years it took to write, edit, record, and market Millionaire Milestones drained me. Managing our family’s finances through yet another turbulent year hasn’t helped. Parenting young kids, while incredibly rewarding, has also tested my limits. Ah, the joys of adulting.
At the end of the year, all I want to do is rest. Please. Yet my internal Provider’s Clock keeps ticking, reminding me of my mistakes and urging me to make up for them.
Other Examples Of Feeling Financially Hopeless
You may have experienced financial despair too. Some common triggers include:
- Being trapped in high APR credit card debt
- Making little progress on student loans despite working for over a decade
- Being unable to kick a gambling addiction despite knowing it’s ruining your life
- Feeling locked out of homeownership due to high rates and high prices
- Remodeling a home that is now way over budget and time because your contractor decides to hold you hostage
- Feeling stuck in a home that no longer feels affordable
- Watching healthcare premiums rise despite living a healthy lifestyle
- Living with a partner who is not on the same page with you financially
- Taking care of a partner with a disability, who is unable to work for more than a few hours a day
- Paying exorbitant private school tuition knowing the ROI is declining
- Watching AI crush your industry despite doing everything right
- Dealing with a roof leak you just can’t locate
- Having a neighbor build a two-year home addition blocking your view
- Being a top performer but denied raises because other departments are losing money
- Raising a child with severe medical needs and around the clock supervision
- Being stuck in a failing marriage on the path toward divorce
- Having terrible neighbors who blare the music, throw parties, and don't give a damn about the 10 p.m. noise ordinance
- Getting caught in a financial scam where you have no way of recovering your stolen funds
- Making a healthy six-figure income yet feel like you're scraping by due to economic inflation and lifestyle inflation
Have I missed anything? Feel free to share more examples. No one goes through life financially unscathed.
How To Overcome The Feeling Of Financial Hopelessness
Life can be immeasurably cruel. The longer we live, the more bad things will inevitably happen to us. Here are some strategies that have helped me and may help you when hopelessness takes hold:
1. Slow Down And Shrink The Problem to One Next Step
When life becomes noisy and obligations start stacking up, most of us plow forward without ever pausing to examine why we feel depleted. But awareness is the first step to rebuilding.
Slowing down doesn’t mean stopping; it means giving yourself enough mental space to observe your stress triggers, identify unsustainable commitments, and acknowledge the responsibilities that no longer align with your priorities.
Sometimes the exhaustion comes from obvious sources: too much work, too many deadlines, too many people needing something from you. Other times it’s more subtle: constant low-grade vigilance, worrying about money, or feeling like your identity is tied to relentless productivity.
Break things down into a single action: one bill, one call, one item sold, one hour of work, one dollar saved. Small wins rebuild confidence.
2. Rest before you reassess.
Most people accumulate commitments without any deliberate choice. Then one day you look around and realize your calendar is running your life instead of supporting it.
Pruning obligations through subtraction is not a sign of weakness or scarcity; it’s a sign of maturity. It means saying no to projects that drain you, stepping back from volunteer roles or advisory gigs that no longer excite you, and removing recurring tasks that don’t meaningfully improve your life. Cutting 20% of your commitments can restore 80% of your mental bandwidth.
You’re not broken, you’re probably just depleted. Prioritize sleep. A single weekend of genuine rest can ease more anxiety than a financial plan ever could.
If you haven’t tried it yet, attempt a 24-hour phone fast. It works wonders for your mental health. Can’t do a full day? At least turn off all notifications and check your phone only when you want to.
3. Reconnect with your purpose.
Money stress feels heavier when you forget why you’re grinding. Re-anchor yourself to your kids, your partner, your lifestyle freedom, your future self. Remind yourself of your ikigai – your reason for being. And if you don't have an ikigai, create one.
4. Rebuild systems, not motivation.
Most people try to fix burnout by forcing themselves to “get motivated.” The problem is that motivation is unreliable. It fluctuates with mood, energy levels, and even the stock market. Systems, on the other hand, create stability regardless of how you feel on any given day.
Put your finances on autopilot so that good decisions happen by default, not by willpower. Think of it as constructing a safety net that works even when you’re tired, distracted, or overwhelmed.
That might look like:
- Automating savings and investments so you don’t have to think about it or talk yourself into it. Money flows into your 529s, IRAs, and brokerage accounts whether you’re feeling optimistic or exhausted.
- Creating budgeting routines that give you clarity without emotional friction – weekly check-ins, monthly reconciliations, or simple percentage rules (e.g., 50/30/20).
- Pre-scheduling investing through dollar-cost averaging so you’re buying consistently instead of chasing market highs or lows.
- Building predictable income streams, whether it’s rental income, online business revenue, dividends, or T-bills rolling over. Predictability of passive income reduces fear and rash decision-making.
- Setting guardrails – like predetermined withdrawal limits, rebalancing thresholds, or spending caps – so you don’t rely on optimism or discipline to stay on track.
When your systems are strong, your finances keep moving forward no matter what’s happening in your life. And when your life gets chaotic, as it inevitably does, good systems protect you from emotional decisions that blow up years of progress.
5. Build a lifestyle that prevents future burnout, not one that recovers from it.
Learning how to forecast your misery is vital. Most people treat burnout reactively, once they’re overwhelmed, then they look for ways to bounce back. The solution is to design a lifestyle that’s hard to burn out from in the first place.
That means structuring your days around recovery, not around squeezing in recovery when you crash. It means intentionally balancing ambition with joy, obligations with autonomy, and productivity with restoration. It means avoiding commitments that drain you and leaning into the ones that energize you. And it means surrounding yourself with people who support your well-being instead of consuming it.
A burnout-resistant lifestyle includes:
- predictable downtime (take a nap if you can!)
- boundaries that protect family and personal time (lock your door or put a sign on it saying you're busy)
- creative outlets (write, make music, sing, draw)
- health routines you don’t negotiate (keep that weekly pickleball commitment going despite the frigid cold)
- financial systems that reduce stress
- cutting out negative people in your life
When you build your life around long-term resilience, you don’t just avoid burnout, you unlock a higher-performing, calmer, more meaningful version of yourself.
6. Remember your strong track record.
You’ve survived recessions, corrections, job losses, market crashes, mistakes, and emergencies. You have an undefeated record of getting through your toughest moments since you're still here.
Acknowledge your financial wins, no matter how small they feel. When despair gets loud, wins get quiet. But they’re there. You just have to force your brain to recognize them.
Some of mine:
- Buying the dip in March and April 2025 and keeping the faith the market would hold on
- Providing for my family for one more year
- Publishing a USA Today national bestseller
7. Remind yourself that you don’t always need to be winning
Many of us who chase big goals fall into the quiet trap of believing we must constantly be on an upward trajectory. If we’re not “winning,” we start feeling like something is wrong. But that mindset creates a fragile emotional system, one where even minor setbacks feel like existential failures.
When you hold yourself to a relentlessly high standard where every outcome must be optimal, you set expectations that reality simply can't support. And as the equation goes, happiness = reality – expectations. If the expectations keep creeping up, your happiness gets squeezed no matter how well you’re actually doing.
Lowering expectations isn’t a sign of complacency, it’s a safeguard for your mental health. It’s a reminder that second place, third place, or even no place at all can still be part of a successful long-term journey. Trying itself, is an admirable thing.
Too Much Optimizing In FIRE Land
As FIRE practitioners, we spend so much time researching, optimizing, tweaking, and hustling to improve our financial lives that we start believing every decision should be the perfect one. We love our spreadsheets! But markets, life, and timing don’t always cooperate. Even when you play the hand exactly right, you don’t always get the result you want.
Take poker, for example. You can start a hand with pocket Aces, the strongest position possible, and in a heads-up situation you’ll still lose about 20% of the time. In other words, even when you make the best possible move, variance still has its say.
Rather than expecting to win 80%+ of the time, consider the emotional benefit that comes with adopting a 60%–65% expectation. That’s roughly two wins for every loss, a healthy ratio. Losing money from our investments and having surprise expenses is inevitable.
Stop trying to win every battle. Focus on winning the war. Because life rewards persistence far more reliably than perfection.
8. It's OK to ask for help
Finally, if you feel like there’s simply no way out of your financial hole, don’t be afraid to ask for help. It may take swallowing your pride, but your friends and family will often want to support you. Being able to help someone you care about in need is one of the greatest honors.
Remember, asking for help doesn’t make you weak, it makes you human. Even the most successful people have leaned on mentors, loved ones, or professionals at some point. Whether it’s financial guidance, emotional support, or simply a listening ear, reaching out can give you the perspective and tools you need to start moving forward again.
Life Is Hard, Keep Going
Financial stress distorts reality. Sometimes it convinces you that problems are bigger than they are, mistakes more costly than they seem, and the path forward narrower than it really is.
But the truth is: You’ve handled worse. You’ll handle this too.
And once your energy returns and cash flow stabilizes, the hopelessness will fade, just like it always has.
Readers, when have you felt financially stuck or even hopeless? What was the moment that made you pause and wonder if things would ever improve? More importantly, how did you push through that period and get back on track? I’d love to hear the strategies, mental shifts, or routines that helped you regain momentum after a financial setback. Your stories may be exactly what someone else needs to hear today.
Suggestions To Improve Financial Serenity
One of the most effective steps I ever took to reduce financial anxiety was securing matching 20-year term life insurance policies for my wife and me. I spent years searching for an affordable option and kept coming up empty, until Policygenius helped us compare multiple providers quickly and for free. Once we finally had our policies in place, an enormous weight lifted. We both felt real peace knowing that if the worst ever happened to either of us, our children would still be financially protected.
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Lots of great nuggets here. The one that resonated with me was, in summary, winning 2 out of 3 is still winning.
I have a habit of obsessing over the losses when I should be more grateful for the wins. I also have to remind myself that an achieved net worth goal is still success no matter how you got there.
Thanks for another of your appreciated personal posts.
“Loss Aversion” empirically shows that the emotional negative impact of a financial loss is at least twice the amount as the positive impact of a financial gain. This makes sense on so many levels of evolution and logic. If we’re doing a bit (or a lot) better today than yesterday we are moving in the right direction; conversely, if we are moving a lot (or even a little) in the wrong direction we are losing ground to what has been attained, and we forecast that loss into the future despite past performance.
I am still a self-imposed victim of this as even though our net worth post-retirement has grown in almost a perfect proportion with our actual expenses (i.e. for every two dollars we’ve gaining, we’ve spent one dollar and reinvested the other). Despite that I truly have a negative emotional reaction to the days we lose ground, while I am mildly happy or neutral on the days we gain. As I know our end point is ultimately finite, and we’ll be fine in even almost all scenarios (excluding the very worst cases that are apocalyptic where no one will be ok), it never feels good to back up.
Well said about loss aversion. I feel the same way.
The negative emotion to losing on our investments makes perfect sense, especially if we no longer have steady active income to comfortably cover our expenses. We are ultimately most dependent on our investments in retirement.
Thankfully, the past three years have been great. But we know the correction is coming again. Just don’t know when exactly.
Be well, Sam. I am a control freak and the pressure I put on myself to optimize and be perfect will sometimes boil over into my relationships, which isn’t fair to the ones I deal with and love, or me either. The FIREd life places a higher burden of financial responsibility on our shoulders, there is no job and salary to backstop mistakes. Every penny counts, and we are literally counting them all the time. I like the idea of automating more of my investments, I feel the pain of making suboptimal choices. Having a process, like DCA, might relieve some burden, anxiety, guilt.
And on days when I just can’t figure out how or what to do… I clean something, just one thing. Load the dishwasher, fold clothes, sweep the floor, clean a window. That always makes me feel productive and like my day was not wasted.
A good habit to feel productive. I’m going to wash my car tomorrow to make it feel new, even though it has recently caused me so many problems.
During financial negative times, it sure would be nice to have that steady paycheck.
Auto electrical issues are the worst to resolve. The more features you have the more sorrow later as electrical issues fail first. A $900 Body control module is one example.
Negative events seem to happen in strings for some reason. We have to accept them and know that things will be better after we resolve them.
Rest almost always helps when I feel flooded and overwhelmed. Naps are a life saver.
Remember all the positive you have and be grateful for your station in life.
Yeah, they are so complicated and endless, I’m afraid to buy a new car due to even more electrical components.
I had a nice soak in the hot tub and a short nap today. That was nice.
I’m also thankful the Low Battery light did NOT come on this morning. This morning was the 5th cold start, and it was suggested I may need to do 10-12 cold starts for the batter management system to properly recalibrate.
Fingers crossed! I just hate wasting money.
“What was the moment that made you pause and wonder if things would ever improve? ”
Keeping my eyes on the prize: freedom.
I had a lot of setbacks early on and it was often hard to continue, sometimes even to continue to exist. To say I didn’t have a supportive family-of-origin would be an understatement, so it came down to remembering that, while I was crawling through the sewer pipe (Andy Dufresne style), the pipe would one day end. I would emerge blinking in the sunlight and have to reassure myself that I had in fact gotten out. Whatever I did after that was mostly my choice.
When I finally got to the work-is-optional stage, I held what I did there to a high value of time standard. Once going to work gave me little beyond a paycheck, I left. I’ve read here too much about one-more-year syndrome.
And decades after all this, I have to say it’s been worth it. I hope anyone who’s there right now can take some comfort from someone who made it through.
“while I was crawling through the sewer pipe (Andy Dufresne style), the pipe would one day end. I would emerge blinking in the sunlight and have to reassure myself that I had in fact gotten out. Whatever I did after that was mostly my choice.”
Love this so much. In fact, it was part of my intro in my WSJ bestseller, Buy This Not That. Eventually, the crap will end.
FREEDOM! (with your hands to the sky as the rain washes over you!)
I’ve been experiencing less cash flow myself lately and it’s a stressful experience. Anxiety creeps in, doubt and fear take a grip, and it can feel like a spiral of overwhelm. What helped me yesterday night was looking at my YTD dividend and interest income. I’m trying to calculate revisions for my estimated taxes and needed that info. It helped remind me that even though other things are spinning in my life, I’ve done some things right so that my money is working for me while I’m busy doing other things. Seeing that dividend/income report helped bring me some comfort.
But my bigger stresser recently isn’t financial, it’s emotional and tied to some very complex matters with a relative. I wake up to distressing news, go to bed receiving more distressing news. And frankly I feel suffocated. Even though your tips above are perfect for financial hopelessness, they are actually very applicable to all types of stress including what I’m experiencing on the emotional front right now. I normally don’t have any issues with high blood pressure, but have been so distraught my whole body is affected. I’m going to take your suggestions to heart and also remind myself of the powerful “full benefit” mindset that the Navy Seals use. Cuz I certainly need it right now. Thanks for all that you do Sam.
I like the idea of checking out your investment income. I am nearing retirement and it heartens me to know my projected budget (with some extras in it) is covered by interest and dividends and I shouldn’t need to touch principal unless I want to. Having “needs” covered like that allows me to relax and not worry so much about future costs I can’t control.
I’ve been reading your work for many years (online and print), and this might be my favorite article! You’ve put some very sage advice out around optimizing, always feeling the need to win and improve.
It is a struggle at times to recognize when “good enough” might actually be the best course of action! I’ve put a lot of effort on this over the past year and feel more content, grateful, and optimistic than ever!
Best of luck chasing the electrical problem! I went through that years ago, did some ridiculous actions to try and extend the life of the vehicle, and in hindsight I should have probably moved on earlier! I’d still say it was my favorite vehicle and I was emotionally attached to an object, oh well!
Great post. Currently I feel like my “rowboat” has only one oar. Just going around in circles. One of the “downsides” is the credit card debt. It’s minimal and can be corrected but I can’t stand having it. Definitely, can wear one down thinking how irresponsible it is to carry a balance on them. Such a waste of hard earned money.
Whenever I have anxiety about a huge expense, I calculate its percentage in relation to my net worth. It’s often a VERY low percentage. That quickly provides peace. When JL Collins was stressing over paying for an “expensive” dinner, Mr. Money Mustache reminded him that he’s living a free life because his investment income is far greater than his working income. That is so true. His index fund portfolio easily pays for EVERYTHING he wants. That’s where I am right now. That’s the goal of being FI. That’s why I took my family to South Africa last August. I’ve earned it. FS, don’t forget that you live a financially free life. Hopefully, that diminishes your financial anxiety.
^^^This^^^
I have to remind myself of this (or be reminded by looking at statement on occasion) whenever considering first class flights, or unexpected expenses, or other larger-ish purchases.
Staying in our agreed-upon and very closely tracked budget each and every month without any splurges is great for the pocketbook, but puts unexpected stress on the spouse, and because they hear about the budget, our kids.
It definitely is good to have perspective on the expense related to one’s net worth and investment returns.
I wrote a new post today about the difference between cash flow and investment gains. It’s hard for me to co-mingle the two.
I hope you go on another international trip or two!
For me, this is a very important point. Humans always take on the characteristics of the environment they’re in. You live in the city with a lot of activity and wealth. It’s easy to get caught up in the , I’m never enough or never have enough. Further, if your kids don’t succeed on the level of this environment, they may feel like a failure. Most of us are not exceptional, but we can still live a great life of contribution and happiness. Buffet lives in a lower stress environment where he has time to think and there’s not going to be as much comparison envy. Perhaps a move to a lower cost-of-living area or Hawaii to be by your parents would be something that helps both you and your children. Just a thought from someone that lives in a smaller , low cost of living community. Best wishes.
It’s exhausting thinking about expenses that pile up, especially when they’re unexpected AND it don’t payoff.
On a smaller scale, this happened to me when I tried to repair my induction range. The touchpad died, so I went to YouTube, diagnosed the issue, ordered the parts, and went to work. Then I failed miserably. I inadvertently placed the new control board flat on an aluminum strip before connecting the power and yeah, that thing exploded immediately.
The cost of hiring someone including parts was going to be around $650. The parts alone were $350. I ended up paying $700 (having to buy the parts twice) to fix the issue, AND go through the unnecessary headaches (and frankly, danger) in the process. It sucked.
But you’re spot on about #6, 7, and 8. I had to laugh at the situation and remind myself that I have a strong record of successful DIY projects/repairs, was reminded that it’s OK to spend money for convenience, and I definitely felt humbled (and reminded by my wife that I should just ask for help more often).
Anyway, keep us posted on your car journey. Curious to see what you choose.
I feel your pain. It is so frustrating to try to spend time and money to save money, only to have it backfire. You’re trying to do the right and responsible thing, but life isn’t having it.
“ paying for twice” is exactly what I am annoyed with because I could’ve just saved the $1,900 on fixing and just leased a new model Y for example. Now I’ve got this song, Cost, which I’m wondering whether to dig a deeper hole in or not. Because if I fix something else, maybe something else will break.
10 years old… for European cars at least, I think that truly is about the switching point.
My husband’s just back from a doctor’s appointment where he was told he has a MRSA infection in his hand. He snagged his hand trying to repair a toaster oven. It healed but a nasty infection blew up last week and he ended up in the ER on IV antibiotics. They took blood for culturing – hence his callback this morning. We have insurance but are anticipating bills comprising many multiples of a new toaster oven! As a person with controlling tendencies, I’m constantly reminding myself that I have control over next to nothing. Still, a pox on malfunctioning toaster ovens
I’m curious – I would not have thought you’d be a “lease the car” guy. Are you doing that to protect your downside having to sell an older EV?
Given the tech is improving rapidly with EVs, it feels like a lease is prudent. I did lease a Honda Fit from 2014-2017 for 3 years for $250/month. It was easy, cheap, and a breeze to return to the dealer.
In 3 years, we may move to Honolulu, so not having to sell a car when we leave is attractive. Just hand back the keys.
The older I get, the more I’m optimizing for simplicity.
Sage advice. Under rest, I’d add getting at least 8 hours sleep daily to the mix.
Absolutely. The more rest the better. For the past eight years, one of my top three priorities has been to try to let my wife rest as much as possible during the day.
However, she has changed course and recently decided to not nap anymore to try to get a better night’s sleep. So I’ll try to adapt accordingly by encouraging her to go to sleep earlier and not follow my sleeping habit of late nights, early mornings bc I’m fine with 5-6 hours of sleep either way a nap.