Once both our children began school full-time in 2024, my wife and I had more breathing room. At least six hours a day of free time. No more wrangling toddlers in the chaos of the early years.
I used the time to finish Millionaire Milestones, which became a USA Today bestseller in 2025. Now I'm working on a new book about why your children will be OK, also with Portfolio Penguin, out in 2027.
My wife decided to get her teaching credentials online through UCLA over six months. Then she started substitute teaching at our son's first preschool nearby to gain real-world experience.
She loves kids and is great with them. If she keeps it up, she'll have a year of full-time classroom experience under her belt within three years. And if we relocate to Honolulu, maybe she could find a teaching job at one of the schools we'll be applying to. A built-in community from day one.
Supporting Her In Her New Endeavor
One way I support her is by driving her to and from work around my school drop-off and pick-up runs. Being a preschool teacher means standing on your feet for six of the 7.5 to 8 hours of the day. Her school also does daily nature walks to Golden Gate Park. Shuttling her saves nearly two miles of walking up and down a hill after an already exhausting day.
One afternoon I picked up the kids around 4:45pm, then swung by to get mommy at 5pm. She was tired. Everyone was hungry. We drove around the corner to a popular bakery and I parked in a red zone between two driveways of an autobody shop, not double parked. Three minutes, tops. The auto body shop had workers parking client cars out front all the time, including ours years ago. I figured I was safe.
I was not.
When I came out, a parking attendant was already writing me up, despite my wife and two children inside. I asked nicely if he could let it slide as my wife could have easily moved the car. He said no. The law is the law.
No Good Deed Goes Unpunished
What stung wasn't just the ticket. It was the math.
My wife had just spent eight hours on her feet earning $26 an hour. That's $208 gross. After taxes, because we have passive income and online income that pushes us into a higher bracket, her take-home was closer to $145.
I wanted to do something nice. Pick up my tired wife. Feed my hungry kids. Instead, I might have wiped out her entire day's take-home pay with one poorly parked car.
This is financial despair in its purest form. You work all day. You try to do something kind for your family. And you end up paying money just for the privilege of having worked.
We checked online for two weeks and saw nothing. So we forgot about it, and felt hopeful.
Then, 62 days later, at an SF Giants game, an e-mail from my tenant:
“Hi Sam, sorry for notifying you late. Parking ticket for you. Just found this today under some stuff in the garage.”
The ticket was dated August 31. Due date September 21. I was reading it on September 22.
$108 ticket plus $45 late fee. $153 total.
That's the gut punch that turns a good evening into a quiet drive home.
Financial Despair Is More Common Than People Admit
This is such a small story. I know that.
But I think a lot of people reading this know exactly what financial despair feels like. You work hard, do the right thing, try to take care of your family, and then something stupid and random erases it. A parking ticket. A medical co-pay that arrives six months late. Having a toddler swell up from an egg allergy and riding a $3,000+ ambulance ride to the ER. A bounced direct deposit. An overdraft fee triggered by a school fee you forgot about. A new government tax.
The math starts to feel rigged. Not because anyone is plotting against you, well maybe, but because the margins are just so thin. When you're living close to the edge, one $153 surprise isn't an inconvenience. It's a week of groceries. It's the difference between making rent on time or not.
That financial hopelessness is real. Even people doing everything right, showing up every day, working hard, raising their kids, still get blindsided by bad luck and bad timing. The system doesn't care how tired you are. The late fee posts anyway.
And once you start doing the math in your head, it gets darker. After federal taxes, state taxes, payroll taxes, and whatever surprise the city throws at you, the gap between what you earn and what you actually keep can feel insulting. That's when financial hopelessness starts to creep in. Not because you're failing. But because the rules seem designed to keep you running in place, forever.
I got a little of both. Despair and anger.
The Last Time I Felt True Financial Despair
The $153 parking ticket stings. But the last time I felt genuine financial despair, the kind that keeps you up at 1am staring at the ceiling, was 2008 and 2009.
I was in my early 30s, working in equities at a time when equities were collapsing. My net worth got slashed by 40% that took 10 years to build. Colleagues were being laid off in waves. The job I had worked toward since college suddenly felt precarious. The entire financial system, the one I had built my career inside, felt like it was coming apart at the seams.
What made it feel like despair, and not just stress, was the helplessness. No amount of working harder was going to fix a global credit freeze. You could do everything right and still lose. The rules had changed overnight and nobody had told you.
But that period of despair also rewired how I thought about money permanently. No longer was money sacred, as it could disappear in an instant. I also began quietly building the financial buffers that would eventually let me walk away in 2012.
Financial despair, it turns out, was the tuition I paid for financial freedom.
Financial Despair Can Also Be A Turning Point
What I've learned over the years is that financial despair, as miserable as it feels in the moment, is one of the most motivating forces in the world. Not because suffering is good. But because when something costs you enough, you actually change.
When I was working 60-hour weeks in finance and San Francisco passed a retroactive income tax targeting high earners, my effective tax rate shot to nearly 40% and my marginal rate hit around 56%. I was not happy. That financial despair is what pushed me to figure out how to negotiate my own severance and walk away in 2012.
Pain planned my way out of that job, and my life is much better as a result.
Same lesson applies now. The next time I pick up my wife from work, I'm not getting out of the car. Not for snacks, not to open her door, nothing. We're going straight home.
In the process, we'll spend less at local shops and restaurants. We'll eat slightly less unhealthy foods. And we'll save and invest more money. Three unintended wins from one expensive lesson.
And because I had apparently forgotten I was a taxpaying San Franciscan with rights, this $153 reminded me to actually use the 311 system. Now, I've argued before that the people who pay the most taxes should receive the least services, as a form of cosmic justice for earning too much. But just this once, after paying $153 for the crime of feeding my family, I'd like to feel like I'm getting something back. The city charges plenty. May as well use what I've paid for.
Here's what you can request by calling 311 or using the SF311 app:
Street & Sidewalk Maintenance
- Fixing potholes and broken roadways
- Repairing damaged sidewalks and tripping hazards so I don't twist my ankle
- Fixing broken streetlights or missing traffic signs, maybe even wash them, which I did on my block with detergent and a brush
- Removing abandoned vehicles left more than 72 hours
Waste, Cleaning & Public Nuisance
- Clearing illegal dumping (furniture, mattresses, appliances)
- Removing graffiti from public property
- Cleaning streets and sidewalks after dumping or waste
- Scheduling free bulky item pickups
Trees, Parks & Infrastructure
- Clearing fallen trees or dangerous hanging limbs
- Reporting broken playground equipment or damaged park facilities
- Clearing blocked storm drains causing flooding
The Way Out Of Financial Hopelessness
One parking ticket shouldn't derail your financial life. But it can change your habits, your awareness, and your willingness to push back in small ways.
The people who eventually escape financial hopelessness aren't the ones who avoid all bad luck. They're the ones who get enough of it to finally stop tolerating the things that weren't working. They change their routines. They question the systems around them. And they start demanding something back for what they pay in.
If there is one concrete step to take right now, it's this: calculate your real hourly rate. Take your monthly take-home pay, divide it by the actual hours you spend earning it, including the commute, the prep, the decompression time after work, and the mental bandwidth it consumes on weekends. That number is almost always lower than people expect. And once you see it clearly, every unnecessary expense stops looking like a small thing. A $153 late fee isn't just $153. At $20 an hour after taxes, that's nearly eight hours of your life you'll never get back.
Seeing the true cost of things in hours, not dollars, is one of the fastest ways to stop leaking money and start building real buffers. Your motivation to save and invest more will go through the roof! It also makes you question what you really want to do with your time.
My wife's $26/hour salary won't make us rich. But she shows up, she's building something real, and she cares deeply about what she does. That matters.
The $153 is gone. The lesson, and the 311 call I'm about to make about the pothole in our neighborhood, will stick around a lot longer.
Financial despair is real. But so is the momentum that comes after it. Sometimes the best tickets are the ones that finally wake you up.
If You're Feeling Financial Despair, You're Not Alone
If this post resonated with you, I'd love to hear your story. Leave a comment below.
- Have you ever felt like you ended up paying money just to go to work?
- What was your version of the $153 parking ticket? A surprise bill, a late fee, a tax surprise?
- How did financial despair or financial hopelessness end up changing your behavior for the better?
Track Every Dollar So Nothing Catches You Off Guard
One reason financial despair hits so hard is because most people don't have a clear picture of where their money is going until something goes wrong. A late parking ticket. An overdraft. A tax bill that arrives out of nowhere.
The free tool I use and recommend is Empower. It lets you link all your accounts in one place so you can track your net worth, monitor your spending, and actually see the full picture of your financial life. No more surprises buried in the garage.
Empower also offers a free consultation with a licensed financial professional if you have at least $100,000 in investable assets. Sometimes all you need is one conversation to stop the bleeding and start building a plan. It's worth doing. Schedule a free consult here.
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Seems living in San Francisco is annoying..first the rules about tennis courts and now parking ticket when someone is in the car…
Life is tough! Just got to hang on and survive.
It’s a reminder why I opted out in 2012. But with children, I had to reject myself back into society.
I moved from NYC to CT but my OB was sill in NYC. A missed appointment resulted in a $50 late fee that went to my old NY address and eventually collections. That cost me 25bp extra for a mortgage I applied for shortly thereafter. Awful. And would have been nice to receive a call from my doctor’s office before collections. Never again. And paid off the house early.
Ouch!
financial despair is watching your net worth take a massive hit. You are 47, closing in on FIRE by 50. At 40 you get married have kid(s) and then 7 years later get divorced. Bc you are a good dude you give your ex 1/2 the kid time and you give her your house and you continue paying the mortgage via child support. And now you look at Zillow and see what buying a comparable house down the road costs at today’s pricing and 7.5% interest. Your hard work toward fire starting from zero is essentially erased. All you can see on the road ahead is more working, but your prime earning years are over. To the readers facing this situation there are many steps to the road back but letting go of your feelings of anger and despair is the most important one. When you’re crammed into an apt with your kids, the feeling of financial despair will surround you like a tornado, but there is always a road back. You made millions the first time, you can do it again.
Great attitude! And at least you have a wonderful kid(s) who are worth more than anything in this world.
Fight on!
Being a carfree cyclist for last 4 decades, I never paid attention to car parking costs. It is lifestyle if you live in a big city, that’s all possible and with transit for cold snowy winter. And even easier if no young kids in your life.
As for 311, excellent reminder to make use of it for needed repairs noticed by citizens, and also post photos of potholes. Quite honestly in a huge big city or thinly staffed municaplity, staff haven’t got time to drive around every single street several times of year, to make note of things for repair. Just complaining to a friend over coffee…is the wrong thing to do since it doesn’t achieve anything.
I’m curious Sam, was the e-mail from the same tenant who had the fire alarms stacked up in a pile on your garage floor?
(the one who lacked urgency or common sense)
‘-Hi Sam, sorry for notifying you late. Parking ticket for you. Just found this today under some stuff in the garage-‘
If so, I think it would be prudent to change your mail address that the council has on their records to a different residence, or a PO box. You’re not wanting a tenant to have access to your personal mail either.
Nope, other tenant. Yes, good to change address.
But, I like having at least one thing registered to my properties, like utility bill or whatever as proof or ownership. Maybe doesn’t matter, but I like the continuity just in case there some type of weird ownership conflict or whatever.
Okay, thank you for explaining the reason why Sam. I don’t own any rental property, only my own home outright (in the UK). So I don’t really understand the importance, or relevance of this. I thought a property deed, title deeds, would state ownership outright, outwith of having a mortgage?
Regardless, it’s good to know you had a reason.
And sorry about your ticket. Taking a chance in a no parking spot just isn’t worth the hassle. Was everyone out if your vehicle? or was the ticket issued with your family in it?
Family was inside.
I heard the UK housing market is down 20 to 30% since the peak. Is that true? What’s going on over there?
I’ve not been following prices, but regardless, long term for my property the value has increased thankfully. Some places see higher increass than others.
That was probably an uncomfortable experience for your family!
1995, I had recently purchased my first house and money was tight, living pretty close to paycheck to paycheck. I received an overdraft notice from my bank, Wells Fargo, and notice on my mortgage statement my last check did not clear. I had the money to cover these obligations, and I knew so. I visited the local WFB branch to investigage, as there was no on line banking at the time. Turns out I had deposited my previous paycheck at the ATM into my savings account, not checking. Yes, my error, pushing the “savings account” button. WFB had declined six checks, starting with my mortgage – the largest – and working down the smallest check that would not clear. Charged me a bounced check fee, if I recall. $25, for each NSF check. I spoke with the bank manager, discussing the error and noting I had funds to cover the checks in my savings account. Could WFB grant me a pass on the NSF fees, given my ten plus years banking history, excellent credit and honest deposit error? Nope, the fees apply. As did fees for the other NSF checks I accidentally wrote. Total cost for my deposit error was over $350 bank and payee fees, money I just barely had and was stretched to pay. Probably 15 hours take home pay at the time. I paid the WFB fees, opened accounts at a different bank and closed the WFB accounts. Given my financial trajectory the last 30 years WFB lost at least 50x what it would have made had I remained a customer. At the time I decided to rent a room in my house, giving me more cash flow. And I double check all my financial transactions, too, though very few are at the ATM anymore.
It is not easy (all all) living in the role of a working mother in a dual income family. However, even with years of challenges under my belt, I still always advocate that “working” towards something will pay off in the future. This may be hard to remember day-to-day as you may be literally breaking even. Keep swimming!!!
Yeah I got defrauded out of 6 figures, and chose to pay a lawyer 5 figures to go after a judgement of uncertain value. At least future potential victims may see the case as a warning. Oof.
Getting a parking ticket stings, and working hard for pay that barely covers the basics stings even more.
Your piece brought back a flood of memories from my time as a graduate student at Cal, living on a modest fellowship that barely covered tuition and basic expenses. Back then, a parking ticket or dealing with smashed car windows (which happened 3 to 4 times, despite leaving nothing inside) was a genuine disruption. It meant photocopying library books instead of buying them, living off potatoes instead of getting Korean BBQ at Asian Ghetto, or leaning on credit cards because loans were not an option.
I deeply resonate with the broader point you made about how brutal it feels when unexpected fees eat away at hard-earned income:
At the same time, I would offer a gentle counterpoint on the framing. In this specific scenario, parking in a red zone and having the vehicle registered to an address you no longer monitor were not cases of doing everything right and getting hit by bad luck. They were avoidable missteps. Just like when I used to get dinged because I forgot street-sweeping hours on Tuesday mornings, the ticket was ultimately on me, even if the timing and the cost felt awful.
I share this from a place of care and from personal experience. As my financial situation has improved over the years, I have caught myself occasionally feeling a subtle sense of entitlement. It is easy to think that because we pay significant taxes and work hard, the city ought to give us grace when we cut a corner. But parking regulations and red curbs exist for practical safety reasons, and paying taxes does not exempt any of us from everyday civic rules.
There is plenty of valid frustration here: dedicated teachers are drastically underpaid, parking in SF can be maddening, and our public support systems often lag behind other countries. But distinguishing between systemic unfairness and self-inflicted mistakes is a grounding exercise in perspective and personal accountability.
Appreciate you sharing the raw thoughts as always, Sam. Rooting for your wife in the new teaching role, and hope the SF street drama gives you both a break.
Absolutely, it was absolutely my fault for parking in the red zone, and there’s nobody to blame but myself.
In the end, I appreciate the ticket and the struggle to try to get ahead. It reminds me not to take anything for granted and to keep on fighting for financial freedom.
But based on the feedback so far, it’s nice to see that nobody is struggling with financial despair today. How are you doing and what is your financial situation?
I like getting the pulse of the community and it seems like everybody is doing great. So that should be good for our Investments.
i’m all good now – no longer a poor PhD student. =) VCX was a nice bump too. =)
Cool. Don’t forget to send over your best ideas along the way. Good to give back!
Getting a parking ticket stings, and working hard for pay that barely covers the basics stings even more.
Your piece brought back a flood of memories from my time as a graduate student at Cal, living on a modest fellowship that barely covered tuition and basic expenses. Back then, a parking ticket or dealing with smashed car windows (which happened 3 to 4 times, despite leaving nothing inside) was a genuine disruption. It meant photocopying library books instead of buying them, living off potatoes instead of getting Korean BBQ at Asian Ghetto, or leaning on credit cards because loans were not an option.
I deeply resonate with the broader point you made about how brutal it feels when unexpected fees eat away at hard-earned income:
At the same time, I would offer a gentle counterpoint on the framing. In this specific scenario, parking in a red zone and having the vehicle registered to an address you no longer monitor were not cases of doing everything right and getting hit by bad luck. They were avoidable missteps. Just like when I used to get dinged because I forgot street-sweeping hours on Tuesday mornings, the ticket was ultimately on me, even if the timing and the cost felt awful.
I share this from a place of care and from personal experience. As my financial situation has improved over the years, I have caught myself occasionally feeling a subtle sense of entitlement. It is easy to think that because we pay significant taxes and work hard, the city ought to give us grace when we cut a corner. But parking regulations and red curbs exist for practical safety reasons, and paying taxes does not exempt any of us from everyday civic rules.
There is plenty of valid frustration here: dedicated teachers are drastically underpaid, parking in SF can be maddening, and our public support systems often lag behind other countries. But distinguishing between systemic unfairness and self-inflicted mistakes is a grounding exercise in perspective and personal accountability.
Appreciate you sharing the raw thoughts as always, Sam. Rooting for your wife in the new teaching role, and hope the SF street drama gives you both a break.
It feels like my wife is paying to go to work. This is a corporate job that consumes more than 40 hours / week. Long commute resulting in a very high nanny cost, paying for more conveniences, less time with me and the kids, etc. I’m grateful to have learned about FIRE earlier in our careers before kids, which motivated me to learn about and start investing. Now that we’ve reached FI (but not REed because of the golden handcuffs) and free time is extremely limited, this has motivated me to buy your book and start planning our layoff negotiations.
Well I JUST had an interesting conversation with my now 24 year who is going to grad school. She is dating a boy and said to me “I want to be able to stay home to raise my kids like you did…it gave us the best childhood ever”….that’s all I needed to hear to STOP the regret of getting heavily educated, going through infertility to have 3 kids, and worked for 15 years… I choose to stay home then. (Thank God I was able to)!!!!
You need to not pay for grad school then
The worst parking experiences I’ve had are in Whistler, Canada. These huge parking lots are filled with grocery stores, Tim Hortons, restaurants, and more. As a Texan accustomed to large parking lots, I casually parked and grabbed a coffee at Tim Hortons. It was raining, and I completely missed the signs. When I returned, I found a ticket on my windshield. Apparently, these parking management companies have cameras and all sorts of AI monitoring systems to hassle drivers. I ended up paying a whopping $90.
If you see multiple of the same comment, I am sorry. The post comment button wasn’t clear whether it posted or not. I clicked multiple times.
oh man that is so frustrating. Parking tickets are the worst and living in an urban area makes them basically inevitable. I too know the pain of missing payment deadlines by one or two days and it’s usually from a medical bill or a parking ticket or some other one-off. One time I had a medical bill come to me via a debt collecting agency bc either the bill went to an old address, got lost, or I forgot. In the end it didn’t really matter what the cause was because it was annoying in and of itself. I could have spent hours trying to fight the extra fees but I chose to save myself the time and pains and just pay it off and move forward.
I try to set myself 30-45 day reminders to follow up on bills for ad-hoc things now but inevitably there will be another time in the future that something goes awry again and I’ll get dinged with extra fees.
But anyway, I totally get your story and know that pain. Hopefully you won’t have another unexpected ding like that for awhile.
Personally, I think you should run for Mayor of SF. If I kept getting jammed up by local government, I’d be itching for something different. You want freedom and convenience, they want your money.
I swear we’re living parallel lives. Thank you for sharing yourself, your experiences and your lens. I used to feel this ‘financial despair’ a lot. It’s because I’m a refugee immigrant and grew up without a lot of money and saw my parents stressed about money. So I grew up with and still have to a large degree a ‘scarcity mindset’.
I counted every dollar and opportunity cost in my head. My mind was constantly counting the dollars that could be wasted. For example: why buy this pair of jeans at retail when I can wait for a sale and/or coupon and/or get 10% back with the sponsored credit card or even better just got to CostCo and pick up the Kirkland brand even though the pants I’m wearing are worn through and thin.
Rinse repeat for 22 hours of the day.
Then I got a driving ticket a few years back for changing lanes over a white line to get to the quicker exit while my mom and kids were in the car. Several cars had just done it and it’s common for that particular section of the highway for many people to do it as the main highway lanes are backed up during rush hour. But I got singled out to pay the penalty.
I went ahead and paid the ticket. I also deliberately declined traffic school to lower the points on my insurance. I told myself I was ‘rich’ and all this was a rounding error and I should value my time more.
That was hard. But I did it and carried the higher insurance premiums as an inverse lesson that not everything should be about dollars and some ‘waste’ and inefficiency and freeing my mind a little from the mental daily grind of counting economic resource calories was my reward for grinding it out and doing all the ‘right’ things most of my life.
I dunno if that really changed my life much, but it hasn’t hurt it and that’s part of the lesson I’m trying to learn.
Thanks again,
Thomas
I resonate with your comment about a scarcity mindset. I grew up poor but with a mom who was dead set on getting rich. She taught me so much, but also put some things in my head I still can’t let go of. She always made me decide if what I was about to buy was a want or a need. I could almost always come up with a reason it was not a need and didn’t buy it.
I would go hungry for a couple days in college because I would reason, its not a need, I won’t die if I dont eat today. This created some unhealthy mindsets.
Anyway, 2008 financial crash pretty much changed my relationship with money. I had sacrificed so much of my youth by that point. At 27 I owned 2 houses and a plot of waterfront land. I had been buying silver as it ran up to a record 50 dollars at that time. I had just about hit my first million. In a couple days, silver went from 50 to like 16 bucks and my two houses dropped 50% in value. All that life sacrifice, vanished in thin air. I thought about all the experiences or things I could have bought with evaporated wealth.
It was at that point I realized 2 things. 1. I could understand why people jumped out of windows during the 1920’s stock market crash and 2. I needed to stop putting my life on hold just to save money. It’s funny, because I had been reading mr.money mustache heavily because he validated my scarcity mindset. Then, my wife turned me on to two things that changed my life, the book, your money or your life, and financial samurai. Sam talked about money as a way to live a better life, he talked about FAT fire and those those two things together finally changed my behavior with money. It still sometimes feels painful to pull out my wallet, but now I ask, will this make mine or my family’s life better instead of is this a want or a need.