Situations, answered straight
Not advice, and not a lecture on budgeting. What the decision actually turns on, what the number really is, and what order things go in.
What should I do with an inherited house if I still have credit card debt?
The house feels like the decision.
Working nights, and wondering whether selling would end itCan I stop working nights if I sell my house?
Often yes, and by a bigger margin than people expect, because the number you have to replace is smaller than the one you earn.
A lump of money, a loan, and no obvious right answerShould I pay off my truck or invest the money?
Most people compare the two rates and stop there.
Money in, money out, nothing spareI have nothing left at the end of the month. Where do I even start?
You probably don’t have a spending problem.
Starting late, with less time than the advice assumesI am in my fifties with no retirement savings. Is it too late?
No, but the lever changes.
Equity on one side, expensive debt on the otherShould I sell my house to pay off debt?
The debt disappearing isn’t the test.
Stuck in work you want out ofI want to leave my job but can’t afford to. What actually has to change?
Usually one number, not your whole situation.
A one-off amount, and a lot of opinions about itI am about to get a lump sum. What should I do with it first?
Do nothing with it for a few weeks.
Space you already have, and whether it changes anythingIs renting out a room actually worth it?
The money is usually real, so that isn’t the question.
A job, and no fixed addressI am working but I have nowhere stable to live. How do I get out of this?
The wall is usually the deposit, not the rent.
No crisis, no direction, and everyone else seems further alongI am in my twenties and feel behind everyone. Am I?
Probably not, and the feeling usually comes from comparing against a highlight reel rather than a number.
Severance in hand, and no plan yetI have just been laid off. What should I do first?
Work out how many months of what has to go out you can cover, before deciding anything else.
One household became two, on the same incomeWe have separated and the money doesn’t work any more. Where do I start?
Work out what one household costs you now, on your own, before agreeing anything.
Behind on rent, or the notice has arrivedI think I am about to lose my housing. What can I actually do?
Talk to the landlord before the arrears grow, and find out what the actual timeline is where you live.
Turning over well, and nothing left at the end of itMy business makes money but I never seem to. What’s actually wrong?
Almost nobody in this position has a sales problem.
Two incomes, and nothing left at the end of the monthWe earn good money and have nothing to show for it. How?
This is almost never overspending in the way people mean it.
In the US, where coverage usually comes with the jobI lost my job. What happens to my health insurance?
You have three routes and a deadline.
In the US, when the retirement money looks like the only cushionShould I cash out my 401(k) after losing my job?
Usually not first.
In the US, where each state runs its own programHow do I file for unemployment, and what should I expect?
File with your state’s unemployment office in the first week, online if you can: benefits are based on when you file, and delays cost you weeks at…
In the US, when the bill arrives after the careI have medical bills I can’t pay. What do I do first?
Don’t pay it on a credit card, and don’t ignore it.
More than one balance, and every payment feels like it disappearsI have debt on several credit cards. Which do I pay first?
Pay the minimum on every card, then put everything extra on the one with the highest interest rate, that saves the most money.
Several debts, and one loan promising to make it simpleShould I consolidate my debt, or just pay it off myself?
Consolidation helps in one situation: when the new rate is genuinely lower, the fees are smaller than the interest you save, and the old cards stay…
When paying it back in full no longer looks possibleDebt settlement or bankruptcy, which is right for me?
Before either, find out whether a formal repayment plan through a nonprofit credit counsellor would work.
A missed payment, and the car is how you get to workI’m behind on my car payments. What do I do?
Call the lender before the next payment is due, not after.
Rent eats everything, and somewhere else looks easierShould I move somewhere cheaper to get ahead?
It works when the move lowers what goes out by more than it lowers what comes in.
Rent is the biggest bill, and home is an optionShould I move back in with my parents to save money?
It can be one of the fastest ways to get ahead, if it has an end date and a target.
Twenty years in, and the work no longer fitsIs it too late to change careers at 40?
No, but the money has to be planned, because the change usually comes with a pay dip before it recovers.
Less work, if the numbers allow itCan I afford to go part-time?
Work it out on what you would actually take home, not your hourly rate.
Exhausted, and the bills still comeI’m burned out but I can’t afford to stop working. What do I do?
Start by finding out what rest you can get without losing income: sick leave, unused holiday, a short leave or reduced hours.
Behind where you thought you would beI’m 40 with nothing saved. How do I start over?
Begin with the month, not the decades.
More house than you need, and less money than you wantShould we downsize our house to free up money?
Downsizing works when the smaller home costs clearly less each month and the move releases money you have a plan for.
An idea that will not go away, and a paycheque that pays the billsShould I quit my job to start a business?
Usually not first.
Evenings and weekends, and a job that still needs youHow do I start a business while working full-time?
Pick the smallest version that can earn money, give it fixed hours each week, and protect the job while you build it.
It pays the bills, and it has everything else tooMy business is taking over my life. What do I do?
Decide what you want the business to give your life, a certain income, certain hours, time with the people you love, and then judge every change…
Years of work, and you are not sure it is worth it any moreShould I close my business?
Look at three things honestly: whether it pays you a fair income for the hours, whether it can with changes you are willing to make, and what you…
When every day looks the same and nothing seems to moveI feel stuck in life. Where do I even start?
Start by writing down what you want an ordinary day to look like a year from now, then the one thing standing most in the way of it.
The paycheque keeps you there, and so does everything it pays forI am stuck in a job I hate, but I have bills to pay. What do I do?
Work out the number your life actually needs each month, not your current salary.
A clear order millions have followed, and when a different one fitsDave Ramsey’s Baby Steps: do they fit my situation?
The Baby Steps give a simple order: a $1,000 starter emergency fund, then all debt except the house using the debt snowball, then three to six months…
Every choice seems to come back to what you can affordI feel trapped by money. How do I get out?
Find the one money fact that is doing the trapping.
Waiting for the right time, the right money or the right momentMy life feels on hold. How do I get it moving again?
Name what you are waiting for, then decide whether it is something you can make happen or something you are only hoping for.
Not goals on a list, but an order you can followHow do I make a plan to change my life?
Start with the life you want, described as an ordinary day.
The decade where the choices you made start to feel permanentI feel stuck in my 30s. Is that normal, and what do I do?
It is very common.
Halfway through a working life and wondering about the second halfI feel stuck in my 40s. Where do I go from here?
Start by deciding what you want the next twenty years to look like, then check whether your current path gets you there.
Two ways to pay off several debts, and how to chooseDebt snowball or avalanche: which should I use?
The avalanche pays the highest interest rate first and usually costs less in total.
Two jobs keep the bills paid and take every eveningI work two jobs and never see my kids. How do I change that?
Work out exactly what the second job pays for.
The work keeps growing and home keeps getting less of youI work too much and miss my family. What can I do?
Start by finding out how many of your hours the money truly needs.
Wanting your time back without the month falling apartHow can I work less and still pay the bills?
Lower the amount that has to go out each month, then raise what each hour of work pays.
Hours every day spent getting to and from workMy commute is eating my life. Is it worth changing?
Often yes.
Wanting more income without giving up more eveningsHow can I make extra money without taking a second job?
Start with what you already have: your current job, your skills, and things you own.
You think you have earned more, and the conversation feels impossibleHow do I ask for a raise when I am scared to?
Ask for a meeting about your pay, bring two or three plain facts about what you do and what the job pays elsewhere, and name a number.
Too many bills, not enough money, and no idea where to startI feel like I am drowning in bills. What do I do first?
Put every bill on one page: who it is to, how much, and when it is due.
Not enough money to pay everything this monthI am behind on bills. What should I pay first?
Pay in this order: housing, utilities, food, and what you need to keep working, like your car or phone.