How to manage paying expenses when moving to a weekly pay schedule and with a pay increase?
This is really just a matter of planning.  It's good that you don't want the train to go off the rails but really you just need to budget your fixed expenses.  I do this by having two checking accounts.  One account gets a direct deposit to cover all of my fixed expenses, the other is my regular checking account.   Take your rent and other fixed expenses, if you have any, and total them.  Take that total and divide by four.  That's how much of each check you should be socking away in to the separate account. Additionally, with a 30% pay increase you can probably start a savings account.  You should start to establish an emergency fund so this really never becomes a problem.  Take 10% of your pay and put it in savings, this will still leave you with a healthy pay increase to enjoy but you'll keep some of your money for yourself too. "Its really, really good of you to admit your short comings with a desire to improve them.  It takes courage.  Keep in mind that most of us that answer questions here are really ""good at money"" so we have a hard time relating.  Would you want people that are bad with money answering questions on a personal finance site?   While it is intimidating you will need a budget.  A budget is simply a plan for how to spend your money.  Your budget, based on your new pay frequency, will likely also need some cash flow planning as a single paycheck is unlikely to cover your largest expenses.  For example your rent/mortgage might be less than a single paycheck so you will have to save money from the previous paycheck to have enough money to pay it.   Your best bet is to have a friend or relative that is good with money help you setup a budget.  Do you have one?  If not you might inquire about a church or organization that offers Financial Peace University.  The teachers of the class often help people setup a budget and might be willing to do so for you.  You could also take the class which will improve your money management skills.  For $100 you'll have a lifetime pass to the class.  If it helps you avoid three late charges/bounce checks then the class is well worth it. Now as far as spending too much money.  I would recommend cash, but you have to do it the right way.  Here is the process that you have to follow to be successful with cash: Doing cash will give you a more concrete example of what spending means.  It won't work if you continue to hit the ATM ""for just $20 more"".  It will take you a bit to get used to it, but you will be surprised how quickly you improve at managing money." Unlike other responses, I am also not good with money.  Actually, I understand personal finance well, but I'm not good at executing my financial life responsibly.  Part is avoiding tough news, part is laziness. There are tools that can help you be better with your money.  In the past, I used YNAB (You Need a Budget).  (I'm not affiliated, and I'm not saying this product is better than others for OP.)  Whether you use their software or not, their strategy works if you stick with it.  Each time you get paid, allocate every dollar to categories where your budget tells you they need to be, prioritizing expenses, then bills, then debt reduction, then wealth building.  As you spend money, mark it against those categories.  Reconcile them as you spend the money.  If you go over in one category (eating out for example), you have to take from another (entertainment).  There's no penalties for going over, but you have to take from another category to cover it.  So the trick to all of it is being honest with yourself, sticking to it, recording all expenditures, and keeping priorities straight.   I used it for three months.  Like many others, I saved enough the first month to pay the cost of the software.  I don't remember why I stopped using it, but I wish I had not.  I will start again soon.
There's no reason why you couldn't have your work withhold the money for you, but you have to keep a close eye on it an file paperwork causing extra work for yourself and the payroll department. You also have that money withheld weekly instead of keeping access to the money until the end of the quarter if you paid directly to the treasury. "My answer has nothing to do with tax brackets or mathematics (I'm taking advantage of the leeway your question allowed), but rather it has to do with career goals and promotion.  Large companies often have large ""Policies & Procedures"" booklets to go with them.  One policy that sometimes exists which would make it a bad idea to accept a raise is: Employee cannot be given more than one   salary increase in a 12-month period This means that if you accept a standard-of-living or merit increase of say, 2% or 3% in April, and then you apply for a job that would otherwise warrant a pay grade increase, you may be forced to wait until the following year to get bumped to the proper pay grade. Of course, this totally depends on the company, but it would be advisable to check your company's H.R. policy on that, if you're considering a move (even a lateral one) in the future." "I'd forget raises, as they're hard to predict. Figure in cost of living adjustment to keep pace with inflation, and recalculate if you get a raise. I don't think about it too hard. After I deposit my expected monthly expenditures in my checking account, the balance goes to savings, so any raises will go to savings unless I specifically alter my direct deposit settings. I have to make a conscious decision to inflate my lifestyle if I want to spend that money. Also, realize that ""matching your income"" is a bit overkill. Right now, part of that income is going to savings. If you spend 60% of your income now, why would you suddenly need the extra 40% when you retire?" I do something pretty simple when figuring 1099 income.  I keep track of my income and deductible expenses on a spreadsheet.  Then I do total income - total expenses * .25. I keep that amount in a savings account ready to pay taxes.   Given that your estimates for the quarterly payments are low then expected, that amount should be more then enough to fully fund those payments.   If you are correct, and they are low, then really what does it matter?  You will have the money, in the bank, to pay what you actually owe to the IRS. You just need to average out the weekly hours and income over the year. So if his yearly income is $100,000 p.a. then this would average out to $2000 per week of which 15% would be $300 per week. It does not have to be exactly 15% per week as long as over the long run your saving your target 15%. If he gets a pay rise you can include this in the saving plan. Say he gets a 5% increase in pay you would increase the $300 per week by 5% to $315 per week. "To address the issue in the title of your question: Many expenses strike at what for all practical purposes are random intervals. Roof starts leaking, car needs repair, etc, don't have a fixed cost every month. Medical expenses can certainly be more extreme than many other expenses, but their nature is the same. And so the way to budget for them is the same: You figure out what your average expenses are over a long period of time. Then you start putting away a little more than this amount every month. Keep putting away until you have a reserve larger than any expense you are likely to get hit with all at once.  I have no idea what your particular expenses are, so let me use myself for an example. My medical bills last year were unusually large: about $6,000. I have lousy insurance and a couple of chronic conditions, so my bills are usually maybe $1,000 to $2,000 per year. So I plan on about $150 per month for medical bills. Most insurance policies have an ""out of pocket maximum"". This should be the most you'd ever have to lay out in a year. Mine is $13,000. (I told  you my insurance sucks.) So I have an account that I have now built up to $13,000. Worst case, I wipe out that account. In any case, if my bills are that large, the doctors or hospital will normally agree to a payment plan. (I still owe a few hundred on my bills from last year and the hospital is letting me pay it off at $120 per month.) Your question brings up a lot of issues about difficulties of working with insurance and the U.S. medical system in general. I'm not sure if your intent was to get advice on the rest of it all. Simple -- not pleasant, but simple -- answer: If you're insurance is provided by your employer, you're pretty much stuck with the policy that the employer negotiates. I don't know how much you're contributing to premiums, usually the company pays the bulk of it. You could investigate getting a policy on your own, but odds are that any policy you could get for what you're contributing now would be way worse than what you can get through the company. You could always investigate, but I doubt you'll do better. You can talk to HR. If it's a big company, they may have some muscle with the insurance company and could help you out. Failing that, it becomes a political question of how the laws affecting medical care and insurance in the U.S. are set up, and while I have many ideas for how it could be improved, sadly I'm not in a position to do much about it, and I doubt you are either. Unless you have the resources to run for president." Honing in on your last question: Is there a better way?  I think there is, but it would require you to change the way you handle your spending, and that may not be of interest to you.  Right now you have a lot of manual work, keeping track of expenditures and then entering the, every day. The great thing about switching to a habit where you pay for everything using a debit or credit card is that you can skip the manual entry by importing your transactions from your bank. You mention that your bank doesn't allow for exporting. There's still a chance that your bank can connect with a solution like Wave Accounting (http://www.waveaccouting.com), which is free and made for small business accounting. (Full disclosure: I represent Wave.) If your current bank doesn't permit export or connections with Wave, it may be worth switching to a different bank. It's a bit of a pain to make the switch, I know, but you really will save a massive amount of time and effort over the course of the year, as well as minimize the risk of human error, compared to entering your receipts on a daily basis. In Wave, you can still enter all of your cash receipts manually if you want to continue with your current practice of cash payments. One important thing to mention, too: If you're looking for a better way of doing things, make sure it includes proper backup. There would be nothing worse than entering all that data onto a spreadsheet and then something happening to your computer and you lose it all.  Wave Accounting is backed up hourly and uses bank-level security to keep your information safe. One last thing: as I mention above, Wave Accounting is free.  So if it is a good match for your small business accounting needs, it will also be a nice fit for your wallet. This is the same as any case where income is variable.  How do you deal with the months where expected cash flows are lower than projected? When I got married, my wife was in the habit of allocating money to be spent in the current month from income accrued during the previous month.  This is slightly complicated because we account for taxes (and benefit expenses) withheld in the current months' paychecks as current expenses, but we allocate the gross income from that check to the following month for spending. The benefit of spending only money made during the previous month is that income shocks are less shocking.  I was working for a start-up and they missed payroll that normally arrived on the first of the month.  Most of my co-workers were calling the bank in a panic to avoid over-draft fees with their mortgage payments, but my mortgage payment was already covered.  Similarly, when the same start-up had a reduction in force on the first day of a new quarter, I didn't have to pull any money from savings during the 3 weeks I was unemployed. In the end, you're going to have to allocate money to the budget based on the actual income--which is lower than your expectations.  What part of the budget should fairly be reduced is a question you and your wife will have to figure out. You need to know loans are not free; and they are not a way to solve budget issues. If you are having problems with making your income last over your expenses, you do not need to add another expense (in the form of a loan) What you really need to do is create a budget, track and understand your expenses, and then decide if you should focus on raising  your net income level or cutting down expenses. Keep up with your budget.  You can reduce the frequency, but you need to track your spending really for the rest of you life.  It is just a good habit, like personal hygiene. Once you understand your money (via your budget), you can start to save money into an emergency fund that will cover you during the times of zig zags. I say it very plainly as if it is super easy; but it requires will power and the foresight to understand that if you don't manage your money, nobody else will.  Being sane with your money is one of the most important things you can do now to improve your future. IMPROVEMENT NathanL has an excellent first step with budgeting:  Allocate money to be spent for the next month from money made during   the previous month. This will build a cushion into your budget and   alleviate the fear that the OP mentioned "Entire books have been written on how to get to the end of the month before you get to the end of the money. It's a very broad problem. But in your case, let me point out that your salary never ""suddenly disappears"" (unless you're paid in cash and it blew away or was stolen while you were sleeping.) You spent it.  For a month, monitor your spending. One approach is to write everything down in a small notebook. Come up with categories like ""Rent"", ""Food"", ""Transportation"" and look at the totals. Over time, you can estimate what you spend in a normal week or month on these things. When you spend much more, you can ask yourself why. It might be because you just splurged money you didn't have on something you didn't need. It might be because something broke, and you hadn't been saving a small reserve month after month to pay for those repairs when they would be needed. It might be because some bills only come once a year or every 6 months, and you hadn't been saving a small reserve to pay that bill when it came in.  Once you understand where your money is going and why it sometimes runs out, you can work out what to do about that. It might involve spending less. But that's not the first step. The first step is not to be surprised by ""sudden disappearances"" that are anything but." "You have to be firm. Refuse to work excessive overtime. This is why I switched to consulting. 16 hour days suck, but if you're billing for 16 hours, it makes it more bearable.   I've recently switched to the ""I only care about money"" mode of thinking, and switched to hourly pay after being salaried for almost 10 years. And it's not that it's the only thing that matters, but a lot of the rest of this stuff falls into place. It really simplifies things. You don't work for free. Your time is seen as a commodity. You are given goals and targets. You're not dragged into unnecessary meetings. Your opinion is respected. If you have to work saturday, you're sure as hell billing for it. If I take off at 2pm because I want to watch a hockey game, I just stop billing at 2 and there isn't this ""I'm not getting my money's worth!"" feeling from the manager." "I currently use Mint for this, which I see that you have already disqualified but not why you have disqualified it.  Set ""budgets"" for how much you want to spend on what type of expense, and then be sure to assign expenses to a budget as they come in. Mint actually learns what expenses go to each budget and eventually does it automatically." There are several reports under the Reports>Income & Expenses menu which could be useful. Cash Flow - shows, for a particular set of accounts, where incoming and outgoing money from those accounts came from and went to. Expense BarChart/PieChart - shows top N expenses. Income Statement (also called Profit & Loss) - shows all incomes and expenses for the time period. Each of these reports have an options dialog which will let you change the period that they are reporting on and the accounts to be included in the reports. The Cash Flow report sounds particularly useful for your second scenario. I think you might benefit from adopting a zero-sum budget, in which you plan where each dollar will be spent ahead of time, rather than simply track spending or worry about the next expense. Here's a pretty good article on the subject: How and Why to Use a Zero-Sum Budget. This is the philosophy behind a popular budgeting tool You Need a Budget, I am not advocating the tool, but I am a fan of the idea that a budget is less about tracking spending and more about planning spending. That said, to answer your specific question, one method for tracking your min-needed for upcoming expenses would be to record the date, expense, amount due, and amount paid as shown here:  Then the formula to calculate the min-needed (entered in E1 and copied down) would be: As you populate amounts paid, the MinNeeded is adjusted for all subsequent rows. You could get fancier and only populate the MinNeeded field on dates where an expense is due using IF(). Just set up a budget. Indicate how much money comes in, how much goes out to must pay expenses (lodging, food, gas, heat, cooling, etc), and determine how much is leftover for anything else you want. If that amount is ok, then you're fine. If not, something needs adjusting.