6 Questions to Ask Yourself Before Making a Financial Stretch
6 Questions to Ask Yourself Before Making a Financial Stretch
Most of us have read enough money books or listened to enough podcasts to understand that there are general guidelines and parameters recommended for how much of our income to allocate to things like housing costs, general savings, retirement savings, etc. But an important question that often gets far less attention is, how do you know if it’s okay to break those rules? When is it okay to take on a financial stretch to purchase a first home (or next home), to send yourself or your kids to college, or to leave your job and find a new one or start a business?
The reason there are very few popular financial gurus willing to give this advice may be because they are simply all in dramatic opposition to financially stretching yourself, but I suspect it’s more a matter of it being hard to give generic advice related to when and how to decide if a financial stretch is a risk worth taking. Because the reality of many successful financial stories is that they often started with financial stretches that worked out well, and the reality of many failed financial stories is that they often started with financial stretches that worked out poorly.
So, how can you decide if a financial risk is worth stretching for?
The answer is, of course, that there’s no way to be 100% certain. What makes a financial stretch a risk is the uncertainty of its outcome (as well as the uncertainty of other financial outcomes, like the overall economy, job security, etc. while you are in the stretch phase). But because not taking at least some financial risk can be, in and of itself, risky to one’s financial future, it makes sense to talk about guidelines you can use to help you decide if a stretch is worth making and if you are well prepared to make it. If honestly answered, spending time on these questions can increase the likelihood that you make informed stretch decisions that have a higher probability of coming out in your favor.

What Are Your Motivations for Making This Stretch?
There are several reasons that people are tempted to stretch financially, but many of these are not good reasons to push your budget or your savings to the edges of what it can sustain.
For example, some common, but terrible reasons to stretch financially are:
- Wanting to buy or have something to impress other people or obtain status.
- Wanting to buy something that is nicer or more luxurious than you can afford, but isn’t actually a long-term investment related to your core values.
- Thinking or believing that an investment (or a job change) is a good way to beat the system or get rich quickly.
- Trying to bail someone else (like your parents or adult children) out of a financial jam.
Keep in mind, this is not saying that these aren’t things you can’t or shouldn’t be doing with your money if you can do them within the parameters of maintaining a sound debt to income ratio, strong retirement savings, and a healthy emergency fund. If you have enough to do that and spend your money on luxury items or bailing your kids out of financial jams, that’s at your discretion to do. But the reasons above are bad reasons to take your otherwise sound budget and financial situation and stretch it to a potential breaking point.
On the other hand, reasons that might be worth stretching financially are:
- Making a long-term investment in something like housing IF homeownership is a core, long term financial goal. Particularly if even a basic housing purchase where you live will require a financial stretch.
- Changing to a job that is more sustainable from a health or mental health perspective even if it means making less money.
- Obtaining education or certifications that will allow you to pursue a new or different career path (either for quality of life or for higher pay).
These are by no means comprehensive lists of the wrong and right motivations to stretch financially, but the key point is that a financial stretch will almost always result in short to medium term financial discomfort, which will be incredibly difficult to sustain if you’re in it for the wrong reasons.

Are You Being Honest About Your Motivations?

I always recommend that folks bounce their proposed financial stretches off trusted advice givers because when evaluating the rationale behind a stretch, it can be easy to look for confirmation bias and see the reasons we have as being reflective of the second list above, when in fact, they are much more representative of the first list.
For example, convincing yourself that you need to stretch on a car or home purchase when there are less expensive options available that meet your basic housing or vehicle needs falls into the category of “wanting to buy something nicer or more luxurious than you can actually afford,” not into the category of “making a long-term investment in something like housing.”
The same can be said for pursuing a much more expensive education than is needed to make the career change you want.
So, engage the help of trusted advice givers (not just the people who always affirm your choices) to help you really sort out your motivations for the stretch, and if they are sound, move on to questions 3-6.

How Much Discomfort Are You Willing to Live Through and for How Long?
By definition, a financial stretch is likely to make you feel…stretched. That means somewhere else in your discretionary budget*, you’re going to be spending less than you do now.
You need to be clear about exactly which of those expenses you will be reducing, and by how much, to meet the financial stretch you’re about to make. But you also need to be clear about how long you will potentially need to make these sacrifices.
For example, a dual-income family where one partner is headed back to school may be looking at 2-4 years of living off a single income while in school, but they should also be factoring in how many more years of single-income living might be needed if it’s hard to find a job right out of school, or if they’ve taken on student loan debt and really need to use that second income to pay off the debt for a few years after college. The reality is, this family may think they’re forgoing eating out, cable TV, and vacations for 2-4 years, but when looking closely at the situation and all its related parts, they may need to be committed to living without these things for more like 7-10 years, depending on how the variables play out.
Similarly – with a home purchase that’s a financial stretch, often, after some time passes, wages increase, or interest rates decrease, allowing for the cost of housing to stay fixed or go down while income keeps increasing. It’s true that for many homeowners, what once felt like a BIG stretch will, someday, not feel like much of a stretch at all. But whether that day comes in 2 years or 10 years is dependent on a lot of factors that are often outside of the homeowner’s control (like interest rates, the housing market itself, and future wage increases).
Before heading into a financial stretch, make sure you’re committed to how long it might require you to stretch for, and try to avoid the temptation of imagining everything will work out just right so that the stretch won’t last too long.
*If you’re envisioning making the stretch by cutting things like how much you’re saving for retirement or emergencies, and you haven’t absolutely gutted your discretionary spending to make a financial stretch, that’s probably a good indication that you’re not quite ready for the commitment the stretch requires. It’s not that a stretch can’t involve some short-term adjustment in long-term savings, BUT that adjustment should come only after every single ounce of discretionary spending has been cut.

What is The Worst-Case Scenario if This Stretch Doesn’t Work Out and How Do You Feel About the Risk?
Above, we encouraged you to think about how long it might realistically take before you feel less stretched, but the reality of the financial stretch is, it’s a risk, and there’s a chance it just simply won’t work out at all. So, it’s important to identify the worst-case scenario, and make sure you are okay with that as a potential outcome.
For example, starting a business that requires you to take on $150,000 in loans has a worst-case scenario that you may need to declare bankruptcy on that debt. If that’s not a worst-case scenario you can live with, it’s likely too big of a financial stretch for you to take on. But starting a business with the money you have in savings and not taking on debt, only has a worst-case scenario of potentially losing what you’ve put into it, and needing to go find a job again.
It’s important to note that neither of these outcomes makes a risk worth or not worth taking. We all have different appetites for risk and different comfort levels with what we’re willing to accept as our worst-case scenarios. But before any financial stretch, you need to look the worst-case scenario in the eye and say, “am I okay with this outcome?”
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Am I okay with drawing my savings down to $0, knowing that I might have to build it back up from scratch again?
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Am I okay with the bank foreclosing on this house if I cannot make the payments and the market drops, so I cannot sell it for at least what I owe on it?
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Am I okay with having to pay back $75,000 in student loan debt for a career I thought I would want to do, but realized that I didn’t like at all once I got into it?
Financial stretches can be extremely rewarding, but we all tend to imagine only the potential rewards when we take them on. It’s easy to get caught up in the excitement of the dream and forget that a financial stretch is, by nature, also risky. How much you’re willing to risk depends a lot on your personal financial situation and tolerance for risk, but the key point is that you need to be willing to take an honest look at what you have to lose BEFORE you make a big financial commitment that stretches your budget, and then decide whether you can tolerate that much loss.

Avoiding the Worst-Case Scenarios – Does Your Backup Plan Have Backup Plans AND Outline WHEN to Use Them?
One of the most predictable ways to ensure the success of a financial stretch is to give it the time it needs to be successful. Businesses that are slow in the first few years often take huge leaps in revenue after they’ve been around for four or five years. Houses that might be over-mortgaged and under water two years after purchase, will most likely, in ten years, look like a good investment.
The more plans and backup plans a financial stretch has, the more likely it is to succeed, simply by virtue of it having enough time to succeed. You’re far less likely to end up giving up on a stretch before it has time to bear fruit if you create these plans in advance and know when you’re going to deploy them.
For example – let’s say you have $100,000 in savings, and plan to start a small business that has $30,000 in startup costs. You also plan that the business will take 18 months to get up and running and making money, so you’re planning to use another $60,000 of your savings to cover your living expenses for 18 months. You’ve run your budget, and you know that this is a manageable expectation for living costs, and it will still leave you with $10,000 in savings.
That’s your plan.
But it’s based on the assumption that you are going to be making enough money to completely support yourself within 18 months. What if you aren’t able to do that? Will you walk away from the business and go back to work (that is an option, and possibly a good one if the business has simply proven to not be a workable idea).
But what if the business is doing well, just not as well, or as fast as you had hoped it would? What are your backup plans that allow you to stay out of financial trouble, but still in business?
- Could you do part-time work outside of business hours? Does it make sense to start this after 6 or 12 months if you haven’t met your target revenue goals, so that you can stretch your remaining savings farther and give the business more time to get off the ground?
- What have you obstinately held onto in your budget that you might finally be willing to cut if what you needed was just a little more time, and at what point are you planning to make those cuts?
People are often forced into a situation where they’ve already gotten in financially too deep for a backup plan to help when they don’t have multiple layers of backup plans and/or don’t know when to deploy said plans.
If you decide to look for part-time work while there’s still money left in savings, then the work you need to buy your business more time can still be supplemented by what you have left in savings. If you wait until you’re out of funds, you may need to go back to work full time to keep yourself financially afloat.
If you decide to rent out a room in your house the very first month that you can’t make your mortgage payment, your backup plan may buy you enough time to right the ship without getting into any real financial trouble. But if you wait until you’ve taken out a second mortgage or taken on a lot of credit card debt before you consider this option, it’s fairly likely that it won’t be enough to keep you afloat.
You should have your backup plans in place BEFORE you commit to the stretch, as well as clear indicators of when you plan to deploy them to keep you out of real financial trouble. This will buy you what is, perhaps the most underappreciated resource of a successful financial stretch – time…
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Time for the idea to work.
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Time for the investment to grow.
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Time before you must decide whether the stretch was a success or a failure – the best choice you ever made, or the worst one.

What’s Your Track Record with Budgeting, Savings, Short-Term Sacrifice, and Other Financial Stretches You’ve Made?
This is, perhaps, the reason that no one wants to give generic advice about financial stretches. It’s true that there are a ton of variables that are out of your control that will factor into whether your financial stretch goes down as one of the best or one of the worst decisions you’ve ever made, but you are the X factor in that equation that’s hard for an outsider to account for. And it’s worth it to take a close look at your history with the financial stretches you’ve previously made.
Are you prone to getting in over your head, thinking things would go well, and then ending up with a financial hole to crawl out of when they didn’t go as planned?
Or, conversely, do you have a history of willingness to make big sacrifices in spending, or take on second jobs or roommates to see your financial stretches through so that you stay out of long-term financial trouble?
Anyone who tells you, based on their experience, that it’s worth it to make a financial stretch like buying a house because it was a great decision for them, is giving you a very anecdotal piece of advice, one that may be lacking a lot of details, like how they said “no” to all of their friends’ invitations for 10 years if they required a hotel room or a plane ticket purchase, or how 3 packages of ramen was their $1 a day meal plan for 5 years. These were sacrifices they were willing to make for something that was important to them, but they may not be sacrifices you are willing to make. And if it’s not a sacrifice you are willing to make, what was a great decision for them might turn out to be a catastrophic decision for you.
Look at your history and you will find examples of financial stretches in the past that you’ve taken, even if you didn’t give them much thought at the time (don’t forget, financial stretches can be small – they don’t just have to be big things). How do you feel about them a year or 10 years later?
Does that guitar you stretched to afford feel like the best decision you ever made, or is it sitting in your closet, not having been played for years, a relic of something that was more a dream than a commitment?
Was the car payment you took on something that you were enthusiastic about making, even after 2 years because the car added that much value to your life, or did you quickly come to resent it and wish you hadn’t committed to something quite so expensive?
Have you historically been willing to do whatever it takes (multiple jobs, roommates, etc.) to get through financially stretched times, or have these often resulted in the accumulation of credit card debt or missed bills?
You are the most important human to study when you’re trying to decide if you should make a big financial stretch. Asking Reddit if it’s worth it to buy a house that stretches your budget is far less valuable than asking yourself, “how have I done with budget stretches in the past? And what is MY track record with staying on a tight budget even when it means saying no to things I want to do?” If the answer is, “not great,” then it’s worth it to pause on the big stretch you’re considering.
At the end of the day, the thing that is entirely in your control is not just how well you make your plans and backup plans, but how well you stick to them. And if you haven’t gotten yourself to a point where you can reliably meet tight budgeting goals, you’ll likely want to practice and strengthen that skill first, before you take on a big financial stretch.
Making a Financial Stretch Work for You

There’s no proven formula upon which to decide if a financial stretch is worth taking. We’re asking you to pause and reflect a lot here – examine your true motivations, think about your values and how much you’re willing to sacrifice in the quest to reach a financial goal that might be life changing (for better or worse), and take an honest look at your own track record.
Spending time on worst-case scenarios, how it will feel to be in those scenarios, and coming up with Plans A through Z to address them will not only give you a better chance of financial success – it will also put you in the driver’s seat, giving you a sense of agency when things inevitably don’t go exactly as planned.
The greater the stretch, the greater the risk, and the more preparation you need to tackle it. Skydivers don’t jump out of airplanes solo before they jump tandem, and when they do jump solo, they do it with a parachute, a backup parachute, and an automatic activation device. Jumping out of an airplane is an inherently risky thing to do, but so is a big financial stretch. Think of answering these 6 prompts as your financial safety gear as you decide whether or not to embark on a financial stretch so that if and when you decide to jump, you can increase your odds of making it to the ground safely.
Image attribution: Photos by Kelly Sikkema on Unsplash, Milan Popovic on Unsplash, Marcos Paulo Prado on Unsplash




































