How to Think Your Way Out of Any Business Problem (The Contrarian Approach That Actually Works)
I was sitting across from the founder of a Calgary soffit lighting company last month, watching him describe his frustration.
Great product. Solid team. Happy customers. Revenue growing steadily.
But something was missing. That repeatable sales engine every business needs to scale past the founder's personal network.
"We've been thinking about traditional marketing," he said. "Google ads, maybe some Facebook targeting. Go after the decision makers directly."
Made sense. Target the person who signs the checks, right?
Then I asked him one question that changed everything: "What would you do if you wanted to guarantee your sales strategy failed completely?"
Here's what I've learned after helping dozens of business owners break through revenue plateaus: the strategies that feel most logical are often the ones keeping you stuck.
Steven Bartlett calls it "leaning into absurdity" in Diary of a CEO. I call it reverse brainstorming. And it's become one of the most powerful creative problem solving techniques we use with our clients.
The premise is simple: instead of asking "How do we solve this problem?" you ask "How could we make this problem catastrophically worse?"
It might sound counterintuitive, but that's exactly why it works. Reverse brainstorming helps uncover blind spots and innovative ideas by flipping the problem upside down.
Back to my client. When I asked how he could guarantee sales failure, his answer came immediately:
"Ignore the partner who makes the emotional decision. Or worse, piss them off."
Then the follow-up: "What do your competitors do to reach those emotional decision makers?"
Long pause. "Nothing. They don't even try."
Suddenly, everything shifted. Instead of fighting for attention in the same crowded space as everyone else, he saw a completely open lane.
His target customers? Established couples with high disposable income. The financial gatekeeper says yes or no. But the other partner? They're the one who wants it. They're imagining how it'll look. They're excited about the transformation.
Every other company in his space was ignoring half the decision-making equation.
Now he has a sales strategy that no one else in his market is using, one that actually makes sense for how his customers really make decisions.
All because we started by generating negative ideas, a cornerstone of the reverse brainstorming process.
Traditional brainstorming fails because your brain automatically filters "bad" ideas. You're trying to be smart, professional, reasonable.
But reasonable thinking is exactly what got you stuck in the first place.
Reverse brainstorming shuts off those filters. When the goal is to make the problem worse, you stop worrying about looking stupid. You get honest about what's actually happening in your business. And you uncover truths that were hiding in plain sight.
Most brainstorming sessions dance around the emotional stuff. But emotion drives everything - especially the mistakes we keep making. When you reverse the problem, you allow the unsaid to surface. Suddenly, someone says, "Honestly, I hate that part of our business," and now you can find real solutions.
Here's what really happens in those moments:
Permission to tell the truth. When you're "trying to fail," it's safe to admit the stuff you've been avoiding. Like how your onboarding process confuses people. Or how your team avoids difficult conversations.
Pattern recognition. When you list as many negative ideas as possible to sabotage your business, patterns emerge. Usually, you're already doing some of these things - just subtly.
Contrarian thinking. Once you see what everyone else is doing wrong (including you), the path forward becomes obvious. Reverse brainstorming works by illuminating what you're already tolerating.
As "just an accounting firm," I've always asked myself: how do we lean into absurdity?
The answer became our entire business model.
While every other firm in our industry focuses on deliverables, we focus on relationships. While they optimize for efficiency, we optimize for transformation. While they talk about compliance, we talk about dreams.
Is it absurd for an accounting firm to have a "Head of Happiness"? Maybe.
Is it working? Our clients are doubling revenue, adding franchise locations, and finally getting their lives back.
Sometimes absurd is exactly what you need to unlock creative ideas and achieve the desired outcome. We've applied reverse brainstorming in nearly every area of our business - and it keeps generating creative solutions we wouldn't have seen otherwise.
Get specific. Not "How do we grow?" but "How do we build a repeatable sales process that doesn't depend on me personally knowing everyone?"
"How could we guarantee our sales process fails completely?" Don't be polite. Be real. Start generating negative ideas - this is where creative thinking begins.
This only works if participants feel safe being honest. Some of your best insights will come from uncomfortable truths. This is a brainstorming method where collaboration and trust unlock new perspectives.
The goal isn't just to collect ideas. It's to identify underlying causes and potential risks. Which of these "failure strategies" are you actually implementing right now?
Now that you’ve generated potential challenges and identified what doesn’t work, create the reversed idea. Build effective solutions by flipping the worst ideas into real ones - the kind that generate innovative solutions and drive results.
Reverse brainstorming isn't just for big picture planning. Here are three everyday situations where I pull out this creative problem solving technique:
The Question: "How could we make our team dread coming to work?"
What You'll Hear: "Micromanage everything." "Ignore wins." "Hold meetings with no purpose."
The uncomfortable truth? You're probably already doing some of these things - just subtly. But once they're on the table, you can actually address them and implement feasible solutions.
The Question: "How do we make clients regret hiring us?"
What Comes Out: Late responses. Unclear pricing. Vague deliverables. Making them feel like just another number.
This opens the door to creating a better experience by focusing on positive ones - and solving the original problem. Many of our best client experience upgrades have come directly out of reverse brainstorming.
The Question: "How do we make sure this never gets done?"
What You Discover: Bottlenecks no one wants to admit. Team members avoiding difficult conversations. Unrealistic scopes everyone's been dancing around.
It gives everyone permission to reset without finger-pointing and to brainstorm ideas that move the project forward. We've used reverse brainstorming in stuck projects to generate creative solutions that stick.
Reverse brainstorming isn't magic. It works best when:
• You're genuinely stuck, not just looking for incremental improvements
• Your team trusts each other enough to be honest
• You're willing to act on what you discover
Don't use it when you already know what needs to happen but just haven't done it yet. This is a creative thinking tool for breakthroughs - not procrastination.
The most successful business owners I work with don't just use this technique once. They make contrarian thinking a habit.
They ask "What is everyone in my industry doing?" and then explore the opposite.
They look at their biggest competitors and identify their blind spots.
They regularly challenge their own assumptions by imagining how those assumptions could destroy their business.
This unusual approach gives them a deeper understanding of the real issues - and helps them find solutions others miss. The reverse brainstorming process becomes second nature.
Here's what I've noticed after using this approach with dozens of clients: the businesses that grow fastest aren't necessarily the ones with the best ideas.
They're the ones willing to question everything.
While their competitors are copying each other, they're finding the gaps. While others are optimizing what's always been done, they're reimagining what's possible.
That soffit lighting company? They're not just selling outdoor lighting anymore. They're selling the feeling of coming home to something beautiful. Their competitors are still talking about lumens and warranties.
Same product. Completely different game - thanks to a few key negative ideas we explored early on.
The next time you're stuck on a business problem - whether it's sales, operations, team dynamics, or growth strategy - flip the script.
Ask yourself: "How could I guarantee this gets worse?"
Pay attention to what comes up. And if it makes you a little uncomfortable? Even better. That's where the breakthroughs live.
After using this technique with dozens of business owners, I’ve seen the same patterns show up again and again:
Sound familiar? You're not alone.
Reverse brainstorming makes these patterns impossible to ignore. And once you see them, you can start doing the opposite... on purpose. It's one of the best ways I've found to generate negative ideas that lead directly to creative solutions.
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You might have heard these grim statistics before: more than 80% of all small businesses fail within 10 years, and more than 80% of those businesses fail due to cash flow issues. While some dispute the exact numbers, the underlying issue can't be. Cash flow is important. Period.
One would think that one of the most important business areas would be well understood. That isn't the case though. Cash flow is still one of the most ill-understood topics within the small business community. And forecasting cash flow? Even though it is just as important, it is even more misunderstood.
Jump to a section of this post:
In this post we will shine light on these misunderstandings, talking about what cash flow is, what cash flow forecasting is, the different types of cash flow forecasting there are, and how forecasting your cash flow can greatly benefit your small business whether you're a founder of a startup or a web3 company, or a professional that has ventured out on their own (say a veterinarian, dentist, chiropractor, optometrist or lawyer).
So, let's start with the basics: what is cash flow?
Cash flow is simply the movement of money in and out of your business. Money coming in is called inflow, while money going out is called outflow. Your business' cash flows can be positive (more cash inflows than outflows), negative (more cash outflows than inflows), or neutral (equal cash inflows and cash outflows).
The movement of money within, and through, any business is extremely important. At a basic level, every entrepreneur sets out to make money. So stripping everything down, each business' ability to generate positive cash flow, consistently over time, determines just how good that business is performing.
The more cash flow a business can make, the better it is doing.
Now, the above discussion on the importance of cash flow might seem overly simplified, and it is, but most small business owners don't have a great handle on this basic construct.
And there are two reasons for this:
Double entry accounting underpins all accounting as we know it. It requires that every financial transaction to be recorded in at least two different accounts. For example, when you make a sale, you would record this transaction both in your sales account on your income statement and your cash account on your balance sheet.
While this system provides greater accuracy and transparency around business finances, it also makes measuring cash flow more difficult. And that's because changes in cash can occur in two places: your income statement or your balance sheet.
Examples:
There are two basic methods of accounting: cash accounting and accrual accounting.
Cash accounting only records transactions when the actual cash changes hands. So if you make a sale and the customer pays later, you wouldn't record that transaction until you collect payment from the customer.
Accrual accounting records income and expenses as they are earned or incurred, regardless of when any actual cash is received or paid out. Using our same example, if you make a sale and the customer pays later, accrual accounting would record the sale right away and create an accounts receivable. It would then eliminate that receivable and increase your cash balance when you collected payment.
Accrual accounting is a double edged sword. It creates financial statements that are more accurate and reliable for various users, but also creates timing differences, estimates and other complexities that aren't necessarily well understood by business owners.
Examples:
The cash flow statement is the report that helps overcome the shortcomings that accrual accounting and double entry accounting processes make. This report ties the balance sheet and income statement together within your typical financial reporting. It measures all cash inflows, all cash outflows and eliminates any non-cash estimates that are also contained within your financials. And ultimately it reconciles all of this information to the cash balance contained within all of your bank accounts.
You can see two different forms of cash flow statements: those using the direct method and those using the indirect method.
Cash flow statements using the direct method are considered by some to be more accurate. This method reports all cash inflows and cash outflows from your business operations separately from any other inflows or outflows. This could include things like customer payments, vendor payments, interest income, dividends and other operational items.
The indirect method is a bit more simplified. It adjusts your net income for any timing differences between when you record accrual based items and when the actual cash is paid or received. This reconciles your net income to your actual cash. While this method isn't as detailed as the direct method, it's also not as susceptible to error.
Regardless of the method used, cash flow statements are a very important piece of your financial picture. As mentioned previously, they show how cash moves through your business. That said, cash flow statements are historical in nature. They show you what your business did, but not where your business is going. To see that kind of information, you will want to use a cash flow forecast.
A cash flow forecast is a projection of all of your future cash flows. It is a best guess, based on all available information, of what you expect to happen in the future. This includes things like expected:
A good cash flow forecast will show you:
This will give you a clear picture of where your business is heading, and how much cash you will have on hand at any point in time.
We touched on some of the high level benefits of cash flow forecasting in our Definitive Guide To Managerial Accounting For Small Businesses. Simply put, knowing the future net cash flow of your business, and your estimated cash balance at any point in time gives you a lot of power as a business owner. You will be able to:
By forecasting cash flow, you can see when your business might have a shortfall of cash. This allows you to take steps to avoid or mitigate the effects of a cash shortage, such as delaying expenditures, extending payments on accounts payable or shoring up working capital with short term debt.
Cash flow forecasting will give you a better understanding of how money moves within your business allowing you to more effectively manage your activities with operating cash. This can be particularly helpful if your business:
Knowing when and how you will get paid, and how and when you will make payments will make you a lot less reliant on debt and lines of credit.
A cash flow forecast will give you a better understanding of your business's financial health. This information can then be used to make better informed decisions about how to best use your resources.
Do you have enough cash to buy the equipment you need to grow and hit your sales targets? Can you afford to hire that stellar employee you interviewed? If you open a new location how will that impact your bank account in the short and long term?
Whether you have negative cash flow or a host of cash surpluses, thinking through exactly how you will progress your business, and knowing the effects of these decisions is an extremely helpful exercise. It will surely boost your confidence.
A cash flow forecast will help you track your progress towards your strategic business and financial goals. The information gleaned from the cash flow forecasting process itself can be used to adjust your budgets and your business plans, making these documents dynamic and more relevant as your operations change.
There are a number of different types of cash flow forecasts. Just like cash flow statements there are different methods you can use to create a cash flow forecast. And depending on your goals, the time frame you use in your cash flow projection should change.
Similar to its cash flow statement counterpart, a direct forecasting shows the exact cash inflows and outflows that result from your business' operations. This is the more straightforward approach to cash flow forecasting as it directly ties to all incoming cash receipts and outgoing cash payments.
Indirect forecasting does not start with your business' operational cash inflow and cash outflows. Rather, it begins with your company's net income figure. From there, non-cash items and changes in working capital are added back into or deducted from the bottom line to get to a net cash flow figure.
Indirect cash flow forecasting is more common associated with three way cash flow forecasting. This cash flow projection method forecasts your income statement, balance sheet and cash flow statement and ties them altogether. Hence the term three way forecasting.
Three way cash flow forecasting is sometimes viewed as the most robust way to cash flow forecast. It eliminates a lot of possibility for errors, especially when using a spreadsheet, and also presents bank ready financial statement projections that can be used for lending purposes. This method is typically a lot more customized however, can take a lot more time to create and maintain, and sometimes isn't as easily understood by entrepreneurs.
Long term cash flow projections are typically forecast from one year to five years out, with most going to three years in range. This type of cash flow forecast is most often associated with strategic planning and indirect/three way cash flow forecasts. These types of estimates are often used to:
A short term cash flow forecast is much more operational in nature. It can range from days to months in terms of time frame, and often does not go beyond a year. This type of forecast is much more granular in nature, and has much more accurate information in terms of timing. It is often updated quite frequently, as regular as weekly forecasts or daily, and is ultimately used to answer the question "do I have enough cash to do X?" in the near term.
The biggest difference between a short term and long term cash flow forecast is its use. Long term forecasts are more strategic, while short term forecasts are more operational.
The best analogy is a road trip using a map. A long term cash flow forecast determines exactly where you are going and loosely determines how you will get there. A short term cash flow forecast is used while you are driving to that destination, constantly shifting due to traffic, construction and road closures.
It is often a best practice to use both a long term strategic and a short term operational cash flow forecast.
An accurate cash flow forecast can be a game changer. Whether you're a professional, such as a veterinarian, dentist, chiropractor, optometrist or lawyer, or a founder of a startup or a web3 company, you will experience cash flow issues. Studies show that the vast majority of business owners have at least once in their lives.
Knowing exactly when that cash flow issue will come, and what you are able to do to mitigate the problem is a definite advantage. One that will let you sleep a whole lot better at night. And that's exactly why cash flow forecasting is a must-have tool.
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Knowing exactly where your business cash flow is headed will let you sleep a whole lot better at night. And that's exactly why cash flow forecasts are a must have tool for every small business.
As a business owner you are busy. This definitive guide will show how managerial accounting will get you back to your entrepreneurial dream: creating something you love, helping people in the process, and earning money and free time while doing so.
