Winging It: When it Can Work And When Its Likely to Screw-Up !

Right. Let’s talk about the thing nobody wants to admit but everybody does. Winging it. Making it up as you go along. That moment when a customer asks if you can cater for 150 people next Tuesday and you hear yourself saying “absolutely!” when you’ve never done more than 40. We’ve all been there. And if you say you haven’t, you’re either lying or you’re not really running a business.

Here’s the thing – and this might shock the business school graduates – sometimes winging it is exactly what you need to do. Sometimes it’s what separates the businesses that thrive from the ones that just… exist. But other times? Other times it’s the difference between a learning experience and a complete bloody disaster that ends with you explaining to HMRC why your books look like they were done by a particularly creative five-year-old.

So let’s have an honest conversation about this, shall we? Because I’ve seen both sides. I’ve watched people build empires on nothing but confidence and quick thinking. And I’ve watched others crash and burn so spectacularly that their story becomes a cautionary tale told at business networking events. Usually after the second glass of wine.

The Truth About Small Business

Look, if we’re being honest – and we are being honest here – most of us started our businesses by winging it to some degree. Nobody really knows what they’re doing on day one. Hell, most of us don’t know what we’re doing on day 1,000. The retired teacher who decides to open a bakery? She might make the best sourdough in the county, but does she know about commercial lease negotiations? Does she hell. The chef who finally opens his own restaurant? Brilliant with a knife, might be, but employment law? VAT returns? Health and safety risk assessments? It’s all Greek to him.

And you know what? That’s actually okay. To a point. Because here’s what the corporate consultants won’t tell you – small businesses are built for winging it. We don’t have departments and procedures and committees that need six weeks to decide whether to change the font on the menu. Customer walks in wanting something different? We make it happen. Supplier lets us down? We figure it out. That’s our superpower. While the big boys are having meetings about having meetings, we’re already three pivots ahead.

But – and this is a big but – there’s winging it and there’s winging it. There’s the kind where you’re improvising within your capabilities, stretching yourself but not breaking anything important. And then there’s the kind where you’re tap dancing on a minefield, hoping your luck holds out. One leads to growth and innovation. The other leads to a very uncomfortable conversation with your accountant. Or worse, your lawyer.

When Magic Happens

Let me tell you about some real businesses that turned chaos into opportunity. Take The Amazing Max, a magician who saw his live performance business evaporate overnight when COVID hit. Rather than fold, Max and his producer Christine Cox pivoted to virtual magic lessons for kids. Within six hours of launching, they’d booked 25 lessons. In just three weeks, they’d completed 179 lessons. Parents got a break, kids learned magic, and Max kept his business alive. Pure improvisation, brilliantly executed.

Or consider SEA TO SKY SOURDOUGH BRED INC., a cafe that transformed into a grocery store practically overnight. When dining restrictions hit, they didn’t just offer takeaway – they started selling flour, recipe books, house-marinated olives, and locally made hot sauce. They kept their core mission – providing healthy organic sourdough – but completely reimagined how to deliver it. Their regular customers stayed loyal because the business evolved to meet their changing needs.

Then there’s Mallard Printing, who faced a devastating blow when their biggest clients – a national coffee chain and event planners – cancelled all their orders as COVID hit. Jeff, the owner, could have closed shop. Instead, they pivoted completely, using their printing capabilities to produce PPE and safety materials. The Paycheck Protection Program helped, but it was their ability to see opportunity in crisis that saved them. As Jeff said, “My business partner Bob and I always say that we have 23 employees that depend on us being open, and we’ll fight and keep fighting”.

Or take Banzai International Inc, an LA-based company that hosted in-person conferences. When the pandemic hit, only 13% of their events were online, and they didn’t have the infrastructure to scale. Rather than accept defeat, they acquired a small Houston firm called High Attendance that specialized in virtual events. They rebranded as Banzai Virtual practically overnight, and their volume of events soon surpassed pre-pandemic numbers, with clients like Google and Hitachi.

That’s winging it done right. They saw opportunities, took calculated risks, and pulled it off through sheer determination and smart thinking. The key word there? Calculated. They knew their core capabilities. They weren’t trying to do something completely outside their wheelhouse – they were stretching what they already did well.

When It All Goes Wrong

But now let me tell you about the other side. According to Industry Canada, “the main reason for business failure is inexperienced management. Managers of bankrupt firms do not have the experience, knowledge, or vision to run their businesses”. And nowhere does this show up more clearly than when people think they can wing it in areas where winging it can kill you.

Health and safety violations can lead to hefty fines and possible jail time for the business owner. I’m not being dramatic here. When businesses flout the rules, it erodes customers’ trust. It makes them less likely to do business with that company. In some cases, customers may even take their business to a competitor with a better track record of compliance.

Think about it. Depending on the nature of the violation, you could face a misdemeanour or felony charge, which carries significant fines and jail time. In addition, a criminal record can make it challenging to get hired for jobs or obtain professional licenses. If you are convicted of a crime, you may also lose your business licence and be banned from operating your business.

And it’s not just the big stuff. Up to 82% of small businesses fail due to poor financial management and cash flow issues. That’s not because they couldn’t sell their product or service. It’s because they thought they could guess their way through the numbers. Research done by Dun & Bradstreet found that 82% of small business failures are partially attributed to poor cash flow management.

43% of small businesses do not track their inventory or use a manual process. And 55% of small businesses do not track their assets or use a manual process. They’re literally winging it with their own money. How’s that for terrifying?

See, here’s the brutal truth – winging it works until it doesn’t. And when it stops working in certain areas, it doesn’t just stop working. It explodes. It takes your business, your reputation, sometimes your home with it. The trick is knowing where you can improvise and where you absolutely, categorically cannot.

The No-Go Zones

Right, let’s be crystal clear about this. There are some areas where winging it isn’t brave or entrepreneurial or agile. It’s stupid. And potentially criminal. These are your no-go zones:

Anything involving the tax man – HMRC doesn’t care that you “thought” you were doing it right. They don’t care that you meant to keep proper records but got busy. They want their money, they want it calculated correctly, and they want it on time. The loss of a business licence or permit can devastate a company, as it can prevent them from operating legally. In some cases, it may also lead to the revocation of their insurance policies.

Health and safety – I know, I know, it feels like bureaucratic nonsense half the time. But you know what’s worse than filling out risk assessments? Explaining to a judge why you didn’t have one when someone got hurt. Or trying to run a business from prison because someone died on your watch.

Employment law – Think you can wing it with contracts? Holiday pay? Disciplinary procedures? Think again. Employment tribunals are full of small business owners who thought “we’re like a family here” meant they didn’t need proper procedures. Turns out judges prefer paperwork to good intentions.

Financial records – “I’ll catch up on the bookkeeping later” is the business equivalent of “I’ll start the diet on Monday.” Except instead of getting fat, you get fined. Or you can’t get a loan when you desperately need one because you can’t prove your income. Or you pay too much tax because you can’t claim legitimate expenses you didn’t record.

Legal compliance – Licences, permits, insurance, data protection… boring? Yes. Optional? Absolutely not. Not respecting intellectual property laws could lead to costly litigation, while neglecting employment laws might result in damaging disputes or sanctions.

The Warning Signs

So how do you know when you’ve crossed the line from creative problem-solving to dangerous delusion? When you’ve gone from entrepreneurial agility to just making shit up? Here are the signs I’ve seen over and over:

You wake up at 3am every night. Not occasionally – we all have those nights. But every. Single. Night. And it’s not excitement keeping you awake, it’s panic. That sick feeling in your stomach because you know you’re juggling too many balls and you can’t remember which ones are glass.

Your staff are stressed. When you’re winging it successfully, your team feels energised, part of an adventure. When you’re winging it badly, they feel like they’re on a sinking ship with a captain who’s lost the map. They start making mistakes because they don’t know what they’re supposed to be doing. They start leaving because chaos isn’t fun when it’s constant.

Customer complaints shift from “teething problems” to “pattern of failures.” Look, every business drops the ball occasionally. But when you’re constantly firefighting, when every solution creates two new problems, when apologies become your main form of customer communication… that’s not winging it anymore. That’s failing in slow motion.

You can’t remember the last time you did something properly the first time. Everything’s a crisis. Everything’s urgent. You’re not running a business anymore, you’re starring in a really stressful improv show where the audience can ask for their money back.

The gap between what you’re telling people and what’s actually happening gets wider. “Yeah, we can definitely handle that” when you have no idea how. “Business is great!” when you haven’t paid yourself in three months. “We’re just ironing out some kinks” when the whole thing’s held together with prayer and duct tape. When winging it becomes lying, you’re in trouble.

Smart Winging It

But here’s the thing – and this is important – I’m not saying don’t wing it. I’m saying wing it smart. There’s a middle ground between paralysis by analysis and flying blind. It’s about building a framework loose enough to allow improvisation but solid enough to keep you safe.

Studies have found positive correlations between improvisation in product development and team performance. Karl Wieck’s description of the Mann Gulch disaster, for example, shows how an unexpected turn of events fatally trapped 13 firefighters after a lightning storm – but it also shows how the foreman’s improvised solution (lighting an escape fire) saved those who followed him. The difference between life and death was knowing when and how to improvise.

Think of it like jazz. Those musicians aren’t just making random noises. They know their scales, they know their theory, they know their instruments inside out. Then they improvise within that structure. That’s what good business winging it looks like. You know your numbers well enough to make quick calculations. You know your capabilities well enough to stretch without breaking. You know the rules well enough to bend the right ones.

Here’s what smart winging it looks like in practice:

You have systems, but they’re simple ones. Maybe it’s a one-page business plan that you actually look at. Maybe it’s a basic spreadsheet that tells you if you’re making money. Maybe it’s a checklist for taking on new projects. Nothing fancy, nothing that would impress an MBA, but something that keeps you grounded while you’re flying.

You know your non-negotiables. The stuff you’ll always do properly, no matter what. Maybe it’s your accounts – always up to date, always accurate. Maybe it’s your customer service – every complaint gets a response within 24 hours. Maybe it’s your quality – you’ll turn down work before you’ll do it badly. These are your anchors. Everything else can be jazz, but these stay solid.

You build in learning time. When you wing it and it works, you figure out why. When you wing it and it doesn’t, you figure out why. You don’t just lurch from crisis to crisis, learning nothing. You evolve. Today’s improvisation becomes tomorrow’s procedure.

You’re honest about what you don’t know. This is huge. The successful wingers aren’t the ones who pretend they know everything. They’re the ones who say “I don’t know, but I’ll find out” or “I’ve never done this before, but here’s how I think we could approach it.” Customers, staff, suppliers – people respect honesty. They’ll work with you if they trust you’re not just bullshitting them.

The Reality Check

Look, running a small business means winging it sometimes. It just does. You can’t have a procedure for everything. You can’t predict every situation. And frankly, if you could, you’d probably be bored out of your mind. Part of what makes this life addictive is the adrenaline, the problem-solving, the “I can’t believe we pulled that off” moments.

There are positive correlations between improvisation in product development and team performance. Understanding improvisation means you’re better equipped to say, “Yes, and …”; to listen actively; to heighten ideas; to think more creatively and on your feet; and to make the other person look good. Improv works, because it’s not about being funny; it’s about supporting and connecting, which is where creativity lives and ideas flourish.

But – and I cannot stress this enough – there’s a difference between riding the wave and being swept out to sea. There’s a difference between flexible and chaotic. There’s a difference between “we’ll figure it out” and “I have no bloody clue what I’m doing.”

The businesses that survive, that thrive, they know the difference. They wing it in the spaces where winging it makes sense. They improvise on the edges while keeping the core solid. They take calculated risks, not blind leaps. They know when to say “yes, we can do that” and when to say “let me get back to you on that.”

Your Winging It Audit

So here’s my challenge to you. Take a hard look at your business and ask yourself:

Where am I winging it because I’m responsive and agile? Keep doing that. That’s your competitive advantage.

Where am I winging it because I’m scared to face reality? Stop it. Today. Whatever you’re avoiding – the accounts, the employment contracts, the health and safety assessment – face it. It’s never as bad as the anxiety of avoiding it.

Where am I winging it because I don’t know what I don’t know? Get help. Find a mentor, join a business group, hire an advisor. The cost of good advice is always less than the cost of bad mistakes.

Where am I winging it because I think I can’t afford to do it properly? Challenge that assumption. Can you afford not to? What’s the real cost of getting it wrong?

The Permission Slip

And finally, here’s your permission slip. Permission to not have all the answers. Permission to make it up as you go along sometimes. Permission to try things that might not work. Permission to be scared and do it anyway. Permission to be imperfect.

But not permission to be reckless. Not permission to put people at risk. Not permission to ignore the stuff that really matters. Not permission to confuse courage with stupidity.

The best small business owners I know are brilliant wingers. They can pivot on a penny, solve problems with creativity rather than cash, and make their customers feel like anything’s possible. But they also know when to stop playing and follow the rules. They know the difference between a calculated risk and a stupid gamble. They know when to improvise and when to plan.

Most importantly, they know that winging it is a tool, not a strategy. It’s something you do, not something you are. Use it wisely, and it’ll take you places you never imagined. Use it badly, and it’ll take you places you never wanted to go.

So go on. Wing it when it makes sense. Plan it when it matters. And always, always know the difference.

Because at the end of the day, successful winging it isn’t about luck. It’s about judgment. And if you’re reading this, if you’re thinking about this stuff, if you’re trying to get better at it… well, your judgment’s probably better than you think.

Now, if you’ll excuse me, I need to go update my risk assessments. Because I may be all for creative improvisation, but I’m not an idiot.