The Courage to Take Risks

In the world of outside sales, playing it safe might seem like a smart move. It feels comfortable. Predictable. Easy to explain. But comfort does not drive growth. In fact, too much predictability can kill your credibility. If you never take a risk, you never stand out. And in a competitive market, standing out is everything. This is especially true in marketing. Predictable marketing is forgettable marketing. It blends into the background. It feels like wallpaper. It is there, but unnoticed. Great marketing, like great sales strategy, requires courage. It demands bold decisions. It takes risk.

The business world is full of examples showing that those who take smart risks often rise above the rest. As marketing pioneer David Ogilvy once said, “Don’t bunt. Aim out of the ballpark. Aim for the company of immortals.” Ogilvy wasn’t just talking about advertising. He was talking about making something that people remember. Something that feels different. That kind of marketing, and that kind of selling, only happens when people have the courage to break the mold.

In outside sales, buyers are bombarded with pitches, offers, and messages every day. Most of them sound the same. They’re full of buzzwords, generic promises, and safe language. But buyers don’t remember safe. They remember brave. They remember bold. They remember something that made them pause, think, laugh, or feel. That’s where risk comes in. When you take a risk, when you say something that others are afraid to say, or show something in a new way, you stop sounding like everyone else. You create a moment. And moments are how deals are made.

Risk is not about being reckless. It’s about being willing to move beyond the obvious. It means daring to share a new idea. Trying a new campaign. Challenging the usual playbook. When Steve Jobs introduced the iPod in 2001, he didn’t say it was a new MP3 player. He said, “1,000 songs in your pocket.” It was bold. Simple. Emotional. And risky. At the time, Apple was not the leader in personal electronics. But that message worked because it was different. It connected. And it changed everything. Today, smart marketers can learn from this. The courage to be clear and original is worth more than a stack of “safe” bullet points.

There’s also a deeper human truth here. People don’t want perfection. They want honesty. They want authenticity. Taking risks in your marketing shows that you’re willing to be real. It tells the buyer, “We’re not afraid to stand for something.” That’s powerful. Predictability says, “We’re trying not to lose.” Courage says, “We’re here to win.” In the long run, buyers trust bold companies more than they trust quiet ones. A Harvard Business Review article once put it this way: “Companies that play not to lose rarely win.”

The science backs this up. In a study published in the Journal of Business Research, we learn campaigns using unconventional creative strategies were 27% more likely to be remembered. That is when compared to the recall of traditional ones. Memory is the gateway to action. If people don’t remember you, they can’t choose you. So, if your message feels like every other message out there, you’re already losing. Your competitor doesn’t even have to beat you; they only have to be a little more memorable.

In outside sales, there’s another challenge: the gatekeeper. You’re not always selling direct to the final decision maker. You might be talking to assistants, marketing directors, or junior buyers. These people are trained to ignore things that don’t feel urgent or exciting. Safe messages die at the door. But something that feels bold, something that surprises; those messages get passed along. They break through. This is where courage pays off. It’s the difference between being ignored and being discussed.

We often forget that marketing is a form of storytelling. And every great story includes a risk. Imagine a movie where nothing goes wrong, no one takes a chance, and everything goes exactly as planned. Boring, right? Stories live in conflict. In risk. In the chance that things might not work, but they try anyway. The same is true for your brand. If your message doesn’t take a chance, it doesn’t have a story. And without a story, no one will care. As author Seth Godin wrote, “Marketing is no longer about the stuff you make, but about the stories you tell.”

In sales, especially outside sales, relationships are everything. But relationships don’t start with facts and features. They start with emotion. With curiosity. With surprise. That means taking a risk to be interesting. To be different. Predictable sellers often hide behind long presentations, charts, and safe language. But courageous sellers lead with questions. With bold ideas. With a sense of purpose. That doesn’t mean you ignore data. It means you use it to support something worth hearing.

It’s worth remembering that buyers are people. And people are drawn to courage. They admire it. They respond to it. In fact, one of the fastest ways to build trust with a prospect is to take a small, smart risk early in the relationship. That might mean sharing a tough truth. Asking a difficult question. Or suggesting a new approach that challenges their thinking. These moves might feel risky, but they signal strength. They show that you’re not only trying to win a deal, but you are also trying to do what’s right. And that makes you stand out.

There’s another angle here too: the speed of change. Today’s business environment is moving fast. Technology shifts, customer expectations grow, and markets change in months, not years. What worked yesterday won’t work tomorrow. Playing it safe is not actually safe. It’s dangerous. Because while you stick to the old plan, your competitors are testing new ones. They’re learning. They’re adapting. They’re growing. As marketing guru Gary Vaynerchuk put it, “Playing it safe is the riskiest move of all.”

This is especially true in industries that are changing with speed like tech, media, or healthcare. In these fields, buyers expect innovation. They want to work with partners who are forward-thinking. If your marketing still looks like it did five years ago, it sends the wrong message. It says, “We’re stuck.” Risk, on the other hand, signals relevance. It tells the buyer, “We’re thinking ahead. We’re not afraid to evolve.” That kind of message earns attention. And in sales, attention is the first step to revenue.

Let’s look at some data. According to the Nielsen Global Trust in Advertising report, ads that were “entertaining” or “unique” had a 42% higher engagement rate. That is when compared to ads that were “informative” but bland. That tells us something important. Information is not enough. If your ad, or your presentation, doesn’t stir emotion, it gets lost. Predictability kills emotion. But creativity sparks it. So, if you want your marketing to work, it must be more than correct. It must be courageous.

This applies to sales conversations too. Predictable sellers follow the same script. They open with pleasantries. They ask surface-level questions. They wait for a buying signal. But the best sellers challenge assumptions. They ask, “What if there’s a better way?” They say, “We noticed something that might be costing you money.” These conversations feel risky. But they also feel real. And that’s what moves the deal forward.

There’s another benefit to risk: growth. When your team takes creative risks in messaging, they learn faster. Some campaigns will miss. That’s okay. Because the misses teach you more than playing it safe ever will. Thomas Edison said, “I have not failed. I’ve just found 10,000 ways that won’t work.” The mindset of bold trial and error is how the best sales and marketing teams operate. They test. They learn. They improve. And then they hit on something great.

This also builds culture. A sales team that rewards creativity and bold thinking becomes more energized. People feel free to contribute ideas. They take ownership. They act with confidence. Compare that to a team where everyone is afraid to fail. In that kind of culture, nobody shares. Nobody risks. Nobody grows. And sales suffer because of it.

Risk also plays a role in credibility. This might sound backward, but it’s true. Buyers trust those who admit uncertainty more than those who pretend to have all the answers. If you take a stand, and admit it might not work for everyone, it shows honesty. It shows self-awareness. And it builds trust. Predictable sellers often say, “This is perfect for everyone.” That sounds fake. But a brave seller might say, “This won’t work for every company, but for the right one, it’s a game-changer.” That’s credibility. And it earns respect.

Even pricing can enjoy boldness. Many companies are afraid to charge what they’re worth. They fear rejection. So, they underprice. But underpricing is often a sign of under confidence. When you know the value you bring, and you have the courage to stand behind it, you price accordingly. And the right buyers respect that. Harvard Business School research has shown that premium pricing often signals quality to buyers. So, charging more, when supported by a bold message, can actually improve your results.

There’s also the matter of differentiation. In crowded markets, being different is more important than being better. If everyone sounds the same, the buyer can’t tell who’s good. So, they default to price. But when your message is brave, when it makes people pause, you’re no longer just another option. You become the only option in a category of one. That’s the real goal of great marketing.

Of course, not every risk pays off. But most failures in marketing are not because someone took a bold risk. They fail because no one noticed them. They were too safe. Too expected. Too boring. The real danger isn’t in standing out, it’s in blending in. As business strategist Peter Drucker once said, “People who don’t take risks generally make about two big mistakes a year. People who do take risks generally make about two big mistakes a year.” The message? You might as well take the risk. You’ll make mistakes either way. But only one path gives you a shot at greatness.

It’s also worth mentioning that courage is contagious. When a company makes a bold move, others follow. When a leader takes a stand, the team rallies. When a seller says something brave, the buyer leans in. This kind of energy can change the culture of an entire organization. It creates momentum. And in sales, momentum matters. In the end, the question isn’t, “Is it risky?” The question is, “Is it worth remembering?”

Predictable marketing dies fast. But bold marketing creates conversations. And conversations create deals. Outside sales organizations must accept this truth: safe will not get you seen. If you want attention, you must earn it. If you want trust, you must speak the truth. If you want growth, you must step into discomfort. The courage to take a smart risk today may be the very thing that defines your success tomorrow.

My new book, Double Your Revenue, is now available on Amazon. If you like what you have read, please consider ordering a copy or two. You can always send one to a friend. Order a copy here: https://bit.ly/doubleyourrevenuebyCEFleming