How to Develop Entrepreneurial Mindset: Be Cautiously Bold

Kelly Masson October 5, 2022
Confident woman business owner with her arms crossed thinks about her entrepreneurial mindset

The Cautious-Bold Continuum

When it comes to entrepreneurial mindset, I’ve noticed that many early entrepreneurs fall into a continuum. On one end is the bold entrepreneur. This person signs a business lease before they have the money to pay the rent, shells out $50,000 to manufacture a prototype for a (hopefully) revolutionary product, and shouts about their product from the rooftops (even if it’s not quite ready…). This person is in business!

On the other side is the cautious entrepreneur. This person has a business idea, and they’ve spent countless hours working on their logo, crafting a perfect business plan, and researching the market. If they can do something sitting comfortably behind their desk, they’ve probably done it. They might tell a few friends about their idea, but they keep it pretty quiet in case it doesn’t work out. And, critically, they often struggle to execute their idea. 

Do either of these sound familiar? Maybe too familiar? The good news is, there’s no right way or wrong way to be an entrepreneur. With a bit of work, you can adjust your mindset to become a better entrepreneur. 

If you’re naturally cautious, how can you become more bold to drive your business forward? And if your boldness is becoming a liability, what tactics can help you become more cautious and balanced? 

As a Business Advisor, I’m also a Certified Entrepreneurial Mindset Profile® Practitioner. In this post, I will explore some of the characteristics of successful entrepreneurs (based on the EMP framework) and some tips on how to take action.

Balancing Your Entrepreneurial Mindset

Entrepreneurial Mindset: Risk Acceptance

Entrepreneurship involves risk—there’s no getting around that. Some people are scared to take any risks, and some people bet the farm to less-than-ideal results. But the good news is, anyone can shift their mindset to become more risk astute. Here are some actions you can take.

Tips for Becoming Bold:

  • No risk, no business: Think about shifting your mindset to see risk as a necessary part of building a business. You know what they say—No risk, no reward! Many successful entrepreneurs will say that the real risk comes from missed opportunities. So instead of thinking of risk as a potential loss, think about it instead as a potential gain, and an unavoidable part of doing business.
  • Be logical about your fears: An inability to take risks often comes from a place of fear. Next time you have to make a big decision, think through the worst case scenario. What is really the worst that could go wrong? How could that be mitigated?
  • Practice risk and experimentation: Try taking small risks in your day-to-day life. Order something new at a restaurant, or (gasp!) let Netflix pick the TV show for you. Then apply this mindset to your business, and start small! Change the colour on your website or try a new promotion. You will see that risk-taking can be beneficial, and not as scary as you thought.

Tips for Becoming Cautious:

  • Use a Risk Matrix: If you tend to take risks without always thinking it through, then maybe you need some tools in your toolbox. One approach is to use a risk matrix. 

    To put together a risk matrix, write down all of the risks you could face when starting your business or embarking on a new project. Then, rate each risk based on 1) the probability of it happening, and 2) the level of harm it would result in (there are lots of examples online!). You will soon see that some risks are ‘riskier’ than others, which will guide your decision making.
  • Learn about Risk Control: Risk control helps you to treat risk in certain ways to lessen their impact. You can use tactics to avoid the risk, transfer the risk to someone else, mitigate the impact of the risk by taking some pre-emptive action, or accept the risk and plan for contingency. Using risk control and a risk matrix together is a winning combination!

Be clear about what you need input on. Instead of asking, “What should we do?” try saying, “Here’s what I’d like to do, and here’s why.”

Entrepreneurial Mindset: Action Orientation

Entrepreneurs often have high Action Orientation, which means they like to take quick and decisive action. This is usually good, but not if you’re acting based on incomplete information. On the other hand, people with low Action Orientation are more likely to hold back on taking action, usually because they want more information before they make a decision. They may also be procrastinating—driven by perfectionism or a fear of failure. 

Tips for Becoming Bold:

  • Map your decisions: If you’re an analytical person, it can be hard to make decisions. I call this “Analysis Paralysis.” But, you can also put those skills to good use to become more Action Oriented. When you’re getting stuck on a decision, take the time to map things out at a really high level. 

    What is the decision you need to make? What is your deadline to make the decision? What information do you need before you can make the decision? 

    This map can serve as a touchpoint when you find yourself going down rabbit holes (It’s funny what you will spend your time on when avoiding making a decision!)
  • Practice taking action: Much like risk taking, it takes practice to develop action orientation. Try breaking down a task into small pieces and set timelines for each piece (e.g. take four hours to price production costs or research potential suppliers). 

    Allow yourself that set amount of time for the task, then walk away and take a break. Then, revisit your decision map. What does your gut tell you based on your analysis? Still need more information? That’s ok, but limit the time, and always check back on your map.
  • Change your mindset: Entrepreneurs must move quickly to adapt to changes in the market—that’s just the way it is. Try treating this as a core competency or value that you can work on, rather than a shortcoming. For example, you could name this in your business strategy as part of your mission or values—“We make thoughtful, expedient decisions to stay ahead of trends and maximize profit.” 

Tips for Becoming Cautious:

  • Build  a circle of advisors: Action-oriented people tend to make decisions independently but, as they say, “If you want to go fast, go alone; if you want to go far, go together.” 

    So set up a structure that works for you to consult with people you trust, but don’t get bogged down in consensus building or bureaucracy. Be clear about what you need input on. Instead of asking, “What should we do?” try saying, “Here’s what I’d like to do, and here’s why.”
  • Back up your gut feelings: You don’t want to get analysis paralysis, but you need more than your gut to make decisions. Use the mapping exercise outlined above under “Becoming Bold,” Allow yourself the time to dig into your question, and don’t be afraid to delegate the research if it’s not your skill set—just be sure to listen once you get the results!

Engage with other entrepreneurs to learn about their challenges and successes. You will quickly see that no one knows everything, and even the most successful entrepreneurs question their abilities sometimes. 

Entrepreneurial Mindset: Self-Confidence

Finally, let’s discuss self-confidence. Many entrepreneurs have high self-confidence—they believe they have the skills and talents needed to reach their goals. This can help them get others to rally behind their mission, but also can come across as arrogant. 

What if you lack confidence? Well, this can make it hard to gain trust, and second-guessing yourself is sure to slow down decision-making. 

Tips for Becoming Bold:

  • Remind yourself of your awesomeness: It’s normal to feel overwhelmed and like you don’t have what it takes. No one knows everything about everything. 

    Write down a few things that you recently succeeded at doing. When you’re lacking confidence, look at this list to remind yourself you’re capable of success.
  • Act as if: Sometimes it helps to “act as if” you are already a successful business person, even if you feel like you’re pretending. Ask yourself what a successful business person would do, and then do it! Confidence breeds confidence. 
  • Connect with a community: Engage with other entrepreneurs to learn about their challenges and successes. You will quickly see that no one knows everything, and even the most successful entrepreneurs question their abilities sometimes. 
  • Be the best: Want to build your confidence? Offer the best product or service you can. Build your skills and knowledge by taking courses, joining industry associations, and keeping up with the latest developments. When your business is successful, your confidence will grow. 

Tips for Becoming Cautious:

  • Look at the source: Sometimes high self-confidence is actually low self-esteem in disguise. Do you find yourself constantly trying to prove yourself? You might want to adopt the mantra “Show, don’t tell.” Let your actions and results speak for themselves.
  • Ask questions: Here’s another saying: “You have two ears and one mouth for a reason.” If you’re prone to talking a lot, make an active effort to listen more and speak less. When you do speak, try asking more questions.

Wherever you sit on the bold-cautious continuum, I hope these tips give you some tangible ideas for how to adjust your entrepreneurial mindset and get your business to the next level!

About Kelly Masson

Kelly Masson is a WeBC Business Advisor (BA) based out of Nanaimo. She understands the impact small businesses can make on individuals, families, and communities and is thrilled to work with entrepreneurs as they pursue their unique missions. As a BA for WeBC, Kelly’s favourite question to ask clients is, “is the juice worth the squeeze?” In other words: do you know if your efforts are getting results? If you don’t know, she will help you find out!

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