16 Entrepreneurs Explain How They Make Bold Decisions

Entrepreneurship and decision making go hand-in-hand. Some decisions like firing employees require boldness which is not always a walk in the park. The decisions you make can make or break the future of a business hence due diligence is necessary before making bold decisions.  We asked entrepreneurs and business owners how they make bold decisions and here are the responses.

#1- Making the team understand the decision

Photo Credit: Jacob Landis-Eigsti

Taking risks and making bold decisions are a significant part of business. Bold decisions need to align with overall vision and they need to have buy-in from your team. It's important to have a powerful long-term vision. This year, I implemented some changes which will mean a dip in short term revenue, but will let us grow and scale faster in 2020. Since I know where we need to be in 5 years, I'm able to shape our actions around that long-term plan. However, it's critical that your team understands why these decisions were made, they ways it will impact and benefit them, and the goals our team is working towards. So many times, people simply get rules and changes from leadership and push back. I took great care talking with each team member and gaining buy-in. I need help from my team to implement significant changes, so it's important that they're on board.

Thanks to Jacob Landis-Eigsti

#2- I turn to external help

Photo Credit: Ryan Schuman

We're a small team and like most small businesses, we have a limited budget to work with. When it comes to marketing and how we can maximise our audience reach and sales conversions, I turn to professionals for help. As someone who manages a team, I know all too well the importance of hiring the right people for the job. At the same time, hiring external consultants help me bridge my knowledge and experience gap. For example, we're investing into building out more content assets in the coming months. It may come at a significant expense but not having the right advice can often end up costing more.

Thanks to Ryan Schuman, Team Building Kits!

#3- Basing decisions on first-hand data

Photo Credit: Dr Gavin Chan

The field of cosmetic surgery has evolved a lot in the 15+ years that I have been running my own shop. Customer expectations have shifted, partly because of the sheer amount of information they have at their fingertips, as have the competitiveness of the industry as a whole. I am largely an analytical person and prefer to base decisions on first-hand data. This is what allows me to be confident in my decision when I make changes to the

Thanks to Dr Gavin Chan, Victorian Cosmetic Institute!

#4- Two ways

Photo Credit: Francesca Lormeus

Author Tony Robbins once said: “it is your decisions, not your conditions, that determine your destiny”; which emphasizes the importance of making bold decisions as an entrepreneur. In other words, the decisions that an entrepreneur makes can either build or destroy a company’s assets. Making bold decisions in this case requires due diligence. An entrepreneur cannot make decisions based on emotional impulses but must clearly analyze the consequences of the decision to be made. As an entrepreneur, when I am faced with a bold decision in my practice, I often take time to mentally process the information as evidenced by reflecting on the facts, pros and cons of the decision to be made as well as the long-term possible impacts of my decision. I also ensure that I am in a calm and meditative mental state in order to make an objective decision. At times, I also seek counsel from experts in different areas and research facts in order to make logical decisions.

Thanks to Francesca Lormeus

#5- Is this a strategy others are missing?

Photo Credit: Steph Smith

Before making a bold decision, ask yourself if this is a strategy that other decision-makers aren't seeing? If you've got a unique perspective that other's don't yet see, chances are that a bold decision is a good one. But before you chart a brave new course, it's important to gauge your chances for success and the consequences if things don't work out as planned. As an entrepreneur, it's important to be decisive, but also flexible. Bold decisions are best paired with solid back up plans. As an entrepreneur of a mid-size real estate development group, one of my strengths is being able to act quickly and to take bold bets with higher risk profiles than larger, conservative firms while also having more resources than smaller firms so I can manage the downside when bets don't pay off as expected. At the end of the day, your gut check will let you know if you're ready to go bold or chart a course through safer waters. Remember, there is never one path to success so don't worry about passing up an opportunity that isn't the right one at the right time.

Thanks to Steph Smith, Industrial Partners Group!

#6- Strong personal finances 💰

Photo Credit: Michael Alexis

The #1 thing that has allowed me to make bold decisions in business is taking care of my personal finances. First, I pushed my cost of living extremely low. Second I built up a savings account that can sustain me for a long time. With this base, I’ve removed most of the risk of failure; regardless of what happens to the business I will be okay. The interesting twist is that bold decisions really don’t have to be risky. We do research, make small initial investments, and then double down in areas that show potential.

Thanks to Michael Alexis, The Great Guac Off!

#7-Having a safety net so it feels safer to leap

Photo Credit: Lisa Christen

The biggest challenge about making a bold decision is the risk: what if I fail? What if people think I'm an idiot? So the best thing you can do is take the risk out of the bold decision. Now, of course, you can't actually take the risk out of the outcome… but you can take the risk out of the impact it has on your ego. Surround yourself with people (friends, family, fans) who will be there for you no matter the outcome of your decisions. I always tell myself: if I lost all my money, lost my job, and lost everything I owned, could I still survive? Yes! I could take my family to sleep in a spare bedroom at my parents' house or a friend's house. Not ideal, of course, but nobody would starve or freeze. There's no serious risk for any decision I make because there's always food, shelter, and love around me. If you always have a safety net to catch you, then you're free to try flying.

Thanks to Lisa Christen, Christen Coaching & Consulting LLC!

#8- Living to the critical moments

Photo Credit: A Mueed Qazi

Bold decisions are called bold for a very obvious reason.‎ I have been on the situation of taking decisions for almost 9 years now and tell you what, it’s still tough. And I still need to gather a lot of courage to do so. But it’s that boldness and confidence which everyone’s trust alive. Everyone in the company looks upon you at that critical moment when a decision has to be taken, and you have to live to that. The challenge is we never know whether it’s right or wrong but we believe that it’s the most appropriate and we stand strong for the consequences. That’s what makes us strong, and that’s how I make my decisions, the bold ones.

Thanks to A Mueed Qazi, See Through Hearts!

#9- Starting grounded and ready for the day

Photo Credit: Suja Johnkutty

As an entrepreneur, making bold decisions daily is essential. From the moment one gets up we decide if it will be a momentous day or not. In starting grounded and ready for the day whether it be meditating, reading a passage, catching up on one chapter before or just saying ‘something wonderful is going to happen to me today' sets precedent! This allows those courageous goals to flow much quicker from a grounded place for the busy CEO. It makes taking chaos and disorder to a balanced calm much easier.

Thanks to!

#10- I do a lot of research before

Photo Credit: Paige Arnof-Fenn

I need to feel comfortable and try to collect customer data or talk with key stakeholders to make sure I have considered the decision from multiple perspectives. I do not mind taking risks but I just do not want to be blindsided by something that I should have known or thought about in advance.

Thanks to Paige Arnof-Fenn, Mavens & Moguls!

#11- Trust your guts

Photo Credit: Gayle M. Gruenberg

I have to just do it (scared) and jump in with both feet. That’s how I started my business. I used to be a CPA, but I listened to the little whisper in the back of my mind and started a business as a professional organizer. That was 16 years ago, well before anyone knew what a professional organizer did or who Marie Kondo was. As someone who is fairly cautious, I see both sides of the issue. As an entrepreneur, I have to be willing to take risks, to try something, see how it works out, and be OK if it doesn't. My mother used to say, “If at first you don’t succeed, try, try again” and, “Pick yourself up, dust yourself off, and start all over again. That has stuck with me my whole life, both personally and professionally. Making bold decisions also requires not letting what someone else thinks affect what I do. I have to turn a blind eye and a deaf ear sometimes and just trust my gut. All entrepreneurs do. We have to accept educated input, but ultimately we need to go with what we know to be right.

Thanks to Gayle M. Gruenberg, Let’s Get Organized, LLC!

#12- Projecting my current pace

Photo Credit: Dre Baldwin

I make bold business decisions based on projecting my current pace 5 years into the future: if I stay at this current pace, where will I and my business be in five years? Will more of the same get me anywhere close to where I want to be? If I don’t like the answers to these questions about staying where I am, I decide to take bold action.

Thanks to Dre Baldwin,!

#13- Sleeping on it and asking for feedback

Photo Credit: Deborah Sweeney

I am a business owner who makes a bold decision by doing what may be the boldest thing of all… sleeping on it. I think it helps to sleep on a decision you are unsure of making, rather than rush into it. This gives you much more clarity into the decision-making process. I also seek feedback from my husband and family. I value their input and often find that they know what the next best move is to make for the business.

Thanks to Deborah Sweeney,!

#14-I rely on 3 important steps

Photo Credit: Rachel Pedersen

First, I listen to my gut and make notes regarding what I think is right. Second, I ask several people who I trust (including my husband and my best friend). Third, I list the reasons it's a good decision, and hold firmly to those as I say yes or no.

Thanks to Rachel Pedersen

#15- Taking care of myself first

Photo Credit: Shayne Sherman

Be in a position where you can make bold decisions. This means being in your best shape – mentally, physically, emotionally. It's important to take care of yourself so that you're thinking clearly when you have to make that big call. And it's important to remember that risk is okay, but you should be informed about that risk. Know it's there and don't be afraid of it. Be willing to face it head-on, if it's the right one to make. If you're not in your best shape, you might have difficulties deciding if this is the right decision to make. Take care of yourself so you can take care of your business.

Thanks to Shayne Sherman, TechLoris!

#16- Play the scenario out in my head

Photo Credit: Ted Rollins

When you're a fast-growing entrepreneur (especially in international business), it's safe to estimate that 80 to 90 percent of decisions made are bold ones. With big decisions, I play the scenario out in my head – ‘what if I do or what if I don't do X' – and consider if the projected outcome fulfills a need, fits with our people and culture and if it will make a profit. If the answers to these questions are ‘yes' but the proposition is still a little risky, I generally decide to make a bold decision. Fortunately, being bold has reaped many more benefits for my organization and people than being meek or keeping everything status quo.

Thanks to Ted Rollins, Valeo Groupe!

How do you make bold decisions? Tell us in the comments below. Don’t forget to join our #IamCEO Community

Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

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