September 10

Why It’s Important to Take Risks in Your Business and Life with Hayley Luckadoo


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Have you ever taken a risk when it comes to your business? Even though it can feel terrifying, facing these (sometimes) scary risks can totally change your business for the better.

In episode 029 of the Rebel Boss Ladies Podcast, we’re talking to Hayley Luckadoo about risk. Hayley is a speaker and coach, and she loves to empower women to take steps toward big dreams and a better life.

The Powerful Impact of Risks On Your Business - yes, risks are scary. But without them, your business won't grow. Here's how you can get comfortable taking risks in your business and in your life. #businessrisk #businesstips #mindsettips

Hayley is a serial entrepreneur and big dreamer who took a hobby wedding planning business born out of a college dorm room and created a multi-business empire that runs on hard work and Dr. Pepper. Through her speaking, businesses and passion project, the Females on Fire podcast, Hayley spends her days in her pink office, creating content and resources that help women turn their ‘what ifs’ into tangible realities.

Running a business is scary. There are all kinds of twists and turns and lots and lots of unknowns. Today, Hayley's going to share her unique story with you about the risks she took in her business, her successes, failures, and why they were essential in making her business into what it is today.

Before we continue though…

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Hayley Luckadoo: College Student to Risk-Taking Multi-Business Entrepreneur

Today Hayley calls herself a serial entrepreneur, but obviously she had to start somewhere.

She started her first wedding planning business in college, which was not at all what she set out to do.

“I was a criminal justice major after having changed my major like nine times. And I started this wedding planning business just on my own, no experience, no business degree, no nothing.”

Despite her lack of experience, her business started doing really well and getting a lot of clients. She decided to expand into a virtual assistant business because she saw what other wedding professionals were struggling with and wanted to help.

Hayley’s businesses continued to transition until she arrived at where she is today, which is in the digital marketing space. Even though her business doesn’t do wedding planning anymore, she does a lot of speaking, coaching, a podcast and she’s launched a few courses.

She’s in a space now that she loves. “We’ve gone through a few different types of programs and a few different types of businesses. And all in all, I found that I really just love working with entrepreneurs and specifically female entrepreneurs and just helping them grow their businesses.”

Hayley’s mission is to help female entrepreneurs grow their businesses and advance their careers in ways that will give them the lives and lifestyles that they want.

Instead of getting stuck in one thing, Hayley has let her business grow and evolve along with her. Even though she misses her wedding planning business, which started her entrepreneurial journey, she’s glad that she discovered her passion for working with other entrepreneurs. “It's been an amazing road to get here for sure.”

Risk Taking In Business and Why it is Critical for Success

When it comes to running a business, it’s easy to focus on the tactical and tangible things. These are the step-by-step parts of running a business, like how to grow your Instagram or get more clients. 

But it’s also important to think through ways to grow your business and keep moving forward. “We're so focused on those things that we can control, the things that we really get step-by-step guides for, the things you can Google. But something like taking a risk it's not one of those things. You can't really Google how to get the confidence to take a risk in your business.”

Hayley emphasizes the importance of considering risk and these types of decisions.

“For me, taking a risk is what got me here and it’s what’s grown my business to where it is… I feel like it's just one of those things that people don't like to talk about because it's scary, but it's a necessity. You cannot grow a business and get to the point you want to get to without taking a risk at some point.”

Risk-Taking In Business: How and Why it Feels So Scary

It's really easy to talk about taking risks and how important they are in your business when you're looking back and talking from a point of success. 

But when you’re actually in the trenches taking those risks, it can be pretty terrifying.

If this is how you’re feeling, you’re definitely not the only one. “I don't think there's a person on the planet who's staring down a risk that they need to take and is not scared. I think you can pretend not to be scared, but everybody's scared,” says Hayley.

The Powerful Impact of Risks On Your Business - yes, risks are scary. But without them, your business won't grow. Here's how you can get comfortable taking risks in your business and in your life. #businessrisk #businesstips #mindsettips

Part of the definition of a risk is you don’t know how things will turn out, which is one of the reasons that taking risks can be so scary. So how can you handle this when you’re considering taking a risk?

Hayley says, “you've got to go into it saying, ‘OK, I have faith in myself that I can do this. If it doesn't work out, that's gonna be OK. I'll figure out a plan B. I've got a backup plan or I can do something else or we can try it a different way. But I've got to do this or I'm never going to know.’”

She’s had to think this through a lot in her own business. When she started planning parties and weddings when she was in college, she had to make the decision whether or not she should start a business and take her career in a complete opposite direction.

“You don't know what you don't know. And so I got to the point where I was like, I don't know. I don't know if I can do this, but I really feel like I can. And for me, it was just about saying, okay, I'm going to try it. And if it doesn't work out, OK.”

That risk and the decision to start her own business made all of the difference in Hayley’s life, and started her on the path that she’s going today.

Since then, she’s had to take many more risks. She’s decided to open a second business and try a lot of new projects.

Her mindset through it all? “There's a million different reasons why it may not work out, but that's the point of a risk. You don't know how it's going to work out. You just have to put in the work and give it your best shot.”

Turning Risks in Business into the Stepping Stones for Success

Sometimes even the thought of taking a risk or taking too many risks can make you become paralyzed or unable to make any decisions. This can stop you from moving forward and accomplishing anything.

Hayley experienced this right when she was considering starting her business. A lot of things happened all at once, her fiancé left, her financial aid got cut and she admits that she pretty much hit rock bottom.

She spent three days on the couch in tears, but after that she knew she had to get up and do something.

“I just had that nagging in the back of my mind, like, this is what you could do. And I feel like we all have that when we've got that thing that we want to try. But we're scared, too. It nags us because we know we're supposed to try it. We're just too scared to.”

Hayley did try it, and the risks she took ended up being incredibly successful. She told herself that she had nowhere else to go but up, and she took that risk and turned her rock-bottom situation into what is now multiple successful businesses. 

“Now I look back on that and I'm like, wow, was it really rock bottom? Or was it just the stepping stone to get me where I am?” says Hayley.

Everybody Takes Business Risks, Even Our Business Idols

No matter who they are, everybody takes risks in this field. Even your uber-successful entrepreneur idols definitely had to take a risk at some point to get to where they are today. In fact, they’re probably still taking risks.

“We get to that point where we're like, oh, well, they're successful. They have money. They've been doing it for years. They've got whatever. So they can't possibly understand what I'm feeling right now. And the reality is, they were probably there at some point and they just chose to get up and do whatever it was.”

Everyone experiences pitfalls and hard moments. Even the people that seem to be doing extremely well have probably faced a lot of challenges and put in a lot of hard work throughout their entrepreneurial journey.

Just because you decide to take a risk doesn’t mean that you’ll have it easy. There will be setbacks and even failures along the way. However, being willing to take those risks in the first place is what sets apart extremely successful people.

The big names in the online marketing space also started out with nothing, but they kept showing up and taking the risks. “They have all of those same things. It's just they've gotten to this level that we think we can't reach. And if you just start looking at them as normal people who probably went through the same things you're currently going to through, then it makes all the difference in the world because all of a sudden it's not so unattainable.”

Making Business Risk-Taking Easier: Why It’s Important to Have a Support System

The Powerful Impact of Risks On Your Business - yes, risks are scary. But without them, your business won't grow. Here's how you can get comfortable taking risks in your business and in your life. #businessrisk #businesstips #mindsettips

Hayley says that having her support system around her while she was taking risks in her business was one thing that made it a lot easier. It’s essential to find someone who can encourage you to take risks, remind you of everything that you’ve accomplished, and make sure that you’re getting back up after a setback or a failure.

For Hayley, that person was her mom. Her mom made sure that when she was feeling like she couldn’t succeed or was struggling to make everything work, Hayley got back up and tried again.

“I don't remember much of those three days that I sat on the couch crying that my life was over. But I know my mom was sitting right there the entire time and she gave me like the three days. And then she was like, OK, get up. You're not doing this anymore.”

When you’re facing those hard decisions, you don’t want to look back at everything you’ve accomplished. “You just want to sit there and be sad and be worried and not take the next step.”

That’s why Hayley emphasizes that it’s essential to have somebody to support you throughout this. “It doesn't matter who it is. It doesn't matter if they're actually physically with you all the time. But you've got to have somebody that you can call or you can text or you can talk to who is going to say ‘no, look at all that you've done so far. You're gonna be fine.’”

Finding Your Support System to Help you Take Those Risks in Your Business

Hayley admits that she’s really lucky that she has her mom and her husband to help her think through the risks that she’s taking in her business. Not everyone has such a great support system.

If you’re not sure who to reach out to or how to build that support, Hayley says that she’s also found a lot of support on Facebook.

“Find Facebook groups that resonate with you. You know, if you're a female entrepreneur, there's a million Facebook groups out there for female entrepreneurs, female creatives. Nine-to-five workers who also have side hustles, moms. I mean, there's thousands of groups. Join a group and just say, ‘hey, I'm looking for a friend.’”

Even putting yourself out there can feel like a risk. But there are so many people in that online space who are going through the same things that you are, and these people can be an incredible support system.

Hayley’s also made some incredible friends online. She says that one of the best parts about this is having other people understand what she’s going through because they’ve gone through it themselves. Even though she’s grateful for the support of her family and husband, they haven’t experienced what she’s going through themselves.

“Just reach out wherever you can reach out, whether that's a Facebook group, whether it's on Instagram or somebody you follow, whether it's a networking event in your hometown, whatever it is. Just reach out to somebody, because I guarantee you there's somebody in your exact same situation.”

There are so many online communities that can help you find your niche and your people. Everyone wants a sense of community and a feeling of understanding, so if you’re willing to take that risk to put yourself out there, you’ll definitely find other people to catch you.

Finding Your Risk-Taking Mindset

If you’re in the process of creating a business or starting to grow your business, it’s easy to fall into the trap of thinking that you only need to take a few risks to make it to your goal, and after that it’s smooth sailing.

That’s definitely not the case. Once you reach your goal, there are always more risks to take to keep moving forward. In reality, entrepreneurship is a series of risk after risk after risk. You have to learn to handle that fear, and approach your business with a risk-taking mindset.

Hayley emphasizes that this risk-taking never truly goes away. “When you take one risk, if it fails, you've got to go take another one. If it works out, you’ve got to go take another one.”

It’s a constant cycle of risk taking, and eventually you will face a setback or possibly failure. “So that's the thing, is you've just got to keep taking them over and over and over again, because whenever you get to that level that you want to get to, you're going to realize that now there's a new level that you want to get to and you're not done yet and you're not there yet. And that means more risks.”

The bigger your business gets or the more money you make, it often means that the risks and the stakes for your business also get higher. Maybe there’s more money or resources invested, maybe you’re hiring someone else to help you with your business, which can be a risk.

“People get to that point where they think that they're going to reach this goal and then they're going to be happy and they're going to have money. And it's all going to be fine when in reality it's bigger risks. And I think you just learn how to cope with that.”

The strategy that Hayley uses to cope with this constant risk-taking is reminding herself how far she’s come in her journey. She thinks of the risks she’s taken previously and how successful those were, and uses those successes to motivate her decisions.

She says, “For me, if I take a risk from now and I fail or I have a setback, it's going to be nothing, because I know that the risks I've already taken worked out even better than I could have fathomed. And I've already had a setback. It put me right at rock bottom and you can't go any lower than rock bottom. So I know that even if something happens and I hit rock bottom again, I've already gotten up. And so I know I can do it.”

What If You Succeed? Looking For the Positives In Risk-Taking

The Powerful Impact of Risks On Your Business - yes, risks are scary. But without them, your business won't grow. Here's how you can get comfortable taking risks in your business and in your life. #businessrisk #businesstips #mindsettips

Risk-taking is definitely one of the more challenging parts of owning your own business. It also may be why entrepreneurship isn’t necessarily suited for everyone.

When you're working a traditional 9-to-5 job, the risks aren't your risks. They're your boss's risks. The risks that you’re taking have much different stakes, but ultimately it’s not your business that’s on the line.

However if you’re reading or listening to this episode, you've probably already chosen to pursue entrepreneurship and can get over this. It's just a matter of equipping yourself with the tools that are going to enable you to be successful while you're dealing with those risky moments and dealing with that fear of an all of the what ifs that come with that.

If you’ve already started a business and your entrepreneurial journey, then what's holding you back? What's holding you back from taking whatever that next step is? 

“Whatever it is, it's probably not as scary as you're making it out to be. It's probably mostly all in your head. It's probably 90 percent about what if I fail?”

Hayley emphasizes that you can speculate all day about what would happen if you fail, but instead you should be thinking about what would happen if you succeeded.

“What if you get to that level you want to get to? What if you make more money? What if you have more time for your kids? What if you can retire early? What if you can do all of these things and have this life that you dreamed up? Doesn't that sound good?”

You never want to end up in a place in the future where you’re wondering “what if” you had followed your goals and taken those risks.

“That's going to turn into the most disappointing thing that you can say to yourself. I would much rather say, ‘gosh, what if I had done this differently? What if it had worked out?’ What if all of these things, versus having to look in the mirror one day and say, ‘well, what if I had tried? I could have had the life that I always imagined.’”

Risk-Taking Role Model: Hayley Luckadoo

If you want to learn more about Hayley make sure to check out the links below to find her online.

Hayley’s also offering a coupon code to her shop. Use the code “rebel” at to get 20% off of all the goodies you find there.


Hayley’s website – 

Listen to the Females on Fire Podcast –

Follow Hayley on Instagram

Rate & Review Us on iTunes!

Did you enjoy today’s episode? If you did, please head over to iTunes and rate and review us.

Your support means the world to us and it's going to help other people see how amazing this podcast is and how incredible the digital product world can be for your life and for your business.

The first 50 people to rate and review the Rebel Boss Ladies Podcast will be entered into a raffle to receive a $25 gift card. As soon as you leave a review you will automatically be entered to win.

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