LOYB 19 | Dark Side Of Success

The Dark Side Of Success In Business With Jordan Eades

illusion of success life pivot loyb podcast work life balance May 10, 2021

There is a dark side of success that few entrepreneurs talk openly about. Challenges and struggles that we often don't see behind the highlight reel that fills our inboxes and our feeds.  Beliefs that once we hit that next big milestone things will become easier and we can stop sacrificing our health and personal life for our business, only to realize it doesn't work like that.  

Crista Grasso is joined by Jordan Eades from Your Best Business Life and she pulls back the curtain on the dark side of success. She shares her personal experience of letting go of a wildly successful 8-figure business that was taking a toll on her health, family, and life overall and why she gave it all up to go on an epic two-year RV adventure across 40+ states. You will be inspired by Jordan’s story and learn how to come out the other side if you are experiencing the dark side of success.

In this episode, we discuss:

  • 2:15: The impact of scaling a business quickly to 8-figures
  • 6:40: What the illusion of success looks like
  • 7:50: Know when to sell or move on from a successful business
  • 10:56: Why it’s important to talk about the dark side in business
  • 14:40: What to do if you are overwhelmed in your business
  • 20:00: The challenges of letting things go in your business
  • 25:00: Jordan’s top 3 tips on what you should do if you are experiencing the dark side of success
  • 29:00: Where you can learn more about Jordan Eades


Listen to the podcast here:

The Dark Side Of Success In Business With Jordan Eades

[00:00:51] I’m super excited to be talking with Jordan Eades. We are going to dive into a topic that I think and wish that more business owners talk about and this is the dark side of success. Wait until you know Jordan’s story. Let me tell you about Jordan before I have her tell you more about herself. She is the Owner and Creator of Your Best Business Life. She is a serial entrepreneur who ran and sold a highly successful eight-figure general contracting company before she pivoted and launched an epic two-year RV adventure across 40-plus states. She helps female business owners break through the ugly cycle of overworking and burnout to create sustainable and profitable businesses, invest in self-care without feeling guilty and bring joy and pleasure back into their lives. Jordan, I’m super excited that you’re here. Welcome.

[00:01:51] Thank you. I’m super excited to be here.

[00:01:55] We’ve got to dig into this. There was something that happened with the highly successful eight-figure business that you’ve chosen to sell, and then you go across the country for two years in an RV. Let’s talk about that. I would like to dive right into some of the dark side of success and what people at that level experience.

[00:02:18] It didn't start out that way. When my husband and I purchased his family's general contracting company, this was coming out of the crash of 2008. We thought that we had this nice, slow trajectory to get used to our business and get our feet wet as business owners. General contracting was a new foray for me. As an opportunity, we started around military contracting and got into that and our slow growth turned into explosive growth overnight. It's one of those things. I know you talk about a lot getting ready to scale and what that looks like. I would say that we were not ready to scale. As we were climbing those mountains, we had some ideas in our minds of what success would look like when we got to eight figures.

[00:03:13] At the time, and this is common for entrepreneurs, I was in that mindset of I’ll just do whatever it takes. For me, that looked like a lot of long hours, doing all the things and putting my right life on hold in terms of I used to go and do yoga. I hang out with my friends and I had hobbies, but then I felt like I needed to sacrifice all of that for the sake of the business. I also got into that tricky habit of if we get to this point, then I will pull back and do some yoga, then I will finally celebrate our anniversary. It’s also common that we know we have more mountains to climb as we’re trying to reach those success milestones. It gets to be a slippery slope if we’re not prioritizing those things.

“Design your business around your life, not your life around your business” - Jordan Eades Click To Tweet

[00:04:04] I ended up becoming more overwhelmed and exhausted. There were these moments where I would stop and I would think to myself, “Is it supposed to be like this?” At that point, I was going past seven figures and it was like, “This is great, but I’m not feeling so hype.” We got to eight figures and then shouted like, “I feel like crap.” I think normalizing what that feels like or can feel is important. It’s like pulling back the curtain. It’s interesting because I would hear all the time like, “You guys are so successful. You’re killing it.” I’m like, “Yeah, but this is killing me,” because I was prioritizing everything but myself.

[00:04:51] I had a lot of warning signals along the way. I was having a lot of anxiety because my nervous system is in this constant state of stress. I’m constantly on the go. I'm anxious. I can't sleep very well. I'm drinking tons of coffee, then I had trouble concentrating and feeling completely depleted all the time. What happens as a by-product is you start to feel less and less enthusiastic about your business. It’s like something that was exciting in the beginning and super joyful was starting to feel like, “This is a drag. I’m having to do this grind over and over again.”

Dive deeper into each of these topics over on the podcast.

[00:05:33] In the midst of all of this, I should have reached out for support. What happens as we start to reach those pinnacles is we feel afraid to be vulnerable and pull back that curtain to say, “I need some help and support.” I was putting so much pressure on myself to appear like I had it all together and reach these upper echelons. I did want people to see me as credible, competent and smart. Certainly, I didn’t want them to doubt me or my business. I put on the mask. I would run around and then I would say, “I’m fine. I’m great. Nothing to see here,” but at the same time, I’m falling apart in the middle of all of it because I needed the support. I was isolated. This continued for quite a long time. As you talked about, I didn’t know those keys. That’s why I love the Lean Out Method so much to be both successful and sustainable.

[00:06:33] One of the things I talk about a lot is the illusion of success. The illusion of success can take on two forms. There’s the outward illusion where you look at a fancy website, a large social media following and these beautifully crafted emails. You think this person has it all together. Meanwhile, they are in the red and stressed out all the time. The other side that sometimes we don’t recognize at all is when you are successful, your business is successful. What you guys were able to do in that short period of time is amazing and very inspiring. Meanwhile, behind the scenes, you feel like it’s an illusion because you don’t feel the success. You feel like, “I hope nobody sees what I’m experiencing.”

[00:07:23] I’m balancing all of these things at that time. Especially with female entrepreneurs, I know that we know this. I was a mama. I’m deeply involved in my community. I’m running this big business. I’m doing all the things. I’m holding myself together by the scenes, ready to burst at any moment.

“We cannot show up in our business or in our lives when we are in a state of chronic stress.” - Jordan Eades Click To Tweet

[00:07:45] Something happened that a catalyst made you finally say, “This is no longer working. Even though the business is successful, I need a change.” You guys decided to sell the business. That must have been a challenging decision. Walk us through that.

[00:08:03] What’s interesting about it is that it didn’t happen overnight. I tell this story of how Zach and I, feeling one of those stories where you should have felt like you have arrived. We were invited to an all-expense-paid trip to Pebble Beach, one of these big contractor things. Instead of getting out, getting on the golf course, going to the spa and doing all those things, I was holed up in my hotel room, reading a book on anxiety. That was when I knew, even for myself like, “This is not right. I shouldn’t feel this way.” That was when I started having those conversations with Zach like, “Something has to change. We have to do something differently. I can’t organize and restructure it anymore. We have to change the balance.”

[00:08:51] We kept on having those conversations. At the same time, from a health and wellness standpoint, being in chronic stress put me in a state where I started to have autoimmune issues. There came a day where I couldn’t get out of bed. I could no longer do business because I couldn’t get to my business. I had to allow myself to fall apart and I said to Zach, “I have to take a step back. I’m not going to be able to do this in the capacity that I was before. I have to concentrate on getting myself well. I have to know how to do this in a safe, sustainable way. It’s not sustainable right now.” He said, “I don’t want to do this without you.”

[00:09:33] We luckily found two employees in our business who are interested in purchasing the business from us. We decided to make this major life pivot. We had been talking about an RV journey for some time. Both of us are travel fanatics. One of the big pieces is that our son was 7 or 8 at that time and we wanted to be able to spend more time with Isaac. That was the frustrating part about the business as well is that it had pushed out all our family time. Weekends would come around and we were exhausted. We’re like, “Let’s watch a movie.” When we did go on family vacations, Zach and I were so exhausted that we won’t get out and do anything. We were like, “What? We’re going to start over from scratch.” We sold the business, our house and all our belongings. We did take an epic two-year journey across the US and it changed everything for me. It was where I discovered my wellness, my joy, what was meaningful to me and learned a lot about connection and how that would support me. It’s what I do now. It’s a new iteration of business.

Dive deeper into each of these topics over on the podcast.

[00:10:40] For all of you reading, Jordan will be back. This will not be the only time Jordan is on the show. We are going to dig into in a future episode a lot of what she’s doing in her business because it’s important, powerful and helpful for women. I do want to talk about the dark side of success for the people who are there. I bet as readers are reading your story, there are some parallels that they’re probably seeing in their own lives. Why now, in particular, do you think it’s important that we be talking about this?

[00:11:14] We’re starting to have these conversations. In the past, we’ve glamorized what it can look like when you get to the top, “Just get to this place and everything will be fine. All your problems will be solved. Joy and happiness will you be yours.” The reality is and we’re seeing this shift coming out of COVID, is that we’re starting to realize that we do need connection. We do need to make sure that we’re taking good care of ourselves. I’ve seen that there are different conversations in and around hustle culture and that we’re not glamorizing or glorifying hustle culture. We’re starting to say, “No, what we should be rewarding is sustainable business practices, which includes making sure that we’re taking care of ourselves, our best selves, do our best work.” With businesses like Lean Out Method, you’ve seen it from a completely different perspective as well. I worked in many companies and they’re saying like, “This doesn’t work. We need to rethink this. We need to work in a leaner capacity.”

[00:12:24] I know a lot of times we see these big, huge companies. We see either corporate companies that are in the billions or we see businesses that are at 7, 8, 9 figures. We think that’s great for them, but “I’m not there yet. I’ll worry about or think about some of those things when I get there.” Working with the Fortune 10 clients that I’m consulting with, they are all putting an emphasis on self-care. They are instructing their staff to reduce the amount of time they’re spending in meetings. They’re trying to help people learn how to be more efficient and leaner in what they’re doing. That way, when they’re working, they’re getting the most out of it and when they’re not working, they don’t have to feel like they’re on all the time. If these big, huge companies are giving these decrees to their huge staff of people, you’ve got to think it is time that you do that in your own business, whether you’re breaking six figures or whether you’re already at that eight-figure mark. These are things that are incredibly important.

“Make sure we are prioritizing things that bring us joy and light us up, aside from our business.” - Jordan Eades Click To Tweet

[00:13:29] It’s a societal conversation about our overall health and wellness and the realization that we cannot effectively run our businesses to show up to our lives when we’re in a state of constant chronic stress. Even through COVID, we were seeing record numbers of people experiencing burnout and everything that comes along with that. Our overall general wellness suffers when we’re putting on the gas without taking some time off, easing off the gas, putting on the brake and taking time to nourish ourselves. I’m happy to see when I get out there and review social media, that there are more conversations about taking time off, working smarter, not harder and making sure that we allow ourselves time to do nothing at all instead of go, go, go all the time. 

[00:14:30] You’ve got to find what fuels you and make time for it. Let’s talk about somebody who might be in that place where they are completely overworked, overwhelmed, maybe they are afraid to pull back the curtain and ask for help because they know that there’s this illusion of success and people look up to them. They don’t want anybody to know that they’re struggling. What are some of the tips that you have there?

[00:14:57] Having these types of conversations and even doing what we’re doing helps to normalize this. They need to know first and foremost that they’re not alone. All of us experienced some anxiety along the way. We’re going to have our failures and successes. It’s normal to doubt your abilities when you’re struggling, question your purpose, lose your wealth, all those types of things. What do we want to be thinking about when we’re in the place? First of all, we want to make our number one priority our physical, mental and emotional wellness. It truly has to be non-negotiable. Remember how I was talking about those if-and-when statements, we want to eliminate those and say, “I will do X. I will go to those yoga classes,” because the success and longevity of our business depend on our best selves showing up.

[00:15:52] Our sustainability is all about making sure that we’re infusing wellness, joy and connection into our calendars. I often have people write down those things in their schedule first so you’re building your business around your practice of taking care of yourself, not the other way around. The other part is if you find yourself in that place where you’re struggling, don’t be afraid to embrace the falling apart because sometimes we can’t move forward until succumbing to the dark side. What’s helpful in those moments is if you take that breath and that breather, you’ll find what will propel you forward. What we resist persists. We need to think about that.

Dive deeper into each of these topics over on the podcast.

[00:16:41] Also, we need to cultivate and engage in experiences that bring us joy and pleasure outside of our businesses. Another trap that I see entrepreneurs falling into is they feel amazing when the business is doing well, and then they completely feel like crap about themselves when the business is struggling instead of seeing it as a normal part of the business experience. Businesses aren't inflowing. They go up and down. We don't want to give the business too much control over our mindset. That's important why I have people who continue to prioritize their hobbies, the things that light them up and bring them joy outside of the business because that's what will bolster us when things get rocky.

[00:17:26] It's important to re-emphasize the feeling of, "I will win." Many of us go into business and we're like, "We just got to get to six figures. When he hit six figures, it's going to be rainbows and unicorns. Things are going to magically work. We're not going to stress about money anymore. It's all going to be good." We get to six figures and we're like, "That's not nearly enough. Seven figures it is," and we work. "I will win. I get to seven figures." Seven figures isn't any different than six-figures and then you do the same for eight. The reality is you have to build now the things that Jordan is talking about because that's what's going to get you quicker to 6, 7 or 8 figures or whatever that looks like for you and your business. You can do it in that sustainable way instead of a way that drives you to burn out. As much as buying an RV and traveling around the US for two years sounds amazing, you want to do that because you want to and it sounds like a great vacation and not because you're burned out.

“Let’s be vulnerable, let’s share our stories, inspiration and what’s it’s like to be on the other side.” - Jordan Eades Click To Tweet

[00:18:37] I had to limp myself into the RV and thank God that I was in the condition to drive it because it took us a lot of time. That’s so true. We have this running joke between the two of us as to how many anniversaries where we’re like, “We could do something, but we’ll get to that next year.” Frankly, I will even say for the two of us, it took a toll on our marriage as well. My life went to the dark side. My marriage went to the dark side. Zach and I could bring it back together. That’s part of nourishing ourselves and each other. As business partners at that time, we could have come back and put all that energy into our business.

[00:19:22] The one thing that I’m always impressed with you for is the fact that you recognize this and you made that difficult decision to say, “This isn’t working for me.” Instead of getting to the point where you ended up in the hospital or with something even worse than what you were experiencing, you guys made the decision to sell the business, rent the RV and do exactly what you wanted to do. A lot of people don’t do that. Give yourself permission to do that if that’s something that you’re thinking of doing. That’s so amazing that you guys did that. I hope that’s something that you’re proud of because it’s huge.

[00:20:00] Thank you for saying and recognizing that. I love how you’re also calling attention to the fact that people do need to give themselves permission to be able to take a step back and go after their dreams in a different way and make changes. We need to give ourselves the permission to make changes when things aren’t working. I know there was a lot of vulnerability that went into that decision for sure, a lot of sadness and grieving because we loved that business so much. We gave so much time, energy and attention. Know that life has a lot of chapters. Frankly, if we hadn’t made that decision, there’s so much learning for myself and personal growth that I wouldn’t have experienced. I would have stayed stuck. I would never give up what I learned on that journey. I wouldn’t have met you. I was able to meet amazing connections because I allowed myself to make a change. I allowed myself to be vulnerable and say, “This isn’t working anymore.” Those are important as well.

[00:21:11] You took the time to commit to letting something go. Let’s talk about the challenges of letting things go and the fact that sometimes even though we know better, those tendencies have a way of coming back. Let’s talk about that in that context.

[00:21:32] There’s a lot of fear that’s underneath it all. It’s all those what-ifs like, “What’s going to happen now if we let this go?” Frankly, I remembered our accountant saying to us, “You guys are crazy to let go of this business,” because everything from the outside looked amazing. It’s impressive to do what we did in that short period of time and reached those milestones of eight figures and be able to do it consistently year after year. All the questions came up of, “Are we going to be okay financially? What are we going to do now? Are our employees going to be okay if we sell this business?” The beauty of it is that you can plan for yourself financially to be able to make these big pivots.

Dive deeper into each of these topics over on the podcast.

[00:22:22] You can discover new parts of yourself, get closer to your zone of genius. Sometimes we have to let things go in order to be able to do that and getting ourselves the support to make those changes. That’s one of the things that’s important for now. You were saying when these things sneak up on you and the old patterns that you write in your head. I will say yes, this is something that I have to work at even in this iteration of this business. It’s making sure that I’m walking my talk in terms of making sure that there are lots of space for wellness, joy and connection. It’s constantly working that path and it’s not always easy. That’s why all of us need that connection and support. That’s why masterminds, group work and coaching are important. It’s something that can come up as we’re learning those new skills again and again.

[00:23:20] For many of us who grew up working hard and feeling like that was how you do business and then it takes a lot of years to learn that there is another way. You do not have to hustle your way to success, but old habits die hard sometimes. No matter how much we logically know it, it can be easy to sometimes fall back into those traps. That’s where people like you come in to keep people like, “Remember self-care and do things that bring you joy.”

[00:23:52] Sometimes we’re building new skillsets, neural pathways and habits. It doesn’t happen overnight when these things are so ingrained in you. It is our culture in terms of like, “Work hard.” Even how we look at retirement, “Work hard for 50, 60, almost close to 70 years of your life and then take a break.” No. That was another part of the RV journey. Zach and I had serious concerns about whether we were going to be able to do some of the things that we wanted to be able to do in a physical sense. At a later time in life, we felt like, “We needed to do this now,” plus spending time with Isaac. We didn’t want to wait to have that family time. That was such an amazing part of that journey was watching Isaac grow, change and experience the world for a couple of years at a special time in his life. What that did to our family bond was nothing short of amazing.

[00:24:59] What are the top three things that you think people should be thinking about if they’re experiencing the dark side of success?

[00:25:07] Curating your community of connection support is paramount. I’ve talked a lot about in the past, “When I got to those upper echelons, I was isolating,” which was dangerous. Isolation is the enemy of wealth and not just wealth in a dollar figure but even our health. Our health is our wealth. As humans, we are biologically designed to connect and attach. It helps us regulate our nervous systems. When we’re working at those at any level, we have to be careful of chronic stress and making sure that we’re staying connected helps us fight against the stressful situations for the body and mind.

[00:25:49] One thing that when we had that RV journey too that I was intentional about is making sure that I was connecting not only with the community in general but also to my business communities. It helped with not being as vulnerable. It’s to get out of isolation. There’s so much synergy that happens. Your possibilities increase. Your creativity thrives. That should always be first and foremost on our minds, especially for those people who tend to be more introverted and think, “I can do this on my own. I’ll be fine.” To some extent, that was me too. That’s one big takeaway.

[00:26:35] Also, revisiting that piece of designing your business around your life and not your life around your business. You can speak to this. This is some of what you’re talking to us about with Lean Out Method and when we do the exercise with time pie and saying like, “We need to make sure that we are prioritizing things that bring us joy and light us up outside of our business, taking time for pleasure.” I certainly was not doing that when I was working with the general contracting company. The number one thing that I’m always talking about is that wellness piece. It’s a non-negotiable top priority. You have to get out and move your body. You have to nourish your gut body with good foods. You have to be thinking about what’s in your general environment and how is that contributing to your overall health and wellness. That’s important.

Dive deeper into each of these topics over on the podcast.

[00:27:33] For a few takeaways there, I do feel blessed to be able to come out of the other side of this and want to encourage women to step forward who are in this place and feeling those questions that I was feeling like, “It should be all rainbows and unicorns. It doesn’t feel very good.” I want to encourage those women to step out of their comfort zone, reach out and get out of isolation. Also, for women who have been there, let’s be vulnerable and share our stories of inspiration and also what it’s like to be on the other side. That’s important as well.

[0:28:10] Too often, it looks glamorous and easy. It looks like rainbows and unicorns. Because of that, people are so afraid. They feel like they’re doing something wrong or other people know something that they must not know because they’re struggling and why are they struggling when everybody else makes it look so easy? We need more conversations like this. We need more people like you who are willing to share their real stories and what happens on your road to success.

“We are not glorifying hustle culture anymore, we are now rewarding sustainable business practices.” -Jordan Eades Click To Tweet

[00:28:41] I’m willing to air the dirty laundry because I know it’s important. I also know what it looks like on the other side and how to get out of it and what we can do. You can have a 6, 7, 8-figure business or even be in that entrepreneurial stage and be doing it without putting yourself in a state of chronic stress or burning out, but we can’t do it if we don’t know how and we need to have those conversations.

[00:29:11] Let’s talk about what you’re doing now. I know I’m going to have you back on and we’re going to dive all into Your Best Business Life. What’s going on for you in your business? Where can people find out more about you?

[00:29:22] I have a one-on-one coaching program, which is phenomenal. I’m enjoying that work and being able to talk about the pillars of business, joy, wellness and connection. I also get to bring in the Lean Out Method, which I love so much. I am doing that. If people want to follow up and find out more about me and more about my work, go to www.YourBestBusinessLife.com. I do have a workshop so people can learn more about that, YourBestBusinessLife.com/Workshop. Also, find me on Facebook @YourBestBusinessLife. We have lots of fun things that are happening there. It feels good to be able to come through this. I talk about personal growth and being able to share that with female business owners and women business entrepreneurs so that they can hopefully, either be in the situation that I was in or get out of it if they’re feeling like they’re in that phase. As women, we need to continue to uplevel each other and this is all part of that.

[00:30:28] Thank you so much for being on the show. This was such a great conversation. We look forward to you coming back and diving much more into Your Best Business Life. Jordan, we will talk soon. Thanks, everyone. See you next time.

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About Jordan Eades 

 Jordan Eades is the Founder of Your Best Business Life. She is a serial entrepreneur who ran and sold a highly successful eight-figure general contracting company before she pivoted and launched an epic two-year RV adventure across 40-plus states.  She helps female business owners break through the ugly cycle of overworking and burnout to create sustainable and profitable businesses, invest in self-care without feeling guilty, and bring joy and pleasure back into their lives.

by Crista Grasso

Crista Grasso is the go-to strategic planning expert for leading global businesses and online entrepreneurs when they want to scale.  Known as the "Business Optimizer", Crista has the ability to quickly cut through noise and focus on optimizing the core things that will make the biggest impact to scale a business simply and sustainably. She specializes in helping businesses gain clarity on the most important things that will drive maximum value for their clients and maximum profits for their business.  She is the creator of the Lean Out Method, 90 Day Lean Out Planner, and host of the Lean Out Your Business Podcast. She is also the founder and CVO of the Profitable Planner Co and Criscara Jewelry.


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