How successful creative business owners keep failure from stopping them

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When we see successful entrepreneurs online, it often seems like they have everything together and that everything they touch turns into gold, right? But I promise you, that is not the case. In fact, for most successful entrepreneurs, there are a lot of quote, unquote, “failures” that lead up to the success that you see.

Today I asked our experts, how have the failures in your business helped you learn and grow? I’m really excited about this. Let’s hear what they have to say.

This season’s experts:

Alisha Robertson

Alisha Robertson is an author, business coach and the founder of Living Over Existing; a podcast, newsletter and community for women entrepreneurs who want to run a successful business without sacrificing the life she desires.

After experiencing severe burnout, Alisha tore down everything she thought she knew about becoming a successful entrepreneur and decided to build a brand that helped women to focus on building their business and life with intention. Through her work, Alisha strives to not only help women entrepreneurs to launch, grow and scale their brands but also help them to prioritize themselves in the process.

Visit Alisha: Website | LOE Collective | LOE Instagram 

Jordan Gil

Jordan Gill, operations consultant and founder of Systems Saved Me, helps overworked one-woman shows become streamlined solopreneurs. Her jam is creating a cohesive operating system for managing your tasks, files and inbox. She’s been on podcasts like What Works and CEO Vibes sharing her love of replacing monthly retainers with one day virtual intensives. She currently lives in Dallas TX with her cavapoo Vivienne and collection of 1,000 piece jigsaw puzzles.

Visit Jordan: Website | Instagram | Facebook

Katelyn Hamilton

Katelyn began her career in marketing and public relations in Nashville, Tennessee. After working in the agency world for six years, she decided to pursue the entrepreneurship route to create more freedom and flexibility in her life. Now, Katelyn works as an Online Business Manager where she helps entrepreneurs organize, strategize and prioritize the backend of their business to go from overwhelmed to out-in-front. A Georgia grad, she bleeds red and black and is a diehard Georgia football fan, dog mom and outdoor enthusiast.

Visit Katelyn: Website | Instagram

Megan Minns

Megan is a Life and Business Coach that specializes in helping online course creators, coaches, and service providers build a scalable, sustainable, and enjoyable business… without sacrificing their personal life!
She does this through her coaching program, Empowered CEO™, and her weekly live show, The Productive Life.
Megan has a Master’s Degree in Organizational and Human Resource Development, corporate Human Resources and Recruiting experience, and has been helping online business owners streamline and systemize their businesses since 2015.

Visit Megan: Website | Empowered CEO |Facebook Group

Quinn Tempest

Quinn Tempest is a business strategist and coach who helps females founders create more purpose + profit in their business *without* burning out. She’s the founder of Create Your Purpose®, a community of global entrepreneurs dedicated to building impactful businesses with intention. Her professional expertise is in branding and holistic digital marketing strategy and she is a frequent speaker at events and organizations around the country.

Visit Quinn: Website | Instagram


Erin Flynn:

Hey there, and welcome back to the show. Now, when we see successful entrepreneurs online, it often seems like they have everything together and that everything they touch turns into gold, right? But I promise you, that is not the case. In fact, for most successful entrepreneurs, there are a lot of quote, unquote, “failures” that lead up to the success that you see. So today I asked our experts, how have the failures in your business helped you learn and grow? I’m really excited about this. Let’s hear what they have to say.

Alisha Robertson:

It’s Alisha Robertson, founder of, and your business coach for all things building a business and life with intention. So, for me, my entire business has been built on failures, but my biggest failure to date has been the crowdfunding campaign that I launched a few years ago for Living Over Existing.

At that time, I really thought that I wanted to create a library of courses that I wanted to offer my audience at an affordable rate. But I knew that in order to get that up and running, to build a website how I wanted it to, to pay for the marketing that it would need, that I needed some money to help back it up. I thought that by running a crowdfunding campaign, that that was going to be the answer to all of my funding issues, but it turned out to not be.

I rushed into the process of launching this crowdfunding campaign. I didn’t take the time to really nurture my audience about it, to build relationships with people who I knew would be able to contribute to it. But I knew that I had an idea and I needed to fund that idea, so I just went for it. It was about a month-long process of me constantly talking about this campaign, of me recording videos, of me going live, of me emailing people and cold emailing people, which I absolutely hate, just for me to get to the end of the month of this crowdfunding campaign, and to have only raised, I think, $2,500 out of the 30,000 I was trying to raise.

I was absolutely crushed. It was a big failure. My ego was hurt. I was embarrassed. It was a, overall, just hot mess, but it took me some time to really get to a point where I could look back at that failure and look at it more as a blessing in disguise, really. Because now that I think about it, that business model that I was trying to build wasn’t sustainable. It wasn’t going to work. It would have taken forever for me to hit my income goals, and it really wasn’t something that I wanted to do. It was, it sound good at the moment. It seemed like it worked for other people, so it was kind of like, “Yeah, it’ll work for me.”

So I’m thankful that that crowdfunding campaign didn’t go the way it should have, because I would have ended up pouring $30,000 into a business model, into an idea that I, one, wasn’t excited about, two, really wasn’t going to work. It really wasn’t a sustainable model in the first place. So I’m just glad that it didn’t work out, because I would have wasted so much time and so much money, and I would have ended up right back at square one again.

So I think when it comes to failures, people always think that the failure is the end of the road, but the failure is what’s going to help you to get to the next level. So we really have to look at that failure of, okay, what good has come out of this? For me, the good that came out of that failed crowdfunding campaign was, I had to take a step back and think about what it was that I really wanted out of my business, and it really forced me to reevaluate the type of business model that I was trying to put out there.

So don’t think of a failure as the last attempt, or the end of the road, or the final chance that you have to build a successful business. I know it’s hard right now, and I definitely think that you should cry your cries and be in your feelings for a while, but once you come out of that, definitely look back at that and say, “Okay, well, what did I learn from this? Or how can I grow from this? Or what did this failure teach me?”

So I always think of failures as little blessings, versus, it’s just the end of the road for what you’re doing. So don’t let it get you down. I know it sucks right now, but failure doesn’t have to be the last time. You can get back up, brush yourself up, and try, and try, and try again until you figure it out. That is what entrepreneurship is about.

All right, you guys. I’m Alisha Robertson. If you want to connect with me, you can head over to Instagram and find me, @thealishanicole.

Jordan Gill:

Hi, I’m Jordan Gill from Systems Saved Me. For me, failures, I call them lessons or opportunities, generally because failures makes it sound like you can’t come back from that, like that’s the end of the score. The cool thing about businesses is it’s not ever the end of the score if you plan to be in business for a long time.

So I would say a major failure that I had, or lesson, would be back in 2017. I did a Systems Saved Me summit, and it was super fun in the sense that I got to collaborate with a lot of awesome people that I’m still connected to and I’m friends with now, and the actual event was really fun. However, on the backend, I was planning to launch a membership site and one person signed up. Like, one singular person signed up for the membership.

I had spent all this money on branding, I had spent all this money on this beautiful website, all of this stuff, and I broke even on the summit. 10 grand out, 10 grand in, and I was like, that sucks. So it was a failure in the sense of, I didn’t make any money from that. However, if I look at the intangibles, or even some tangibles that came from it, in the sense that I got to be more connected and collaborate with a lot of those speakers on other projects that they were doing or that I’ve been doing.

I also got exposure that then allowed me to get more clients or, again, more collaborators or podcast opportunities, stuff like that. That’s a lot of times what happens with launches, is you’re out there and you’re putting all this effort towards stuff, and then everyone’s like, “Oh, I want you on my podcast. I want you to talk to my mastermind.” It was just super fun.

So I’ve been able to leverage every “failure”, quote, unquote, that I’ve had, and I’ve gotten a lot smarter about what opportunities or what marketing strategies I move forward with. I would say now we’ve come to a part where we really have honed them in, and we are pretty good at determining if an opportunity is or was a good decision or not for us.

So that is one big failure that I’ve had, but if you want to connect more and learn more from me, you can go to or find me on Instagram, @systemssavedme, and we can totally have a DM convo.

Katelyn Hamilton:

Hey, this is Katelyn Hamilton, and I’m an online business manager, helping you get organized and create efficiencies in your business. My failures in my business have truly helped me learn and grow over the last few years. I truly think that nothing can be considered a failure as long as you learn from it and you turn it into something positive to help you expand your business, or pivot even, and shift gears. Everything is truly a learning experience.

So, for me, I started a business a few years ago focused in on marketing and public relations. That was what my background in the corporate world was. While I loved the time working with those corporate marketing clients, when I launched my business, I used my current network to grow that, what I found was that that wasn’t bringing me total joy. It was bringing me a lot more frustration, as I was dealing with sometimes difficult clients that didn’t understand the value of marketing, and I morphed into this different role as an OBM.

I found a couple of people online that were online business managers, and I realized that that matched up really well with my skills and just my past experience, being an account manager, working in a project manager space in the online world, and that I could really create a good edge for myself and my clients, having a background in marketing, and being extremely organized, and knowing how to create systems and processes that would help them be more efficient in their business.

So I took my experience and pivoted a bit when I found the need in the entrepreneurship community for my skillset from the corporate world. It wasn’t clear from the start. I mean, I had to learn and grow from that, and I wouldn’t consider my first business necessarily a failure, because it allowed me to explore and learn in the entrepreneurship space, and just pivot and grow from it. But I didn’t have the marketing agency of my dreams that I had initially set out to have, but it’s allowed me to really diversify my clients and find the joy in what I’m doing now.

As I’ve grown in the OBM space, I’ve also had many times where I’ve had offerings and failed, or realized that maybe I needed a little bit more support and hiring different mentors, and finding the specific clients, the ideal clients that I wanted to work with as I grew as well, and kind of what I became available for. So I truly think that every sort of hardship and point in your business is really just an opportunity to turn it into a lesson that you can truly learn and grow from.

So, for me, if you feeling like you’re struggling, I mean, I take my own advice in this, if you feel like you’re struggling, or you feel like you don’t love necessarily what you do anymore, or you’re just finding what you’re doing isn’t working, I love to just take a step back and ask myself, “What do I enjoy doing? How can I change this? How can I try something new, or where is there another need?”

So I think if you’re experiencing that, or you’re experiencing a point where you feel down or bummed, it’s really just about being creative, and being tenacious, and just continuing to go after what it is that you want to do and figuring it out along the way. I mean, that’s part of life’s journey and it’s what’s amazing about entrepreneurship as well, you can kind of be your own teacher. So you can find me online at, or on Instagram, @katelynehamilton. Thanks.

Megan Minns:

Hi, this is Megan Minns, and I’m a life and business coach for online business owners like you, who are looking to grow and run a scalable, sustainable, and enjoyable online business. I have had a lot of failures in my time since I started my business in 2015, and wow, there are so many different things that have happened that I could share, but when it comes to the biggest event, the biggest decision I made and what could be viewed as a failure that helped me learn and grow so much was actually at the end of 2017.

Because at the end of 2017, I was really frustrated by my business. I had built a business where I had created this brand and expertise around being a tech expert. I was known as the systems guru. I was known for my Asana course. I was just all about tech and running an online business, and that was good and easy for me. But I, at the end of 2017, was really frustrated by my business because even though I had built a successful business, I built one I didn’t enjoy.

I was really trapped mentally at that time because my entire business was built from a place of insecurity. I didn’t feel confident in a single decision I was making. I was constantly comparing myself to other people and I felt really disconnected to what I was even doing, because while I was helping people, I didn’t care about tech at all and I found it really frustrating to support.

With every single client question that came in or inquiry about how to do something very specific on a specific tech platform, I got really frustrated, and that was a really big red flag for me. I shouldn’t be frustrated, supporting my customers. They’re not doing anything wrong by asking me these questions, but I was so frustrated and tired of having to answer these very technical questions and continuously update my trainings to be accurate when a software changed a simple design feature, and I just felt a little lost.

I knew at the end of 2017, I wasn’t happy with the direction of the business and I wanted to shift gears, but I was all over the place as to what that could look like. There were a lot of different options and I didn’t quite feel confident or connected to any of them. So I was really discouraged and disappointed. At the end of 2017, instead of working through that discomfort, making decisions, taking risks, making changes, taking away offers, I ended up taking a full-time job with my favorite client.

Now, we spent over a year together working full-time. I think it was about a year and a half, and I loved the time I spent with her full-time. I’m so grateful for it. I’m proud of everything we accomplished as an employee of her company, and everything we did was such a valuable learning experience for me. But what’s interesting is that I can look back at that decision in 2017 and view it as a failure of myself. Not because anything failed. I mean, I put my business on hold, but it was a failure because I didn’t actually feel confident enough in myself to move through something difficult.

I used that full-time opportunity with my client as an escape route, to not have to deal with all of those concerns, and questions, and frustrations I had. I don’t regret taking the full-time job at all. Like I said, I learned so, so much that I could have only learned in that role. But what I do regret is that I really let myself down. I didn’t believe in myself and I also really bought into the idea that I was just meant to be a behind-the-scenes person. So while that choice to work with my client full-time was a good one, it is also something that I can look back on and know that that decision was ultimately rooted in fear, and doubt, and insecurity.

What was so great about this whole journey, what I learned from it was that I learned, over the next year and a half, how to actually connect with myself, how to truly build real confidence, how to take risks, leaving an incredible job with all the perks and every dream scenario, and I ultimately did take a risk by leaving that full-time job to go back to being a business owner.

So I learned so much, and what I would love for you to take away from this is that wherever you are, whether you’re a side hustler, a full-time entrepreneur, any step of the way, I want you to start really learning to connect with your intuition, and learning how to trust yourself, and making decisions based on just whatever you think feels like the right decision, even if it isn’t the most strategically sound decision. Because that was such an incredible thing for me to learn, that has really changed my life forever. I would love to connect with you, so go to and we can learn more about each other.

Quinn Tempest:

Hi, there. This is Quinn Tempest. I am all-around business strategy, marketing, branding, kind of gal, and the question today is, how have failures in my business helped me learn and grow? Oh, gosh, which failure? There’s so many of them, both personally and professionally. But you know what? I’m the kind of person that, I think we need to learn how to fail.

I think entrepreneurs especially need to get comfortable with failure and get really good at reflecting back on failure after being in the throes of it, and saying, “What was the lesson I learned from that?” because that’s really the only way you can move forward. It’s inevitable that you will fail. It matters more with what you do after the failure.

So, for me, a more fresh failure happened earlier this year. So I have a membership community that I lead, called The Create Your Purpose Collective. It is filled at this point with about 60 women entrepreneurs at all stages of building their business. So a year ago, it was my first time doing it, and I did a beta where I got 30 members into my community, which was amazing.

So six months later, it was time to do another enrollment period and I thought, “Oh, well, I got 30 last time. I can totally get 30 this time.” So I just figured, that’s going to be my goal. But then here’s the problem. I had never launched before, so I first didn’t have a marketing strategy for it, I didn’t even know how to go about it, and then secondly, I was doing so much to upgrade the beta behind the scenes. I was filming the course videos professionally. I was writing scripts for those videos. I was creating the first landing page, because for the beta, I didn’t do anything other than a couple of emails.

I was doing so much behind the scenes that when it came to actually launching and marketing the thing, I didn’t have much energy left. So what happened was, I got 14 new members. Now don’t get me wrong. That was a really great number now, and I got perfect members for my community, but at the time it totally broke me. I had gone into this thinking, “Oh, I’m going to get 30 members. No problem. I got 30 last time.” But I didn’t connect the dots that I didn’t have a strategy. I didn’t have energy or time to talk about what happened, to tell the stories of the beta members. I didn’t approach it correctly.

Truthfully, I took that number 14 personally. I made it a reflection of my self-worth. I thought I was bad at this. I thought I should give up. I thought, why even try if you can’t replicate the same success you had before? I took it personally. Of course, there were other things going on at the same time. I was getting feedback from my beta group, and 99 out of 100 of them said it was amazing, but then there was one or two that just had a negative comment, and that got to me. So it was just, it brought up so many raw parts of myself.

When your livelihood is tied up with your purpose, it’s hard when things don’t work out, and I took it personally. But I’m so thankful that happened because it showed me I needed to breathe more space between my self-worth as a human and my role as an entrepreneur. To know that just because I didn’t hit a goal, which by the way was probably not the right goal to be establishing my first time out, just because I didn’t hit it didn’t mean that I was less worthy or less valuable. It just meant I had some things to learn. It meant I needed to look at how I spent my time better for the next launch. It means I needed actual strategy.

All of these things helped me take action, so I hired a coach to help me come up with a strategy. I even had a launch schedule where I would take care of myself, take baths, bake cupcakes, so that I wasn’t always focused on numbers during the actual launch. So since you’re listening to this, don’t do what I did. Well, actually, do it. Fail. Fail hard. But once you’re out of the throes of it, look back and ask yourself, “What did I learn, and more importantly, what am I going to do next?”

That’s where resiliency is born, and resiliency is the mark of a purpose-driven entrepreneur that’s going to be around for a while. So keep going, look back, ask yourself those hard questions. I know failures can be hard. It’s something I actually share a lot about to my email list. I write a series of emails every Friday called Postcards on Purpose, which have intimate stories from my own failures and lessons. So head to my website,, go down to the footer, and you can subscribe right there if you want to hear about how I’m navigating failures and reflecting back on the lesson that I learned.

Erin Flynn:

Hey, it’s Erin again, and oh my gosh, I loved this episode so much. Hearing how our experts have overcome and learned from failure is just incredible, and I don’t know about you, it makes me feel really motivated to go and try new things that maybe I was afraid of failing at before.

I would also love to hear how you have learned and grown from “failures”, quote, unquote, in your business, so be sure to head to successfullysimple on Instagram and give us your expert take. Can’t wait to get the conversation going over there. See you on Instagram.