Behind the scenes: our hardest business decisions

This post contains affiliate links. Read the full disclosure here.

Subscribe on: Email | YouTube | Apple Podcasts | Stitcher | Spotify | Amazon Music

Making tough decisions is part of running a business. That doesn’t make them any easier! Find out the hardest business decisions our experts have ever made by tuning in to today’s episode!

This season’s experts:

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

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


Erin Flynn:

Hey there, Erin here. One of the things that we all face as business owners are lots and lots of tough decisions, and there’s really no way around them. If you run a business, at some point, you’re going to make really hard decisions. Today, what I wanted to know from our experts was what was their hardest business decision that they’ve ever had to make and how did it turn out? Let’s find out in today’s episode.

Megan Minns:

This is Megan from, and I help online business owners learn how to run their business in a way that is scalable, sustainable, and enjoyable. I think the hardest business decision I’ve ever had to make was deciding to stop selling all of my courses. I would say in particular, when I stopped selling my course, Asana HQ. Asana HQ was probably my most successful course for a lot of my business or for the first few years of my business, I should say. It was all about the project management system, Asana and very in detailed tech tutorials and templates on how to use it.

I feel like that course really helped me establish myself as a systems expert at the beginning of my business, which you’ll notice I no longer am a systems expert. I use systems and I teach systems. Absolutely, they’re a big part of business, but it’s not my niche or focus like it used to be when I first started my business. Asana HQ, I think, really gained a lot of momentum and was my first time having an offer that I felt people knew of the offer, even if they didn’t know of me. I was terrified to stop selling it. I decided at the end, or I guess it was in 2018 when I realized I wanted to stop being known as a tech expert only, I really wanted to have a higher impact on my work and I didn’t want to teach one platform specifically.

I was still selling Asana HQ because it was making sales every day. But every single day that passed, I got less and less excited about those sales, and my course also needed to get updated and updating a tech training course is very time-consuming. Since I knew that wasn’t where I wanted to go, I knew that I eventually needed to stop selling it. I might not have even stopped selling until 2019 now that I think about it. It was a really big decision. I was terrified to do it because it felt like cutting off some guaranteed revenue and making a stance. It felt like a loss of an established brand that people knew about.

But I ended up doing it and I’m so glad I did. I have no regrets. From the moment I stopped selling it, I was glad I did it. I knew it was the right decision and it really opened me up. I actually ended up having a dear friend of mine who loves teaching tech tutorials. She created an Asana course, and it was so great to be able to actually support her and I still support her. Her name is Louise Henry. She has an incredible course called Uplevel with Asana. It’s been so much fun to not be the one teaching and instead of being able to point people into a resource that’s so helpful for them. So you can still go to and learn more about her course, even though it’s not called Asana HQ.

So I have no regrets because it’s allowed me to be able to refer people to someone else who loves teaching, loves creating new resources for this. There’s so much more positive energy around that offer that I think it’s really a better experience for people in the long run to have a teacher like that. For me, it meant that I really made the decision. I upleveled when I stopped selling that course, because it allowed me to truly accept the shift I was making in my business to doing higher level work with business owners like I do in my program Empowered CEO now.

It was difficult. I’m so glad I did it. I have no regrets. So for you, if there’s something that you’re currently selling that’s making some money and it’s really difficult to let go of, or even if it’s not bringing in consistent sales, just feels like this legacy thing that’s hard to let go of, I would love to encourage you to take the risk and stop selling it. Because if it is out of alignment and you aren’t releasing it yet, it is still going to hold you back. It’s going to slow you down. It’s going to make you question everything and it’s going to prevent you from truly stepping into the next level of your business that you are ready to step into.I hope that that was helpful and I would love to connect with you on Instagram. My handle is Megan_minns. So hopefully I see you over there.

Quinn Tempest:

Hey everybody. This is Quinn Tempest. I am the founder of Create Your Purpose, and a color loving, urbanist out here in downtown Phoenix. What was the hardest business decision I’ve ever made and how did it turn out? Well, let me tell you, it was really difficult and I was scared about how it turned out, but looking back now, because it was about three years ago, it was the best decision I’ve ever made. So to give you a little background, for five years out of the 10 years I’ve been on my own as an entrepreneur, I had a really big client. They took up more than half my time and gave me more than half my income. Multiple times during that five years, they asked me to go full-time. Actually, it became almost a running joke that it was about every eight months I would get the ask and I always said no, because I always still wanted to build my own business.

But as a budding entrepreneur, as a newer person in business, the stability and the income of this big retainer client was just too good to pass up. It freed me up to get creative, to work with clients that really lit me up outside of that one client. I’m really thankful that I pursued that. But it got to a point and it was a very specific point, it was right after our honeymoon. We got married about, my husband and I, well obviously, three and a half years ago. So we went on a honeymoon and almost to the day we got back, the decision seemed to made for me. I knew I wasn’t happy anymore. I knew I was dragging myself to my computer every morning and I needed to make a hard decision, do I go full-time with this role and really grow into it? Because honestly they were giving me lots of opportunities.

I was speaking on stages all across the country. I had the opportunity to really build up my significance in the content marketing world. But it wasn’t really what I wanted. Inside of me, I always knew I was an entrepreneur. So it was between going full-time in this role or creating something of my own and that’s the direction I went. But from the moment we got back from that honeymoon and I made the decision that I needed to make a change to the actual moment where I left, it probably took about a good six to seven months and that was a hard transition. It was hard because I was giving away so much money. I was giving away stability. I was giving away opportunity for something that I didn’t even know what it was yet. I just knew I wanted to create something and I didn’t know what that was.

So what I had to do was plan. I created a financial plan. I started saving money. I talked to my husband about how we were going to make it work, because it wasn’t just leaving that client in the next six, seven months. It was replacing that income after that. Also, then creating the thing that was on my mind that I didn’t even know what it was yet. It was a long, long journey. There were trade-offs. There were heartaches. There were lots of regret even. There were lots of times where I wasn’t sure if I was making the right decision. But now looking back, I always think of this quote actually from Steve Jobs from Apple, he said, “You can’t connect the dots looking forward. You can only connect them looking backwards.”

So at the time, I didn’t know how my dots can connect. I didn’t know if it was even a good sound decision, but looking back now I can connect those dots. Now, that I see that that decision paved the way for me to ask myself hard questions. What is the legacy I want to leave? What is the life I want to live? What is the impact that I want to make through my business? Three and a half years later, I know exactly what that is. I’m now an owner of a trademark which is kind of crazy. I am so happy in what I’ve built and what I am yet to build. So just know that hard decisions and transition periods like those, like that I went through that you might be going through now, they are so worth it.

You might not know it in the moment, but you will when you look back and that is the power of entrepreneurship to create your own path and learn from the lessons of hard decisions. I’d love to keep connecting with you on this. Feel free. Come find me I’m over on Instagram, almost daily. So come over. I am at Quinn.tempest. Send me a DM and let me know what one hard decision you made was. I’m super curious to find out.

Alisha Robertson:

I’m Alisha Robertson, founder of and business coach, where I help women entrepreneurs to build a successful business without sacrificing the life that they desire. So the hardest business decision that I have ever had to make was completely shutting down my one-on-one coaching business. I had been doing it for years. It was going great. I was making good money, but I was so completely burnt out to the point where I was resenting my clients. I was tired. I thought that maybe I needed a break so I would take a break and then I would come back and I would still feeling the same way.

I really just got to a point where I realized I was burnt out. I was building this business that had gotten so far off from the path of what I really wanted out of my brand. Most of my days were so consumed with either on client calls or doing client work, prepping to get to clients that there was just no more joy in my business. Even though I love coaching and I had incredible clients, I always just felt something was missing and I was burnt out. I was tired. I did not want to get out of bed in the morning. I was done. So the hardest decision that I have had to make was shutting down what was working in order to build up something that I didn’t even know what it would be at the time.

Not to mention, I had also around this time found that I was pregnant. So being pregnant, expecting this new human come into my life, completely cutting off my main source of income was terrifying, and honestly, a bit crazy now that I think about it. But it allowed me the free space to really dream and dream big and really kind of reconnect with what I wanted out of my own brand. Out of that, I have been able to build my company, Living Over Existing, where I’m helping women to yes, build a successful business, but I’m also helping them to really get to the root of what they want out of their business. I’m helping them to get clear on what their non-negotiables are so that when they’re taking on clients, that they’re not stressed out like I was, or they’re not completely overwhelmed like I was, and that they’re actually able to go out and live the life that they want while still building this incredible business.

So definitely shutting down my main income stream around the same time that I found that I was pregnant was the hardest decision I’ve ever had to do. But so much beauty has come out of taking that leap of faith. I think that’s what it is. You just have to have that leap of faith and go into it with a plan, and just with all hope that this thing will have to work and also know that you can go back. If Living Over Existing wouldn’t have worked, I could have easily gone back to one-on-one coaching. You can always go back. I think that’s one thing that a lot of us forget when we make these decisions. You can always go back. You can always start over. You can always ask for a redo. All right, you guys, I hope that was super helpful. If you would like to learn more about me and what I do through my company Living Over Existing, you can head over to

Jordan Gill:

Hi, Jordan Gill from Systems Saved Me. I think the hardest business decision I had to make was determining if I was going to hire employees versus contractors, because the word employee sounds really intense and there’s a level of commitment that goes into it. If you just send the contractor money, then they’re in charge of their taxes, all that stuff. When you have employees, you have to think about their taxes, you have to think about benefits, all of us sort of stuff. However, when I started to actually think, my business is going to be here longterm, I want people on my team who are also going to be here long-term and sustained with me, then I need to make that adjustment and it has been phenomenal.

To know that my team is as committed to my business as I am for the long run feels amazing and makes me feel like we are going to do really big things together without having to worry about do they have a big client load or one of their client’s launching so then therefore I can’t launch then, or just things like that that you have to think about when you hire contractors. It’s not to say that I don’t have any contractors in my business. I do have a few, but I’ve had conversations with them. When I’m ready to make the leap to employ with them, then they’re willing to take that leap with me, which is pretty dang awesome.

It was a hard, hard business decision because it’s a commitment and not every contractor wants to then become an employee. But for me, I think that how I have my business set up is attractive to entrepreneurial-minded business owners because it’s less structured as most companies are, I would say. So if you want to find resources or connect with me, then go to or find me on Instagram at Systems Saved Me.

Katelyn Hamilton:

Hi, this is Katelyn Hamilton, and I’m an online business manager helping you go from overwhelmed to out in front. The hardest business decision that I’ve had to make in my business is honesty letting go of clients that I love, clients that I love in terms of their personality, who they are. I mean, I really strongly adore all of my clients and build relationships with them outside of just the business world. I am a cheerleader for them. I love getting to know them on a personal level as well and I think that’s a really important in order to just kind of have that trust in your business.

When the time comes for me to let go of a client, whether that be that it’s just not in alignment for me anymore in terms of what they need from me, or in terms of that the work that we’re doing, or, for example, I’ve increased my minimum number of hours as I’ve scaled my business in order to really serve my clients well, but not have a crazy amount of clients or number of clients I’m working with at one time so I can be really present and proactive in my client’s businesses, sometimes that’s led to me having to let go of a client just because we were no longer in alignment in terms of how we needed to work and the support that we needed from each other.

That’s hard for me because I am a recovering people pleaser. I hate letting people down. It’s hard for me to kind of also walk away from that income, right? If you’re doing that, you’re giving yourself the opportunity to create space in your business and let the right clients, your ideal clients flow into you. That always happens no matter how scary it can be. When you let go of what’s no longer serving you, the right clients do show up. There is usually a small break in that. But that can be really hard to do. So I think that’s the hardest thing for me I find in my business is letting go of those clients that I love.

But at the same time, knowing that it is for the best for both of us, that we can both be served and serve in a way that is needed for us to be successful. If you are interested in staying connected with me, you can follow me on Instagram at Katelyne, K-A-T-E-L-Y-N-E, Hamilton. Or you can go to my website at

Erin Flynn:

Hey, it’s Erin again. Now that we’ve heard from our experts, I want to hear your expert take as well. Head over to Instagram, find us at Successfully Simple and let us know what your hardest business decision was and how it turned out for you. I’ll see you on the Gram.