My Favourite Failure: Balancing Parenthood and Entrepreneurship - Alyson Caffrey

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1:05We were in this really strange fog around what was possible because we didn't know what we were doing becoming parents. We had, you know, reconciled with the fact that, you know, Steve was also losing his income in October. So I was going to become the sole provider for our family and become the sole provider of benefits for our family. And so it was a lot all at once and it all needed to happen pretty quickly as soon as our son was born. Alison Caffrey is the founder of Operations Agency, an operations consulting firm. The business today is buzzing, but she came within a whisker of throwing in the towel.

1:41Despite being an operations expert, she'd failed to plan for having her first child. Combined with a few other factors, her personal life collided with her professional life at just the wrong time and turned into the perfect storm.

2:04In 2019, Alison's business was working as a fractional COO, providing COO services on a part-time basis for companies that didn't need someone full-time. Then, some happy news. We found out that we were pregnant with our first son in December of 2019. and we were so overcome with excitement that a lot of our focus went toward really preparing to become parents and preparing our home around that. And I foolishly thought transparently that I would figure it out because I'd figured out almost every other operational obstacle. We'd had key players go out on maternity leave in the companies that I was helping manage at the time.

2:52And I figured that I would just kind of take everything in stride. At the same time that we found out that we were pregnant with our first son, my husband was pulled out on a deployment and was basically sent over to Afghanistan and finished out his army career in that way and came back in March of 2020. And then we had our son in August of 2020. And the sequence of events there was my business at the time was me and a handful of contractors. I was in a position where I hadn't basically prepared anything for my leave. A lot of what I was charging for was my time. And my husband lost his benefits going through the military.

3:42So my company at the time had to take on the weight of being now the sole income provider, had to provide benefits for us and our growing family. And all of it at once with no preparation almost led to me shutting it down and going and getting a full-time job as a COO somewhere. After giving birth, the reality of her new life smacked Allison around the chops. Yeah. So I had my son just after midnight on August the 30th. and we got moved into the room that we were going to spend the night in around 4 or 5 a.m. And I knew that my team had already started working. It was a Thursday morning and I had this picture taken of me and my firstborn son.

4:30I was holding him in my arms. I was still like, my hair was still crazy messy from just having given birth. And frankly, I was happy that it was over, but I was so excited to finally hold our son. He's sleeping in the photo that was taken. And in the next frame, the one that thankfully my husband did not capture was me setting our sleeping son in the bassinet in the bed beside us and picking up my phone to start answering Slack messages and letting our clients know that I wasn't going to be meeting with them that day. So it was a harsh reality from the very first few hours of being a parent. It was a harsh reality that I hadn't built a business.

5:14I just found a way to create another job for myself. So losing everything pretty much overnight when my son was born really showed me that, frankly, I didn't really have the business that I thought I'd had. I had a really incredible freelancing opportunity, you know, a handful of clients, although I had a technical business that I paid myself through, the structure of it all was really reliant on my time. And that first hit over the head in the hospital, honestly, it made me feel like I was a bad mom. It made me feel like I was starting off this relationship with my son in a way that I knew I didn't want.

5:55And what happened the days after I went home from the hospital two days later or so. And I was back in client meetings before the end of the following week. Brutal. And the pressure cooker just kept cooking. I remember in the first few months, so we were really reconciling with a lot of the challenges that were happening in the business. And I really did feel like I needed to start my business over from scratch, really reconciling with the fact that I didn't have the business I thought I had, that it couldn't provide for my family the way that I thought it could. Honestly, I felt like a gigantic failure.

6:36I felt like I had wasted time, three years of time, building this thing that now almost couldn't serve me in this next phase. And I couldn't really quite figure out how to even continue generating income, continue serving clients in a way that felt a little bit more scalable, I guess. And it was really, really tough for me to kind of try to solve all of these problems. It seemed like all at once. So I did the worst thing that I could have done, which was avoid it pretty significantly. I blamed a lot of the issues on becoming a new mom and the hormones that roll in with that. And don't get me wrong, they are challenging, but I really hid there.

7:23I hid in the fact that becoming a new mom was a challenge and I couldn't actually figure it out. And that was one of the big things that led me to considering shutting down my business, considering that I had failed, considering that I wasn't going to support clients anymore and that I was going to start updating my resume, as they say. And I remember specifically, there was a time where I was breastfeeding my son and breastfeeding in and of itself is one of the hardest parts of becoming a new parent and just dealing with every schedule and every demand and all of those things. It's really taxing on your body.

8:01It's really taxing on your mind. And I wasn't producing enough milk, I remember, one day for my son. And I'm reading all these articles and thinking about how I can increase my milk production. And something that I read that day was that having a yeasty beer would help you, would help you increase your milk production. And honestly, I used that as an excuse for the next few months to start to drink a beer at about two o 'clock in the afternoon. And I'll say, reflecting back, I knew that it was the wrong thing to do. I knew that I was avoiding and using alcohol to dull a lot of the challenges and a lot of the pain that we were experiencing as a family that I was experiencing as a business owner.

8:49And I used it as a big excuse to tie one on at two o 'clock in the afternoon. I would have two beers. I'm a small person. So that was all it really took. And especially becoming a new mom, it was just the wrong way that I wanted to approach my relationship with my son. It was the wrong way to tackle some of those later stage tasks that I needed to get done inside of my business. And I wasn't showing up to client calls drunk, but I mean, listen, it was almost that bad. And I look back at that time and I think about how much I had felt like I was giving up. I thought about how hard it was going to be to rebuild.

9:36And I was almost in a grieving, you know, a grieving state from what I, what I had made and just realizing that what had gotten me to, you know, success right to that point, wasn't going to get me to the next stage, which was really creating something that could function without, without me being there. Something that actually didn't depend on whether or not I needed to step away and breastfeed my son or whether or not when he got older, I wanted to attend one of his basketball or soccer games or be there for any major point in his upbringing. And I think reconciling with that at that time, it led me to make a lot of bad decisions in the grieving process of my business and really feeling again, like I'd really failed.

10:24I wondered, what did her husband make of all of this? So my husband was also going through some challenges of his own. As I mentioned, he'd just returned from Afghanistan a few months prior and he was exiting the military. So he and I were kind of co-creating this space together where it was kind of okay to just neglect our responsibilities for a second. I'm not proudest of that moment in our relationship. And I think that there was a time where he and I were really in a position where we were struggling to become new parents. As you remember, the landscape of the world in 2020 was also a huge challenge for many, many families.

11:10And folks were losing jobs. They were losing careers, losing businesses. They were moving from their families, big relationship strife, political strife, lots and lots of strange climate to that year. And we felt more disconnected than ever from our friends, from our family, from anyone that we were around. We were living just outside of Nashville at the time and in a place where the Army had brought us, but we had no family. And so the two of us together were kind of grieving in this way. I was really stressed about the business. He was really stressed about what the next phase of his life was going to look like and his career was going to look like.

11:56And so we co-created this reason together to just shut out all of the responsibilities. He would very frequently join me in my afternoon beers. And it was something that I think we both really look back on now and consider that to be one of the biggest missteps in the two of us growing our life together. But sorted out they did, with Alison turning the ship of her business around. But there wasn't a clear moment when she decided she was going to make it work. Yeah, I mean, I think a lot of us are conditioned to believe that before and after is this very stark difference, you know, a moment in time or something like that.

12:36But ultimately, I was digging out of a lot of the issues that we'd had. And a lot of the reasons why I was thinking of stopping working for myself and shutting down the business that I'd currently built. And that continued for a long time. I almost shut down the business in October of 2020, but that thought remained in my mind for almost another year afterward and continued to sprinkle in during hard seasons in the years to follow. And it's really, really challenging to kind of cut that belief out of your mind. Once you've faced failure, once you've lost a business or lost a job or lost an opportunity, lost a family member, it's really hard to get that out of your brain as a potential possibility.

13:21And it also affects how you approach other things. I do think that my almost failure in my business, and to be totally transparent, the way that I personally feel that this went down is I did create almost a brand new business from scratch at that point. So although the business name survived and the entity lived, I basically gutted everything that we were doing and changed everything about how we operated, everything about the way we served, everything about the target market that we were approaching. And I do feel like that was maybe not a formal failure, but it was a complete reinvention in the sense that there are only a handful of things that we do now that we did back then.

14:11So how did she create this new business? Well, first of all, she started offering scalable things that weren't tied to her time. And then she focused. So not only was I working myself to the bone and working 70, 80-hour work weeks before I had my son and then in those early months, but I was in a position where I was spanned across multiple different markets. So one of the biggest things I asked myself is what is the thing we're best in the world at and how can I offer that to only one specific type of business? And so creating a niche, and I know that this is something that is widely, widely accepted in a small business space, is that creating a niche is going to really simplify the way that you do a lot of things.

14:55And I think one of the biggest misses I had early on in business is that I went way too wide. If the money was green, I said yes. And that's not actually what's going to serve us long term. So I started getting really clear on what I wanted. I started getting really, really strict with who I helped and how I helped them. And it really did create this magnet in my business. People were excited to work with me. People were excited to support me, whether that was a team perspective or a partner perspective. They were like, wow, I have an audience that's really similar. So people started raising their hands to support me instead of me going out and hunting for a new business and knocking on people's doors and adding more hours to the list of things that I had to do.

15:38Instead, I was able to give folks the gifts of templates and trainings and things that they could replicate. And that became one of the foundational ways that I started serving moving forward. Behind the scenes in the business, I really started focusing on making sure that our profit was very in line with some of the things that we needed to afford for me as an employee and also any future employees that we have. We have a very, very specific way that we hire now and we create budgets for people that we hire to include things like health benefits, to include things like profit sharing. And that to me was invaluable.

16:14I started asking myself the question, if I were to go look for a job right now and I saw operations agency on a job posting, would I want to work for this company? And I started asking what would need to be true about my company for me to be really, really excited to be an employee there, right? What would I want as an employee? That was Alison Caffrey. Thanks for listening to this episode. I've been your host, Dan Murray-Surter. We'll see you next time. If you enjoyed this episode and found it useful, please write us a review and subscribe wherever you listen to your podcast. It makes a real difference.

16:49And we genuinely love reading what you think. We read every single review. I've been your host, Dan Murray-Surter. And we'll be back next week with more lessons for entrepreneurs and leaders. See you next time.