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Software Social

A Conversation with Rosie Sherry

Oct 26, 2021
39:12

Follow Rosie! https://twitter.com/rosiesherry
Check out Rosieland: https://rosie.land/

Michele Hansen  0:01 
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Hey, welcome back to software social. I am so excited this week to have with us the woman the myth, the legend, Rosie Sherry. Hello. So excited to have you. So you were I founder of Ministry of Testing, lead community at Indie Hackers, which is probably how many people listening know you, currently leading community for Orbit. Also have your own thing going on Rosieland, which is a community about community. So excited to talk to you.

Rosie Sherry  1:30  
Thank you, thank you. It's good to be here.

Michele Hansen  1:33  
So I want I want to start out with something something I noticed when I think about your background is how you've kind of gone between being a founder yourself, and intentionally working for other people also having sort of other things going on. And, you know, on the show in the past, we've kind of talked a little bit about how sometimes there's this perception that there's this sort of like staircase of an entrepreneurs career where you start out working for other people, and then maybe you have an info product, and then maybe you do consulting, and then you do an info product, and then you have a SAS and then I don't know, and it's like this sort of like staircase. And there's this sort of like implied increase in virtue throughout all of that. And then if you're taking backwards steps, that's seen as like, literally like a step backwards. And it's like this ladder rather than being this kind of what I'm more see in people's actual careers, which is kind of moving between different things as their interests lead them and as their life leads them. I feel like I see that in your career. And I'm kind of curious how you think about these shifts you've made between working for yourself and working for other people? And like, like, kind of all of that.

Rosie Sherry  2:45  
Yeah, it's kind of like steps going up and down, right? Or going up and down or left, I guess, an elevator? Yeah, I mean, I have like, no idea what I'm doing. But I guess like, I kind of go with the flow. When I when I stepped back from Ministry of testing, I had been doing that for 10 years. And I thought, like, as I was stepping back, I thought I'd never work for someone else's, like my plan was to take some time off and just like, take it easy for it. And just, I don't know, see what I wanted to do. And I knew I kind of wanted to, like focus in on community, but I wasn't sure how. And then, like, the opportunity with indie hackers came up. And I was like, Oh, you know, this could be fun. This could be interesting. I think I could learn a lot from how courtland has built community there. It's similar to ministry testing, in some ways, but yet, it's, it's really different. So I kind of just jumped on that, like, you know, earlier, earlier than I had planned. I was I was a contractor there for the whole time. And I was there for two years as a contractor. And basically, we just kept renewing the contract, like every three to six months. So it wasn't like it was the plan, stay there. And apparently surprised that I stayed there for two years, I thought I wouldn't last I thought I wouldn't be able to kind of work for someone else after like doing my own thing for 10 years. That was interesting. There's a lot of benefit, especially, I think, perhaps more these days where everything just seems I just feel like there's so much opportunity out there. And there's a lot of things that I didn't like about running a business. I didn't necessarily want to manage people, I didn't want to do the accounts, I didn't want to worry about money or worry about, you know, the future of, of the business. So yeah, I mean, this, you know, loads of things about running a business that I think people try to glorify, they try to hide, they try to not talk about it. But you know, it can be stressful. And I think my realization after running the Ministry of testing, is actually I don't, I don't want to run a company and employ people. I don't want to be responsible for someone's wages at the point of life that I that I am in at the moment. might might change over time, but right now Yeah, I'd rather like I guess, do something more for me something more, you know, focusing on, like my interest in things that that I need. And yeah, and I guess like contracting, bringing home a paycheck, that's great. But you know, for me, it's been, you know, it was great, I saved up a bunch of money, I didn't actually spend any of the money that I made in the hackers. So that was like a nice, consistent income for me to like, you know, get our family more and more of a safety net. Now, my Uber and I never, ever considered working for a startup people have it. Yeah, it's, it's new. For me, it's different from me. But this negative, there's a lot of pros as well. So I try to kind of be mindful of all of that. And, you know, there's days, I just want to pack it all in and say, I can't be bothered, I should just go back to being independent. But there are other days where I'm just like, no, this is actually really good. I'm enjoying what I'm doing this, you know, there's a great team that I'm working with. And again, you know, I get paid well, I don't have to worry about money, I don't have to invoice people the money every month in my bank account. And I'm like, Oh, this is nice. This is, you know, this nice not just to show up and do the work.

Michele Hansen  6:11  
You mentioned how it was stressful, being responsible for people's paychecks. And I totally relate to that. I think it's one of the reasons why we haven't really, you know, formally hired here, right? Like, I have a VA, but you strike me as someone who you know, and this comes through so much in your work for indie hackers in your work on community who like deeply cares about other people, and supporting them and encouraging them and helping them reach their goals, and you know, and be that person they want to be. And I wonder if that almost made it harder to be running a company and responsible for people's income when you felt so responsible for those outcomes and really invested in them as people?

Rosie Sherry  6:57  
Yeah, I mean, it's actually interesting, because I still own in ministry, testing, or co owner, when you're founded, you kind of like, I guess, the foundation of everything that comes later, to a certain extent. So like, the fact that I worked when I wanted, the fact that I had five kids, the fact that I just like took time off when I needed to the fact that I defined, you know, decided my own hours, all of those things, ended up becoming how things were done administrator testing, and it's become more apparent, I guess, as the team, I think about eight or nine people at the moment, at first, you know, I was only one with kids. And, you know, I was very much family friendly person, I would support, you know, everything about me is like, we need to live our own lives as well. We need to have flexibility, you know, work shouldn't stop us having having a family and ...

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