A Conversation with Rosie Sherry

Michele chats with Rosie Sherry, founder of Ministry of Testing, mama bear of indie hackers (used to be upper case, now lower case), creator of Rosieland, and community lead at Orbit.

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 doing things that we want to do. And at first, it was like, just me it was kids. But then like, as the years have gone, I think last year, there were three new babies born within the company, and as a team with like nine people that's like, oh, wow, how are we gonna manage this as like, as a company, even though it's not my responsibility anymore. There's a CEO running it. But he very much took on the philosophy of like, well, this is how Rosie has always done it. So this is what everybody else gets to do as well. So we let the mothers choose what they want to do. We let them you know, take the time off that they need to take time off, and have a say, and there's no there's no judgment for any of it. And we listen, and we care and we try to make good decisions, even even if it costs us money, right. And like, as a small company, and you have three of your people off on maternity leave is a big kind of hit. But it's not something that feels wrong, it very much feels right and like allowing everybody just to choose the time that they have off and pay in the world. And you know, making sure that they get a fair deal when they're often on maternity leave is to me, you know, I couldn't do it any other way. Because it would feel hypocritical. And for me, it's just like, I can't have once that rule to me and like different set of rules for For everyone else, even if I never took maternity leave properly. I believe like, you know, everybody else should have had that right to do that. I guess.

Michele Hansen  9:20  
It sounds like a bit like Golden Rule management, like treating others as how you would want to be treated.

Rosie Sherry  9:26  
Yeah, I don't understand why companies can't do that. can't comprehend it. And it's probably why I haven't. It took me I guess it's probably why it took me a long time to actually end up working for other people. Because without listen to the pandemic, because just like nobody was truly flexible enough in their thinking about how people showed up for work. And I've been working from home all this time on my own rolls, and then the pandemic comes along and I'm just like, still working the same way that I was working before. This ain't nothing changed for me day to day, but for everyone else. Or, you know, like a huge majority of people, life change and companies rethought their processes and what was acceptable and what wasn't acceptable. And the fact that we can all work from home now I think is is great, but at the same time is unlike Well, why couldn't we do this before we could have. But companies, you know, I guess like it wasn't urgent enough to think of our needs until the pandemic came along.

Michele Hansen  10:26  
And, you know, you mentioned how your life didn't change all that much with the pandemic. Yeah, I want to detour for a second because I understand that so you have five children, and you unschool them and it would just be interesting for a moment just to talk about not only what does that look like but also you know, you mentioned your whole life didn't change much. And I'm kind of curious what does that home life look like between you and your husband with this sort of unschooling elements layering on top of also like your, your work life? Like how does all of that work together?

Rosie Sherry  11:02  
Yeah, it's tough. I think like unschooling, I think the toughest part about unschooling, I think is, or even homeschooling is about making that kind of adjustment to life, like trying to instead of like, you know, if if kids go to school, you know, you have the six, eight hour block of time to kind of get work done and you can plan things around that with unschooling is like, well, you kind of have to plan for your kids. And then you have to plan your work around your kids, and you have to juggle things. With me, it's with my husband, we like have equal share on like, the kids in the house. And I just think that's the hardest part is like most people, probably, I guess I feel I feel privileged to be able to do that at the moment. But like, I guess, like, the thing I do is like, we're having this chat for me, it's in the morning. And that's like, not my normal schedule. So the like, normally like I'm online from midday till eight, and I'm with my kids from when they wake up until midday. And then at midday, me my husband swapped over. And that's those are the, that's the deal we have right now, to make things work. And so, in the morning, I would normally take my kids to a class that they have or a group that they go to, and it works, I guess, to try and to split that time, it changes all the time as as my work changes, or as my husband's work changes, we find ways to adapt and I guess that's the magic of unschooling, I guess like unschooling is like, we're always, I guess, we're always looking for things that our kids want to do to keep them active. So every day, especially our younger ones, who are between the age of three and 10. You know, getting them out out the house once a day is like basically our goal. And that happens in different ways at the moment, except for school, beach school, art class, sports, or football. And then other days that we hire, or we pay a friend to take them out for the day. She's like a single mom, and appreciates extra bit bit of income. It's tough, it really is tough. And it's like we have to say no to things a lot of the time, but I think at the same time, I think like the pandemic has kind of worked in my favor as well. Now that everyone's online, I feel like what's the right word? I guess previous to the pandemic, I felt like I was only one needing to have the flexibility. But I think like these days, it's it's more more acceptable. I guess, everyone's more accommodating, like having kids in the background is okay. Pre pandemic, that was not okay. You know, stuff like that, you know, despite COVID I appreciate how the world has changed. We feel it feels weird. I don't know. What do you think it feels? It feels weird to? Yeah, to say that. But I think you know, actually, there's been positives from COVID.

Michele Hansen  13:57  
I think it's forced us to reevaluate things and maybe shifts that were happening very slowly, like you mentioned, you know, more work from home and maybe more flexibility shifts that were happening very, very slowly, or only in very specific corners of the economy were kind of thrust on everyone all at once, which was both traumatic and also sped up things that needed to happen to at the same time at great cost to everyone involved, Beto as you said, like, you know that it's acceptable to have children in the background or even a dog barking, like I remember two years ago, you know, before COVID, and I was having a call and my dog barked in the back because the mailman was there or whatever. Like, I always felt so embarrassed on the call. And, you know, I remember sometimes, you know, the people, you know, whoever I was having a, you know, customers having call with, or one of them being like, Oh yeah, you know, we have a dog friendly office too. And I was just like, Yeah, like, dog friendly office, you know, that whole thing of like being a really small company and not wanting? Yes, I'm actually like working from home like that being kind of like something to be sheepish about, you know, like that you were working from home because it was like, What? Like, can you not afford an office? Are you not legit enough to have an office? Like, do you not like it used to prompt so many questions, most of them not very, like, positively reflecting on the company. But then all of a sudden, you know, so many of us, you know, who were lucky enough to be working from home, everybody was working from home, everybody, you know, had kids in the background dogs in the background cats on their keyboard, like, you know, and we all just had to learn how to be a little bit more understanding with one another.

Rosie Sherry  15:41  
Well, human right, I think like, we, we've learnt to appreciate and see that we all live in different circumstances, and we should adapt to that, and we should make sure it's okay. You know, almost like, I guess, like, the whole diversity movement, I guess, in the past few years is, you know, crept up. And, you know, to me, this is also like, part of it is like, we're all human, we're all people, we have different circumstances, that the sooner we can make that, okay for everyone to just like, be who they are opt in, opt out things, be able to, you know, not have shame for, for whatever it might be, I think like, the better the quicker, we can just like, move on and like, kind of focus on our work and get and get things done.

Michele Hansen  16:38  
Using shame, just there kind of reminded me of what we sort of started this conversation with, which is, you know, in your career, you have sort of intentionally and consciously moved between contracting and, and being a founder and working for other people. And when people come to a situation where they realize that maybe consulting isn't working for them, or they're trying to get their own SAS off the ground, and it's not working, and the finances are tight, and they're thinking about, you know, going out and getting a job. Yeah, it seems like people often feel a lot of shame around that. And then that feels like failure to them. And I think what your story shows that, you know, it's not linear. And, and I'm just kind of curious what you would say to someone who is kind of maybe at that point, who is wondering, you know, just, you know, that thing, things aren't, things aren't working, or the finances aren't there. And they've they've got to go back and, you know, get a job, like, what would you say to them?

Rosie Sherry  17:56  
I definitely felt this, like in the indie in the indie world, like, being immersed in that world. And, you know, people want to make it they want to be full time, indie hackers. And it almost becomes, like, a thing of like, what if you're not a full time indie hacker, then, like, you know, you're not a success really are there's only one way. And, you know, I almost, you know, thought that, you know, I thought even just like working in India, because I thought I wouldn't last I thought, you know, people, you know, I wouldn't make an impact. I wouldn't enjoy working with courtland, or all that kind of stuff. And even even when I joined indie hackers, the opportunity came up as a result of courtland looking for some social media help. And I was just like, at that point, I was just looking for something else to do. And like when I reached out to him, he was like, Yeah, but you're overqualified for this. I was like, Yeah, I know. But I'm, you know, I'm still like, yeah, I could do it. And, you know, I, I personally felt like I could learn from indie hackers. And that role ended up being more like of a community manager community lead role that he that he offered me. But did I feel shame, like doing that a little bit, but at the same time, as I, it doesn't matter, you know, I need to, you know, I really wanted just to have an excuse to do something else. And so yeah, I work for CEO, founder to social media and community manager, which is a step back, right? You know, on paper, it's a step back. But actually what it did for me was was huge, is like, before I joined India, because no one in the indie world really knew who I was. There's a few people here in there. But what it did for me was was massive. So I say I think a lot of the time choices, I guess, perhaps is that it's not all about money. It's not all about job titles. And we can dismiss job titles is not important. That's, you know, I think sometimes they can be but I think I think, if we think about, or like, the way I think about it is like, well, I want to do stuff, I want to learn stuff, and I want to work on things I care about. And does it matter if it's starting your own thing? or working for someone else? I don't think it really does. I think, at least for me, it's like, you know, five, finding, finding the right people to work with is, is key. And yeah, I mean, there's a lot of jobs that I'm sure would be sucky. And I see I definitely see people struggle, working for companies and being like, part indie part, like, working for companies. So yeah, I don't think like anything is necessarily Perfect. Perfect solution. But I guess it's like more about like, finding your fit what's right for you? How do you get to do the work that you do? Enjoy? How are you growing personally? And, like all, but I think I'm growing a lot personally. And also in, in my, I guess, desire to kind of impact the community world, I think I'm doing that. And I get access to stuff that I wouldn't, if I was trying to do all, all of that kind of stuff on my own. So yeah, there's definitely like, the pros and cons. So yeah, but but it's easy to think because when I joined, obey, it was at the back of my mind is that oh, my God, what will people think? I've been indie for, for 15 years. You know, should I actually take this job? Is it is it in conflict with, with who I am? Those are all that was definitely in the back of my mind, I can't, I won't lie about that. Yeah, I was nervous about announcing that. I'm not sure what people would think. But I think, at the end of the day is like, I'm still sticking to, to who I am, I'm still sticking to my values, I'm still pushing for the things that are important to me in all of it. And if I don't get those, and it's going to become a problem. You know, say, I'm still being me, in every, every space that I show up. And, and that's what's important to me, is that, and if I can't get that, then that's where it becomes a problem. For me, I think, Patrick, my boss,

Michele Hansen  22:52  
I noticed that you just said how you had this conflict around identity. And I feel like that's running undercurrent of a lot of time when people are having this struggle, is identifying as a founder, and all of the things that come with it, identifying as an indie hacker, identifying as someone who, you know, runs their own things and whatnot, and shifting identity into something else into, into, you know, who am I if I am not somebody who runs their own company? What does that say about me? Just who am I as as a person, I think in a world where we wrap up so much of our identity and what we do for work. That's a, that's a massive and can be quite a, you know, debilitating sort of shift and psychological process to go through. And yet what I also heard you say several times throughout the, the conversation is a reason why you took the job with indie hackers, or the contract with indie hackers, is because you wanted to learn and, and I wonder if that transition is a little bit smoother. When you think of, you know, there's you have this identity as an indie hacker, as a founder, you also have an identity as someone who likes to do other things. And one of those, I think, for you that really comes through is somebody who's curious, and who likes to learn and letting another identity almost kind of supplant that, that founder, one that's sort of, you know, taking a backseat.

Rosie Sherry  24:40  
Yeah, it's interesting. It actually brings me back to like minister testing and like when I stepped back, it was like, Oh my god, like, Who am I? Who am I going to be now I've been this testing person, this person, leading the testing community for so long. I'm almost leaving behind. And much of that, obviously they I still keep in touch with people, but I'm not in that world anymore. Yeah, it was, it was hard, it's hard to shift away from that and to figure out how to how to kind of redefine your life and who you want to be. And how do you get people to, I guess, to see that to know that and, and yeah, it's, it's tough and I guess like, right now with the indie stuff like, you know, I do Rosi land stuff on the side. But even that, I feel like oh, you know, I see a lot of the indie stuff happening, I still keep an eye on indie hackers. But, you know, at the same time I miss in the hacking as well, I don't do nearly as much as I would love. And, you know, I struggle with that. So it's like, how much of these different people can I be? How do I? How do I separate that? Do I need to separate that? And I mean, I was I was employed over it was no full well, knowing that I had all this stuff on the side. And that that had to continue to exist when I joined over it. But yeah, I feel like I definitely feel less a part of the indie world. Because just because I don't have the time to spend in it. And that makes me feel sad. Definitely sad. And I want to do more, but I can't just because because of time. But yeah, I don't even know where I'm going with this. But this constant shift of identity moving on, almost like shedding skin. All right, is that I shed my skin from history testing. I'm shedding my skin a bit from indie hackers, but not quite. And, you know, moving through life, I think, like, I think we almost become different people as we grow up. I mean, I think I'm in my early 40s now, and am I the same person? I was 10 years ago. So yes, but no. And that's okay. Yeah, I don't even know where I'm going. But yeah.

Michele Hansen  27:31  
It's interesting you say that I love how you dove into the identity shifts of that. And you're like, so even though you're no longer with, you know, indie hackers proper. I still think of you as the mama bear. The indie world is my head but like that's, that's it's you know, Rosie, Sherry mama bear of the indie hackers.

Rosie Sherry  27:59  
Well, I like that. I'll have to put that on my Twitter. But it's interesting, right? People will always remember you for different things. So there'll be people from the testing community who will always remember me for ministry testing, and things I did, and nothing will probably change as much in a ton of indie hackers out there will remember me as being the mom of their I love it. Yeah, and like, the more I do all of it, orbit, the more people associated me not with being indie, but being more all about community. And that's okay, as well. Right? And what does it mean is that, I don't know. But But I think like, I mean, you know, I guess it goes back to trends, life, the world changing, no one has careers for life anymore. And this is you know, probably I guess a proof of it is like, let's, you know, change as we grow, let's be okay with, like, actually discovering things. As we learn about ourselves, and as we learn about the world around us, and, and adapt and we should Yeah, I think we should all be able to do that and make make it feel okay. And make it you know, not not feel like step backwards, is you know, it's not a step backwards. It's just like, as you as an individual, you you're doing what's what's right for you at any point in your life. And that's, you know, that's okay.

Michele Hansen  29:45  
I'm reminded of the Walt Whitman, quote, I contain multitudes and, and I feel like what you're saying is, is about that we have many different identities and even the identities of us in other people's minds may be different than what we think of ourselves as or reflects a version of us in the past. And, you know, you're that that identity that you had as a founder, the identity you had, as the community person for indie hackers. As rosy land, as community person at orbit, like, all of those are valid, and they all exist, regardless of you know, what you're currently we're doing. And I feel like, what you're saying is, you don't really have to choose one, you know, you can still you can still have all of those pieces and so many more pieces of yourself. And, and it's okay to shift and change and grow.

Rosie Sherry  30:54  
No, think like, as as, I guess, like an unschooling approach to things we encourage, everything we do is like child led learning. And, like, I live that, that same philosophy in life is like, you know, I think like, like, as I get older, I just, I just can't spend any time on anything I don't enjoy. And then when I look at my kids, I'm like, why should they have to spend any time on the things that they don't enjoy, we should, like, you know, focus, focus all our energy as much as is possible to do the things that we love, because that's, that's like a really special place to be. And, like, at the moment, like, like, you know, I've been working for 23 years of my life, when I started out, working. Man, it was just like, a different place. And like, where I am, now, I'm like, this is just such a better place to be doing work that, that I love that I appreciate that, that, you know, I believe I can have impact on. And if I look back at myself, like 20 years ago, and see see where I am now, I say, I would have like, I guess, never, never imagined that this kind of life is possible. The life I had then was about working in jobs that I didn't really enjoy that much, or for companies that I wasn't really, that interested in what they were doing. And now it's like, everything's flipped to like, I'm working for a company that I believe in what they're doing, I enjoy the day to day work, we're aligned in the things that we want to do. And that's just like, Whoa, you know, how, you know, how great is that, to be a part of that. And regardless of the outcome, whether, you know, I continue to rise up in the company where they continue to get pay raises, whether whether orbit ends up, you know, growing massively in IPO, and that that doesn't matter. To me, it's like what matters is, you know, being able to do do what I love, right now.

Michele Hansen  33:22  
Follow the things you love, even if those things take you from entrepreneurship, to working for other people and changing your identity. And, yeah,

Rosie Sherry  33:34  
I look at Patrick, my, one of the cofounders I see some of the things that he has to do as a founder. And I'm like, I'm so glad I'm not doing that. And like I can see it as the founders because like, not not to the same extent, you know, they've raised money, it's a different game. But you know, that the same principles applies, like, I don't have to do any of that stuff. And I'm very happy about that.

Michele Hansen  34:03  
It sounds like you're in a good place. Now. I want I want to thank you for for joining us today. You know, we again, in this sort of indie world, we talk a lot about building in public and you know, I talked about writing in public. But something I am really valuing lately is when people are willing to be vulnerable in public. And I feel so much from that of that from you. And not only in on on Twitter, and your support of other people, but also here today. And, and I have a feeling that your story today is it's gonna make somebody at least one person feel feel less alone and feel feel better about their journey. Hopefully you know, less shame about Going from entrepreneurship to employment?

Rosie Sherry  35:06  
I hope so. I hope so. I try. I think it's, it's hard, I guess. I mean, I don't know what your experiences but like women in tech when in business, whether it's like, I guess it's hard to stand up to certain things and be open about the challenges that we have. And so yeah, I try my best, I think my confidence increases over time. I will say, I don't give a damn anymore, like what people think. I don't know if that comes of age. But like, you know, I definitely wasn't this open about everything before. So, yeah, part of me like does it to, to help other people see, I think it's important, like, who I am a woman, five kids on schooling. I kind of want to show people that. Yeah, yes, I'm a bit obsessive with the things that I want to do. I'm, like, you know, switched on, like, all the time, pretty much. But But I spend lots of time with my kids as well, you know, I managed to make it work. And I guess that my hope is that in time, like more people can be like this, if that's what they choose, you know, if they, if they can see the possibility. You know, it's done me a lot of good. And I guess, like, there must be more people out there that want something like this. And for them to be able to see an example. I guess is, is what's in the back of my mind when I tweet when I write when I do my things? Yeah. Yeah. Well, thank you. Yeah,

Michele Hansen  36:59  
thank you so much for yesterday. I've really enjoyed this conversation.

Rosie Sherry  37:05  
Thank you, Michelle. I appreciate catching up.

Michele Hansen  37:08  
If you enjoyed this episode, please let Rosie and I know on Twitter. You can find us at software social pot. Thanks

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