Permission To... Take a Pause (Entrepreneurial Strategy)

They say fortune favors the bold. So what are you waiting for? The right time? The right sign? The right guide? The thing is, Movement Maker, you were never meant to follow anyone else. You were destined for something bolder and braver and truer, and you know it. It's time for you to write your own damn permission slip. You have permission to dream big. Not that you need it from us. Fortune favors the bold. So what are you waiting for?

Hello, hello, Anna Wiggins. Welcome to the Permission Slip Podcast. How are you today? I'm great.

How are you?

I am doing very, very well. Um, I— we're, we're in the same space. Let's just be, let's just be clear. I'll lean out my door and I'm gonna wave. I'm gonna wave at you. Um, so why don't you introduce yourself and then explain why we're in the same, why we're in the same space.

Okay. Um, I am Anna Wiggins. I am a former business owner of Loveliest Bridal here in Knoxville, Tennessee, which I sold in October 2022. Um, and since then I have gotten to do several things, one of which is working as the operations manager here at Ott. So I am just down the hall from Erica and have my door closed so that we don't hear an echo.

All right, I'm new to this producing at the same time that I'm talking thing, so that's on a— that's normally Sally's gig. She is with her friends on vacation today, but I'm really glad, I'm really glad you're here for a number of reasons. You, as we said in the introduction and then your introduction, you took a pause from entrepreneurship after you sold your business. Let's talk just for a minute why that pause, because I know it was intentional for you.

Absolutely. In January of 2022, I went to a business retreat with Booth Andrews here in Knoxville. And I went into it fully intending to crunch numbers, look at data, talk about analytics and marketing strategies, and come out of that retreat with a game plan for how to grow my business even more and to, um, kind of get it back to— it was at the pre-pandemic levels, but it wasn't growing at the same rate that it was pre-pandemic. So it was kind of like, okay, how do I stimulate more growth in my business. And that was my plan going into this retreat. And Sneaky Booth got us crying, got us in our feels. There's a lot of internal work, a lot of really intentional time spent thinking about what I needed for myself, for my family, and for my business. And I came out of that retreat with such clarity. I even took a picture of myself that day, and you can just see the, the ease, um, that I had, the sense of peace that I had within myself, that I knew the next step for me was to sell Loveliest. Um, my mom has had dementia for years, but it was progressing, and she lived in another state. Um, we had survived the pandemic as a business, but I also had my daughter in August of 2020, so I had a young child a shift in my business, a mom who needed more from me, um, in a caregiving role. And, you know, that was just on top of other life, you know, having a husband, having friends, having, you know, trying to maintain just life itself. Um, and I, I recognized from that retreat that the one thing that I could let go, um, was my business. I couldn't let go of my family and my friends and the other things that were so intrinsically a part of me, but I felt like I had accomplished what I wanted to, um, with Loveliest when I set out to own it. My goal was to own it for 5 years. I had had it for 6 years. Um, so it just, yeah, it was with such clarity that I made that decision.

And when you— so I think clarity was the biggest gift you had going into making that decision, but where, where were the permission slip moments in making, in making that choice?

Yeah.

Um, or executing it, not just making the decision, but actually executing the decision.

I feel like there weren't a— I think that one permission slip at the retreat when I allowed myself to like have the realization was the biggest one, because once I made that decision, it was kind of funny how many signs or how many, you know, fortuitous events would come into play that just helped me recognize that I was on the right path. After I sold it. I mean, it was my baby. It was— Loveliest was— I, I had it before I had my human baby. And so people knew what it meant to me, and I was so intertwined with my business that we were kind of one and the same in some regards. So when I sold it, that was almost always the first question I got is, oh my gosh, have you regretted that decision? You know, was that the right decision for you? And I think giving myself the permission, um, at the beginning to recognize that that's what was right for myself. Um, I guess it was just a really big permission slip. I don't know, like, I feel so resolute in that decision that I, I didn't need a lot of other permission slips throughout, throughout that journey. After I sold it, the permission to allow myself to not jump into the next thing was a lot harder.

So, well, so let's talk about that. So You and I kind of had just gotten to know each other right around that same time. I knew you as the loveliest owner, but we just started engaging in more conversations once you were past the sale of the business. And I'm sure a million other people were like, okay, well, so what are you doing? What's the plan? Because the assumption was you had sold it. And so there was a plan. And I think the way, I think the way you answered it, um, for the first few weeks that I saw you answer it, you were kind of like, I, I'm a little, I'm not, I don't, I'm not really sure. Um, but then you really kind of settled into it. So how, what did that look like? What did that process look like for you, extricating yourself and then releasing of it a little bit?

Yeah, the plan part is so funny. I like to joke for Um, Christmas one year, my husband got me a book about Hawaii, and I was like, oh, I've talked about— sorry, not Hawaii, Switzerland. Hawaii was our honeymoon. He got me a book about Switzerland, and I was like, oh, he wants me to learn more about Switzerland because I talk about how I like it, but I don't really know enough about it to say that I like it. And then I opened up the first page, and it said, for our 2016 trip to Switzerland, and I lost it. And I was just so excited to go. But the gift was not that we were taking the trip. The gift was that I got to plan the trip. Like, I am the epitome of the planner. I like to have a plan. So the fact that I would sell a business and not have a plan, not have a next step career-wise, um, was, I think, as unfathomable to everyone around me as it was to myself. And it was very uncomfortable. And so Um, I don't think I allowed myself to be uncomfortable at first, or, you know, I was uncomfortable, but I wasn't enjoying it. The longer I was in it, the more and more I was able to engage with other women, um, both friends and family members, but acquaintances, other business owners. Um, and I just found this common theme that so many of us feel like we are in this period of transition, whether it's having a child or we've started a business or we've thought about starting a business, but we're in a full-time job. Um, we've just gotten married or we've gotten divorced. Like, there's so many people around me that I feel like were in the similar space of being, um, in transition in some aspect of their life and being uncomfortable with it. And the more I saw it in others, the more I wanted to, like, you know, hold that space for them and be a support for them as much as I wanted to be that for myself. And I honestly think the longer that we do something, the more comfortable we get with it. So the longer that I didn't have it figured out, the more I just naturally had to get comfortable with it because it became my norm. Um, and I think a big piece of that was when I started writing, um, in February of 2023. I started my blog on my birthday. Um, and it was just a birthday gift to myself to allow myself to express myself in that way. I consider myself maybe an overshare in some regards in the amount that I post, you know, personally about my life as a caregiver for my mom with dementia and parenthood and business ownership. Like, there's just a lot of things that have shaped where I am today, and I share a lot of that. But allowing myself to do that and giving myself the permission to put that out there publicly um, is probably the best gift I've given myself because the feedback that I have gotten from, from others when they feel seen, even if it's one person that reads it and says, oh my gosh, this resonated so much with me, that fills me up more than anything.

Well, I mean, you're, you're a beautiful writer. It's a huge talent of yours, um, and I think part of the beauty of it is the honesty with which you approach it, um, and we find that so much just in our OP community and our permission slip community that the more people talk about things, the easier it becomes for others to talk about it. And so I think your blog that is now set on Substack— so we've got, um, we have the code right there, uh, you can pop over there and subscribe to her, her Substack. Um, I think the more that you're putting out in the world, the more conversations that you are opening you're opening up about hard topics, um, that we can talk about in person, or we can be on a Zoom call and we can talk about it. But when you put it out into the world in the way in which you are doing that, um, it just opens the conversation wider.

Absolutely. Yeah, I was working on a post this morning. It's not published yet, but— and it's kind of talking about that permission to allow yourself to chart your own path. And no one is going to value your goals and like your limitations as much as you are when you're setting those, those next steps for yourself. And so you can talk to so many advisors and so many confidants and those who have gone before us and get their advice, and I suggest doing that. But at the end of the day, the person who's gonna, you know, suffer the ramifications or thrive because of them is the person making the decision, and it's not going to impact anybody else as much as it is you. So I just think giving yourself that permission to chart your own course, even if it doesn't look like what everybody else is expecting, and it might not be a thoughtful, planned-out journey, it might, you know, happen one step at a time, one day at a time.

Draw the map while you're at it. Yeah, yeah, I'm here for that. Um, okay, so you step into this, um, into this new realm, um, and you've given yourself permission to not do anything. Um, how long did that last, Anna?

Um, I guess it was May. Well, so I started writing in February. That was not like an income-producing thing, that was just for myself. Um, and then maybe April, I think, um, I saw kind of an acquaintance of mine, somebody I knew through the Women in Entrepreneurship group, posting about a health journey that she had been on, and I just reached out to her and said, hey, I know you are a solopreneur running your business and you've had some health things come up that you've shared openly about. I can imagine that's taken a toll on your ability to do all the things you need to do as a solopreneur. Um, could you use some part-time help? And it again was just one of those fortuitous things where she said, I have been thinking about this so much and just so afraid to take that leap, or kind of not knowing, like, how to put it out there, what I wanted it to look like. And this would be great. This would be a great fit for me for right now, kind of a temporary thing. And so that's what I did. And I did that for a little while until I also learned that you were looking for help and that I could— my goal is to help other females and especially female entrepreneurs. And so knowing that there was such alignment for what I ultimately wanted to do personally, professionally with OTT, um, I felt like I couldn't pass that opportunity up either. And then I was also able to facilitate Co-Starters, um, which is a 10-week business development course through the Entrepreneur Center here. So I, I took on all of those roles all of a sudden, kind of, um, in fall of '23. And I had to give my pers— myself permission again to let one of those go, um, because it was You know, it was as much as I want to do it all, I can't.

So yeah. So what, um, so you went from, I mean, I'm saying doing nothing, which is, that's stupid. You were doing so much, but I'm talking about, you know, professionally, yes, fully professionally, a job of some sort. So you took kind of a small break and then you were like, I watched it happen. You were like, break's over, I'm all in. Um, and then you recognized maybe that needed a little bit of a of a shift too. So you've at this point then within 12 months have like made some multiple big pivots. I know we don't like that word, but big pivots or big moves or big, or big changes. So when you get to this third one where you're like, okay, now I've got 3 new jobs at one time, um, talk us through what it looked like to say, you know what, I need to make one more. One more pivot, like, and let go of one of these. So what, what did that look like for you?

I think it was recognizing in my body once again, um, okay, Anna, here you are, you just sold a business not that long ago because you're— you were feeling so viscerally that you couldn't do everything to the level at which you wanted to, to do it. Um, and here we are again with that same feeling bubbling up of, I can do all these things, but not well. And as I think it was, it was hard for me to let one go because I was afraid I was going to let someone else down. And I think it was that recognition this time around that I may let someone else down, but I can't do that at the expense, you know, I, I have to look out for myself and my family. So as much as it might let someone else down, I had to do what was best for me. And I am a big proponent of the two, like, most important things in business and in relationships are communication and expectations. And I had said when I started that one part-time position that I would likely only be there through the end of the year at max. And so having that expectation already outlined with that person gave me the ability to, you know, to give myself the permission to say, you know what, we, we had these expectations in place. I just need to be honest and communicate effectively why I've made this decision. And I really felt like I had performed the, the task that I had set out to do with this business, which was to get it to a better place in terms of like processes and, um, systems. And so I felt like I had already done that, um, pretty much to the extent that I could. And I think those those guardrails of having the clear expectations and communication of, okay, I'm doing what I set out to do. I'm going to explain that effectively. And we left on such great terms and I'm forever grateful that it worked out the way it did.

Well, and your being there set her up for success in such a way. Yes, it was a powerful one. I know it wasn't possible for her before she had another teammate and now we're watching her continued growth and it's It's really awesome to see, but I really like the piece of that story where you were honoring the permission slip to yourself and not others. Because again, as women, we talk about this so much, like so much of what we do is generally in service to others or for the betterment of others. And there's nothing wrong with that, but we do forget about the us, the individual piece. Of who we are. And I am personally super guilty of having done that to my family as well. So I think it's a muscle that as you give yourself the permission slip, you know, the more you use that muscle, the stronger that bad boy.

The older we get, the more, yeah, the more at ease I've become with using them.

Absolutely. Well, and even you coming into OT, and I mean, just to brag on Anna for a minute, like she has She has been instrumental in what, as a business and as a business owner, what I have been able to do. I'm, I mean, eternally grateful to her for it. But the conversation from the get-go has been that Anna has, you know, Anna has goals and she has things that she wants, wants to do. That doesn't keep us from doing what we're doing today. We just know that that is so grateful for that. Right. So let's talk about that because you're working with and for a female-owned, female entrepreneur-focused business. You're wanting to do something similar but different. And we don't have to get into that. But I mean, you were like, okay, here. That's not an easy thing to say out loud, Anna. And you do it with grace. Thank you.

You do.

I'm really impressed by it. So how, what recommendation would you give? I love the part about expectations, um, but like really tactically, how, how can that look for somebody? Hmm, sorry, that was hard. I didn't tell her I was gonna—

that's a hard question. I mean, I think again, it's that clear communication of— I think coming in, like, that was a fear of mine. It's like, I want this, I really want this to work out, but I also, I don't want it at the expense of me burning a bridge or letting myself down or letting you down to the point where the benefit of having the experience would have been negated. Yeah. And so I think, I guess that's how to look at it, is, you know, um, don't sacrifice what your values are and what your goals are to appease somebody else. But yeah, I like— I don't know how else to say.

I think it's great. We, um, I talk with a lot of women, and when we, when we're talking through kind of a hard thing, or how, how do I handle this, my question is always, what's the worst thing that can happen? Yes. Um, because when I think about our co-working space, what's the worst thing can happen? It happens all the time, which is that women's businesses outgrow our physical space. Um, and so is that great from a revenue perspective? No. But also, if the worst thing that happens is that we're fulfilling our mission of helping women grow the businesses that they want to, then great. And so if the worst thing that happens with me bringing in on our team a very smart female entrepreneur who can support us and help get us to a strong point before then potentially going out and doing her own thing, like That's not— there are a lot worse things that can happen if you don't have that perspective on it when you're coming into it, right?

Well, and I don't think everyone does. I think I'm fortunate that in honoring my own truth and speaking so openly about it, I think I end up finding the people who similarly do the same. I think we attract, you know, what we put out. And so Yeah, I think that's why it's a good fit because we think similarly in that regard. And I'm grateful.

And the other thing is I get to have, I get to have a front row seat to all the possibilities with you. And I know you've looked at, you've looked at and you've kind of made some steps towards some possibilities, but then you've been like, no, I'm going to put that to the side or whatever. So it's been a, how long have you been with us now? A little over a year.

A year?

I don't even know. It feels like forever in the best way possible.

Yeah, I think this fall will be a year.

So, so in that time there's been 2 or 3 things that you've kind of looked at and decided that's not it. And you're— and you talk about it openly here. We, you know, we discussed some of that, but what, what lens are you looking at opportunities through for what your next step is?

I look at it financially as to what I can invest resource-wise, asset-wise. And then the biggest thing is time. I have gotten so much better about putting boundaries on my time and my energy. And, you know, one of the thoughts I had was for an indoor play cafe. And as much as I wanted to champion that idea so much, if anyone in Knoxville wants to do this, talk to me about supporting you in some way, because I want it here so badly. Um, but I look, I started writing a business plan for this and I was looking at how many staff I would need to hire, how much programming I would want to bring into it, um, what hours we would be open, how much, how much, you know, capital it would need to get it just off the ground and running. Um, a brick and mortar space and finding one that was reasonable, which in this market, good luck. Um, I'm talking everyone out of it now, but somebody go do this that has the ability to. I love the idea so much that I wanted to make it happen. Um, but when I, when I force myself to write it all out and look at it in a business plan template, I just recognize like I don't have the capacity to do this right now. Maybe in the future, maybe when my daughter's in actual school and not, you know, daycare, not sick all the time, all the things. Um, but yeah, so I think it's just looking at it through the lens of what is my capacity energy and time-wise And then what resources do I have to make this happen or are available to me that I feel like I could pursue?

Yeah. Well, and you also have just been open to— you've been open to possibility. You really have. I mean, there have been some very disparate— the opportunities have been far and wide. That's been really fun to watch you kind of weigh the opportunities that exist out there too. So, okay, so let's go back to Permission Slip Conference. So to get super meta, she came on the team right about the same time we were launching the conference. Welcome! Yay!

Here you go.

So you've been like intimately involved in the backend.

No big deal to put a conference together for the first time.

And you also, I mean, you got to go through the fun of like, we think this checkout's gonna work, and then we tried that and didn't. So we opened a new kind of— I mean, y'all, she has been all over all of the automations in the backend, et cetera. But then you actually got to be there on the day of, and then you've been a part of helping us pull together this next iteration of it. So what was your big takeaway either from the planning piece of it or the being on site or both? Like what has been your takeaway from the experience? Because this is this is kind of your first event you've been like full in the trenches with.

Yeah, um, I think from in regards to the planning it and what I was seeing, it was so similar to starting a business, watching other entrepreneurs start a business. Launching a nationwide pull, um, event was such a major undertaking. Um, and so I think just seeing all the work that went into it. And I was only seeing a fraction of it because so much of it you were doing behind the scenes. You and Sally were, you know, y'all handled so much more of the logistics and the pieces that maybe like other people can hopefully help you with in the future as it continues to grow. But like to get it off the ground, it's just like starting any other business. You just, you have to be in the trenches, you have to be boots on the ground, and you have to invest so much, um, of your energy into it. And so I think seeing that from behind the scenes and just knowing how much passion there was behind it made it all that more special when I saw it come together. Um, and just the, the conversations that were coming out of that room and the excitement and the energy. I talked to somebody who was saying like it was almost hard to leave because it was such a big day. It was so impactful. And then it was like Okay, now it's over. Like, I don't want it to be over yet. So I know this year we are planning to kind of extend it a little bit with some opportunities. I won't give anything away, but like, just, you know, some additional opportunities to maybe network and, and to learn and grow, like, on that Saturday after. And I think that's a big— I think that's a, that's a major improvement because it allows that, like, time to just process what just happened because it was such an impactful day.

Um, but yeah, well, and tactically too, um, you know, Sally and I, um, we bring our strengths to the table, but we, you know, there's some pieces we're missing. And, um, we did with what we could last year until we got, you know, you on board and could help with some of the pieces that are not really our strengths. But we were chasing our tails a little bit, trying to stay— trying to keep our businesses running and doing all the things, and then also trying to take on this thing that was a huge undertaking, right? So we went into it with full excitement for this year, but a little bit of trepidation, just kind of knowing what the hit on our bandwidths were going to be. And then instead of that being the case, we have found ourselves all, everyone on the team kind of like, are we doing this right? Um, because so much of it has been automated, so much of it has already been ideated. Um, that I'm not going to say it's easy because it's not. There have been some, there have been some tears and some sleepless nights. But, um, can you speak to kind of the power of automation? Because I know that that even is something that you didn't have a huge background coming in with, but you were like, you're on it at this point.

Yeah, it's been fun to learn like what the different, you know, tech resources are and opportunities for improvement. But, um, yeah, we— I joke with you that I feel like I'm automating myself out of a job, and I know you say no way, um, but it is. It's like It's so impactful and powerful and rewarding to see that come to fruition. And I feel like I've— we've been doing that a little bit with Aut and then we're doing that with Permission Slip. But it's like at the beginning you feel like you're investing so much work to make— to pick the right pieces and put the automation together correctly. But then once it's working, it's like I can go pursue that other thing. Yes, we all know that I've got a million different bubbles popping up above my head, and, you know, I don't know which one to poke or pick today. Um, but I can't pursue those until I free up some space and time. And I think it's similar for you as a business owner. It's been fun to watch you, um, both with OTT and with Permission Slip, since you are, you know, founder of both of those, um, co-founder of Permission Slip. But seeing you get to a place in your businesses where you're like Oh, I can continue to grow my business and work on improving my business because the managing and running my business is now just a will.

Yeah, under control. I, I think, yeah, I like that. I actually yesterday I thought about this, my husband and I were talking and I was like, I just, um, I'm not sure I'm accomplishing anything. And the— and I said this week, um I've done a lot of really, really big things, like a lot of really big things, but I'm not checking my email every day, right? Like, I may be reading it, but I'm not responding to it. And I had this realization last night talking with my husband that I'm still years later, years later from leaving the meeting planning world where I had to answer emails every time it came through, as soon as it came through. To me, that that's how my brain is measuring my work output, right? And so at the end of the day, yes, I, um, am helping spin up a, you know, a nonprofit, and I'm, you know, creating like really deep content and doing some branding exercises, but my brain is still saying, well, you didn't send any emails, so you didn't get anything done, right? Um, but now that I've got this extra space courtesy of the automations that we've put in place and the team support, et cetera, I at least can recognize that that's the story my brain is telling myself. So now I can work on it. Whereas for all the years, the noise in there was so heavy, I never would have been able to recognize that piece at all. So yeah, that's really fun. That's really fun too. That's really fun too. Okay, so we are coming to the end of our time, Anna, and I'm supposed to ask you See, Sally's normally the main host, so I just do as good as I can. I'm supposed to ask a question, which is, what are you— what is your current permission slip, or what is the next permission slip that you're writing yourself?

I think the current one is kind of what I talked about earlier, which is allowing myself to pursue career goals and wealth building goals. That I find impactful and beneficial to my personal circumstances, and not necessarily based on what the world around me is telling me is the only one chart path, path to chart.

I love it. And I love the use of the phrase wealth building. Let's just give that a—

I love that, right?

Yeah, I love it.

I love coming around on my money mindset and allowing that wealth is not a bad word.

I am writing myself a permission slip to let Anna give me some lessons on that. Okay, perfect, wonderful. Thank you so much. I would love if you all would subscribe to Anna's Substack. It really is some great reading.

They tend to be pretty, pretty quick reads also, so I think it's only like 2 to 4 minutes, and there you get access to all of the content with a free subscription.

But you also can pay Anna to join her subscription and get some extras, access to her older writing. She does an audio reading of her pieces as well. And I would love for you all to support her in that way too. So thank you very much. It's been a delight chatting with you via this way and not just in the hallway. All right, everybody, go make it a great day. Have a good one. Bye.