Managing Through The Worst Case Scenario with Lauren Caselli

Lauren used to run an event planning business for tech, and after her best year ever in 2019, was ready to give 2020 a run for its money. Sadly, the opposite happened, but out of breakdowns come breakthroughs.

Susan Boles
November 17, 2020
Quote: "There is no timeline on grief, of course, but a lot of times, it lasts longer than we expect it to because we don't have the tools in our toolbox to deal with it alone. And we don't ask for the help we might need." - Lauren Caselli

What happens when the worst-case scenario becomes reality? Every business owner I know has that nightmare that runs through the back of their head...

For a lot of business owners, this has been the year where they had to figure out what the answer to those questions was.

How do you manage that change? Do you shut down? Do you pivot?

When everything stops, how do you decide what to do next? How do you actually get through that and lead your business through change? Or make the decision to actually close?

Today, I'm talking to Lauren Caselli. Lauren was on the show back in March in Episode 25. I talked to her about cash flow planning in a crisis right as the shutdown was really starting to take effect and Lauren's event planning business was heavily affected.

Lauren's been through a MASSIVE change this year, so I wanted to bring her back on the show to talk about how she's been managing the impact on her business.

Lauren Caselli helps womxn and gender non-binary folx get paid like the expert that they are. Lauren used to run an event planning business for tech, and after her best year ever in 2019, was ready to give 2020 a run for its money. Sadly, the opposite happened, but out of breakdowns come breakthroughs.

She is the founder of the Boss Lady Bash, a now laid-to-rest community of female entrepreneurs in Montana, and is working on launching The Money Club that helps womxn make strategic choices with the well-earned money that they're making.

Listen to the full episode to hear:

  • How Lauren’s cash flow management skills gave her the time she needed to make strategic decisions instead of reacting out of panic
  • Making a HUGE pivot in your business and how to stay resilient
  • Processing grief as a business skill
  • An update on what Lauren decided to do about her business this year

Episode Transcript

Lauren Caselli (00:00):

There was a period where I had a decision to make which was, "Do I keep panic trying things and seeing what sticks or do I not do anything?" I've been in business for about six or seven years. This iteration of my business for about four, I just knew that I never make great decisions when I'm under stress. So I really made the choice to not work until I knew what direction I was going in, which is an incredible luxury and incredible privilege.

Susan Boles (00:30):

What happens when the worst case scenario becomes reality? Every business owner I know has that nightmare that runs through the back of their head, "What if it all just stops? What if no one needs my services and suddenly no one needs what I'm selling? What do I do then?" I'm Susan Boles and you're listening to Break the Ceiling, the show where we break down unconventional strategies you can use to save time, boost your profit and increase your operational capacity.

Susan Boles (01:02):

For a lot of business owners this was the year where they had to figure out what the answers were to those questions. How do you manage that change? Do you shut down? Do you pivot? When everything stops, how do you decide what to do next? How do you actually get through that and lead your business through change or make the decision to close? Today, I'm talking to Lauren Caselli. Lauren was on the show back in march in episode 25 and I talked to her about cash flow planning in a crisis right as the shutdown was really starting to take effect.

Susan Boles (01:38):

Lauren's event planning business was heavily affected. Lauren has been through massive change this year, so I wanted to bring her back on the show to talk about how she's been managing the impact on her business. We talk about processing grief as a business skill, what she decided to do about her business and how her cash flow management skills gave her the time she needed to make strategic decisions instead of reacting out of panic. Hey, Lauren. Thanks for coming back to the show.

Lauren Caselli (02:11):

Oh, I'm so glad to be here and so much to talk about.

Susan Boles (02:14):

There's so much to talk about. So the last time you were here was mid-March. It was just after everything really started happening with coronavirus and shutdowns and we were talking about how you and your event business were reacting. I know that you've made some major shifts in your business since then, but can you tell me what happened to your business after we talked? What's been happening for you this year?

Lauren Caselli (02:38):

Yeah, totally. It's so fun to be six months out. I feel like if we had done this three months out, I would have been still in the thick of a lot of crying and not sure. I think over the last six months, there has been like, I would say a specific set of phases and the first phase really was this denial that anything was going to change long term, right? There was sort of this immediate... And I had clients. We talked in March and I had just come off of one of my big clients canceling their large event.

Lauren Caselli (03:12):

And for those of you who haven't listened to the past podcast, I primarily work with tech companies. So at the time, this was before like Twitter had announced that they were going remote, but at the time that we chatted, it really was seen as a temporary yet devastating blow. I had clients who had events in June and July who were still moving forward on those events, which is bizarre, so bizarre to think about.

Susan Boles (03:35):

I know. Now, thinking back like we were all kind of holding our breath thinking this is a pause. We're going to do lockdown and then we'll go back.

Lauren Caselli (03:44):

Right. It's unfortunate in the short term and then in a few months, it will all be fine. When we were speaking that's where I was operating from. I was working with a client. They canceled in March. The event was mid-March. I was working on making sure that that contract was able. I think there was a lot of unknowns and so we were working through the end of that contract because I couldn't deliver the event because they canceled it.

Lauren Caselli (04:11):

But for all intents and purposes, I was like, "Man, this is going to brew a couple months. I'm going to have to like cancel some things and not have my HelloFresh subscription anymore. But by June we should be good, right?" Clearly that's not what happened. So then as many business owners, I think particularly those... I always thought that I had the best business which was online sometimes and in person sometimes.

Lauren Caselli (04:39):

So while so many of my online business owner friends saw a huge uptick in their businesses, all of my clients sort of just kept... Every week, it was like a new client was like, "Hey, we're holding off on this. Hey, we're not starting the project until we get a little more clarity." I would say by April, I was in full-blown panic. I started doing what I think a lot of people did which was panic selling. I was like, "Let me come up with a workshop. I can do this. I know how to do it. Let me run this. Let me do an affiliate program. Let me sell..." I don't even know what I did. I'll do a flash sale of a course that I had created specifically around sponsorships for events, which oddly was still selling well. I think people were maybe still in denial. I'm not quite sure.

b (05:25):

So there was this pretty significant period of panic from, I would say the month of April into early May. And then... That was exhausting. And then what ended up happening is I knew that the next iteration of my business was not... At that time, it was like Twitter had announced that they were working from home until July 2021. Most big tech companies said that the South by Southwest had canceled. Most big tech companies said that they weren't, which was my client base weren't going to be hosting in-person events until at least July 2021, if not the end of 2021.

Lauren Caselli (06:03):

So there was the writing on the wall. There was no way that I was going to be able to maintain my current client base. And the sales process for an event client is long. It's a year, 18 months. It wasn't like I was going to be able to turn around and pick up a bunch of new clients virtually or something. Also, that's not where my heart was. So I didn't want to go in the virtual event route. I didn't want to switch to try to do smaller workshops or things that were kind of able to happen with the new mandates of social distancing and whatnot.

Lauren Caselli (06:39):

So there was a period where I had a decision to make which was, "Do I keep panic trying things and seeing what sticks or do I not do anything?" I've been in business for about six or seven years. This iteration of my business for about four, I just knew that I never make great decisions when I'm under stress. So I really made the choice to not work until I knew what direction I was going in, which is an incredible luxury and an incredible privilege, but I consciously sat down one day and said, "I'm not working anymore. Nothing is working. I'm making a few hundred dollars here and there."

Lauren Caselli (07:19):

I had sat down with my bookkeeper and she had said, "Look, you have enough runway. I've been planning on hiring a project manager this year." So she's like, "Well, if you're not hiring, you have enough runway to last you through October."

Susan Boles (07:31):

So you mentioned that being able to not work or not react is coming from a place of privilege, but let's also be clear that you had been saving pretty significantly to make sure that you had a really good cash cushion in your business for this exact scenario. So you had done a lot of work to make sure that you were in a place of privilege.

Lauren Caselli (07:56):

Yeah. Especially after this year I had always had a three-month cash cushion in my business. That was something that was non-negotiable. After I started learning about business finances that wasn't always a thing. Now, even this year, I'm like, "Oh, three months." So I had been planning on hiring someone this year, a project manager and instead I didn't do that. Essentially, I sat down with my bookkeeper and she was like, "Look, if you don't do a single thing from now from April until October, you can still pay yourself."

Lauren Caselli (08:28):

She's like, "Don't sign up for any anything else." She's like, "Basically, just keep your expenses as they are. Continue paying yourself and you'll have money through October." And part of that was also my EIDL, the advance and the PPP loan. I was very lucky to get both of those things quite early because in events, I was not someone who was like, "Let's wait and see." I was like, "No, my business is very severely impacted." So I would say acting quickly on those two programs was definitely a great benefit for me.

Lauren Caselli (09:03):

I don't remember what the original question was, but I had a big cash cushion which made the ability to not work and also having a great bookkeeper who helped me do that projection was essential to me being able to... I mean, I didn't like it, but it was essential for me to be able to evaluate the situation as it was, understand that from my own experience I couldn't like... It was like a finger trap. I couldn't struggle against what I was going through. I really just needed to stop and evaluate and wait until I knew where to go next and that is what I did.

Susan Boles (09:42):

So one, the reason you have cash cushions is for exactly that reason because nobody can make a place. Nobody can be making good decisions from that place of panic. When you are panicking and dealing with crisis, nobody is going to make good decisions. So having a cash cushion is essential to be able to give yourself time to process and think strategically. I think one of the hardest things to do is to say, "I'm going to step back and I'm going to be patient and I'm going to wait and see what the right decision is for me."

Lauren Caselli (10:21):


Susan Boles (10:21):

I think that's a really... When you are in like crisis reaction mode, I think that's probably one of the most difficult things to do.

Lauren Caselli (10:29):

For sure, totally and definitely it's a practice, right? It felt almost agonizing to me. I would wake up in the morning and I would be like, "What am I going to do today?" I read a lot of books and I was doing a lot of anti-racism work. So I had a ton of reading to be doing in myself imposed work hiatus. But it felt so indulgent and so it was agonizing to tell myself this is part of the work. The part of the work is to not do anything and this is a new challenge that I had never foresaw. It's not the narrative in business, right? If you're not working, if you're not closing, you're not doing it right. And I was like I just knew that I couldn't make any decisions that were well informed, if I was focusing on panicking.

Susan Boles (11:24):

Absolutely. So that leads into my next question is that for you personally, I mean, I've been through a few major business sales and transitions that weren't necessarily financially great and they were super emotional. So I know how hard it can be to process all of that, but for you personally how did that all play out? How did you deal with that, deal with those emotions, that grief, that big stuff?

Lauren Caselli (11:54):

Yeah, totally. That's such a good question and I think it's really good to ask. I do think that a lot of times particularly in business, we look for tactics and solutions and 10 steps to do something. A lot of the work, a lot of this work is part action, but it's also part feeling. It's also part recognizing and affirming. So on top of this, not only did I lose my personal income. I was still paying myself a salary, but my business income.

Lauren Caselli (12:28):

Then my partner who had just started a brand new job in Portland Oregon, and I was planning on moving there in April lost his... He was laid off three weeks after he started because of the pandemic. So here we are, two people who are out of work, together in a two-bedroom household, which is we're very lucky to do and we live in Montana, so lots of wide open space who were going through really hard emotions both together and also separately.

Lauren Caselli (12:54):

He was grieving in his own way and I was grieving in my own way. What I knew from my past experience of dealing with going through hard things. As a business owner, it is impossible not to have hard seasons. I basically was like... I called in all the reinforcements. I made sure that my therapist, she was personally doing virtual sessions. I called our couple's therapist and I was like, "We need your help. We don't know what we're doing and we are not communicating well so we need your help on this."

Lauren Caselli (13:24):

Then I basically told myself like, "What would be the easiest thing for us to do together in our relationship, but also for me to do so that I know that I could get back to work in a few months?" And part of that was really... I live in the mountain west. It's snowing nine months out of the year and this all started happening in March and then May was when, again, it got very, very real. And it was starting to be beautiful here. I basically said, "Look, I'm going to enjoy every second of this summer and whatever that means, I'm going to find joy and find pleasure and focus on that."

Lauren Caselli (14:00):

If I do that by the end of the year, I will mark it as a success. So I got help which was our therapists and I focused on doing things, the only things that would be fun, and pleasurable, and exciting. A lot of that was reading, spending time outside, walking, hiking. There was a lot of crying. There was a lot of grief. But I had help to process it. I think a lot of times when people go through grief, they stick it out or whatever, and it can last a lot longer than... And again, there's no timeline on grief, but it can last a lot longer maybe than we expect it to because we don't have the tools in our toolbox to deal with it alone and then don't ask for the help that we might need.

Lauren Caselli (14:43):

So I was very upfront with myself and my partner saying, "I need help to be able to do this in a way that's going to help me move through it faster than if I just tried to struggle with it alone." So that's what I did.

Susan Boles (14:58):

I love that because I think, especially when we're going... I agree with you. There is no way to not go through hard things as a business owner. You will have times where it's just really hard and it's really emotional. And our instinct and our culture says that we should just be saying, "Oh, everything is fine. Things are great. Things are so fabulous right now. I think one maybe one of my favorite things about this whole pandemic thing has been a little bit lessening of that where it's like more socially okay now to be like, "Hey, I'm not okay. Things aren't great." That's acceptable. I mean sometimes when you're going through these things, the instinct is to just be really closed off about it and really it's just a challenge to reconcile the stuff that's going on inside and the business owner that is being presented on the outside, I think sometimes.

Lauren Caselli (16:04):

For sure, totally. And just like we all have systems of bookkeeping and systems of... We have all these systems in our business, but we don't have systems of dealing with hard things. We don't have systems of grief. So that was one of the things that... I'm sure we'll talk about what I'm doing now, but one of the things that I really had to do was like grieve my business as it was. There was no... Even if I decided to go to virtual events, which was not my passion, I had to grieve a life that I essentially had lost and that was the truth, right?

Lauren Caselli (16:32):

It was not going to be the same. My business was not going to be the same, but I was really lucky and that I... My motto this year has been get ready to stay ready. What I had done over the last four or five years in business is I had built a system. A system to deal with hard things which was finding the right people to help me process and learning how to be easy on myself and give myself permission to do what I needed to do. And that is a system. That's not like, "Oh, it's some feeling thing." It's like I have a person that I go to and I have another person that I go to, to help with my relationship.

Lauren Caselli (17:06):

My partner and I have systems in our relationship where we talk through things or systematic words that we use when we don't want to talk about something or whatever. It's a system much like any system that you have in your business or your life. I think a lot of times especially in high growth businesses or new business owners there's a lot of reactionary reactioning. And the reason that you prepare and get ready even if you don't think you'll ever need it is so that when the thing happens, you're not operating as much from the reactionary place.

Lauren Caselli (17:44):

So for me, like I said, I had the system of grief of dealing with hard things. I employed it, deployed it. Here I am. It's almost October 1st and much better. I just had a great launch and moved in a different direction even with taking about two and a half months off.

Susan Boles (18:04):

I love that. Is it worth it? Every small business owner wants to know that the money they spend on their businesses is worth it, that their investments produce results and help them grow. But if you don't know your business finances in and out, it's hard to know whether those expenses and investments are really worth it. Plenty of business owners, even the successful ones feel like they're shooting in the dark when it comes to how they spend, save, and invest their money. Like you, they wonder if the ads they're buying, the software they're investing in or the people they're paying are really paying off and that's stressful.

Susan Boles (18:48):

Feeling unsure about how you're spending or investing your money might be common, but it sure isn't fun. I want something different for you. I want you to feel confident that every decision you make is guided by your financial intel. I want you to be able to decide what actions to take to grow your business from a place of confidence and purpose, not panic so that you can feel masterful at managing your money instead of inept or just plain scared.

Susan Boles (19:16):

I want you to know exactly what's working so you can go all in and make your money make more money. This is what I do for business owners when I step in as their chief financial officer on demand. I help them parse the numbers, look for opportunities and invest where it counts. We get clear on where they're getting in their own way and where the math just doesn't add up. And now I want to teach you to do the same for your own business because trust me, you can.

Susan Boles (19:45):

Join me for Think Like A CFO. It's a four-month accelerator online workshop and small group coaching program where I'll work alongside you so you can start thinking like a CFO and know that every penny you spend on your business is worth it. You'll dig into your relationship to money, put your financial data at your fingertips and build systems of cash flow, taxes and budgeting. I'll help you integrate your financial knowledge into your operational systems and technology so that your whole business works better and by the end you'll feel wildly capable with your money. Think Like a CFO is starting soon so go to scalespark.co/cfo to get all the information and sign up. I can't wait to work with you.

Susan Boles (20:36):

I definitely do want to talk about the thing that you launched. Let's talk about the financial part of this shift, pivot, transition, the part that's had to deal with, I'm not going to work for a couple of months.

Lauren Caselli (20:51):


Susan Boles (20:51):

So what happened there for you?

Lauren Caselli (20:57):

That's a good question. I really try to be transparent about the financial stuff. In maybe year three of my business, I had seen some high growth. I had done all kinds of networking and charged more and did the whole thing and I still didn't feel like I was making any money. So I'd done a bootcamp with a guy who's local as a CFO and we spent 10 weeks together. He literally explained to me like this is a P&L. I was three years of my business. By the end of that, the one thing that I took away from it was like, "It is costing you money to run a business. You can get a job and make more than what you are making now."

Lauren Caselli (21:37):

So you either have to love what you are doing enough to be burnt out and stressed out about the money piece or you need to fix something. I don't think that we are often that honest with ourselves around what's going on in our business, and that was a real gift to me because then he taught me the basics, which is great. You can take any 12-week course. But what I started doing was really going deeper into why it had taken me three years in business to really take a hard look at my financials.

Lauren Caselli (22:11):

A lot of that was emotions. So a lot of that was how I felt about money. I think particularly for women... I don't love generalizations, but I think particularly for women we are told so many things about how we are supposed to interact with and around money. And I see this a lot with my clients, my current clients and I see this a lot in the communities that I spend time with is there are a lot of really strongly held beliefs around money that are just really reinforced stories that are being told.

Lauren Caselli (22:48):

We see this a lot of times particularly in like the female business owning space. I see this a lot on sales pages whenever I read someone saying like one of the objections is let me ask my husband if I can or my partner, generally, male partner if I can afford this program. I always think that that is like such a gut punch because I'm like there are... As if someone else unless they're a partner in your business, as if they know more about business finance without being a business owner.

Lauren Caselli (23:19):

So I don't remember the original question, but the point I'm trying to get to is I think we relinquish a lot of control around business finances because of the stories that we're told as women business owners. So one of the things that I have gotten really good at is retelling those stories and that has allowed me to both make more money, but also prepare financially for situations like this. This was the perfect storm. We both lost our jobs. I have a mortgage and it was fine and I got to take two months off. Great. So how do we engineer that for more women to be able to be in control of their finances because they're not... The stories aren't true. You're perfectly capable of understanding your money.

Susan Boles (24:04):

Absolutely. And it's really interesting because when I was doing customer research before I started Think Like A CFO, my group program, I did customer research calls with women and with men. It was really interesting because I was doing them at the same time and I've never really done research like this where it was all happening all at once. One of the things that was almost universal was that women especially felt really incompetent when it came to their money. When it came to their money issues, almost universally whether they were actually good with their money or needed to do some work, whether they actually really had systems and process and that sort of thing, they still felt like crap when it came to how they were managing their money. It was interesting because the guys when I talked to, still felt pretty incompetent, but they wanted to hire their way out of it, right?

Lauren Caselli (25:07):


Susan Boles (25:07):

So the women wanted to learn and feel competent and I'm not sure that... And the guys just wanted to hire somebody to take care of their problem. They didn't have that need to make me feel competent. They were just like, "Yeah, this isn't my strong suit. I'll just hire somebody and it'll be fine."

Lauren Caselli (25:30):

Right, right.

Susan Boles (25:31):

And it's really interesting that it was such a... I didn't expect that dynamic and now I've been seeing it everywhere.

Lauren Caselli (25:40):

That's so interesting. I'm so curious about that. Now, I want to look at your market research. I think, it's really interesting particularly... Man, I think they're... Particularly around money, they're... It's one of the things... Especially when we talk about business, it's one of the first things that we try to outsource, right? We try to outsource bookkeeping. We try to outsource accounting. Those are the first things that we always try to outsource. And I'm not saying that it shouldn't be the first thing to outsource, but what I am saying is we are so fast to relinquish control of our money because we don't feel like we understand it and that simply is not true. It's not true.

Susan Boles (26:17):

It's not true.

Lauren Caselli (26:18):

Yeah. Money is complicated but no more complicated than like writing an email funnel. It's that thing.

Susan Boles (26:23):

There are so many similarities. Every time somebody is like, "Oh, yeah. I'm totally comfortable with marketing and an email funnel and figuring out the system." You know it's exactly the same with your money like we'll just change the names here on your funnel. We'll start talking about income and expenses and profit instead of top of the funnel, middle of the funnel, bottom of the funnel [crosstalk 00:26:46].

Lauren Caselli (26:47):

So much of that is like we come to the business table with zero knowledge about... Let's say an email funnel. I have very like limited knowledge about an email funnel, but there's no story about what an email funnel says about you. Whereas it's not like-

Susan Boles (27:00):

There's not as much emotional tie to that.

Lauren Caselli (27:02):

Yeah. There's no sort of like judgment. Right? We come to the table with so many thoughts and ideas around money. One of the things recently that I personally have been exploring is not only like personal finance and finance worlds, at least in the financial advice world. Obsession with lack of debt, but also with the bigger picture if you look at large consulting firms or venture capital. All of these companies that essentially run our country have massive debt, right? And they leverage it.

Susan Boles (27:36):

Oh, they're awful. They're awful.

Lauren Caselli (27:38):

Yeah, and they leverage it in a way that... I'm not saying like go and take a bunch of debt, but I think our education around what debt looks like in the business world just needs to be more. So if you're on the hill of like don't have any debt, and this is something that I've always been on the hill... That's my hilt that I'll die on like no business debt, but then when I... For example like the idea loan. That was a 30-year loan at what like 3%. When I think about like, "Huh, it's either me closing my business or taking out a loan at 3% like maybe, as a worst case scenario that's something that I could leverage, which I didn't have to, but the stories that we tell ourselves and the stories that are in popular culture, I think constantly have to be evaluated particularly around money. So that's where I'm at about... Well, dead is the story that I'm greatly trying to reevaluate, but yeah.

Susan Boles (28:27):

I mean, I think you're right. I think every aspect of your business finances have nuances. There are nuances to the debt discussion. There are times in your business where it makes sense to use debt to grow your business. There are absolutely times where that's the right choice. We're so tied around our personal money stories, the online entrepreneur money stories, the hustle culture stories, VC, they all play into our feelings about money.

Susan Boles (29:06):

I think a lot of it stems from just we don't teach financial literacy at all. In any scenario. Not personal financial literacy, not business financial literacy, but I think when you have your own business, it becomes particularly pertinent because your business finances affect your personal finances and your understanding of how those things work impact how successful your business can be.

Lauren Caselli (29:39):

For sure, 100%. I also think that a lot of people... Not only do they delegate it, but they also... The proof of the prevailing wisdom is once I make more money then I will figure out what to do with it. I mean, that is an option.

Susan Boles (30:00):

It's maybe not going to be the fastest pathway.

Lauren Caselli (30:03):

Yeah. And here's what I'll say, just being in lots of masterminds and groups of people, there are people who are making a ton of money who don't know what to do with that, and it greatly affects their businesses. It greatly affects their personal lives and that is not a judgment. It's more an encouragement to say, again, get ready to stay ready. Once you rather make all the money like have a huge great launch, and know exactly what you're going to do with it rather than buying a boat and then being like, "Oh, wait. I couldn't afford that or whatever."

Susan Boles (30:33):

Do you not have a boat?

Lauren Caselli (30:37):

That was the first time I did it.

Susan Boles (30:38):

I of course have a boat, a yacht.

Lauren Caselli (30:41):

A business boat.

Susan Boles (30:42):

It's a business boat. It's a deduction.

Lauren Caselli (30:45):

Right. For my yacht trips, my business yacht trips. I think business money, personal money, it's always something to be working on. And it's probably, I would say, as you know... I'm sure you see lots of this with your clients, but just for me, with my money club and friends that I work... People don't actively work on their money and honestly the advice out there for business owners is paltry and sad, I would say. A lot of personal finance and business where financing in general is focused on the W2 employee, and that makes it really challenging to be able to do some of this research and this work to get better at your money.

Susan Boles (31:29):

Yes, absolutely. So as you were managing this whole transition and all of this grief, did your feelings around money or what you decided to invest in change at all?

Lauren Caselli (31:42):

Yeah. For my business or personal, or everything.

Susan Boles (31:46):


Lauren Caselli (31:48):

It's a good question. My money personality is I like to make big, big investments while I can be focused on...One of the big things I like to talk about is intentional spending and making sure that my spending aligns with the goals that I have for my life and for my business. So one of the things that I have gotten good at, I was not always good at this, but one of the things I have gotten very good at is recognizing when a decision is made out of fear or boredom or apathy, or to cope versus this is moving me closer to the goal that I wanted to move to.

Lauren Caselli (32:30):

I really had to double down on that during the pandemic because obviously there were less dollars both personally and in business. So I needed to be sure that every single spending decision that I was making was moving me toward my goal, which at the time was not working and grieving. So again, that's why I employed my therapist and our couples counselor because I was like this is going to help us move toward the goal of moving through our grief. So that's on the personal side.

Lauren Caselli (32:58):

And then on the business side, I really checked in with a lot of my softwares and I was selling some courses on autopilot that were bringing a little bit of income and that was all fine, but the things that I really doubled down on was I did a lot of education. So I took an email course that was excellent and I finally had the time to actually focus on it and do it. And just from that email course, book three, new coaching clients in August.

Lauren Caselli (33:29):

So within a month of signing up for that, that ended up... I ended up being able to make my money back immediately. And then I signed up for a group mentoring program with someone that I really admire and that helped me move through this launch and it was far more successful than I thought it was going to be. It was definitely scary, because my bookkeeper said, "Don't spend any more money." And I was like, "Great."

Susan Boles (33:56):

Great. I'm going to go invest money.

Lauren Caselli (33:58):

Fantastic. Business owners skills never go away. So I just knew now that I had an abundance of time and abundance of focus and abundance of one goal was to get clear. I was like, "What's going to help me get clear?" And that was writing to my list every week and processing in real time. And being in a group of other female business owners who were doing the same thing that I was, trying to figure out where they wanted to go.

Susan Boles (34:27):

So both of those investments paid off. I did have to cut my salary in half, both of those months. But again, those were decisions that I was comfortable making because I knew that I could take this thousand dollars for this course... Or not course, coaching program and turn it into... It ended up being turning into $9,000 for this program that I launched. But I knew that I could do that whether it was immediately or in the near future. I knew that just having that support was going to be positive for me.

Susan Boles (34:57):

So those were the decisions that I was making. So a lot of support from sort motivation, a motivational sense and being in community with people who are trying to figure it out and then support in my personal life. And those were things that I knew in the short term... I had no long term goals. I was like short-term goals.

Lauren Caselli (35:16):

Short-term only.

Susan Boles (35:17):

Get through grief. And what I had to do was get my support systems around me. So was there anything you consciously decided not to spend money on?

Lauren Caselli (35:25):

That's a really good question. Gosh, what did we consciously not spend money on.

Susan Boles (35:33):

Or specifically that you decided to cut.

Lauren Caselli (35:36):

Like costs on... Yeah, I transferred my... Well, I did this before the pandemic. I tried to systemize things a little bit more so I tried to put softwares in place to just make processes a little bit easier primarily payroll. Not that, that needed to happen this year, but I really was like taking a look at software. This was like the first year where I was like, "Oh, I can't hire staff right now." I was not really hiring even though I would love to have help. I was like I'm not in a place where I need to be hiring help because I don't know what I'm doing."

Lauren Caselli (36:15):

So I can't delegate things until I really know what the heck I'm doing. So in that place, I opted not to spend money on one-on-one personal delegation help and instead systemize things that I could set up a tech automation to do. So again, that was like a much cheaper decision. And in my head I was like, "I'll do this for a little bit." But now that I've created the system, I'm like, "This is amazing. Now, I don't have to..." When someone pays for a coaching program, it does all the intake and onboarding automatically, which was a great consequence of having to figure out all the automations on my own.

Susan Boles (36:56):


Lauren Caselli (36:56):

I would say sadly, I would love to employ people but currently it's just not... I want to be able to give people a commitment and until I smooth out the income, I really can't commit to someone. Although, I feel like that's coming soon.

Susan Boles (37:10):

So speaking of coming soon, tell me all about the thing that you launched.

Lauren Caselli (37:17):

So I feel like I have to back up a little bit. I had started this iteration of my bit. I started my newsletter. My newsletter, that's a funny word. It started, my email list in 2015. I guess, it was called the newsletter then. I had also launched a group of female business owners in my town where we got together and met once a month and talked about business, and that was very revolutionary. This was the time where I think like the wing had launched. There's a lot of women's group type stuff. But I had launched that in 2015 as a small group that was just for free and we met once a month.

Lauren Caselli (38:00):

They all really loved it and sort of was like, "Can I bring my friend?" I was like, "I can't host 20 people in my studio." It's not going to work. So I ended up creating a live event out of it and selling it, and it would sell out a bunch. So it was sort of my lead magnet. At the time I didn't know what it was. It was just an event that I was hosting and I ran it four times that year and three or four times the following year and maybe three times. Then my business grew from that sort of notoriety of being an event host to the point where I didn't have time to host it anymore and my business was taking off with that as sort of the catalyst.

Lauren Caselli (38:37):

But I had created an email list for those people and I had been writing to them on and off for the last since 2015. So this year, the one thing that I did do even though I told myself that I wasn't going to work is I wrote a weekly-ish, mostly weekly newsletter to this group of people. I never sold to them rarely. I rarely sold to them because my clients were in tech and these were not the people on the list. And for years I struggled. I was like, "I got this list and I don't sell anything to them and I don't know what to do with it." Do I switch? Do I focus?

Lauren Caselli (39:16):

It was just this thing that really didn't add to my business. I did sell some courses to them about event planning, but certainly not... That wasn't the audience for the email list. So flash forward to 2020 of July, I had almost 3,000 people although I did do a call and now I have maybe 1,600. But I had almost 3,000 people on this list from a variety of things and I took this email course and one of the things in the email course was like pitch an offer to people. You don't have to have it like completely done, but pitch an offer to people and just see what happens. If you get on a sales call with them and you see what they need and if you can help then you can create the offer in real time with them. And I am a big fan of that.

Lauren Caselli (40:07):

I can help in a variety of ways, but sometimes I don't know how I can help until I can actually get on the phone with someone. So I did that. I wrote this email and I had done one-on-one coaching for a long time. I obviously talk about money all the time and that's why people get on my list is because they want to hear someone else talk about money. And that's also why people unsubscribe because sometimes they're like, "That's too much money talk." And I'm like, "Great. There needs to be more."

Lauren Caselli (40:32):

So I had put it out there and I said, "Look, I'm doing three months coaching. We're going to evaluate the finances of your business in a very high touch way. Mostly like where's your money coming from, what are your average invoices and how do we make them more than like $750? So that you can actually pay yourself. Because my community has a lot of service providers who work on an hourly or retainer model.

Lauren Caselli (40:55):

I think you've done a podcast episode on this. I just can't remember who. It's challenging to do an agency model when you're one person because there's so much time overhead in invoicing and all kinds of stuff until you really get it systemized. You're wasting a ton of time doing the administrative work of hourly work.

Susan Boles (41:15):

Almost generally always, you're wasting a ton of time if you're doing hourly work.

Lauren Caselli (41:19):

Yeah. I knew that and I had switched my business to doing high level packages maybe like in 2018, 2017. I stopped doing hourly work for sure. And that's very common in event planning. It's not hourly work, it's very package based. So I put it out there. I said, "I'm taking four clients." And I booked four clients almost immediately in probably two or three weeks. Then I was like, "Oh, I'm on to something here." So what that led into was working with those clients over the ensuing two months and realizing that I was essentially taking them through the same process, which was, "Get your mind right about money and let's talk about what it means to make more money and make a lot of money and charge a lot of money." What does that mean to you? And that is usually the first hurdle. It's not like the tactics behind it, but what does it say about you?

Susan Boles (42:12):

Getting your brain wrapped around sending an invoice for five figures.

Lauren Caselli (42:17):

Yeah, totally. So a lot of it was just the emotional work that I had been slowly working on, but a lot of people just need someone else to give them the permission that A, you're not going to price yourself out of... It's nearly impossible to price yourself out of the work that you're doing. I work with service providers and particularly someone who worked in tech. The things that people pay for is a lot.

Lauren Caselli (42:45):

So I have that data knowledge of what specific industries are willing to pay for and now it's just me saying like, "Oh, you're targeting this audience." For sure, they have the ability to pay you this. And let's lead with that instead of leading with the hourly work, which you can always lead into later if you want, but let's make our average client value more than just $750, short project. So that's what we work on.

Lauren Caselli (43:11):

So the first step is let's get our mind right about sending a $10,000 proposal and then the second piece is how are you making sure that you're delivering on the value and the expectation that they have. So it's building out that service package so that they feel good about selling it.

Susan Boles (43:26):

Oh, I love that.

Lauren Caselli (43:27):

Yeah. I love it too. It's so fun.

Susan Boles (43:32):

That's the part that I think ends up being really cool when you take a break and you suddenly realize like, wow, this thing, I didn't realize was a thing is now a thing and I love it.

Lauren Caselli (43:42):

Yeah. It's funny because I used to get off event planning calls and events is a very meeting heavy industry because you're trying to like herd all the cats and so you're just trying to get people to get on the phone with you so that you can get answers from them. So I used to be so drained after all of my event calls. And now, I'll have a call with a client and they'll be like, "Here's what I'm struggling with."

Lauren Caselli (44:01):

I will just ask them the questions that they need someone to ask them and they'll be like, "Oh, well. I don't really know. I haven't had time to work on it." I'm like, "Okay, well, let's work on it right now." I will be the receptor. They'll talk it out. I'll be the receptor and I'll be like, "Okay, you just wrote your service page in an hour. We just did it." After months of them struggling with the thing, that they're trying to work on.

Lauren Caselli (44:25):

It's so fun at the end of the call to get off and be like, "We really made a change. We really did a real change to be able to actually help you sell better, sell more, position yourself as an expert." And that is so gratifying because I want women to make more money specifically.

Susan Boles (44:43):


Lauren Caselli (44:43):

More, make more. So that's what I'm doing now. I booked four clients in August, almost in a couple weeks and then launched this process as a group process in just recently, what the heck was that? September. And we start this week. So this is like what I'm thinking about, what do I do? I help women make more money, but then the next step is, "Now, can we figure out what to do with it in a way that's in alignment with our values." I just think that that is the big gap in the education of being a business owner that has a healthy business.

Lauren Caselli (45:26):

The next step is like, "Okay, how do we make these financial decisions that both impact me, impact my team, help create jobs?" Whatever. Align with the values that I have and I always feel like programs sell you the after. They're like, "Here's what your life can look like." But it doesn't tell you.

Susan Boles (45:42):

It doesn't tell you that like-

Lauren Caselli (45:44):

How to make the decisions to get there.

Susan Boles (45:45):

Making the decision part is really murky and it's really individualized. You have to understand what's happening. You can't follow a framework to make financial decisions in accordance with your values because somebody else's framework is going to be according to their values and their business.

Lauren Caselli (46:03):

Yeah. And I see this all the time. In Facebook groups when people talk about money, I mean a lot of those and just a lot of it is... Well, I would never do that. And the reality is it's like great.

Susan Boles (46:14):


Lauren Caselli (46:16):

Fantastic. I see a real sort of like... I remember when I was like at the very beginning of starting to make money in my business make real money. I was hungry for trying to figure out what to do with it. And I, at the time, I didn't have a partner, a male partner or any partner. I was alone. I was single. I didn't have a business partner. So the decision-making was firmly left up to me.

Lauren Caselli (46:42):

I wanted to know what other people were doing with their money. And there was like not really a forum to do that. So I don't know. That's kind of what I am hoping there to be more of is that we all have more forums to be able to talk about money, so that we can crowdsource the decision-making piece with a group of safe individuals who aren't going to be judgmental and say things like I would never do that.

Susan Boles (47:08):

I love that. So we are just about out of time. So where can our listeners find you if they want to connect or learn more about what you do?

Lauren Caselli (47:15):

Yeah. So my website is laurencaselli.com and I hang out the most on Instagram @laurencaselli_. But my best stuff is in my email which I have like a PDF for starting the journey to have better money conversations with your community, with your partner. And that's at laurencaselli.com\etc.

Susan Boles (47:39):


Lauren Caselli (47:39):


Susan Boles (47:40):

Awesome. Thank you so much for being here. I always loved that.

Lauren Caselli (47:43):

Thank you.

Susan Boles (47:43):

This is always my favorite.

Lauren Caselli (47:45):

Yeah. It's been fun. Thanks for having me.

Susan Boles (47:48):

Lauren's investment in building up a cash cushion before the crisis hit, had a huge impact on her being able to take some time off, see how the crisis really rolled out and then make strategic decisions about what to do next from a calm place. And that's really what having a cash cushion or cash reserves is all about. It's about buying you time to breathe and to process, so you can react calmly and strategically because no one makes good decisions when they're panicking. A cash cushion equals time and calm in a crisis.

Susan Boles (48:24):

Next week, I'm talking to Alethea Fitzpatrick, a diversity equity and inclusion consultant. And we're talking about how she's managed the change in her life and her business this year, when her business really started to boom. So hit subscribe in your favorite podcast player so you don't miss it.

Susan Boles (48:42):

Break the Ceiling is produced by Yellow House Media. Our executive producer is Sean McMullen. Our production coordinator is Lou Blazer. And this episode was edited by [Marty Seefeld 00:48:52] with production assistance by Kristen Runvik.