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Lauren Black on How to Choose the Right Business Investments for You

Hailey Dale


I’m Hailey – content strategist and founder here at Your Content Empire where we help you create more profitable, purposeful and productive content — and hopefully enjoy yourself more while doing it too. Learn more about me here >>

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Lauren Black on How to Choose the Right Business Investments for You

Avoid Buying Anything You’ll Regret This Black Friday

How’s your inbox looking? 

I know in mine, Black Friday deals are coming in hot and heavy. 

So I wanna send you a lifeline. 

This week, I had decision expert Lauren Black from Anchored Decisions on the podcast to get her help on how to avoid buying anything you’ll regret this Black Friday (and beyond). 

Here’s what we’re covering this week’s episode:

  • The SAIL Method: Lauren breaks down decision-making into a cool process called SAIL. It’s all about knowing yourself (hello, self-awareness), checking how choices affect you (Impact), and that final gut check (Litmus test).
  • Oops, I Bought It Again: Addressing the emotional impact of impulsive purchases and strategies for overcoming regret through reflection and learning from experience.
  • Getting Smart with Choices: Need help deciding? Lauren’s got tips like using decision guides, asking others for real talk (because sometimes we need that outside view), and focusing on what really moves the needle forward.

Find Out More About Lauren Black from Anchored Decisions:

About Lauren Black: Lauren is the owner of Anchored Decisions, which helps overthinkers make easier decisions through one-on-one decision coaching and strategic decision guides. Lauren believes that better decisions lead to a better life. Her signature framework, the SAIL Method, provides a 3-step process for determining your best course of action so you can make confident decisions and live with purpose.

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Hailey: Welcome back to the Content Coffee Break podcast. I'm so excited to be here with my first guest ever on the podcast. Excited to be talking to Lauren, who is the owner of Anchored Decisions, which helps overthinkers, like myself, make easier decisions through one-on-one decision coaching and strategic decision guides. Lauren believes that better decisions lead to a better life. Her signature framework, the SAIL method, provides a three-step process for determining your best course of action so you can make confident decisions and live with purpose. Thank you so much for being here, Lauren. I so appreciate it.

Lauren: Thank you for having me, Hailey. I'm excited to be your first guest.

Hailey: I know, right? I haven't been doing a ton of guests and you were the very, yeah, the first person I talked to. We were talking a little bit before this, but, oh, I'm just, yeah. Introduce yourself. Tell us a little bit about you.

Lauren: Yes. So, I used to be the world's worst decision maker, not as far as making bad decisions, just slow in making decisions. Overthinking constantly, changing my mind, and once I became a mom, I realized how precious your time is and that I couldn't just keep switching business ideas and changing my direction and changing my mind on things because I would spend all this time heading in one direction and then change it and go a different direction and I just had to have a better framework, something that could make decision making easier and, you know, something God laid on my heart as well to help others who are like me to be able to make easier decisions because it doesn't have to be as burdensome as we feel it is.

Hailey: I completely resonate. I relate to that. I think we met way, way back when we were in a mastermind originally together and I felt such a kindred spirit with you because I felt like we were people who kind of like, even though it was like an innovators mastermind, like it was like to come up with new ideas. I still felt like I was really slow on the uptake and I felt, yeah, yeah. Just that chronic over-decision, overthinking when it comes to decisions. So, I really, yeah, when I heard about your new business, everything just clicked. It made complete sense to me that this is such a need for people out there, because whether it is slow to make decisions, not wanting to commit to one direction over the other, or just being overwhelmed completely by all of the options out there before you like, yeah, I want to know about like what led you to even start this business?

Lauren: Yes. So, back in the day, we're going to go way back to 2017 when I was running my design business full time, Legacy Loft, and was burning out from being a one-man show. And so, I sat down to figure out what are my strengths, my weaknesses, what have I been good at in the past and had success with? And I realized I didn't really want to grow a team. And I didn't really want to do a one-to-many service for graphic design. So, I was like, okay, maybe a product, and realized that I'm really good at breaking things down, reverse engineering problems, helping people ask the right questions to get to solutions. It's something I had done with my brand clients, with my brand guide that help people determine what their brand should look like and feel like. And the whole messaging and visuals. So, I'm like, okay, I can turn this into a product and make workbooks for people. And I, in that same mastermind you mentioned, had come up with this idea of a business vacation, and that people would go through one of my business workbooks to help grow their business. So, I named it Bosscation and was going to add this whole box that was like a business retreat in a box of all sorts of items for planning and relaxation to take away. But I realized in the end, just as I launched that business, just as I had my first son, that it was all about the box and it should have been about the workbooks because that's where the gold was. That was the content that people were raving about. But I made it about this Bosscation instead of about the workbooks. So, I had kind of shelved that idea, set aside those workbooks, and focused on just the design work while I had my babies. And then more recently, just the idea kept popping back up of doing these workbooks that help people with certain things. But I was like, I need a topic that people really resonate with, that will really be helpful, that's not something that's overdone. And that's when that God moment of Him putting it on my heart that okay, decisions. And I was like, but I'm horrible at making decisions. And that's when it hit me that wait, that's because there isn't a resource out there for people like me. I mean, there's books and there's podcasts, but nothing that is specific to every decision you make. And so, that's what I'm looking to do, of having these decision guides that take my reverse engineering style, take my problem solving and asking the right questions. I came up with a framework that I've used. I'll test it with others, and it seems to be super helpful to really walk you through and make those decisions easier, and then you can apply it to every single type of decision to help you just work through it. And feel confident that you're making the right decision because that way you don't feel tempted to flip-flop and to go back and try to start over when you aren't 100 percent sure, or you were confident and now… Yeah. Someone questions you and rather than having this confident answer of these are exactly the reasons why I made this decision, now you start questioning yourself and you start to go back.

Hailey: Let's dive into the SAIL method. I want to hear a little bit about it. If you can give us some teasers on exactly what it is and how that process of reverse engineering that decision.

Lauren: Yes, so this is SAIL as in S-A-I-L. I know when you hear audio, people might think S-A-L-E. And so it's a three-step process, and sometimes people will go through the first step or maybe already know their decision, but if you don't, there's step three. So, step one is the S-A, and that's self-awareness. So, really knowing who you are, what you stand for, your values, your personality, how you work well. And if it's for your brand, you should know your brand values, your brand mantras, and what your brand stands for, what you want to represent in this world. And so that's all the self-awareness that's the foundation of this decision. So, if the decision option does not line up with who you are and what you stand for, then it's already a no. And then the I in SAIL is for impact. So, this is, how do these options impact your life? And I've detected five key areas that you examine: financially, physically, emotionally, relationally, and spiritually. So, if you can kind of check off, okay, does it meet these boxes? Does, how does it affect me in these areas? Then you just kind of dive a little deeper into that decision and how it impacts you. And then the final one is the L, and that is your litmus test. So, if you haven't already figured out which decision to make, you run it through the litmus test. And for me, this is deciding what is your top priority and which options line up with your priority the most, and you kind of have to pull from the S-A and the I to really figure out what your priorities are. So, that's why you set that foundation of knowing yourself really well, knowing your brand, and that way you're able to figure out those priorities and see what lines up.

Hailey: Yeah, and I can see how this would help with all sorts of decisions. It doesn't just need to be business ones. What are some of the decisions that you have used for yourself?

Lauren: Yes, for me, the biggest decision that I kept flip-flopping on was, should we have another kid? And I needed to go through, I'm like, this, this will be the biggest test of this method and to see if my decision guides actually work. Because if I could solidify my decision on whether or not to have another baby, then you know, it works because I was very, very torn on that for a long time. There've been people who need to decide whether to purchase that car or this car and whether to actually sell their car or just keep, you know, maintaining an older car for now and then home buying as well. And then within business too, there's, you know, should I have this service or that service? And should I purchase that course or not?

Hailey: Which is perfect because there's the whole other side of decisions like we've talked a little bit about the overwhelm and the indecision and the overthinking, but then there's also the whole other side of the coin where maybe decisions are made a bit impulsively. And this falls on this, like, Black Friday week that I need a guest in here and have my first guest on the show. And I'm like, what is happening on Black Friday? Well, we are being bombarded with sales messages and offers and courses and masterminds and coaching and all of these things coming at us and like really great sales copy telling us all why we need it. That's going to be, I think, really easy to be swayed in, you know, maybe buying or investing in a lot more things than maybe we need. Rather than slowing it down and making an intentional decision. So, I'm curious how you see this method, maybe like coming into play, especially in this season where, you know, it's very easy to think you need X, Y, and Z if you're going to succeed at X, Y, and Z when really, you might not.

Lauren: Right. Definitely. I have already started getting ads for Christmas gifts for my kids and, you know, I was looking up podcasting courses or I listened to somebody's podcast on starting a podcast, which is something I want to do. And all of a sudden, I started getting all these ads for people's podcasting courses. And so, yes, the struggle is real. There is tons of content out there, all the ads. So, one thing that I want people to recognize is that you can either be proactive in these decisions and then you're purchasing, or you can be reactive. So, proactive is when you are intentional about ahead of time deciding what things you need for your life or your business and that way you can keep an eye out for the products, especially if you're able to narrow it down to the exact one you want before Black Friday, then you can wait for that deal and look for the best deal instead of waiting for Black Friday to come around and seeing what's out there before making those decisions. And I think if you are reactive where that's the impulse purchasing, that's the seeing it and then deciding, “Oh, I have to have this. Oh, there's a countdown timer. I need to purchase now.” That's when we get a lot of that buyer's remorse.

Hailey: Yeah, so maybe if it wasn't, like, you shouldn't be waiting for the ads to tell you what you need. You should go in knowing that kind of ahead of time. Do you have any tips for how people can slow down that decision-making process when they're feeling really pressured?

Lauren: Well, I think writing things down is a big help. Journaling and just making sure it's on paper. And then I really do feel like the SAIL method will help you with that to take that proactive approach. So, if you want, I can walk people through using the SAIL method for these.

Hailey: So yeah, I would love to do that. Okay, coming up to Black Friday, there's a great deal here. Walk me through how we would use the SAIL method for making that decision ultimately.

Lauren: Yeah. So let's start with the self-awareness and start looking at what are your actual needs, either currently right now, or one that you foresee coming in the near future, and look at, kind of take it a step deeper to see, is this actually a need or is it a want? And if it's a want, that doesn't mean you can't purchase, but I know recently in October, my friends and I went through a contentment challenge, and I was challenged to have no unnecessary spending for the month of October. And once I started in it, I thought it would be super easy. Like, okay, yeah, no chocolate, but it's Halloween. So my kids are bringing home chocolate anyway, or, you know, no buying clothes for me. But then you start thinking, okay, my vacuum died. My vacuum. And is a vac mop a necessity? Well, technically, I could wash my floors by hand for the month of October. So is that really something I need right now or not? So really consider when you're looking at a course or coaching program or a software, is this something I really need? And do I need it right now? And if it is, then you can kind of go into, okay, which one, and you'll be able to look at that better. But if it's not, then the self-awareness, you want to look at, okay, if it's a want, why do I want this? What are the benefits? What is it going to be helping with? You know, if you're looking at your business, think about what's helping you move the needle forward in your business. And sometimes we think that something will help. Okay. You know, maybe having a social media manager might make your life a little easier, but if there's something else, maybe a salesperson, that will help you bring in more money, then that should be your focus. So start to recognize. You know, is this because of FOMO or is this an actual need? Is this a desire for status because everybody else has one or these influencers you've seen have this or purchased this? Or is this something that's beneficial? You know, do you have an emotional attachment? And then also in this self-awareness section, look at how your personality is or your track record. So for me, I never finish courses. Pretty much never actually go through all a course that I bought start to finish, and I told myself I'm never buying a new course. Well, I did buy a course this week because it's for something I actually need, and I know it's for launching a podcast. I know I'm launching a podcast coming up, and so that is a need, and I'm committing to.

You know, changing my brain to actually finishing this course once I dive in, but if you kind of look at your track record, like, okay, do I do better in a group setting? Do I do better with one-on-one? Or if it's a software, is it something that you buy software or apps all the time and never actually implement them. So look at kind of your past to see what a good fit is for your future. And then we move on to the I, and this is where for these purchases, you'll probably spend a lot more time in. So we'll dive into the five kind of sections of what the impact is. Yeah, the first one is financially. What are the costs? Look at short-term and long-term and, you know, if there's a monthly yearly fee, what's that fee going to be after this promo ends? Because a lot of times you lock yourself in at this great Black Friday rate for a year, but then can you maintain that price moving forward? Or look at what are the ripple effects. So let's say you decide to move your website to Shopify. Well, now you might also need to buy Shopify. You might need Thrive Cart. So there are other kind of ripples of these purchases that you need to calculate financially.

So, then the next one is emotionally. So this, when it comes to business, things might be, what do you really dread doing in your business? Is there something you put off and you know you should work on, but you just hate it and so you don't do it and you know you need to. So those might be good things to seek out a solution for that issue and, you know, does it make your life easier? Does it make your life more enjoyable? Does it give you peace of mind? You know, maybe it's business insurance for a physical product company, you know, maybe it's going with a better supplier for somebody. And so whatever can emotionally help you to feel more at ease in your business or to be able to enjoy life a little more because we're entrepreneurs so that we can enjoy our time and decide how we use it, which leads us to physically so physically, do you actually have time to use this product or service to implement it? You know, if you're buying a Facebook ads course, and you know, you aren't actually going to start looking at it for 6 to 12 months out. Then that's probably not good timing because by then, who knows if the algorithm will have changed.

And then the next one is relationally. So how does this purchase affect the others involved? So maybe what could make you a better boss, or what could help with networking or community building? Last year, I purchased a Black Friday deal for a conference ticket, and they threw in a kind of door buster of a photo shoot. So I got free pictures taken at the conference, and that was perfect timing for me because I was looking at that conference, was hoping that they'd have a sale, and sure enough, they did.

And then the final one is you look at spiritually. So what type of soul care do you need? And how can you be in a healthy spiritual spot? So for me as a Christian, that's making sure I'm connecting with God first and foremost. So I don't want to load up my business or my schedule with things that are going to draw me away from that.

Hailey: I love that. And I think a couple of points that came up is like financially also thinking about maybe what the upside of investing in that thing is and what it could potentially mean in terms of sales and impacting your bottom line, like you with this podcast course. I mean, what are the costs for you of like figuring it out on your own?

Lauren: Yes, and I think people who take their time and they really know that self-awareness of what they need and kind of their track record of how they work. Once you make that decision, when it's been a very intentional one, you've done your research, you've looked at the reviews, you've read testimonials or you've tested things out yourself, then you feel a little more invested in this product. You feel more confident in it and yourself as a solution rather than just buying something on a whim that you're like, “Oh, this looks fun.” But then once you're you get really busy, I know for me, part of the reason why I've kind of failed to finish any courses is because they have a lot of them have been those impulse purchases and I just don't have time. There are other things that take priority and I didn't factor that in when I purchased that course and so therefore when you're emotionally invested, physically invested your time, when you financially are invested, and it's then a very wise, intentional purchase, those are the times when you do tend to use that investment a little better.

Hailey: Yeah. Do you have any advice for people who maybe they're listening to this too late, how do you deal with buyer's remorse? How do you deal with the impact of making a bad decision?

Lauren: It's funny. I'm actually in the process of writing a blog post on this, that by the time this airs, it'll probably be out there, but yes, I think we need to give ourselves grace a lot more than we do. And what is the point of remorse? Like living in remorse is not going to help you at all to be more productive, to move forward. So if you have made a bad purchase, then let it go and just keep moving on and learn from it. But you also need to look at what's a poor product or service versus an actual poor decision. So if you did do your research and you had seen testimonials and then you purchased this thing, and maybe it doesn't work out. Then perhaps it's not on you for making that bad decision. Maybe it's poor quality control. Maybe it's just a compatibility issue, or maybe it's something I started my website for Anchor Decisions on a platform that was a kind of do-it-all platform. And it seemed like it had everything. And from the reviews and looking at it, it seemed like a great choice, all in one. It had email. It had even some social scheduling. It had your, it could host my e-commerce and my website. But once I actually dove in and started implementing and set up my shop, which is sometimes you can't do everything in a free trial. So once I got going, I realized there were a lot of shortcomings that I didn't see and so sometimes you just don't know until you try something, but you have to try in order to move forward. You can't discover the good things if you didn't take chances. So just, you know, realize that you are going to buy some things, make some purchases that aren't good purchases. And if you recognize that maybe you are an impulse shopper and you're constantly buying things that you regret, maybe it's time for a change. And for some people, if you've put the effort in, you did the groundwork and it still doesn't work out. Well, give yourself a little grace, let that go.

Hailey: More grace. I think we all need more grace. Summing it all up, what are three kinds of decision-making quick tips to remember or questions to ask yourself when you're staring down a decision?

Lauren: Yes. Well, that actually brings me to, we never got to the L, which is your litmus test. Yes, the litmus test, which this is kind of, you know, those three big things in the end, but you, you want to know your priorities. So look at your goals, long-term and short-term and see, is this helping me reach my goal? What's going to, even if it's baby steps, you know, a lot of times we want to take this big leap and think that we can just, “Oh, this one course is going to get me to where I need to go.” Or this coaching program that's super expensive is the thing, but maybe we need to take those baby steps first. So what's going to get you to that next step and, you know, help you to make money, save money or save time. Which is essentially money. And then make sure you've done your research. So if you read reviews, do as many tests as you can, talk with people. You know, I've physically messaged some people when I've realized that there's a name that's a testimonial listed on someone's website for maybe a coaching program. I've reached out and said, “Hey, can you give me just kind of a 1 on 1? Here's my situation. Here's what I need. Do you think this would fit my needs?”

Hailey: I love that you mentioned that because I do think, especially in today's day and age, we need to do our due diligence. It is like way too easy to like stock that sales page full of testimonials, overpromising over promises made on sales pages. So yeah, due diligence, I can see more important than ever, especially in those heightened, fast pace, kind of like Black Friday, Cyber Monday, all the things, sales environment.

Lauren: Yeah. And reaching out to the owner too a lot of times, if it is a course or a, some sort of group program or something where it's one on one, a coaching program with someone, the owner, or at least their team is willing to answer questions. And if you can really feel them out, then that'll help you determine, “Okay, is this for me or is it not?” With that conference that I was looking to purchase. Because I had had my eye on it for a while and I wanted to make sure I was an actual good fit. For that conference. And so I reached out and just said, “Hey, here are the things I'm looking to get out of it. And here's my situation.” I wasn't an exact fit for her kind of ideal client, but I still, there was so much value that I got out of that conference that it was a good fit for me, even if I wasn't her number one target market for that conference.

Hailey: So to sum it all up and to circle back to those quick decision-making, either tips or questions like what do we want people to take away in terms of like what to ask themselves or tips for decision-making?

Lauren: Yeah. So really just know yourself well. And if that means journaling every day. And really evaluating who you are, who you want to be, and what's going to get you there. And that will help you to be able to set those correct goals for your life and your business and be able to take reverse engineer and take the baby steps to get you there.

Hailey: Awesome. And then where can people find you online? Where can they come hang out with you if they want to get their hands on one of those decision guides?

Lauren: Yes. So my website is Anchoreddecisions.com and I'm on Facebook, Instagram, and Pinterest at Anchored Decisions. And then I also do have a free quiz that is helping you how to decide what to purchase. Should I purchase this or not? This is kind of for something that you've already determined the one that you're looking at and just need that extra confidence of should I hit purchase or should I wait a bit? Or should I pass on this? So you can find that and other kinds of buying decision help at anchoreddecisions.com/buyersguide.

Hailey: I love that. How timely. So number one tip that we didn't add here is go and take that quiz. Well, thank you so much, Lauren. I so appreciate your time and you sharing all of your wisdom. So thank you so much for being here.

Lauren: Yes. Thank you for having me, Hailey.

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