5 Things I Would Do Differently If I Were Starting Over in Business

You're listening to The Jewish Entrepreneur Podcast with Debbie Sassen, Episode 148.

Welcome to The Jewish Entrepreneur Podcast. I'm your host, Debbie Sassen. I went from being a financial adviser, author and chronic under earner to building my business to six figures as a financial planner and money mindset coach. And then, on to multiple six figures as a full‑time money and business coach.

I help entrepreneurs create money making businesses and build wealth using sales and money mindset strategies in alignment with authentic Jewish values. Now, let's dive into today's show.

Hello, my friends and welcome back to the podcast. Today I have a very actionable podcast. I'm going to give you five things that I would do differently in my business if I were starting all over again from scratch.

And in a certain way, I am, and I think you are, starting your business from scratch. We are at the end of the Hebrew month of Elul. We're at the end of the Jewish calendar for the year, Rosh Hashanah is in just one week from today as this podcast drops, and we all are having new beginnings. And this is an invitation to you, to me, to look at our business with new eyes and really think about the coming year.

I mean, certainly in the Jewish calendar, the last year has been anything and everything but what we would have expected on Rosh Hashanah, on the Jewish New Year. A lot of people were thrown left and right, and a lot of it was unexpected because of the war in Gaza, which has also expanded to the north, to Lebanon, to our border with Lebanon.

But regardless of what's happening outside of us, we also have to focus on our business. I'm going to share with you what I would do differently if I had to do it all over again. As I was preparing this podcast, it was just so insightful to me how far I've come, and how many of these specific items I am still working on every day, every week, every month in my business.

So it doesn't really matter at what stage your business is, but you can always take something and tweak it and just bump it up a level.

Before we jump into the podcast, this is Episode 148, which means that we are almost at Episode 150. Wow, that is a big milestone for me, for you, my listeners. I invite you to send me emails. Tell me; what do you want to ask me? This is going to be an Ask Me Anything episode. So I'm inviting you, whatever it is, business, money, family, you want to know how we chose our kids' names, whatever it is, you are invited to send me an email at Debbie@DebbieSassen.com.

Let me know what you would love me to speak about on the podcast. Because I really want to help you wherever you are to figure it out. As a working mom of many… that is definitely a topic that I love to talk about, and we're going to address that a little bit today on the podcast. All right, so let's jump in.

I'm going to speak about five things that I would do differently in my business if I had to start it all over again from scratch.

The first thing that I would do differently is that I would have an email list from day one. Maybe not from day one, maybe from day two or three. When I started out as a financial planner, and I worked with a mentor… I worked with two mentors, actually…  we did many financial planning workshops together. We had people fill out all of their details.

I did this as well. Sometimes I gave them together with my mentors. Sometimes I gave them separately under the banner of the company that I was working with. I took all of these sheets of paper home. Now back in the day, that was over 16 years ago, we did a lot more work with pencil and paper than we do today. Today, there's digital, there's QR codes; there are very different ways of doing it.

I think it's very important for you to collect the names of the people that you meet, and put them somewhere so that you can stay in touch with these people. These are people who have raised their hands. They want information from you. This is whether you're doing a workshop or webinar. Webinars these days, people will give you their email because webinars are digital.

But it doesn't really matter where your people are coming from or where they've been. Start an email list, because there are a lot of different ways that you could market to your potential clients.

The most intimate way of being in touch on a regular basis with your clients, other than face to face, in person, is by email because people have to opt in. If you're listening to this podcast, you might be subscribed and you might listen to it every week. But I don't know, I don't have any feedback from you on a regular basis, unless of course you're rating and reviewing my podcast.

And this is an invitation for you to go and do that. Give me a five-star rating, give me a review on Spotify, on Apple, wherever you listen to your podcasts, so that we'll get out more. But I don't have any intimate relationship with you.

Similarly, if you and I know each other from social media, from Facebook, Instagram, LinkedIn, again, it is less personal than me being in your inbox on a regular basis. So if you do not yet have an email list, this is my number one takeaway that I want for you. That you find yourself an email service provider right now; press pause, go do it.

It's not important to me who you start with as your email service provider. Back in the day, I started with Mailchimp. Today I'm with ActiveCampaign. Who I'm going to be with tomorrow, next year, five years from now, I can't promise you anything.

If you are newer in business, find the least expensive email service provider and get yourself going, because that's the way that you can have a relationship with your people.

Which brings me to point number two. Debbie, how do I have a relationship with my people by email? I don't know what to say. I don't know what to do. What am I supposed to do with this email list now that I have it? How often do I have to communicate?

These are all beautiful questions; I love them very much. Email is a tool that you use for marketing. It's one of your marketing avenues, and again, it's one of the most intimate. So now you have to ask yourself, “Oh my gosh, how often do I communicate with my people?” I communicate at least once a week with the subscribers to my email list.

I have just finished up a launch for my group program, Wired for Wealth, and I was in touch with them multiple times a day, especially towards the end.

Also, if you're running webinars, then you might be sending reminders multiple times in the last day or two to remind people to show up and to be there on time and make sure that they have the links. But generally, if it's just you giving regular value to your clients, I recommend once a week.

If you are newer in business, that might seem like a lot. I'm going to give you the next step, and it’s exactly what you need to do in order to stay in communication with your people. Because you're going to be like, “I don't know what to say to my people.” So we're going to talk about content pillars.

But I really do recommend that you get yourself in the habit of sending weekly emails to your subscribers. Maybe you're going to do it every other week, because you're going to tell me that you can't do it every week. Maybe you'll tell me every month. My accountants, by the way, send me emails once a month, more or less.

And by the way, before Rosh Hashanah, this is an invitation to send to all the people on your email list that you may or may not have been in touch with over the last two, three, six months. Send them a Happy New Year card so that they know that you remembered them, so that they know that you exist.

Now we're going to go to the question, what do I send in my emails? Which is point number two, your content pillars. What are content pillars? Content pillars are basically the things that you talk about with your clients all the time. I don't want you to get scared away by this fancy word “content pillars”, but these are the topics that you talk about. These are the things that you help your clients with.

Back in the day when I was a financial planner, I might have talked about retirement planning. And because most people who are planning their finances, unless they're people who are trying to get out of debt or help their kids save for college, basically most of our financial planning was towards retirement, or towards buying a house or something like that. But I'm going to keep it very simple.

If I look at the basic thing that I talk about… And that's what I gave seminars on all the time when I was doing these live workshops. And then again, when I moved into virtual…  we talked about the difference between saving and investing. I talk about that in business as well.

Because if you keep your money in safe savings, it's not going to grow with inflation so that it's going to be able to take care of you when you're 65, 75, 85, etc. I could talk about risks, and how much risk you need to take in your portfolio, your investment portfolio, so that your money is going to grow and it's going to be able to take care of you.

Another topic, which would be a content pillar could be healthcare. Not that I am an insurance agent or healthcare provider, but as we age, our healthcare costs do tend to go up. So that would be another content pillar that I would want to talk about, and different types of healthcare, different types of insurance.

And of course, debt management would be another one of the content pillars. Because if you are in debt at any time of your life, that is going to impact the amount of money that you have in the present, and it's also going to impact the amount of money you are able to invest for the future.

So those could have been my content pillars, but nobody ever sat down with me, and I didn't have the brilliance to ask back in the day… or maybe I did, but I don't remember the answer… But that would have given me a structure to what I need to speak about in my emails on a regular basis.

And then I could have, for example, a month that was dedicated to investing, a month dedicated to savings, a month dedicated to risk, a month dedicated to debt management. I hope you're getting the idea. But that way, every single month I would have a topic, and I could prepare in advance for emails that would be specific to that category.

As a business coach, my topics are… some of them are similar because they're money related… but I can talk about marketing and, for example, if we just break down marketing as one of my content pillars, there's email marketing, there's social media marketing, networking… which is kind of an in-person marketing.

There's doing workshops and webinars, which again is a way to share your business with other people and invite people into your audience. And of course I speak about sales. So with sales we can talk about preparing for sales conversations, how to ask good questions, overcoming objections, closing the sale, follow up for sales.

Another content pillar of mine, which I think is really important, is your CEO mindset. How do you approach your business? Do you have a vision for your business? What's your purpose or your mission statement for your business? And are you showing up as a business owner or…? I like to talk about the difference between who you are and what you do.

Many times we go into our businesses… For example, if I was a financial planner, and I'm a person who's doing financial planning, I wasn't thinking of myself as a CEO growing a financial planning business. I was just doing the thing that I was doing. And so many of us have that, what I would call “employee” mindset versus “CEO” mindset.

We're just thinking that we do the thing we do. We show up at work, we do this thing, we get some money and then we go home. Whereas a CEO has to be more strategic and have a longer vision. So that's another one of the topics that I talk about.

For example, on the podcast, you can go and you can find some episodes that would be talking about future casting, your vision, your mission, and topics that go under CEO mindset. And of course, if you're running a business, we must be talking about money.

So those would be my content pillars. Those are my content pillars today: marketing, sales, your CEO mindset, and your money.

Part of the CEO mindset brings me to number three, which I would have done if I had had to do my business all over again today. I would focus on Sunday scheduling. Sunday is the beginning of my week; I work from Sunday until Thursday.

Sometimes I work a little bit on Friday, but mostly I don't. Especially as we now move into the winter months and the Shabbat comes in earlier, I have way, way less time in my day to be working on my business. I do like to get out and take a walk, and then there's food and stuff that I want to take care of for my family on Fridays. But on Sunday, I would do a brain dump. This is what I do, not what I would do.

But nobody was sharing these beautiful, brilliant ideas, time management idea. It's a planning idea. It's a CEO skill that you develop of putting down on paper every Sunday all the things that need to get done in your business this week. Putting down on that piece of paper all the things that need to get done in your house this week.

For example, as we are only a short time away from Rosh Hashanah, part of my days are now going to go to planning my meals and shopping and cooking. And that's going to take up more time in my week than it might have in the middle of a month where I was not planning for Jewish holidays.

I want to make sure that I get that all down on paper, and then I open up my Google calendar. By the way, this was a huge change in my business. I was very resistant to having a digital calendar. I really, really loved, back in the day, I really loved my paper and pen calendar. I took it with me everywhere. And I was probably one of the last people coming kicking and screaming to having a digital calendar.

And now I love it. I can't imagine what I ever did back in the day without my calendar. Now I've got my calendar on my computer, I've got it on my phone, and it tells me what to do. So if I need to go shopping, for example, on Tuesday I will put “shopping” in my calendar on Tuesday, and I will have the time that I have it set out.

It's really important, because as a brand-new, or a newer CEO, in your business, you show up to work every day and you don't know what to do. I've already told you, one of the things that you can do is figure out your content. You have your content pillar, and you can break it down into all the different topics that you talk about, so that you can start talking about your business to potential clients, to potential referral partners. This gives you a very good idea of what you're doing.

But if you're newer in business and you don't have a fully booked calendar, you kind of show up at work in front of your computer, your desktop, your laptop, and you sit there wondering, what should I do today? That's why you want to put in your schedule exactly what you would do.

And then the first two hours of every single day before you have clients, after you have clients, this is really what I like to do, is to work on my business. This is CEO time. And this is sort of moving into point number four.

I would schedule out CEO time in my business every single day. Sometimes it's going to be doing your invoicing and your billing every day. You should be working on your content, making sure that you are writing something for someone and posting it somewhere. This is if you're on social media.

We've talked about already how to market your business without social media, but I show up on social media because it's free. I love it that all these different platforms give me a free voice. It's obviously very noisy out there in social media land, so you have to stand out from the crowd. But most people don't get on with their marketing because they don't know what to say or what to do.

So they sort of sit there every day in business, and they're like, “I don't know, I don't have clients. What should I do?” And they're running around kind of like a headless chicken. So if you do your scheduling on Sunday, you know what times you're taking your kids to the doctor, when you're going to do your shopping, when you're going to do your invoicing and your billing, when you're going to post on social media, when you're going to write your emails, and when you're going to send your emails.

It makes your business so much more structured. You have a clear plan. You don't show up every day, shoot from the hip, just try to wing it, and go out there to do your business. On Sunday, get it all out of your head. Plug it into your Google calendar, or your iCal if that's what you use. That way you know when you show up in the morning.

I really don't like to start working with clients until 11 o'clock. Sometimes, if I'm being really nice, I might work with a client at 10:30. And if I'm being really, really nice, I'll be there at 10 o'clock. There were days that I had 9am appointments, 8:45 appointments, 8:30 appointments.

Back in the day when I was starting my business, I did it all because that's what we do. But it's really important that you set time in your calendar to work on your business. And I really do believe that you need to do this every single day.

So then you might say to me, “But Debbie, I don't have clients. What am I going to do every single day working on my business?” One of the things that you can do in your CEO time… Again, I want to remind you this is point number four, because three and four kind of morphed into each other. So CEO time, on a daily basis, is where I am now.

If you don't have clients now, then what you can do is you can do a practice sales conversation on yourself. Because this will help you when a client actually knocks on your door, or comes in your DMs or sends you an email and says, “Hey, I'd love to have a sales call with you, a consult with you, a discovery call, and see if we can work together.”

And you might freeze up not knowing what to say. If you are one of my one-on-one clients, or you're with me in my Wired for Wealth program, I have a whole process to help you go through your sales conversation called Sacred Sales Conversations. If you don't have my process, or anybody else's process, sit down and really walk yourself through a…  like you're doing role playing with yourself.

If somebody showed up on your Zoom for a sales call, what would you say? What would you do? You have to kind of go back and forth. Maybe it's kind of like Dr. Jekyll, Mr. Hyde, you're being both, you're being both at the same time, but ask them questions.

See how you would respond, and just go through an entire sales call so that you can see what might come up in a potential client's mind. That will really help you. It sort of is visioning ahead of time, and creating those neural pathways in your brain for what happens when you get on a sales call.

Now, if you are already working with clients, and you're having sales conversations, what you can do in your daily CEO time is do your evaluations on what happened in your last sales call. If you had a webinar and it went well, it didn't go well, what you can do in your CEO time is evaluate your webinar.

If you have gone to a networking meeting, and I did that recently, during your CEO time you can actually write down the names of the people that you met. Or maybe you got a list of all the people that were there, and you can follow up with them. You can schedule coffee chats with people. That's working on your business, making connections, getting to know other people, getting other people to know you.

And this is all part of the different avenues that you market your business. You must make time for marketing your business. All of us want to be working with clients all the time. We love our clients. That's why we got into the business in the beginning, because we love what we do and we want to share it and we want to help people.

But if you're not working on your business, your steady flow of clients is going to dry out, and then guess what? You're going to have to go back into the world and market your business. So make sure that you continue marketing your business on the daily. And that's something that I really, really did not know how to do in my business.

We talked about three different things to do. We talked about your marketing content. We talked about your email, and now I've talked about your CEO time and what you should be doing.

And all of those three different aspects of your business should include marketing. You must continue getting your name out there because people just forget about you. Not because there's anything wrong with you, but because we're busy. We lead busy lives. There is a lot of noise out there, a lot of people advertising, and you're just…

People just forget about you because that's the way the world works, and that's the way brains work. Nothing bad about you. So just keep marketing all the time. Always be marketing.

The fifth point, the fifth thing that I would do differently if I were to start my business all over again, I would have invested in high-level mentorship with somebody who could help me, from the beginning, build my business. I've spoken about how in the past I worked with a marketing coach, back in the day, who was above my level.

I probably learned… I thought maybe I didn't learn… but I probably did learn some of these things that I mentioned today; the content pillars and the emails. I did, at that time, when I was working with this marketing coach, I wrote an eBook, and then after that, I wrote another eBook in order to get people onto my email list.

So I guess I must have known something about an email list by the time I worked with this marketing coach. But not when I was working with my financial planning mentors. I had mentors who were good financial planners, but they were not business builders. And there is a difference, and it showed up in their business.

I told you I worked with like two different mentors, A and B. A and B split up at one point, and I went with B. B was a better business builder than A. I'm just going to leave it at that. But someone who understands how to build a business, rather than someone who's focusing on one aspect of building a business.

And here's where you really need to be careful, because if you hang out on the interwebs like I do, or if you hang out on social media, every single business owner who is selling you something to help you build your business will tell you why you need their specific thing.

You need a website in order to have a business. In the beginning of your business, you do not need a website, FYI. You can go out there on social media or you can just meet people in real life. Once upon a time, people didn't have websites. I know people look you up on websites, but you can grow your business to $50,000, $60,000, $100,000 without a website. At some point, you, for sure, 100% will need a website. But in the beginning, you don't.

Anybody who's developing and designing websites will tell you why you 100% do. People will tell you, and this is what happened to me, why marketing is the most important thing that you need to do. But guess what? If you’re marketing, you get a lot of people coming to you. But if you don't know how to sell them and close the sale, then the marketing is a very good tool, but you’ll need the next step. Which is why my Wired for Wealth process includes both marketing and selling.

In fact, I think that sales are more important than marketing, because we can go out there and we can talk with people and we can run workshops and we're just sort of throwing spaghetti at the wall with our marketing in the beginning, and people reach out to you.

I had this so often; people reached out to me. I had follow-up discovery calls after I did my live workshops, but I had no idea how to close a sale and to get people to work with me. I gave away so much free time, so many free 15- and 20-minute consults helping people, but I couldn't help my potential clients see the long-term vision around why it would be important for us to work together, and why they should actually hire me as a financial planner.

So I just gave them some quick advice and off they went. And they didn't really get their problems solved. People only get their problems solved when they say yes to working with you and pay you money. So they just had a little problem, a little scratch, we put some healing ointment on the scratch, and away they went.

But there was probably a deeper problem with their financial planning, and it would've made sense for me to know how to close the sales call so that I could help people in a better, deeper way. And that's why one of the first tools that I created for my clients… first my one-on-one clients, and then my group coaching clients… was my Sacred Sales Conversation guidebook.

Because it's so important to get all of those potential clients saying yes. Because that's really how transformation is created. We can have a lot of transformation or change or shifts happening by free content, and all that free content is available on the internet anyway, but true, deeper transformation happens in a paid container.

So what I would have done all over again is paid for higher-level mentorship with someone who understood the process of building a business. Because nowadays people will tell you you need the social media, as I said, and you know how to run a webinar.

In fact, I almost signed up for a course once. I was so sold on this. I was already doing workshops and webinars. And somebody's marketing was so good I almost signed up for a course for someone to tell me how to create clients or grow my business via webinars. As if that's the only thing that I needed.

I almost made that mistake, but at the last minute I'm so grateful to my younger self that she didn't do it. Ultimately, when I started working with business coaches who were helping me understand the process of building a business, something that I was already doing but I wasn't doing it very well, a lot of haphazardness going on.

That is when my business started to take off. Plus what we've talked about before, a shift in my mindset and healing some of my deeper blocks around money that were stopping me from showing up and asking for money. So those are the five things that I would do differently.

Number one is I would have an email list. I would write down and create my content pillars and all of the different sub-pillars under each of my pillars so I would know what to write about to my potential clients every single week in my emails.

Number three was having a Sunday schedule brain dump of my personal and business, and all the things that I needed to do that week. Plug it into my calendar so that I had guidance when I would show up to my work every day.

Number four is having CEO time in my calendar every single day, and showing up to my business every single day to work on my business. Working on your business is not answering emails. Working on your business is not going around Google and looking for more free content on how to grow your business.

Working on your business is very specific. Writing your marketing content, sending emails, connecting with potential collaboration partners, scheduling a workshop or a webinar, that's marketing. That's getting your name out there.

And the last thing that I would do is I would hire a mentor. I would, and I think that what I would do is I would hire a mentor who did both one-on-one coaching and group coaching. I really like the hybrid model because I would want some one-on-one time just for my business, and I think it's also very useful because we sit at home in front of our computers, we feel very isolated, and when you have a small group that are your people, I think that helps you see where they are, where you are.

We're all doing the same stuff at different levels. We all have the same mindset blocks at different levels of our business, but basically, we're just spiraling, and we're continuing to grow up, up, up, and we just kind of go around and we face the same issues all the time wherever we are in business. The same mindset blocks, the same money blocks, the same marketing hiccups, the same sales conversations, the same CEO issues that we're facing.

Sometimes it's the systems and processes and the tools we have in our business, but we're all doing the same stuff and it's just very, very helpful to know that you're not alone, and it's not just you who's having these issues.

So I want to leave you with one last invitation. We started with email at the beginning, and I'm now inviting you, if you are not yet on my email, I am inviting you to get onto my email list, DebbieSassen.com/newsletter. Because in the coming month or two, I'm coming out with three brand-new offers, secret offers.

I'm not going to tell you about them now, but they’re going to be very useful for you at different stages of your business. Some of them are going to be good for everybody. Some of them are going to be good for just coaches, brand-new coaches who are getting started growing their businesses.

And I think that it will be very useful for you to be on my newsletter so that you are going to get that early-bird notice. You will be one of the first people to know, and then I can help you. These are going to be smaller offers than my group offer, Wired for Wealth, so I can help you in smaller ways, but very impactful ways, to grow your business.

So that is it for today, my friends, and I look forward to seeing you on the Jewish Entrepreneur Podcast next week. Bye-bye, for now.

Thanks for listening to The Jewish Entrepreneur Podcast. If you want to stop underselling and underearning and close more sales, you need to clear the limiting money beliefs that are sabotaging your business growth.

Head on over to DebbieSassen.com/mindset and download my free Money Mindset Workbook. Uncover and dissolve money blocks, like hundreds of other entrepreneurs who are now building six-, multi-six-, and seven-figure businesses and creating true financial freedom.