Episode #57:
What I Wish I Knew 20 Years Ago

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No matter how long you have been in business, there is always room to improve and upgrade. In this insightful episode, Caterina shares 11 insights she wishes she would have known 20 years ago. Whether you are a new entrepreneur or a seasoned businesswoman, you will find value in this list. Take a moment to listen and think about areas you can improve on to help you bliss and thrive more in your business and in your life.

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Expand Your Fempire Podcast #57 Transcript


What I Wish I Knew 20 Years Ago


Welcome to Expand your Fempire with Caterina Rando, the podcast for women in business on a mission. Sharing ideas to support you to grow and thrive. Now here’s your host, Caterina Rando.

[00:00:24] This is Caterina Rando, and I am blissing to be with you today for another episode of the Expand Your Fempire podcast. Today, we are talking about a very exciting topic. I’ve been in business for many years. I wish I knew what I know now when I started way back when.

[00:00:51] Today, I’m going to do my best to share with you my insights, things I do, things my clients are embracing, that I wish, wish, wish I was doing 20 plus years ago. Hopefully the purpose of our time together today is for me to shave some years off your learning curve. I am confident I can do that in our brief time together today.

[00:01:20] Here’s the thing. Coaching, taking seminars, being in a group program, we do all these things to accelerate our success. What I want you to know is that there are things you don’t know, that you don’t know, that would absolutely catapult your business. And that’s what we’re going to focus on today.

[00:01:42] I am going to take what I wish I knew 20 years ago, I’m going to take things we’re doing that we weren’t doing years ago, that are now supporting us to accelerate our business, have more ease, and most importantly, bliss more in your business. Because your business is supposed to be your bliss.

#1 Your business is supposed to be your bliss.


[00:02:04] And by the way, let’s start with that. That’s number one. Your business is supposed to be your bliss. If you are not blissing in your business, I want you to look at how you can bliss more in your business? Or what is going on in your business that makes you not bliss?

[00:02:25] Usually it is the things that have nothing to do with the business that you chose to be in, that are taking away your bliss.

[00:02:36] What do I mean by that? If you are a graphic designer, you love doing the graphic design, it’s the bookkeeping that gets to you. Well, that’s why you don’t do it. That’s why you have a bookkeeper.

[00:02:49] One of the things I’m not very in love with in my business is scheduling appointments. I like to talk to people. I don’t like to schedule appointments. Because it takes a lot of time and back and forth and I know there’s automation solutions, but I find those to be not as effective as personally reaching out to someone and inviting them to talk to me. And therefore, now I have help with my appointment setting. Not a hundred percent help, a lot of help.

[00:03:17] I was thinking only this morning about the fact that there are several conferences that I’d like to apply to speak for. And I’ve had it on my list to apply to these conferences. I’m not getting to it. What does that do? That creates frustration. Frustration creates stress, which makes me not bliss in my business. I’m deciding, I’m telling you right now, you can ask me, I’m getting support to fill out these applications for speaking.

[00:03:50] Because here’s the thing. It’s not that you can’t do it. It’s not that it’s even going to take you that much time. If you’re not getting to something that you feel is important, then you want to get some support for that. And that will add more ease to your business, which will have you bliss more in your business.

[00:04:11] For example, you may know that I used to publish a magazine. Well, I realized at some point that I’ve written books, I like to write. As a regular thing on an ongoing basis, every month, every month producing a publication- that’s not my bliss. I would much rather be speaking. Therefore we closed the magazine because I really don’t want to do something that doesn’t make me bliss.

[00:04:41] We used to do book publishing before that. We published a lot of books and it was very lucrative, but it wasn’t my bliss.

[00:04:50] Make sure you’re doing what is your bliss. Today I am blissing in business. That is largely due from having attention on what does not fill my soul and what does. I’m going to ask you right now is what you’re doing filling your soul? Lifting you up? You’re blissing to go to work every day? If not, evaluate that.

[00:05:18] Because look how much time you spend at work, especially when you have your own business. We want to make sure you’re blissing during that time. Now you might love your work. You might be blissing in your business. However, there are things that you’re doing that bring you down. Put your attention on that.

[00:05:38] Maybe you need some support. Maybe you need to not do it. Maybe you need to make some decisions that will move you towards getting out of this in your life. That will absolutely support you.

[00:05:51] Number two, master your sales. Don’t only take a sales class. Don’t only sell. Seek to master selling as early as possible as you can in your business.

[00:06:12] How do you master something? Remember our Malcolm Gladwell friend in his book, Outliers, says 10,000 hours it takes to get to mastery.

[00:06:23] What I like to say, because 10,000 hours is a very big number, I like to say “every hour is one hour closer to mastery.” Every hour you spend focusing on your sales will get you to mastery sooner.

[00:06:41] Because it doesn’t matter how good your systems and your operations and your programs and your products and your offerings. None of it matters unless you can gain clients.

[00:06:54] Here’s the thing marketing and sales are not the same thing. Marketing is letting everybody know how amazing your products and services are. Sales is when you invite someone to be your client.

[00:07:09] Depending on your business, you may have to talk to people to get sales. Even if you have a great website and a great online funnel, for most things that are not small, people are going to want to talk to you. Again, depending on your business model. The truth is though that if you can’t talk to people and invite them to be your client, you absolutely cannot gain clients with ease.

[00:07:36] I went to fashion school for a year. I loved fashion school. I didn’t pursue a career in fashion because retail was super boring. And I didn’t know about being an image consultant. That’s a whole nother topic I think I’ve talked about before.

[00:07:54] Here’s the thing, I loved the class on textiles learning the difference between seersucker and satin and Terry cloth. And I loved the class on the history of fashion, which was all about all the costuming and trends over the different periods in history. That was super fun.

[00:08:17] The other class I loved was a class on sales. And I got an A in sales. Do you think that was the last time I ever took sales? No, I’ve taken it tons of times.

[00:08:31] I teach sales and I still take sales classes because we don’t just want to learn something, we want to master it. And remember that sales is one of the five areas that you want to master in your business. Reminder of what those are: speaking, selling, serving, strategy, and self care. You have five things you have to master in your business.

[00:08:57] I wish I knew that 20 years ago. I guess that’s a whole nother one here. Number three, focus on those five things that you seek to master and master them. Speaking, selling, serving your clients, strategy and self- care. The more you can not do all those things that you don’t seek to master, the more your business will grow and thrive, and you will absolutely bliss in your business.

[00:09:30] I’ve been in business 28 years at this recording. The last couple of years, I’ve taught a lot of sales classes. And as a result, I’ve gotten a ton better at sales. Every time you get to mastery, there’s another level of mastery to accomplish.

[00:09:50] Master sales. Pursue mastering sales, pursue mastering your five pillars of speaking, selling, serving your clients, strategy and self care and get support for the rest.

[00:10:06] By the way, we have a whole episode on these five pillars. These are the five pillars of building your Fempire.

[00:10:16] Next, number four, a bigger team and a better team.

[00:10:22] When I got my first virtual assistant, my business tripled because she was helping me do all the things that were not the highest and best use of my time. Tripled. And it wasn’t like I was doing 50K at the time I went from 100K to 300K annual when I got my first assistant.

[00:10:46] Then I started to put attention on how to run a team, how to build a team, having agreements with people on my team, having everything written out. That went well.

[00:10:59] Then somewhere along the line I started to have team members that… I really needed help, so okay, let’s get a mama to help me, rather than being very discerning about who has the privilege of being on my team. Because it’s my intention to treat everyone on my team very well. And we have things in place to do that.

[00:11:27] I want you to have the team of your dreams. Right now I have the best team I have ever had. Do you know what that means? That means everybody on my team is doing a great job. I am blissing to have the support of the amazing people that I currently have on my team. That’s what I want for you.

[00:11:49] Create a criteria for who has the privilege of being on your team. Put in writing what you’re going to do to treat them good. I pay my team for their birthday. That’s one fun thing we do. They get to charge me for their birthday and they also get the day off.

[00:12:08] I am totally flexible when their life needs to take them away from working. That’s why you have a team. Someone else can support you when someone needs to be off. There’s much more to share about this. We’ve also done an episode on this hot topic.

[00:12:28] Team, team, and more team that meet your criteria. Your goal is to have an amazing team that you feel totally supported by that loves working with you. Having a great team will absolutely bring you more bliss in your business.

[00:12:50] Number five, I’m laughing at this one. You will never get through your to-do list. Forget about it.

[00:12:58] When you have your own business, there is always plenty to do. The thing is if the list gets too short, you have a lifetime supply of brilliant ideas to implement. You’ve probably heard me say that as entrepreneurs, we suffer many of us from brilliant ideas syndrome. This is a malady that has the ability to give us more ideas than we could ever possibly implement even with our amazing team.

[00:13:37] Very important that you don’t have a desire to ever complete your to-do list. Because that will have you working way too much. I want to invite you to put together your success schedule. Your success schedule is when you are working.

[00:13:59] As the years progress, you may want to work less and less because your business is growing and it can give you more time freedom. Decide every year what is your success schedule going to be for this year? Could be three days, four days, five days, might be six days in the beginning.

[00:14:24] Stick to your success schedule though. If you have a beautiful family that you want to be with at five o’clock or pick up your kids at three o’clock or four o’clock, whatever works for you. If you have your own business, then the reason you have your own business, or one of the reasons in addition to blissing, is time freedom.

[00:14:47] Time freedom doesn’t mean we relax all the time. What it means is we get to be free to determine our own schedule. And this is based on the other priorities in your life. If you want to get up early and work out, if you want to take the afternoons off for circuit class or yoga class or belly dance class. I often end at four to do a class. Whatever works for you.

[00:15:15] You may have certain nights that you work. Certain days that you don’t work. If you have older parents that you want to go be with. Whatever it is, create your ideal success schedule. Recognize you’re never going to get through your to-do list and take that pressure off yourself.

[00:15:38] My friend, I hope -that was me blowing you a kiss- I hope you’re hearing me because this is a key to your best entrepreneurial life.

[00:15:49] Number six, take more time off. Now, I know this is relative. Everyone’s business and lifestyle is. I will be very transparent here and say that I have worked way too many weekend days when I was married. I worked way too many weekend days, instead of finding a way to be with my love and be out and about, even if it was taking a walk in the park. And I think perhaps in the earlier years it was more the fear of not getting it all done or the fear of not having things be good enough.

[00:16:34] Remember perfection is not required. Done is better than perfect. One of the things I do my best to do now is to allot a certain amount of time to activities. For example, if I want to write up a description for a workshop, I tell myself I’m going to take 10 minutes for that. Now it might take 20, but I don’t let it take the whole afternoon.

[00:17:02] Or if I’m doing my planning for the next week, I could plan next week for the next five hours. Or I could tell myself we’re going to do this for 15 minutes.

[00:17:14] Very important that you begin to do your best to decide in advance how much time you’re going to allot to something and do your best to stick in that time frame.

[00:17:27] It doesn’t always work. However, getting yourself in the habit of this will increase your focus on these activities. Less distractions will make sure that you’ll get through them much more effectively.

[00:17:44] If you would like more time off in your life, meaning time away from your business, I want you to ask yourself, what would it take to create more time off? This year I made a decision to do a, I call it a staycation in July, which was no speaking, no teaching, turning over some of my other responsibilities to my clients, like running the sales blitzes and running the Clubhouse room we do Friday nights at five.

[00:18:20] I took some time for a vacation. When I wasn’t on vacation, I was on staycation, which really was me working on projects, having lunch with girlfriends, not going away. At the same time, not having any business responsibilities, still having the freedom to work on my next book or work on any creative aspects of the business.

[00:18:48] I’m so excited that I did this in July, because by the way, next super tip alert, at least in my business, July tends to be a dip month with revenue and a dip month in attendance for a lot of the speaking that I’ve done. I will even tell you, I broke my rule about this. The last week of July, I went to talk at an organization I thought was a big organization and almost nobody showed up for the talk.

[00:19:21] Very, very important that you begin to pay attention to the time trends in your business. There may be a month or two or three during the year when your business naturally dips, meaning there’s not a lot going on. Therefore, you may want to take a staycation or a vacation at that time of year when your business and industry seems to have a dip.

[00:19:47] Number six, take more time off.

[00:19:50] Number seven, look at when during the year you could do a staycation or a reduction in responsibilities.

[00:20:02] Caterina Rando: When I say staycation, it could be that you get away a little bit in your area. Don’t jump on the plane. It could be you take an afternoon off every now and then. It could be that you have time at home to catch up on your rest, catch up on your reading, enjoy some bingeing of Netflix, whatever rejuvenates you.

[00:20:31] There’s another purpose though, here, and notice it’s not just a staycation it’s reduction in responsibilities. What I’m looking for here is some creative time for you to work on whatever you’re working on. Because creativity requires time and space.

[00:20:53] What does that mean? You don’t have 10 appointments and you’re trying to do strategy in a half an hour between appointments. You don’t have any place to have to be, or you don’t have any important project that is on your desk that is distracting you.

[00:21:11] In July, I did my staycation where I did get away for a few days. I also, though, decided I wasn’t going to teach or speak or do sales appointments or coaching appointments or anything like that in July. Now I got a ton of stuff done and I got a ton of strategy because I took time away from the regular day- to- day activities of my business.

[00:21:43] Let me be honest, too. This is the first year that I have ever done this, where I’ve taken a month out of the year to get reinvigorated, rejuvenated, refocused, looking at different things. And I honestly don’t know where the month went. I had no shortage of things to do.

[00:22:05] It was so beneficial for myself and my business that this is now going to be standard operating procedure. That every summer, could be July could be more in August, depending on what’s going on I am going to take some time for this staycation. It doesn’t mean there’s no work, but it means reduction in all of the regular responsibilities.

[00:22:31] I want you to look at whether or not this is something that would serve you. Now, you might disregard my idea because you might say “Caterina if I don’t see my clients, if I don’t run my groups, I don’t get paid.”

[00:22:44] Well, that might be more of a question of cash flow versus workflow.

[00:22:53] What do I mean by that? Several clients, many, many of my clients paid me in July for coaching, even though they knew they weren’t getting any coaching in July. What we did though is we took their payments and we said, “Well, you might be having 11 months of service, but we’re going to divide that over 12 months.”

[00:23:15] Therefore money was still coming in in July. Now this is how I do my cashflow. I do want you to look at this though, because it doesn’t mean that you can’t get well paid during your dip month or your staycation month. You can still get well paid if you have put attention on this and then advance.

[00:23:38] Now, I said a month, it could also be a week, my friends, you start where you are. It could be a few days in the beginning, then it can go to a week. Then it could go to two weeks, whatever you decide.

[00:23:52] This is going to be a very key time for you.

[00:23:57] Therefore you could be more creative, get recharged, get re-invigorated, plan for the fall. Again, in my business, I have noticed there’s usually a dip in July. When is it for you?

[00:24:12] Time is really the asset that we want to put a lot of attention on in our business. Doing revenue producing activities, doing what’s the highest and best use of our time, not doing what we don’t seek to master. Always be looking at this- how can I use my time better?

[00:24:35] Number eight, 20 minute conversations. One of the things I only started to do in the last year is when I put appointments on my calendar to talk to people… check in with a client, potential client conversation, somebody that wants to talk to me about a speech or about something, any conversations. I only put a 20 minute appointment on my calendar. I used to do 30. Now I’m doing 20.

[00:25:11] I’m going to re-evaluate and see if I can get it down to 15. Because it doesn’t usually take whatever it is- it doesn’t usually take more than 20 minutes. Now that’s not to say that sometimes calls don’t need more time. The thing is though that the email reminder to the other person says 20 minutes. That way, they’re thinking about a 20 minute conversation, rather than thinking about a 30 minute conversation.

[00:25:41] And this has added a lot more ease in my day because I have a 15 or 20 minute conversation, then I have an extra 10 minutes to do any notes from that call, to send anything I said I was going to send, to make sure I’m drinking plenty of water, to read a quick email or do a quick task.

[00:26:03] And I wish I was doing this 20 years ago. I’m not sure why I wasn’t. Now I’m down to the 20 minute convo and I am blissing much more in my business. That’s number eight- 20 minute convos conversations.

[00:26:22] Number nine: community is key to an amazing business and an amazing life. The more you can cultivate community through your business, having your clients get to know each other, get to support each other, share resources, they’re getting so much more value than only knowing you because they’re your client. As a result, they’re going to get so much more value that they’re going to stick with you forever and ever. That’s what I want for you.

[00:26:58] Here’s the other thing, though. You want to see the impact of your work. You want to see the amazing results that you’re getting and you want to talk to your clients and customers, and you want to get to know them personally.

[00:27:14] This idea of not having personal relationships with our clients is ridiculous. Get to know these beautiful people, because that will uplift your life. And look for ways to facilitate community building and connection so that what you will see is your client’s blessing because they are your client and all the other gifts that you have given them.

[00:27:45] I’m recording this right now after having done our Friday evening wrap up on Clubhouse. We do a weekly room, wisdom week wrap up and sharing wins in our Thriving Women in Biz Club on Clubhouse.

[00:28:06] Every time I even think about this room, I am so happy. Tonight, Freya in our community was talking about her confidence and visibility group that just finished, how much fun it was, how much the ladies loved it, how much more confident they’re feeling. Andrea shared about her workshop on having impact and how much value the ladies are getting.

[00:28:32] Hearing everyone’s wins lifts me up, lifts them up. We’re all connected. We’re all getting to know each other more. We’re all leaving the Clubhouse room more uplifted. It’s a great way for us to stay connected and continue to be in relationship every week.

[00:28:53] There of course are many other things we do in community. We have monthly networking, something we’ve only been doing for a couple of years. I wish we’d been doing it for 20 years. Where we all get together once a month in a zoom room. There’s a theme. There’s a focus. We have breakout sessions. We share what’s going on and coming up. Again, wish I was doing it 20 years ago.

[00:29:18] We do quarterly planning. We do masterclasses. We’ve just added this year sales blitzes, where we get on Zoom three times a month and we do sales reach outs and sales conversations asking people to our workshops. We do it all together. We share what we’re going to do. We turn off the Zoom sound and video and we go do it. And then we report our results back at the end.

[00:29:46] We’ve only been doing this for one year. I wish we were doing it 20 years ago. These are some of the ways I’m sharing with you that I cultivate community consistently in my business, in my client community. And I invite you to look at what you can do to get your clients together and have them do whatever they do in community.

[00:30:12] And the virtual world is not as ideal as inviting people to your house or your living room, or maybe it is because then you don’t have to clean it up. The truth is though, that this allows more people to show up and be with you and be in community.

[00:30:29] And I’m hoping that after right now, you’re going to look at how you can do that even more. Tracie Root, she has the Gather Community, which I’m a part of. I went to trivia night virtually with her and other ladies in her community. Super fun. It doesn’t always have to be business. It can be social as well.

[00:30:52] Community is key to a great business and a great life.

[00:30:57] Number 10, retreats are required. Did you hear that? Retreats are required. Now that could be a one day getaway. A two day getaway. Could be a 10- day getaway. Make sure you’re getting away in a retreat setting, where you’re focused on self- care or you’re focused on recharge, rejuvenate, reconnecting with yourself and your mission, your goals, your dreams, your vision.

[00:31:33] And I suggest also connecting with other like-minded like-hearted women on a mission, just like you. This can be a formal retreat, like the ones that we do. It can be an informal retreat, getting away with a couple of other entrepreneurial girlfriends. Retreats, though, are required.

[00:31:58] Again, something that I was not doing from the beginning in my business, that I’m hoping that you’re embracing right away. I would say one big, bold, hardy retreat a year, for sure. Plus, at least two smaller retreats or two bigger retreats a year.

[00:32:24] By the way, if you’re like me and your host retreats, those retreats don’t count for the retreats you need personally. I host my retreats and then I go on retreats with my coach and with other women entrepreneurs. I went to a retreat a couple years ago my friend was hosting in Italy. It was awesome and amazing and nothing like any retreat that I would ever do. Very different and still met that criteria of relaxing, rejuvenating, getting recharged, refreshed, renewed perspective. That’s what I want for you. Retreats, my friend, are required.

[00:33:11] Let me share with you also, my mom is 89. She is a woman with a lot of vitality. She said years ago, “when I go away, when I leave my house, I want to stay someplace that is nicer than where I live.”

[00:33:34] Now I am not a rustic gal. I have not tried glamping. I am open to trying glamping. I am not asleep on the ground with the dirt and the leaves kind of gal. I do want to encourage you use these retreats as an opportunity to bring more VIP luxury pampering into your life because you deserve it.

[00:34:04] Perhaps it is irrelevant, whether or not you deserve it. Deserving has nothing to do with it. I encourage you to treat yourself VIP. That is part of self-love. I said in a recent podcast about the five love languages that we want to use the five love languages to love ourself. And treating ourself good is an act of service. As a woman, please do not see it as spoiling yourself. I do not like that word. Treat yourself good because you love yourself.

[00:34:46] Number 11, this is the most important one. This is something I super wish I knew 20 years ago. It is not only okay, it is awesome to wear your heart all over your business. When I was coming up as an entrepreneur, I was very active in my chamber of commerce here in San Francisco. I am a big fan. They’re all very different. Check your local area for yours.

[00:35:26] In my town, the chamber of commerce has a lot of small business members and they also have big business members. All of the companies that are headquartered here in San Francisco. At the time it was bank of America and Chevron and now there’s a lot of tech companies as well.

[00:35:52] And I was on the board of directors for the San Francisco chamber for six years. I was the youngest for the most part person on the board. I probably had the least experience of anybody on the board and I would watch how all the executives spoke and ran meetings and attended meetings and networked. Many of them were the vice presidents of these companies. And I was looking to see how you do business.

[00:36:30] I would say 90% of them were white men, maybe a couple more women than that. And they were traditional business people. It took me too long to realize that I don’t have to be like that. I can 100% be myself. I can send sparkly New Year’s cards. I don’t have to wear a double- breasted or a buttoned up blazer.

[00:37:04] I can wear big earrings. I can hug people. I can ask about their personal lives and express genuine interest and concern if needed or appropriate in who they are as an individual. I can be real. I can be friends with people. It doesn’t have to be all business.

[00:37:32] Not only in the last few years have I worn my heart all over my business, I’m always looking for how I can amplify my love, my caring, my heartfelt bliss at other people’s success all over my business.

[00:37:54] Look at these 11 things we’ve talked about and ask yourself, “Hmm, where can I make an upgrade based on what we’ve discussed?” And this may be the place, because you’ve heard me say 50 times, your business is supposed to be your bliss.

[00:38:16] What if your business was all about love?

[00:38:19] I know that my business is about selling and speaking and scaling, building community, doing retreats. These are the things that people pay me to focus on with them. And I’m going to color and infuse until it’s soaking, all of that with love. Now, that is my intention, cento per cento 100% of the time. Doesn’t always turn out that way. That is absolutely my intention.

[00:38:55] Let’s leave it there for today. I’m sending you some love. Call on me anytime. For any reason, I want you to remember that you have massive value to bring. That there is a lifetime supply of people to serve.

[00:39:14] I invite you to look for how you can bliss more in your business. Look for how you can be more productive with your time. Look for those ways that you can make it standard operating procedure to embrace some of the things we’ve discussed today. Your calendaring things way in advance like retreats, going to a 20-minute phone call, paying attention and mastering your five pillars. All of these things will support you to be more productive, more profitable, and more blissful in your business.

[00:40:01] I’m Caterina Rando, and I cannot wait to be with you again here and watch you expand your Fempire.

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