#132: Why You Should Do More of What Scares You

Leilani Haywood, a freelance writer and copywriter, talks about overcoming fear to grow her business. She shares strategies for client acquisition and the shift from working as an employee to running her own freelance operation.
Welcome to the High Income Business Writing Podcast, helping you propel your writing business to a whole new level. And now, here's your host, Ed Gandia. Hey there. Thank you for joining me for episode 132 of the High Income Business Writing Podcast. My name is Ed Gandia and this is the podcast for business writers and copywriters who want to take their writing businesses to the six figure level or the part time equivalent. Just a quick reminder that you can find details, show notes to this episode by going to b2b launcher.com Episode 132 I really believe that all of us are born with a great sense of wonder, courage and boldness as toddlers. If you have kids, if you have grandkids, if you know people who have little kids, you can see it. You can see that they have tremendous curiosity and they're not afraid to explore and to express their creative spirit. But somewhere along the way, fear begins to rule our lives. Fear of looking stupid, fear of rejection, fear of criticism, fear of failing. And we begin to lose our confidence. We stop taking chances. We start playing small. At times, we might even start to feel like a fraud. Fortunately, there are many things we can do to turn this tide into regain our confidence. And one of them is to get into the habit of doing more of what scares us. And in this episode, you're going to hear from writer and copywriter Leilani Haywood, and she is going to explain how she deliberately does things that scare her in order to grow personally and professionally. And she's going to talk about how this practice has enabled her to launch and grow, which become a thriving freelance business. So I think you're going to enjoy this conversation. Whether you struggle with this on a frequent basis or whether fear just comes kind of rears its ugly head as it does for so many of us, I think you're going to walk away with some, not just encouragement, but with some actionable advice on what you can do to counter the effects that fear has in your business. Without further ado, please enjoy my conversation with Leilani Haywood. Leilani, good to have you on the show. Welcome.
Thank you, Ed, for having me.
It's a pleasure to have you on and I'm excited to talk to you about this topic and to hear more about your story. But as usual, I always like to ask my guests to give us a little bit of background so we have some context for discussion. So tell us about yourself, the work you do, the types of clients you work with, and so on.
Sure. Well, I own Heywood Marketing and Communications and it's a boutique editorial social media copywriting company. And right now I have several nonprofits where I do all of their copywriting. A financial services company, a publishing company where I manage their online magazine, and a couple body shops that need social media content and a local restaurant. And so I have got a variety of companies where I do different types of copywriting. And then I also will take on some other projects to fill in when times are slow and that sort of thing.
So good variety there?
Yeah, yeah, it's a pretty good variety.
Now, I'm curious, how long have you been freelancing? How long have you been doing this kind of work?
Well, I actually started, like 100 years ago when I was in college. I was taking a magazine writing class in my journalism school. And so my magazine professor challenged us to. To write some query letters to magazines because she said that she had one of her students land a Rolling Stone assignment just like completely randomly, out of the blue. And so I went on spring break. I took the writer's market, which was like this huge book, this directory of all these publications, took it by the pool and wrote some query letters. I wrote about 10 query letters, and I landed two assignments out of that batch. And so I started. I guess I kind of started on the side years ago. And through all the different jobs that I had, I always had, you know, I was always freelancing for the local business, newspaper or magazines or businesses. My friends that own businesses that needed a brochure, you know, they needed a copy written for a brochure or a press release. So kind of always did that on the side for about over 20 years.
Wow. Okay. So you had a day job and you just did this as a side thing for friends, people who just kind of came to you who needed help.
Yes, yes. And so that was. Yeah, making that leap was just. It was scary. It was kind of like jumping off a mountain cliff.
And so I'm curious, in terms of what. What work did you do in your day job? So what kind of work did you do all those years you were freelancing on the side?
I. Well, I started out as a newspaper, newspaper reporter and then covering politics, and I shifted into public relations and then into script writing, where I wrote scripts for video productions. And then I went and worked for an editorial company, just like basically looking for potential authors, like an acquisitions editor type position. And then, yeah, I did. I worked at a university for their information technology division. And so did. Yeah, just kind of did different things, but it all had the writing in common. But you know, we always have the addition of PR marketing, and I even did a stint at an insurance company where I was their copywriter, which was super boring. You know, it's like every position that I took in these different companies would open a door that I totally did not expect in freelance writing.
That's very cool because he had some. So you got some very relevant experience that you could then leverage either on the side or later on.
Right, right. Like, I worked as an editor for a telecommunications. It was a telecommunications online magazine. And I had no idea when I started working on writing articles for like telecommunications, wireless, you know, the computing technology world, how actually that is. You're positioning yourselves for some very lucrative assignments. I mean, I got, I remember when I got my first magazine assignment for a telecom magazine. That was a dollar a word. Like, really? Wow. Somebody should have told me this early on.
Well, let's talk about your transition. So why did you decide to then go out on your own? I mean, it sounds like you enjoyed the work, but that is a big leap, as you mentioned earlier. So what went on or what motivated you to make that leap?
It was a combination of circumstances where I have a daughter with special needs who, you know, I need to have a more flexible schedule for her. And then I was also around that time where, you know, she was, she was needing me more. I was working for an ad agency as the, I was the only copywriter for this ad agency. He put me on a team to create a product called Internet Content Management. And so he put me through a boot camp to learn everything about social media, which, you know, when Facebook was just getting started. And so I went through eight weeks of learning every aspect of social media and blogging and putting together a product for our clients. And so right around that point in time, I just got this aha idea. Like, you know what, I wonder if there's some small to medium sized businesses that would, you know, that would want these services at a more affordable price. And so that's when I started like brainstorming, talking to some of my friends who were very successful entrepreneurs, bouncing the idea off of them and making the leap. And so it was a combination of opportunity, which now in retrospect, I thanked the ad agency that he provided the training. I got the idea while I was going through his training and made the leap.
That's good. The timing was just right too in terms of social media, because I'm assuming this is like late 2000s, right? 2008, 2009, it sounds like.
Yes, yes, yes. Late 2008, 2009. And. And so right around that time, I was offered a contract with a major financial services firm that I've done consulting for, writing digital content for their software products. So it all just happened at the same time where this company called me and said, hey, we want to hire you to help us with copywriting for this project and going to pay you a great rate. You can work at home. And so I took that as my way out to launch my business.
And how did that client come about that they. Was that from somebody you knew or.
Yes, yes, actually, they were my colleague at this telecommunications online magazine. We worked together for the same company. And so, yeah, she just reached out to me out of the blue. She knew what my skill set was, and we had worked together and said, hey, you know, we had this project and. And are you interested? I'm like, get me out of here.
Yes. So. And she knew. She knew that you were on your way out. I'm assuming she actually.
She didn't know that.
Oh, okay.
No, yeah, she didn't know I was on my way out.
Pure luck.
Yes, yes, pure luck.
All right, so this is great because it sounds like this was what carried you over. Most people in your situation, they have to really hustle for some clients. Right. You had kind of an anchor client that kind of financed that transition, it sounds like.
Yes, yes, I like that. I like the way you said that. Yes, I had an anchor client that finance the transition where, you know, I would put in 20 hours, 20, 30 hours on their project, spend 10 hours building my business to where. Where at the end of that contract, my business took over. So it was. It was a great situation.
Yeah. And then once that, Once it was over, then you had no problems in terms of transitioning to. To other clients then and making sure your income was stable.
Yes, yes, because the way, you know, based. It was basically social media that launched writing content for social media, you know, their websites, their blogs, on a recurring basis. So I created this package to where it's like a monthly recurring, you know, like a retainer fee.
Yeah, every month.
So I have like this monthly income that I can count on. And so. And then when the months, you know, and then some clients roll off, and when they roll off, then. Then I look for some other freelance work.
Excellent, excellent. Okay, well, that, that, that makes sense. And you know, those were difficult times too, 2008, 2009. But it sounds like, you know, because social media was picking up in a big way. You were at the right place at the right time. Kind of thing.
Right, right. And it was right around the time when a lot of some companies were. They were outsourcing their marketing or outsourcing their copywriting because of the economy. And so that actually worked for me.
Now, one of the things that you and I were discussing offline and kind of the main topic of our call today is not just how did you transition, but really, more importantly, this idea of doing what scares you. And you've shared with me that doing what scares you has been a key ingredient to your success. And I'm curious to know why. Do you feel this is important? And maybe you can share some examples on how you've used fear as a tool to grow your business.
Yes, yes. Well, one of the things that, you know, I didn't realize how fearful I was until I started walking down this path. And one of the things that I absolutely. That, like, freaks me out. I don't know if anybody else is scared of doing this, but it's, you know, it's talking to strangers and it's getting up in front of people and talking about what you do and what you can offer them. I know some of my friends, they really enjoy that. And. But to me, it's kind of. It's like having a root canal. And so my friend, one of my friends, when I was launching my business, he said, what you need to do, you need to do a presentation to this group of business owners in this area of the city I live in where there's not a lot of people doing social media. And so he said, I know they're looking for speakers. Here's, you know, call this person and book yourself as a speaker and do a presentation to this group that's brand new of business owners. And so I put together a presentation, and I think it was like, why your business should be on Facebook. It was just, like, very simple. 5 reasons why your business should be on Facebook. And at the end of that presentation, I had 10 appointments. And those 10 appointments, half of them became clients. And so that business group launched the social media side of the business, because I did. I basically, I broke out of my own comfort zone to do public, Public speaking and talk to people, you know, that I didn't know. And I found. And I actually ended up doing more presentations in front of this group. And so the fear of talking to people, the fear of, like, asking, you know, when you think that your rate is going to be too high or like, this package, you know, you create this package for them. And I remember just having to stand in front of the mirror and say this certain amount that I wanted, you know, like several times because I was too afraid to ask for that. And then I asked for it, and it's like, okay. And I'm like, oh, this is not a big deal, you know, so.
So now that. That became your new normal at that point, right. It's like, okay, yes, next time I won't be as scared asking it.
Right, right, right. And so, like, talking to strange people, networking, I had to break that fear of, you know, walking into a networking event where I don't know anybody and, you know, just talking to people. That is like a fear that I had to break, of just walking into a room. I mean, it could be so intimidating, which is crazy because, I mean, as a journalist, you have to ask people questions all the time that they don't want to answer. And strangers at that, and strangers, right. Strangers that are in power. And so I would just kind of like, shift into this Persona. I mean, I wasn't being fake, but where I really wanted to know, you know, know about, like, this business owner's background or, you know, I would. My purpose would be to connect with one with a couple people. And it worked. And so now I enjoy networking, and I'm not afraid to ask for what I believe I'm worth and. And to negotiate, you know, ask more details about a particular project, which I found, unfortunately, it seems like me, or maybe it's my clients. You know, a lot of freelancers don't ask for certain details like this. There's this one prospect that I had, and he was surprised that I was asking him all these questions. And I'm like. And I'm thinking, I guess I'm just assuming that every freelancer would want to know these different things about the project. And so I think it's like bringing that marketing background, that PR background to the copy, you know, and so I have found that to be really beneficial. But, yeah, it's been a scary, scary. The scariest thing that I've ever done in my life.
Meaning going out on your own and building and growing a business.
Yes, yes. And adjusting to shifting priorities. You know, like when you lose a client and what are you going to do? And, you know, just the constant flux and the constant change. And one of the things I wanted to say about, like, talking to another fear that I had was talking on the phone. I don't know how many people have that fear, but what I did early on.
Well, first of all, I got a quick question for you. Why was that a fear because in your regular day job, I'm sure you had to do a lot of that.
Yeah. But I think maybe because especially when I was prospecting on the phone.
Oh, okay.
Yeah, yeah, yeah. The fear of prospecting on the phone.
Okay.
And so what I started, what I did early on, is I would keep a spreadsheet of prospects, and I would, you know, set aside one to two hours every week and just make phone calls or try to set up appointments. And so this was something that I've seen in, like, some of my other friends who had freelance businesses, like, you know, building websites. It was a weakness I saw in one of my friends who built websites. He would tell me, you know, that he. This was famine month. And I'm like, well, what are you doing to try to get new clients? And so I have seen that as a weakness, and some of my freelancer friends and I have tried to work on that weakness myself, which is why I started listening to you a year ago, Ed.
Ah, great, great. No, it's. Yes, do. Do what you fear. And, you know, I'm curious when you started. Maybe it was early on, but I. I shouldn't assume. When did you start realizing that, doing these things that were obviously scary? When did you realize that, you know what? This is good for me? It's. I'm creating scar tissue, if you will, that's making me stronger?
You know, I think for me, it was when. After I did that presentation and had 10 appointments, when people, you know, came. They, like, crowded me, wanting my time, and I was like, you know what that was? This is. This was worth me stepping out, spending, you know, 10, 20 hours creating that presentation and doing all the research for that group, you know, because this helped them and it created a business, you know, built my business. And so that was when I was like, I have got to get out of my own way. And one of my first clients, I learned a lot from him. He owns a body shop. He's an amazing marketer, and he really stretched me. I learned a lot from him about networking because he was very involved in the community and creating a relationship with your customers and staying with them, even though. Even the times when they're not a customer, you know, but just building that relationship, that friendship. And so that's when I. When I built that route, when I shifted into, you know what? This is not just a prospect. This is not a client. This is a friend. And so I think that makes a huge difference is when they. Your client turns into a friend.
Oh, yeah.
And. Yeah. And. And so Taking that step out of your comfort zone to find this person, I mean, it's. It's so worth it in the long run because, you know, this person has been, like, invaluable. I mean, very, very invaluable over the last five years.
I'm curious, what things do you do on a regular basis to continue pushing yourself out of your comfort zone? Are there things, little things that you do, or even. They don't have to be little, but things that you. Sounds like you're mindful about this, and I'm curious what you continue to do to make sure that that bar is set pretty high, that you don't get too comfortable.
Well, I mean, I listened to you, to your podcast, and actually, I think your podcast that you did yesterday on Nurturing Leads was, like, amazing. And so I, you know, I mean, just this morning, I resurrected my email newsletter. I mean, I hate to say that I haven't done. Done one in, like, five years. And so after listening to your podcast yesterday, I started going through my. My list of contacts out of LinkedIn. I. I had already exported all of my contacts out of LinkedIn and imported it into my email newsletter software. And so I'm starting to do that again. And then I also will do things to. Like an example is I had a post on Facebook for one of my clients, and so I turned that post into an article to serve that client. And so I did that kind of like, to stretch myself for them and to position them as a content provider in their space. And so I'll try to, you know, I'll think of something like, once a week while I'm listening to you or Ray Edwards or there's another couple other podcasts that I listen to, and we'll just try to implement an idea every week to build my business or to help my client increase their business. I hope that makes sense.
Yeah. Yeah. So it sounds like I'm hearing a combination of things. Some of them are not necessarily things that are scary and outside of your comfort zone. Sometimes it's just being mindful on a weekly or regular basis about working on your business and not necessarily in your business. That's what I gather from that.
Exactly. Exactly. Working on your business and the whole email newsletter thing, to me, is, frankly, scary. I mean, it may not be scary to you, but it's kind of scary to me because I'm like, what if these people think I suck? You know, what if they don't opt in? What if, you know, all the what ifs? Yeah.
So it's A combination. Right. It's a. How can I work? Being mindful about working on your business, at least for a little bit every week. And then some of those things will mean getting out of your comfort zone. I totally get it. It's. You put work out there, and it's that fear of, you know, I'm not good enough, what if, what if this or what if that? And I suspect, based on what you've shared with me, maybe that's one reason why you. You stopped doing it. You know, maybe you got busy, but there were all these other things in the background.
Right? Exactly. I just got inundated by work, and so the whole email newsletter just fell to the wayside, even though I had a pretty high open rate. And. Yeah. And so I'm trying because I do read other email newsletters. I'm thinking after what I listened to on your podcast yesterday, that I need to do this because I, you know, I write email newsletters for my clients that get high open rates. And so why am I not doing this for myself?
Yeah. I should tell you this and for everyone listening, because most freelancers don't know this. They think that they're the only ones who feel this way. Most freelancers feel that their stuff is not good enough and that something's wrong with them because they can do this for their clients, but not for themselves. And I should tell you that it's really, really hard to write your own stuff or about yourself. So there's nothing wrong with you or anybody listening who feels that way. It's actually very normal. Which, by the way, I think there is some value in having a colleague maybe help you do some of your own copy or your own messaging, if you can maybe work out a reciprocal arrangement because it's so difficult. You're too close to your own stuff. It doesn't mean you're a bad marketer.
Okay. Okay, good. That's good to know.
Yeah. Yeah. So the other thing is being a licious. The elephant in the room. Right. Just by being here and volunteering to come on the show. I'm sure that took a little bit of nerve, too, from what you shared with me offline.
Oh, my gosh. It freaked me out.
Well, you're doing great.
Completely freaked me out. Yeah. But I told my friends I have to do this.
Yeah, no, that. And that's good. So, you know, what I'm hearing is many times it's not so much about what will I get out of it as a direct result of doing that scary thing. So, for instance, let's just go back to your talk that you delivered a few years ago. Now that was a classic case of you got some, get great immediate benefit from it in terms of work, but many times the real value is the fact that you've stretched the boundaries of your, your comfort zone and because you stepped outside of it. So now that, that the boundaries are further out there in your growing as a person and as a professional and that can lead to many more things than just getting five clients, as great as that is.
Right, right, right. That's true.
Love it. Love it. I'm curious, in terms of when you look ahead for your business, what do you hope to accomplish over the next, let's say two or three years? Because I can tell you're into self improvement, professional development. Where are you looking to go?
Well, I think I would like to do more training and setting strategy instead of doing the work myself. And so I've stepped out and I've done that the last six months where I've done social media training with some clients and I actually enjoy doing that. And so there is one client that, it's a real estate company where I did an analysis of their social media footprint and gave them a plan on how they could take advantage of their existing relationships, increase their footprint, get more engagement. And so I put together this overall plan and then put together a training for them, for their staff. And so I would like to shift more into doing that, into helping clients put together strategy for their business and then train their people on how to do it instead of me doing it and then focusing, you know, shifting more into writing, doing a lot more editorial, which is what. That's my first love is editorial. And so I, right now I'm editing an ebook for a client. I've got a freelance client where I'm also editing a bio for somebody. And so I enjoy doing those sorts of things and getting out of, you know, maybe doing bigger writing projects and maybe and shifting into where, 10 hours a week. I'm doing just strategy and training, social media training for companies.
That sounds exciting. That sounds like a great mix too.
Yeah.
I'm curious to know about your. That client. Were you doing the strategy and the training? Are you, how did you get, was that an existing client or did they hire you for that piece specifically as their first engagement?
They hired me for that piece and it came from that little business group that I, that I was doing presentations for. The real estate agent was in that group and he recommended me to the owner of the company because he knew that they needed to beef up their social media presence and they needed to bring in someone to give them an idea roadmap on where to go as a company. Then I also spoke at a conference and got a couple clients where I had never done remote training. One of my clients, I did remote training with him on, you know, showing him how to use Instagram and LinkedIn and Facebook and Twitter to YouTube to boost his business. And so, and it was, you know, it was like an hour a week and was not that hard and was pretty lucrative.
It sounds like you have put packages together for this stuff instead of charging by the hour.
Yes, yes, yes, I have always put together packages and, and like, because I have my nonprofit clients, I manage their social media, their website, and I write copy for their email newsletter. And so that's all like, you know, a set rate. And, and so for the freelance writing, like the ebook, I, you know, I, I did, I bidded that on an hourly basis based on the market rate. So. But you know, most, I'd say about 90%. 90% of my business is like retainer. Yeah, based.
Yeah, retainer based on, you know, kind of a productized deliverable and that you package it, this training and assessment and recommendations. It sounds like you came up with a package. And I'm curious, how did you. Obviously you're doing some of this kind of work already, but how did you come up with not just the scope of work but also the pricing? Because that's kind of nerve wracking too.
Yes, yes, that is nerve wracking. I, Well, I got input from the client on what they needed and then basically, I mean, I just googled what people were charging in my area to do, you know, to provide that service. And, and then just. Yeah, I mean, you know, compared my rate to. To XYZ training company and adjusted my rate accordingly because it's just me and I was going on site to their company and that's how I came up with it.
That's great. And now you have a template, right? So you can, like you said, you can do more of this because this is a repeatable thing. I'm sure you'll adjust some items, but you could do this again for others.
Yes, yes, I could. That's a good idea, Ed.
Yeah, Yeah.
I should get you to coach me, man.
Well, you know, you know, what I found is that it's the first time you do it, it takes the longest because you're doing it from scratch. But after that you can kind of templatize and you know, you kind of codify it. And every time you do it again, it becomes easier and more efficient because the template, the framework is there now. You're just dealing with different inputs.
Yeah, that's good.
So it becomes almost essential that you do it again because you'll make more every time you do it.
Right, right.
That's excellent.
And I actually enjoy doing that.
Yeah, well, yeah, that's the key. Right? It's got to be something you like.
Right? It's not scary.
Yeah, excellent. But look, you're getting in front of people. I can tell that this is something that still to this day, requires some courage. But I feel that these things always start with courage. If you can take that first step, then you always create kind of a new normal every time, because that's not new anymore. You've done it. And the second time you do it, it's still a little scary, but it's not. You're not in panic mode, maybe, and moving.
Right, Right.
I love it. I love it. Well, thank you so much for. For sharing these stories with us, sharing what you're doing and. And getting out of your comfort zone to. To come talk to us. I think this has been fantastic.
Well, thanks for having me.
The High Income Business Writing Podcast is a production of B to B business launcher. Learn more at b2b launcher.com.
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