The Biggest Writing Mistakes That Entrepreneurs Make

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

1:58You know what has been absolutely fascinating to me as I have transitioned from the world of pure writer? I came up in media as a magazine editor. All my friends were writers. I thought of myself as a writer. And then I got into the world of entrepreneurship and I started to think of myself as an entrepreneur. And I discovered to my confusion at first that all these entrepreneurs I was meeting, they all want to be writers. It seems so weird to me. Because has anybody told them that writing earns you no money? It's generally a terrible business model. But I understand. I understand. Entrepreneurs, they are also communicating.

2:39Yeah, entrepreneurs want to get their message out there. They want to create value for others. They want to leave a legacy. They feel like they have something to say and something to give and something to offer. And that is Amber, someone who helps entrepreneurs say the thing they want to say, or at least write it. My name is Amber Ray. I'm an international bestselling author, speaker, writing mentor. I support people to get their writing done and write the stories that they long to write and put out into the world. I met Amber at an event many years ago, and she actually spoke at an entrepreneur conference in, I don't know, sometime in the pre-pandemic world.

3:15All that time is smooshed together. Anyway, we were catching up recently and she was telling me that when she coaches entrepreneurs in writing, a lot of them make the same mistakes. And they're not exactly the mistakes that you would think. They're not like rookie writer mistakes. They're mistakes about the kinds of things that they should be writing about or want to be writing about and who they're even writing for. It was really interesting. For example, she says that entrepreneurs often think too early about their audience, and that limits their imagination. It seems counterintuitive, but if we consider the audience too soon, we tend to create what I call safe writing or should writing.

3:58And you don't want safe writing. Safe writing is boring writing. You don't want should writing. I really like that phrase, should writing, which is to say the thing I should be writing about. because when's the last time that somebody did something just because they quote unquote should and it was interesting or compelling or exciting? No, there's something deeper, something that Amber wants you to dig to. That's what we're going to be talking about today on Problem Solvers, the common mistakes that writers make. And for what it's worth, if anyone wants to work directly with Amber, she has a way to do that.

4:35My offering is called On the Page. It's a accountability, the coaching, the community and the guidance to get your writing done and to write more than you ever thought possible. And how can people find that? People can find it at amberray.com slash on the page. But Amber has value for you right here, right now on Problem Solvers. We're talking about those big mistakes that entrepreneurs make and helping you become a clearer, better writer who's going to find that audience. Don't think about them too soon. they come to you when you have something truly special to share. Coming up after the break.

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7:14That sounds counterintuitive, Amber says, and it does. It sounds counterintuitive to me because don't we want to think about audience? Don't we want to serve audience? But as she said, when we think about audience too soon, we tend to create what she calls safe writing or should writing. And I've worked with a lot of entrepreneurs to get six-figure book deals or to figure out how to get their message out there. And they'll come to me and they'll say, this is the thing that makes sense. This is the thing that I feel like I should say that my audience is expecting of me. But there's this like kind of bold, brave idea over here that I've been thinking about and can't really stay all night.

7:52It's keeping me up. But it's a little crazy and wild and maybe it's too much. And I'm always like, whoa, let's go there. What's that? Let's unpack that a little bit. And there's always a merging process later of, okay, let's edit this down and really think about how we can deliver it based on what we know about your audience. But if we are considering them too soon, I think we don't allow ourselves to become more original or innovative or creative in what we have to say. I remember a conversation with an entrepreneur recently that was like that, but I think went in the wrong direction. So I want to tell it to you.

8:29It is, have you help people refine what it means to recognize should writing, which is a great phrase. I really love that. And, and this thing that they're excited about. So I was talking to a founder of a online mental health company. And she has been doing some writing on mental health, which is smart. But then she's also really interested in cryptocurrency. And I think I want to start writing more about cryptocurrency and doing cryptocurrency on my social medias. And my advice to her was, please don't do that. Because the thing is, it's just so deeply unrelated to the thing that your business is.

9:13And I suppose if you wanted to have a completely separate part of your life where you're like, I run this mental health company and also I am really into crypto, then that's cool. But if you want to think about how your writing can drive the central purpose of your work, then I would think about how can you find real purpose in communicating about mental health. And I'm curious what you would do in a situation like that, because the advice that you gave, which I realized isn't necessarily built for go write about cryptocurrency, mental health lady. But I bet a lot of people might hear that and say, oh, thank God, I don't have to write about sales and marketing, even though I'm a sales and marketing expert, because actually what I'm really interested in is birds.

9:56What should people be thinking about and how should they be navigating that difference between what passion they're carrying around and what they feel like they should be doing? Great question. So when it comes to the cryptocurrency, I agree with you. Weaving cryptocurrency into a mental health story is challenging. It might actually be the creation of mental health problems. Totally. Not to say go explore that on the side. Oh, it's there. I own some Ethereum. It hasn't been good for my mental health, but I do own it. Yeah. So maybe follow that spark. Maybe you find a cryptocurrency blog to participate in.

10:33I think that would be a separate avenue. But if you're looking to have it live under the same umbrella, I'm not saying go off into these crazy topics, though birds actually could offer really interesting lessons. Who knows what you might discover through bird patterns or bird watching that actually could be relevant to your message. It's more if we're thinking, will this resonate? Will they like this? Is this going to land a little bit too soon? I think that we get in the way of what it is we're really trying to say. And this is like a separate tip, but I think entrepreneurs and writers often censor their first draft.

11:12And so they will be writing and thinking, is this good? Will this resonate? Is the sentence okay? Like that editor is active while they're writing. And I always encourage to write freely first and edit later to get that brave draft down because the brave draft is not the final draft and the brave draft can also be a bad draft. But it's more about allowing your imagination and your creativity and your truth and your own personal, relatable stories to come through, knowing that you can always edit and refine it down later. Something I've discovered as a writer, it took me a long time to get there, was that there are two ways to use your stories.

11:52This is when you just said that, explore your stories and engage with them. It made me think this. In the past, I used to think I need a good subject. I need to know the topic that I'm writing about. and then I will find anecdotes that fit it. And now I actually operate differently. I operate story first. So it is, what is this engaging story? What happened either to me or to somebody else? And then once I know that story connects, I think, why does it connect? Or how could it help somebody identify something in their own lives? Or maybe by understanding why this person did this thing in this story or why it worked, I have a lesson that feels surprising and counterintuitive and also really organic to this story.

12:41And the story is the thing that people are going to remember the most anyway. Absolutely. So I love what you're saying there about just make room for the story, almost let that be your guide. Those are the things that are, those are the things that are animating you to communicate in the first place. Exactly. And those are the things that resonate and connect with others and make your message stand out. Which this reminds me of another thing that I see entrepreneurs do all the time is they leave themselves out of the story. So they think, okay, I'm gonna focus on the advice, the how-to, the value.

13:14This is what I want them to learn. Here's the call to action. They've got all of that down, but they forget that story piece, whether about them or someone else. People love to read about our founders' mistakes, lessons, insights, things, failures, things that went wrong because then they read the story and think, oh, they're human. Oh, I can relate to them. Oh, I feel more connected to what they're creating. And I often see entrepreneurs being like, oh, it's not about me. I don't need to include myself in this. When really, if you can look at your mess is also part of the message. I think it creates content that's far more relatable and personal and connecting for your audience.

13:54And what's funny is that both of the things that you just said, the thing that you just said, and the thing that they're worried about can both be true and still live in harmony. I'll give you what I'm thinking here, which is that, so you get entrepreneurs who say, it's not about me. But here's the thing. When you write about yourself, even then, it's still not about you. Because your reader is seeing themselves in you. Like writing about you is actually writing about the reader. It's giving them a moment of a mirror to see what you did. And then they start, they say, oh, I did the exact same thing.

14:29Or that's what I thought to do. Or, oh, so it, and I always think it doesn't matter who I'm writing about. I'm never actually writing about them. I'm just writing about the reader and the reader is going to see themselves in whoever I'm writing about. I'm so glad you said that 1000%. And I think the more personal we can get in our own making this about me, but it's really not about me, the more universal it actually becomes because the reader is, oh, that was me. I was sitting in that. I was feeling that. I was thinking that it is the mirror for the reader to see themselves more clearly. And when the entrepreneur is brave enough to really go there in the storytelling and share those raw, honest moments, I think their readers or their audience will see themselves even more deeply.

15:10And it will even open up parts of themselves that maybe they didn't have language for, or maybe they couldn't yet see. and it's this, then this creates this just like beautiful resonance. So talk now to the person who's listening to this and is thinking, I don't even know where to begin. I don't know what of my own experience is interesting. I don't know how to describe it. I'm not afraid of it. I'm not afraid of sharing, but I don't know how, what part of me is interesting? Yeah. So I would take a sheet of paper, set a timer for five minutes and make a list of three to five recent messes, like the idea that your mess is your message, messes in your life or business.

15:52And then put an arrow next to each one and then ask yourself, okay, what was the message or the lesson of this? And that could be conflict in the workplace. It could be, we made a mistake launching this. It could be the audience didn't validate this in the way that whatever it is, there can be a range of mistakes, or I thought the timeline of this would look like this. And it looks whatever it is, what are those messes? And then what is the message or the lesson for each? In five minutes, that will help you mine for material and have great things to share. That's great advice. I'll tell you what I do, which I'd be curious if you think is wise or can build upon, which is I am always now thinking, is this worth sharing?

16:35At every moment of my life now, it's worth sharing this story that And I tend to catch myself in moments of conversation where I'm telling a story about this thing that I just heard, this thing that I just did, and someone's really interested. And they're like, oh, that's, wow, that's great. And then I think to myself, ah, if this person is interested in this, possibly others will be too. And then I write it down. I'm basically using my regular life as a sounding board for what is worth, frankly, just turning into content. And that way, I'm never sitting down with a blank piece of paper and just thinking like, oh, what stories do I have to tell?

17:10Because I'm just catching them as they're floating around the air. Yes, a thousand percent. I also do that. I have a little notebook I carry around with me that says clues on the cover. And it's just every day, those moments, those conversations, the things that resonate, which is also the writer's dilemma, because I'm like, oh, God, I'm not present in this conversation because now I said something and they responded to this. And now I want to capture it. I can turn it into a story. And so I find that I have to balance the, ooh, this is really great material with how do I show up in a present way for this?

17:43We've talked in the abstract so far. Yeah. Yeah. I actually, in that instance, what I generally do is that I just start explaining what I'm doing. People always love, hey, what you doing? What's your process? And so if something happens in a conversation and I'm like, oh, that would make a great newsletter. I just, I tell them that would make a great, do you mind if I just write that down? Cause that would be a great newsletter. And then I like, as I'm doing it, I'm like, this is the thing I do is like, whenever something happens and I think that it'll make, I just like, I got to write it down.

18:15And I find that actually people are generally really, I don't know if honored is the right word, but they're really delighted that they were part of an idea generation. And then I kind of love, I love letting them be a part of the full cycle of it. This just happened actually, which is that I was in a city doing a speaking engagement and I had dinner with a friend and then she was driving me back to my hotel. And we were chatting on the way there and she was telling me this thing that she's been grappling with and I gave her some advice and she liked the advice. And then I was like, that advice is, that's good for a newsletter.

18:51Do you mind if I like share a version of this? I'll take every identifying piece of information out, but do you just mind if I share this? And she said, no, go for it. So I, first I wrote it down and she was into that. And then I wrote a newsletter about it and I sent her the first draft and I was like, I just want to make sure that you're okay with this, even though nobody could ever know that it's you from this. She reads it and she loves it and she has some thoughts. And then I can't wait to send her the thing when it's out. And I've done that with so many people and they always love it. Let people be a part of the story that you're telling.

19:21Yeah, a thousand percent. And often, I don't know if you find this, I find people are like, you don't have to change details. I don't need to be a nod. You tweet me at the story. Yes, I have found that. It's really funny. So Amber, what I was going to say there was, was that we've been talking about how to find the thing that's worth writing, right? Versus the thing that you just think you're supposed to write. The next step, I think for many people is, okay, the hell do I do with that? What am I supposed to do with that? Do I write a book? Do I start a blog? Do I make a newsletter? I like writing.

19:55I don't know where I'm supposed to write and I don't know how I'm supposed to share these stories. How do you guide people? It depends on a lot of factors. It depends on what their goals are. It depends on what their platform is. It depends on how they want to get the message out there and what they want to commit themselves to because a book is a multi-year project. And I think sometimes people don't realize the time that you have an idea to the time you get an agent to the dime, the proposals done to the book is out can be three years. two to three years. If they want to do it, if they want to do it, traditional publishing.

20:32Are you ready for that journey? Granted, books are life-changing, can lead to speaking, booking corporate speaking gigs and speaking careers and all kinds of things that are much easier to get once you have the book, which many years ago I worked with Seth Godin and I helped him start a publishing imprint with Amazon. And we were all focused on manifesto style books. And so they weren't 250-page books. They were like 90 to 110-page books. Just the manifesto because the death who's all about how ideas are viruses and how do we get these ideas out there. It's this manifesto is the distillation of my worldview, my perspective, my life-changing formula that I want to get in the hands of as many people as possible.

21:16And so a book is a great vehicle to do that. I think something I often recommend, even if someone wants to write a book, is to turn whatever they have to say into a 10 to 15 minute keynote because it helps them really distill what they're trying to say and to think about how they would sequence the story and the message in a very short, big picture framework and style. And then to invite five to 10 friends over or colleagues or people at the workplace and to share that kind of manifesto style keynote with them as a way of getting immediate real-time feedback on the concept. And just the exercise of creating that for yourself, I think helps you figure out how to make what you're trying to say this big picture story or idea really tangible for others.

22:06I love that idea of forcing yourself to do it in that function, because if you can do it in a keynote, you can do it in any other format. is in a way the hardest. It requires a very natural flow. It requires you to be able to do it in common language with ideas that are going to connect on the fly with people. It's very different from other kinds of work. What you said there reminds me also of a couple other, if you can do it in this way, then you have clarity on your offering, which is number one, can you write a good headline for the thing that you're trying to write? If the headline is not clear, then it's because you aren't clear about the purpose of the thing that you're writing.

22:54And the other one is, I've heard this from a lot of podcast producers who talk to people who have podcast ideas. And they always say, tell me what the hundredth episode of your podcast is. Because oftentimes people come in with this very hyper specific idea of something that they want to do that really carries for three episodes, but isn't replicatable past that. So you got to know if you're going to get into a form of communication that is ongoing. Writing a book is one thing. That's a solid singular object. A podcast is not. So if you're thinking about communicating in a different medium, a newsletter could be this too.

23:31What's the 20th or 30th newsletter edition that you send? If you don't know the answer to that, then it's really hard for you to move forward with a concept. What do you think about that stuff? I love that. I think that's a great idea. It allows you to really think about the journey that you're taking the audience on. And it reminds me many years ago when I worked with a speaking coach, she led me through this visualization and I was on stage and my ideal audience was in the audience. All these people who are my perfect people that I wanted to reach and speak to. And then she said, okay, what is the one thing you leave them with before you walk off stage.

24:05The one thing you want them to remember. And that's actually how I landed on my first book, Choose Wonder Over Worry, was that I wanted them to like the last thing. So when you go out today and you have the option of I can choose worry or I can choose wonder, I did that whole thing. And that's when I realized, oh, that's the title of my book, Choose Wonder Over Worry. And so that's a little bit different than what you're talking about. But I think distilling into what is the thing you're really trying to say and then And what's, does that have longevity, which is what I think you were just speaking to with the 100th episode, 20th newsletter.

24:39I think the combination of those two things is a winning one. Yeah, and I've seen a version of that talk, the Wonder Over Worry talk, and it was excellent. Right. Yeah, you did it at an entrepreneur event years and years ago. I also, that also reminds me of, a quick anecdote and then final question. The quick anecdote is, what that also reminds me of is something that I've done to evolve my keynotes, which I'll share in case it's useful for folks listening, which is that I would do a keynote and then I would get off stage and I would talk to people and I would take very careful note of the things that they told me resonated.