Wes Wheless - The Expert's Privilege
DH ### Wes Wheless
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Introduction
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Jonathan Stark: Hello and welcome to Ditching Hourly. I'm Jonathan Stark. Today I am joined by guest Wes Wheless. Wes, welcome to the show.
Wes Wheless: Thanks, Jonathan, good to see you.
Jonathan Stark: We are gonna talk about Wes's new book, The Expert's Privilege, and also probably some of the publishing process, because I do like to talk about that. But first, Wes, could you tell folks a little bit about who you are and what you do?
Wes Wheless: Yeah, sure. My name is Wes Wheless. I am based in Seattle, Washington. I've been out on my own, or post-corporate as I like to call it, since 2022. The big umbrella over what I do with folks is I help mid-career professionals find their lane as independent consultants. I do that in a couple different ways. First, if you're still in corporate and starting to feel itchy or vulnerable about your corporate career, then I can work with you to start to uncover the real expertise that you've built up over the course of your career and start to envision the consulting lanes for that and validate that in the market. On the other side, if you're already in market, you've left corporate, you're serving clients, but maybe you still haven't quite figured out your niche, then I have a positioning intensive that I do with folks. My signature part of that is that I help turn your expertise into visual IP. I create signature frameworks and visual explainers that help you explain what you do in the market.
Jonathan Stark: You're not using the visual, what did you call it, the headshots thing? Intellectual headshots, yeah.
Wes Wheless: Intellectual headshots. Yeah, kind of like headshots of your expertise. That is how I branded that service for the last couple years. I don't know, some people get it, some people don't. I think it's hilarious.
From Corporate to Consulting
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Jonathan Stark: Well, cool, so let's jump back to when you were, before you were pre-corporate or post-corporate. So when you're pre-corporate, you're current corporate, what was your corporate background?
Wes Wheless: Yeah, so I started my career in consulting. I was at BCG as an associate. Fast forward through a few different roles. Went into tech and I was a product manager at Expedia for a while. Then was laid off during COVID, went and joined a startup where I started building courses for product managers and engineering managers. Kind of cool role, I was sitting with tech execs and pulling things out of their head and turning it into courses. Then got laid off from that in 2022. So then it was kind of like a, I like to say, lay me off once, shame on you. Lay me off twice, shame on me. So I started thinking, I think I need to do something different and that's when I decided to see if I could get consulting work on my own and yeah, that was 2022 onward.
Jonathan Stark: Okay, great, so that, I don't wanna jump all the way up to the book. So what happened in between that and the book for you business-wise?
Wes Wheless: Yeah, so when I first started out I was getting, it was kind of nice and kind of almost the typical arc for folks is that you go out, you wonder where work is gonna come from but more often than not, the work comes from people in your warm network who find out that you're now available and seeking independent work and then asking you for help. So that's what I started doing. I mentioned I was building kind of premium courses for product folks based on executive expertise. That's exactly where my inbound started coming from. So SaaS companies saying, hey, our founder has a lot of ideas but we don't know how to put that out into the market.
Jonathan Stark: And so they would hire someone like me to come in and pull it out, make sense of it, create written and visual content that essentially was put out for content marketing. Sounds familiar.
Pivoting Toward Solo Consultants
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Wes Wheless: Yeah, yeah. So that's what I did. That was my first year, year and a half of work and then I started noticing some holes in that business model and also just pieces of that type of work that I didn't really love. So things like this was exciting work for me but it also was kind of low priority on the client side. So I was getting kicked around on the calendar a lot, like no fault to my clients but it's just like not the most. It's not high priority. Yeah, so that had trickle effects into something that seemed like it might take four to six weeks was taking two to three months and then that just kind of has impacts on your business model pipeline and then also kind of your own psyche, right? So I started working with a coach. Her name's Melissa Lieberman. Some people might know her and we started thinking about, all right, you have a special skill set. Who are other people that could use help in pulling things out of their head and making sense of them? And she said, hey, I work with independent consultants all day, every day. A lot of them could use some help in that regard and I did a bit more research and interviews to make sure, that's a big pivot and as I explored the market, then I started thinking not is it only more interesting to me because I'm also very, very close to that experience. It also is a much more urgent problem in my opinion because it's people that are going out on their own for the first time who haven't had to sell their expertise independently and that is the lifeblood of their new business. So all the pieces lined up. I said, okay, I'm gonna make a hard pivot and focus solely on helping other independents and yeah, from there, partly by your help, I started writing a newsletter about pulling things out of your brain, a daily one. Yeah, I describe it as an email about monetizing your corporate expertise and yeah, that was really helpful to get my own thoughts out and in front of people and flesh out some frameworks in public and before you know it, I had an archive and had built up some authority and so then the question of a book started becoming more and more end of focus.
Jonathan Stark: Cool, okay and in that process, the email list, I'm on the list, The Lightbulb, it's great read, totally recommend it, especially for anybody listening to this show. I mean, it's completely useful for that kind of person.
Daily Email, Authority, and Visual IP
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Wes Wheless: Thank you.
Jonathan Stark: Yeah, sure, and you shared a lot of, I don't wanna say success stories from clients but like IP that you created with clients at the time. So you were working through that period with people doing this before the book.
Wes Wheless: Right, yeah, I was sharing my own frameworks about the transition into independent consulting and niching and pricing, all of those types of things. But then I also, as I got into the visual IP work with clients, I would share those as case studies and really try to help people think about how you could articulate your expertise visually.
Jonathan Stark: Yeah, it's really arresting, I think, when you see it. When you see a four square chart and people's got the four quadrants or like, but yours are, a lot of them are the ones that you come up with with your clients are more of an illustration or more, not cartoony but they'll sometimes have a person or like a rocket or something. Tons of them just immediately communicate what would probably otherwise take a slide deck and 10 minutes of discussion to get the idea across. Visuals are a great way to communicate, and I have to imagine it plays very well on social media too. So for experts that are probably, well, a lot of them are either allergic to social media or they haven't really had to do it for business purposes in corporate, it's like, well, what do I do on LinkedIn or what do I do on Instagram or like, do I even need to do that? Do you find that your folks, the sort of case study folks, is that where they're using a lot of the assets? I'm sure they put them on their website and maybe they put them in a book, but are they also useful for social media?
Wes Wheless: You know, social media seems, it is the obvious one for some of the types of visuals that I create with folks. I think where they also get placed is, yeah, on their website, in proposal decks, also things that you can pull out on a first client call to essentially center the conversation. Yeah, it helps in the marketing funnel but also through the sales process. Some of the more, as you put, arresting ones, like those are the ones that you're like, okay, well, that will stand out on LinkedIn, go ahead and do that. And it articulates and grabs the client's attention, particularly those are the ones about visually explaining or depicting a pain point that the client is having. Those are really good on social. Other things like if you've been thinking about your problem a certain way for a number of years and we finally get into a, you know, maybe it looks like a simple two by two. Maybe it's a time series, like there's a few different ways that are really helpful for that. Those land less well on something like LinkedIn because they do need more than the like two seconds that someone on LinkedIn will give it. But in the right time on a first prospect call, you can say, hey, I'm going to share my screen and pull up a framework. And then all of a sudden someone was like, oh, yeah, this is exactly what I've been looking for. And then it deepens the conversation.
Jonathan Stark: Yeah, like, oh, I'm right there on the graph. I'm in that corner over there. Yeah, exactly. And then all of a sudden, the prospect is using your language and your framing and your context. And you've immediately established yourself as the expert in the room. Very cool. Yeah. I hadn't even thought of that. But if you are creating, I mean, if you're taking a framework and making it more visual, then of course it would work as a diagnostic or in a sales meeting or something like that. Yeah, that's really cool. So, yeah. So let's get into the book itself. The Expert's Privilege. It's got a little guy in a parachute on the cover. Tell everyone the subtitle.
Wes Wheless: Yeah, the subtitle is a self-deployment guide to leaving corporate and going solo. And how much of the book is about the idea of making your IP visual? Or is it more about the process of setting up a new consulting business? Yeah. So just one chapter actually is about making your expertise visual. It's something towards the end of the book. And it's a great place to start because when I started thinking about writing the book, of course, my mind goes to, well, let me write a book based specifically on what I do with clients. And so it's a kind of a natural sales tool for that. But as I got into it, I felt like, well, one, I wanted a few more reps at that type of client work to really feel like I had a really great book to write in that specific lane. But then also working with, I can talk about it. I worked with someone who refers to themselves as a book midwife, and we did a more broad brainstorm about what kind of book I was looking to write for my business. And I leaned back more on, well, what have I been writing about already? And, you know, what are the frameworks that people have responded to, like that my audience has responded well to? And is there a story in there that's a little bit more upstream? That's just about recognizing that you have, well, some discontent in your corporate life. You have some expertise that you've built up over time. And, you know, here are the first few steps of if you wanted to, how could you build a consulting practice around that? So that's why I decided to go broader and knowing that the book would essentially land towards the end on that piece around visual IP. But tell the story leading up to that just to build a bit more, kind of a broader top of funnel, essentially.
The Expert's Privilege
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Jonathan Stark: Yeah. I mean, there's a guy named Dean Jackson, I think his name is. And one of his most genius frameworks or rants is about not writing the book that your clients need when they hire you, but writing the book that they're looking for 18 months before they would hire you. Like if you're a realtor in Miami, what are people who are going to buy or sell in Miami wondering about 18 months earlier? They're wondering about things like the school systems in the area or if they're coming into the market, the houses they're selling for, or comps, or cyclical patterns in the Miami housing market. So the things that you start thinking about before you're ready to actually make a move. And so when people buy the book, it's like raising their hand that in 18 months, 12 to 24 months, they could very well need exactly what you sell in the future. It seems like a pretty long game to write a book that's more upstream of where your clients live, but it's kind of genius. I can't vouch for it personally, but it makes tons of sense. For someone to just spend nine bucks on a book or 20 bucks on a book is a strong enough signal that you could be like, oh, wow, here's this list of people that bought the book 18 months ago. I should probably send them a postcard or something if you're a realtor. Anyway, long story, but I think it's probably going to work out pretty well. It seems smart to me for you to have done that. And also, it seems like there would be very high demand for people right now for some kind of resource about what to do to maybe they were redeployed into the workforce against their will. Tell us a little bit about the arc of the book. So what are the big beats of the book?
Wes Wheless: Yeah. Well, and just to talk a bit about that, about the 18 months before, around the time I started the newsletter and when the book was just kind of a tiny seed in my head, I went to my 10-year reunion for business school and I started talking to people about what I was doing and how I'd gone solo and all of that. The conversations were all about, okay, well, I'm miserable in corporate or I can't do this for much longer. I need to know more about this. How did you think about the transition? So I knew that there was already some demand circling in there about this idea of mid-career slump, lull. Things didn't necessarily turn out as you thought, even if... I was talking to people that finally made partner at the big consulting firms and they're telling me like, okay, I did all the things and now I feel like I don't want to do this anymore or I'm feeling trapped or I'm feeling vulnerable, given the layoffs even then were starting. So yeah, when I decided on the broader arc of the book, I knew that there was something like that brewing and that there would be some demand eventually. But yeah, for the overall beats of the book, let me just define how I think about the expert's privilege and what that concept is. The simplest way to put it is that as you build up domain expertise, you essentially unlock powers. It sounds like a very simple concept, but you think about those people that I was just describing at the class reunion are almost a bit blind to what they've actually built up over all those years. They know they climbed the totem pole and they know they climbed the ladder. But then when they think about what to do next, we have blinders on about what we've built over time. I was pretty amazed at what happened when I went independent, even to my first proposal meeting of how the power dynamic shifted from one day I'm an employee at a startup and feeling like I'm getting looked over and put in the corner. Then I go into a proposal meeting where someone needs what I can do. All of a sudden, I'm the expert in the room. They're hanging on every word. They're asking me, okay, well, how do we do that here? I remember in the moment of that conversation, and right after I got off the call, I was like, that's strange because four months ago, I was the same person with the same head on my shoulders. Four months later, I'm sitting in a totally different context, but now I have the leg up. That trickled into me being able to articulate how I wanted to show up for them or what my prices were, or even when we start. It's all those things that you get to activate once you recognize your expertise.
Jonathan Stark: So let me jump in there for just a second. In that story, was the sales meeting with the hot prospect who really needed what your capabilities were, was that revealing to you that it was valuable or did you feel like before that it was valuable? In other words, was this an internal revelation more or more of a like, oh, wow, there's a huge difference between different kinds of buyers if you want to call your startup boss your buyer? Is it a framing thing? Like, how aware of it were you?
Why Corporate Experts Undervalue Their Skills
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Wes Wheless: You know, I think to answer that, you have to put myself back in the mindset of where I was towards the end of my last job. I knew that I was hired for a specific skill, which was pulling ideas out of people's heads. But at the same time, when I had new ideas for how we were doing things, they were kind of getting dismissed. I was having promotions promised to me that never materialized, which added another weight on me. So, it was just like, I knew I had skills, but I also knew that I had kind of hit a limit with how I was being valued at that company.
Jonathan Stark: Yeah, see, that's what I'm trying to tease out for the listener who's in the situation now where they're still at the startup and they're perhaps feeling like the skills that they have aren't that valuable because of the way they're being treated in the organization. Not necessarily that they're being treated poorly as a person, but it's just a low priority thing for the organization. So, of course, it's gonna get bonked around the calendar and so forth. But I imagine that could be transmitted or received by the expert as, "I have all these skills and I know I can do them, but they're not that valuable." People might reschedule a meeting 10 times and not take any of my advice. There's a type of person who's immediately gonna have the sense that it's their fault. They're just the wrong audience for this thing that they can do, and they're gonna naturally go look for another audience who values it more. But I think most people are not like that. I think this might be why the skill is invisible to them. I'm just speculating, but it might be invisible because you build it up slowly over time, like your hair growing. You don't notice it every day. But then you're also getting this signal from the organization that it's not that big a deal—passed over promotion, rescheduling, not taking your ideas. So, I would say to people listening, if you feel like you're in that situation and you, deep down, have a feeling that you're really good at something that's probably valuable, then it could just be the difference of picking a different target market. In your universe, your reader, it's not really picking a different target market. It's like you're in corporate and there's all of that. And then going solo, it's kind of like picking a different target market. You're getting paid by someone different. But it's a much bigger leap because now you've got all of the business setups, things in marketing and sales and all that stuff that you didn't have to do in-house. I'm just trying to help the person listening who might still be in corporate and feeling like they don't have a valuable skill. I hear this from people, like, "I don't have a valuable skill. I don't know, they might know what they're good at, they might know what they like doing, but I can't make a living at this. No one cares about it or whatever." And so I imagine that it can be pretty demoralizing. Anyway, I'm tempted to soapbox about this, but you tell me, what is the psychology of someone, if you had early readers, what are people saying to you about that? You know, like valuing, getting a new valuation. I guess that's what it is, getting a new valuation on their skills.
Wes Wheless: Yeah, well, I mean, I would add another layer on that. Put yourself in the mindset of, let's talk about someone who's, let's say, at a big tech company. I don't know, let's say they're a product manager. That's very close to my heart. But you're also getting the signal that you're one of 1,000 product managers. So it's not a far leap to just start to think, "Oh, yeah, I'm just another one of them, that this company's gonna be fine without me. What's special about me?" And then you're almost not surprised when you get laid off because you are just another number. And so, yeah, that's where it gets into this mindset of, you know, no wonder you struggle to identify and articulate your own expertise because it's kind of been generalized for you that you've just been put in this box that this company either needs or doesn't, and that decision really isn't up to you.
Jonathan Stark: Yeah, okay, that's good.
Excavating Your Expertise
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Wes Wheless: Yeah, and then when I start to talk to people, and I put a lot of this in the book, is you need to think about the unique constellation of things you've picked up over time. All the places that you've worked, all the things that you've seen, all the types of people that you've worked with. Like, that all leads into something that's very unique and highly transferable. And it just takes some work to excavate that. And then also started asking a lot of self-examination questions about, what do you actually like to do? Who do you actually like to work with? How do you show up best? Because it perhaps is not, you know, I talk a lot about efficiency of deployment. I think that, you know, filling a box at a company, you know, you're hired to do a certain job, but a lot of your time gets taken up with other things that are not right in that zone of genius, right? What if you could design something where you're staying right where you should be in terms of where your unique lens lands on a problem? So yeah, there's all of those things going on. And the way I break down the expert's privilege, and I think it's a helpful three-step, like, it's three sequential ideas. One is that you've, over your 10, 20, 30 years in corporate, that you have gathered a set of unique and valuable expertise. And that goes for anybody. I don't care what your title is or what it has been. It's like, you have picked up unique expertise over your corporate career. That's number one. Number two is that that expertise has been inefficiently deployed in the corporate grid for all the reasons I just mentioned. Think of all the time you spend in kind of BS meetings or security trainings, you know, all those things that are necessary for a corporate environment to continue to function, but take you out of actually deploying your expertise. That's the inefficiency that I'm talking about. So that's number two. So you are an expert is number one. Number two, you've been deployed inefficiently. And number three is that you could deploy your expertise more efficiently, independently by your own design. That's the core argument of the book is kind of waking people up to, yep, you've built something valuable. You can deploy it yourself. And then the second half of the book is, all right, how do we, what are the first few steps of turning that into an independent consulting practice? Not the entire manual on how do you build a consulting business, more just like how can you envision what that transition would look like so it becomes less of a black box?
Jonathan Stark: Okay, so that's great. I love, that makes total sense. I love the sort of three-step progression of the thinking for the reader. How do they deploy themselves more efficiently beyond just saying like, you know, cut out the middleman, air quotes, the employer and all of the, cut out all the corporate BS and be solo? How do they find someone who is going to value the expertise in a way that, you know, the client is hanging on every word and recognize the value? Like, do you have a sort of process for, let's say, experimenting with different niche markets or, you know, or is there something like reaching out to your network and finding specific people in your network? Going in a direction, like should you pick product managers who are, I don't know, recently laid off as a target market and either work with them or experiment with them, or is it more of a, is the book still upstream from there? Well, the book, once I introduce the concept...
Finding Your Zone of Genius
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Wes Wheless: The expert privilege involves some self-examination of where your expertise lies. The question then becomes, who needs help from someone with this type of expertise? You can start to chart out consulting lanes and have conversations in the market to validate that there's a problem to fix and that you're the one to fix it. That's the high-level arc. We could delve into all those pieces, but I like to start by helping people shed some corporate paradigms they might still hold. It sounds hokey, but it begins with asking, what do you like to do? What really lights you up? I've long been attached to Gay Hendrix's Zone of Genius framework. If you're going to design a business, why not start with where you operate most efficiently and at the highest level? I spend time in the book helping people think about that, with examples from clients. For instance, I had a client from big tech who was a UX researcher. It would be easy to say, let me find some UX research work, but as we dug deeper, we realized she enjoyed mentoring junior researchers. She then considered bringing her big tech UX learnings to startups, which kept her motivated to sell this type of work. You're not going to get traction in a business selling work you don't enjoy. It's like picking a target market you don't like just because they have money. You have to spend half your life with these people, so pick people you want to be around. The same goes for your zone of genius. What's the thing you love, are great at, and energizes you versus draining you? Especially if you're a soloist, you can't delegate the stuff you hate. You have to do all of it, so work with people you like doing something you enjoy. You get to design it and make all these decisions. You're in control, so why not pick people you like and do something that energizes you?
Jonathan Stark: Why do you think people don't do that? Why isn't their first impulse to design a consulting firm they would love running?
Wes Wheless: I think one reason is the default to what seems like it will earn the most, as you alluded to. But in practice, it's different. People find a first client, then another one appears with different work, and another with different work, and they just follow the work. Suddenly, they're staying staffed but not developing a lane or niche. That's when people come to me, about a year in, swinging from tree to tree without finding their lane. We take a step back to figure out what they really want to do, where they'll find the most traction, and articulate that. There's the academic side of making the most money, but in practice, you're just following the next project. When you're doing that, you're not building a business. You're essentially operating as a staffing agency of one, trying to keep yourself going, which doesn't help build a pipeline, authority, or a name for yourself—all things an expertise business requires.
From Self-Examination to Market Validation
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Jonathan Stark: Yeah, perfect. Okay, so once you go through an exercise, it's in the book, you would have the reader go through this exercise of uncovering the things that really light them up. What's the next step after that?
Wes Wheless: Yeah, so from that, well, I thought it was important to cut some slack, because you won't find someone who's gonna, like, well, I'm a big proponent of niching and specialization, but I wanted to be very clear for folks that you don't need to do that right away. More importantly, you do need to go find the first client, and that is okay if that work doesn't end up looking like all the rest of it. You just need to find it, whether it's something that you do as a side hustle while you're still employed, or if you've been laid off, or you've decided to shift to a solo career. Just focus on getting that first client, because you'll learn so much about sales cycle, pricing, proposal process, stakeholder engagement, like, all those things that you don't know, you really don't know until you're in it. So I like to park that there, but then I go into, like, the back half of the book is, all right, I know you can't do all this stuff right away while you're reading this book over a weekend, but I wanted to paint a picture of how this turns into a specialized consulting practice. So that is, all right, you've found your first couple clients, then you start thinking about, how do I move out of that generalist box, and how do I find a repeatable lane and ICP, ideal client profile? It's really important to internalize that niche approach, triangulate what I call a starter niche, and that's something that you can start to, and this is the kind of work I do with people, is, all right, let's put together a consulting thesis, like, a hypothesis, just pain, problem, your view on the solution and how you could be engaged, and then go shop that out in the market. Go talk to old coworkers that have moved on to other places, or people that have left and gone to startups are actually really ripe people to talk to, because they're the ones that need this kind of rudimentary help, and are unlikely to have people in-house that can do what you do. Just go talk to them and say, hey, I'm thinking about spinning out on my own, could you take a look at this, and does this hold water? Just have those kinds of informal conversations, and then you start to validate, okay, there's something here, or there's not. Before you move, I wanna applaud the pragmatic approach.
What to Do Before You Leave Corporate
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Jonathan Stark: I totally agree with you. Like you, I'm a huge fan of specializing, picking a lane, and developing IP around it and authority. You're 100% right; there's so much stuff that first year after you go out. It's a lot to get used to and develop systems around. Looking back, I didn't go straight to solo from corporate; I went to a small firm and learned almost all of that stuff there, which was fantastic. It was like a huge safety net because there were systems, clients, a pipeline, all of that stuff. I could learn what it was like to be a consultant, like a software consultant. I had a boss, but I wasn't really working with the boss; I was meeting with clients. It was very much like what came after when I did go solo. There's a massive learning curve there. Also, if you don't have a good cash cushion, you're going to make horrible financial and client decisions. If you've gone six months without a client after leaving or getting laid off, you're going to be freaking out. So getting that first client, figuring out your billing systems, pricing, and proposal process—all of this stuff you didn't have to do in corporate—is crucial. I love that. If anyone listening was wondering how I felt about that, that's how I feel. I don't talk to many people who just ejected or are thinking about pulling the ripcord. Usually, by the time I talk to someone, they've been solo for five years. It's easy to imagine people hearing advice from me or others and thinking they have to apply it immediately at the beginning. I'm glad you have this resource there. I think that's a pragmatic, practical way for people to look at things. So what's the picture you paint for them toward the end of the book? We're implying that having a lane, specialization, expertise, and authority are all good things, but I haven't really said why. Is that part of the picture you paint?
Wes Wheless: Yeah. It's one of the things I continued to play with as I was writing the book: what is the endpoint? There are so many consulting books out there, so much more I can continue to write, and so much more I personally have to learn about this world. The message I wanted to end on is that this is a transition into a new working model. If you're interested in going solo and follow these steps, finding your groove as an independent consultant, the goal here really is untethered flight. It's not a particular destination. I didn't write a "here's how to make a million dollars as a consultant" book. I think if you follow certain things, you can certainly build yourself a comfortable life. But it's really about where people start when they pick up this book. They start in corporate discontent, feeling trapped, and low self-worth. I wanted to land on a place where you've now shed all of that and are seeing the benefits of activating all these privileges: autonomy, creativity, curiosity, and all that energy you used to have at the beginning of your career that somehow disappeared in that grid. As I've started to talk about the book more publicly, I like to make clear that this is not a rant on corporate. It's not an anti-corporate book, and I'm not trying to convince everyone to quit their jobs and start practices. It's more of a way to rethink what the next chapter looks like for you and transition into a different way of working.
A Book Is for Someone
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Jonathan Stark: I saw an unbelievably good quote the other day. So if folks haven't already listened to the Brian Harriot episode we did, I think right before this one, he recommended a book called "Write a Must Read." He was so excited about that book that I went and checked it out. The headline on the page for that book is maybe one of the best headlines I've ever seen, which said, "A book is not about something, a book is for someone." Maybe that doesn't land for other people as hard as it hit me, but having written a couple of books, that couldn't be more true. It's funny because when someone says, "Oh, I'm writing a book," they always ask you what's it about. And it's not what it's about, it's who it's for. You just did a fantastic job articulating who your book is for. It's for that 40 to 50-something corporate employee that's feeling stuck or disgruntled or unsatisfied for some reason, and they're thinking about heading for the exit. Anybody listening that either falls into that category or knows someone like that, the expert's privilege is gonna be linked to that hook in their mind. So I think that's fantastic. For the people who might be listening, who maybe still are in corporate, frankly, I don't think there's tons of them listening to this, but maybe folks will share this episode with their friends who are. What's one thing that they can do while they're still employed that is probably safe to do as an employee that would help them smooth the transition to that untethered flight? Is there anything that they can kind of get away with doing while they're still at corporate?
Wes Wheless: Yeah. One very easy thing to do, and I think we all kind of overlook it when we're so trapped in the context of our own corporate role, is keep up with your old co-workers. Do that for a couple of different reasons. One, I say your old co-workers because they've moved on to a different context. It's important to understand how they're approaching the same problem that you worked on together at a different place. It starts to open your mind that what you're doing, what you know, the expertise that you've built up is in fact transferable outside of the company that you've been at for 5, 10, 15, 20 years. So that's the first thing. Let that kind of crack open the window so you can see that you can hold a conversation about this topic in another context. The other thing that unlocks is it keeps your network fresh so that if you are even thinking about testing out consulting as a side hustle, and of course, read your corporate agreements before you go and do that, then that keeps that connection active and warm. Maybe that's someone you go and reach out to, or they reach out to you saying, "Hey, we actually need someone like you to help us out on a contract basis." So that's one thing that they could do is talk to your old co-workers. The other thing, and this is something that you could probably do more easily these days with some sort of AI tool, is have your AI tool ask you to reflect on the problems that you're solving. We get so focused on milestone to milestone, day-to-day work in corporate, that it's hard to zoom out and say, "What am I actually doing? How am I thinking about this problem?" Sometimes maybe once in a while, you'll get asked to speak at a conference or something or do some kind of webinar. That forces you to think about your problem and what you do in a more broad way. But you can make that into a regular practice of starting to get your point of view together about your domain, which is just something that's very easy to kick the can on.
Writing the Book With Support
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Jonathan Stark: Yeah.
Wes Wheless: Cool.
Jonathan Stark: Those are all great and safe.
Wes Wheless: Yeah.
Jonathan Stark: Because whenever I do talk to someone in a situation like this, there's always that specter of like, oh, well, I don't want to get in trouble. I don't want to get fired. I don't want them to think I'm looking for the door before I've got a place to land and all of those sorts of things. So it can be fraught. But keeping up with people you used to work with, totally safe, totally smart. It's probably where your first client will come from. If your employer isn't your first client, I see that a lot too, where somebody goes solo, not laid off, but they just say, you know, Bob, that's been great, I'm gonna go do something different now. And that Bob becomes the first client because of like, well, we still need you to do some of that stuff. You know, could we hire you on a consulting basis? So that's all cool. This sounds like just an amazing resource for that exact person. So like 40 to 50, feeling stuck, been in a corporate job for 15 years, maybe longer. Yeah, so let's, if you don't mind, I know listeners, a lot of listeners are in the process of writing a book or thinking about writing a book and publishing a book. Can we just spend maybe five or 10 minutes on your experience of doing that? How you thought about it, the mechanics, real tactical stuff.
Wes Wheless: Sure.
Jonathan Stark: How did you publish? Was it self-published? Did you go through a small imprint? Did you try and shop it around? All of those sorts of early thoughts.
Wes Wheless: Yeah, so starting with that question, I self-published completely. I know some people do the large publisher or a hybrid. I went full self-published and I've been, I've kind of come to the revelation that that decision was kind of made for me. I feel like the, you know, it'd be really hard to attract a traditional publisher without bringing your own audience these days. And I have an audience with my newsletter, but it's not in the multiple thousands of people that are like hundreds of thousands of people that a publisher might want you to bring. So yeah, I went the self-publishing route. I think there's a lot of different reasons aside from the one I just gave you, but the other one I'll mention is that I just didn't want to go shopping for help for a year and try to like sell this idea. I rather just wanted to like spend the year writing the book and then get it out. And then also climb the learning curve along the way because I realized pretty early in this process that I don't believe that this is the only book I'm gonna write. And so I wanted to understand the nuts and bolts of the whole process and then who knows, the next book maybe I bring on a bit more help or find some publish, find a publisher.
Jonathan Stark: So what kind of help did you bring in, if any? Yeah, so yeah, that's the thing.
Wes Wheless: Self-publishing does not mean that I did this fully alone. So I mentioned I worked with a book midwife, which is just, if you've heard of a book coach, it's in the same vein. It's just a little bit more, I don't think my book midwife would mind me saying that it's a little more woo-woo. A little bit more, you know, deep reflection on the type of book I was feeling called to write. When I did get trapped in writer's block, it was kind of more meditation-based to get out of it. It was just someone who I trusted and who had a long track record of getting books out of people's heads. So I hired a book midwife who also served as my developmental editor. And then I also hired a copy editor and then towards the end of the process, hired a vendor to help with proofing, final upload to the platforms and those kind of last mile pieces.
Jonathan Stark: And where did you find all of these people, honestly? I mean, where does one look for a book midwife? I don't know, maybe Readzee or what?
Wes Wheless: The book midwife was a guest on a podcast that I had been a guest on a few years back. And then we just had a get-to-know-you conversations. We had been in each other's orbits. You know, they also were in the business of pulling things out of people's heads and so we had some common ground. And then when it, you know, they wrote a book called Claim Your Voice. The author, the book midwife's name is Fen Drowden. I can send you the link. But it was a book about writing a book and so that's how I found the book midwife. Then the copy editor was a referral from Fen. And then the last mile help, what kind of production help, was a referral from someone in my newsletter audience, actually, after I started mentioning that I was writing a book, then they reached out with that name.
Jonathan Stark: Cool. So, well actually that brings up the cover. So like you have a really cool, the cover is very unique in my experience. I don't think I've ever seen anything quite like it. It's a perfect little, of course, perfect little graphic for the idea that you're selling here. Where did that come from? Did you create that yourself or did you hire someone to do that?
Wes Wheless: Yeah, I created that myself. Like I did a first mock-up, even way back when I did the first outline for the book. It helped me make this feel very real for me. Yeah, it's funny how that happens.
Jonathan Stark: Yeah, so I did that.
Wes Wheless: And so that image has been burned in my head for almost two years now. Funny enough, when I got to the final step, when the production vendor, they had included in their package a cover design. And I was like, okay, well, I do need this like professionalized. So I sent them that and then they were like, okay, well, we usually like find some matching like stock image and we'll... And then I immediately just like pumped the brakes. I was like, you know what? No, this is almost exactly how I want it to look. And so let me just clean it up myself in Figma. And so that we ended up using my cover design. I didn't even see a proof from them.
Jonathan Stark: Wow. It also is something that oftentimes I've heard the advice of, all right, go to Amazon, go into your category and look at the best sellers covers and just replicate that. And I took the opposite approach. As I said, I don't want... When you go into the consulting category on Amazon, you see a lot of like corporate iconography. You can see a lot of like even dollar signs, things that to me are just like, this does not match the tone of my book, which is a very reflective and aspirational type thing. You know, I didn't want it to look like that. And I wanted it to match the visual frameworks that I included throughout the book. And so I was like, no, I think I want something that's a little bit more playful. So that informed the art and the colors in the book. How long of a process was this for you from like day one, okay, I'm sitting down to work on this in earnest to launch?
Wes Wheless: Uh, first meeting with the book Midwife was December of 2024. And we're now in July of 2026. And I just launched two weeks ago. So about a year and a half.
Jonathan Stark: Yeah. That sounds about right.
Wes Wheless: Yeah, and I did the outline three months after that first meeting. I started writing in October of last year. The actual manuscript, finished the manuscript in March. And then April through June, July has been production.
Launch Strategy and Early Results
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Jonathan Stark: I know it's on Amazon. Well, tell folks what happened when you launched. So you had this great little launch sequence that I enjoyed. What were the components of the launch sequence? And what was the immediate result, the aftermath of the launch?
Wes Wheless: Yeah, yeah. So I feel like I could have started a lot sooner. I had plugged the writing process in my newsletter, so there were at least seeds planted that a book was coming ever since December of last year, six months in advance. I started developing a list of people, a kind of a sub-list of people that were specifically interested in just updates on the book. I was doing an email campaign starting with them in June, once a week. For the first six weeks leading up to launch, it was email teasers. As I got closer, I started posting on LinkedIn two to three times a week with an introduction of what the book was and some excerpts from the book. More helpfully, it was me starting to put visual frameworks from the book. Those are the ones that really caught on on LinkedIn. So there was that buzz. When it came to the launch week, I set the public launch on a Tuesday because I hear that's when you're supposed to do it. Monday evening, the night before, I gathered just like 20 to 30 people that had been supporters or close to the process and considered them my launch team. I invited them to a private Zoom on Monday night where I shared a little bit more about the book, why I wrote it, what's inside, and how they could help me with visibility. This is kind of like Frank inside baseball talk. I also asked if they would buy the e-book so that when I made the public launch on LinkedIn and email and all the different places on Tuesday, I already had some momentum in the Amazon charts. The wave of purchases on Tuesday, on launch day, were able to get me to number one in a couple categories on Amazon, which I was then able to use to promote the book the rest of the week by saying, hey, we got to number one in job markets and advice and consulting. It's something that started to kind of feed on itself.
Jonathan Stark: Awesome, I had a ringside seat to much of it and I was very happy to see how well it came off, how well you executed, and that it's always fun to hit number ones.
Wes Wheless: Yeah.
Jonathan Stark: So cool, well, where can people go to find out more about what you're doing and maybe find links to a copy of your book in case they're a disgruntled 40-something in corporate or they know someone who is?
Wes Wheless: Yeah, definitely. If you just want to find out about the book, I bought westbook.com. I noticed it's a lot easier for people to type that in a phone than the expert's privilege. So you can go to westbook.com and then if you want to learn more about me and my services, you can go to either westwheless.com or planyourleap.com, which also goes to my main homepage. Plan your leap. Plan your leap, yeah. And there you'll also find the sign up for my newsletter if you want more regular updates from me.
Where to Find Wes
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Jonathan Stark: Great, well, thanks so much for coming on and sharing all that expertise and wisdom with people.
Wes Wheless: Thank you, thanks for having me. It's good to see you again.
Jonathan Stark: And happy 10th anniversary to your newsletter and your book.
Wes Wheless: I know, it snuck up on me. I was like, wait, 3,600 emails.
Jonathan Stark: That must be pretty close to 10 years, oh my gosh.
Wes Wheless: Yeah, amazing.
Jonathan Stark: It's nuts. Well, thanks for that. All right, folks, that's it for this week. I'm Jonathan Stark and I hope you join me again next time on Ditching Hourly, bye.
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