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A New Perspective On Being A Self-Employed Individual With Jeffrey Shaw | Ep. 20

BDD 20 | Self-Employed


With the way that society behaves, being self-employed is almost like being a deviant. Here to provide a new perspective and elevate your pride as a self-employed individual is Jeffrey Shaw. He starts off by defining what it means to be self-employed and shares the changes he’s observed in this space. If you’re having a hard time determining if you’re self-employed or not, join in as Jeffrey shares what differentiates a self-employed business from all the rest. He also talks about his book, The Self-Employed Life, and shares all the amazing knowledge you can gain from it. He also gives out some takeaway strategies and practices that will help your journey towards success. In this episode, know why you should be wearing your self-employment as a badge of honor.

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A New Perspective On Being A Self-Employed Individual With Jeffrey Shaw

BDD 20 | Self-Employed
The Self-Employed Life: Business and Personal Development Strategies That Create Sustainable Success

Jeffrey Shaw is back for a second time after sharing how to speak your customer’s lingo in episode 123. Jeffrey is one of the only few returning guests we’ve ever had. I am fired up as he’s bringing and introducing his latest book, The Self-Employed Life.

Jeffrey, welcome to the show.

Jesse, I thought I was going to have fun and hang out with you but now I’m even more honored to find out I’m a repeat.

It’s you and Shep Hyken. The two of you, guys.

That’s good company.

You got this new book. I need to know the origin of it. I know a little bit about your backstory but give me the origin of where this book came from.

I love that everything you’re about is standing out doing business differently because that’s been my whole life and that is the impetus of the book. To be self-employed is such a different way of doing business in the world. The problem is nobody has addressed our needs, literally. I’ll also put some of the onus of responsibility on self-employed people because they don’t own the difference. I’ll tell you how I know that in a logical sense. I re-launched my website last year and I hired somebody to do some keyword research. There is no one in the world searching for the term self-employed. I got to the point like, “What the hell do people call themselves?” The leading story in the book is I’ve been self-employed since fourteen years old. I sold eggs door-to-door.

I’ve never had a job and never received a paycheck. I’m like, “What the hell do people call themselves?” I started doing all this research and asking people. The closest keyword that people search for is small business. From a strategic standpoint, I rebranded my website focused on all keywords, Small Business but once you get there, you realize, I am entirely for self-employed business owners. The problem with calling yourself a small business is very practical. The people that I most care about and the businesses that are driving the economy, many of us are too small to be considered small business because small business technically is up to 500 employees.

Here’s where it’s a problem and this pandemic brought up an interesting point around it. I have a lot of connections in Washington, so when the PPP loans came around, I was able to read that legislation before it was public. It was the first time in US history a piece of US legislation mentioned self-employed people. One of the advantages of being in business for a long time like me, you see a lot of circumstances. Businesses that are fewer than 10 or 20 people could not get funding or have not been able to get financial help in the past because the US considered us monetize hobbies.

They put a limit that you are a small business if you had a minimum of 20 employees, maximum of 500. That left out scores of people. Those are the people I care about. I realized, in doing this research that no one is helping the small businesses or the macro businesses. Nobody is helping the self-employed. I even went to Amazon. I search books for self-employed. There aren’t any. The books that are there are things like taxes when you’re self-employed and how to make six figures when you’re self-employed.

It was all so unrealistic to what I know as a lifelong self-employed person. I had to write the book. I’m like, “There needs to be a resource guide for self-employed business owners that’s realistic that speaks to the fact that they’re not just in business for themselves but it is personal.”

How many times in business have you heard, “Don’t take it personally. It’s a business?” That’s not true. When you’re self-employed, it’s all personal.

There’s a link together. Theoretically, I’m self-employed. Not only to speaking and everything else. What do you define when you go from self-employed to small business?

It’s a personal choice. There are some technical divisions. I want to add here something. It’s significant looking down the road. Let’s say, grumblings. I don’t want to say too much but there’s talk of possibly being a whole separate department in the US government for self-employed business owners. We have the SBA and there is talk of them becoming a department for the self-employed. That’s how much the government is starting to recognize the economic impact of self-employed businesses. There will be some criteria, I’m sure, as to the size of the business. Be it sales or employees as there is for small business but right now, it hasn’t been determined.

To be self-employed is such a different way of doing business in the world. Click To Tweet

To me, it’s a vibe like, “How do you feel?” One of the advanced readers of my book is a CEO of a manufacturing company. When she read the book, she has about 40 to 50 employees. As favorably, she’d love the book. She commented that although the book wasn’t written for her size business, she got so much value out of it. There’s no definite number there. To me in a way, it’s how personal does your business feel to you.

That’s what I got linked up. Reading the summary and going through it, I was like, “There’s a link in my identity and a lot to the Bananas, it’s everything. This is my baby and my passion. It’s my dream.” Self-employed is almost your livelihood.

It is. The other cutting-off point is recognizing how you need to do business is different than small business, under the technical terms or big business. That’s what we’re surrounded with. We’re surrounded by the practices of big companies. I’m into cross innovation. I love to pay attention to what big companies are doing. I’m probably doing the opposite and putting my own spin on it because that’s what works for me. One of the distinguishable differences is a lot of most businesses are transactionally-based.

One of the ways you know you’re self-employed is your business is primarily relationally-based. How you run your business is so relationally-based. What’s important about that is what we see in the world. We see businesses that are more transactionally-based run promotions for new customers only. That’s the worst thing you can do when you have a relationally-based business. You want to have privileges and programs in your business that honored your steady and consistent customers.

There’s so much to value in this, knowing the people behind the brand. As you’re building your business as self-employed, you are the brand but as you even grow a little bit, the relationship and connection are missing. We do Facebook Lives with our team cooking in their own houses. We try to get behind the scenes and show our people. Almost everyone, you’re your brand within the business, relationship and connect with people. Is there something there as well?

It’s one of the advantages. It’s one of the things I have loved about this virtual world we’re living in because I love the opportunity to make it more real. You and I were identifying as self-employed business owners and having more of a personal brand. We are more comfortable doing a video or a virtual event or something in our living room or showing bits of our house in the background, whereas the CEO of a major company is going to be very hesitant to do that because they don’t have the same emotional attachment. There’s a wall between them and their business. There’s no wall between us and our business. In a way, it’s a fantastic opportunity. I’ll demonstrate it in another way that we know this is true.

A lot of people don’t realize the changes LinkedIn has made. LinkedIn has for so long been the online resume platform. I’ve always had a LinkedIn profile but not sure why. I never did anything with it because I’ve never been looking for a job and I don’t expect I ever will. That’s not where I would find employees. They have made major changes to the point that they are better now for personal brands than traditional employment. I interviewed someone on my podcast and she’s Marissa Polselli. When I found this out, I interviewed her and then I realized the changes. I had to redo my LinkedIn profile.

My views or engagement have skyrocketed. I learned so much from her. I wound up helping her develop a whole service called LinkedIn for Personal Brands because they can change the platform so good for self-employed business owners and us, personal brands. Even they, as big of a company as they are, have swung the pendulum to being more adaptable and a great way to connect with people that your businesses of one. You’re a personal brand.

LinkedIn has been a huge tool. I couldn’t agree more. I want to go into the actual book. Your book has three categories. First, defining the problem. There’s nothing there for self-employed people but what is the problem that self-employed people are fighting within a business?

There are two core problems. The one that stood out to me is every time I asked a self-employed person why they went into business for themselves, everybody has the same answer. They say something like, “I wanted to control my destiny, future and the hours I work,” to which I then reply, “How’s that going for you?” Everybody laughs because that’s the irony of being self-employed. We’d go into business for ourselves thinking we’re going to control our lives and we enter completely uncontrollable circumstances. That’s one of the core problems. The second problem is how do we get help for our business done differently. We wound up running all over the place. We will hire coaches for our mindset. We hire gurus for our strategies.

We go to conferences for training and then we’re accused of being all over the place, not having a niche and being a hot mess or we’re calling ourselves a hot mess but the world hasn’t put everything in one place for us. I’ve addressed both these issues. One is I develop and introduce what I call the Self-Employed Ecosystem, which consists of three primary elements. I call it an ecosystem because it’s true in business as it is in nature that if something is wrong in your ecosystem, it can kill the whole thing. I want to introduce this ecosystem concept. Self-employed business owners take care of the whole knot. Not the one piece they focus on, which tends to be a hustle. There’s a lot more to it than that. Otherwise, they’re working hard and hardly getting ahead. You’re a hamster on a wheel.

BDD 20 | Self-Employed
Self-Employed: Businesses with fewer than 10 or 20 people could not get funding or have not been able to get financial help in the past because the US considered them monetized hobbies.


The ecosystem introduces how to control the results you want by setting up the circumstance by taking care of the environment. If you set up the environment, it almost cannot happen. The three parts of ecosystem or personal development business strategies and the last are daily habits. This is lacking for a lot of people. It’s consistent mindsets and daily habits so that you can even out the ups and downs.

The concept of the ecosystem is it gives far more control over your business than you’ve had and strategies to manage what you can’t control, so you don’t get derailed and then everything is in one place. I’m a coach. I’ve received over 1,000 hours of training as a coach. You’ve got all my personal development knowledge. You’ve got my 36 years of business strategies and right-sized strategies for self-employed and you’ve got habits, practices and mindsets that I’ve been introducing to my coaching clients for years that I have absolute evidence that they left out the ups and downs.

I’ve started the miracle morning a few years ago, how you start your morning, I read, write and stuff. It changed everything. You started your day on purpose. Those certain habits have been a big way. I’ve shared that with the audience here and personal development. You’ve got to keep growing, learning and developing. That’s so key. I do want to dive into business strategies. I want to get in because there are some unique things that you bring up in the business strategies that I want to go into more. You start with Hug Marketing which that’s a great term but I want to go into that a little bit more the business answer to getting control.

I do refer to those right-sized business strategies. We’re not trying to behave much bigger businesses and what the differences. Hug Marketing is the one a lot of people are latching onto. It struck me interesting when I launched LINGO, how many people describe me as being disruptive because I think I’m the nerdiest guy on the planet. I’m not cool enough to be disrupted. I don’t even wear torn jeans. My jeans are oppressed. In a lot of ways, I realized that my philosophies are disrupted and Hug Marketing is one of them because one of the things that have pissed me off for years in business is the idea of a marketing funnel. First of all, I hate most marketing terms, energetically. Target audience, marketing at or to people. The funnel idea has been a horrible representation of what our goal is.

Do you want to make people go down a funnel? That sounds terrible.

Jesse, you and I know that is the way 80% of businesspeople function.

It’s the short-term wins. You can put a funnel in play and you can see immediate results. You can’t see immediate results of brand play of Hug Marketing and people don’t want to play the long game. They’re so focused on the short game but the long game wins in the end. That’s what we’re trying to play here. I’m guessing that’s a Hug Marketing mindset too.

I’m logical. I know what people mean by a funnel. It’s one step to another. Let’s create a bit of a visual here. We all know what a funnel looks like. Hug Marketing is a series of concentric circles. You’ve got outer rings and then they get smaller and smaller until in the center is the hug. The hug is one step in from the customer. That’s the problem. If a lot of people even go on a journey, they stop acquiring the customer. What I’m focused on is how that customer can become a repeat customer, a source of a referral or an advocate. That’s where the hug comes in. I had a 70% retention rate in my photography business for 35 years. That was the number one metric. That made my life easy.

What did you do?

I talk about these things in the book. There’s a whole chapter on loyalty, referrals and retention. One thing I love as a technique is a presumptive language. To speak to your customers as if. To speak to them from the beginning as if you’re going to see them over and over again. I’ll give you an example. As a photographer, when people would reach out for my services, I would put in the extra effort to go to their homes. I photograph entirely on location. Most often, it was my client’s mansions. There is no better place to photograph than their homes. I would go to their home. I went there to help them prepare, like pick out some clothing, but I was there to walk around the house and help them decide where they’re going to hang the portraits on the walls.

I would go further, I would look for what I call the secondary wall because it’s hard to get people to commit to the primary wall. They might have an idea for a painting or some phenomenally expensive piece of art but the secondary walls were a goldmine. Those are the walls, the hallway walls and their walls going up staircases. I would say to my client, “How do you see this being decorated with portraits over the next ten years?” What did I do? Two things. One, I have ruled out any assumption that they’re going to focus on buying 8x10s for the table.

I am speaking about wall portraits right upfront and introducing that we’re going to be working together for ten years. How do you envision this coming? Now I’ve taken on responsibility for a ten-year project for them. That’s what I mean by presumptive language. I encourage people to look at all the touchpoints from step one, sales meetings, everything. Consider how can you shift your languaging. You’re speaking in as if. You’re not speaking transactional one-off terms.

It's true in business as it is in nature that if something is wrong in your ecosystem, it can kill the whole thing. Click To Tweet

For our team, the Bananas, we have a team and games year-round. With a fan that jumps on the waitlist, has got to get tickets or comes in the office, what would be some presumptive language you would use?

It seems to me you’re doing a lot right. What is your repeat customers or fan rate? How often do people come to games?

Every game sold out and there was a waitlist for tickets in the thousands. We have very little churn. The only churn we have is some people who move out of town. I want to put this in the context of business with presumptive language. Can we even say, “Next time?” What are ways other businesses could use this?

One thing we see people do pretty common is they got a rewards program. Frequent visits have a benefit of some kind. In your case, I would love to see something more personal. Do you have a jumbotron?

No. All areas are 1926 ballpark. There are no sweets. There’s no digital scoreboard. We do the entertainment inside the stadium.

Who doesn’t go to a ballgame and want to end up on the jumbotron? That’s a goal. There could be a way if that were the case. I’m not saying your most frequent returning fan but there’s a tipping point. If the fan comes three times, what’s the tipping point to getting them to come ten times? If you know where they are in the stadium and you are throwing them on the jumbotron, they now feel extra special.

The 2nd and 3rd time, we bring our players into the crowd. We deliver roses, signed bats and balls. There are all those things. When you start seeing a little bit coming around, how do you do that extra step? That’s the Hug Marketing. We put an extra hug in there. Is that what you’re referring to?

Even on a broader love. Going back to the concentric circles. If you look at the outermost circle, I call them lurkers. Particularly, this is important when it comes to social media. As we’re gaining visibility in our businesses, we have people that are lurkers. They’re out there watching us on social media but we have no idea they exist. That’s an important part of social media. When people get discouraged about social media, they don’t feel like it’s working. You don’t know who’s watching you. You don’t know them yet. They’re in that outer ring but they’re important. That’s why you put consistent effort into social media. What happens is they then get curious. That’s the next ring in.

They get curious to know more. In one way or another, they step up. That’s when they start following you on other platforms. They start connecting with not just one platform. They follow you on Instagram, LinkedIn and all the platforms at once. The next circle in is they step forward and engage with you in some way. Now, they’re commenting on your posts or they DM you. There’s an actual course of engagement then they become connected. That’s when they opt into your email lists likely because you’ve given them enough value at that point that they want a deeper connection. At that point, in one way or another they become a customer through direct invitation or the relationship to them keeps deepening to the point that they then consider hiring you for your services or going to your ball game.

The difference between customer to hugger is when you then start catering to that customer and expressing your honor and respect for them being a repeat customer. Any relationally based business, which is true of most self-employed businesses, you want to have a program that’s prepared that people only find out about when they become a customer or they hit a certain level of retention. In my photography business, we had something called prepay offer. That was the hidden secret I revealed to customers after I worked with them once.

I would say, “There’s something in my business that you wouldn’t know about because only my clients know about it. What it is, is that next year in February, you’ll get an email from me inviting you to prepay for your portrait session. It’s going to save you a little money. The most important part is it puts you on the waiting list before anybody else.” As a photographer, I have not so much now but in the days, I had an 8 to 10-week waiting list. This is how I put people in the front of the line. I always put my existing customers ahead of the line.

There was much less availability for new customers. What does that also do? It creates demand because the best words in sales are sold out. That’s what I mean by turning them into huggers. They go from a customer that’s transactional even relationship-based to that customer that when you see them, you’re going to hug them. Back in the day, when we used to be allowed to hug each other, I can’t imagine seeing my best photography clients and not hugging them. It would be unheard of.

The relationship is huge as far as the emotional journey. You’re self-employed, you want to get more control over your business and have a better system. What else comes to play in the business strategies?

You mentioned the emotional journey, I’m going to skip over that and talk about what answers that question. One of the things you can gain the most power of your business is what I refer to as a business model of multiples. Multiple income streams are one way of looking at it. This is where I’ve been doing business differently for decades. As a photographer, I had the most niche business you can imagine. I photograph very wealthy people in a traditional pose in color. It doesn’t get much more niche but that was the ‘80s and ‘90s and people were throwing money on the wall. Anything you did in business stuck like spaghetti. Everything worked.

The internet comes along. The world gets louder. It’s harder now. I’ve been in business long enough to know it’s flat-out harder. It was easy in the ‘80s and ‘90s. There was so much money being thrown around. That’s not the case now. We have to work for that money and I’m all for it. It’s awesome. I was looking for solutions. I’ve reframed the terminology of niche. I like to reframe it to mean it’s not about the one thing you do in the wider audience anymore. It’s about what is the one thing you’re known for which there are multiple audiences and multiple ways you can do it.

BDD 20 | Self-Employed
Self-Employed: Always put your existing customers ahead of the line. There should be less available for new customers. What does that also do? It creates demand.


You’re not all over the place. There’s an area of expertise. My area of expertise is self-employment. There’s not a lot of writing in my audience. There is as far as industry, it’s a huge, massive audience but how do I deliver that message? I’ve got a podcast, self-employed life, I’m putting out a book, I’m doing a summit, I’ve got training programs and I’m launching the self-employed business school. There are multiple mediums that I can deliver my expertise. What that creates in this business model of multiple? I like to describe it as a wall of levers. Imagine, you have a control panel of levers in front of you for which you have control to decide which levers you want to push up and which you want to push down.

A perfect example is during this pandemic. People like you and I, that lever of live speaking got pulled down out of our control. The question is, do you have other levers that can get ramped up? In my case, I looked at my lever, which was already in place and the work I do around LINGO, which is helping people with the brand messaging on their website to make sure they’re attracting your ideal customers. It’s an eight-week program. I crank out. I ramped up that lever so high that it completely sustained my entire year because it’s virtual, it’s a broad audience and it’s exactly what everybody needed then and needs now because there isn’t a business out there that doesn’t need to reconsider their brand message because what you were saying a year ago may not work right now. Are you showing the same level of empathy and understanding? I’ve been working with gyms. They have to say very different things and they talk about sanitation that they’ve never had to talk about before. How are they protecting people coming to their gym?

What are you known for as the case? What are the business models underneath that? If you know me a little bit, how would you look at that? What am I known for and then what would be those businesses and multiples?

To me, you are known for, literally, it sounds cliché but doing business differently. What you’ve done with Savannah Bananas is an expression of that. It’s not your everything. It doesn’t have to be because that’s what makes you a speaker. When you speak on stage, you’re not speaking about Savannah Bananas or even how you built it. You’re talking about how people can take what you’ve learned from doing that and apply it in their own business. Brené Brown, let’s use somebody like that because everybody knows the name. What she is known for is vulnerability. Simon Sinek is another example. They’re known for an area but then they take the lessons from that area and use it in different areas to broaden the possibilities.

Look at what all those different business models are underneath that. For instance, for you, you’ve got speaking, podcast and consulting. Those are your business multiples all under what you’re known for.

You’ve mentioned most of the speaking. I’ve got a specific program which is for brand messaging based on my previous book LINGO. I’m introducing the Small Business Consulting Program, which is specific for self-employed to get their ecosystem in shape. Unfortunately, I have to call it the Small Business Consulting Program because nobody is searching for self-employed. When they get there, they realize that’s very specific for that. I’ve got book royalties. I’ve got a LinkedIn course. One category is called royalties because I get these royalty checks every month. It’s a nice stream of income.

I’ve got a coaching group which again, loyalty. In my coaching group, nobody knows about them unless you’ve become a coaching client. It is a follow-up to working with me in either one-to-one coaching, which is another income stream. Working with me one-to-one, Small Business Consulting Program, the Lingo Branding Program, if I’ve worked with you then you’re invited into the group because the goal of the group is to put together an incredible group of people that help each other stay on track.

The big problem we talked about in the beginning is the self-employed having control. You have so many business multiples. How do you have control over that?

You look at it as a panel of levers. It goes back to what we’re saying about what is your area of expertise. A quote I use all the time and it’s one of my own, it sounds cheesy but it works for this is, “You can wear many hats if you’ll hang it on one hook.” Jesse, to me, you are the guy who represents how to do business differently. How you figured out to do what you did with this ball team is phenomenal. A post you had on Facebook about what your life looks like five years ago to now. I always thought that story was years ago. Imagine what you have done in five years, who the hell doesn’t learn what you have going on in your head to do that.

Every business often thinks their customers prioritize money over time; they don't. Almost everybody prioritizes time over money. Click To Tweet

You know how to turn ideas upside down. That’s so needed. People want that. That’s a speaking platform. That’s your platform. In a way, your experience in Savannah Bananas is like mine as a photographer. If you would ask me twelve years ago why I was on this planet, I would have said to be a photographer. Now I look at it and say, “That has been a hell of a 35-year training ground for me to teach other people what I learned along the way.”

I’m thinking about the business owners who are reading this blog. They might have this business that they’ve been leading and now they’re developing a personal brand. A lot of the self-employed people are becoming personal brands but they have that business as their link that they can help talk about and share. What’s interesting is the more they talk about helping, I’m talking about business, marketing and all that, it helps the main brand as well because people are interested in that. It is almost all fit in that one hook in a way. You talk about a product suite which I loved. Look at what Apple does, how does that fit into there?

Everybody talks about Apple in so many other ways. The thing that is overlooked is the genius of a product suite. People talk about other things that they’ve done very cleverly or their marketing or their brand identity but the fact of the matter is it’s almost subconscious. A lot of people aren’t aware of how hooked you are. It is annoying but their products are integrated. You don’t have much of a choice to switch. The joke is like, “If you buy one Apple device, you’re going to buy all of them because they’re so integrated.” AirDrop is my favorite thing in the world because I have many Mac devices. To be able to AirDrop one thing to another device, it’s unbelievable ease for me.

This is interesting from a business standpoint. Often, we have this product and so on. The synergy from whether a small business or self-employed, Apple done it tremendously but have you seen other examples or even yourself that’s doing this well?

I’ll use my photography business as an example again. I create something unique as a photographer at their photographs but they can’t be replicated by anybody else. Why? It’s because I spent a long time developing a finishing technique. My photographs are framed because they’re large than the wall. They’re framed without glass. I developed a unique finishing technique, it’s a lacquer but with a texture to it. It can’t be replicated. If they hire another photographer, it’s not going to match. To my clientele, affluent people, that would be like putting the wrong upholstery in the living room. They’re not going to do it. They knew that was an emotional hook. Consistency is a huge emotional hook. I created a finish that can’t be replicated.

Hiring another photographer almost makes it impossible to do so. This is very similar to Apple. The products that supported my photographs, the frames, portrait albums, accessories, holiday greeting cards and things that came with it were all custom-made. I locked them in because if they want their frames to coordinate our match, they’re my custom designs. I work with a custom frame maker to make them. They can’t be replicated. It’s customization, for one. The other way I look at it and I talk about this in the book is a step up, step down business model. This applies more to my coaching practice. I mentioned my coaching group. I coach a group as a step down because what a lot of businesses focused on is getting their customers always to step up. They come in at one level and you upsell them.

I look at it more like a great meal. You go for a great meal. There are 3 or 4 courses. You’ve got an appetizer to start with, a main course and dessert. Depending on how fancy you’re going, there might be a couple of other courses in there even the after-dinner drink. There’s an up and down to the experience. The peak being your main entree. That’s what I create as a business model in the book. It’s a step-up step business model knowing at what level your customers are going to come in. It doesn’t mean they come in at the lowest level. I’m not necessarily a proponent of bringing everybody in at the $47 level and then upselling them.

They might come in. Most of my clients come in mid-level. I have less expensive products but that’s not my goal. I have videos and things you can buy but I like them to come in through my programs which are more programmatic. The Lingo branding and small business consulting. They come in mid-level and then we’ve worked at it for 2 or 3 months then they might step up to my main meal, which is one-to-one coaching for minimally six months. Once we’ve worked together, either one-to-one or any of my two coaching programs then they’re invited into my coaching group, which is a step-down.

It’s rather inexpensive but what it does is keeps us in a relationship. It’s a product. You’re step up, step down and your services can be connected together in a way that people are staying in this flow with you over the long haul. They might stay in my group long. Many of my clients have. They stayed in the group long enough to circle back around to saying, “I want to go back to one-to-one coaching. I need more support.”

What’s interesting is bringing it all back to the self-employed life. It’s having synergy between everything. You always have the opportunity to hug them, to be around them and keep them from one thing to the other where we’re racing a battling churn. You’re battling the opportunity of people leaving which you are obviously in the photography business. Is that the big thing from a business strategy to think about? I’m trying to think of the main thing from your business strategy that we should take out of this.

To me, the main thing is, regardless of what your business is, it set up the environment. One of the components that we haven’t touched on is personal development. The reason I focus so much on that is that I live by a quote by Jim Rohn. It’s repeated in this book 6 or 7 times. The quote is, “Your level of success will rarely exceed your level of personal development.” I live by that. I always have. I look at it as capacity. When you increase the capacity of your abilities, your skills and you’ve unblocked your own mindsets, all of that, as part of personal development, it’s part of increasing your capacity. It’s like opening up air and raising the ceiling.

When you do, the success you’re seeking will automatically come in and fill in that space. If you’re limited by your thoughts and your systems to get practical like one thing I point out in the book, a lot of businesses have systems in place. Their CRM and email marketing have systems in their business for the business they currently have. When you should have systems in your business for the business that you’re going to have, the ceiling has to be higher than your current business because if you constantly keep your personal ceiling as well as the ceilings of your systems in your business, if you constantly keep it higher than your current level of success, that space can’t help but be filled.

I love this increased capacity conversation because capacity is something that limits us in so many ways. You think about capacity, the business capacity and the mind capacity of everything you’re working with. There were three questions you should ask to help with the personal development in the book.

BDD 20 | Self-Employed
Self-Employed: When you increase the capacity of your abilities, it’s like opening up air or raising the ceiling. When you do, the success you’re seeking will automatically come in and fill in that space.


The starting point is people want to make a change. That brings up the question, “How do you get people to make a change?” I’ve been looking at the nature of motivation for years to figure out how to help people because I look at myself, I look at other people, it’s not easy to motivate people to stick with something. What’s the difference? The fundamental question I work with my clients and help them get clarity on is not what you want to go towards but to start with what is it that you want to get away from. The problem is most people haven’t grown to hate what they want to get away from enough to do something about it.

It’s the proverbial rock bottom when it comes to addiction issues. Nobody overcomes whatever they’re addicted to whether it’s a substance or your limited beliefs. They’re stuck in a cycle of believing until they realize they want to get away from it so bad that the results of that, whatever is holding them back, are bigger than where they want to go. I start with that. I make it clear. The simple one is money. How often I work? People are like, “What are you tired of?” “I’m tired of working hard and not having as much money as I want.” That’s something worth being sick of. If you’re sick of it, are you ready to do something about it because that’s when we start the real work?

I’ll get personal here with you. It was interesting when you talk about that with even money. I started as an unpaid intern. My wife, Emily, started as an unpaid intern. It’s her first full-time job in the business. She made $19,000. I was paid $27,000 as a general manager running a team. Going into a baseball business in the industry, we know that the salary cap, like what people pay is so low. The idea of paying me or Emily almost makes us sick to our stomach because we know of the industry and it’s a capacity issue. Speaking of Emily, she does Airbnbs. We do all these other things because in the business, we know the way it is. That’s interesting to get over that because of the way you’ve seen it before. I’m intrigued by that because you think about what you’re teaching and the self-employed life. We’re used to how we grew up in this thinking. If we feel like making a lot of money is, we don’t feel we deserve it, we don’t feel right to it then good luck trying to make it happen.

I worked with a coach and client a while back that had done incredible things to improve his life from which he came from. He had considerable success. I only knew him at that level. He had a big public image and I knew him by the appearance of being very successful and the way he lived now and he was broke. It was that weird dynamic. You have a massive platform, tons of followers, have written a couple of books and you’re broke. I don’t fault anybody for that because I don’t hold back. We’re all in process of dealing with the same thing we’re helping other people overcome.

It’s almost always the case. Personally, I’ve had so much relationship therapy in my life. I’m more apt to take advice from somebody who has also struggled in relationships. I don’t want a relationship therapist who’s never been divorced. I want to know what you’ve been through because there are more lessons there. I don’t see it as imposter syndrome and I don’t see it as somebody being disingenuous or inauthentic. He’s a very authentic guy. The problem was he wasn’t shifting his mindset. In subtle ways, I was starting to realize that where he came from was different than how he’s currently living.

I said to him, “Have you, by far, exceeded financially in your childhood, your siblings and your parents?” He goes, “Yes. By a long shot.” That’s hard. Jesse, it’s been my case as well, so I got it. I said to him, “The problem is, no matter how successful you come, your mindset around money is still in the hood.” That’s where he was stuck at. It was a hard thing to say to somebody that changed his life because he realized that no matter how much money he made and how successful he’s going to be, he was going to get rid of it because he was so uncomfortable feeling “better than” where he came from. He had to let that go in order to move forward.

If you constantly keep your personal ceiling higher than your current level of success, that space can't help but be filled. Click To Tweet

Have you seen The Notebook?

A long time ago.

There is this scene that I shared on LinkedIn and it got more traction than I could’ve imagined. it’s the main characters after they were in the water, they were in the boat and it’s pouring rain. He’s like, “I wrote you this many times.” He holds her and he’s like, “What do you want?” He keeps saying it to her because she doesn’t know if she wants him or the other guy. He keeps yelling, “What do you want?” She couldn’t the answer. I think about so many people right now. We don’t have defined clearly what we want. I’m sure that’s a big issue and challenge. You’ve been working on this self-employed life and teaching this. It’s understanding that capacity. What those negative things are influencing you? What are those business strategies? You don’t know what you want. I love the question you said, “What are you known for?” I feel like that’s the number one thing we got to figure out because maybe you don’t want a business of multiples or you want to have one little thing that you do.

Initially, I started the other question which is, “What do you not want anymore?” That’s were like, “What do you want to get away from?” To me, I start with, what is it that you want to get away from? I’m like, “You never want to see it again.” It could be I never want to get away from feeling like the shoe is going to drop, I want to get away from not having money to meet my bills or I want to get away from working 24/7and not being there for my family.

That’s a different strategy because sometimes, it may be easier. We ask everyone on our team who should not work for our company. We interviewed them and we show it. We write down who should not be. We are clear on the people that don’t fit.

I wound up studying this in such an esoteric way because the big question is, “What creates motivation? Is it the push or the pull?” I started looking at that. If you literally Google or do some research, there’s no definitive answer. One of the scenarios is if your car runs out of gas, do you pull it or you push it? You push it. I’m a serious sea kayaker. My partner and I will kayak for 4 or 5 hours on a Saturday and Sunday. I’m the front guy even though I should be the back guy because I weigh more than him but I’m in the front because I did yoga for so many years.

I can sit with my legs crossed and he can’t, so I take the front. This is a sea kayak. I say that because we’re dealing with current and sometimes, it’s extremely rough. This is not a placid pond. What I’ve noticed is that I can stop paddling and we continue to move forward at the same speed in a way. If he stops paddling, we slow right down. It is much harder. The point is I’m pulling. That’s hard. The metaphor is I’m pulling all the weight behind me just like we do in life when we’re dragging the old crap behind us. We haven’t been done with it in order to move forward. Pulling as hard as I decided that what I needed to demonstrate here is what the route of motivation was helping people learn.

Initially, you’ve got to take a push. When a swimmer dives into a pool, he pushes off the edge to get away from that edge. That’s the beginning of motivation. It’s not the dangling carrot of what we want to go towards yet. First, you have to start with what is it that you want to get away from and own it. Jesse, here’s the most optimistic thing we can say in this conversation. I tend to work with people that are of some age. I don’t work with a lot of twenty-year-olds. I’m working with people that have some years behind them and many times, they have many years in business behind them. That’s my sweet spot. At least a few years in business.

What has always amazed me is, if you get this stuff, your life can change so quickly. This is not long-term therapy. It is amazing to me to see the light bulb go off. Like the gentleman who speak with me before, when he understood that mindset was keeping him and he was uncomfortable with being more than his family as he saw it, once he got that, it changes. That’s the most optimistic thing I can say. There’s truth to the old adage that life can turn on a dime. If you have a good awareness led by a trained and appropriate coach, it could be life-changing instantaneously and now you’re rocking and moving.

There’s a lot I want to learn. I even wrote down the daily habits. I love the What’s Going Write Journal, the Growth Jet Lag. Can you give me a little bit about that before you finish up? I want to go through all of those?

The Growth Jet Lag is such an important thing to point out because it’s like a forewarning because the truth matter is a lag of time from when you’ve made changes in your life and the universe catches up to you, whatever the universe means to you. You can even look at it specifically. If you break somebody’s trust, you’re not going to get that back instantaneously and that led me to the customer. Let’s say in an intimate relationship. If you break your wife’s trust, you’re not getting it back really quick. You can take all the trustworthy actions but there’s a lag of time before you earn that back. That’s the way it is in business too. It’s the way it is in personal growth and in business changes.

I could work with my clients as I do. I work with my clients, I dive into the mentality of their customers, I help them rebrand and create incredible brand messaging. They stand there with amazing pride as they know it. They have finally got it clear. The world will know exactly what they do and who they can help, it’s perfect. I have emails pouring in. I’m like, “It’s because the world hasn’t caught up yet. You just put it out there.” I point that out as a Growth Jet Lag because there’s always a period of time from when you make changes into those key changes catch up like, “Here’s the thing. This is where come back to the daily habits you mentioned.” This is completely unscientific. I couldn’t find any science to back me up on this.

In observation, I have seen that there is a correlation between how committed you are to consistent daily habits and mindsets and how long that growth jet lag is. If you’re lazy in your effort, you’re not going to see the results for a much longer period of time. That’s why I have the sustainability group because once I’ve made the changes, I now want people to stay consistent in their daily habits, their practices and their mindsets and not drifting back to inner critics and things that hold them back. We need to stay away from them so that the universe and the world around you even your market can catch up.

I started posting every day on LinkedIn a few years ago. No likes, no comments, nothing going on for the first few months. Few speaking appearances but I kept staying to it. Monday through Saturday and I took Sundays off and it all started coming. It took a year until it started happening but I was consistent creating over-consuming and putting yourself out there. That was very good.

One of the hardest things for most business owners to do is to say that consistently because we like the applause. We need the wins. It’s hard to keep at it. I commend you for that.

You got to keep coming back. I share it with almost every keynote. There’s one Major League player, he has more hits than anyone else that ever played the game. Pete Rose, 4,192 hits. He has 14,000 at-bats, Jeffrey. He has 2,000 more bats than anyone that ever played the game. He has more hits. How do you keep coming to bat at that?

I’ll be honest with you. I love you but in sports, I know nothing.

BDD 20 | Self-Employed
Self-Employed: There’s truth to the old adage that life can turn on a dime. If you have a good awareness led by a trained and appropriate coach, it could be life-changing instantaneously.


I am not into baseball as much as I used to but I looked it up.

I’ll use metaphors though. I said to somebody that I’m taking so many swings at the fence right now because I’ve got many things going on. I’m like, “I’m going to have more misses. I’m not taking a lot of swings right now to get this book out there in the world.” It’s knowing that ahead of time helps.

No one talks about the Amazon phone and it was a $200 million mistake.

I forgot about that.

We don’t talk about it. It’s a huge swing and a miss and that’s the mindset.

Google Glasses for that matter too.

All of those. There are so many. Jeff Bezos said, “Our success is a direct function of how many experiments we do per year, per month, per week, per day.”

I feel bad for Mr. Segue. He didn’t get to say that. Now, we’ve got scooters in every city running all over the place. He was onto it a long time ago.

As a business of multiple, he had something going on.

If he didn’t go off the cliff, he made it better long enough.

He’s probably okay. A few quick rapid-fire in marketing minute. What’s the best thing you’ve done to grow your brand?

This has been a huge step for me. It’s narrowing down. I used to narrow it down to self-employed. I used to think I was for entrepreneurs and then realizing that is a big pool. A lot of people plus swimming in that pool. Nobody is talking to the self-employed. That has been the biggest move I’ve ever done and has given me an incredible brand identity. I want to be synonymous. Simon Sinek’s Why. I want to be Jeffrey Shaw Self-employed. I’m creating that synonymous feeling.

It goes back to that question that you talked about, “What are you known for?” That’s whether it’s an individual or your business. We’re very clear with our business. It’s we make baseball fun. It’s a circus and a baseball game, we’ll break out. People think more of it as a circus and a baseball game. For me, it’s the yellow tux, it’s standing out and it’s being different. This is what we’re starting to be known for a little bit. That’s pivoting. We name our company Fans First Entertainment. Fans first is everything that we do. I’d love to know from you and whether this goes into also self-employed life but something that you have done that was fans first either in photography, with your books or you’re speaking some real special moment that you went the extra mile to create something special for your customer.

I’ll bring that back to my photography business details. My whole goal was to step ahead of them. One of the things that caught on and those are the best things. Jay Baer has what we call Talk Triggers. I remember asking him on these Talk Triggers like the chocolate chip cookies with Doubletree, are they intentional or accidental? Most often, they’re almost accidental. You put something out there and you realize people. For me, in my photography business, we would produce these very expensive custom design holiday cards. They’re $10 a card. My clients would buy 1,000 cards because they’re CEO. They know a lot of people, so they’ll spend $10,000 on their Christmas cards.

We would give them a $2.50 pen where the color of the pen is as close as possible to match the ink color of the return address on the envelope. Whoever was addressing the envelope because they’re going to be hand address and they were hiring somebody to do it. When they were hand addressed, it would match the return address. You would think I gave them the most expensive thing in the world, especially the first time they got that pen. It was the detail. It was such a step of them. They were like, “You not only are giving us these cards.” I gave them one pen per 100 cards because I don’t want them to run out of ink. That was mind-blowing to people.

It was so put them first because it was a deep understanding of how particular they are. I know that there’s no way they’re going to mismatch that. What’s going to happen is they’re going to send a nanny or somebody in the house or they themselves are going to be running all over the place trying to find a matching pen. What I did is to save them time. When they ordered their greeting cards, we also showed them with the US postal service was offering for stamps that year. They would pick the stamp that was appropriate for their family and friends. We would order the stamps. We didn’t put them in the envelope but when they got their cards, they already had their thousand stamps. Why? Nobody has to go to the post office. I put their life first. I put how they live first. I was so aware. Mind you and you this, I think about I grew up in lower middle class. I had to learn this.

It’s also known and everyone to an extent once time back. There’s some reason they want time. They want their life back. If you can be more convenient to make it easier for them, you win.

When somebody asks you what you do, say you’re a self-employed business owner. Be proud. Own that badge with honor. Click To Tweet

In the book, I talk about referred to as frictionless. Somehow, as businesses, we often think our customers prioritize money over time. They don’t. Almost everybody prioritizes time over money.

They’ll pay more money for time.

I used to joke about it because as a photographer, my portrait sessions used to be three hours long because that’s how people saw value in having a lot of my time. In later years, they would pay me more to see me less. I didn’t take it personally. It’s how they lived. Anything you can do to give people back times in businesses, I look at it as frictionless. Go through every touchpoint on how you can take away any friction. Whatever the friction is, make it so easy because we are trained. Uber, Lyft and TaskRabbit, these apps have trained us for frictionless.

That’s my first step in every keynote. I say, “The step to innovation is to eliminate the friction.” You want us to innovate, come up with new ideas. How can you eliminate friction in a better way? That’s what we’ve been trying to do. It’s funny, you mentioned that saving time. When I closed on a house, I challenged the attorney. I said, “What’s the fastest close you’ve ever done in your life?” You usually sit there for an hour and you signed these papers. He goes, “I have twenty minutes.” I go, “Let’s do ten and give it to me inside.” It’s time. Let’s move on. We all want that. Jeffrey, you’re onto the good stuff and important work. Is there any final thought you want to leave?

To be proud. It’s a big part of the book and as we were discussing early on, I want self-employment. What I’m at right now is more of a mission than a book. I’m launching a book as a representation of the mission. After I wrote the book, I also started a Grassroots movement called Voices of the Self-Employed. The sole goal of it right now is to collect emails because I truly believe there’s going to be some legislation opportunities down the road that we’re going to need to pull together some petitions of self-employed business owners in the United States quickly.

I want to be ready to go. When I call the action is available, I want to show up on somebody’s door in Washington DC and say, “I have a petition of 10,000 self-employed business owners. We need this legislation on our behalf.” I started an advocacy group. There’s a lot of mission built into this. A big part of the mission is to be proud of being self-employed. When somebody asks you, “What do you do?” Say, “I’m a self-employed business owner.” Not a freelancer, not a small business, not an entrepreneur. An entrepreneur isn’t even a business model. To me nowadays, people say they’re an entrepreneur. It sounds like, “You don’t have a job right now.” Say, you’re self-employed. That’s what I want to leave people with. Own that badge with honor.

You’re the man for the people. You the man for this proud, it’s key. Jeffrey, it’s a great book. The summary is fascinating. I’m excited to read it and I appreciate you. Thanks for being with us.

Thank you. Glad to be here.

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About Jeffrey Shaw

BDD 20 | Self-Employed

People go into business for themselves to control their destiny. We want the freedom to follow our passion and chart our own course in achieving success and making a positive impact.

What many of us don’t realize when we start out, however, is that being self-employed means entering what can feel like a world of completely uncontrollable circumstances. The demands of self-employment, entrepreneurship, and small business ownership are many, and often bleed over into personal life. Before long, it can feel like the business we wanted to run is running us.

Imagine having the strategies to attract your ideal customers, gain control over the results you want, and manage what you can’t control so it doesn’t derail you.

That’s what I love helping self-employed, small business owners and those looking to go from corporate life to self-employed life to discover and put into action in their lives and businesses.

That’s what has shaped the unique approach I share with audiences and clients. Because let’s face it, there’s no shortage of advice out there about how to grow your business. There’s also no lack of personal development books and programs.

But over my 35+ years of experience being self-employed, what I found is that the capacity for business success is linked to personal growth. So what is needed is not another how-to guide for business, or another self-help book. What we need is a holistic approach that recognizes that our personal development and business growth are part of one connected ecosystem.

Whether I’m on a TEDx stage, delivering a keynote speech to an association live or remotely, consulting with a small business, writing a book, or coaching a self-employed business owner, what I’m really doing is helping people set up the circumstances they need to gain control of their business and achieve sustainable success.

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