How to Build the Confidence You Need to Go After Higher-Paying Markets

Summary: In this week's training episode, coach to freelancers and entrepreneurs, Jenn Lee, provides strategies and tips for building the confidence we need to go after higher-paying markets.

As freelancers, we sometimes put self-imposed limits on how much we should charge and which clients we can pursue.

How can we get past these limits and shift our thinking to overcome fears and recognize the value of our services? In this training episode, Jenn Lee provides strategies and tips for building the confidence we need to go after higher-paying markets.

Jenn is a heavily sought after keynote motivational speaker, trainer and coach who works with entrepreneurs, solopreneurs and small business owners. She's a regular guest on Orlando's (Florida) Fox 35 News and several Orlando-area radio morning shows. She was also recently chosen as a feature speaker for Good Morning America's "Troy Johnson's Spark and Hustle National Hour." You can learn more about her at and on Facebook at

What follows is a condensed transcript of my lively conversation with Jenn. If you prefer to listen to the full audio (30 minutes), you can listen to it or download it here:

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Ed Gandia: As solo professionals, we often place limits on how high we can go in terms of fees and quality of clients. How do you build the confidence to break past these self-imposed limits and go after better clients and higher-paying work?

Jennifer Lee: What I find when I'm working with clients is they always say, "I don't think I can charge that much." Or, "I don't think I'm qualified to call that client." I always throw down the BS card and ask, "Why do you think that?" And sure enough, it's a self-imposed limit. They have some story in their head where they think they need 15 more years of experience before they can ask for a higher rate or call potential clients. And I say the first thing you have to do is detach your personal value from the outcome.

You've got to say to yourself, "This is not about my personal value. My calling, say, GE and GE saying, ‘No, it doesn't seem like a good fit,' doesn't play a role in how I feel about me and my services."

Yes, it might be a disappointment, but you've got to detach. If you can identify a need a potential client has and know you have a service or product that can relieve that pain, I say, "How dare you keep it a secret!" The potential client is struggling, waiting for somebody like you to call, and you're sitting in your office, scared to death, thinking they're going to say no to you?

You need to detach yourself from it and say, "This is a business-to-business relationship. They have a need; I have a service. Let's make it happen." I have a couple exercises I use with my clients that help to highlight this.

Ed Gandia: Yes, please share those with us.

Jennifer Lee: Let's say you're a writer, and one of the clients you want to go after is a medical spa - people who do those Botox injections and high-end facials. You have to ask yourself, what is a client worth to them? On average, in a medical spa, a client is probably worth anywhere from $500-$800. If the service you provide can increase their conversion rate by just one new client a week, that's worth $26,000 to that medical spa over a one-year period.

Heck, cut it in half: one new client every two weeks. If they convert that, that's $13,000 to $26,000 worth of new business every year. So why would you feel guilty charging $750, $1500 or whatever it is? Why would you feel guilty proposing that fee?

If you present it to your prospects like that, they'll get it.

Ed Gandia: That's a great point. I heard something similar at a seminar a long time ago: "Never sell with your wallet." Don't assume you and the prospect are using the same criteria. You have no idea what their budget is. They might be used to paying a heck of a lot more and then you come in with a $1,000 figure when they were expecting somewhere between $5,000 and $10,000. You're going to scare them, right?

Jennifer Lee: Right. They're going to go, "Oh, this person doesn't know what he's doing."

Ed Gandia: Never sell with your wallet.

Jennifer Lee: I love that. And you're right. You should also never sell based on what you think it's worth. If you think, "Well, this is easy; it only takes me 45 minutes to do it, or 25 minutes to do it. I guess I should charge $75 bucks." But that's not the value to the client. The value to the client is that if I get one new client from it, that's worth $1,000 or even $2,000 to me.

Ed Gandia: That's a good way to put it.

Jennifer Lee: Look at it from the clients' perspective. It's not easy for them. That's why they're hiring you.

Ed Gandia: And you made another great point. We always assume, "Well, they don't want to be bothered." As though what we have to offer has nothing to do with what they're trying to accomplish, and that is completely false. If you have a service of value, if you're pretty good at what you do, chances are you can help them. The problem is your self-confidence and your ability to communicate the value to them.

Jennifer Lee: Yes. I was talking to a client yesterday about this very subject and she said, "I just don't want to feel like I'm pushing something on them." I said, "You're making the assumption that they're pushovers. Are you telling me your clients are going to pay for a service they don't see a need for? Are they going to say, ‘Oh, she seems really nice, let's write her a check for $2,000'? Of course not."

They're paying for a service because they have a need. It's our job as freelancers to help potential clients. Tell them, "Look, don't spend money on print marketing if it's not effective. Let me help you write that copy," or "Instead of spending your money on a passive program, let's do something that's more active." It's up to you to understand their needs, their pain points, and how you can relieve them.

If you do that, it doesn't matter how much you charge. What you charge is based on what you need as a business owner. I'm in the business of making Coach Jenn profitable and making my clients profitable. It's a win-win, not a win-lose. I say, "How dare you sit there at home and feel sorry for yourself while you've got a client out there suffering?"

You owe it to the country, Ed! That's how I look at it.

Ed Gandia: I love that! It's your duty. So you said you had another exercise you use with your clients?

Jennifer Lee: There are two more and the next one's really simple. Many of us come from some sort of corporate background. So I ask my clients, "What was your salary?" Then I ask them to add in what their company had to pay in insurance for them and their vacation time. I get them to add in the amount of money the company spent on their desk, electricity, Internet, cell phone, and health package. Add all that up and that's what you were worth to that company before.

So why do think you're only worth one quarter of that now?

Ed Gandia: Great point!

Jennifer Lee: And then the third thing I always ask my clients is to check who they're associating with. If you're hanging with people who have the same kind of self-imposed mental block, it's going to be hard for you to break out of it.

Start associating with people who have a success mindset. Connect with people who think bigger. Who value themselves. Check who you're hanging with because sometimes that has a lot to do with it. It's too easy to fall into, "Oh, the world is only really this big," when in reality it's way bigger.

Ed Gandia: Jenn, I hope everyone walks away with that one. Throughout my career, the quantum leaps I've made have come as a direct result of hanging out with people who thought much bigger than I did. It's contagious. When you start talking with people who think bigger than you do, you automatically start doing it yourself. It becomes the norm. It becomes the expected reality.

Jennifer Lee: Right.

Ed Gandia: And it happened to me just recently. I started a Mastermind Group and in a recent meeting, I told the group about a goal I had. And one of the guys said, "What would it take to double that?" So I told him, and as I'm telling him I'm going, "Oh my gosh, it wouldn't take that much more to double that," and it's become my new reality. Now, it's just a fact of life and I'm thinking along those lines and guess what, it's starting to happen. It's amazing what you can do when you hang out with people like that.

Jennifer Lee: That is so often the case. I don't read any fiction. I only read things based on real-life events, autobiographies and stuff like that because I want to know what makes people different. And every single time, it's that exact same thing you just said. They went from humble beginnings to thinking, "Wait a second, what if I thought bigger, what would happen?" and then they just start making the right decisions.

It's about thinking bigger. You've got to get that self-imposed stuff out of the way and hang with people who can help you. And you can pay it forward later because you can invite other people to come up to your level. And then they'll pay it forward to the next person, and so on.

Ed Gandia: A common obstacle to raising fees or going after higher-caliber clients is the fear of losing the deal or not meeting your income goals. How do you let go of the feeling that you really need a project? Especially if it's a high-end project, and it could really make your year. You're scared of pricing yourself out of it because if you don't get it you won't meet your income goals and everything will go down the toilet. How do you get over that?

Jennifer Lee: You start by putting together a strong game plan. You say, "This is the amount of money I want to make, and here are my three buckets of ways I'm going to make that and one of them is, I'm going to land two big deals."

So now here you are at one of those two big deals and it's part of that game plan. But then you start thinking, "If I lose this deal, I'm not going to make my overall goal," and that's just not the truth. That's coming from a sense of "there are only two deals out there in the whole world," and that's not the case.

So you've got to first off understand: if you lose the deal, you lose the deal. It wasn't the right deal. You may learn from it, going, "Okay, what was that about? Was it pricing?" Sometimes it has nothing to do with pricing; sometimes it's because you didn't show the value of the pricing. It could be that it's out of their budget in general. Go back in and ask questions. But most importantly, have your game plan and focus on your efforts... and not as much on the actual goal of landing the project.

I love to share this story: I'm a huge fan of the University of Alabama's football team. Nick Saban is the Head Coach there, and a couple years ago, they were in the running for the National Championship. A reporter asked him, "Coach Saban, what do you do to keep your guys' eye on the National Championship prize? Do you have a picture in the locker room? Do you talk about it everyday?"

And he's like, "No, I don't. At the beginning of the spring season, I say, ‘Our goal is to win the National Championship.' And then I don't talk about it ever again."

"As a matter of fact, we don't even talk about winning the Southeast Conference. We don't talk about winning individual games. We don't even talk about getting a touchdown. We focus all our efforts on the play, the individual play. And then it's broken down to the individual: what are you doing in this particular play? That's what we focus all our efforts on."

"The National Championship is the prize, but I don't have any control over that. I only have control over the efforts I make along the way. You have to just keep focusing on the plays."

So in pricing yourself, stay true and honest and be confident that you put together a game plan that makes sense and then just go forth. If you lose it, go to the next one.

Ed Gandia: Wow, what a great way to look at it! You're right. We often tie our emotional wellbeing to a specific outcome. But when we tie our emotional wellbeing to effort, we can't lose.

Jennifer Lee: You can't, because in the end that's where your value is. That's what you've got control of. It goes back to looking in the mirror at yourself—because that's who's stopping you, right? No one else is stopping you. There might be circumstances that block you, but when the rubber meets the road, it's the person you're staring at in the mirror. So detach your personal value from it and go forth.

I find that when I haven't won deals, I'm not really all that concerned. I've make six more phone calls since I sent in that proposal, so I've got something else in the pipeline. As long you're working your plan and focusing on your efforts, nothing will ever seem like it's a make-or-break deal.

Ed Gandia: Well, I would add something to that, Jenn, and I preach about this all the time. You cannot stop your marketing. You have to continually do prospecting and it's not because, "Oh, it's the right thing to do; you should do it." It's because when you continually prospect, your pipeline is continually fed. The deal you're quoting doesn't feel like the only deal. You know there's going to be more down the pike.

In other words, you always know that there are lots of people out there, you know your pipeline's being continually fed, so you're not worried about it … and guess what? You act more confident. Many times, it's that confidence that wins you the deal. It's that X-factor, that confidence level when you talk to your prospects. It comes from knowing deep down inside that your emotional wellbeing, your happiness, is not tied to this particular project. I know that I've got some other opportunities in the pipeline."

Jennifer Lee: Opportunities build confidence, no doubt.

Ed Gandia: I have another question for you. Do you think it's better to set incremental goals or should you set goals that really stretch you? I've heard arguments for either side. I'd love to hear your opinion.

Jennifer Lee: Well, I'm not a goal-oriented person, believe it or not. I'm more focused on the plan, the game plan. I practice the efforts. I replace "setting goals" with "do I have specific people I want to pitch my services to?" So you put together a list and you say to yourself, "Boy, that's not really stretching. Is that really my wish list? Why don't I add a few more?"

That way you stretch yourself while also recognizing that you're still dealing with human beings, no matter what size the company. There's a human being at GE who makes decisions and there's a human being at Honeywell who makes decisions. They're all human.

So why am I trying to stay with the smaller company when it's still a human being I'll be dealing with at the bigger company? When you start making calls you realize it's the same pitch, you just have to customize it. It might be harder for me to get to them, but I'm still going to make that phone call to GE or to Honeywell.

Basically, every business has the same need. They either want to make money or save money, period. That's it; it all boils down to that. So I say, don't focus on the goals, focus on whom you want to work with and then stretch it. Make the name a little bit bigger. It's not about stretching you; it's about ramping your services up to a higher level.

Ed Gandia: Well said. It's a slight mindset shift, but it makes all the difference. It goes back to what you talked about earlier, focusing on the plan and the effort and not on specific outcomes.

Jennifer Lee: Yes, and I'm going to share something that might seem like I'm telling you to have an out-of-body experience, but it really does work. When you're going through this process, making that phone call to the bigger client, the one that makes you nervous, sometimes it's okay to give yourself an alter ego, like a pseudo ego.

I had a client who's name is Wendy. When it came to doing something difficult like these calls, she was like, "I can't do it, but my sister Barbara would be able to do it." And I said, "Well, why don't you just become Barbara for the day and think like Barbara?" And so whenever she has to do something really difficult—now she's gotten past it—but when she has to do something really difficult, she's like, "Oh yeah, I'm totally Barbara. Barbara's making this phone call, not Wendy."

So just go ahead and create an entire character in your head. Barbara has 27 years of experience. Barbara has done business with bigger boys before. So Barbara's going to make the phone call. Trick yourself.

Ed Gandia: I would write on my white board, "What would Barbara do?"

Jennifer Lee: Yes, what would Barbara do. I wrote a blog post about that. I got a lot of responses. Be Barbara for the day! It's okay.

Ed Gandia: I like that. I think I've tried that before not even knowing that it was a good tactic, and you're right. What would this person do, how would they act, how would they carry themselves? And just thinking like that for a few minutes makes a big difference.

Jennifer Lee: It does. Yeah, it does.
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Ed Gandia: I have one last question for you. One of the things I was taught early on is to never waste a victory. Most freelancers and solopreneurs, when they get a huge win, they stop to celebrate. But that's also when you're at your best. Don't waste that victory. That's when you need to make those phone calls. That's when you need to go after the prospect that scares you. How can you use successes to give you the confidence you need to go after the better clients, the higher-paying projects?

Jennifer Lee: I come from the same background: close the deal, make a call. If you close the deal, you immediately make a phone call, and it's not to your mom to say, "I closed the deal." You make a phone call to the client you've been trying to get a hold of. Your voice, everything about your whole being changes. So close the deal, make a phone call immediately. That's tip number one.

Tip number two is to leverage the fact that you closed the deal. I always like to grab testimonials from my clients and make sure I've got them on my website. That helps the person who's looking at me go, "Oh, you know what, she's worked with Toys "R" Us in the past; that's a pretty big company. I have confidence in her because Toys "R" Us had confidence in them."

On Facebook, I post if I've just closed a big deal or worked with someone. I say, "The American Cancer Society just asked me to be the keynote; what an amazing honor." My phone always rings when I do something like that.

When you're in a proposal situation, there's nothing wrong with name-dropping if you've had success with a business that's similar to the business you're speaking to. "You know what, your concern and need is very similar to the one my client had when I was working for Securian Financial," and then you repeat whatever that concern or need was, "and we were able to resolve it by doing this." That helps the client see you in the light of their world. It also reminds you that you've done this before.

And if you do some other things a little more consistently, you will win and it will keep your confidence level going. You won't have to do some of the things we talked about earlier. You'll just be doing your thing. "They've got a pain; I've got a service that will relieve that pain, let's make it happen."

Once you figure out what you want and are committed to making it happen, the rest is just logistics.

Your Turn

We'd love to hear from you guys! What strategies, tricks and techniques have enabled you to boost your self confidence and go after clients and opportunities that may have once seemed out of reach?

Let us know in the comments area below. Let's get a good conversation going!