How Being a Freelancer Is Like Dating (and Lessons Learned)

Being a freelancer has changed, just like dating. You can't just buy your date dinner and suddenly become the most interesting person they've ever met. When you're "dating" too many clients, what can you do to stand out?

You only have one shot. No pressure.

The first hours are stressful. The same is true in freelancing. You know the hours I'm talking about. You're with your date and you have no idea what to say. They're looking at their phone, and you're losing your train of thought. You've been in that hour where you're shoveling food into your mouth while struggling to find common ground. The same goes for freelance clients (minus the food-shoveling part). You sent them a great proposal but never heard back. The first hours are scary. On a first date, you only have one chance to make a first impression. If you don't get it right, you lose. Here's an example: You were cooking steak for this girl, you dropped one on the floor, and you were instantly embarrassed. First impression = dead. (Luckily, the girl laughed and joked that she likes her steak floor-style.) But guess what? In freelancing, there's no room for steak on the floor! At the start, you either get something wrong and don't get a response to your proposal, or you do get the proposal accepted. The problem is that most freelancers drop the steak on the floor and don't even know it. What are they doing wrong? They treat the client transactionally. The same applies to the first hours. After the salad course, you don't want to ask your date back to your place. It would make them feel cheap. Make sure your client doesn't feel cheap, and learn how to start a conversation.

How do you play the freelance dating game?

Don't have the skill to chat with a potential client? Let's learn how mastering the "Conversation Economy" can get you offered the gig. Imagine this. You just walked out of a lunch meeting you'd been worried about for a week. You wrote a great proposal, researched the company, and when you showed up, you were completely relaxed because you "owned it." The meal was great, and you ate your whole lunch BUT you talked about the project. When you go to take the next step, the client gives you a nod and says, "We'll send the payment after we get the contract." They loved you, and you nailed it! Being successful is really that easy. Once you're a master, even floor-steak situations can turn out in your favor. Three ways to start a conversation and write proposals that get you hired:

1. Open with your client's name

You wouldn't start a first date without knowing your partner's name. (Actually, some have done it to win a bet. A terrible idea.) Use the client's name in your proposal to grab their attention and show them you're not sending a canned template proposal. If you send a canned template proposal, that's silly. Tip: Using a client's name in a proposal removes the psychological barriers to being hired by humanizing you. The more human you appear, the more you stand out, which makes you more interesting to talk to.

2. Write normally

Have you ever been to a conversation where you knew someone was trying to sound smart? It would be awkward. The same goes for freelancers. The trendy language or jargon used in the business world is the strange white noise of the freelance world. Avoid them. Don't be white noise. Here's a classic situation I always see when coaching freelancers. You'll want to sound smart and say things like "I'll optimize click-through conversion." Stop! If you want clients to talk to you, try "I'll find more readers to join your mailing list." People don't always speak technical language. They don't talk about KPIs or CTAs or SEO every day. People speak plainly and respond best when spoken to plainly. When you communicate simply, clients don't have to translate your ideas. Your clients will be more comfortable and find it easier to focus on the conversation. Speaking normally humanizes you and helps you stand out from the crowd.

3. Validate your client's needs

The worst first dates happen when you dominate the conversation, and the same goes for freelance conversations. Successful freelancers don't talk about themselves. They talk about what a client needs and how they can deliver those results to them. Here's how you can put your clients first: Anticipate a client's needs and offer them advice. Most freelancers protect their ideas. They're afraid of clients sharing their suggestions with a cheaper freelancer. They probably won't win most of the time (and if they do, you don't want them as a client). Use your free ideas as currency to generate big returns. Provide relevant references for your client. When they need a landing page, don't waste a client's time sharing your favorite SEO project. Most freelancers copy and paste their favorite projects into proposals, even if it has nothing to do with the client's project. Relevant examples show that you took the time to craft your response. Pro Tip: If you don't have a reference that matches your client's needs, include one anyway. Explain how the strategy that made the project successful would apply to their project. Making a lateral comparison creates subtle social proof that you not only know a project but also know how to succeed.

4. Remind them they started the contact

Have you ever had a great date and then forgotten to follow up just because you got busy? It's awful. The same thing happens in the freelance world. Don't forget to ask for the follow-up! Copywriters always do this with CTAs. A CTA is how you guide the client to the next step. The best CTAs work because they position the client to want to take the next step. Think about the best time you went out. You're having a blast and you realize you want to see this person again. All you need to say is, "Let's do this again." Here's how it's done. Have you ever started planning your second date in the middle of your first date? Usually you talk about something you enjoy, and your date says they've never visited / eaten / seen it before. The next thing you know, you're signing up for a steak cooking class. The same thing applies to freelancing. You provide follow-up value to encourage the client to want to learn more. Example: "I have two suggestions to get your project started right away. If you call me, I can share them with you." It's straight and to the point. The client knows they want to reach out to learn more. You've started the conversation!

Goodnight kiss

We're entering the Conversation Economy. Freelancers who develop social skills will out-experience, out-work, and out-earn other freelancers. That second date can be yours through real, authentic conversations. Do you have questions about how to start the conversation in your freelance career? Ask them in the comments below.