How to make selling freelance design less stressful and more fun

By Rob Williams

One of my favorite pieces of advice from the king of client work, David Ogilvy, is: “you should approach [finding clients] with light-hearted gusto”. I like this quote because it’s so obvious, yet seems alien. Most people fear selling and find it stressful. But why? It’s because we wait to do it until our back is against the wall. Most freelancers, for example, wait until they’re in a dry spell to look for more work. 

After a few of these cycles, we associate sales with the most stressful moments in our life. And that’s not the only problem. Most freelancers sell without a clear purpose, which also feels horrible. It means you don’t know what to say or what your clients want. These two factors come together to make sales seem like a dirty word. Let’s change that. Let’s make selling your service fun. Here’s how:

  1. Try looking for clients when you’re flush with work.
    Contrary to popular belief, dry spells aren’t just a part of freelancing. They happen as a result of not aggressively looking for work when you ALREADY HAVE work. Looking for work when your schedule is full will not only make you less stressed about winning a job, you’ll also negotiate from a position of power. Tell clients as quickly as possible that you’re booking weeks or months out. First off because it’s true, but secondly because it tells them you’re in demand.
  2. Tell prospects what you don’t do.
    Antique dealers draw your attention to flaws in their furniture because they know it will gain your trust. You should do the same. Tell clients what you don’t do before you go into what you do. This will make you more credible when you tell them about your strongest points.
  3. Make clients say you’re going to make them a lot of money.
    You may not have realized this but your your work will make clients more money than they pay you. It’s an investment. One of your goals in the courting process should be to get clients to admit this openly. If they can’t talk about how your service will pay off they’re not ready to pay you money.
  4. Make the call quickly. 
    Fear and anxiety sets in when you take too long to make a decision. So set yourself up to make the right decisions quickly. Ask clients the questions you need to know beforehand. Don’t live and die by each client you go after. Not everyone is right for you and no matter what you do you’ll never land every client. Use these facts to lessen the pressure and qualify clients quickly.
  5. Write your way to the close.
    If you’re forcing yourself to close every client on a call, you’re putting too much pressure on yourself. Instead focus on making your writing so good that it puts you in the best position possible. This means your emails, your website, and your proposals should impress the client so much that they’re ready to hire you before they get on a call. That way clients will be ready to jump into action when you make a compelling offer.
  6. Expose the money.
    Don’t hide behind a cloudy sales process. Instead expose each step a client goes through to pay you money. Your sales funnel should be orchestrated and finely tuned. Think deeply about how your money gets to you every single day. Put it in front of you often.
  7. Provide a contact form that’s asks all the right questions.
    This makes it easier for clients to reach out. It will also make you look more professional because it shows you have a firm grasp of the process. This puts clients at ease because it paints you as a trustworthy professional.
  8. Listen more than you talk in your meetings.
    It’s not up to you “win a client over.” Instead let the client do most of the talking. This should be welcome advice for introverts. Just listen. Be picky. Record the call and review it later. Try to dig deep before making recommendations.
  9. Don’t rush it.
    Make sure you have a solid understanding of what the client’s problem is before you try to solve it. This is the biggest mistake I see inexperienced freelancers make. Don’t try to sell your service in the first meeting or email. It’s impossible to do that anyway. You need to build up a relationship and a understanding of the problem at hand.
  10. Cut your proposals down to one page.
    Not only will they take less time, they’ll make your proposals more likely to get accepted. So give it to them straight and remember: your proposal shouldn’t try to sell your service it should be a formality — simply putting ink to paper about what is expected.
  11. Skip the super long email and present your solutions with a video.
    When you send a proposal over email, you typically won’t hear back for a few days. Emails take a long time to digest and they probably don’t get read fully anyway. Instead record a quick video that will explain things more naturally.
  12. Use pre-suasion when you give your price.
    Try this next time you present your price to a client. Right before you reveal your amount, say “well, as you may know I’m not going to be able to charge you a million dollars for this.” This will release some pressure and the client will probably laugh. Below the surface, however, your number will seem a lot smaller in comparison. Studies show it works.
  13. Enforce a no-negativity rule. 
    It’s easy to talk crap about clients, but resist this. Don’t give yourself a hard time or feel down about your abilities as a salesman either. In fact you should seek out the negativity in your sales process and destroy it. Force yourself to become 100% positive about your sales and you’ll be amazed by how much work you land — and surprisingly, how much enjoyment you get from finding it.

About Rob Williams...

I run Folyo which helps freelance designers find the work they were meant to do. I also host Freelance a podcast about how to be more effective at independent work featuring remote companies like Disney, Basecamp, YNAB, ConvertKit and more.