Perhaps my favorite part of joining CloudPeeps has been becoming an advocate and activist for the freelance movement. I feel a special connection with those who reject the confines of a 9-to-5 life and who are willing to risk the safety of a steady paycheck to pursue their passions.

One of my main goals every day is to find job opportunities for Peeps — to help empower them to live their dream life and advance their careers.

Finding clients is only half the battle though. Freelancers face stiff competition. They need to be able to convert potential customers into paying clients and steady income.

Having opened a successful freelance business myself in January 2015, and now as head of customer success at CloudPeeps, I’d love to share some helpful tips for winning and keeping business as a freelancer.

1) Be flexible with your rates

To have a successful freelance business, you have to know your economic worth. Too often, I see freelancers defining their worth by what they believe to be the market rate, turning down “low-paying” work without another job lined up.

“I don’t get out of bed for less than $10,000 a day,” said no freelancer ever.
“I don’t get out of bed for less than $10,000 a day,” said no freelancer ever.

When your survival depends on the success of your freelance business, your rates should fluctuate with your availability. When I first opened my freelance business, I charged the first customer I ever had $50 for over an hour’s worth of work (a ridiculously low rate for a lawyer). She has since referred me to over a dozen clients, all at much higher rates.

I charged the second customer I ever had, CloudPeeps, a rate that was about a third of what I was charging clients in private practice, and I was happy for the business. Not only did this result in continuing work for CloudPeeps, it ultimately resulted in my current full-time role. Had I not been flexible with my rates, insisting on only charging what I believed the market rate to be, I would have missed out on so many opportunities.

As your availability decreases, your rate should increase. This doesn’t mean charging current customers more (at least, initially). It means being more selective with new work you take on, and even turning down work if it means you can make more money elsewhere.

2) Focus on long-term relationships over short-term gains

When searching for work, whenever possible, focus your efforts on customers who will have ongoing work for you rather than one-off projects. Even if the rate is lower for the ongoing work, it’s well worth it to have a steady stream of revenue.

When you do land a one-off project, focus on turning that into more work. The major way to accomplish this to do an amazing job. Make them either want to hire you again or to refer you to someone else. Your clients’ referrals almost always have a higher lifetime value, and can become your major source of revenue.

My next point is another major way to turn a one-time client into a long-term customer.

3) Treat clients like people

In the first five minutes of every phone call (or first sentence or two of an e-mail) with a potential, current, or previous client, I almost never discuss business. Instead, I’m more concerned with establishing and maintaining a personal connection. I ask how they’re doing, follow up on their latest trip or tell them a silly story about my day to make them laugh.

Though my reasons are entirely altruistic, this type of relationship building can do wonders in gaining and keeping business. Generally, people like working with people they like. And when establishing a relationship with a client, you want to make sure they like you.

As an example, in my freelance business as an employment lawyer, I often pursue work with individuals who have been fired or accepted a new job. My first comment to them is always a form of, “Congratulations on your new job! It sounds like an amazing opportunity!” or, “I’m sorry to hear about your job loss – I know how rough it can be.”

With the first sentence or two, I accomplished two important goals:

1)  I let the client know that I read (and understand) their current situation and need

2)  I portrayed myself in a friendly, likeable manner


Treating clients like people won’t just help you win and maintain business, it’s also the right thing to do.

4) Learn about your clients

As the relationship progresses, try to learn as much as you can about your clients, both professionally and personally. When are they planning to launch? What products do they have? What are their hobbies? This information can be crucial in maintaining your business with them.  

A good habit is to occasionally search for news about your client (or their industry) online.  The better understanding you have of the landscape your client is operating in, and who they are as a person, will help you maintain a relationship. It’s not creepy to set up Google Alerts for them – do it!

5) Send check-in emails

When you see that your client was recently featured in TechCrunch, message them! Even if it’s not about business, messaging a client – and particularly a previous client – with a quick message will keep you at the top of their mind.

A personal experience from this: When CloudPeeps was my customer, I would occasionally email Kate tips about flights to Australia (where she’s from) from San Francisco (where she lives now). Kate has since said this made me stand out among her other lawyers and helped lead to our ongoing, and now full-time, relationship.

6) Be loyal

It was CloudPeeps’ support of my business that made me believe that I could be successful in freelancing. Though I originally helped Kate with one assignment, we went on to work on many jobs together. No matter how busy I was, or how much I was able to charge others, I always kept my rate the same for CloudPeeps and never turned down an assignment. The reason: loyalty.

When you have a customer who believes in you, you should do whatever you can to hold onto them.

An artist’s rendition of Josh telling Kate that he’ll never let go of her business.
An artist’s rendition of Josh telling Kate that he’ll never let go of her business.

7) Admit when you can’t do something

Picture this: You’ve found an amazing client who pays well and you get an email at 11pm from them with the subject, “Have some more work for you!” You put down your night cheese and open the email only to find out that your client is looking for something outside of your skillset.

A few thoughts jump into your head:

  • “If I tell my client that I can’t do this work, will they ever use me again?”
  • “I don’t have a background in this, but maybe I can learn how to do it?”
  • “Where did I put my night cheese?”

While it’s always risky to pass off your clients to other freelancers, it’s better than giving them subpar work, and frankly much better than you learning on their dime. In these situations, tell your client that the area is outside of your expertise, let them know if you think you will be able to nevertheless take on the work, and let them know if they’d prefer to work with someone else, you’re happy to give a referral. They’ll appreciate your honesty and may end up using you for the work anyway, even if it’s your first time working in that area.

Liz Lemon, eating your night cheese (you’re never getting it back).
Liz Lemon, eating your night cheese (you’re never getting it back).

Parting thoughts

Some of these tips may seem like common sense – that’s a good thing, they should come naturally. It’s important to follow your gut and use your intuition. A safe guide for communicating with clients is asking yourself how you’d like to be treated. Start there, follow the tips above, and you’ll be on your way to having a successful freelance career!

Have questions? Leave them in the comments below!