What building a pipeline actually looks like
How I find freelance clients without starting over from scratch every month.
When I started freelancing in 2016, all my early clients came from sending job proposals on Upwork. And honestly, I have no regrets about that strategy. People like to hate on Upwork, but I found some good clients there and it allowed me to get the reps in while I proved to clients (and to myself) that I could do this work.
But by 2018, I was starting to feel pretty drained and like my business wasn’t very sustainable. At the beginning of the month, I would send a bunch of proposals and work as fast as I could to complete that work all month. Then the following month, I would have to start over from scratch and would have a mini panic attack wondering how I’d get paid.
Desperate to figure out how I could break free from this cycle, I bought a course from another freelancer I respected, and he gave me a free coaching call. I’ll never forget talking to him on Zoom and hearing him say, “You need to build a pipeline, Jamie.” And I felt so confused about what that even meant, much less how to actually do it.
Today, I think of my freelance pipeline kind of like the faucet on my kitchen sink — I can turn the volume up when I need more clients, or turn the pressure down when I’m over-extended. But for me, the goal is to never turn it off.
The two buckets of pipeline maintenance
Every pipeline-building activity I do falls into one of two buckets: maintaining current client relationships and building new relationships. Here’s what that looks like in my business.
Maintaining current client relationships
Keeping the faucet on doesn’t just mean finding new clients — it also involves protecting the work you already have. For me, that looks like reaching out to see if my current clients need any additional assignments in the coming weeks or months. I know that sounds obvious, but I’ve noticed that a lot of freelancers wait for their clients to reach out to them, and I never do. I’m always checking in to see what else I can help with.
And because I know it’s easier to get a current client to give me more money than it is to find a new one, I’m also always looking for ways to expand my current relationships. I write for a lot of large companies, and they usually have more content needs than just the one thing I was hired for.
For example, I recently noticed one of my clients has a whole brand studio running sponsored content. So I reached out to that editor and let her know I’ve done similar work before and would love to help out if they ever need it. She may never take me up on my offer, but it shows I’m looking for ways to add more value to her company.
I also look for ways to stay in touch with old clients. The days of staying at one job for 20 years are pretty much over, and people move around a lot, especially in the marketing industry. So if my point of contact leaves their company for a new job, I make sure to keep in touch with that person because there’s a good chance they’ll have a need to hire freelancers in the future.
Another way I build relationships with my clients is by responding to emails quickly. And by quickly, I don’t mean I get back to them within 24 hours — I mean I almost always answer emails within the hour. I know a lot of people will be opposed to this idea and talk about the need to set boundaries with their clients.
But personally, I’ve never had a single client take advantage of this, and my experience is that people appreciate this kind of responsiveness. The other day, I was assigned a $750 rush article, and I can almost guarantee that editor offered it to me because she knew I would get right back to her.
Building new relationships
If I feel like my current workload is getting light, cold emailing is one of the ways I turn up the pressure in my business. But that doesn’t mean I’m over here sending out cold emails every day. I tend to go in phases with cold emailing, and I time them around the natural rhythm of my business. Fall and winter tend to be busier times of year for me. There’s usually a brief holiday lull in December, then January picks up again. Spring and summer can be somewhat slower.
When I’m busy, I stay in maintenance mode: a baseline of outreach, staying visible on social media, and following up with warm leads. When things slow down, I get more aggressive with new outreach.
I also get inbound leads from LinkedIn, though this has slowed somewhat over the last year. I stand out on LinkedIn by posting at least three times a week, commenting thoughtfully on other people’s posts, and optimizing my profile to be found by editors and potential clients.
Applying for job postings on LinkedIn isn’t as effective as it was a few years ago, but it’s something I still do on occasion. There are a lot of really great newsletters that track job postings on a daily or weekly basis. If I find a job posting that looks like a good fit, I generally do three things: I leave a comment letting that person know I’m reaching out to them, I track down their email address and email them directly, and send three really targeted samples.
Commenting keeps me visible within the post itself. Sending a direct email is worth the extra effort because very few freelancers will bother finding the contact’s email address. That means you automatically stand out from everyone who just sent them a DM on LinkedIn.
And three samples are the right number since one isn’t enough to make a strong case to hire you, and sending five is too many for most people to read through. I also choose my samples based on the company and the kind of content they’re looking for.
How I determine my activity level
I tend to do my weekly planning on Sunday morning, and that’s when I decide what my pipeline activities for the week will look like. Obviously, one of the main things I consider is how many client articles I have to write that week. But there are two other less obvious factors I consider — my booked work and client signals.
My booked work
Every afternoon before I leave my desk for the day, I have a spreadsheet I fill in with three numbers for that day: work booked, work completed, and money received. Here’s an example of what that looks like:
The work completed section is how much work I actually did that day. So if I wrote one $1,000 article, that’s what I would write down. Money received is any money that showed up in my bank account that day. And booked work is any work a client assigned me that day.
In my experience, most freelancers try to optimize for the money they’re receiving. So when they want more money, they try to negotiate for shorter payment terms or worry about a client who is behind on paying an invoice. And you should definitely do those things.
The problem is, the money you’re receiving is a lagging indicator. It’s a reflection of work you’ve already done, not what you’re going to receive in the future.
Money received is water that’s already in the sink, while booked work is water flowing through the pipes. I have monthly and quarterly goals for my booked work, and if those numbers are on target, I know I won’t find myself in a financial pinch in a few months. If those numbers are low, that means it’s time to turn the water up on the faucet.
Honestly, tracking my booked work changed how I think about my business. When you’re looking at your capacity for the week, you’re only considering whether or not you’re busy right now. Whereas your booked work is about your trajectory for the coming months. Many freelancers can be slammed with work today, but still have a light pipeline. Tracking your booked work doesn't change that reality, it just means you see it coming and can do something about it instead of getting blindsided.
Client signals
One of the most underrated parts of pipeline management is learning to read the signals clients send before they pull back on work. In my early days of freelancing, when I lost a client, it always felt like it came out of nowhere. But over time, I’ve realized that’s rarely the case and that there are usually small signs first.
Last year, I had a long-term client who assigned me monthly articles through Slack. For years, he would send two assignments on the 1st of each month. Then slowly, that started to change. First, the assignments came a few days late. Then, a week late. Then, closer to ten days. Eventually, he told me he found a new job and was leaving the company.
More recently, a client emailed me to say they have a limited number of articles to assign this month, but that they’re open to original pitches. I immediately recognized that as a pullback signal.
The minute you start to see patterns like slower responses, fewer assignments, or changes in the tone or process, that’s your cue that it’s time to turn up the water on the faucet. You can increase your outreach, optimize your LinkedIn profile, or check in with clients you haven’t spoken to recently. You can start working to solve the problem before it becomes a full-blown financial crisis.
What gets most freelancers into trouble isn’t losing a client — it’s losing a client and only then starting to think about what they’re going to do next.
Final thoughts
If you turn off your actual faucet and then turn it back on again, the water starts flowing immediately. But that’s not the case with your freelance pipeline — if you let it dry up, it could take weeks or even months for the water to start flowing into your business again.
If I could go back to that Zoom call in 2018, I'd tell myself that building a pipeline isn't some complicated system you learn once and implement. It's just a habit of never fully looking away from your business, even when things are going well.