So far, my April is off to a good start — as of April 3, I’ve already met my minimum goal for booked work, and I may even hit my stretch goal. However, I did notice one big red flag — two of my clients are accounting for a large percentage of my total income. This has happened slowly over the past few months. I lost a couple of steady but lower-paying clients, while a couple of other clients have had their content needs expanded. Which is great, but it does put me in a vulnerable position if they decide to pull back in Q2.

So my goal for the month is to find two to three new mid-tier clients — clients that need recurring work and pay between $1,000 to $2,000 per month. This will help stabilize my income, so I’m not so heavily dependent on one-time spikes.

I thought it would be interesting to outline my plans for finding new work in April and how I’m prioritizing each. There are four main strategies I’ll be focusing on — following up with existing clients, reaching out to warm leads, targeted cold outreach, and applying to job postings that look like a good fit.

1. Following up with existing clients

There are two ways I’ll be approaching my existing clients — the first thing I’ll do is look through any existing clients who haven’t assigned me any work, let them know I have availability, and ask if there’s anything they need help with. This almost always results in at least one or two new assignments.

But as I finish work for my current clients and turn it in, I’ll also let them know I have the bandwidth for more assignments in April and to please let me know if they need help with anything else. This often results in additional articles.

2. Reach out to warm leads

Next, I’ll make a list of everyone I’ve ever worked with or talked to about potential freelance work. These could be editors I haven’t talked to in a while, potential clients I had a call with that never went anywhere, clients I worked with who moved on to other companies, etc. The point is that this person already knows me, so they’re more likely to convert at a higher rate than cold emails.

3. Targeted cold outreach

I also have a list of 15-20 companies I plan to cold email. These are companies in my niche with an active blog or that are actively producing content somehow. I also like to look for companies that have active content or marketing job postings, which indicates they clearly invest in content.

For me, this looks like fintech or financial services companies and companies offering home equity solutions. I also plan to look into content agencies — this can be slightly less reliable, but these companies always tend to need reliable writers and understand how to work with freelancers. I’ll email most of those companies within the first week or two, and then spend the rest of the month following up.

You may notice my cold email list is pretty small. That’s because I like to keep my outreach narrow and focused. I think a common belief around cold emailing is that you have to contact hundreds of companies just to get a response, but that’s never been my experience. Keeping my list small helps me focus on companies that are likely to hire me, and then I focus my energy on following up with them.

4. Apply to job postings that look like a good fit

Finally, it’s still possible to find freelance work from LinkedIn job postings. I don’t spend a lot of time on this, but I do browse through job postings, and I’ll apply to anything that seems like it could be a good fit. The key is, you have to apply early — if you wait even a day or two, your message will likely get buried among the hundreds of other freelancers who already applied.

I recommend that you track job postings through All Things Freelance Writing or Freelance Opportunities! Both are newsletters that give you access to daily job postings, so you have a better opportunity to actually land work.

Some final thoughts

As you’re coming up with your own freelance marketing plan, it’s important to have a specific goal you’re working toward. For example, I always have a minimum income goal and a stretch goal. And I try to be specific in the kinds of clients I’m looking for. Having a specific goal gives me something to focus on, and it keeps me more engaged with my marketing plan throughout the month.

I also think it’s important to hold your marketing plan lightly and treat it like it’s an experiment. There’s a reason I named my Substack newsletter The Freelance Income Lab — because finding work as a freelance writer takes experimentation.

You may stumble onto a strategy that works well for a long time, and then it suddenly stops working. You may have to try different strategies to see what produces results. Sometimes strategies that didn’t work in the past will start working again.

And for me, treating it like an experiment helps me avoid becoming negative if something isn’t working. If you’re counting on a specific strategy to work and it doesn’t, it’s easy to throw up your hands and say, “I knew it. No one’s hiring. It’s so hard to be a freelance writer right now.” Whereas treating it like an experiment means you’re already acknowledging that it may not work. So instead of getting frustrated, you can shift and try something else.

If you have no marketing plan to speak of or don’t know what your freelance writing goals should be, I want you to know that’s completely normal, and it’s exactly the kind of thing we can work through together. I offer two Freelance Income Audits weekly, where we review your business and map out a clear path forward. If that sounds helpful, you can sign up for your spot or shoot me an email.

At the end of 2019, I decided to try my hand at creating and selling a digital course. I wanted to teach new freelance writers how to earn their first $1,000 a month, primarily using Upwork to find clients like I did. It was kind of controversial at the time since lots of people hated Upwork and insisted it was the absolute worst way to make money as a freelance writer.

In an effort to sell my course, I started doing free 30-minute calls with freelancers. I remember one girl got on the call, and she had never worked with a single client or made any money as a freelance writer. And when I brought up the idea of using Upwork, she shut it down pretty quickly. “I don’t want to give up 20% of the money when I’m doing 100% of the work,” she declared.

Ummm, last I checked, 20% of $0 is still $0, but okay.

But I’ve found that this sort of sentiment is common for freelancers because most spend their time worrying about things that don’t matter. They worry about payment fees before they have a single client. They obsess over contracts and scope creep. They focus on payment terms and how to get a client from Net 30 to Net 15. Meanwhile, the actual work of building a freelance business sits untouched.

I’ve been freelancing since 2016 and have earned over $100K every year for the past six years. So I can say with confidence that most of what gets discussed in freelance communities doesn’t actually matter. So let me tell you what does.

My core 4 as a freelance writer

I promise this article isn’t just going to turn into a rant. Because while most freelancing advice doesn’t matter, the flip side is that a few things matter enormously. In almost a decade of freelancing, I’ve found it really comes down to the following four things.

1. Finding clients

You cannot build a freelance business without clients, and yet this seems to be where freelancers spend the least amount of focused energy. And I think that’s because there’s a genuine disconnect as to what does and what doesn’t lead to a new client.

For example, updating your website is unlikely to lead to a new client. Websites are largely a vanity project, and most clients don’t care about reading through your about page or a description of your services. Your time would actually be much better spent optimizing your LinkedIn profile so clients could potentially find you.

Or even better? Email a previous client, tell them you have some availability, and ask if they need help with anything. Reach out to someone directly on LinkedIn and tell them what kind of services you offer. Ask your current clients to refer you if they hear of anyone looking for a freelance writer.

To be honest, the way you find freelance work also matters a lot less than you think. I got my start on Upwork, which plenty of people told me was a waste of time and a race to the bottom. It wasn’t because it got me in front of real clients who needed real work done. I don’t use it today, but I might if I needed to drum up some new business quickly and other strategies weren’t working.

Cold emailing works too. So does LinkedIn, reaching out to warm leads, referrals, and job boards. What doesn’t work is endlessly debating which method is best while never actually trying any of them. So pick one approach and make it your job to find a client. That’s it.

2. Turning in quality work on time

This point sounds obvious, but it probably doesn’t mean what you think it means. When I say “quality,” I’m not talking about being the best writer — I’m talking about giving clients exactly what they need, on time.

When I first started freelancing in 2016, one of the mental hurdles I had to get past was the fact that I had never graduated from college. I remember the first call I ever got on with a potential client. I was sooo nervous because I was sure he’d ask where I went to college. (Spoiler: he never asked, and neither has anyone else.)

In a way, I think my lack of a degree actually helped me because I knew I couldn’t compete based on experience or credentials. So instead, I focused on being the most helpful and the easiest to work with. And that’s why most of my clients have stayed with me for years — not because I’m the most talented writer they’ve ever worked with, but because working with me is easy.

I read the brief and include any keywords or internal links they asked for. I turn things in on time or early. I accept and implement feedback without getting defensive. I don’t require a lot of managing. That’s what quality actually means to a busy editor or content marketing manager, and it’s more valuable than you realize.

3. Maintaining your current client relationships

Honestly, I could have stopped at those first two points, and I think the article would’ve been complete. If all you focus on is finding the work and doing quality work, you’ll be in good shape. But I’m going to add in these final two points because I really do think they’ve been instrumental to my success.

Your current clients are the most valuable asset you have as a freelance writer, so you should protect these relationships at all costs. A client who trusts you and keeps assigning you work is worth far more than the energy it takes to constantly be pitching someone new.

I’ve gotten some of my best clients through editors I already had relationships with. Either from people referring me or from an editor leaving one job and taking me with them to the next one.

One of the biggest ways I’ve done this is by figuring out what each of my clients really wants in a freelancer. For example, I have one client who wants someone who doesn’t involve a lot of managing. This editor is very to the point and wants someone who will turn in a strong draft the first time and can take feedback.

Another client needs someone who understands SEO and can really stick to the briefs they send. One client often wants quick turnaround articles and is willing to pay more for them. I’ve been their go-to freelancer because I always respond to emails quickly, and if they need a rush assignment that's due tomorrow, I can pretty much always do it.

4. Know your numbers

This one took me longer to figure out, and I think it holds a lot of freelancers back without them even realizing it. In 2019, I was earning around $45K a year and felt pretty stuck. Then I came across a writer who openly talked about earning over $200K, and something shifted for me. I hadn’t been aiming higher because I didn’t know that kind of money was possible. That year, I doubled my income and I earned $90K.

The strategy that actually changed my income was figuring out my daily income goal. For example, let’s say you want to make $100,000. That means you need to earn roughly $8,300 per month. If you work 20 days a month, you need to earn at least $415 each day, which is a very doable rate for most writers.

Once I started hitting my number each day, I stopped worrying about chasing invoices or stressing about when money would come in. The daily goal gave me something concrete to aim at, and everything else followed from that.

The bottom line

In my opinion, those four things are all that really matter for freelance writers. Not your website, not your contract template, and not an Upwork fee. If you can master those four items, you’ll have a long and successful freelance career. The most successful freelancers I know are the ones who ignore the noise and just stay focused on what actually moves the needle.

If you’re not sure which of these four areas is holding you back, that’s exactly what a Freelance Income Audit is for. In one hour, we’ll look at your business together, figure out where the gap is, and map out what to focus on next. You can book your audit here.

Ever since I first started working at age 16, nearly every job I’ve held has been in customer service roles. I worked in an ice cream shop, as a server, a barista, and selling running shoes. People talk about how hard customer service is, but honestly, it’s always come easily to me. I just never saw the customer as a barrier to overcome — I really believe that 99% of people are nice, even on their worst days.

One of my favorite jobs was working at the front desk of a community center. It was easy work — I would greet people as they walked in and sometimes make small talk with members I recognized. Periodically, I would sign someone up for a new membership, but I spent most of my time either reading my book or talking to people.

The community center had a pool where members could swim laps, and the few lanes they had open were always in high demand. One Sunday, a man came upstairs, and he was visibly angry about something that happened while he was swimming laps. His face was all red, he was visibly shaking, and he started going off about how mismanaged the pool was.

I could’ve gotten defensive, and honestly, probably would’ve been justified in doing so. After all, he didn’t have to take his anger out on me, an $8 per hour employee who had absolutely no say in how the pool was run. But for some reason, I stopped and really listened to what he was saying.

He told me that he’d had various issues with the pool for months and recently had gone to talk to the general manager about it. He told her about the problems he’d encountered, and her response was basically, “Well, then go get a membership somewhere else.” But he didn’t want to go somewhere else — he wanted her to solve the problem.

When he was finished, I apologized and told him I would talk to my boss about what he told me. And when he left, he was a different person. He wasn’t angry anymore, thanked me for listening, and apologized for overreacting.

That interaction really changed the way I thought about customer service and how to interact with people. Because I realized his issue wasn’t really about the pool — it was because he could sense that the general manager didn’t want to help him. The energy he felt from her was, “How can I make this person go away?” The moment someone reacted to him differently, everything shifted.

What kind of energy are you bringing into your client relationships?

All those customer service jobs prepared me for freelancing, which is really just a customer service job in disguise. You may not think of it that way, but it is. Yes, you’re writing or delivering some kind of skill, but often, what clients are responding to is how it feels to work with you. And this is where I think some freelancers get it wrong.

I’ve noticed that a lot of freelancers are obsessed with setting boundaries with their clients. They spend a lot of time thinking about contracts, scope creep, or how quickly they should respond to emails. On some level, they’re trying to “train” clients on how to behave.

And to be clear, I’m not telling you not to have a contract or not to take steps to protect yourself. But underneath all of that is this assumption that clients are problems waiting to happen. And when you operate from that belief, it creeps into everything you do.

I see this all the time in how freelancers market themselves on LinkedIn. They post content that subtly (or not so subtly) lectures clients about all the things they don’t understand about working with freelancers. About why freelancers charge the rates they do, why you should never ask for a resume, or why 40 hours a week isn’t freelance.

And the question I always have when I see this kind of content is: Why would a great client be drawn to this? I feel like the clients you want already know this information, so who are those posts really for?

Here’s what I genuinely believe in my own business — great clients exist. Clients who are respectful and easy to work with. Not only do I believe they exist, but I believe you can build a business where that kind of client is the norm. But you find them by changing what you expect and how you show up.

What this looks like in practice

In nearly 10 years of freelancing, I have almost never had to chase clients down for payment. There have only been two instances where I haven’t gotten paid for work I did: the first was because the company filed for bankruptcy, and the second was in 2020 when a middleman didn’t get paid. That’s it.

I also don’t deal with constant scope creep, and I don’t feel like I’m managing difficult people. And it’s not because I have an ironclad contract — I believe it’s because on some level, I expect to work with people who respect me. And I show up in a way that reflects that expectation.

On some level, this is kind of intangible, but it plays out in very real and practical ways:

• How you respond to feedback — Answering negative feedback with defensiveness vs. genuine curiosity about what they actually need.

• How you handle scope creep — Whether it’s collaborative (”here’s how we can make that work”) or punitive (”that’s outside the contract”).

• How you talk about clients publicly: You attract different kinds of clients when your content isn’t defensive or lecturing people.

• How you follow up on mised payments: At a certain point, your attention shifts to finding and doing great work, not chasing down invoices or trying to get paid sooner — and that shift tends to solve more than you’d expect.

Final thoughts

I think it’s important to reiterate that I’m not telling you to forgo contracts or following up on overdue invoices. I’m not saying you should abandon your boundaries, but I don’t think boundaries are a foundation to build your business on. If you build your business around avoiding bad clients, on some level, you’ll keep orienting yourself around them.

But if you build your business around expecting good ones, you start creating an environment where that’s what shows up. So try asking yourself, “What kind of client relationships am I normalizing in my business?” Because that answer will shape your income far more than any contract ever will.

Of course, actually changing this is easier said than done. Because let’s face it — it’s hard to read the label from inside the bottle. When you’re in your own business, the way you do things feels normal — your pricing, your clients, and even how much you earn.

Most freelancers don’t even realize they have a pattern, but from the outside, it’s usually obvious. And once you see the pattern, it’s hard to unsee. And even small shifts in how you see your business can create outsized changes in how it performs.

That’s why I’m offering a limited number of Freelance Income Audits per week. During these one-hour sessions, we’ll look at your business together and identify what’s working, what isn’t, and where you’re leaving money or opportunities on the table. Then we map out small changes you can make moving forward.

Because in most cases, it’s not about making major changes overnight. It’s about making a few better decisions and letting those decisions compound.

If you’ve been feeling stuck, plateaued, or like you’re doing a lot of work without seeing it translate into the income you want, this will show you why. And if you’re not sure whether this is a fit, feel free to email me — I’m happy to talk it through.

👉 Freelancer Income Audit

Every year, I try to take two weeks off at the end of December. I rush to finish all my client work during the first half of the month so I can spend the remainder watching Netflix, enjoying holiday leftovers, and reflecting on my year.

One way I do this is through a client audit. I got the idea when I read The Four-Hour Workweek by Tim Ferriss, and I’ve continued to expand on his ideas as I do my own audit year after year. I tend to do my client audit at the end of the year, but you can do it anytime you feel you need a reset or just want to gain new insights into your business.

Here’s the process I follow:

1. List all your clients and how much they paid you annually

I always start with a simple spreadsheet that looks like this:

The first step is pretty easy — you’re going to list out every client you had that year and how much they paid you. If you use bookkeeping software like QuickBooks, this part should be pretty straightforward.

From there, you’ll figure out what percentage of your annual income each client represents. I always make a note of my top five clients for that year and what percentage of my income they accounted for. This helps me ensure my client roster is diversified enough and that I’m not overly reliant on a small handful of clients.

2. Track where each client came from

Next, you’ll write down how you found each client. This can also be really revealing, showing whether there’s a marketing opportunity you can lean into more. It can also show you if you need to diversify the ways you look for clients.

For example, I used Upwork to find most of my clients in the early days of freelancing. And one year, I realized I found 36% of my clients on Upwork, which felt like a yellow flag to me. I didn’t want to be overly reliant on a third-party platform that could change the rules at any time, so I knew I needed to diversify my outreach.

Once I’ve run all the numbers, I like to take some time to just think about each client and make notes. If they assigned me one article and never talked to me again, I’ll write that down. If I really like writing for a certain client and want to find more clients like them, I’ll write that down. Honestly, I’ll usually come back to this part over several days because new ideas will come while I’m on a walk or doing dishes.

3. Look for patterns

Once you’ve filled out the spreadsheet, the next step is figuring out what the numbers actually mean. Here are the kinds of things I’m looking for during a client audit:

• Is one client more than 25%-30% of my income?

• Where did my best clients come from? Do they have anything in common?

• Which clients were high effort and low-paying?

• Where did any recurring work come from?

• Which of my marketing efforts paid off the most?

For example, I remember doing this in 2017 or 2018 and realizing that one of my lower-paying clients actually accounted for about 20% of my work for that year. At first, I was kind of baffled, but then I realized it was because they consistently gave me 2-3 articles a week, while most of my other work was one-off jobs.

That taught me that I needed to look for more recurring work with higher rates. That was what eventually led me to focus on personal finance publications, a strategy that worked for me for many years and actually got me to six figures.

I also learned that once a client pays me $5,000 (total, not from a single project), they usually become a long-term client. So now, every time I start working with a new client, my number one priority is to reach that first $5,000.

However, watch out for outdated trends that no longer apply. For example, I did a client audit in 2021 and realized that three of my best clients came from one conference that I attended. I got excited and shortly after, signed up to attend that same conference later that year.

But when I finally went, I was disappointed to realize the experience was completely different, and I walked away with little to show for my efforts. After thinking it over, I realized that I attended the original conference in 2019 — then COVID happened, and everything changed. The point is, what works once won’t necessarily work forever.

4. Implement this information slowly

Okay, once you’re done with the client audit, how do you implement this information? My best recommendation is to slow down and not make any sudden decisions based on what you learned.

I know this may seem counterintuitive, but I find that whenever I want to take immediate action, it’s usually reactionary and not always in my best interest. So instead, I’ll sit with the information for a while and look for patterns. Then I’ll decide what I want to try in the coming year — maybe prioritizing referrals or doubling down on the channels that brought in my best clients.

The point of the audit is to learn more about your business. Over time, the patterns you notice help you make better decisions about marketing, what kinds of clients to pursue, and what needs to change if you want a sustainable business.

You don’t need to overhaul everything overnight. You just need to pay attention to what the numbers are telling you and use that information to make better decisions going forward.

If you’re reading this post, you probably already know you should be following up with potential clients. But most freelancers don’t do it often or with much consistency. So where’s the disconnect?

I’m guessing it’s probably some combination of the following reasons:

• They don’t want to bother people.

• It feels uncomfortable when someone doesn’t respond.

• They assume silence means no.

• They worry about looking desperate.

Because of this, I’ve noticed that most freelancers are constantly winging it when it comes to following up, so the results are minimal and inconsistent. To help you break free of this pattern, here are three mindset shifts I’ve had when it comes to follow-ups.

1. You need a follow-up routine

Years ago, I decided I wanted to start working out regularly. My goal was to work out five days a week, so I decided I would do it on Monday, Tuesday, Wednesday, Friday, and Saturday. But inevitably, there would be a Monday or a Tuesday when I just wouldn’t feel like working out. No big deal, I would tell myself. I’ll just skip today and do it on Thursday instead.

Do you think I made that workout up on Thursday? Um, no, I did not. Those were typically the weeks I only worked out two days, or just blew it off altogether. Over time, I realized that if I wanted to be consistent with working out, I needed to have a specific plan and I needed to stick to it.

And honestly, following up is no different. When you first cold email a prospect, do you know how long you’ll wait before following up with them? If not, there’s a good chance you won’t do it.

Personally, I always follow up on Thursdays. I don’t send cold emails or write social media posts, I just follow up with prospects or clients I haven’t heard from in a while.

After sending that first cold email, I typically wait a week and then send a follow-up email. If I still don’t hear back, I’ll send another quick email two weeks later. If I still don’t get a response, I might reach out to someone different within the company. You don’t have to copy my process for following up, but you should come up with your own.

2. My goal isn’t a yes — it’s to get a response

Okay, let’s state the obvious first. When I cold email someone, my preferred response is a yes. But when I follow up with someone, my ultimate goal is just to get a response. Because once someone responds, I know what to do next.

If they say yes, then great — we can talk about assignments or next steps. If they say no, that’s helpful too. It tells me that I should focus my attention elsewhere instead of continuing to wonder if that company might hire me.

The hardest situation is when you’re stuck in that in-between stage where you don’t know if the person is interested, too busy to respond, or simply not seeing your emails. And that uncertainty can drag on for months if you let it.

I’ll give you a real-life example of this. I had been writing articles for a fintech company for about five years when my main point of contact left the company last fall. Before he left, he mentioned that he would connect me with the person who would be taking over content, but that handoff never happened.

So I realized it was up to me to find this information. I managed to track them down on LinkedIn, so I sent a quick email introducing myself and asking if they needed any articles that month.

My inbox was a bit of a ghost town for the next couple of months as that person never answered a single email I sent them. After about three emails, I tracked down someone else at the company and reached out. Finally, in February, I received a response from the Director of Marketing explaining that they had decided they no longer needed freelance writing support.

Some freelancers might see that outcome as a failure, but I actually consider it a win because now I know exactly where things stand. Instead of wondering whether work might pick back up, I have a clear answer. And that means I can move on and focus my attention elsewhere while finding other ways to stay in touch.

3. A no today doesn’t mean no forever

One of the biggest mindset shifts I’ve had about freelancing is realizing that client relationships rarely have an obvious beginning and end. And one pattern I’ve seen in my own business is that once a client has paid me over $5,000, there’s a good chance that they’ll stick around for years. To give an example of this, my longest client has been with me since 2019!

But even if the relationship does eventually slow down or stop, it’s not uncommon for those same clients to come back at some point. Things change, content strategies shift, and opportunities have a way of resurfacing. That’s why I try not to mentally close the book on a client relationship.

The same thing can happen with cold outreach. I’ve had multiple situations where someone told me they didn’t need freelance writers at the time, only to reach out months later when their workload suddenly increased. Content needs can change very quickly inside a company. One quarter they’re fully staffed, and the next quarter they’re scrambling to find help.

Now, if someone clearly states that they don’t need freelance help, I don’t keep pestering them with emails asking for work. But I do look for ways to stay in touch with that person and remain top of mind. That could look like commenting on their LinkedIn posts or sending a quick check-in message once or twice a year.

Because in freelancing, you never really know when a past conversation or client might turn into a future opportunity. And when that happens, it’s a lot easier to restart a relationship that already exists than it is to build a brand-new one from scratch.

The bottom line

Following up will probably never feel completely comfortable. There’s always going to be a small part of you that wonders if you’re bothering someone or when you should just move on. But following up is a crucial aspect of building a sustainable freelancing business.

And over the years, I’ve realized that following up is really about reducing uncertainty in your business. You stay visible to the people who might hire you and keep relationships alive that could turn into work months or even years down the road.

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.

One claim I’ve heard a lot over the past couple of years is that cold emailing isn’t effective anymore. People often blame this on “AI slop,” but I don’t think this is necessarily the case. When cold emailing “doesn’t work,” I believe it’s because freelancers often go into it without the right strategy. For instance, they’re either targeting the wrong companies, unsure how to find the right contact person, or don’t know how or when to follow up.

I’ve been using cold outreach as part of my client acquisition strategy for years, so for me, there’s not a lot of guesswork anymore. So if you’re wondering if cold emailing can work for you but aren’t sure where to start, feel free to borrow my five-step process.

1. Pick an industry you want to target and be specific

Honestly, this is probably the most important step because if you pick the wrong kind of companies, you’re not going to get the results you want. You want to email potential clients who need freelancers and have a large budget to pay them. This can take some trial and error to figure out, but here are the primary things I pay attention to.

Company size

I prefer to work with companies that earn $50 million or more in annual revenue. My experience is that big companies have established processes for working with freelancers, which I appreciate. They also tend to pay better, and are just more likely to pay you in general since they’re well-established.

However, there are downsides, especially if you’re writing for really big, well-known companies. They can have very extensive (and sometimes tedious) onboarding processes, and some have Net 45 payment terms, or longer.

That doesn’t mean you can’t write for smaller companies. I’m just sharing my preference, and I realize it’s not for everyone. Every company type has its own set of trade-offs, and it really comes down to your personal preference.

Tip: Use Growjo to find a company’s revenue — it’s really easy to use and free. You just search by the company’s name, and you’ll see the revenue, valuation, and how many employees they have.

In-demand industries

Start paying attention to which industries are growing and might have a need for freelance writers like you. You can discover this by monitoring job boards, like LinkedIn or ProBlogger, or using a tool like Google Trends. You can also learn a lot about what’s working and what isn’t by talking to other freelance writers. I do this with a mastermind I’m involved in, but there are tons of online groups you can join.

It’s also a good idea to start paying attention to the kind of work you’re getting assigned. For example, a year ago, I was cold emailing a lot of insurance companies and getting no responses. Like, not even a polite, “We don’t need anyone right now, but we’ll keep you in mind in the future” type email.

So I stopped and looked at the work I was actually getting assigned and realized the majority was related to mortgages and home equity options. I immediately stopped emailing insurance companies and started targeting companies that offer home equity products. That strategy paid off, and I landed two new clients I still work with to this day.

2. Create a Google Sheet to track everything

Next, you’ll create a simple Google Sheet to track the companies you’re contacting. Here’s the template I use:

From there, you’ll come up with a list of 30 to 50 companies you want to target. ChatGPT can be a big help with this, but only if you use the right prompt. If you just ask for 30 healthcare companies, you probably won’t get the best responses. Here’s a prompt you can use:

Act as a B2B market research assistant. I am a [your niche] freelance writer who helps [type of companies] with [specific service]. Give me a list of 30 companies that:

• Operate in the [industry]

• Have between [X–Y employees] OR generate approximately [$X–$Y revenue]

• Are actively producing content (blog, newsletter, resource center, etc.)

• Would likely benefit from improving or scaling their content marketing

Prioritize companies that are growing or expanding into new markets. Include their website and a short sentence explaining why they would be a good prospect.

That alone should massively improve your results, but I wouldn’t stop there. Once it gives you a list, you’ll ask ChatGPT to refine it further with follow-up prompts. The exact prompt you use will depend on the kind of companies you’re looking for, but I might ask something like this:

“Now narrow this to companies that mention SEO, content marketing, or thought leadership in their job listings.”

3. Look for two contact people at each company

Now that you have your list of companies, you need to find two contact people at each company. I do this on LinkedIn using these steps:

• Search for the company name

• Click on the company’s LinkedIn page

• Filter by “People”

• Search for “Head of Editorial,” “Content Marketing Manager,” “Editorial Lead,” or some other variation

• Look through the results and pick two contacts at that company

Honestly, you’ll have to play around with the title. My best recommendation is not to overthink this — my experience is that most people don’t really care that much if you email the wrong person. In fact, when that happens, the person I email will often pass my name on to the correct contact, so it all works out.

Finally, you may be wondering, why do I have to find two people to contact? I do this for a couple of reasons. First, I have had it happen where I’ll email someone, and the email immediately bounces back. Or I get an auto-responder saying that person is on maternity leave.

When that happens, I can immediately move on to the next person without wasting time looking for someone new. But another reason is that if the first person I contact doesn’t get back to me, I will wait several months and contact the second person.

4. Find their email addresses

Once you have the correct contact person, you need to find their email address. I recommend using Hunter.io — it offers a free plan with 50 email credits per month. I do usually end up paying more for credits, but I think it’s well worth it because it saves me so much time.

Once you’ve created an account, you’ll click “Finder” in the left toolbar and then “Find Email by Name.” Here’s an example of how to do this using my own name and website:

Note: This email address is correct.

5. Email three to five people a day

Okay, now that you have all the information you need, you’re going to start emailing three to five people a day. Why only three to five? When you really need to drum up new business, I know it can be tempting to try to email 10 or more people a day. But in my experience, it’s hard to stick with that kind of volume for very long.

The main thing you want to aim for is consistency. If you can consistently email three to five people a day over the next month, you’re likely going to start seeing results and having conversations with people.

How to write a good cold email

I debated whether or not to share an email template with you, but honestly, I think you need to come up with this yourself. Because, to put it plainly, my email template isn’t going to sound like you and likely won’t resonate with your ideal client. But here are some recommendations I have for coming up with a good email:

• It’s okay to use a template: You don’t need to start from scratch every time — it’s okay to use a template that you change slightly for each new prospect.

• Choose a very specific subject line: Your subject line should let the person you’re emailing know exactly what the email is about. Don’t try to keep cute or clever with the subject line. Honestly, that just annoys most people and they may mark your email as spam.

• Keep it short: Obviously, you want your email to sound friendly, but don’t make the mistake of going on and on. People are busy, and if your email looks like a short novel, they will likely move on without reading it. I checked, and my cold emails are no more than two short paragraphs.

• Include three samples: I never send my entire portfolio to a prospect. Instead, I send three very specific samples that are relevant to them. For me, this is where personalization comes in because I’m showing them why I’m a good fit to write for their company.

• Include your LinkedIn profile: Personally, I don’t send prospects a link to my website and include my LinkedIn portfolio instead. LinkedIn is a better form of social proof than websites these days. Most clients really don’t care about digging through your services or reading your About page. When they click on my LinkedIn profile, they can immediately see that I’m a real person and I’ve written for dozens of companies in their industry.

• Double-check it before you hit send: Proofread the email one last time before you hit send. I know that sounds obvious, but you will feel like an idiot if you realize later you misspelled someone’s name.

Final thoughts about cold emailing

I think cold emailing is one of the most effective ways to find new clients, but it is a long game. You simply can’t cold email a bunch of people and expect it to work overnight. Sometimes you get lucky, but in many cases, it can take a while to bring on a new client.

Even if people respond to you, there will likely be some back-and-forth. They may ask to schedule a call with you to make sure you’re legit. If the call goes well and they decide to work with you, you may need to go through onboarding and sign a contract. Once it’s all said and done, it could take several months before you’re assigned a single article.

I spent a lot of time cold emailing in the spring and summer of 2025. That probably resulted in about $12,000 in work for the year, which isn’t nothing. But I’ve really seen it pay off in the last couple of months. One client I cold emailed in September 2025 didn’t assign me any work until mid-December. But in the past two months alone, I’ve done roughly $10,500 worth of work for that client.

So my point is to stick with it and don’t get discouraged. If you can really commit yourself to cold emailing, you’ll be amazed by where your business will be in a year.

Recently, I spoke to someone who’s been freelancing for several years. He’s a strong writer with articles in national publications and has steady work. Sounds good, right?

Not really — his main client is paying him peanuts per article, and he was struggling to get by financially. He was sending cold emails and trying to drum up new business, but it didn’t seem like anything was working.

This isn’t unusual — it’s a pattern I see play out all the time. And often, it’s not due to a lack of skill. On the surface, this writer was doing everything right:

• He was working hard and without complaint

• Delivering strong results consistently for his clients

• Actively posting on LinkedIn and building connections

• Had a writer’s website set up that clearly articulated his experience

So why was he struggling so much and what can this situation teach other freelancers? Let’s look at the three most common reasons this happens and how to fix them.

1. You’re settling for the wrong clients

There are a lot of benefits that come from writing for publications, especially in the early days as a writer. What do I mean when I say publications? I’m talking about Business Insider, U.S. News & World Report, Newsweek, USA Today, Bankrate…you get the idea.

Look, I’ve written for every single one of those publications, and they really helped me in the beginning. People like to hate on writing for exposure, but let’s face it, exposure can be pretty useful when no one knows who you are. Publications help you build credibility, but unfortunately, they’re no longer a good source of stable income.

This was what happened to many freelancers after the Google updates in 2024. Writers who were relying on publications for the majority of their income suddenly lost 70% of their clients overnight. Honestly, I was one of them — not only did I lose a client that paid me around $3,000 per month , but I also lost dozens of portfolio pieces when that site shut down.

That’s why these days, I focus on working with companies that offer a product or service. I’m also regularly auditing my clients to make sure no client accounts for more than 25% of my total revenue.

So if you’re struggling to make money as a writer, start by auditing your revenue sources. What percentage of your income comes from publications? Don’t get rid of clients who are still paying you money — even unstable or low-paying work is better than no work. But you can move to start replacing those publications with companies that align with your skills.

I recommend doing this through cold outreach. Let me know if this is a topic you’re interested in learning more about — I’m considering talking about it in a future post.

2. Your positioning is sending mixed signals

Can I be honest? I always hated it when other freelance writers would talk about positioning. Every time I bought a course about freelance writing, another writer was telling me to write out my unique value proposition, and it was my own personal hell. The same goes for coming up with an elevator pitch. I will skip that exercise every time.

But what I’ve learned over the years is this: Positioning isn’t about coming up with a clever elevator pitch. It’s about whether your work, online presence, samples, and outreach reinforce what you say you specialize in.

For example, if I say I’m an experienced writer but send samples as a PDF or Google Doc, it subtly undermines my credibility. If I connect with a potential client on LinkedIn and only have 35 connections or no profile picture, that sends a strong signal that I don’t know what I’m doing.

If you’re not sure whether you have this problem, my best tip is to ask another freelancer to review your online presence. But here’s the key - don’t ask them to review your website. I know as writers, we get very precious about our website, but I’m sorry to tell you, it doesn’t matter. Have them start with your LinkedIn page and portfolio, and ask them these questions:

• Can you easily tell who I work with?

• Can you figure out how to get in touch with me?

• Do my samples reflect the work I want more of?

• Is my portfolio easy to navigate?

From there, you can align your LinkedIn page and portfolio to match your target clients. When you get your positioning right, it builds trust and makes it easier for people to say yes to hiring you.

3. You stopped feeding your pipeline

Tell me if this scenario sounds familiar: you decide you’re going to get serious about finding new work, so you ramp up your outreach. You start engaging with people on LinkedIn or sending cold emails. Maybe you attend a conference or start intentionally following up with old clients you haven’t talked to in a while. And it works — in a couple of months, you’re completely booked with work. And because you’re so busy with work, you stop the outreach.

I’m guessing you know where this is going. It’s a tale as old as time — because you stop the outreach, eventually, a good portion of your work dries up. This can happen slowly, but when it finally happens, you’re forced to resort to panic pitching.

Another trap many freelancers can fall into is relying on a single client for the majority of their work. I touched on this in point 1, but it’s worth repeating. You get one really great client that pays well and gives you a steady stream of work every month. It feels stable, and in many ways, simplifies your life since managing one client is easier than managing six.

The problem is, you basically have a job without any benefits. Because you’re so reliant on that client, you don’t have much leverage to negotiate for better rates or assignments. And if that client decides they need to cut their freelance budget, you’re left scrambling to find new work.

Letting your pipeline dry up is the most common cause of a freelance income drop, and even experienced freelancers fall into this cycle, including me. But one thing that has helped over the years is focusing on cyclical marketing.

One of the things I’ve learned is that I can’t expect to have a steady workload — some weeks are heavy client work weeks, while some are lighter. So during those busy weeks, I focus on minimum pipeline maintenance. That looks like:

• Replying to editor or client inquiries

• Responding to email leads

• Commenting on an editor’s LinkedIn post

• Following up with a client after I’ve completed a project

• Sharing a recent article I wrote on LinkedIn

Basically, I’m doing enough to maintain my pipeline so it doesn’t dry up. Once I move into a lighter work week, I focus more heavily on marketing. During those weeks, I tend to focus on cold emailing and scheduling calls with potential clients.

This isn’t inconsistency, it’s energy allocation. Instead of expecting myself to have the same level of marketing output week after week, I realize that marketing ebbs and flows. The only thing that really matters is avoiding total inactivity.

Conclusion

Having your freelancing income suddenly drop feels demoralizing, but in my experience, it’s rarely a reflection of your writing ability. It’s about market selection, positioning, and pipeline discipline. And fixing these problems isn’t about working harder, it’s about rethinking how you find clients and present yourself to them.

If you made it to the end, thanks for reading. I’ll be exploring more ideas like this every week and focusing on helping freelancers build predictable income. Tell me — which point do you think you struggle with the most?