Stop Sabotaging Your Freelance Career: Fill Your Pipeline and Win More Clients

I've been noticing a recurring mistake that many freelancers make day after day—and it’s really pissing me off. I’m here to get it off my chest and share some hard truths about how freelancers often sabotage their own success.

For context, we’re building an AI tool to help freelancers find more clients more easily. Every morning, we scan the internet and send you a personalized list of up to five jobs and opportunities that match your interest criteria. Working with over a hundred different freelancers has made it clear that there are some unmistakable patterns emerging.

Table of Contents

1. Patterns

2. Levels of Success

3. Excuses

4. Proactive Mindset

5. Waiting for Clients

6. Habits

7. Fill Your Pipeline

8. Pay Your Bills First

9. Conclusion

Patterns

There are two buckets of users in the freelance world:

• Bucket Number One: The very motivated, proactive type who put in the work to get those jobs and get hired.

• Bucket Number Two: Not to call them lazy, but these are the unmotivated users—those who doubt themselves and therefore don’t take nearly as much action.

Levels of Success

There’s a big difference in success between these two groups. No matter how good the recommendations or how perfect the match the opportunities might be, if you’re in the second bucket, you’re likely not reaching out to as many opportunities as you should. This lack of action is one of the main problems holding many back.

Excuses

Even highly qualified freelancers—those who are really, really good at what they do—often don’t get hired simply because they’re not reaching out enough. They always seem to find a reason not to apply: either the match isn’t 100% perfect, or they have doubts about the offer. Instead of asking the client for more details, they choose not to reach out at all. If the ad isn’t exactly what you had in mind—a perfect client—then you simply won’t make the move, and as a result, you end up missing out on opportunities.

Proactive Mindset

I was seriously shocked at how proactive some freelancers can be. Let me share a real story: there’s this guy in Berlin—super motivated and proactive. We sent him a couple of job offers that were a disaster; one was for a short film in Berlin (not exactly his usual interest) and the other was for a makeup artist—a role not even remotely related to his work as a filmmaker. Yet, he reached out anyway. When I asked him why, he explained that the people posting the job were exactly the ones he wanted to network with. That proactive mindset is exactly what sets the successful freelancers apart.

Waiting for Clients

It’s incredibly frustrating to see freelancers who are exceptionally good at what they do simply wait for clients to come to them. They believe that showcasing their work is enough, expecting that quality will automatically attract the right opportunities. Meanwhile, you see people who might not even be as good landing gigs that you feel you deserve—all because they made the effort to send a message and ask for what they wanted.

Habits

Reaching out isn’t an occasional effort—it’s a daily habit for successful freelancers. Whether it’s daily or weekly, the key is consistency. Successful freelancers make it a regular practice to connect with potential clients on Instagram, slide into DMs on Facebook, network on LinkedIn, and apply via job posts on freelancing websites. It doesn’t matter what project you’re working on today; if you’re the kind of person I want to talk to, you need to make reaching out a habit.

Fill Your Pipeline

Here’s the last thing I want to emphasize: when you’re a freelancer—especially if you’re an artist and you’re broke—even if you did well last month, if you don’t know how you’re going to pay your bills this month, you cannot be picky. Your number one priority must be to keep your pipeline full at all times so that you always know where your next job is coming from. Once your calendar is full and you’re no longer scrambling for your next gig, then you can afford to be selective. Only then can you start searching for better clients, better projects, and better pay. It’s also much easier to negotiate for higher rates when you can confidently say no to a client because you’re not desperate.

Pay Your Bills First

It’s bizarre to see freelancers who are stuck in a limbo—wanting to make a certain amount of money per month but only accepting projects that are their “ideal perfect” gigs. Essentially, they’d rather starve than work on a project that isn’t 100% what they want. That’s a dangerous mindset when your top priority should be ensuring you can pay your bills.

Conclusion

I hope this rant was useful. Remember: if you’re serious about your freelance career, you need to fill your pipeline, reach out consistently, and never let doubts hold you back. Also, feel free to check out our Lin, AI-powered tool tool, that sends you job recommendations every morning.