Freelance Paralegal Fail: Underpricing, Overpromising, and Learning from Mistakes

today we're diving into something we all experience but don’t always talk about: a good old-fashioned freelance paralegal fail.

Why? Because not everything is a highlight reel, and we learn more from our "what was I thinking?" moments than from perfection. So let’s get into this week’s freelance paralegal fail. The situation? Taking on a project, underpricing it, and overpromising on timelines—only to find out the project needs more time than expected.

I understand this situation deeply because I made the same mistake with my very first freelance paralegal client. And trust me, if you’re navigating freelance for the first time, chances are you’ll hit a bump or two in the pricing and planning department. But don’t worry—this is how we grow. Let’s dive in.

Storytime: My First Client

I launched my business on March 23, 2020, and by early April, I had my first client inquiry. It was surreal! I had posted once on LinkedIn about the benefits of working with a remote paralegal, and soon after, an attorney reached out, seeking help with a complex federal motion. I hadn’t worked in this court before, and the project was outside my wheelhouse, but I decided to take it on anyway.

Did I have my pricing figured out? Not really. I quickly scribbled down “$35-$40 an hour,” then settled on $30 to make myself feel better. When I spoke to the attorney, he asked for a flat fee since he was working pro bono. I made up a number on the spot—$250 for the motion, another $250 for a response. I thought it was fair, but I underestimated the workload. I ended up putting over 60 hours into that motion alone.

So…What Went Wrong?

The client was incarcerated, communication was a nightmare, and details were scarce. I couldn’t reach him regularly, and critical documents were missing. Curveballs kept coming, and I couldn’t anticipate how complex this would get. But I kept my promise to deliver without asking for additional payment, taking it as a lesson learned.

So, let’s talk about what to do when you’re in this position, and how to avoid it in the future.

Fixing the Fail: Communicate with Your Client

Here’s how to manage an ongoing project when timelines change unexpectedly:

1. Be Proactive: Don’t wait to inform the client if a delay arises. Let them know as soon as possible, explaining that you’re committed to delivering quality work.

2. Focus on Client Benefit: Frame your update around their needs. For example, “To ensure a complete and thorough product, I need a bit more time.”

3. Provide a Realistic Update: Push the timeline out enough to account for unknowns. This is your chance to underpromise and (hopefully) overdeliver.

4. Offer Solutions: Give them options, like breaking the project into parts or setting milestones, so they can see progress.

5. Apologize & Reassure: While you don’t need to over-apologize, do express gratitude for their patience. Reassure them that you’re committed to delivering a solid product.

Avoiding Future Fails

Here’s how to avoid these pitfalls with your next client:

• Assess Thoroughly: If you’re offering flat fees, make sure it’s for predictable, repeatable tasks. For complex or unpredictable projects, consider hourly billing or milestone-based pricing.

• Clarify the Scope: Define what’s included in your flat fee, from client communication to revisions. Be clear about extra costs for out-of-scope work.

• Consider Alternative Pricing Models:

  • Flat Fee with Defined Scope: Be clear about what the fee includes and excludes.

  • Milestone-Based Pricing: Charge based on phases, like initial research, first drafts, and final products, so you’re paid as you progress.

  • Hourly with a Cap: Give an estimated cost, but add a cap to reassure clients. This way, they know their max spend, while you’re still compensated fairly.

Wrapping Up: Lessons Learned

Clear communication, transparent pricing, and structured delivery will save you from these pitfalls. But know that fails will happen; the key is using them to deepen your client relationships. The way you handle mistakes can turn a bad situation into an opportunity for loyalty and trust.

And on that note, I’d love to hear about a fail (or win!) from your freelance journey! Share your story anonymously using the form below. And if you’re just starting out, check out my no-cost Freelance Paralegal Starter Course, covering everything you need to launch your business.

Thank you for joining me on this journey—until next time, embrace the lessons learned and keep pushing forward.

Now, excuse me while I wrangle my dogs back from their latest muddy adventure.