The Uncomfortable Truth of Working with People

Let’s talk about something that every business owner or freelancer has experienced but rarely enjoys addressing—working with clients who don’t keep their promises.

Unpaid invoices. Last-minute meeting cancellations. Constant delays. Sound familiar? These situations aren’t just frustrating—they’re costly, unproductive, and downright exhausting. But they’re also a reality of working with people.

So, how do you navigate these challenges without losing your sanity (or your business)? Let’s break it down.

The Reality of Broken Promises

First, let’s acknowledge the elephant in the room: people break promises. It might be intentional, it might be accidental, or it might stem from poor time management on their part. Whatever the reason, the result is the same—you’re left dealing with the fallout.

Late payments mean cash flow issues. Missed meetings waste time you could’ve spent elsewhere. Broken promises erode trust, making future collaboration nearly impossible.

It’s uncomfortable, but it’s a reality every business owner faces at some point.

Why These Issues Happen

The root causes of these problems vary, but common culprits include:

A Lack of Accountability: Some clients simply don’t feel the same urgency about deadlines or commitments as you do.

Poor Communication: Misunderstandings or unclear agreements often lead to missed expectations.

Overcommitting: Clients might genuinely want to follow through but overestimate their capacity, leading to broken promises.

Understanding why these issues happen is the first step in preventing them.

How to Set Boundaries and Protect Yourself

1. Clear Contracts Are Key

Never, ever start work without a signed contract. Your contract should outline payment terms, deadlines, cancellation policies, and penalties for late payments or missed meetings.

A well-crafted contract isn’t just about legal protection—it sets clear expectations and holds both parties accountable.

2. Enforce Your Policies

It’s one thing to have policies in place; it’s another to enforce them. If a client pays late, enforce your late fees. If they cancel last-minute, charge the agreed-upon fee.

This might feel uncomfortable at first, but remember: your time and expertise have value. Letting things slide sets a precedent that it’s okay to disrespect your boundaries.

3. Require Upfront Payments

To avoid cash flow headaches, require a portion of your fee upfront—whether it’s a deposit or payment in full before starting a project. This weeds out clients who aren’t serious and protects you from unpaid invoices.

4. Overcommunicate

Many issues arise from miscommunication. Confirm meeting times, clarify deliverables, and follow up on payments promptly. The clearer you are, the fewer excuses clients have.

Handling Difficult Situations with Grace

Despite your best efforts, situations will arise where clients push boundaries. Here’s how to handle them professionally:

Stay Calm: Emotional reactions can escalate the situation. Approach the issue calmly and focus on finding a resolution.

Document Everything: Keep records of all communication, invoices, and agreements. This helps you build a case if disputes arise.

Know When to Walk Away: If a client consistently disrespects your time and effort, it’s okay to part ways. Not every client is worth the hassle.

How to Avoid These Situations in the First Place

One of the best ways to prevent these issues is by vetting clients before working with them. Look for red flags like hesitation to sign contracts, vague communication, or resistance to upfront payments.

Set the tone early by being clear, professional, and firm in your policies. Clients will take you as seriously as you take yourself.

Final Thoughts

Working with people is always going to have its challenges. Late payments, missed meetings, and broken promises are part of the territory. But by setting boundaries, enforcing contracts, and communicating clearly, you can minimize these headaches and protect your business.

And when things do go wrong? Handle them professionally, learn from the experience, and move forward.

Remember, your time and expertise are valuable. Don’t let anyone convince you otherwise.

Here’s to running a business on your terms—because you deserve it.