The Client I Should Have Fired in Year One (But Kept for Five Years Too Long)

The Text That Landed at 10:47 PM

It was late on a Friday night—10:47 PM to be exact—I was just going to bed when my phone buzzed with another text.

I was at home. The week was done. I should have been relaxing with Caroline. Actually I should have been asleep.

Instead, I was reading the third demanding text of the evening from a client who seemed to believe that paying for our services entitled them to 24/7 access to my personal time.

“Des, I need this first thing Monday morning. Have you seen the 3 emails I send and my text messages. Can you prioritise this over the weekend? I need it done”

No please. No acknowledgment that it was late late on a Friday. Just the expectation that I would drop everything—again—because they needed something.

I sat there staring at my phone, feeling that familiar knot in my stomach that had become a regular companion whenever this client’s name appeared in my messages or my inbox.

And I thought: Why am I still doing this?

But I already knew the answer. Because they paid on time. Because the revenue was good. They were a “good” client. They were a big client. They were in a network with other firms who we wanted to work with, which he regularly reminded me.

Because letting them go felt like admitting failure.

Because I was afraid.

This is the story of the client I should have fired in year one but kept for five years too long. And what it cost me to finally learn one of the most important lessons in business:

Not all revenue is good revenue.

The Beginning: When Red Flags Look Like Opportunity

It was early 2005—my first full year in business. I’d just started OmniPro, having walked away from that partner designate role after 2.5 weeks. Money was tight. Every client felt critical to survival.

This client came through a referral. They ran a mid-sized accounting practice and needed help with technical support, file reviews, and some complex audit work. They wanted in house training. They needed co sec support

The scope was significant. The fee was good. On paper, it looked like exactly the kind of client I needed.

But there were signs from the very first meeting.

They questioned every quote. They pushed back on every timeline. They had a habit of sending “urgent” requests at odd hours—late evenings, weekends, bank holidays—and expecting immediate responses. Scheduled engagements often got pushed back on their end but the deadline for delivery seldom got extended on our end.

During our initial consultation, they interrupted me constantly. They dismissed several of my recommendations before I’d finished explaining them. And when I suggested a particular approach to a technical issue, they said: “Well, I’m not sure you understand our business well enough yet to make that call.”

I remember driving home from that meeting with an uneasy feeling.

But then I told myself the story I’d tell myself dozens more times over the next five years: They’re just demanding because they care about quality. They’re successful and they have high standards. You need to prove yourself. This is what building a business looks like.

I took them on.

The Pattern Emerges

Within the first couple of months, the pattern was established.

Requests would come at 6 PM in the evening looking for a response by the morning. The email would land on a Friday for delivery for a Monday meeting. “Urgent” technical queries would arrive during my family time. Boundaries I attempted to set were ignored or dismissed as “not how professional services work.”

When I delivered work on time, there was no acknowledgment—just the next urgent request. When I asked for clarification on a vague brief, they’d act frustrated that I didn’t already understand what they needed.

They paid their invoices on time—I’ll give them that. But every payment came with the unspoken expectation that I was now on call, essentially owned, until the next invoice was due.

I started to dread seeing their name in my inbox.

I was selling my soul.

Sunday evenings became anxious. Would there be an email waiting that would ruin my week? Friday afternoons lost their relief—there was usually a last-minute request as they headed into the weekend.

My team started to notice. When this client called, whoever answered the phone would grimace and mouth “It’s them” before transferring the call to me or whoever they were looking for that day.

But the revenue was good. And in those early years, when every pound felt critical, I convinced myself I couldn’t afford to lose them.

The Breaking Point (That I Ignored)

The real breaking point came in year four—2008.

We were coming out of that first major cash crisis and a recession was looming on the horizon I was working 60-70 hour weeks trying to stabilize the business. Caroline was working ridiculous hours at her day job and somehow managing everything at home.

This client sent an email on a Saturday morning—9:23 AM—about an audit opinion report that “absolutely had to be completed” by Monday.

The work would take 6-8 hours minimum. It was technical, detailed, and required deep concentration. And they were asking me to sacrifice my entire weekend.

I remember standing in my kitchen, reading that email, and feeling something shift inside me. We didn’t have kids at the time and it was 100% recovery at a good rate. What else would I be doing?

This wasn’t professional service. This was being taken advantage of.

I typed out a response: “I appreciate your urgency, but I’m not available this weekend. I can have this completed by Wednesday morning instead.”

I hovered over the send button for what felt like ten minutes.

And then I deleted it.

Instead, I sent: “No problem. I’ll have it ready Monday morning.”

I spent Saturday and most of Sunday working on that file. Caroline said nothing, but I saw the disappointment in her eyes.

The client’s response when I delivered Monday morning at 8 AM? “Thanks.”

One word.

That was the moment I should have fired them.

But I didn’t.

Why I Kept Them (The Uncomfortable Truth)

Looking back now, I can see exactly why I kept them for another two years after that breaking point.

It wasn’t really about the revenue—though I told myself it was.

It was about what firing them would have meant about me.

If I fired them, it would mean:

• I couldn’t handle demanding clients (maybe I wasn’t cut out for this)
• I was turning away good money (maybe I wasn’t a real business person)
• I was being difficult or unprofessional (maybe they were right to demand so much)
• I had failed to meet their standards (maybe I wasn’t good enough)

I was trying to prove something—to them, to myself, to everyone who’d doubted whether I should have left that secure partner role.

And so I kept accepting their late emails and texts. I kept sacrificing weekends. I kept letting them set the terms of our relationship.

I kept letting one client define my worth.

The Final Straw

The end came in 2010. Five years after taking them on.

It was the weekend of my daughter’s baptism. They called me on a Thursday and needed an emergency meeting in my office. This was unusual as they seldom came to me. Some mediation meeting was happening on the following Tuesday, and they felt I was the only one who could draft the report to solve the problem.

I explained I had a christening and that it just wasn’t possible. They pushed back but you have all day Friday and Saturday and Monday. I held firm but they were desperate. They quoted a massive fee. Money was no object if the work could be done.

I wasn’t selling services anymore I was selling my soul. I was selling my soul to the highest bidder.

I did the work. It impacted on the weekend. Caroline’s family were staying. I tried to make it as inconspicuous as possible. I worked late at night Friday and Saturday and early in the morning. We had the baptism on Sunday but I had this deadline looming and all their promises about the completeness of the information were way off the mark as was the estimate of the time. It was hanging over me all weekend and I was warned by Caroline not to let this impact the celebration, so I smiled but the smile was hollow as this black cloud consumed me

Caroline and her parents went to bed on Sunday night and I snuck back down to do the work. I created a time completion plan. It was a disaster I needed 12 hours to completed and I was meeting them at 3.00 PM the next day. I worked till 3.00 got up at 6.00. Into the office and worked like a demon.

Exhausted I got the report finalised at 2.55 and pressed send.

I got an email back 2 minutes later. Our meeting at 3.00 wasn’t necessary. The client wasn’t feeling great so the cancelled the mediation on Tuesday until the following week so the client could get themselves together.

I’d just sacrificed my weekend to meet their impossible deadline. I’d sacrificed my daughters baptism and a family celebration. I had upset my wife. They cancelled the mediation because the client didn’t feel up to it.

Something broke.

I said very calmly: “I’m going to stop you there. This relationship isn’t working anymore. I’ll complete any outstanding work we’ve committed to, but after that, I think it’s best if we part ways.”

There was silence on the other end of the line.

Then: “Are you firing us as a client?”

“I’m recognizing that we’re not a good fit for each other.”

They were shocked. Actually shocked. Because in their mind, they were a great client—they paid on time, they gave us lots of work, what more could we want?

They didn’t see the cost.

The cost of the late emails and texts. The cost of the Sunday work. The cost of the short deadlines. The cost on me and my team. The cost of the anxiety that had become attached to seeing their name. The cost of constantly feeling not quite good enough.

The cost of letting one client set the terms for my entire business.

We parted ways. They were unhappy about it. They suggested I was making a mistake. They reminded me how much revenue I’d be losing. They threatened me as to what this would do for my reputation in the marketplace and their beloved network.

I held firm.

And the strangest thing happened: I felt lighter than I had in five years.

What It Taught Me (The Expensive Way)

That client cost me far more than the revenue they brought in.

They cost me weekends with my wife and new baby. They cost me sleep. They cost me the confidence to set and hold boundaries with other clients. They cost me the example I set for my team about what kind of clients we accepted.

Most importantly, they cost me five years of believing that I had to tolerate being treated poorly in order to be successful.

Here’s what I learned—the expensive way:

1. Not All Revenue Is Good Revenue

Some revenue comes with costs that don’t show up on your P&L. The cost of your time, your energy, your self-respect, your family relationships, your peace of mind.

If a client makes you dread opening your email, that’s a cost. If your team grimaces when they call, that’s a cost. If you’re sacrificing what matters to serve someone who doesn’t respect what you do, that’s a cost.

Sometimes the most profitable decision is turning away money.

2. How You Let One Client Treat You Sets The Standard For All Of Them

Every time I said yes to that client’s unreasonable demands, I was teaching every other client what was acceptable.

I was teaching my team what to expect from client service. I was teaching myself what I was worth.

You can’t simultaneously accept being treated poorly by one client and expect to build a practice where you’re respected by others.

The standard you walk past is the standard you accept.

3. You Can’t Build The Business You Want By Serving Clients You Dread

I kept telling myself: “Once I’m more successful, once I have more clients, once I’m more established—then I can be selective.”

But it doesn’t work that way.

The clients you tolerate now become the foundation of your reputation. They refer people like themselves. They shape your brand. They define what you’re known for.

You can’t build a practice full of dream clients while still accepting nightmare clients.

4. Fear Is The Worst Reason To Keep A Client

I kept them because I was afraid:

• Afraid of losing the revenue
• Afraid of admitting I’d made a mistake
• Afraid they were right about me not being good enough

Fear makes terrible business decisions.

The moment I fired that client wasn’t the moment I found courage—it was the moment I recognized that the cost of fear was higher than the cost of letting them go.

5. Sometimes You Need To Fire Clients To Make Room For The Right Ones

Here’s what happened after I let them go:

Within three months, I had two new clients—both of whom respected boundaries, both of whom appreciated our work, both of whom paid better than the client I’d fired.

But I couldn’t have taken them on if I’d still been spending all my time and energy managing the toxic relationship.

You can’t fill a glass that’s already full. Your have to pour some out to make room for more or you need a bigger glass

The Lesson For You

This connects directly to Your Ideal Customers in the ProfitPro 6-Step Success Path.

Because defining your ideal customer isn’t just about who you want to serve—it’s about who you need to NOT serve.

You need a Red Velvet Rope Policy to decide who gets in.

Here are the questions you need to ask yourself:

About Your Current Clients:

• Which clients make you dread opening your email?
• Which clients do your team grimace about?
• Which clients consistently disrespect your time and boundaries?
• Which clients pay you but cost you more than the money is worth?
• Which clients would you not take on today if they came to you now?

About Yourself:

• What are you tolerating because you’re afraid of what letting go would mean?
• What’s the real cost of that fear?
• What would you do differently if you weren’t afraid?
• What standard are you accepting by walking past behaviour you know is wrong?

About Your Business:

• Can you build the practice you want while serving clients who don’t respect what you do?
• What message are you sending to good clients by accepting bad ones?
• What’s waiting for you on the other side of letting go?

The hardest part isn’t firing the bad clients. The hardest part is admitting to yourself that you should have done it years earlier.

YOUR TURN

Be brutally honest: Do you have a client right now who you should have fired years ago?

What’s keeping them? Is it really the revenue—or is it the fear of what letting them go would mean about you?

What would change in your practice if you had the courage to create space for clients who actually respect what you do?

I’m curious: Have you ever kept a client way longer than you should have? What finally made you let them go? And what did you learn from waiting?

Drop a comment. Because sometimes we need permission from someone else who’s made the same expensive mistake.

Tomorrow: Letter 5/21 – “The Myth of ‘Making It’ (And Why I’m Still Climbing After 21 Years)”

If you’ve ever wondered when you’ll finally feel like you’ve arrived—spoiler alert: you won’t. And that might actually be okay.