How to Break "Over Promise & Under Deliver" Cycle

Here’s the equation that covers the basics of the “over promise and under deliver” cycle.

Time＝money, right?

Consequently, less time＝less money, and more time＝more money.

Traditionally, we've thought that more time equals more money, but the mantra of the 21st century is "work smarter, not harder." So, in today's terms, less time can mean more money.

And in 2024 it’s also true that poor time tracking＝poor money tracking.

It's no secret that better time tracking equals more revenue, and most people agree on the high impact of proper time management on work productivity. Numerous stats prove it.

On the other hand, for you, a freelancer, it’s important to note that manual time tracking can become a side hustle itself. Just think of setting timers, coming up with task descriptions, and adding hours to timesheets. Plus, the extra time it takes to regain focus.

But how does all this fit into the “over promise and under deliver” cycle?

Well, when you don’t know where your time goes, and how you should use it, you’ll promise a client anything, just to impress them. However, making promises you're not fully committed to can damage your reputation and lead to long-term harmful consequences.

So, how can you break free from this cycle? Here's everything you need to know.

What does the “over promise and under deliver” cycle look like?

Simply put, it usually starts with a guesstimate of how much time a project will take and running with it.

When reality hits in the middle or end of the project, you start realizing that there is no chance of delivering on time, so you end up being late and sending a poorly executed result.

Here’s an example.

Let’s say that there’s a talented freelance graphic designer named Jake.

A client approaches him, asking him to design their new logo.

With all the work Jake already has, he promises to deliver the logo in three weeks. He approximately counts how much time it will take him to get to know the client’s industry, and the additional work he’ll have to put in after the client’s feedback mid-project. To Jake and the client, it sounds like a decent offer.

But Jake made a mistake because he wasn’t tracking his time.

He wanted to get the logo done and delivered in less than a month. But trying to fit in a new project with the existing workload can’t go as planned if you don’t track time properly.

The result? Jake exceeded the deadline and delivered a pixel fiasco. There was zero aesthetic harmony, no visual hierarchy, just a bunch of mismatched elements sorted in all the wrong ways.

Despite Jake's good intentions, he fell into the trap of over promising and under delivering.

The client was understandably dissatisfied and held Jake accountable for breaking his promise.

This incident affected Jake's reputation, portraying him as unpredictable, unreliable, and untrustworthy. Ouch.

Why do people end up over promising and under delivering?

People who tend to over promise and under deliver are commonly considered lazy, irresponsible, even self-absorbed, and incompetent.

In reality, that couldn’t be farther from the truth.

People who tend to over promise and under deliver are just bad at planning and time management. They get distracted by more urgent tasks, and let unpredictable circumstances dictate their daily routine, making it difficult to stick to their commitments. They are bad at estimating and don’t know where their time goes, working more time than promised and being burnt out.

So, rather than assigning blame, let’s recognize that many people face similar challenges with balancing their workload and allocating their time effectively.

Over promising and under delivering vs. under promising and over delivering

Is under promising and over delivering better than over promising and under delivering?

I mean, it might be.

You talk to a client, say you can’t deliver what they expected, they somehow agree to hire you and you end up delivering more than promised and quicker. So, you get the project delivered a few weeks before the deadline or you’ll include some extra features you haven’t discussed with a client.

It’s not a bad idea. I’m sure you’d rather be a person who finishes before the deadline than one who delivers late.

But under promising and over delivering can backfire.

Just because you delivered before the agreed upon due date and added an extra “sparkle”, a surprise to the project to wow a client, doesn’t guarantee client satisfaction. They might be impressed by your delivery time but not so much with the extra features you’ve added. As they say, sometimes the best surprise is no surprise.

So, I guess this is long way of saying:

• You are a professional.
• You need to make realistic estimates of how long a project will take.
• You don’t need to impress but to progress.

Now that you understand the dangers of both under promising and over delivering and over promising and under delivering, let's explore how you can break free from the “over promise and under deliver” cycle in just 3 quick steps.