I bet you are familiar with buyer’s remorse. Heck, I actually can’t imagine you’ve never experienced it. 

Especially since it is a common psychological phenomenon characterized by feelings of regret or unease following a purchase. It typically occurs when a buyer experiences doubt or second-guessing about their decision to buy a particular item or service.

I’m grateful that it hasn’t happened too often, but when I have had buyer’s remorse…oof! Not fun.

But you know what I dislike even more? When I have had seller’s remorse

Yes, there is such a thing. Just as buyers can experience regret after making a purchase, sellers can also feel remorse after selling something.

Thankfully, I haven’t experienced this too often, either. When I have, though, it’s been because I either: 

  • sold something for too low a price, or 
  • allowed myself to negotiate against my business’ best interest in the long-run, or 
  • realized – after the fact – that I chose to work with a client who ultimately proved to be a wrong fit.  

Seller’s remorse is a phenomenon that mirrors buyer’s remorse in terms of regret and dissatisfaction. Both of which suck!

But, I don’t believe seller’s remorse is something we talk about enough. 

Exploring (Three Aspects of) Seller’s Remorse


The idea of seller’s remorse popped to mind as I was reflecting back on a conversation with a client. We were “T-accounting” the pros and cons of whether she should negotiate her quoted fee. 

Of course, there’s the financial ramification of doing so. But what I mostly heard during our conversation was that she felt like agreeing to negotiate was somehow diminishing the value of her work, expertise, and experience. 

On one hand she wanted to be flexible, especially if it meant getting the client/work. On the other hand, she didn’t want to get the short-end of the stick – financially or reputationally. And, I get it. 

Choosing to negotiate is complex, with emotional as well as financial ramifications. 

It involves an interplay of communication, strategy, and compromise with players in the room, as well as those who aren’t, influencing how everything plays out. Plus, what’s being negotiated holds a different meaning for everyone involved.

When or when not to negotiate is both highly personal and dependent upon the opportunity and what’s at stake. So, when negotiating, here are a few things to be mindful of in order to avoid regret or dissatisfaction with choosing to do so. 

Know why you’re willing to negotiate.
Do you need cash? Do you need this client to help you get the next one? Do you need the validation or proof of concept this opportunity can bring about?

Know your walk away number or terms.
Are you willing to lose the sale/deal altogether if the counter to your initial quote is too low? Do you know the concessions or compromises that are just a bridge too far? Do you know how to recognize when you are being bullied?

Know what you want in return.
You’re already leaving some money on the table. So make sure you’re not leaving anything else of value on the table, too. What are some tangible and intangible things you can request so that you don’t just feel like you are “giving up” something, but that you’re getting something you value in return. 

If you have a process for how you negotiate and know in advance the items noted above, you greatly minimize the likelihood you will feel dissatisfied with the outcome or regret the decisions made during the negotiation process. 


Just like I’m familiar with the feeling of remorse when you realize you negotiated against your best interest, I also know what it feels like to confront the fact you’re undercharging. 

Friends, mentors, and coaches used to always tell me I wasn’t charging enough. That’s less true today.

What you charge is another factor to consider when it comes to what can trigger seller’s remorse. 

And I actually think this is more subtle than the process of negotiating.

Getting your pricing “right” is a multi-layered mystery to be unlocked. A mystery because “right” is not some simple one-size-fits-all, universal number. It’s unique. 

When I work with clients on getting their pricing right for them, we dive into four (4) key relationships: their relationship with money, with themselves, with their business, and with the folks (prospects, clients, and customers) they serve.  

In the process, we invariably uncover an offer or perhaps an entire portfolio of offers that are under-priced.

Though pricing wasn’t my client’s challenge in this particular instance, I know I’m not the only one to have wrestled with the tendency to undercharge. And it is usually for one or all of the reasons below: 

What are you underestimating?
Many of my clients didn’t receive formal training in how to price what they do. When they set their prices, they either relied on how this was handled where they worked before striking out on their own; common industry practices; or on what their colleagues and peers are currently doing. 

In addition to the above, they also and wrongly approach pricing with only a calculator. And, they typically underestimate the time, effort, and resources required of them to create, deliver, and maintain their offers. 

They also don’t factor in both the “soft” and “hard” costs of doing and running a business. Or, the real costs of ensuring their business is taking care of their personal finances, too. 

So, once they see the “net” number after ALL the deductions and what they are able to do with what’s left over, they begin to resent the price because the compensation doesn’t feel fair. 

Who are you afraid of losing (or alienating)?
The price of your offers has several jobs. One of them is to attract and repel prospects, clients, and customers. 

Ironically, what I notice is that a lot of entrepreneurs and small business owners pay more attention to the folks their price is designed to repel. Because they don’t want to offend and/or they want to be accessible. 

Therefore, the fear of losing (or alienating) clients, customers, or prospects plays a larger sized role in their approach to pricing then is beneficial. Even though this usually means sacrificing their own financial well-being in the process.

How well do you articulate the value?
Notice I didn’t say “your value” or “your worth.” If you know me, you know I despise the phrase, “Charge what you’re worth,” with a passion!

And just like your pricing has several jobs, the same is true for your offers. Are you clear about those “jobs” in terms of what value it is bringing to your folks? How effective are you at communicating that value? 

If you lack clarity or are unskillful at communicating why someone should buy from you, this, too, can cause you to price what you offer too low.

Wrong Client (or Wrong Time)

In almost 30-years in business, I’m grateful (and lucky) to have only had four instances where I realized – after the fact – that the client was a wrong fit. Or, that while the client was a right fit, it was really the wrong time for them. 

Either way, experiencing seller’s remorse for this reason was awful and unfulfilling emotionally. 

It was also detrimental to my bottom line and cashflow. Because in each instance I refunded the money. Even though I was under no legal obligation to do so according to my agreement. But I didn’t want the “negative energy.” 🙂

The regret and dissatisfaction that stems from entering into a professional relationship that ends up not working out is the absolute worst feeling! 

And this type of remorse can manifest for various reasons, e.g., mismatched expectations, unreasonable demands, and boundaries not being respected. 

In my case, all of these were present and it boiled down to this: I didn’t follow my discovery/vetting process at all times!

Let’s just say I no longer make this mistake!

Preventing Seller’s Remorse?

Seller’s remorse can be just as distressing as buyer’s remorse. 

And while I suspect it is not possible to avoid ever experiencing it, you can minimize its frequency. 

Be proactive about why and when it might happen in the first place. Based on this, create a prevention and response plan. 

And, of course, let’s start talking about the phenomenon of seller’s remorse more! 

p.s. Today’s piece focused on the professional aspect of seller’s remorse. But, it can also be experienced personally with regard to personal possessions or estate related items that hold significant emotional value.

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