We all talk a lot about perseverance, commitment, certainly not quitting, and never giving up on people. Those concepts are all critical, of course, but like anything else, something positive in a different context can actually become a liability.
What I’m thinking about specifically is knowing when and how to let someone or something go without torturing yourself with guilt and “what ifs”.

When is a toxic relationship beyond saving? How much sacrifice is reasonable to ask of ourselves? What is the line between worthy commitment and masochistic folly?

I recently went through this difficult process with a member of my team. If I’m being honest with myself, in retrospect, the “red flags” that something was wrong were there from the beginning. I just wouldn’t allow myself to admit what they all added up to. It finally reached a point where no amount of rationalization and justification could hide what just wasn’t working and was never going to work. As to why I couldn’t admit those things, well, I’ll get into that a little bit later in this post. But first, the signs…

Obviously, both our expectations and our tolerances will and should be very different for personal vs. professional relationships, but I think it’s really all just a matter of degree, and the concepts still hold no matter what the context is. And those concepts are really simple: mutual respect, radical honesty about what each person is capable of and what is realistic to ask of them, clear expectations, and kindness and flexibility. None of us are perfect, so that last part is especially important. But, I think a lot of us struggle with the line between being flexible and accommodating, to being a doormat, or, even worse, an enabler of bad or toxic behavior.

In my particular experience (I’ll be using “they/them” to protect this person’s identity), the referral came by way of a trusted colleague, so I thought I was safe. But unfortunately, right into the first month of working together, I noticed that this person was on the defensive with me, their client, quite a bit, as if they didn’t trust me. And, looking back, I can see that the mark of someone who’s not likely “on your team” is someone who assumes you are not on their team. Someone who doesn’t trust you is likely to not be totally trustworthy.

However, I stress that trustworthy isn’t just about “not lying.” Trust is much more than that – for one thing it’s confidence that the other person is looking out for your best interests. Someone who isn’t totally trustworthy may be totally honest, but just not totally committed to the success of your joint venture.

Anyway, back to my example; it appeared that our relationship had already started off on shaky ground. And it really bugged me that, although this was a professional client-contractor relationship where this person was hired to promote my new business and brand, I soon realized they had not even read my book. Now, I want to be clear, this wasn’t an ego thing. I didn’t need any validation. This was “much bigger picture” than that, it was the fact that this person couldn’t possibly understand my philosophy, my passion project, my message or my past experiences which triggered my transformation, without that important information.

How could I have expected them to be a good advocate and messenger for me?

What soon followed was a series of incidents where I felt like I was left hanging, like this person wasn’t holding up their end of the bargain.

Then came the deal breaker: when I tried to address my concerns with this person, they responded that in fact I was the one with unreasonable expectations, that they never said they would do the things I was asking (which were also contained in our contract), and that I was presumptuous and overbearing to expect such things.

Well… that did it for me. I knew I had to terminate the relationship.

And, here’s the thing: this person was a service professional and I was their client. And yes, I am also a service professional with clients who engage me for my advice, consulting, coaching, and other services. Nonetheless, at first, I took this person’s reaction to heart, because I was already unsure about the reasonableness of my concerns, and my expectations.

This person is an expert in their field, I told myself, which is why you hired them, so they know better than you, right? But then I remembered that, like I said, I am a service professional as well, and I asked myself how I would react if one of my clients had brought similar concerns to me. And I can honestly say that even if my hypothetical client were objectively off-base, demanding, and unreasonable, I still wouldn’t tell them so. I would validate their feelings of dissatisfaction and try to come up with a concrete plan to address those feelings, even if part of that plan involved me communicating myself better on what would be reasonable to expect of me, the service provider.

Unfortunately, in my case, this person did the exact opposite.

So, I did what I had been subconsciously dreading since almost the start of our professional relationship: I terminated our contract and therefore our working relationship. Disclaimer: I’m not an attorney and I’m not giving you legal advice. But I did consult with an attorney, and she told me that often-times non-attorneys think of contracts as these unbreakable bonds, when in fact a lot of contracts have the conditions for early termination built right into them for precisely this purpose: when one or both parties to the contract feel, that they are not getting what they signed up for.

I strongly recommend you getting independent advice for your own business dealings, but start by actually reading the contract you signed to see what your options are. In my case, it turned out that even though the contract was for a certain number of months which hadn’t yet finished, the contract also specifically stated that it was an “at will” relationship that could be terminated for any reason.

Upon confirming things with my attorney, I wrote an email to this person terminating the contract.

My email merely stated that we had spoken about my concerns, that our conversations made it clear to me that my (and their) expectations about the contract were not the same, and since there was a gap between our respective understandings about the contracted services, the only reasonable thing to do was cancel the contract and cease service from that date forward.

I never blamed that person for why there was a gap in our respective understandings, or enumerate each time I was dissatisfied with the relationship, or any other blame game tactics. I merely made it neutral, amicable, and to-the-point.

Whether it’s a dysfunctional personal/professional relationship, or whether it’s letting go of a certain project or goal that isn’t working, I think we often have one of two opposite (but equally distorted) reactions – in fact, sometimes we can have both all at once! And those two reactions are: it’s all their fault and they should know that, and/or it’s all my fault and I should push forward, persevere, and will it into success. Both of these reactions are ultimately harmful to ourselves because both increase stress, and neither leads to strength.

And, because I want you to be prepared and ready the next time you’re up against a difficult situation or having to make a tough choice; I’ll share with you what I do. I want you to ask yourself (and I remind myself to ask myself all the time): “What outcome do I hope to have, and is this action likely to lead to that outcome?”

This is where you need to be brutally honest with yourself, because If we’re telling ourselves not to give up, not to write someone off, to buck up and take the pain: sometimes that is honestly the right move, but only if we can honestly say to ourselves that this commitment and grit, has a likely and foreseeable outcome.

But… sometimes it doesn’t. And if it doesn’t, then the next healthy step is to ask: “Why am I so unwilling to let go? What consequence am I afraid of? Being un-liked? Thinking of myself as a quitter? Why do those outcomes matter to me?” That radical honesty with yourself can be another really important step towards inner strength and conviction. Try it next time.

When we’re tempted to enumerate everything in the name of “honesty”, just who are we being “honest” for?

Are we using the concept of honesty as a fig leaf to mask either self-blame and guilt or vindictiveness toward the other person? What is the other person’s likely reaction to our self-professed honesty, and is that reaction the one we’re looking for (whether or not it’s what “should” happen)?

Sometimes being honest means holding back, not spilling everything out. It means giving the other person a graceful exit, plausible deniability.

It’s all too easy to either blow a single instance of disappointment out of proportion in an otherwise fruitful relationship, or on the other hand continuously excuse small slights and disappointments individually, while failing to see a larger pattern of a relationship or project that’s just not working.

Strength means not doing either: it means maintaining a healthy perspective and seeing the bigger picture in terms of what’s best for all parties involved.

Strength means not being petty in the name of honesty. Strength means taking a step back and asking ourselves what is the likely outcome of our intended action before we take that action, and whether that likely outcome is what we’re hoping to achieve.

Strength means working backwards from our goals: “What result do I ultimately want, and what actions give me the best chance of achieving it?” instead of, “What actions do I want to take because they’re cathartic or because I think they’re ‘right’, even if they are ultimately not helpful or even counterproductive?”

Here are the ingredients for the balance I’m constantly seeking and I hope I can help you seek: radical honesty, perspective and big picture, kindness, result-driven actions, and simultaneously not being afraid of letting go (sometimes) while also not being afraid to hold on (sometimes). If we can hold those seemingly contradictory concepts in our minds, we just might find that they’re actually complementary, not contradictory, after all.

Are you struggling with letting someone or something go? How will you deal? If you think your story will help someone in our tribe, please share how you overcame it by finally cutting-the-cord.