Knowing When to Let Go of Relationships: 3 Signs It’s Time to Move On 
“Being deeply loved by someone gives you strength, while loving someone deeply gives you courage.” ~Lao Tze
Thanks to the Internet, our lives are full of people. We’re connected literally all the time.
And yet, despite our ceaseless connection, we feel disconnected.
As the pace of life becomes ever more frenetic, we’re like charged atoms, bumping into each other more and more, pinballs in the machine. We come into contact (and conflict), but we don’t commune so much.
As real relationships of depth and quality become harder-won in this busy new world, their value is more keenly felt. Simply put, in the words of Brené Brown, “Connection is what gives purpose and meaning to our lives. It’s why we’re here.”
As we fight to carve out space for these connections whose value has become so apparent, it’s natural that we cling to them more dearly.
However, sadly, often the tight clinging to something is the sign that the time has come to let it go. With something as valuable as a relationship, how do we know when that time is? How do we know when it’s time to move on?
I’ve unintentionally become an expert at moving on. Having lived in perhaps a dozen countries and had jobs with as many as 200 days of travel a year, I am keenly aware of the centrality of relationships. Living out of suitcase and having a rented apartment fully furnished by IKEA, they are all I have. They are my lifeblood. But sadly, I have also become far too practiced at needing to let them go.
Traveling so much and relocating so often, my life has been enriched by the people I know. So many nights alone in my hotel room, I wasn’t alone. I was writing, speaking, and despite the physical distance, connecting with my dear friends.
I’d arrange business trips or weekend travel so that I could meet them in some city somewhere in between. It was an effort that I would gladly expend, but I learned to see when that effort was no longer worth it, as difficult as that was to accept.
Here are the three simple signs that tell me when it’s time to move on:
1. When you need to plan and strategize how to present yourself
As life moves forward, we change. Our jobs, our looks, our economic situation, our habits, our interests—everything changes all the time. It’s the one constant in life.
As two peoples’ lives change simultaneously, gaps inevitably form between them. In a relationship that will stand the test of time, these gaps are bridged with each meeting. It’s the classic case of “We haven’t seen each other for five years, but when we met, it was like no time has passed!”
However, there are times when, with each meeting, the gaps get wider, and soon they’re more like gulfs. In these cases, we often spend time before the meeting fretting about how to explain, obfuscate, conceal, or excuse. Shame has crept in, and we feel like we can’t be ourselves. We’re either embarrassed of who we’ve become, or we suspect the “new” us somehow will not be acceptable to the other person.
I’ve put on too much weight—she’ll never like me this way. My career hasn’t taken the same trajectory as his. I got that divorce, while he has the same wife and now three kids. When the joy and anticipation you should feel when reuniting with someone is replaced by anxiety and inadequacy, that’s a really bad sign.
Of course, it could be all in your head. You don’t give up on the first go. You should make an effort to “be real” and lay it out there that things have changed. You might find it was a lot of worry about nothing. However, if your fears are confirmed and your efforts repeatedly result in awkwardness and shame because the other person rejects this new you, then it’s probably time to move on.
It’s important to understand that this is not a matter of blame. True love is knowing someone fully. It’s when two people become one but maintain their individual integrity. If you need to be someone else in order to get along, then you cannot be in a truly loving relationship.
2. When the relationship drains more energy than it gives
There is almost nothing more nourishing, refreshing, and perhaps even exhilarating than truly connecting with someone. All life is energy, and when someone opens up to you, they share their energy with you, and your share yours with them. Both parties are enriched.
That laugh you share with your old friend who calls unexpectedly. The warm feeling in your stomach when he smiles at you. The rush you get when she tells you she feels the same way about you. That is all our life force.
However, some relationships do just the opposite: they drain us. Our interactions with these people do not involve connection, but instead armoring up and deflection, and that requires energy.
What does this look like? It’s the stressful gaming out of what you’re going to say and how you’re going to say it in order to avoid conflict with that person. It’s the unease you feel when you learn that she’s going to be at that party. It’s the constant bickering with your boyfriend into which otherwise joyful occasions degenerate.
How does this feel? After being with the person, you feel tired, relieved to be away, or annoyed. Beforehand, you may feel nervous, low-energy, or simply like you’re going through the motions or doing your duty.
Two big caveats:
First, if this was a relationship that you considered important to begin with, this does not mean you give up on the first bad vibes. Of course you try and try and try again to make things work, but at a certain point the act of pushing the square peg in the round hole becomes too much. It’s just too draining.
A single negative interaction cannot be enough—in fact, an intense argument shows, if nothing else, that you care about what’s at stake in the relationship.
Second, this is not a recipe for selfishness. Getting energy does not equate with being the recipient of another person’s affections and generosity. In fact, quite the opposite: anyone who has loved knows how much better it feels to give than to receive; it’s a cliché that happens to be completely true.
And yet, if over time you are the only one giving, it starts to feel wrong. At some point you realize the person comes to you for help, not to share. A lasting relationship is inevitably one of mutual sharing and generosity. Anything else will start to wear.
3. When you’re the only one making the effort
I never thought I would need to face this topic, but today’s world of constant connecting without connection has given rise to a terrible new phenomenon—ghosting.
Always having access to a connected device, people can easily just switch to some other form of distraction when there is any negativity (or even effort) associated with reaching out or responding to another person. As our reach expands, our time in each other’s physical presence shrinks, and hence it’s now possible to erase people from our digital lives.
Now, it’s rare to be the recipient of a “hard” ghosting—to literally be blocked. To get to that point would involve a clear and unmistakable rupture in the relationship. However, “soft” ghosting—consistently not responding to messages in a timely manner or not at all, and opting for quick texts over thoughtful outreach and connection—this is something you’ve likely experienced.
Responses to your outreach become fewer and further between, and at some point you realize that you’re basically out of contact.
In these cases, the other person has either consciously chosen to focus on other things they deem more important, or they’ve gotten lost in the world of easy connecting. Or, they may simply have decided they no longer care to maintain the relationship and want to avoid the awkwardness of telling you.
As I began to encounter these painful situations some years back, my first instinct was action and confrontation.
I made an effort to increase my touchpoints with the person in question, invited him/her to dinners and other meetups if possible. When rebuffed (or more likely ignored), I got to a point where I directly conveyed my distress about where our relationship seemed to be heading and asked if he/she wanted to turn it around and what we could do the change the situation.
Never once was this route successful. If someone is moving on with his or her life, and there’s no more space for you, no amount of guilting, cajoling, passive aggression, or begging is going to turn it around. That person needs to value your relationship above the alternatives that constantly compete with all our time each second of every day. He or she needs to want to keep you as an important part of his or her life.
In these cases, the best you can do is reach out, but that outreach needs to taper off—pushing and insisting and pleading will only serve to create negative emotions and likely lead to conflict, or even worse, the person feeling the need to respond to you out of a sense of guilt or obligation. Your relationship lingers on and becomes more stilted and forced and loses its value.
In fact, in any of these cases—when you feel like you can’t be yourself, the relationship becomes draining, or you’ve been ghosted—it’s difficult not to generate a lot of emotional or actual drama. It’s a sad situation involving someone who at least was once very important in your life. You naturally want to fight for it, and you should, to a point.
But, like life itself, in relationships you have to learn to trust the flow. You can swim against the current for a little while, steer yourself this way and that, but in the end you cannot control the river. Instead of ratcheting up your response to the situation and effecting an emotional crescendo, do your best to reach out to your friend with honesty and compassion.
There will come a time when you know it’s not worth it any more. You will feel the negative emotional vibration in the form of resentment, frustration, fear, hopelessness, etc. At that point, however, you risk tainting even the good memories of your time with that person with the bitterness of the breakup. Rather than gratitude for the time you had together, you feel loss. You rob yourself of the relationship you had.
There is no way of knowing when to act, but in this case you’re not taking action, you’re letting go. The best way to know when to do that is to follow your instinct, and when your time being with and thinking about the person becomes a negative experience, that’s probably a good time.
The other benefit of letting go rather than fighting is that you allow space for a reckoning if the other person decides to reengage. And though that’s unlikely based on my own experience, it could happen someday.
After all, you rarely know the exact reasons and motivations for the other person’s behavior. Indeed, they’re often unknown even to the other person, and perhaps unknowable. So, one day you may find your phone ringing, and it’s your friend—people always retain the capacity to surprise you!
And as hard as it might be to imagine, there may be a good reason for the person’s behavior. You never really know the suffering they’re feeling, but if they’re letting go of a dear friendship, the least you can say is they’re not thinking clearly. Some other suffering is taking hold, and it’s your friend’s loss. Don’t make it a terrible loss for yourself too by creating a drama.
This is of course easier said than done, but if you stay conscious and draw on your compassion, you can do it.
Recently, a dear friend of ten years ghosted me. She and I had been through it all: moving countries, marriages, deaths, international travel—all the major life milestones.
A little over two years ago, she became more and more distant and less responsive. Not surprisingly, this coincided with her becoming much more active on social media and followed a period of tragedy in her life. I reached out repeatedly for about a year, but my efforts eventually led to total silence, and I let go. I haven’t heard from her in a year and a half.
The moment I knew it was time to let go was when I was tempted to write her something passive-aggressive. At that point I realized I was experiencing the relationship with negativity, which would inevitably come through in my communication with her.
I would be lying if I said it didn’t hurt, but more futile efforts would have hurt even more and put a possible future reconciliation at risk. I also needed to have the compassion to understand that she had recently gone through a tragic time, and undoubtedly that had an impact on her thinking, feelings, and behavior. I hope she’s alright and remain open to the possibility that one day she might come knocking on my virtual door.
But the truth was clear—it was time to let go.
About Joshua Kauffman
Joshua Kauffman is a recovering over-achiever and workaholic. Leaving behind a high-powered life in business, he has become a world traveler, aspiring coach, and entrepreneur of pretty things. Amateur author of a recent memoir Footprints Through The Desert, he is trying to find ways to share his awakening experience, particularly to those lost in the rat race like he was.
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