Lessons from Heartbreak


I am recovering from a breakup with a love of my life. Late January marked the end of a long, and, at times, tumultuous relationship with a woman I loved immensely, and was completely emotionally naked with. She truly meant the world to me. The recent bookend to our love story has been particularly rough.

We’ve all been there. Once a long-term romance is called off, pain inevitably ensues. There’s more than just emotional suffering and mental anguish. There’s a physicality to every breakup. The connective tissue that once held the relationship together is severed and rips a void in the pit of your stomach that feels permanent and irreparable. It feels like a part of your abdomen was ripped out. You’re left wondering if you can ever give yourself fully to a relationship again.  

I’ll be honest: it’s been massively hard. I’ve made it through by giving myself space for things like reflection and sadness. A steady dose of yoga, introspective beach walks, meditation and therapy have helped. And good cries over BB King songs :).  

 I’ve taken a lot of time to myself to mourn the failed relationship and figure out what I can draw from it. Lessons need to emerge out of the sadness; learnings I’ll be able to take with me as I move forward. I wanted to learn as much as possible for the sake of my next relationship, so I dug in. I looked back at this recent breakup and those before it and I tried to distill the best insights from past heartache.

 Here are a few of these lessons.

 I can actually take on too much responsibility.   

“What?!” you say. “Isn’t it good to take responsibility for your actions?” Haven’t we been all taught to do so from a very young age?  And for good reason?   

Yes, these early learnings are in large part incredibly valuable to teach you responsibility.  In a failed relationship, I have learned there is plenty of blame and accountability to spread around. To both parties. When grieving a past relationship, it’s very easy to slip into internal torment of the form “What could I have done differently?”  

 One thing I’ve found works well to overcome this issue is to do the parsing exercise of what was on my significant other and what was on me. Be very deliberate. If you need to write things down, so you can see the items before you, don’t hesitate to pull out a pen and paper. Draw a line down the center of the page and start writing the things you take ownership for, and those that should go to your former significant other.   

This will accomplish several things.   

One, it will enable you to take responsibility for the problems you created in the union. You’ll have those to work on between this relationship and into the next one. Two, you will have a set of things that are not “on you” but on your former lover. You’ll notice that there were things you had very little control over, and that the relationship ended for reasons that didn’t fall on your side of the ledger. In the final accounting, you’ll start seeing that it did take two to tango.  And that you were not entirely responsible for the overall health or the ultimate failure of the relationship.

 Don’t ignore the red flags.  

There’s the old saying: Love is blind. It is. Without a doubt. Particularly in the honeymoon phase.  The pheromones take hold and we’re smitten with our new partner. He/she can do no wrong. Our minds and body have been taken over, and all you can think about is your lover. It’s a beautiful thing. Yet, the trick is keeping up our awareness while in this love fog. Not doing so puts us at risk of missing any red flags. That means keeping tabs of your feelings, moods or emotions as you start the relationship. Think of your feelings as your navigation system; internal signals telling you things that your mind hasn’t yet fully wrapped itself around.  

 If you’re feeling anxiety in the initial stages of a relationship, for example, ask yourself why this is showing up for you. Dig a bit deeper. What is the root cause of my feeling unsettled? What are my feelings telling me? As you start unpacking, you’ll land on nuggets that will prove very beneficial. Maybe your partner isn’t opening up to you as much as you would like, or perhaps not showing up for you. These are things you can now discuss and work on with your lover in an effort to grow closer. 

In reflective moments after a relationship has ended, I have looked back only to realize that there were warning signs I had decided to completely ignore. My head was buried in the sand and savoring young love. The sooner I am able to identify the red flags, the faster I can address them. That’s only possible if I keep my emotional radar activated so as to not lose sight of my true North.  

 Don’t blame your partner for their blind spots.  

This applies to all relationships, amorous and otherwise. Until you’ve told someone something, the assumption should be that it is out of their awareness and can’t be changed. Your responsibility is to communicate that to them calmly and concisely. If they don’t respond, once you’ve brought the issue to their awareness, then you’ve got a gripe to hold onto. But unless you’ve done your part to bring something up, you shouldn’t expect them to change their behavior.  Because they may not know any better.   

Humans are inherently limited.  

This might seem like an obvious one, but it is the hardest lesson I’ve had to take in the past couple of years. Not only in the personal realm but in the professional realm as well. It’s one belief I had refused to live by for a long time — I’d like to think all of us are capable of improving and forging ahead — but I’ve had to accept that even if you communicate your needs to your significant other, there is no guarantee they can actually fulfill them.   

You realize the person you’re with will continue to fall short, because they don’t presently have the capacity to fulfill your needs and your aspirations for the relationship. 

It’s a rough assertion to come to terms with. But it’s also the most liberating thing, if you’re completely able to process it. It will set you free.

In my most recent relationship, I kept thinking certain things would change in my partner. I held onto the belief that certain traits were aspects that could be worked on and worked out through sheer will and determination. But that was my own personal paradigm; a view I was projecting onto my partner and the relationship. I came to the hard conclusion that I did not control all of the variables, nor could I affect all of the change I was desperately looking for.    

Love will reveal who you are.

The great thing about falling in love is that each relationship will teach you a whole lot about yourself. True love makes you incredibly vulnerable.  

It’s like standing in front of a full-sized mirror completely naked. You get a clear reflection of who you are as a partner. You’re able to discern your soft spots, your weaknesses and your calloused edges. Each union imparts additional self-knowledge. Each new lover gives you a new reflection of yourself and prompts you to grow.  

As you get more acquainted with your needs, you grow more finely attuned to those that will fulfill them. You’ll get back out on the dating scene with a more refined sense of who might be your ideal mate.  

 Your tastes will evolve.  

You might have liked the sizzle and forgotten about the steak. Next time around, you’ll make sure there is substance to your love. You might have fallen for the alpha chick, only to realize that she not might have been the ideal partner in raising children. Or maybe it was the bad boy who was exciting but couldn’t provide you with any stability. All of these realizations come from confronting yourself to a new relationship and to your needs. If you are to look back at your relationship history, you are sure to find an evolution in tastes. You’ve tried people on for size. As you grow older and acquire self-knowledge, you are more likely to find someone that fits snuggly to your needs.

Anger is healthy to hold onto (in the beginning).  

We’re often told that anger can be toxic. That it can eat at you. That it will hold back. It’s often demonized as a source of violence or torment. Anger is also a powerful force. It is an emotion that makes you feel in control. In the driver’s seat. One of the issues we all face when trying to leave a relationship is that we’re held back by its gravity. We’re still entangled by the attachment we have with our partner. Anger, during separation, plays the important role of catalyst.  

Think of anger as the spare rockets on the space shuttle and your relationship as Planet Earth.  The rockets are critical to get you disentangled from your attachment and into orbit.  But, in the end, once clearly separated from the planet and in outer space, the goal is to drop your spare rockets in order to achieve control and serenity. Ideally, you want to be able to look back at your relationship and your ex with tenderness and empathy. Just as you might look back at Planet Earth from the space shuttle and admire its sheer beauty.


                                                                                                              Spare Rockets Pic  


Remorse over regrets.   

The French have the following saying, “It’s better to live with remorse than with regrets.” One of the hardest things to deal with in love is knowing that you didn’t quite give it your all, or that you could have done things differently. Unfinished business can gnaw at you, as you think back to “what could have been” in a relationship where you believe you could have given more.  

I have found that with some relationships, it’s important (if not critical) to burn through them entirely. Till the bitter end.  

In my recent relationship, I had a vision for a beautiful place we could get to, yet I didn’t quite think we had done everything in our power to get there. I wanted to know that I had left it all out on the floor and exhausted every possible avenue. If the relationship doesn’t pan out, what you’re essentially doing is buying yourself future peace of mind, and eliminating regret from the equation. And that’s worth hours of sleep and tranquility that breakups have the power to steal from us.   

Past relationships are lifelong assets.   

There has to be a bright side to how catastrophic breakups feel to us. The silver lining, I’ve found, is that failed relationships are lifelong assets. I’ll be able to look back at each individual relationship as I continue to go through life and keep drawing lessons from it. 

Interestingly enough, the more painful the relationship, the richer it will be in lessons. Several years ago, I had a 3.5 year relationship with a lovely woman to whom I could have gotten engaged. We ended up separating after living together for over 18 months. It felt like a mini divorce, as we disassembled our life together and moved out of our shared one bedroom in San Francisco’s marina district. I was initially destroyed and it took me close to a year to recover. But this one relationship has been a treasure trove of lessons when it comes to my love life. The learning’s keep on coming over 4 years after our separation.  

First, I came to realize that I didn’t see myself evolving with her long term. I’m now convinced that our paths would have diverged over time. It wasn’t till years later that this nugget emerged and that I was able to articulate it. When we separated, I wasn’t fully aware that our likely evolution would have us grow apart. 

Second, I needed someone that was willing to work hard on a relationship. I had offered to seek some outside help when our relationship was falling apart, and she had refused. I came to realize that I couldn’t be with someone that wasn’t willing put in the hard yards for a relationship. Over several decades of marriage, bumps in the road are sure to come up. I became acutely aware I needed to believe that the person I was with could be my partner, roll up their sleeves, and weather the tough times side by side with me. 

Next time you think you’ve hit rock bottom, as you’re trying to pull yourself together post-breakup, try to remind yourself that the journey you just went through will provide you with some invaluable gems of insight. It may feel like small consolation at the time, but as you heal, and later on, as you look back, you’ll realize that everything you just went through — if carefully examined — will prepare you for your next romantic endeavor.