Should I Stay or Should I Go?

For so many people, this relationship quandary looms large, and the uncertainty can last a long time. Once we bond with someone, and create a life together (with or without kids), letting go can come with great difficulty and cost — even if the relationship is clearly not good for us. Leaving an unhappy relationship can take great courage; our fears and insecurities can easily sway us into staying for the wrong reasons.

At the same time, I believe that most long-term relationships that end, do so prematurely. Our human ego often tricks us into attributing our lack of fulfillment to something missing in the relationship or with our partner. The truth is we often don’t know how to create our own fulfillment, how to work through relationship challenges, which can leave us desperate to end a relationship for relief.  While objectively right or wrong decisions do not exist when it comes to ending a relationship, there are some guidelines I have found for gaining clarity on “what’s right for you.”


The following is a checklist, if you will, to inspire you to ask yourself some important questions — 7 about yourself, 7 about your partner/relationship.  This exploring process is to awaken awareness, action and personal growth — through which greater clarity will likely unfold. I draw these exploratory questions from my own marriage journey and my work with couples, which have both been profoundly enhanced by what I have learned about relationships from the wisdom of Kabbalah. I am grateful to share these thought- and soul-provoking questions with you.

CHECKLIST 1: YOURSELF.  Look no further for clarity until you’ve gained greater self awareness and worked on yourself. You can start by asking yourself the following:

  1. Have I put in effort — and in the right way? For a certain period of time, have I committed 100% to being more and more connected to my true self?  That is, being the kind of partner, friend and person I want to be. Have I explored what I need to change and where I need to grow — whether that be in growing my self confidence or authenticity, working on my anger or trust issues. Maybe I need to become more giving and less selfish, more appreciative and positive. Do I know how to set good boundaries for how I like to be treated.  Am I smiling at my partner regularly,  do I know his/her love language? Do I have trouble seeing the good, do I have a fear of confronting, of being abandoned, etc. You get the idea.  To the extent we put our focus on becoming who we want to be unconditionally, that is, regardless of what I get back from my partner, we elevate ourselves to a level of authentic visibility to see what’s best for us long term. This is how we “earn clarity”
  2. Have I done my research on relationships? Most of us grasp that we need to read books, study and learn in school, and for our professional lives.  We often completely overlook how important education and knowledge are when it comes to relationships. We come home from work and expect the relationship to run itself, to give to us what we need.  Without the effort of gaining knowledge, it’s like trying to navigate our relationship double blind folded, baffled by how hard it is to live and grow with those we love.
  3. Are my expectations balanced? Am I expecting too little, glossing over important red flags? Sometimes we settle for less out of fear of being alone or not feeling worthy of more.  On the other hand, am I expecting perfection?  Do I expect someone to make me happy, fulfill me unrealistically?  Most relationships have some kind of lack.  I know when I first married, I had an expectation that all my lack would be fulfilled. When this didn’t come to fruition (as no one can fill another’s lack to that degree), then I panicked and thought the problem was with who I had chosen.  Thank Heavens I did my due diligence and over many years came to learn that, before love could truly grow, I needed to start with creating my own happiness, fulfilling my own self and life.
  4. How Independent and fulfilled am I? When we are dependent on someone, we can’t make a clear decision about love.  Because it’s about need.  To what extent are you independent— emotionally, financially, spiritually and for your needs overall?  The more independent we become, along with putting effort into a relationship from a place of fulfillment, the more clarity you will gain.
  5. Do I know my purpose and goals? If we don’t know what direction we want to go in our lives, where we want to find meaning, then it’s harder to know who we want to share the journey with. Knowing our values and exploring our direction in life, as best as we can, serves as a compass for our own direction, personally and in our relationships.
  6. How clear am I on my relationship boundaries and criteria? Creating a clear sense of what works for you and what won’t work for you is a good start to seeing if your partner crosses the line with any of your deal breakers.  If you don’t know where you stand, then it’s harder to live an authentic life and make choices accordingly. A deal breaker might be related to alcohol or other addictions, or perhaps it’s about taking care of one’s health.  Maybe it’s about kids and being a family person.  For many, it can be about sharing a similar spiritual path.
  7. Have I tried counseling? We all have blind spots and areas of growth and learning we can’t do on our own.  Seeking help can illuminate the issues in your  uncertainty and help you gain clarity.


CHECKLIST 2: YOUR PARTNER/RELATIONSHIP.  Now is a good time to explore and take an honest look at how you feel about your partner and the relationship. To help you gain clarity, you can ask yourself:

  1. Is s/he worth the investment? All relationships take effort, some more than others.  Maybe it sounds harsh, but if someone in your life doesn’t feel worth the effort to you, then you might want to reconsider how much you invest. Maybe you don’t like putting in effort, so go back to the check yourself list.  But if you are willing to put in effort and you really value this person in your life, then this question might help you decide which direction you want to go.
  2. Does my relationship enhance or diminish the other important areas of my life? We have many important aspects of our lives, like our self care and health, our friends and career, family relationships, hobbies, charity, spirituality and sense of community. Do you feel supported and encouraged in these areas by your partner?  Do you feel that your relationship takes up or drains you in a way that takes away from these other areas? If you want to stay in the relationship but find this question to be a problem, explore whether there is there room in the relationship to make changes?
  3. Is my partner someone I trust, who I feel safe with to be my real self? Love can grow and grow only when we feel safe, when we can be vulnerable and authentic. In addition to the romantic aspect, the depth of the friendship is what many report as a most essential ingredient. 
  4. Do I like what I see now? It’s not recommended to move forward in a relationship thinking you can change someone.  Once we are in a long term relationship, sure, things we don’t like are going to surface. Maybe even big things.  We each need to decide to what extent we can accept and love the other person unconditionally, as they are.  We want to INFLUENCE, yes.  Gradually over the years to help each other grow.  But we don’t want to go in with a mindset to CHANGE anyone.
  5. Do our values and/or spirituality align? For long term fulfillment, a strong affinity with one’s values and the way we view life, can make a significant difference in how deeply we can connect and grow together.
  6. Is this someone with whom I can grow, who also wants to grow, and who I think can help me become a better and better version of myself? Does s/he welcome change and feedback, even if initially defensive.  Are they open to counseling and to learning about how to be a better person.  Can they admit when they are wrong or have made a mistake. “Love means never having to say you’re sorry” might be a great line from the movie Love Story, but in the real world, owning and taking accountability are key for long term love to grow.
  7. Does my partner seem ready for a relationship? To what degree is s/he happy within, ready to give, secure and trustworthy.  We can give all we have to a relationship but when we are taking the lone soldier approach, this can create a cycle of endless frustration.  We also want to look out for whether our partner depends too much on us for their happiness or security.  Not that we have to be a final product of mental health and wholeness, but a person’s sense of emotional and spiritual maturity, and security in attachments, can make a significant impact on sustaining a balanced and healthy bond