When to Hold ‘Em, When to Fold ‘Em: Should I Face this Challenge or Should I Let Go?


There’s nothing more rewarding than walking away from an unhealthy situation… aside from the overwhelming sense of quiet exultation you feel after sticking through something challenging that really matters. The question: “Should I stay, or should I let go?”

Lord is it harder to carry on? Or to know when you are done?” -Joanna Newsom

Everyone knows that personal growth is spawned by rising to meet challenges, and nurtured through the self-discipline of commitment. However, no one ever told me how to tell a hurdle from a road block.

Nothing is more devastating than staying in a harmful situation… aside from giving up on an opportunity for growth by choosing not to stick it out in an uncomfortable but very important situation to you.

But … how do we know the difference between what is a life challenge, meant to be overcome, versus a depleting situation that is simply getting the better of us (without giving us anything formidable in return)?

In order to grow into your unique self and offer the world your unique gifts—you must choose with great particularity where you devote your time and energy. We all turn into the shape of what we lean into. (I have developed a program on how to get into your ideal body by inner growth & developing your senses around what’s right for you physically – you can get my free holistic health workshop here)

We all must choose with great particularity where we devote time & energy; we all turn into the shape of what we lean into. Click To Tweet

Whether it’s professional/school situations, community connections, friend relationships or partnerships—there will come times when you’ll be challenged, made to feel uncomfortable, and if you choose wisely, the sky is literally the limit to what you can achieve. You can do literally anything you truly want if you devote your energy to it; ultimately every single dream you have (that is really, true-ly your dream) is your destiny. All you have to do is listen deeply to the path inside you. You’ve got the map. But every great adventurer still needs a key.

Most people I know struggle with what to hold onto and what to let go of. I did too! Because the messages we receive are from such an imperfect world. [Rant alert!] The cultural programming we receive is not just ‘imperfect’ like an apple with a bruise, it’s downright toxic—like an apple covered in DDT genetically modified to destroy itself and its lineage by failing to produce seeds so that the literal devil can monopolize on your hunger: that’s the kind of imperfect we are raised in and what we are now up against within ourselves. But the map inside is clear, with just a little guidance and a key. So how do we know when to hold ‘em and when to fold ‘em? Here are the keys!

Q #1: Should I Let Go? Is This a Deal Breaker?

This is the question you will always come back to: is the challenge I am facing a deal-breaker for the situation I am in. The tricky part is… we all have very different thresholds for different kinds of rewards and punishments. What is absolutely a deal-breaker to your friend won’t be the same for you, and what someone else could easily grow through, you may feel is torture.

Example: The well-meaning loved one.

I had a friend who spent 7 years telling her sister to leave this jerk-of-a-man she was dating. The day her sister & this man got married, he turned into husband-of-the-year and has persisted in his exemplary fatherhood and partnership to her: he was severely traumatized by insecurity, her sister somehow understood he was worth it deep down, all he needed was to feel poignantly secure for them to grow into coupledom goals. Obviously my friend had no idea what this man was made of, and could only see through her personal lens, but she wasn’t the one meant to marry him—her sister was the unique personality meant for him—and she had no idea what kind of detrimental advice she was giving though she earnestly wanted t help with her whole heart.

Step 1. Listen Closely to Yourself

Pro Tip: Keep what’s most important to you safe. Not only is this a better plan to achieve goals, it allows you to choose your vulnerabilities wisely. There are many things that others just don’t need to know in order to love & support you. Oftentimes the greatest challenges we go through are going to be ours and ours alone—we may share them with people in many ways, but be wary of conversations about the most important things to you: keep them for people you really trust. If someone will just listen and hold space for you, this is ideal. If you know they’re going to tell you their opinion on what you need to do about your situation—run. This is your life, no one else is you, and you will only get to the best you by listening to the best you (that person is very deep down and is incredibly unique).

Q #2: Should I Let Go? Do I Have a Role to Play in this Discomfort?

OK, you’ll always have a role to play. A challenge won’t come into your life without you having a role in it. Own that. But ask yourself what kind of role is it? Sometimes unacceptable situations come into your life so you can draw and define a boundary. If you’re not ok with something, it either needs to change or it needs to detach from your life. All we need is to learn to tell the difference.

Can you identify areas in yourself that you would like to develop that are being triggered by the situation? Do you feel inflamed by it when you’re emotional, but then understand how you need to take responsibility for your part once you are rational? Or is it the other way around, you feel like holding on when you are emotional, but know that isn’t the right decision for you once you’ve regained level-headedness? Normally your rational, at peace, self will have the better indication of whether or not this is a growing experience or a lesson in boundaries.

Example: The self-destructive friend you feel sorry for.

I had a friend who really liked to hook up with men in relationships. She didn’t just choose men who were taken either, she chose men who were in solid, longterm, often domestic partnerships and even marriages. She had issues with codependency and claimed that, in her eyes, these guys—ironically—seemed like the ones who would commit to her. She would go out of her way to come on to these men in ways she would never be capable of with any other type of man. Sending love notes across bars scantily clad, creating years of ‘friendship’ until she finally drove a stake in a relationship, even taking language courses with one & bringing sexual topics into the training! She failed much of the time, and sometimes she succeeded. I was there for her, though I had absolutely no respect for her targeting men in relationships (and had no idea why she’d want one who would cheat anyways), but I supported her because I thought I loved her. I thought she was too innocent and naïve, always hurting herself because she was too trusting. [Spoiler alert]: this is never the case in a grown-up.

At one point she was in a really unhealthy relationship that turned her depressed all of the time. I tried to be supportive, but it was painful just to be around her. She’d say horrible things. She didn’t hear anything I said about the way she was acting and how obviously unhappy she was. She just kept taking the ogre path and being almost menacing in her disdain for everything (including anything I was doing). I was facing my challenges head on and growing as an individual capable of Real Love and support. And she wasn’t—she was in an extremely unhealthy codependent relationship she defended. We’d been the absolute closest of friends. All of the sudden I didn’t matter to her. It became clear to me what we’d been: some issues of mine were being supported by issues of hers. Mine were dissolving. She no longer needed my support because she had another codependent relationship to be in, and I wasn’t very dependent on her anymore because I was coming into myself!

Step 2. Be Honest with Yourself

I initially had a role to play in the relationship, in the discomfort of being there with her while she did things I don’t agree with on a fundamental level, then all of a sudden my role was gone. I’d owned the experiences I was going through and grew out of our relationship. My heart hurt to leave, and I even tried to make amends, but she didn’t care. You will always get confirmation you did the right thing in walking away or staying, this was mine. And I know in my heart this is definitely not someone I would want in the kind of life I am trying to create.

Related: 10 Ways Women Self-Sabotage

Q #3: Should I Let Go? Is it Developing, or is it Stagnant?

Are you beating your head against a wall? Or does the discomfort change? If it changes, even a bit, it means you are climbing. This is an excellent indicator of growth. If it is stagnant, you are having the same bad feeling every time you go into work, you’re having the same argument with your partner over and over which goes nowhere, your friend just keeps on doing the same self-harming (or you-harming) thing again and again: this is a pretty good indicator you are done. If you are not developing, you are stuck.

Step 3. Be Committed to Growing

Even tiny gains mean you and the situation are in it together. You’re growing and feeding each other. If you feel stuck and trapped, it is holding you back.

Related: Do You First, Give Second (You’ll have More)

Q #4: Should I Let Go? Is it Taking More than it is Giving?

This isn’t to say that everyone and everything has to give you back what you put in, but there should be an exchange going on. We don’t really need to receive the exact things we can could readily give, so the exchange is sometimes a bit cryptic—but it should be a cycle of whatever caring means to each person involved and it should be understood as such between all parties at least at some level. Love, support, nurturance and even space holding are things everyone does differently. You probably don’t need the same kind of support that you can offer. And you don’t need what everyone has: some situations are just not going to feed you, some situations you will not have the right food to feed. Knowing when to keep giving or to step away has a lot to do with whether you are gaining by what you are giving.

If an equitable exchange is taking place, it will most likely feel like you are getting more than you are giving, because we give unconsciously, and that is a beautiful situation to be in! You can then give more and more and more and receive more and more back! Ideally, the energy transforms as you give and take between yourself and the situation, people and places will transform it and share it back with you in a cyclical pattern that feeds everything effortlessly. That’s the key to abundance. In this situation, your growth is exponential and you feel energized by plugging through even a fiery vista—because you are feeding fuel to the fire of alchemy—if you are drained and feel ‘burnt’ you may be putting your self in the fire instead of your fuel! Even if this euphoric give-and-take situation isn’t your immediate reality (compost is also fertilizer and not all growth is roses; roots and branches and leaves are also necessary), you should feel a sense of strength or benefit by plugging along with the challenges.

Example: The longtime friend

I had a sort of life-long friend who was the sweetest, softest, gentlest person. It always seemed like the world pummelled her for her vulnerability. She couldn’t seem to win. She always fell in love with the wrong guy (another girl who went after taken men) and always told someone the wrong thing which made others mad at her (she’d spill their secrets they entrusted to her). Even when she went into a helping profession, she thought it futile as everyone she tried to help was so far gone she made no impact. I’d always had sympathy for her and stood firmly in her court. She came to visit me and she was, of course, in the midst of another enormous drama where, according to her, she’d fallen ‘victim’ to a cruel world and community her were coming down on her because she’d innocently fallen in the trappings of something evil.

I was with her, I held space, I told her she was a good person. But in my adulthood, I started to sense something was wrong with the story—she’d been telling it since we were kids. She’d, once again, got herself into a sort of love triangle I didn’t respect. This time she’d done so with a bonafidely dangerous man. She’d even put her career, helping people, in jeopardy by being involved with this person (he was a violent, convicted felon—she works with children). She’d risked friendships, her chosen career (she studied 8 years for) and her personal safety for a fling. Again!

In my adulthood I realized that in the midst of all of this, she didn’t care about what was important to me at all.

She was spending time with me, but not showing up for any of it. She’d come to get my sympathy, and be tour-guided around my incredible home, but she hadn’t asked me about my business, my travels—nothing. I felt drained after the days we spent together. I found myself at home almost in tears at the end of our day, holding my cat because something was so hurtful about the situation. That’s when I knew: this wasn’t right for me. Something was really, really not right with our relationship. I looked back to all of the years we’d known each other and saw a pattern: every time she’d been down-trodden, every time the world seemed to be so cruel to her, she’d done something really wrong. She always claimed innocence, not knowing or understanding what she did would be harmful, but there was no way she didn’t know exactly what she was doing. She was not innocent and she never was—she was doing horrible things to people and never taking responsibility.

Step 4. Seek Sustainability—Always, and Be Brave to Balance Your Life Energy

I’d forgiven her in childhood, for her innocence, but in my adulthood I realized that she was extremely self-serving & short-sighted in her actions which caused other people needless harm. So, the next day I confronted her. I told her I felt like a tour guide and she hadn’t asked me anything about my life. You can imagine, she turned on her trusty tears and acted as if I was now the cruel hard person who was being so terribly mean to her. But all I felt was relief—it felt amazing to say something! A few weeks later this longtime friend blocked me on social media—for telling her she treated me like a tour guide—and it served to say that she definitely was never a soft, gentle or even mildly considerate (!) person, and I’d absolutely done the right thing. You will always get a confirmation on your choice! If the situation doesn’t change, it’s up to you to change it.

4 Questions that help you answer "should I hold on or should I let go"

Is it a Deal Breaker? “Should I let go?” Only You Can See and Decide the Answers to these Questions.

If you decide to hold on, perhaps these Spring Rituals will help breathe new breath into the situation. Or choose Summer-time healthy lifestyle changes.

If you decide to let go, try these Mercury Retrograde practices to turn a crappy situation to your favour.

Should I Stay or Should I Let Go?

Only you can know. Is it a situation like the jerky-boyfriend who needed to climb the mountain of support to feel contented, finally, in the safety and security of his wife’s commitment to become a happy, healthy husband & father? Is your profession or school pushing you and needing more grunt work from you to ascend the incline of personal growth towards your absolute highest potential before you get the rockstar status and freedom of being an expert in your field? Or are you in a situation where you are maybe being taken advantage of or you’ve simply grown out of? Only you can decide. If it is in your life, then it is it for a reason. You have all of the agency in the world and it will call to you, again & again, to make the decision of whether to grow in the discomfort of challenge or place a firm and secure boundary between you and what you feel is not right. I wish you all the best!

Pro Insight: the opening quote is a song Newsom wrote about her and, her now husband, Andy Samberg’s breakup back in the earlier part of this decade. She knew to hold ’em.

Peace & so much LL.

Use this tool to tell whether you should hold on or let go of any given situation.


  1. Marisa

    This is such a well-written post that deserves recognition! Love it <3

    1. Laura-Lee

      Thanks girl! I appreciate the love.

  2. Rawlings

    I love your ideas. Thanks for the post. This is a more realistic way

    1. Laura-Lee

      Thanks for your support.

  3. Emma

    Great post. Sometimes you have to evaluate whether something is with staying for it not. Love the example of the woman who stayed and worked it out and got a good man out of it

    1. Laura-Lee

      Abso-fruitly. Value is so super personal, eh??

  4. Mikayla

    Great encouraging post!

  5. Sarah | Diamonds N' Denim

    I love this! I think at some point or another, we’ve all run into, or developed a friendship with one of your mentioned girls- the well meaning sister, the self destructive woman, and the self serving friend. Having long time relationships, or simply feeling pity for these people, are not good reasons to stick around, but boy is it sure difficult to make that cut! I can’t help but wonder just how many precious hours of my own life I’ve wasted by trying to “bring everyone with me”. Thank you so much for sharing this post with us, it’s such an eye opener!

    1. Laura-Lee

      I’m so glad you got so much from it – that was totally my intention! We’re taught so wholly (especially as women) to keep relationships together and ‘make everyone happy’. Now we’re all expected to ‘kick anyone ot the curb’ if they displease us, and it’s just so hard to navigate what we actually should do (for the best of us, specifically)!

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