What Happens When You’ve Tried Your Best - And It’s Still Not Good Enough
For those of you who are passionate and empathetic—especially if you find yourself wondering whether it’s time to let go or if you just haven’t done enough—this is for you. And to those who’ve made the difficult, courageous decision to keep working or to move forward, congrats. I hope this will give you some comfort, validation, and a guide for what’s to come.
There’s a particular kind of heartbreak that comes when you’ve tried your very best, and it still doesn’t work out. When you’ve shown up, again and again, hoping your care, effort, or commitment might be enough to turn things around.
A year ago, I closed down a nonprofit I co-founded and ran for nearly a decade. It was a decision full of relief, exhaustion, resentment, and everything in between. In writing this, I want to share what I learned from finally letting go— and speak to anyone standing in that uncertain place, unsure if it’s time to keep holding on or finally let go.
A little background about my story
In 2014, a classmate from my art therapy program and I started a non-profit organization to offer affordable mental health services through art therapy. We both deeply believed in the power of creative expression, especially for people with lower incomes, as mental health access is financially limited. So fresh off finishing our art therapy education, we went for it. It started with some volunteer work, and finally, we established our own physical space in 2018.
All this came to an end in 2024. I was burned out from trying so hard to make the mission and the partnership work. I needed time to rest and had to narrow the focus of my mental energy to just my family, my partner, my cat, my clients, and my closest friends.
Leading up to it…
Letting go didn’t happen all at once. There were signs—small gut feelings, moments of deep exhaustion, growing resentment—but I brushed them aside. There always seems to be something I can try, and I always had hope that things might be better once this and that are done.
But then I remind myself to widen my lens, and started thinking more for myself. Is this what I want for my life? Is this the version of me that I want my partner, family, friends, and myself to know me as? Is this how I want to spend my time and energy (the constant struggle of making it work)? And I heard the clear no.
What may have been happening beneath the surface? Why are we holding on so tight?
Too attached to an old identity
We become deeply attached to the narrative of how we see ourselves: the go-getter, the leader, the fixer, the one who can keep pushing. That narrative has helped us through so much of our lives, so we tend to rely on it when things get tough. It can be hard to let it go, even when it no longer serves our purpose.
For me, that identity was being resourceful—someone who could always figure it out and someone who could always take the stress or challenge. I kept thinking, "I can handle it!” And because I could always see another possibility, another angle, I kept going. I’ve developed different skills to help me manage stress, so I thought, "I’ll be fine!"
Only in hindsight can I see: I’ve crossed my boundary a while back.
Afraid of what giving up or walking away will say about us
There are a lot of negative connotations associated with giving up. It feels like you’re weak or incapable of making it work. With that, there’s also worry of how we’ll associate with ourselves from now on- ‘Am I someone who can’t make things work when it gets hard?. Will I be able to make something else work? And what will others think of me?’
Blurred the line between determination and alignment
We’ve all heard that - ‘to succeed, we need to try and try’; ‘Most successful people have grit and they keep pushing through’! But to what end? When we’re so in the thick of it, it can be tough to slow things down to think about how this job/relationship/role serves you on a bigger scale. Does it align with our goals and values in life? Is this how you want to achieve it?
Our mission was so unmistakable and unquestionable in relation to my values and goals that it was hard to slow down and question whether this was the way I wanted to achieve it.
Uncomfortable with change
Change in whichever direction can be scary. It is within our very human instinct that we seek safety. And even when things are not working, the familiarity will almost always feel safer than the unknown of what’s to come. So we stay. Even if it is bad, we know how bad it is, and we have already adapted.
We have already invested so much, and what if it starts working out soon?
It’s hard to let go when we have already put in so much. We then question, what did we invest all this time and effort for?
And of course, wishful thinking that it will work soon. We usually see that our effort should be directly proportional to the level of success we have. Even when past evidence suggests that the chances of success are slim, or it’s unlikely that you’ll get what you need from this relationship, we still hold onto the hope that it will work with more effort. That hope is easier to rely on than the daunting feeling of starting afresh.
We don’t want to hurt others involved and take on the responsibilities of their well-being.
For those of you who are still contemplating:
I want to first assure you that all the reasons you have are valid. Try to be compassionate with yourself and not be too hard on yourself about ‘still being here’, or ‘still don’t know what to do’. It’s ok. You’re just in a very delicate spot, with a lot going through your mind.
At this stage, I invite you to pause and reflect on these questions:
How do I want to see myself?
If nothing changed, can I accept this as my reality?
What’s the most important thing in my life right now? Are you prioritizing that?
The choice may not be so clear at this point, but you can feel a gnawing at the back of your mind, just pushing and pushing. You may not be doing anything on the surface, but trust that your body and mind are taking notes.
Sometimes, the small gnawing from our internal voice is not enough. We need that external push (usually when the situation has gone too far) to give us that strong validation to make that difficult choice. Suppose that’s the case for you; there is no judgment here. And if you are doing that, I encourage you to be transparent and honest with yourself. Don’t pretend you’re not just waiting for things to worsen to get that external push; try honouring your feelings.
This will help save time and mental energy in our push-and-pull inner dialogue, and most importantly, it allows you to make space to acknowledge your own needs. Allow yourself to observe and name what you genuinely feel or need without the pressure to act on it immediately.
How do you know that it’s time to let go?
It may not be crystal clear, but here are some signs you can look out for:
You start fantasizing about something going wrong so that you wouldn’t have to be the one to end it
You feel more drained than energized, especially around “the problem.”
You catch yourself starting sentences with “But I have to…”
You keep having the same conversation with yourself (or others)
The thought of letting go brings relief, even if it’s quickly followed by guilt
You’re no longer showing up as the version of yourself you want to be
If any of these resonate, it doesn’t mean you have to take action immediately. But it’s worth sitting with them honestly. Not everything we start needs to be completed in the way we imagined. And letting go doesn’t mean you’ve failed — it might just mean you’re finally listening to yourself.
For Those Who’ve Decided to Move On
Congrats on making this very tough decision. Endings can bring a mix of emotions. You might feel lighter, relieved, angry, lost, or sad, and it can be very confusing, as many of these feelings seem contradictory. Your mind might experience a lot of back-and-forth inner dialogue—that’s normal.
Here are a few things to keep in mind as you move forward:
Let the emotions come
Give yourself space to feel and care for your emotions. It’s essential to honour and listen to yourself. You can try free journaling, sharing your experiences and feelings with friends, expressing yourself through art, and other creative outlets. If the emotions feel too overwhelming, this might be a good time to seek a therapist to help guide you through them.
Rest — deeply
Your system likely needs a break from the mental strain of making decisions. You might not even realize how tired you were until you stop. Allow yourself to slow down and consciously plan more than usual resting time. And try not to rush into the next thing.
Practice gratitude, gently
Not to romanticize what didn’t work, but to honour what it gave you — skills, experiences, connections, and clarity. Switching your perspective to gratitude may help you see some unexpected things you gain from this experience.
Reconnect with yourself
When you’ve been living in constant effort or emotional entanglement, it’s easy to lose sight of who you are outside of that role, job, or relationship. Spend time with what nourishes you. This can help rebuild self-trust in your own pace and intuition.
Meet yourself with compassion
Your inner critic is likely to show up, to remind you of what you should’ve done differently or sooner. Try to meet it with kindness. It will take some repetition to remind yourself that you did what you could with what you knew at the time. That’s more than enough.
Find ways to build self-trust and confidence
You’ve probably taken a hit on your self-confidence and are not sure if you can trust yourself to make good decisions. So try to find some ways to help you regain some of that trust and confidence. Complete a project you never got around to, take the class you wanted to, etc. I participated in my first triathlon.
What I’ve Learned Through Letting Go
It’s been a year now, and looking back, I can say that I gave it my all. I stayed for as long as I needed to. I tried everything I could.
There are still moments when my inner critic will pop up, saying, ‘You should’ve done it sooner. You saw the signs.
But thankfully, a more compassionate voice has grown louder too — the one that reminds me that, ‘You moved at the pace you needed. It’s ok that I took some time before reaching this decision, as it was an essential part of you. It’s all part of the process of listening to yourself.’
Letting go has taught me how to trust myself again, to put my well-being before what others might think. It taught me to slow down and notice when something is misaligned, and to honour that knowing, even if it disrupts the peace.
If you're in the thick of it right now — wondering if it’s time, wondering what comes next — just know this:
This is part of the process of growth. You didn’t do anything wrong for getting into this situation or for however long or short you stayed. Whatever happens does not define your worth or who you are. You still have plenty of time. Your care, effort, and willingness to show up still matter, even if it didn’t lead to the outcome you hoped for. And who knows what this experience is setting you up for in the future?
