When All In Failed: Navigating Entrepreneurial Setbacks

As entrepreneurs, we often go 'all in' on our ventures. But what happens when it fails?

Have you ever gone “all in” on something… and failed?

Part of having an entrepreneurial spirit is giving things your all, but the dark side of that is… 

Sometimes, it doesn’t work.

And what do you do then?

I recently spoke with a client who – despite being very successful, having built multiple companies, and done extraordinarily well for himself – was still carrying shame around failing a company that he’d put his heart and soul in.

This brought with it so much grief and heartbreak… literal trauma that had impacted him on a nervous system level…

After we’d gone through the somatic processing, he shared with me that he’d lost trust in himself, and how could he possibly go “all in” on anything again after that burn?

It feels important to share what we uncovered, because I’ve seen variations of this with SO many people I’ve worked with…

The biggest mistake he’d made was not going all in, as he was wrongly punishing himself for.

👉🏼 The biggest mistake was tying his sense of self-worth and identity to his company.

We do this SO much…

With money, with our romantic relationships, with our business…

We go all in, but with ATTACHMENT, and THAT is what creates the suffering if the venture fails.

Not only that, but we proceed to create a STORY about why that venture failed.

… And if we are tying it to our self-worth, then chances are, this story will make it mean something about us.

In the case of this client, and many others I’ve supported through this, the story will be about how they failed, how they’re not as good as they thought, and other self-sabotaging narratives that don’t serve them.

As I shared with him, the anti-dote is self-compassion.

More practically, it’s CHANGING THE STORY you’re telling yourself about WHY that relationship, business, financial venture didn’t work.

My client’s biggest realization, however, was realizing that going “all in” on something again without enduring the catastrophic consequences of failing WAS possible…

If he approaches it from attachment.

Going “all in” without being attached can look like:

– Giving your 100% to a client, without needing them to follow your advice for you to feel successful

– Giving your 100% to your children, without expecting them to turn out the way you think they should

– Giving your 100% to your business, without it needing to validate your value

The key is: don’t tie your sense of worth to a company, a cause, a person, or anything that is outside of you. This is a recipe for disaster.

When you self-source your self-worth and validation, it sets you free to create your reality in an entirely new way… not based off of stories of the past, but actively co-creating your story of the future with the Universe.

THAT is something worth going “all in” for.

Do you relate? Would love to hear about your experience. Share in the comments!

p.s. If you’ve been holding yourself back from going all in and are ready to transform your story this year – you’ll want to start with a Story Clarity Intensive. Such a potent and game-changing experience.

Hey, I’M CELINNE DA COSTA!

I'm a Master Coach and storytelling expert for CEOs, executives, and leaders. My work has been featured internationally in Forbes, Entrepreneur, Business Insider, TEDx, and more. I specialize in helping high-achieving visionaries unlock their most powerful stories, build influential brands, and grow their impact, all while staying true to their core purpose.

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