Nothing really prepares you for that gut-punch moment of disappointment when you really thought it would work out this time, and it turns out, it didn’t. And when one disappointment turns into a string of them, they weigh heavier and heavier.

Chronic disappointment becomes its own form of grief.

In those moments, it’s hard not to wonder… is something wrong with me?

“Why am I not good enough?”

“Why can’t I figure this out?”

“Why can’t I get it together?

Some of the deepest tears I’ve ever cried came in moments like these. The tears were more from a sense of futility than from the disappointments themselves. I didn’t just feel sad, I felt shame. I felt like the way forward should be so obvious, why couldn’t I see it? I’d invested so much of myself, was it all worthless?

Perhaps you can relate. Maybe you’re in that place right now. So here are three comforts to help you feel less alone, and three questions which will help you find a path forward.

Comfort 1: You’re Not Stupid

Putting your heart and your soul into something that matters to you is not stupid. Whether it’s a relationship, a career opportunity, or something else entirely, worthwhile pursuits require risk. They require us to invest ourselves without knowing what the outcome will be.

Sometimes, we judge ourselves because we look back and see all the red flags. But remember, they’re easier to see in hindsight. It’s genuinely hard to tell the difference between a legitimate caution and the sneaky fear that so easily holds us back. At the time, you probably were trying to discern whether those were bad signs or old baggage from your past making you afraid. Learn what you can, but give yourself grace for being human.

The hard reality is that you cannot control the world around you, but the fact that you invested yourself in something that mattered to you does not make you stupid.

Comfort 2: Every experience equips you for the future.

As you experience more in life, you will gain wisdom, and will be better able to discern which opportunities and relationships are for you. You’ll learn to trust your intuition more, and stand up for yourself. You’ll have a better understanding of what you want, and will be less likely to settle.

Comfort 3: You’ll get another chance.

What’s right in front of us seems like all that is real. Future relationships or future opportunities feel so theoretical, they may as well not exist. It would be so much easier if we knew when they were coming, wouldn’t it?

Unfortunately, we don’t get to know the specifics, not one minute in advance.

It’s okay to grieve what was lost. It won’t ever be the same. That person or that opportunity is gone, and when there is loss, there is grief. Trying to convince yourself you should just buck up actually prolongs the process.

As you grieve, though, trust that you will heal. As you heal, trust that you will open up to new dreams. Look for proof that life will bring more opportunities and people to you, because you will find it.

Question 1: What are you feeling and why?

This question can help you determine how to move forward. Our disappointments are often a tangle of emotions, which can cause us to shut down. When you can identify what you feel, it will help you determine how you can support yourself. What do you need to heal? What do you need to resolve?

• Frustration
• Regret
• Pain
• Anger
• Heartbreak
• Confusion
• Fear
• Worry

Try not to judge your answers. When it comes to what we feel, the words “should” and “shouldn’t” can be a trap. We catch ourselves saying things like “I should just be happy that…” or “It’s not like…” or “I shouldn’t be angry because…”

What if, instead of judging, you approach the emotion with curiosity? What is this emotion here to teach you?

It’s also worth asking, what are you afraid it means? What do you believe it says about you? Does it actually mean that?

Question 2: What is the best ending to the story you can imagine?  

“When we deny the story, it defines us. When we own the story, we can write a brave new ending.” -Brene Brown

This is another one where what’s in front of us seems like all that’s real, but it won’t always be like this. The future is coming, and we get to influence it. We get to plant proverbial seeds, take steps, and cultivate relationships, skills, opportunities…

I’ve found myself drawn to stories of late bloomers. If you’re feeling discouraged, Google “overnight success quotes.” The time frame for becoming a so-called overnight success is usually decades. That can be either discouraging or empowering, depending on how we look at it.

So, choose empowering. What is the best way you can picture the story unfolding from here? How might that inform the next steps you take?

Keep  going, and one day you might find yourself being quoted as the newest “overnight success” who just never gave up.

Question 3: What are the vital pieces to this puzzle?

Sometimes, we hold ourselves back from an option because it doesn’t look like the picture we had in mind, but if we look closer, it contains all of the vital pieces.

Vital = Life-Giving.

One of the things we do in the coaching world is to help people get to the root of what they want and why they want it. It’s important, because the externals can be fickle, and you can’t control the outside world. You can’t force a specific person to fall in love with you. You can’t force your body to conceive. You can’t force someone to hire you for a particular job. And you certainly can’t know whether any given attempt will work out.

What you can do is prepare to the absolute best of your ability.

You can make choices that line up with where you want to be.

You can be resourceful and flexible.

You can put yourself out there and show up as your complete, awesome self.

You can live a joyful, creative, meaningful life in the meantime.

So give some thought to this. What are the vital pieces to your vision? No matter what your goals are, or what the disappointments are, clear away the externals and look at what’s underneath. What can you learn about yourself, and what you’re here for?

Then tell the best story you can tell.