How to Overcome Disappointment

Surviving your 20s can feel a lot like this..


If you’re alive and reading this right now, there’s a good chance you’ve been disappointed about something.

A crappy job. Relationship problems. Sickness. A political election. Or life in general is going nothing like you planned. Pick your disappointment.

Disappointment loves sneaking up on you — like that weird neighborhood cat who keeps showing up on your porch and peeing all over your decorative pillows.

So the question becomes — how do we overcome the disappointments in our lives?

And I write this having gone through my fair share. You don’t take the path of an entrepreneur without a lot of failures paving your way. Unmet expectations are a close companion.

We can’t avoid disappointment. But if we let each disappointment stop our momentum, we will not make it very far in life.

How do we overcome disappointment in our lives? Here’s some ideas:

3 Ways to Overcome Disappointment


1. Stop tying your identity to the perceived outcome of your work

Sometimes we’re wrecked with disappointment because we’re tying too much of who we are to what we do.

As I first wrote about  in 101 Questions You Need to Ask in Your Twenties (and Thirties)

You are more than the visible outcome of your work.

And the outcome of your work might be more than what is currently visible.

Do good work. Put your dream out there. Do your best to help others.

Then, let it go. Your dream can’t fly if your identity and self-worth is clinging onto the back of it.”

You are more than what you do. Who you’re becoming is more important than what you’re doing.

“If you’re truly humble, nothing with touch you, neither praise nor disgrace because you know what you are.” – Mother Theresa

Who you are, inside and out, will always be more important than your perceived accomplishment or failure in the moment. Who you are will always outweigh and in some cases unravel what you’ve done.

“We think the outcome is the entire point, when it is just another step on the journey. If we make the whole journey about the predetermined outcome we envisioned, we are destined to be disappointed and disillusioned.”25 Lies Twentysomethings Need to Stop Believing

See each outcome, good or bad, for the next step that it is and keep walking forward.

2. Have Faith.

The more I’m trying to have everything work out exactly how I planned it, in exactly my timing, the more disappointed I’m going to be. I know this. Yet, I still try to grip tight to all the details of my day.

The more faith I have that God is working things out better than I ever could, even if I can’t see it at the moment, the more peace I have.

It’s not a blind faith, it’s a faith seeing with eyes wide open how many times God has come through for me.

If we’re only looking at what we can see, we will miss everything else that is going on.

What you see as a failure now, might save someone else’s life later. 

“Outcomes can only be seen through the lens of eternity. And since we don’t exactly have that kind of sight, I think we’re all better off if we don’t stare at our immediate outcomes for too long.” – 25 Lies Twentysomethings Need to Stop Believing 

You never know how a “disappointment” will look in retrospect.

Sometimes what we see as a disappointment now is merely a blessing to be discovered later. (click to tweet that)

3. Be willing to be adaptable

Sometimes the best plan you can make is to plan to continually make new plans.

“Success in life is not about things going as we planned. But how we adapt, change, and grow when they don’t go as planned.” – 101 Questions You Need to Ask in Your Twenties (and Thirties) 

If you let each failed plan and exploding expectation overwhelm you with disappointment, you won’t be able to move forward very far in life. Yet, it’s hard to be too disappointed in life if you’re willing to adapt your plans when they don’t go exactly as planned.

It’s only a dead-end if you let it stop you. Or you can climb the wall in front of you and get a better view.

Or as I wrote as Secret #1 in 101 Secrets For Your Twenties,

Sometimes surviving your 20s is nothing more glamorous than just holding on for dear life on the back of an inner tube like a

kid being whipped around by a speedboat.

You can’t see a thing.

Repeated waves knock the wind out of you.

Your hands are gripped so tight your fingers begin to cramp. And your only choice of survival is to just let go.

Surviving your 20s can feel a lot like this..



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