How to Take Disappointment and Turn it Into a Win

I picked up my phone after a walk with Lou and noticed a voicemail and text from my Playa Resorts BDM. “Oh boy…” I thought, “This can’t be good.”

I proceeded to give him a call back and he notified me that our 20K Fam trip was cancelled. My heart sank… 💔

Of course, I had just finished doing a Facebook Live letting everyone in the Fam group know that everything was a-go and then word came back from the higher-ups to cancel all Fams for the next two weeks due to the hurricane.

I was disappointed and knew others would be, too.


After the season that we in the wedding and travel industry have been in, we all needed this trip. It was more than a site inspection opportunity, it was a reward for persevering for months and months, trusting that things would turn around in our favor.

It was the hope and spark that we needed to keep pressing forward and start creating a buzz that travel is back, and travel is safe.

In life, there are disappointments. We can be disappointed in ourselves, in others, in results or lack of them. We can be disappointed in the weather, a meal, or a conversation. Disappointment can be found in a lot of things.

Wow, Tami, this is so encouraging! I think I’ll keep reading more so I can be disappointed in taking the time to hear your thoughts. 😂

It was the hope and spark that we needed to keep pressing forward...

In all seriousness, if we don’t know how to take disappointments and either let them roll off us or turn them into a win, it will be a struggle for us to be successful as entrepreneurs because we won’t have the mental toughness to persevere when times get tough.

I believe one of the biggest ways to turn a disappointment into a win is through HOPE. We have to find hope in all things. God’s word says that “Hope deferred makes the heart sick.” (Proverbs 12:12a). That is a very powerful statement and oh-so-true.

So, how do you find hope in times like these? Well, one of our planners who was going on the Fam reminded me that the trip wasn’t canceled, it was postponed. Wow! That is a huge mindset shift, yet only a one-word difference! ✨✨✨

“Hope deferred makes the heart sick.” Proverbs 12:12a

That one word, “postponed”, changed my perspective and it reignited my hope! So, when you find yourself searching for the hope, consider even the smallest change in perspective and of course, always remember that true hope only comes from God. 💖

Speaking of perspective, what is your thought on exercise?

One way to turn disappointment into a win can be learned through making yourself exercise. Exercise is one of those things that positions you to be uncomfortable and sometimes in pain yet still pushing yourself, asking more of yourself and persevering even when you’re exhausted.

Purposely putting yourself in places where you are stretched develops mental toughness and that allows you to have a bounce-back ability when disappointments come your way.

Always remember that true hope only comes from God.

So, we can almost prepare ourselves for disappointments by training ourselves to be in situations we don’t like in order to come out ahead. Does it mean we won’t be disappointed in life? No. But it trains us to respond differently.

The third and final way to turn a disappointment into a win is to remind yourself that how you do anything is how you do everything.

I’m sure you’ve heard that saying from Charles Swindoll “Life is 10% what happens to you and 90% how you react to it.”

“Life is 10% what happens to you and 90% how you react to it.” - Charles Swindoll

I would say that is accurate. And if that is true and the statement that how you do anything is how you do everything is true, then we need to be mindful of how we respond and react to what life throws at us.

I’ve had many couples over the years ruin their trips by allowing one negative experience bring them to a downward spiral where they simply couldn’t get past it and enjoy their trip. It always amazed me how one tiny situation ruined the other 99% of what could have been a vacation filled with amazing memories, laughter and fun.

Well, there you have it. When life throws you lemons, grab some sugar and make lemonade! 🍋

Struggling to get your business back on track during the travel resurgence? My free masterclass may give you the hope and tips you need. Catch the replay here 👇


  1. Shevonne Rice on October 16, 2020 at 8:36 pm

    Hello, I interested in the job offer that was offered.

Leave a Comment