How To Stay Optimistic When Times Get Tough

When the going gets rough, the tough keep going. 

At least, that’s what they say. 

But how often do we feel “tough enough” to keep going when times get rough? 

For many of us, finding the motivation to keep moving forward during trying times is incredibly difficult. Whether disappointment stems from a job loss or a personal failure of some kind, the fact of the matter is disappointment stinks. Feeling as though we have failed or that our situation is hopeless, stinks. Period.

This week on Episode 147 of the podcast, I’m sitting down to chat with Jess Ekstrom, founder and CEO of Headbands of Hope, an expert in optimism and the author of Chasing the Bright Side

During our conversation, Jess and I touch on the power of positivity, and how we can use it to our advantage no matter what may be happening in the background of life.

And I think that it’s an important topic to bring forward here today because, as someone who has experienced quite a few trying times, I am well versed in how heavy disappointment can feel. 

After all, before I started inkWELL Press, I had made the incredibly tough decision to close down a very lucrative business because I had lost my passion for it, and I was at a complete loss on what to do next.

So today, let’s take a look at a few ways that we can rise above during the trying seasons of life by focusing on how we can remain optimistic in the face of disappointment. 

Because, to me, when the going gets rough, the tough don’t just keep going. The tough keep going by flipping the script on the negativity that surrounds their rough situation instead!


Three Ways to Stay Optimistic

Quiet Your Inner Story-Teller–

Whenever we are met with disappointment, we sometimes run into what I like to call our inner story-teller. 

It’s that little voice that laughs at us when things go wrong, and that tells us that we can’t do the things that we want (and sometimes need) to do to get ourselves to the point where we want to be in life.

Frankly, that little voice doesn’t always spin the best stories.

So, one thing that I have gotten into the habit of doing whenever I’m having a particularly trying day (or season, let’s say) is to tell my inner story-teller to keep quiet. 

Whenever I find my inner voice spinning a tale of defeat, I take a deep breath in and focus my energy on something positive as a way to drown out the sound. 

Whatever you can do to tell your inner story-teller to take a hike when you’re going through a trying time, do it!

The more you stop listening to the negative tales you’re telling yourself, the happier you’ll be, and the easier it will be for you to find the silver lining to your disappointing situation (whatever it might be).



Meditation is one of those things that, to some, may feel a bit woo-woo when you’re first starting, but once you get the hang of it, meditation can turn almost any bad day around for the better.

This is because meditation allows us to get out of our heads–out of the habit of focusing on the What if’s of our trying times, and into the practice of being present as much as possible.

And when we are present, we can take ourselves out of a tailspin of negativity, and into a more positive space at the drop of a hat.

In other words, meditation has a calming effect on the brain. It slows down our thought processes and allows us the reprieve we need to refocus our energy for the better.

When your mind is calm, you’re more likely to look at what is happening around you in a more positive light. 

The next time you’re feeling uneasy or anxious about what you have on your plate, give it a try! 


Use Your Power of Choice–

Here’s the thing: no matter what happens, you have the power to choose your reaction. 

In other words, if you’re going through a rough time, you can choose to dwell on the bad, to stew in that negative space, if you will, or you can choose to look for the good (that silver lining) that I feel exists in nearly all situations.

Whenever I am going through something rough, I like to employ the Squirrel Strategy to help me overcome the obstacles that I’m faced with. 

In fact, I used it to figure out where I wanted to go next after I closed my business and felt I had utterly failed myself and my loved ones! And I still use it to this day when I’m brainstorming ways around obstacles that my team and I are faced with at IWP.

So, the next time you’re faced with a challenge, I encourage you to employ your power of choice by giving the squirrel strategy a try. 

Write down some of the positive things that surround your situation, whatever it might be. Keep brainstorming ways that you might be able to overcome your adversity until you arrive at an idea that seems plausible.

I like to write the alphabet on a piece of paper and come up with some words or ideas that correspond with each letter, but you can use whatever method works best for your inner squirrel. 

The more you make the conscious effort to look at what’s in front of you in a positive light, the easier it will be to pick yourself up by your bootstraps and keep going when the going gets a little rough.

Remember: you have the power to choose how you approach what life throws at you, so choose wisely!

How do you stay optimistic when times get rough? Share your experiences in the comments below . . .

And check out Episode 147 of Productivity Paradox to hear about Jess’s story, and how she came to embrace the power of positivity and use it to create Headbands of Hope!

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Tonya Dalton
Tonya Dalton