14 Small Challenges That Will Push You Toward Your Best Life

thumbnail image - Jorge Sanmartín Maïssa
thumbnail image – Jorge Sanmartín Maïssa

Has your life been a little dull lately?


I heard that we’re supposed to do one thing a day that scares us but I’ve never managed to come up with enough scary ideas to fulfill that. I mean, how many roller coasters can one person ride? That shit gets expensive.

As a (mostly) low-cost alternative, I came up with fourteen mini challenges that are entirely possible to breeze through over a two-week period. They may not all be scary but they’re all, in some form, designed to push you out of your comfort zone and get in touch with the absolute best version of yourself.

If you want to put these to the test, I want to help! Tweet at me, message me or email me letting me know which one you tried and I’ll try the same one. We’ll swap awesome, fulfilling, embarrassing stories. Deal?

Let’s up the ante together.

1. Deliberately embarrass yourself.

Ask out someone who might not like you back. Voice your opinion about something that you’re not sure anyone agrees with you on. Tell someone your deepest feelings even if it makes you feel all squirmy and awful to do so. This isn’t so much about having an embarrassing story to tell as it is about getting in touch with the vulnerable parts of yourself and learning to share them. It’s where the absolute best connection happens, and it only happens after we push through feelings of shame and embarrassment.

2. Apply for your dream job.

Even if they’re not hiring and you’re not qualified and it is going to take hours to fill out the application. Fill it out. Send it in. As someone who has – on more than one occasion – scored a job that they’re vastly under qualified for, I can assure you it is not always a lost cause. Worst case scenario you learn which skills you need to work on, and you put yourself on the company’s radar. Win-win.

3. Do one hour of a physical activity that you have never done before.

Don’t go to your gym and get on the same elliptical trainer you’ve gotten on every day for the past five years. Try something TOTALLY new. Go rock climbing! Play water polo! Pick up a unicycle! Give whatever it is your best shot and who knows – you might even find you love it!

4. Handwrite a note to someone you care about, listing all the things you admire about them.

And then give them the note! If possible, deliver it in person. Realize how much it makes your own day to make someone else’s.

5. Text every person in your phone. If you don’t want to text them, delete their number.

Be ruthless. You’ll quickly realize how many people you know vs. how many people you actually take the time to communicate with. I did this a year ago and I can promise you it has amazing results. You’ll reconnect with the people who still matter and you’ll drop the people who don’t.

6. Unplug for an entire day.

Don’t use your phone OR the Internet for the entire day. If you go out, leave your devices behind. Don’t instagram. Don’t tweet. Don’t text. Go outside and actually live your life, from the time you wake up until the time you go to bed. No, I know. It’s CRAZY.

7. For a whole day, only eat things you’ve never eaten before.

You know those green smoothies you keep talking about making? Today is your day to make it happen! From the time you wake up until the time you go to bed tonight, only ingest things that you have never eaten before. You might find a new power food that you LOVE. Or you might break out in hives. Let’s hope for the former.

8. Have a full conversation with a stranger.

As in, someone you have never talked to before in your life.

Maybe it’s someone on the bus. Maybe it’s the person sitting alone at your coffee shop. Or maybe it’s the neighbor you always wave to but never say hello to. In any case, make the conscious effort to learn a little something new about a person you don’t know. At best you make a lifelong friend. At worst you conquer a fear.

9. For a whole day, don’t lie.

Not once. All day long.

This is going to force you to confront your own thought patterns in a big way. Every time you struggle to phrase something honestly, you will realize that it’s a situation in which you usually lie. Yikes.

10. Give $100 to a charity (or a loved one in need) anonymously.

If you can’t spare $100, commit yourself to 10 hours of volunteer work to a worthwhile cause. Recognize the immense power of giving without expecting anything in return.

11. Read an entire book in one sitting.

Okay, fine. Go for a walk in between chapters thirteen and fourteen if you must. But gosh darn it, try your hardest to get that book finished. We so rarely take the time to let ourselves learn or absorb someone else’s work without interruption these days – use this as your chance to do so. It doesn’t have to be a Harry Potter sized novel – check out Thought Catalog eBooks for some short, digestible reads.

12. Connect with someone who works in a field you want to break into.

Send an email or a letter or a tweet to someone whose life you want. Ask them to meet up for coffee and pick their brain about how they got into their field of choice. It may be a more attainable career than you thought! At the very least you’ll make a connection.

13. Devote two uninterrupted hours of your day to learning a new skill.

Is there an instrument you’ve always wanted to play? A language you have wanted to learn? A class you’ve always wanted to go to? Today, devote two hours to practicing a skill that you have always wished you had. If you like it, repeat the next week. And the next. Marvel over just how quickly you pick up new things when you allow yourself to practice them without distraction.

14. Treat yourself.

When was the last time you took an hour, an afternoon or an entire day and devoted it solely to your own enjoyment? Today, make time for yourself. Sleep in late. Splurge on brunch. Buy yourself that outfit you’ve been eying up, or call up old friends and devote an afternoon entirely to catching up. Use today to celebrate the fact that you’ve been working hard for the past few weeks (or months, or years) and you deserve a break. Challenge yourself to celebrate the most important person in your life. Thought Catalog Logo Mark

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