17 Remarkable Challenges

I read a post some years ago about a lady who wrote about How To Do Things. She was feeling lost and needed to do things. So, trying to convince herself that she knows many things, she wrote 25 things worth doing. 

This post is my version of the same post, and it’s about how to do new things.

If you’re at a point in your life where you think you don’t have anything to do (or you feel lonely), you can try any of these challenges. 

I have tried some. I have also written about some of them in previous posts. And I am trying a few others so you can come around the blog, and this post will get updated. 

Why You Should try the challenges in this post: 

  • You will learn new skills 
  • Overcome some of your fears 
  • Some challenges will improve your interpersonal skills, like discipline, empathy, and learning.
  • Etc. 

1. Do push-ups for 336 days 

This is a simple activity you can do to improve your health. This will teach you consistency and how building your dream body works. The truth is, you will gain more from consistency than anything else. 

By the way, you’re doing it for 336 days to get a month’s break in a year. You can start with five push-ups per day, and by the end of the year, you should push for 50 at a go.

99% recommended. 

2. Write a letter to your younger self 

The benefit of this challenge is that you will reflect on your life if you haven’t done that before. 

It is as challenging as telling your younger self all the mistakes you could have avoided or things you want to do differently. If there is nothing like that, just reminisce and write about funny moments. 

50% recommended.

3. Travel across the country by train or bus 

It is difficult to do because your body gets tired the further you go. You will feel like a bag of old bones at the end of a long traveling. The good thing is, if you travel long enough, you will see how geography changes gradually across the map. It’s like traveling across the map in your geography class and seeing things for yourself. 

4. Teach yourself how to fall in love deeply 

This is complicated, but it starts with finding someone you like and telling them how you feel. If they say yes, your job is never to hold anything back. 

If you think life is about taking risks — 99% recommend this. 

Check the next challenge if you think love is a business for the weak.

4. Become an expert at something outside your job 

I have a friend who likes talking about cars. As of today, he doesn’t own a car. But if I had questions about cars, I could ask him, and he would answer them in detail. 

This is a fun challenge. It looks like a hobby, but it’s slightly more than that. It’s about finding something that fascinates you and learning as much as possible about it. You don’t have to monetize it. You don’t have to do it anymore once you master it. 

It could be anything — kayaking, repairing electronics, or mountain climbing.

5. Read the biography or autobiography of three people in one field 

If you’re a programmer, read the autobiography of three great programmers. This exercise can help you become an expert in your field. If you are a business owner or a startup founder, you can read the autobiography of three founders. I’ll recommend Steve Jobs, Charlie Munger’s Book, and Almanac of Naval.

You can find self-help book recommendations on this blog. There are recommendations for twentysomethings, too. 

6. Start a wild online diary 

This challenge is not for everyone but for people with wild ideas and wild thoughts. You will be surprised by how many people love reading or hearing other people’s ideas, irrespective of how they sound. Reddit, Twitter, and Tumblr are filled with these kinds of people. You can start a blog – like a free WordPress blog.

Do this with caution, though. You may have wild ideas, but some outlandish ideas are disgusting to hear. 

7. Travel by ship 

Another risk worth taking. You’re signing up for a long commitment. Once you are on a ship, it’s almost impossible to stop them in the middle of the journey and turn back. You’ll likely be there for months. 

I haven’t tried, and I have heard it comes with a few risks — if you fall sick and die, what happens to your body? Finding a missing person last seen on a ship is also hard. How do they find them? Inside the sea? 

Sorry, I am not abnormal. I am just thinking.

7% recommended.

8. Learn how to prepare 20 delicacies 

You can try this challenge if you’re bored, lonely, or have just moved to a new city. Try learning how to cook the meals of your new country or city. You can just learn them for the fun of it. 

9. Move to A New City 

It’s simple. Move to a place where the culture and lifestyle are a lot different. 

You might want to pick a few traveling essentials before you move

10. Document your adaptation process to a new life or culture 

I have a favorite content creator who I have been following for years. They have just moved to the Netherlands, and their content is about adjusting to life. It’s fascinating to watch. It feels like I am on this journey with them. I love it.

You can also document other challenges on the list, like traveling by bus or reading classic literature.

And that brings us to point number 11. 

11. Read 100 Classic Literature

I love this one. Reading about 100 classic literature might take your lifetime, but it will be worth it. One thing I can guess about someone who has read 100 classics is that they will have fascinating thoughts, and studying how their mind works will be worth studying. 

100% recommended.

I have written some of my reviews on the classics I have read, like East of Eden (my favorite) and The Handmaid’s Tale

12. Learn a craft you can monetize 

Many people learn crafts as a hobby, which is great if that works for you. Trying to monetize is like taking the game to another level. You will learn a few things after you start selling your stuff. That thing is called ‘business.’

13. Serve as a mentor or confidant 

Serving as a mentor to someone can be something fulfilling — if your mentee makes it. I have seen teachers look so proud when they see their past students making it farther in their careers. This is a long shot, and it might take a lot of time before your mentee gets to the top. I wrote about how long it takes to become an expert. But if you love the area of expertise, then it wouldn’t be a problem. Teaching someone how to code, for instance, can make you both a better developer and a better teacher. 

14. Explore your faith or some existential questions 

Who is God? What’s the meaning of life? Why are we here? What should I do with my life? What is the meaning of love? 

Here is a little hint about the meaning of life. Each person has their own meaning. The first mistake is to assume that there is a general answer. There isn’t. Secondly, the meaning of your life will not be handed to you. You find it. So, maybe start googling things or start doing things. Start finding answers to the questions in your head.

I will leave you to try. 

15. Compliment one person per day for 30 days 

This is not as easy as it sounds. You see people every day, and in your head, you might tell yourself, “That lady looks gorgeous, or that man looks amazing in those shirts.” How about you tell that to one person per day? Stop holding compliments in your head and give them to people. It’s like a burden, right? Why not give it to the person? 

Yes, if you try it, some might look at you weirdly, and then you have to learn how to deliver compliments, which is a skill. Smile. Approach people from the front. Don’t stalk. Be direct. Don’t walk around like someone who wants to run away. 

If you do it right, you will make many people happy. Your perspective about life will change.

You can take it further by helping people with little things every day. This post is about how to do new things. And this step can teach you a lot about how to work with people. Being aggressive doesn’t solve that much. For you to compliment people, you have to learn to be confident. It forces you to forget about your problems temporarily. So, you learn how to do new things — getting out of your head, loving yourself, and making people feel better about their day or life. 

Bonus: check out the movie A Man Called Otto

16. Learn a new language 

Learn a new language. 

I am still thinking about watching French movies without subtitles and moving to a French-speaking country someday. I should take my French seriously. 

17. Do something hard 

I have read some fascinating stuff people did that I want to try, too. 

Annie Dillard wrote Pilgrim At Tinker Creek while living in a suburb. Elizabeth Gilbert wrote Eat, Pray, Love while traveling around the world. 

How do you find out what to do in this case? If you’re interested, follow people on social media, read autobiographies, or join specific Reddit communities. 

How to do new things 

Start with the simple ones. Once you have done a few, you will grow confident you can do more. And if you like to share your experience, you can tell me about it on Twitter or LinkedIn. Use the contact button at the top. 

Hello, I am Adekusibe Ogunmokun, a content Strategist and web developer. Contact me if you need to build a website or create effective content for your website. Check my service page.

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