5 Secrets to Being Happy in your 20s

My 20s – well the first six years of it- haven’t gone as planned. Chances are if you reading this, your 20s probably haven’t either.

I feel like I’m on the world’s longest emotional rollercoaster ride. Some days I feel like I’m on the top of the biggest hill. Giddy, happy and enthusiastic.  Other nights – like tonight- I feel like I’m free-falling down the biggest coaster drop, and all I want to do is curl up into a ball and cry in self-pity, “Why me?”

I like to think that though all of the heartbreaks, disappointments and failures that I have dealt with, I’ve become a really strong mid-20-something female. I’m independent. I’m fighter with a can-do attitude. I can handle any curveball that life throws my way. The reality is most days I’m pretty sure this is just a facade. A coping mechanism that I put on to shield myself from all the trauma I’ve gone through.

The only thing that I can really think of that’s gotten me through all this is getting really comfortable being uncomfortable. 

I know this may sound like pure torture to many of you. Why would anyone voluntarily place themselves in a situation that freaks them out or scares them shitless?

But, looking back, the scariest, most uncertain times in my life has made me that much more appreciative of what I have and often have resulted in my fondest memories. It’s forced me to be vulnerable and live in the NOW. 

I feel like being vulnerable has negative connotations in our society. In reality, I actually think it’s a good thing. It forces you to be on your toes, open yourself up and be more authentic. Most importantly, it forces you to appreciate what you do have and live in the NOW.

As I’m going on like year three of what seems like a never-ending quarter-life crisis, the biggest lessons I keep encountering from my mentors- who are all older than me- all stem back to getting uncomfortable and living in the NOW.

So, how exactly do you get more UNcomfortable? Here’s five tips from some of my favorite bloggers that I keep going back to and re-reading day after day.

1. Get Comfortable Flying Solo 

How many of you have always thought about going to a nice dinner all by lonesome? Or, grabbing a drink at the bar by yourself? I know I have. However, I usually chicken out before doing it. I let self-doubt and the fear of being perceived as “awkward” or as a creepy loner get in the way of possibly a delicious meal.

Then, I look at bloggers, like Torre DeRoche, who took a 10 day solo retreat, and realize all the things that I am missing out on because I’m not comfortable going solo. As Torre wrote,  “This is why it’s so important to learn how to love your own company, to travel solo, to dine for one. We are each living out our own journeys and so we much take care of our own needs, desires and dreams.”

2. Dream Big, But Work Harder 

This is the first decade where most of us are flying free. For the first 18 or so years of our lives, we went to school and lived by our parents’ and teachers’ rules. Then, we had college, where we got to express more of our individuality, but still lived within quite a few constraints.

Our 20s are really the first time where we get to live 100% on on our terms. Many of us start out with big dreams. Most end up abandoning them fairly quickly- usually because of lack of instant gratification, a societal pressure to “be an adult” or simply it’s too hard.

The reality is it’s easy to cruise on auto-pilot and succumb to societal pressures of being an adult in a 9 to 5 TPS report-filing cubicle job. If you want to live like they do in Office Space, by all means do it.

However, if you have bigger dreams and aspirations, it’s going to require a shit ton of work.  Like this post on the The Porch Dallas, you will need to be willing to forge ahead with a lot of hard work without a lot of instant gratification.

“Almost nothing truly worthwhile comes quickly. It takes time and discipline to become an Olympic athlete, or to simply get in shape; to get a degree, or become a CPA, or become a great husband or wife. And any of the things you truly want long-term can be derailed by indulging yourself in the moment.”

3. Don’t Settle. 

It’s not just being willing to dream big, but it’s also about not being willing to settle in your 20s. This is really the only decade in your life where you are expected to explore and try new things without having big ramifications. Once you have a wife/husband and/or kids, you have a lot more responsibilities to handle. And, a lot less ability to explore and take risks.

Don’t blow the opportunity by settling and getting too comfortable in your 20s. According to the Milk The Pigeon Blog, “the problem with comfort is that it’s boring. You don’t acquire life experience through comfort and familiarity.” 

4. It’s not your practice life.

Don’t just succumb to wanderlust and exploration with the thought of I can just start my real life in my 30s. There is no do-over time. Explore and take risks, but with a purpose of finding your true identity and calling. Make your 20s count for something.

As Penelope Trunk said, “Take your life seriously enough to be able to share difficulties and failures,” said Trunk.  “And remember that the best decisions you can make are ones that will last into your thirties. That way, you know you are doing things in your twenties that will matter.”

5. Being able to answer this question honestly.

What does it mean (for you) to live a good life? Not sure. Check out this brilliant video from Jonathan Fields as he interviews 29 change-makers on what leading a good life means to them.

What tips do you have for getting comfortable being uncomfortable in your 20s? Please share in the comment section below.


  1. alittlewifeshappylife May 13, 2014 at 2:18 am #

    #1 is so key! I got married young (23), but I made sure to do things “alone” as much as I could- it’s made me a much more independent person now. That’s one of the great things about dating long-distance, too- you kind of have to do things alone! 

    Great post!


    • admin May 15, 2014 at 5:53 am #

      Props to you for making a long-distance relationship work. That takes a lot of trust and compromise! 🙂


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