9 Surprising Signs Your 20s are Going Better Than You Think


Failing and your twenties go together like Chip and Joanna Gaines. They seem to always be together.

If your 20s haven’t exactly gone as planned, you’re not alone.

Actually, you’re more in the norm than you think.

Nobodies life is as good as it looks on Instagram. As I write about in my new book 101 Questions You Need to Ask in Your Twenties:

There’s another side to everyone’s Instagram photo that they’re not exactly taking a picture of.”

Maybe your twenties are going even better than you think. Even if you feel lost. Even if the challenges you’re facing feel overwhelming.

Check out these surprising signs your twenties are actually going better than you realize.

9 Surprising Signs Your 20s are Going Better Than You Think


1. You’re taking strategic risks

The biggest risk you can take in your twenties is not taking any risks at all!


Success in your 20s is having the courage to write a crappy first draft. In a few rewrites, you’ll figure out the story you’re supposed to tell. (click to tweet that)

Keep working on writing your story instead of envying everyone else’s.

2. Nothing feels normal

This doesn’t sound very exciting, but I promise it’s a good thing.

Feeling a little abnormal is the new normal of your twenties.

That just means you’re exploring, trying new things, and finding a new path. If everything felt normal, then you wouldn’t be changing, growing, or creating. You’d be that person still eating five bowls of cereal in your college cafeteria.

While I miss eating bowl after bowl of Berry Captain Crunch, my body is very thankful there is a new normal.

3. You’ve lost some baggage

No, I’m not talking about throwing your luggage off your next American Airlines flight. They frown on that.

I’m talking about cutting off some of the heavy stuff that has been dragging you down. Sometimes that can be a toxic relationship.

Or maybe it’s just negative thoughts you’ve believed about yourself for too long. You don’t grow up without having some negative definitions people have thrown at you stuck on your white canvas.

Whether it’s with a friend or dating relationship, sometimes breaking up is the best thing that could’ve happened. While breakups can feel uncomfortable and painful, it’s actually freeing you to run free and with more purpose.

It’s hard to run a race with a block of cement tied to your ankle.

4.  There’s so much you don’t know

When you graduate college, ready to change the world, then quickly realize that you don’t know squat, it can be a sickening feeling.

Yet, the moment you realize how much you don’t know, is the moment a fire is lit to learn more. To dive deeper. To open great books and really ask people questions, not for a grade, but because your life depends on it.

A passionate learner who realizes how much they don’t know is ten times better off than a complacent person who thinks they know everything.


5. You feel challenged at your job

As I first wrote in 101 Secrets For Your Twenties,

The most dangerous job you can have in your twenties is a comfortable one.”

If you feel stretched and challenged at work, maybe that’s a really good thing. Maybe you’re learning and growing way more than if your job came easy.

Sure, it’s not comfortable, but comfort should not be the goal of your twenties.

It’s really hard to do anything worth doing and remain comfortable in the process.

If you’re job does feel easy, maybe it’s time to explore ways to make it more challenging.


6. You’re asking yourself really good questions

I don’t think there’s anything more important in your 20s than the questions you bring to it. Obviously I think that since my new book has 101 strategic questions for your twenties in it!

If you don’t ask yourself smart, strategic questions about the future you want to live, how are you going to live it?

7. Your outcomes aren’t exactly Instagrammable (yet), but the work you’re doing is getting much better

Your 20s are a process, a step-by-step progression, hopefully building a foundation that will last you a lifetime.

One hit wonders are that because they weren’t able to build a foundation to sustain the weight of success. Notorious B.I.G sang “More money, more problems” for a reason.

Success in your twenties is in the details.

Success is found in the work, not in the sexy outcomes.

If your work is getting better, the right outcomes will come at the right time. I promise.

Success in your 20s and 30s is less about what you harvest, and more about what you plant in the ground! Keep planting, and watering, those seeds. (click to tweet that)


8. You Still Feel a Little Lost

Remember, the first step to exploring is getting lost.

Get lost on purpose with purpose for a purpose.

There’s something of strange significance that happens to us when we lose everything we used to depend on. 

If you’re not a little lost, then you’re not exploring and risking.

A life spent on the hot, dusty, trail, following the posteriors of all the people in front of you, is not much of a life at all.

Take a hard right and start figuring out the trail you want to create.

9. You’re not struggling as much to talk about where you’re struggling

We can’t do this journey alone. It’s too hard and too dangerous.

Plus, we connect with each other because of the struggle, not in spite of it.

As I write in 101 Questions You Need to Ask in Your Twenties:

We don’t connect with each other through our pretend perfection. We connect over our shared struggle.

Authenticity starts with you. Be brave enough to go first.

None of us have it all figured out. Those who think they do, are the ones in for the biggest shock of them all.

Yes, the struggle is real. The conversation about it needs to be even realer. 

I’d love to hear from you within the comments on this article — which of these signs do you relate to the most?


  1. Audra Edmonson

    This is so refreshing to read! I read a lot of your articles in my early twenties (about 3 years ago), and coming back to it in my mid twenties is very eye-opening. I found I’d fallen into a lot of the same toxic thought processes I’d had before; i.e wondering why I wasn’t “there” yet, thinking other people had done so much with their lives already, and lamenting my whole future. Thanks for all your great advice as always. I can’t wait to read your new book!

    • Paul Angone - All Groan Up

      Thanks Audra! I really appreciate the kind words and feedback.Yeah I find myself constantly slipping into these pitfalls without even realizing I’ve fallen in.


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