Why you shouldn’t be realistic about accomplishment in your twenties

I saw a post on Reddit the other day where a young man asked the question:

What should you have realistically accomplished in your twenties?

He listed off a couple of items like home ownership, marriage, salary, etc. and asked for input on other expected items.

The responses to his question varied but the underlying consensus seemed to me to be pretty overwhelming…

That question is bullsh*t!

I couldn’t agree more, so I decided to write this article to implore other twenty-somethings to please, stop asking yourself this question.

If you are frequently asking yourself this question or find the pressure of its assumed significance weighing on you, I’m sorry, but you’ve fallen victim to the anxiety-inducing media coverage of 18 year-old tech startup CEOs, the expectations of previous generations and the pressure to adapt.

The truth of the matter is, succumbing to this question and allowing it to shape your goals is the fastest way to mediocrity. And the fastest way to succumbing to this question is by being realistic about what you should accomplish in your twenties. It’s ok if you don’t know what to do with your life, but please…

Stop being realistic! Stop playing by the rules.


There are no rules!

What do I think you should have accomplished in your twenties?

Nothing. Zero. Nada. Zilch.

Your twenties are a time for setting the framework for your life’s work. Not a time to compare and meet expectations.

Your twenties are a time to do all kinds of weird sh*t. Checking off boxes on the previous generation’s life template is not one of them.

Yes, making moves, creating, getting promoted, winning awards, getting recognition, and making your parents relieved that you aren’t a total screw-up are nice, warm and fuzzy feelings to have, but that is not what your twenties are for. They are for exploring, nurturing and embarking on your life’s journey.

I personally know people in their twenties across all angles of the life spectrum.

Newly married. Married with children. Jobless. In grad school. Working minimum wage jobs. CEOs of their companies. Rising stars of their own companies. Recently laid off… and everything in between.

These are vastly different phases of life and these individuals are all in their twenties. Their respective life journeys are incredibly diverse but they are all leading them somewhere unique. So, how can we hold them to a common standard? A common expectation?

Here are 6 ways to think about accomplishment in your twenties.

*I never want to become a self-help blogger or “guru.” Please accept my advice below as a simple reflection of what I have learned lately. Take it or leave it.

1. Nothing good can come from the question of ‘what should I accomplish in my twenties?’


This question is a lose:lose scenario.

If you don’t match the expectations presumably set for you, you will naturally feel like a failure.

If you have checked all the boxes and are excelling, it’s likely that you might become complacent and not continue in that manner anymore. I have seen this firsthand.

Avoid asking yourself this realistic question in the first place.

2. Nobody actually cares! Seriously.

Pardon my French, but who the f*ck cares?


Like many people, I sometimes find myself struck with a sense of inferiority or diminished worth when comparing myself to others.

What must so-and-so think of me? I’ve only done xyz and he’s done abc?

I am the odd man out here. Everyone is thinking that.

While I am convinced that everyone is staring at me as I walk down the Chicago streets (anyone else?), this is indeed not true. The same goes for the fact that no one is judging you or truly cares! Don’t believe me?

Check out the book Status Anxiety by Alain de Botton in which he asserts his thesis that nobody cares or thinks about what you’re doing and that you shouldn’t care either way. It’s powerful stuff and backed by some great insight.

So, ignore this question and instead, stop comparing yourself in the first place.

I hate to break it to you, but there will always be someone better at something than you. That’s the reality of the world. So, to compare yourself in this fashion is setting yourself up for failure and a life of frustration.

3. Ask yourself the right questions

I am all for setting goals and pushing oneself. This is essential for setting out in the right direction. If you don’t have your compass set, you’ll end up anywhere the wind takes you… in someone else’s dream. Plagiarizing someone else’s life.

If you are setting your goals based on what you think you SHOULD accomplish or what you should do, you are going about it ass backwards.

Instead of thinking tangibly about what you want to DO or ACCOMPLISH,  you should be asking yourself, what makes me happy?

I’m not talking happy in the sense that it makes you happy because it makes you financially secure, or happy because its whats expected of you and you are relieved as a result.

I’m literally taking about what puts a smile on your face. Butterflies, rainbows and fuzzy puppy-type stuff.


That is what your twenties are for. To do that, you need to establish what is important in your life.

For example, this is what I have determined is important to me:

  • Discovering and engaging in new experiences in familiar and unfamiliar environments
  • Meeting new people
  • Finding a new perspective on the world.
  • Improving aspects of my life each and every day.
  • Never accepting the status quo. Finding meaning.
  • Surrounding myself with a small circle of people that I truly care for and vice versa.

4.  When setting goals for yourself…don’t look back, look forward.


Use what is important to you to set goals for moving those items forward in your life.

I don’t know about you, but I get really frustrated when I hear people say “well that’s just how things have always been done.” It’s a horrible way to do business, create, innovate etc, so why are we approaching our twenties in the same manner?

Try as best you can to create a blank slate of expectations and build on that. Don’t be swayed by the latest Forbes 30 under 30 list or media frenzy over the latest Instagram superstar.

5. Your mom was right… you are special! So act like it.


Seriously though, why would you adhere to measures of success that don’t match your values, believes and dreams!? It boggles my mind how easily some people push aside their own values to align with what is expected of them.

Make your goals personal, and make it about YOU! Selflessness aside, it’s all about you.

For example, here is how I approach what success looks like for me.

  • I have affirmed my life journey by writing everyday
  • I have attained full confidence in my core values, personality and goals
  • I have achieved personal and financial freedom outside of the corporate world
  • I have the ability and freedom to travel when and where I want

6. Do it…now!


Like a baby’s ability to fall repeatedly on its face and be fine, your twenties are a time to experiment, get punched in the face, fall on your ass, time and time again. It’s amazing what you can come back from at this stage in your life, so don’t waste it.

Push yourself to discover who you truly are TODAY. Don’t wait until a middle-life crisis comes knocking to wake you up.

I’d love to hear about what is important to you (whether you’re in your twenties or not!). Email me and let’s chat!

Image credit

Written by Case Kenny

Case is the Founder and Editor-in-Chief of and the host of the New Mindset, Who Dis podcast. Reach him at or @case.kenny on Instagram.

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