Surviving the Inescapable Existential Dread of Your Late Twenties

I never really pictured myself in my late twenties. I pictured myself graduating college ( aged 22), and getting my ‘good job’ (aged 24). Sure, I imagined that I’d somehow be vaguely ‘rich & successful’, but I couldn’t actually project how I might feel or what I might be doing. 

I know now that it’s because the hopes and dreams society tends to prioritize for us are expected to have come to pass by this time. Whether you were expected to be financially successful, have married and started a family, or anything else, the assumption is that you pretty much have your life on track by now.

Which means, one of two things happens to you: 

  1. You haven’t achieved the goals expected of you by now and you consequently feel a little bit like a failure.

OR

  1. You have achieved the goals expected of you and now you’re wondering what the hell to do with the rest of your life. 

Either way, you have the feeling that you’re not quite doing what you should be. And on top of it, you don’t quite have the feeling of having all the time in the world to take risks anymore. You’re starting to make the switch between having nothing to lose to having, well, maybe some things to lose. 

You also have the cacophony of what everyone else is doing. We now have the unfortunate ability to compare our lives with anyone, anywhere. We’ve never had more people to compare our perceived failures or successes to.

On top of all of that, is that every time you muster up the courage to try something, for every gentle voice of encouragement, there seem to be ten more screaming at you that you’re doing it ‘wrong’. You’re investing wrong, applying for jobs wrong, working out wrong, your hair routine is wrong, your taste is wrong, and it’s confusing. 

And exhausting. It’s exhausting not knowing what you’re doing. It’s more exhausting not knowing what you should be doing. It’s terminally exhausting to not know what you actually want to do. 

That’s where I find myself lately. Exhausted and worried that this is all there is. 

The other day, someone asked me that classic question - what would you do if time and money were no longer objects? - and I didn’t have an answer. Nothing sounded good enough to be doing. I could so clearly see the flaws with any idea that came to mind. In that moment, I didn’t believe anything could make me feel purposeful and happy. 

I still don’t. At least, for now. But I’m trying to get through it. 

I’m doing 3 things that seem to be helping: 

  1. Reminding myself that this feeling is compounded by seasonal depression, anxiety over massive layoffs in my industry, a period of high stress and grief in my life, and the fact that the world is still kind of awful right now. 

  2. Seeing people. Letting them make me laugh. Letting their ideas in. New perspectives always make me feel better. If there is one thing I feel sure about, it’s that relationships are always worth it.

  3. Setting aside time for ‘creativity’. I use this word loosely but basically setting aside time for myself to explore things I might like. Today, I had the overpowering urge to write this article, yesterday it was drawing. The point is that there isn’t necessarily a point to them.

That’s all I’ve got. You’re not the only one feeling this way. We’re transitioning to a period of life that is so much less defined. While that is terrifying for all the reasons I described, it is also freeing, and I have to choose to hold onto that. 

Sunset in Milos, Greece