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  • Writer's pictureMonica Montanari

How To Re-Evaluate Your Life As a 20-Something

It's a big decade full of a lot of changes.

In your 20's it's likely that you'll graduate, get married, buy a house, have a kid, buy a new car, start a company, make a million dollars, the possibilities are endless. It's (hopefully) the age where a lot of dreams come true- the goals you have had since you were 10 years old are finally realized. Everything you've worked so hard for is suddenly, well, done.

It's an amazing feeling, don't get me wrong. But it has a way of making you wonder...

Now what?


It's a feeling that I've experienced personally- and many other 20-somethings I've talked to feel it as well. You get out in the real world and it just hits you like a ton of bricks. It doesn't matter how prepared you thought you were, you're not ready. Wake up call.

Toto, I've a feeling we're not in our teens anymore.

There's a definitive moment when you realize that you might not be the queen or king of the world- and it's a rude awakening. You think you're different and more special than everyone else. I mean, hey you are- but... so is everyone else. When everyone is equally special, it becomes normal. We become desensitized to it. Remember reading The Giver in middle school? Okay so enough on that depressing rant, you get it. The point is: welcome to the real world. It kind of sucks. Whether you did before or not, now you have to pay bills, pay off loans, schedule your own appointments, do your own laundry, and feed yourself amongst other things. Adulting is rough.

So at some time in their life, everyone reaches this point- and it's a rarely talked about but crucial part of your development as a human being. It literally determines who you will be for the rest of your life.

Will you be on autopilot just working to pay your bills your whole life and then die? Or will you allow the give-and-take to stretch you beyond your comfort zone- and probably your limits- and remain driven with a lust for life, even though you might not know where it's going?

Hopefully the latter. But that means you're going to need to pick yourself up, dust yourself off, and start (almost) all over again. But how? It's a process I've had to contemplate for a while- so I'm laying out the blueprint here in 5 steps for you to try yourself.


Take a step back and look at your values.

This worksheet is a great way to start. In order to prioritize your life, you first need to know what is truly important to you. This worksheet gives you a lot of options, so you don't have to try to make things up out of thin air. Plus, it helps you narrow down your values to the top 5. Love it. I've done it time and time again and it always helps me to figure out who I am.

Find out what kind of person you are.

This website allows you to not only discover what your personality is like in the Myers-Briggs metrics, but it also allows you to explore each of the 16 personality types in depth to discover the strengths, weaknesses, career paths, compatibility, and other facets of your personality. Keep in mind, though, that there are a million types of Myers-Briggs tests out there- so if you want an absolute, definitive answer, I recommend you complete another one and average the results. Even if you've done this before, the average human has a shift in personality every 4 years- are you the same person you were back then?

Lay out your priorities.

I like to do this in two steps.

  • Step One: List out how your priorities really are. Be honest with yourself. Don't pretend like you value your family more than your work if you miss out on family events to go to the office. Be realistic. This article has a pretty basic but inclusive list of things that might be on your list. You can totally go through his whole process, but if you want to save time, you can just look at the questions he poses for each priority, ask yourself how much time you spend on each, and consider where each priority is in your life.

  • Step Two: List out how you wish your priorities were. Ask yourself this: "When I die- at the end of my life- what do I want to be remembered for? What is really important to me? What do I wish I spent more time on, or placed more importance on?" Take those questions, and next to your first list, write a second of your ideal prioritization.


This is quite possibly the hardest part. So you have those two lists. They're side by side. Chances are, there's going to be a divide. What you wish was number 1 might be sitting at number 5 right now. Pick 3-5 priorities you actually want to rearrange- not the ones you think you should, but the ones that you personally would like to change for your own happiness.

  • Figure out how to cross the divide between those 3-5 things. Brainstorm little ideas. This article suggests a few things that are realistic and can help. If your career is one of them, there's a concept I learned that is very similar to the Japanese idea of Ikigai ("your reason for being"), and it looks like this:

Set Goals

Now that you know what you value and who you are and what changes you'd like to make, sit down and make some goals. I know, easier said than done. Here's the deal. Don't you dare think to yourself "I would do that if that was realistic". You are not allowed to limit yourself. For just this once. Now's not the time Debbie Downer. But get out a real, physical piece of paper and think about it this way:

  • You've lived a long life, and you're laying on your death bed (hey I have to get you to take this seriously!). You're surrounded by your family and friends, and before you go, you close your eyes and envision the things in life that have made you the most happy. I know it's obscure, but just go with it. What do you want to be able to say you did? What do you have to be proud of? These are your long term goals. They might be a little cloudy and vague, but they're something.

  • Rewind...oh.... 50 years or so. You're 40. What goals do you want to have realized then? Some of them will probably be leading to the ones you want to have accomplished by the time you're 90, but some might be different. You can afford to be a little realistic here. But not too much. You still need to let go of those self-imposed limits and allow yourself to dream.

  • Alright. Now you're 30. I'll let you be even more realistic. What do you want to have accomplished?

  • You have how many years until you're thirty, and how many goals to accomplish? (It's okay if the numbers aren't even). What are the stepping stones you'll need to reach those goals? And the stepping stones to those? As you can see, working backwards we're allowed to be more realistic, the closer and closer we get to today.

  • By a certain date next year, what do you hope to be able to say you have achieved?

  • What can you do in the months leading up to that to ensure it happens?

  • Alright, what about this month?

  • This week?

  • Today?

That's it.

Take a deep breath. That wasn't so bad, and hopefully you now have more of a sense of direction in your life. You're ready to put one foot in front of the other again and continue moving in the right direction- one day at a time. All you need to do is brush yourself off and tell yourself: "You got this."

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