The Five-Year Plan

My headspace is a weird one right now. I’ll just go ahead and preface this post with that. I’m 24, so I’m almost 25, so I’m trying to reconcile where I thought I would be at this age with where I actually am. I’m trying to decide if where I thought I would be is where I now want to be–generally, that answer is a resounding no.

I’m pretty sure I’m at The Age where you’re supposed to have a five-year plan. When you walk into a job interview after college, they ask you what your dream job is (and I don’t think Professional TV Watcher is what they are looking for). I don’t like to give a concrete answer to that question, not really. I mean, hopefully you’ll hire me and in five years I’ll still be working here, but that reeks of a little desperation. Since we live in an age when every entry-level job wants you to have minimum two to three years of related experience, the expectation that you’ll have a five-year plan is not a surprise.

But in my experience, having a five-year plan doesn’t mean delineating every step of the way, right down to the cookie-cutter lifestyle that has been spoonfed to our generation. Having a five-year plan means knowing what kind of person you want to grow into and what roles you should put yourself in to get there and knowing how best you can promote yourself to make that happen. It’s about knowing what kind of environment you thrive in, how you can manipulate your strengths and weaknesses to your advantage–it’s about knowing yourself, ultimately.

I mean, think about where you were five years ago. If you were like me, you were in the early to mid stages of college, which means you were definitely thinking about what you wanted to do after graduation and what your career was going to be and how living in your own apartment for the first time was going to be totally awesome.


Five years ago, I was nineteen years old and about to embark on a study abroad across China, Japan, New Zealand and Australia. I was an English Education major. I had just met someone who I thought I was going to probably date for a really long time. I had started writing my first novel. I was all set to become a suburban superstar. Maybe in another life, that would have come true.

Instead, I’m living in an apartment in Brooklyn, working several jobs to make ends meet, and nowhere near my “dream field” that I’ve been preparing for since middle school. And, really, I don’t care. Because that isn’t my dream job anymore. I’m starting work at a start-up on Monday, and I can’t be more excited. I’m just one of those single girls, living it up in New York City, and life could not be better. Five years ago, I had no idea this was what I wanted to do. But now that I’m here, I can’t imagine doing anything else.

Just don’t take yourself too seriously when it comes to future plans. It’s okay to set some things in stone, but always leave room for change. Always be flexible. Grow so much as a person that every five years you can look back at the last half-decade and wonder how you ever thought you were content with who you used to be. Keep hold of who you are, but don’t be afraid to grow.

Growth is about taking leaps of faith, after all.

Please note that I am a 24-year-old blogger, not a professional life advice-giver, so take this post with a grain of salt.


3 thoughts on “The Five-Year Plan

  1. Amen to all of this– so much of it resonates with me. Now we super-need to catch up, and soon– I want to hear details about this new job! Excited that good things are happening for you, sweets 🙂

  2. Ummmm, yes to this post. We knew each other pretty well 5 years ago and I think we were both on the same track. I wanted to be an English teacher, and instill all kinds of crazy lit love on those students. They wouldn’t know what hit them. Also, if my 5 year plan had worked out, I would be married to an engineer and crankin’ out them babies by now. Well, actually I had just met Scott, but you were with me via email for that whole process. 🙂

    Love you, Bailey! Love this post. I’ve loved being your friend through this whole journey of growing up. From Impact to NYC, we’ve been friends, and I’m so grateful. I’m also grateful our 5 year plans didn’t work out–me+babies right now? No thanks. It’s crazy how life works itself out and we’re better for it. [Also, sidenote, that post about math and science? HOW ARE WE EXACTLY THE SAME?! I am always amazed at how similar we are.]

    I’m so glad you’re loving your life! When you come back to OK we need need NEED to catch up!

    • Kayla, I totally agree! I feel like when we were 18 and watching High School Musical in your dorm room, it seemed like the world would just *fall apart* if things didn’t happen exactly the way we imagined they would. It does seem like both of our lives have changed SO much from that original plan, but I know we’re both so much happier than we would be if it had happened “the way we wanted.” MISS YOU A LOT and when I come back later this year for a visit we will DEFINITELY catch up.

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