Why I’m Glad I Never Made a 5 Year Plan

spring outfit inspiration

TOP: Silk Pocket Blouse | SHORTS: Striped Drapey Shorts | SHOES: Brezza Lace Up Flats | BAG: West 57th Color-blocked Carryall

I’m always impressed with people who have made a five year plan. That they’ve managed to think that far into the future. You know what you want and you made a plan to get it — props to you! The furthest I can realistically think out to is about six months… maybe. I suppose I’m just not Type-A enough to follow through on making one and then actually sticking to it.

But on the flip side, the past five years have made me happy that I never made a five year plan because what I thought I wanted then is definitely not what life had in store for me.

summer street style
silk blouse and striped shorts

 
casual summer outfit

I think about what my five year plan may have looked like (if I had made one) when I first graduated. It most definitely did not include moving to Chicago, starting my own business or blogging part time.

It probably would have included getting married, buying our first home and maybe a promotion if I worked in ad agency or design firm like I thought I might. There’s nothing wrong with any of that, in fact, they’re all pretty great, but man, would my plan have been instantly ruined on the day Rob told me he got a job in Chicago.

My decision to move with him was a pivotal one for me. Yes, I was scared, really scared, but knowing he was there made it a lot easier.

striped shorts and carry all tote
striped short and west 57th carryall

 
striped shorts

balayage hair, lob
striped shorts and silk blouse

 
I remember the day he called me and told me about his new job. I was driving back to work from my lunch break in my dad’s giant truck (my car was in the shop) and after we got off the phone, I sat in the parking lot, sobbing. I was so excited for him and his new job, but terrified for myself — what would happen to us? what would I do for work? how would I make friends? It was also a small miracle that in my emotional state, I managed to not crash my dad’s car.

There were some trying moments in that first year or two after I moved to Chicago. I worked alone from home and I didn’t know a lot of people, but eventually I got Oliver, got out of the house more and made friends — really really amazing friends and so many cool creative people — like Julie who took these pics — who inspire me and make me more thankful for my job everyday. Was any of that in a five year plan? Of course not.

striped shorts

blogger street style
carry all tote, striped shorts

 
But life is full of curveballs and I’ve learned to let go a bit and that being open to change isn’t as scary as it seems. For me, not having a five year plan has been better than anything I could have ever planned, so for the next five years? I’m just going to see what happens!

Will we own a house? Will we have children? A furry brother (or sister) for Oliver? Will I still be writing this blog (I hope so!)?

The truth? I have no earthly idea, but I’m okay with that.

So, no, I don’t have a five year plan and frankly, they scare me a bit! Not that I’m a ‘fly by the seat of my pants’ kind of girl, but planning the next five years based off what I know today?!

I just can’t.

That being said, I don’t think there’s anything wrong with a five year plan, I just don’t think it’s for me.

carry all tote, striped shorts

spring outfit idea
casual summer outfit

 
But if you do have one, what happens if the timeline of your plan doesn’t match up to reality?

It makes me wonder — if we have our lives so planned out, do we miss out on opportunities that come up along the way?

I can only imagine if I had decided not to move to Chicago back in 2012 because it wasn’t in ‘the plan’. I’m not sure I could have ever planned anything as great as what has actually happened. Sure, there were bumps along the road, but so far, it’s all been worth it.

Do you have a five year plan? How has it played out so far? Do you allow yourself to edit the plan when things come up? If you don’t have a plan, I’d love it if you shared one good thing that’s happened in your life that you could have never planned for!

Photography by Julie Kennedy

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