The Five Year Plan Question

In high school, my family dubbed college the “c” word. It was banned from family discussions and dinner table topics. Why? Because from the second sophomore year ended until the minute you actually stepped foot on campus, the big fat million dollar question was: “Where are you going to college?” It was easier to answer senior year when the acceptance letter had already rolled in, but junior year… ha, it was like asking for a panic attack. (And how many times did people ask it? 249 times a day.)
I’m out of college and it seems like the new big question is… where do you see yourself in five years.
In job interviews this is a huge question. But other people ask it all the time too. Maybe it’s because my career path isn’t traditional, but I feel like once a day someone makes me declare who I want to be, what I want to be doing in five years. (Although, I’m fairly certain I’m not alone in this!)
I used to really stress out about what I wanted to do in the next five years. The problem with a five year plan, in my opinion, is that five years is a long time. Plans are good and everything, goals are great too… but sometimes it can cause you to steer in a direction that, after a bit of time, isn’t the right direction anymore.
One thing I struggle with is balancing the drive to have, meet, and exceed goals, but to also listen to myself and make the decisions at the right time. Sometimes you outgrow goals. Sometimes you find new passions unexpectedly. I think you have to be flexible enough to say, “You know, maybe this isn’t the direction I want to go in anymore.” (Remember my path to passion post?)
Five years ago, I absolutely never ever in a million and a half years could have guessed where I am today. Ever. It blows my mind how different my life is from what I thought it would look like. Do I love where I am and who I am and what I’m doing? Yes. I think that matters more than where I think I might possibly be in five years.
The five year plan has been on my mind even more. In five (and some change) years I’ll be 30. (Whaaaaa?) And I feel like I’m constantly at a crossroads of different, super different, life paths. I keep finding myself making choices that funnel me down a weird kind of road. I struggle with it from time to time, but ultimately keep making those choices, closing my eyes, and taking leaps of faith.
With the 30 number in my mind, I started questioning if I should be making choices that would lead to a more “white picket fence” path. Oh, it’s been on my mind in the biggest kind of way. Thankfully, I have amazingly supportive friends and family who are behind me no matter what and that means more than anything.
Life is full of changes and unexpected things, but family and friends are the most important constants.
I’ve basically decided to not worry so much about what the next five years holds (picket fences or otherwise) and instead make sure I do everything I can to keep those important to me in my life and to do everything I can to be there for them too. So… in five years, I’d love to have a closer relationship with those amazing people. 

Does anyone else feel pressured to have a five year plan?


PS In case you’re wondering, there are 1,826 days in five years and that’s a lot of time to have a lot of adventures and even change your mind about your future a few times.

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Taylor Cunningham

So agree — I really don't like making long term goals and plans, because while it's good to have something to strive for, I think it can trap you into something that isn't right anymore!


I read a business book that said planning is just guessing. I think that's true in life planning, too. You can prepare for the future, but none of us really know where we'll be in five years.


I completely agree! I'm a literature student and so 'what do you want to do with that degree????' is pretty much the first thing I'm asked when I meet someone new! In five years time, I'll be a year out of university – something I can't even imagine right now!
xo, Amy

Francesca P.

I could not agree more with everything said in here. The endless questions about your future, especially when it came to colleges, were absolutely exhausting. How many times can you answer the same question without questioning it yourself?

Last semester I had to do five year plans for 2 separate classes and it was some of the most frustrating and difficult assignments I've had. How do they except a scared, naive freshman to make such big assumptions about their future lives? At this point, I feel less pressured because I usually just put the question off in general. Whatever happens happens, I think. 🙂 <3


I am a big goal setter and I have 2,5 and 10 year plans. For me it's an integral part of planning the direction I want my life to have, and having a sense of control of where I see myself and my family in the future. That's not to say that plans aren't scrapped or amended – but having a general idea of 'this is where I want to be in 5 years' is important to me. Until I started law school I was very much into going where life took me, but once I started studying I realised that I needed to be more focused on my goals and aspirations – otherwise I was never going to get anywhere except the unemployment line!

Rachel Medlock

I might relate to this post more than any other you've written. I'm a big planner (or was), and it landed me with a degree in a field I fell out of love with long before I switched that tassel on the mortarboard. So, here I am, doing something completely different and baffling every single one of my old friends and family members. Like you said, though, I'm happy with who I am and what I'm doing. And that has to matter more.

Thanks so much for sharing!

Suppose Anything Goes


Since I'll be turning 25 this year I definitely made a 5 year plan. It's a mix of personal goals (own a house) and career goals (be set up financially with a job I am happy going into the long run with). I think it helps keep me motivated.

Doloris van der Bergh

Before I graduated from high school I planned my entire life.
Now I am going to law school (as planned) and I totally failed in my exams this term, which means that I probably have to study one or two semester longer at the Uni 🙁
My plan totally fell apart. I had a huge mental breakdown. I felt like stupid and didm't know what to do (and failing an exam is not really a very bad thing, I am still alive 😀 )

The point is, that planning your life can be very dangerous if something in your list is not going to happen within the time you planned or at any time ever!


I hate the five year plan question with a passion. I feel like it is impossible to know exactly where you're going to be in five years, things change everyday and different choices lead you down different paths and some of the paths are paths I would have never guessed I'd be on 5 years ago I have gone down them and love where I am and where life has taken me. I think everyone has an idea of where they would like their lives to be in 5 years – I'm not gonna a picket fence is involved for what I'm picture for myself in the next five years too. I kind of feel like the 5 year question is along the line of playing make believe – right after college I had a ton of people ask me "where do you see yourself in 5 years" I was kind of fed up with it one and asked s/o twice as old as me where they saw themselves in 5 years and he didn't have an answer so after that I felt better about the 5 year question.


Brittany Lee

I definitely agree with you about the "Five Year" question. I'm graduating college in just over a month, so I have been hearing it WAY too much lately!

An interviewer actually stopped an interview because I told her I wanted to move to New York within the next 5 years. I mean, WHAT?

I mean, I'm super into planning my life, but how can I possibly know what's going to happen five years down the road? It's pretty ridiculous.



People ask me every day what I want to be when I grow up and it freaks me out. I have absolutely no clue where or what I am doing next week let alone five years from now!! So i totally feel your pain.

A College Confession

Deanna D

What a great post! I hate that 5 year question too… The only thing that is consistent in life is change – I have stumbled upon passions throughout my twenties and thirties that would never have fit in a 5 year plan. It is always important to have goals in life but be open to change… that's my 5 year plan 🙂


Gables Girl

I think having a 5 year plan is great…for me it gives me something to work for since that plan will ultimately take me to the next stage in my life

Abbie R

I'm just finishing my second year of university so no many people ask me this question. What I get a lot from my parents now is how long I'm planning on staying in university kind of rushing me through it! It's really stressful!

Ashley Stockwell

I'm facing that same struggle right now. I love to plan ahead and overall I think it's great to have something to work towards. What's hard is when big uncertainties come up. For example I'm engaged and about to finish my Master's but I don't have a job yet. Where I'll live and what I'll be doing in the next two months is constantly on my mind.

Brittany Scancarella

I am such a longtime reader of your blog, and I hardly ever make comments on entries, but the timing of this one literally could not have been more perfect. I've recently turned 25 myself and have had many of these five year plan moments- especially the moment when you realize that you are completely not in the place you thought that you would be. Goals are great, and I value goal setting as something that is so important to my personal development, but have learned that you need the flexibility piece in order to not get yourself down on it. I wrote a similar entry in my own blog (however fledgling of a blog it may be) last night- which is why I felt so compelled to comment. Thats the wonderful thing about growing up in the internet era- we have each other to lean on!

Brittany @


This is exactly how I am feeling right now! I am a senior in high school and have decided to take a non-traditional approach to college, and that hasn't settled well with my family. Holidays have become so stressful because every single person asks a million times what I want to do with my life, and they usually don't like my answer, which is to have adventures and to do the things I love. So, anyway, this was such an inspiring post that reminded me that it is okay to not have my next five years completely mapped out and I am glad to see that others feel the same way.


When I was an undergrad, I definitely had a plan. Maybe not five years, but there was a plan in place. In 2008, life took a sharp left and that plan went out the window. Now, in 2014, I have no idea where I'll be in five years. Sometimes I barely know what the next five days hold. I was forced to take another sharp turn earlier this week and it's been a bit of a setback, but I am figuring it out and making the most of the situation.

All that to say, I'm not so sure such long term plans (5 years, 10 years) are good. I would never have guessed I'd be where I am now. I have no idea what the future holds.

Lauren Rose

I am in college now and I have no idea what I want to do after. I just take it one day at a time and I'm excited to see where life takes me 🙂

Jenn Cramer

I truly hate it when people ask about my future, because even a year ago I didn't know I was going to be where I am today! I can't even tell you if I'm 100% sure on what I will be doing this summer!

amy h @ leopardspot

Great post! I feel like I get this question ALL the time, especially because I am working in retail a year after graduating and people kind of expect it to be a temporary job for me. I want to become a visual manager within the same company, so that end goal is a couple of years down the road. I feel like people are so dissatisfied with that answer, especially after they hear where I graduated from – it's like they think I wasted my education for a brainless job. Ugh!

So my five year plan is to be happy and satisfied with my job (even if I change my career path down the road) and happy with my family, friends, and personal life. I'm keeping it open and not focusing on a particular city or milestones by a certain age – I am a firm believer in what is right for everyone else might not be right for me and that I WILL have to change things in my life and my five year plan to keep myself happy and sane!

xx, Amy @ leopardspot (the blog)


I feel pressured to have a five year plan! I start college next fall and I know where I'm going, so thank goodness answering the question "Where are you going to college?" is no longer a cause of anxiety, but now that I'm about to go to college, the new questions are "What do you want to major in? What do you want to do?" and I have no idea, because I'm interested in so many different things! Hopefully I'll have a better idea of what I want to do when I actually go to college, but for now, I am content with the fact that I know the world is a rapidly changing place, and that the career I end up choosing might not even exist yet! -Audrey | Brunch at Audrey's

Laura Nelson

I really needed to read this today! I've been super stressing myself out lately about the next several years (graduating, grad school, moving across the country for said grad school, etc). This was great to remind myself not to worry so much. I'm confident I'm headed in the right direction so I should just let it go somewhat. Thank you!


i agree, goals and dreams change! and, I used to make long-term plans like crazy, but somehow things never worked out the way I wanted them to, leaving me very frustrated… I have a general idea of where I'd like to be, but leave the very strict planning for what it is and focus on what I'm doing right now and say – the next year or two.
xo, cheyenne