Where do you see yourself in five years?

Where do you see yourself in five years?

This is a question that comes up time and again on job interviews. It’s one that I’ve always answered honestly, but never managed to do so accurately. Do a simple Now & Then between EOY 2015 and today and you’ll see what I mean. I didn’t even get the continent right.

And I’m not the only one. The last time I talked about the absurdity of the five-year plan, I was sitting in a café in Zurich with a fellow American. She had been hired in Boston to work in a consulting firm, but then unexpectedly got transferred to England to cover someone’s maternity leave. The assignment was for one year but she stayed for three.

“This is what I mean,” I complained. “How could anyone know that would happen? I mean, could you imagine if you sat in that interview and said, ‘My five-year plan is for the company to pay me to relocate to Europe, promote me two times and then put me in charge of a program.” I laughed, adding, “Well actually no, let’s be clear. That’s just the first three years.”

I’m pretty sure the interviewer would have called security. And so would my last employer if I had answered her question about my five-year plan by saying, “I see myself in this position for two years—tops. I’m going to move to Denver and write a book… UNLESS you can offer me a version of this job where I can do it from anywhere in the world during the hours of my choosing. I would be interested in that. But only if you could make it happen within the next six months. Oh and I want to make 20 percent more than I do now.”

I understand that my circumstances are extreme. But, at the same time, I don’t think it’s unusual for the recent past to look drastically different from what you once planned. I mean, consider your career back in 2015 and try to tell me that what happened since aligns to the plan you had in your head, let alone the one you would admit to during an interview. Tell me how nothing came up along the way—no personal circumstances changed, no unexpected professional opportunities arose, nothing at all tempted you to shift priorities.  Try to convince me that even if you did follow your plan to the letter and it all worked out great, that you’re not left wondering if maybe you didn’t set your sights high enough.

But that conversation I had was back in 2016. I’m older and wiser now. Two years on the road and one European relocation later and I am no longer laughing at the absurdity of the five-year plan. Instead, I see the question for what it is: a trick.

I believe there are three main ways to answer that question from a would-be employer:

1) With high-reaching goals about building something up and bringing revenue in.

2) With careful optimism about how you expect to swing from one rung of the middle management ladder to another, slightly higher rung on the middle management ladder.

3) With a sprinkle of personality about your lifelong goals or ambitions—be it writing a book or working abroad or having a family or starting a business or running for office.

I think the first two answers are equally disposable. By and large, the interviewer doesn’t really want to hear about what you think you’ll do once you’re in the door because he or she already has a pretty good idea of what that is. You can change their mind, but not today and not with words.

Instead, I think the five-year plan is a way to see if people will admit that they have interests and ambitions outside of work. This goes double for women. Everyone wants to know our short-term plan because you know what they say about plans… something about mice. And men. And that, I think, is what the interviewer is really trying to get at with me and people like me: Does a man factor into your next five years? By extension, how does a family fit in?

Nowadays, that’s the reason why I bristle when I get the five-year question. It’s because I recognize that the interviewer is speaking in code. They want to know if I have children—and, if so, how many and how old? As a matter of follow-up: Are they in daycare? How flexible is that service provider? While we’re at it, how flexible am I? If a deadline falls on the same night as Little League playoffs, which would I pick?

I know, I know. There are laws preventing interviewers from asking those questions directly and discriminating against candidates for bringing up their children of their own volition. Try not to explain that to me in the comments. Because I know that and so do they. That’s the point. They’re asking in a roundabout way, through five-year plans and free-time hobbies, to see if I’ll show my cards. I don’t have children, as you all know. But my future employers don’t know that and I intend to keep it that way… even though it would probably count in my favor if I bragged about how my calendar is free of OBGYN appointments and childcare emergencies. I keep my answers strictly professional. And I encourage all of you—men and women—to do the same. In solidarity.

Also, while I’m on my Caveat Box, allow me one more. I know things are changing for the better. That employers are coming around to the idea of treating employees like adults and recognizing that adults are also human beings! But still. Things are not very good. For every example I hear of a flexible work arrangement, there are ten horror stories that could be shared. Besides, I think we need to acknowledge that workplace flexibility is usually granted to people who are outright indispensable or have a specialized skill that’s hard to come by. I should know. I certainly couldn’t have done my job from New Zealand if there were 50 people willing and capable of doing it from New York.

As we head into the holiday season and have occasion to chit chat with people whom we don’t see all that often, I offer this advice: when asked broad strokes questions about career goals or life plans: Go big. Be honest about what you want and say it loud. Don’t be alarmed if it sounds ridiculous. I am living proof that life is insane—and that anyone who tries to convince me otherwise is lacking imagination or ambition… maybe both. If they heckle you, keep your chin up. Make a list of five examples from the past five years about things that were not in the plan but were still pretty amazing. Remind yourself and anyone else who needs it that progress is still progress, even if it’s accidental. And then go home and go to bed. Because you’ve got big plans to get to.

7 comments to “Where do you see yourself in five years?”
  1. Very good advice! It is important to have dreams and plans. Yes, stuff will happen in between, but often that makes The Dream even more awesome.
    Had I known with 25 that I will live this great life at 50 I would have been more relaxed about things.
    Go big and be outrageously optimistic!

    • AMEN! I am saying the same thing now, except that I am 37. On one hand, I know that working like a maniac at 25 set me up for later in life. On the other, I wish I didn’t take myself so seriously in the process. I’ll never get those hours back and I feel like i missed a good part of my 20s just slaving away… I still work hard today, but it feels different. Maybe it’s not so much having a 5 year plan but having a 5 year priority. I’ll figure it out, maybe when I’m 50. xx thanks for reading!

  2. In five years I expect to have all my windows finally in curtains, I expect to be able to finally remember how to dim the lights on the car and make the windshield wipers function when needed. I plan on keeping the cats I have and maybe enticing a few more my way. And most importantly I expect to be five years older, maybe a bit wiser, and a bit more forgetful.
    Ain’t life grand.

    • life is grand when you put it that way! xx. thanks for reading and I completely agree… i hope my house becomes a home full of cheer and fur and climbable window treatments in the next five years. i’ll be older too, but none the worse for the wear. xx

  3. Whenever I get this question I usually cheerfully respond with “I have absolutely no idea,” and then back it up with exactly what you’re talking about. I, of course, mention career dreams and whatnot, but I don’t believe in five year plans. I barely know what I’m doing in five hours.

    • one of my co-workers always used to tell me “assume kindness always.” so when i get a question i think is snarky, don’t jump to that emotion…that’s in my head, not theirs. I don’t know what that says about me that i don’t quite believe her, but i do think she has a good point. and so do you. a cheerful “who gives a F!” goes a long way. xx

  4. when we first got married, we lived in a small apartment complex. not ideal, but doable. If someone had told me in five years I’d be living in house trailer in the middle of the woods, because there was a house there with no plumbing, no electricity, no heat, and a foundation that was tilting the house into rubble, I’d have laughed them out of the room.
    I’m still in that house,48 years later. We have indoor plumbing now. And cats. And not a regret in the world.
    I guess what Im saying is, and I know you know it too, there’s no way you can know for sure where you’ll be or even why you’ll be there, in five years, or two, or ten. It just happens.

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