Where do you see yourself in 5 years? (This question is the pits.)

If you told me at 23 that I’d be spending my St. Patrick’s Day weekend debating paint samples and watching The Talented Mr. Ripley on Netflix with my dogs, I probably wouldn’t have believed you. Why? Because this is what I was doing 5 years ago:


  • House party.
  • Green beer.
  • Utterly clueless on where I saw myself in 5 years.

But as I was applying for jobs my senior year of college, it never failed that I was asked “Well Holland, that’s great, but… where do you see yourself in 5 years?”

In hindsight, maybe the question was more a test of my ability as a Marketing major to magically weave BS into a sales pitch, but even 5 years later I still can’t answer this one. I’ve read that Millennials pretty much suck in terms of career motivation and direction, so maybe I just fall into that bucket…


Maybe the question is flawed.

What I could answer, is “What do you need to do in the next 5 years to to get to where you potentially want to be in your career?”

What I knew at 23:

  1. In 2008/2009, the economy was in the tank.
  2. I had a pretty solid thing going at Walgreens–manager of people, decent salary, HMO, fully vested in my 401K.
  3. I wanted to get out of retail ASAP and work in my field of study.
  4. Most of the stuff I learned about “marketing” in college was not enough to land a job with a “marketing” track.

What I knew I had to do in the next 3-5 years:

  1. Figure out how to gain experience without having any “real” experience.
  2. Spin the experience I did have (Walgreens + a stint slinging FSU-themed Crocs + some volunteer work) to show that I was worthy of gaining that “real” experience.
  3. Google the crap out of Web 2.0.
  4. Be prepared to pivot.

Where I ended up after 5 years:

  1. 2 years of working retail post grad. Stacking cash. Paying off my car. Reading. Self-paced learning. Networking.
  2. 1 year of interning at 25 hours a week while working 40 hours a week to pay down my student loans (because I knew a pay cut to change industries was on the horizon).
  3. 2.5 years in a pure play B2B role at an agency with inspiring leadership.
  4. Pivoting.
  5. Debating paint samples and watching The Talented Mr. Ripley on Netflix with my dogs vs. drinking green beer with my ladies.

I probably would have gotten a job offer a lot sooner if I had played by the rules: House, corner office, possible MBA, managing something—sure, that sounds like what they want to hear.

But in my opinion, it was more important to know how to get from point A to point B vs. detailing hypothetical aspirations.

Oh, and if you haven’t already, download timehop and you, too, can track how much time has lapsed between green beer and paint samples.

What’s your least favorite interview question? What is a better question to ask in its place?

FOT Background Check

Holland Dombeck McCue
Holland Dombeck McCue is the former the Editor turned blogger here at Fistful of Talent. She joined the group in August of 2011 and launched FOT's podcast, The CYA Report, and monthly webinar series. Now she gets to participate in all the HR/talent pundit fun. Check her out on Twitter via @Holland_Dombeck.


  1. Kris Dunn
    Kris Dunn says:

    I think the better question isn’t where you see yourself in the next 5 years, it’s:

    What have you done in the last two years?

    Inspire someone to hire you. Were you just doing what was expected or were you actually attempting to create some value?

    Ballers ball, get bored and start doing shit no one asked for. Like the time HD started walking in to business to sell bulk account flu shots. You don’t see a lot of retail managers doing that.

    And yes, HD – you’re becoming all growns up like my man Mikey – http://www.youtube.com/watch?v=GEGiVaXpj94


    • HD says:

      So wise. Post in itself:

      “What have you done in the last two years?

      Inspire someone to hire you. Were you just doing what was expected or were you actually attempting to create some value?'”

      Not all grown up 😉 Still just a clueless Gen Y’er with too much caffeine in her system.

  2. Nicole Norris says:

    Love this post.

  3. This a awesome, being a younger gun myself this really hits home. You’ve given me some great ideas and pointers on how i can make myself more experienced without having a 5 page resume.

  4. Annie says:

    As a recruiter, I ask this question I am trying to measure the fit of where the company is going to be in 5 years and where you see yourself. The question is about succession planning…where will you fit into the company in 5 years? What do you plan to do to get there? If you have no idea where you want to be in 5 years most likely you need to do more research about your industry/job values. If you have a plan it can certainly change but it shows you’ve thought about the future

    • HD says:

      Annie, thanks for the feedback. I think we are speaking the same language. The point I was trying to make is that you need to have the plan, not the destination. Most people only have the destination (point B) in mind, but aren’t really sure what to do to get there; especially when they are a new grad. In today’s constantly changing job market, I would also want to know that candidates were open to the idea of pivoting vs. having a single track career mindset. Also, if you pass on a candidate because they don’t want to be part of a succession plan, you may miss out on some great talent who can do more in 3 years than someone else could in 5+.

  5. Janelle says:

    I hate the question “what is your biggest weakness” every time I have to answer that I cringe.

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