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

Holland Dombeck McCue Career Paths, Change, Holland Dombeck, Interviewing, Millenial Voice

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?