Where Do You See Yourself in 5 Years?

For those of us who didn’t start out in the entrepreneurial world, this was the dreaded question on every single job interview. 

For those of us who are entrepreneurs and own our own businesses, I’m sure we ask this question on a weekly basis of our employees and potential employees.

I get it.  We all need to have a vision, have short term and long term goals, and ultimately portray the “entrepreneurial spirit” and attract talent that complements our vision.


I think this is the dumbest question to ever ask because there is never a right answer. The talent I want to attract as a business owner is someone who answers the question with…

“I want your job. I want to start my own company and be a startup success.”

But then, if someone does answer the question that way, how do you make the justification to invest time, money, and mentorship into that person?

So why do we ask this question? What is our reason and purpose? Is it simply to get to know that person on a deeper level? Is it to understand someone’s intrinsic and extrinsic motivations? If the answer is yes, then I challenge you all to try for just one month to change the question to this.

“In the past 5 years, what have you done and what has happened in your life to you get you to where you are now? “

Because now you’re not just asking them a question, we’re are making them take action and reflect on their actions!

By changing the question in such a simple way you will instantly get a deeper understanding of who they are, where they come from, how hard they work, what their passions are, and what motivates them.

So, I took it upon myself to practice what I preach. Here are the Top 5 Moments in the past 5 years of my life that have gotten me to where I am today. 

And the funny thing is…

Had you asked me 5 years ago, “Where do I see myself in 5 years?”, none of these moments below would have come out of my mouth, because the truth is, you never know where life is going to take you. I’m not saying don’t have a vision, don’t have goals, don’t have purpose. I am saying you can’t predict what will happen to you 5 years from now. I do feel it’s important to plan, to set goals, to take the right steps and actions each day to build up to where you envision your life in 5 years. But for the sake of job interviews and acquiring the right talent for your company, I think it’s time to throw out the dreaded question. 

1.     Little Joe O’Connor came into the world. Exactly 5 years ago tomorrow on March 14, 2010, my nephew, Joey, was born and I became an aunt. Not having children of my own, this is as close as I’ve come. My sister is my best friend in the entire world. I would do absolutely ANYTHING for this woman and when she came to me 5 years and 8 months ago to tell me she was pregnant (out of wedlock but with an amazing man) at 23, you would of thought my world was over. Who was I going to go out with? Who was I going to double date with? Who was not going to be living in a Baltimore City apartment with me like I had envisioned?

God. How selfish. How immature. Having my nephew and having a sister that I look up to every single day for the mother and woman she is, is the best thing that has ever happened to me in the last 5 years.  I learned a lesson in how being selfish will get you nowhere in this world and how sometimes the most unexpected things in life are the greatest gifts

2. Big Joe O’Connor left this world.  In August of 2013, little Joey’s dad, my sister’s fiancé, and one of my very best friends in this entire world, left this world. It was awful, unexpected, horrible,  sad, and it still is. But you can’t cry forever. You find strength inside of you that you never knew  you had. You use these moments to fuel the fire inside you to be the most amazing person and  you can be. You use these moments to realize “What in the world am I waiting for?” Get out  there and make something of this life - this short life we have here.

3.     I found a business partner in a friend. In 2011,   after spending 6 years working alongside a good friend, a past roommate, and amazing teammate, my business partner, Rachel Robinson and I started a dream of building our own event company. We were in San Francisco, CA running an event for the corporate company we worked for and although life was good, we had great paychecks, and traveled the world together, we realized we both had a vision that was much greater than where we were. After much more talk, a few cocktails, and sharing our “Where do we see ourselves in 5 years” dreams, Intrinsic Events was born. 

4.     The Ultimatum. A little over a year ago, the corporate company Rachel and I worked for gave us an ultimatum. Although we were always proactive and transparent in our life goals with this company, and were often complimented on our “entrepreneurial spirit”, it became apparent that Intrinsic Events was our passion. We were challenged on our loyalty and priority with the company and ultimately given a choice. Either stop doing Intrinsic Events or get out.  Needless to say, we got out and never looked back.

5.     Today. Reflecting on the Top 5 moments in the past 5 years today is one of the greatest exercises I have ever done personally and professionally. Putting it out there for the world to read is a different story. But as my beloved Michael Jackson would say, “If you want to make the world a better place, take a look at yourself and make a change”. So that’s what I did, that’s what I’m doing and I hope that we can all make a change to stop the dreaded question of “Where do you see yourself in 5 years?”

My Challenge

Please take just 5 minutes today and reflect on the Top 5 moments in the past 5 years thatgot you to where you are today and share it with this amazing community of entrepreneurs we’ve built here by commenting below. I promise you will be so happy you did. 


Jessica Gignac

Jessica Gignac thrives the thrill of the creative process that goes into building events for success. Independent and introverted at heart, when she isn't producing amazing events, she is on a never ending quest for her next great laugh, adventure and dirty martini.