Considering a Career Reinvention? Three Questions to Ask Yourself

This article was originally written for and posted on Beyond Mom.

For many of us, a career reinvention is something we dream of doing but the thought of pivoting from our current path seems at the very least, impossible. A quick scan of my resume will reveal to you the many hats I’ve worn throughout my career to date. One of which includes a 4-year track as a wedding & portrait photographer. At the very least, my unconventional career path makes for a great conversation piece at networking events and media interviews. I will be the first to admit that my career path is nothing short of a squiggly line rather than a linear path. Having reinvention as part of my career story, however, has created a multidimensional layer to my body of work that I wouldn’t otherwise have.

In my work as a coach, I often meet with clients who have built their career in a particular area – law, finance, sales, etc. – and things are going well, yet they aren’t because they realize it’s not their ideal path. I find that those who fall into this category chose their profession mainly out of practicality and stability.  

In a world where things are moving rapidly, brands are reinventing themselves, and companies are changing direction everyday, one can argue that the new idea of job security is one’s ability to reinvent. Whether you’ve worked in your particular field for ten years, run your own business, or you’re a stay-at-home mom who’s ready to re-enter the workforce, a career reinvention is possible and in some cases critical to one’s success.

A few reasons why a reinvention might be a good move for you:

  • It gives you an opportunity to redefine yourself and leverage your skill set in a fresh and engaging way.
  • You can take on a new career direction that brings you more meaning and fulfillment in your work.
  • It gives you the chance to recreate a life and career based on what’s important to you i.e. freedom, work-life balance, creativity, etc.

So if a career reinvention is so great, why aren’t most of us doing it?

What makes a reinvention particularly difficult is when we have reached a certain level of success within our career path and built a solid reputation from it, deviating from that path seems illogical or even foolish. The biggest mistake I see is when we fixate on the wrong questions at the beginning of our contemplation. We may get stuck pondering: What will others think about this? What if it doesn’t work out? What if I don’t know enough? Will I have wasted all those years doing what I’ve always done? This line of questioning causes us to doubt our abilities rather than see this junction as an opportunity to grow professionally.

A quote from the Harvard Business Review : “We judge ourselves by what we feel capable of doing, while others judge us by what we have already done.”

If you’re at a career crossroads and reinventing yourself is on your mind, here are a few productive questions to ask yourself:

What do I want? And Why?

When you know what your bigger vision and ultimate destination looks like, a career reinvention will help you qualify whether it will add to this vision or take away from it. Tie your career decision back to your values, your sense of purpose, and what is important to you. Ask yourself why you want to create this change in your life and career right now. Make sure that your answer comes from an authentic place and aligns with your sense of purpose.

What are the tradeoffs to changing my career course?

Am I willing to deal with them? Inevitably there will be gains as well as losses to making a change. If you are a finance executive looking to start her own business in the health and wellness industry, identify the adjustments you may encounter as a result of this choice. Will a possible reduction in salary be offset by greater freedom, flexibility and sense of purpose in helping others? Be honest with yourself and be open to the different ways a career reinvention might add to your overall quality of life.

What resources do I already have and what do I need to know to make this career reinvention a success?

Time to take stock of your skill set, transferrable skills, personal & professional experiences (i.e. volunteer work, completed projects, education etc.) Your network and connections can aid in building your confidence and credibility. Your own life and career experiences can be used to your advantage to get your foot in the door.

A career reinvention is a prime opportunity to tell a compelling career narrative. When told well, your story will give you an edge to intentionally and strategically create the next evolution of your career. Start by asking yourself these questions and redefine yourself for the next chapter of your career.

Let me know how it goes.


To get additional support on your career journey, email to learn more about our Dream Discovery 1-on-1 sessions.

[Photo: Flickr user M Yashna]