Career Pivot: How to Evaluate Your Idea, Cook up a Plan, and Activate

Are you currently feeling flustered by a career transition? Have no fear, JobJenny is here!

Our recent Professional Development event featured Jenny Foss, career expert and Founder of Jenny provided attendees with a plethora of insightful tips on what it takes to tackle a transition in your career.
April Professional Development Event

Making any type of professional change can be quite overwhelming and confusing. And when you’re looking to shift into a completely different industry or position, it’s even MORE overwhelming. A career pivot often takes a detailed strategy, can require additional schooling, and sacrifices of your time, energy, and money.

Although transitioning into a new job can seem daunting, the process will go much smoother if you follow these tips…

Ask yourself these questions

  • What’s my end game?
  • What are the major milestones?
  • What does my to-do list look like?

Think of where you want to be in six months. This provides you with a good amount of time to realistically plan your transition and to make genuine progress.

Next, you will need to make note of any specific milestones. For example, the career pivot may require you to further your education or obtain a specific licence. If you’re in need of sharpening a specific skill, you can do so on sites such as and

It’s important that you create a master calendar for this six month time period. This can be done with something as simple as an Excel spreadsheet or Google doc — whatever works best for you! If you have a plan, you will start to make incremental progress.

If you’re going to make a major career transition, respect yourself enough to track your efforts. Monitor how you’re doing, where you left off, who you need to touch base with, and what you need to do next. Set reminders for yourself.

Shift your personal brand

When you’re on the hunt for a new job, it’s important to market yourself. Who’s your target audience? The types of companies you want to be a part of. More specifically, the people within those companies who make the hiring decisions.

Make it easy for your target audience to see who you are and why you’re a good fit for them. Be sure to shift your skills on your resume to fit the type of role that you want to move into.

Keep in mind that if you make drastic changes on your LinkedIn profile, it could look questionable to your current employer. If you’re wanting to keep the job hunt under the radar, be sure to adjust your privacy settings so that your connections aren’t alerted when you make changes to your profile.

Leverage your connections  

There’s no need to do this alone! People who know you and care about you are often very willing to help. Get a list of your most trusted friends and confidants and let them know your goals to transition into a different role.

Make it easy for your connections to support you. Remember to always be specific. Include details such as:

  • The specific types of role you’re looking for
  • The job duties you’d like to be performing
  • The names of companies you’re interested in

Get in cahoots with industry leaders

When you’re looking for a new job, you will probably find people who are in a role that you hope to be in. Don’t be afraid to reach out to them for an informational interview, or to get a few tips from them to help you along your path.

Most people are supportive when you approach them in a genuine. It all starts with a simple ask. Approach someone at first by complementing/validating them. Then simply ask them if they have a couple of moments to answer a few quick questions about the work that they do.

Always remember that there may be setbacks along the way. Don’t let it get you down or stress you out. Nothing is impossible unless you decide it’s impossible. Work hard for the fulfilling career that you deserve!

Have any career questions for Jenny? Reach out to her via Twitter or her website. Thanks to GRAYBOX for hosting our Professional Development event.

We’d love to see you at our next event! Click here to see what’s coming up.

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