Ready for ‘When’: Preparing for Unexpected Job Transitions


Unexpected job transitions have become a common narrative. In such a scenario, the question isn’t if you might face a job transition, but when. This post offers an enhanced checklist to prepare you for that potential ‘when’ moment in your career, complete with insights from industry experts.

Career Preparedness

  • Stay updated: In an ever-changing job market, upskilling is crucial. As LinkedIn’s Learning Blog puts it, “the shelf-life of skills is less than five years.” Allocate time each week to learn something new related to your field.
  • Network: As Dorie Clark, a personal branding expert, advises, “Your network is your career insurance.” Connect with people online and offline, within and outside of your industry.
  • Update your CV and LinkedIn profile: Keep your resume updated and optimized for Applicant Tracking Systems (ATS). Many companies use ATS to filter applications before they ever reach a human. According to Jobscan, a platform that optimizes job applications, “70% of resumes will never be seen by human eyes.” To improve the chances of your resume getting noticed, include relevant keywords from the job description, tailor your resume to each job application, and keep the formatting simple and ATS-friendly.

Financial Preparedness

  • Emergency Fund: Aim to save three to six months’ worth of living expenses. This cushion could prove vital if you face sudden unemployment.
  • Diversify Income: Creating additional income streams provides additional security. Bestselling author Chris Guillebeau says, “Hustle isn’t just working on the things you like. It means doing the things you don’t enjoy so you can do the things you love.”

Health and Wellness Preparedness

  • Health Check-ups: Regular health check-ups can prevent complications, especially when stress levels might be high. Set recurring reminders for appointments.
  • Mental Health: Recognize signs of stress and seek professional help if needed. “It’s not the load that breaks you down, it’s the way you carry it,” says psychologist Lou Holtz. Utilize stress management techniques like meditation and exercise.

Insurance Preparedness

Navigating health insurance during a job transition can be one of the most stressful aspects of the entire process. Being prepared involves understanding your options, such as COBRA, and their costs.

But what if there was a better alternative?

Our upcoming product, the When Benefit, is designed to ease this process. It’s a financial wellness solution that pays for health insurance premiums after an involuntary job loss, providing a safety net when you need it most.

If the When Benefit seems like a solution you’d want as part of your benefits package, consider having a conversation with your HR manager or employer about it.


While we can’t control every twist and turn life takes, we can control our readiness. Being prepared can make navigating unexpected job transitions less stressful. And with innovative solutions like the When Benefit, the burden of health insurance during such transitions can be mitigated.

Are you ready for ‘when’?

Scroll to Top