Do You Love Winning or Hate Losing More?

When it comes to career transition, your inner compass isn’t just your résumé or LinkedIn profile; it’s your mindset. And one powerful question to ask yourself is: Do I love winning more, or do I hate losing more?

Psychologists call this approach vs. avoidance motivation. Some people are driven by the thrill of the chase and the thrill of winning. Others are motivated by the fear of stumbling or losing. Neither is “better,” but each creates a very different career path.

• The Win-Lovers

  • Thrive on achievement: new titles, new responsibilities, and visible progress.

  • Will often take bold steps—switching industries, launching a business, or pitching themselves for a stretch role.

  • Risk: chasing the high of a “yes” can sometimes lead to overcommitting or leaping before looking.

• The Loss-Haters

  • Excel at preparation: meticulous research, thorough applications, and thoughtful planning.

  • Tend to be steady, dependable, and risk-aware.

  • Risk: staying in an unfulfilling role too long out of fear of failure or regret.

So what does this mean for your transition?

• If you’re a win-lover: build in checkpoints. Don’t just sprint to the next shiny thing. Take a moment to confirm that it aligns with your long-term vision.

• If you’re a loss-hater: set deadlines. Permit yourself to act before perfect conditions arrive (spoiler: they never do).

The most successful transitions happen when you blend both mindsets: the energy of chasing wins with the grounding wisdom of minimizing losses. Whether you’re wired for thrill or caution, the true loss is

The job search is the ideal time to engage the support of a certified coach with experience in helping professionals achieve better, faster results. At KICKSTART Your Transition, we offer a broad range of services to fit your needs.