“I wish I could see the future of both paths,” Sherry told me. She stood at a professional crossroads. One opportunity involved joining a small, growing business in East Lyme, Connecticut—an enterprise run by her friend’s father, where she would eventually partner with a close friend and do work she genuinely enjoyed. Her other option was to remain in what she called her “safe cubicle” at a stable employer in Hartford.
I understand the emotional appeal of that cubicle. Even people who logically recognize that safety can be illusory often choose stability over uncertainty. From a purely financial standpoint, most individuals will select an $80,000 job with predictability over a role that might yield $160,000 in one year and $60,000 the next—even when the expected economic value clearly favors the higher-variance opportunity. The simple possibility of earning less, even temporarily, is enough to paralyze rational decision-making.
This was the trap Sherry found herself in. She was convinced she would enjoy the new position dramatically more—her words were “ten times more”—but fear of unpredictable earnings kept her rooted in place.
To help her think more clearly, I shared an example from my own life. I have what I call a “professional twin,” someone whose résumé mirrors mine almost exactly. “Ted” and I attended the same law school, grew up in similar parts of New Jersey, graduated from colleges of comparable prestige, and built our early legal careers in near-parallel ways. In 2000, we were both unhappy in our respective law firms.
I decided to take a leap and start an education company—an unconventional choice at the time, given my academic and legal background. It carried significant financial risk, but the potential upside in meaning and autonomy mattered more to me. Ted, by contrast, chose the safer path and remained in traditional legal roles to avoid the risk of financial instability.
Ten years later, the contrast became striking. My education businesses flourished, Ted, despite making a lot of money was both miserable and financially challenged: he spent heavily over the years trying to compensate for persistent unhappiness at work.
His realization was painful. Two decades of staying in a job he disliked, all in the name of economic security, left him neither fulfilled nor financially ahead. He found himself confronting the hard truth that the reason he stayed—the promise of stability—had not materialized.
Sherry’s dilemma is one I see often in career counseling sessions at Career Counseling Connecticut. Many professionals overestimate the security of the “safe job” and underestimate the long-term cost of remaining in work that drains them. My view is that thoughtful, guided career risk—supported by expert advice—often leads to both improved well-being and greater financial resilience. Fear alone is a poor career strategist.
As some of our most successful clients have said: “our work gave me permission to do what I knew I should.”