Sean feels behind because his career hasn't followed a linear upward trajectory like Jason's. He has made several career shifts—from journalism to police dispatching, teaching, and now paralegal work—but hasn't achieved the financial success he desires, currently earning about $54,000 annually, which is half of his $100,000 goal.
Sean started as a journalist at a local newspaper but left due to low pay, earning only $12 an hour after several years. He transitioned to a police dispatcher role, which offered a higher salary of $40,000 annually, but he quickly realized it wasn't a long-term fit due to its monotonous nature.
Sean became a teacher after passing required tests in Massachusetts, but he struggled to find a job initially. When he did, his salary dropped to $30,000 annually, a step back financially. Despite finding success and even being nominated for a national teaching award, he eventually left teaching due to cultural changes at his school.
Sean's lack of a safety net—his father passed away when he was 20, and his mother wasn't in his life—forced him to prioritize immediate financial stability over long-term career planning. This led him to take jobs out of necessity rather than passion or strategic growth.
They advised Sean to leverage his accumulated skills—such as writing, teaching, and paralegal work—to identify problems he can solve, like teaching lawyers to write in plain English. They also suggested exploring freelance opportunities on platforms like Fiverr and Upwork to create additional income streams.
Sean aims to earn $100,000 annually, but he currently makes $54,000 as a paralegal. He acknowledges that his past career moves weren't optimized for money but now wants to focus on achieving his financial goal.
Jason's career path diverged from Sean's due to his willingness to take risks, supported by a safety net provided by his family. After starting in journalism, Jason pursued opportunities that allowed him to grow financially and professionally, including freelancing on the side of his full-time jobs.
Fear of not having a plan or feeling lost drove Sean to take jobs that presented themselves rather than carefully researching and planning his career moves. This led to a series of transitions that didn't align with his long-term financial goals.
Nicole emphasized that the average millionaire has seven income streams, highlighting that relying solely on a paycheck is rarely enough to build wealth. She encouraged Sean to explore freelance work and other income-generating opportunities to supplement his earnings.
This week, Nicole's favorite episodes of Help Wanted (the podcast she cohosts with Entrepreneur Magazine editor in chief Jason Feifer), take over the Money Rehab feed. This episode turns into a Sliding Doors special; today's helpline caller worked with Jason at a local newspaper over two decades ago. Since then, his career hasn't had the linear upward trajectory he hoped for— which has left him making about half the salary he wants. Today, Jason and Nicole break down how to play catch-up.
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