The Stacking Benjamins Show Create Goals that Stick (with Ret. Lt. Cdr. Gary MacDermid)
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Jul 16, 2025 Retired Lieutenant Commander Gary MacDermid, a business coach with a military background, shares his insights on goal-setting with unyielding discipline. He emphasizes the importance of defining SMART goals to avoid burnout from borrowed aspirations. The conversation covers techniques for sustainable habit formation and developing multiple income streams. Additionally, they tackle the often-overlooked topic of long-term care insurance, discussing when it’s necessary and how to evaluate your options. Packed with actionable advice, this chat helps you take charge of your goals and financial future.
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Gary's Navy Start Story
- Gary McDermid joined the Navy because his father woke him up unexpectedly with a plan to solve college funding.
- He chose the Navy on his father's recommendation to see the world, not out of personal ambition.
Working On Others' Goals
- Most people spend much of their time working towards someone else’s goals, not their own.
- This can lead to burnout and dissatisfaction if not addressed.
Nuclear Operator's Goal Struggle
- Gary was highly skilled in operating nuclear reactors in the Navy but struggled setting his own goals after leaving.
- Military discipline didn't translate immediately to personal goal-setting.