He Has Two Years of Money and Cannot Take a Vacation | Freedom Friday episode artwork

EPISODE · Sep 11, 2026 · 14 MIN

He Has Two Years of Money and Cannot Take a Vacation | Freedom Friday

from Why Did We Start This?

A young real estate agency owner posted that he has gone almost three years without a day off. He just closed the biggest deal of his career, and the win put him in bed unable to get up, too guilty and too paranoid to take a vacation even though he has enough money to last two years. The question I keep coming back to, and a mentor asked me this years ago, is what is enough. If you already had the revenue you picture in your head, would you still get up and work nine to five? Jonathan and I took a month in Oklahoma this summer and worked two days a week, and the first days off were the hardest, because the worry comes with you. So my advice to him is the one nobody gives. Stay in bed today. Then use part of the day to design the week you actually wanted when you started.Book a Free Call with PennyConnect with us:FacebookInstagramLinkedIn1610 Financial SolutionsTakeaways:Decide what enough actually looks like as a number, because a business with no finish line will keep taking your weekends no matter what it earns.Ask whether you would still work nine to five if you already had the income you picture, and pay attention to what your answer says.A big win does not end burnout, and sometimes closing one is the thing that finally exposes it.Rest does not arrive when the calendar clears. It comes from deciding ahead of time which days are not work days, and then defending them.The first days off are the hardest, because the worry travels with you, and that is a reason to keep going rather than to cancel the rest.This show is for general information and encouragement. It is not tax, financial or legal advice. Please consult a professional about your particular situation before you make any decisions.

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He Has Two Years of Money and Cannot Take a Vacation | Freedom Friday

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