The Stacking Benjamins Show · Apr 10, 2026 · 1:01:42
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Most people don't start thinking seriously about retirement until their forties. If that's you, the good news is you're not behind. You're normal. And this week three CFPs, Jackie Cummings Koski, Roger Whitney, and OG break down exactly what to do, in what order, starting right now.
In this episode:
Why panic is the enemy of a good retirement plan, the first place your money should go before anything else, why your savings rate matters more than finding the perfect investment, and the one investing mistake people make when they feel behind.
Biggest takeaways:
Give yourself grace first. This stuff isn't taught in school. The two years Jackie spent just processing her situation before taking action weren't wasted. That clarity is what made everything else stick.
Increase your savings rate by 1% every six months. Going from 3% to 13% over five years feels like a non-event the entire time. Automation makes it invisible.
Simple beats clever. Index funds, low cost, diversified, and boring. When you feel behind, the temptation is to swing for the fences. That's exactly when boring saves you.
Real estate and dividend strategies are tactics. Tactics come after you have a strategy. For a 40-year-old starting from zero, the strategy is build the habit and save more.
Resources mentioned:
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Episodes: The Stacking Benjamins Show