10 Tough Conversations You Need to Have Before You Retire. Thank you to Cameron Huddleston for including me in her article for GoBankingRates.com. You’re retired, now what? For many, spending up to 10 plus hours a day working was not uncommon. What will you do to fill every day in retirement for the next 25-35 years? Knowing the answer is key to your wellbeing in retirement.