Mike MilliganFounder and CEO, 1.oak Financial · Founder and CEO, 1.oak Financial

Life After the 9-to-5: Conquering Unstructured Time

26 Feb 2026 · 1 min

Watch on YouTube

0:48

In this segment of his YouTube video, Mike Milligan highlights boredom as a largely ignored risk for retirees. He explains that boredom often disguises itself as restlessness, irritability, or repetitive low‑effort activities such as doing the same Sudoku puzzle daily or endlessly playing solitaire. These behaviors can lead to unnecessary spending—especially for those who are natural spenders—such as daily lunches or repeated purchases, which can quickly derail a carefully crafted retirement financial plan. Milligan stresses that the antidote is a clear vision and purpose for one’s retirement, providing direction that mitigates boredom and protects financial stability.

Chapters

Is boredom a real retirement risk nobody plans for? Boredom doesn't always look like boredom. It can look like restlessness, irritability, or unnecessary spending. It could be something as simple as doing the same Sudoku every day or playing solitaire on your phone all the time, and time just gets wasted, right? Boredom, but boredom will also influence financial decisions. It will, uh, if you, if you're bored and you have nothing to do and you're a natural spender, you'll end up going out to lunch every day or maybe going to buy unnecessary things for the 3rd or 4th time. And it can quickly derail a financial plan unless you provide a vision and a purpose for what your retirement is.