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Retire Now, Work Later?

We are in the business of talking, and nearly all of that talking is with you: we’re in the pursuit of connecting your money to your life. Often, we talk about saving for and spending in retirement. You’ve heard us talk about the strategies available with Roth IRAs, in particular, a few times before. 

We still believe there are advantages available here for many investors (never being taxed on gains, of any size? yes, please). But we want to add to the mix another idea. We’re recognizing a trend that merits consideration. 

Life for some can seem quite linear: each milestone follows in turn. You’re born, you go to school, you work, retire, and that’s that. A straightforward path, right? Now, we’re seeing more journeys that look like they swoop around, like life is written in cursive. 

Some of these deviations have been becoming more common, like a “gap year” to gain more experience out in the world after high school but before college. This is a swoop we can choose and plan for.  

Other deviations are more like being thrown for a loop. On short notice, some of us find ourselves stepping away from work to care for a parent—or other family member—due to a growing health concern. Others may discover what we want later in life and find ourselves taking on seasonal work, with long stretches for travel or other passions. 

The traditional retirement savings vehicles were engineered for more traditional retirements. They are likely to assess a 10% penalty for withdrawals before you turn 59½-years-old. While you can take contributions out of a Roth IRA penalty-free, doing so also takes away the chance to grow more tax-free income for the future (the opportunity for growth, not a guarantee of such). 

If there’s a chance that Future You would like to retire in stages or in a unique order, this swoopy life may be something to start talking about now. We have friends who are preparing to travel the world while they still can; we have friends planning to be available to a loved one when they need it. 

What’s on the horizon for you? 

It could be that a balanced taxable account may be a useful complement to traditional retirement holdings. You would pay tax on capital gains, but if you won’t be earning income—or will earn considerably less for a spell—your tax rate may be lower anyway. 

Want to talk through what this could mean for you and yours? Let’s talk, anytime. 


A Roth IRA offers tax deferral on any earnings in the account. Qualified withdrawals of earnings from the account are tax-free. Withdrawals of earnings prior to age 59 ½ or prior to the account being opened for 5 years, whichever is later, may result in a 10% IRS penalty tax. Limitations and restrictions may apply. 


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Posted in Tactics and tagged billy garver, career goals, education, health challenges, ira contribution, IRA rules, life choices, life expectancy, oracle of louisville, retirement account, retirement planning on September 7, 2022 by Caitie Leibman.

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