Hi, I’m Devin Choules, founder and CEO of Choules Financial, and on this week’s Key to Yes, we’re going to walk through the five types of people who need our help—and today, we’re focusing on one of the most common: the Uncertain Planner.
This is the person who’s done all the right things. They’ve saved diligently, have several IRAs, 401(k)s, a brokerage account, and cash on hand—but they’re not quite sure how it all comes together. They’re wondering, “Do I have enough? What’s the plan? How do I make this work?”
That’s where we come in.
Let me introduce you to Diane, a former HR executive who came to us seeking clarity around retirement income, tax efficiency, and peace of mind. She had done a great job saving, but she didn’t know how to stack all the pieces together into a cohesive plan. She had multiple retirement accounts, a healthy brokerage account, and a sizable rainy-day fund—but was overwhelmed by questions like:
How much can I safely withdraw each year?
Which accounts should I take from first?
Will this push me into a higher tax bracket?
Will it make my Social Security taxable?
Her concerns were real—and common.
She feared running out of money. She feared paying too much in taxes. And she was overwhelmed by how many accounts and advisors were involved—none of whom were working together.
Unfortunately, that’s what we see all the time: people think they’re diversified because they have money spread across several firms or advisors. But what they really have is confusion and duplication—not coordination.
That’s where our process makes the difference.
Through the Key to Yes Process, we consolidated her accounts, created a unified investment strategy, and eliminated duplication. We brought her IRAs together, analyzed her holdings, and found overlap—like owning the same stocks in multiple accounts without even realizing it.
Then we created a customized income plan so Diane could clearly see:
We implemented a Roth conversion strategy for her final working years, helping her reduce long-term tax exposure. We modeled different retirement dates and spending scenarios so she could retire confidently—knowing her plan was built, written, and ready.
At Choules Financial, we focus on all five core areas of retirement:
Investments
Income
Taxes
Healthcare
Estate & Legacy
These don’t work in silos. Your investments should support your income. If your money isn’t going to be spent, it’s for legacy—but either way, we need to understand the tax impact of how it’s distributed.
And don’t forget healthcare. It gets expensive to age. When a large medical expense comes up, and we have to withdraw from pre-tax accounts like 401(k)s or IRAs, it can push you into a higher tax bracket and create unintended consequences.
That’s why we build full-spectrum plans and organize them into what we call the Yes Binder—a physical and digital resource that lays out everything:
For Diane, this gave her confidence and clarity. She walked away with a plan—not just a hope. She knew how her income would be replaced, how to minimize her tax burden, and how to protect her Social Security from unnecessary taxation.
Most of all, she was able to finally remove the weight of the what-ifs and say yes to retirement.
Now here’s what that looks like when you come to meet with us.
Your first appointment is like a first date. We’re simply exploring whether we’re a good fit. During our Yes Discovery Meeting, we’ll walk through what you currently have in place:
Income
Investments
Taxes
Healthcare
Legacy
We’ll address what’s being overlooked—either by your current advisor or, if you’re doing it on your own, by default.
If it makes sense to move forward, we put on our hard hats and get to work. We’ll run a risk analysis, fee analysis, and income analysis. We’ll show you exactly how our process could help you retire with more confidence and less stress.
That’s when we formally engage—and from there, it’s just the beginning. This isn’t a one-and-done process. Life changes, and your plan should evolve with it. That’s why we continue to meet regularly to update, optimize, and adapt your plan as needed.
So if you’re like Diane—the Uncertain Planner—you’ve saved well, but you’re not sure how it all fits together… we can help. That’s what we do best.
Down below, there’s a link to schedule your own discovery meeting. We’d love to learn more about your story and help you build a plan that brings you peace of mind.
Thanks for watching this week’s Key to Yes. Be sure to like, subscribe, and click the bell for updates—and we’ll see you next time.
