Decades of experience working in financial planning will provide you with a countless number of stories and scenarios.

We thought we’d look back through Joel’s career and ask him about some of the highlights along the way. Check out the different categories we cover on the show and make sure to listen to the full episode for all the details.

Messiest Situation

One particular story that comes to mind is a couple that came in for some help with retirement planning. A review of their portfolio showed they owned a house in Connecticut and Vermont but had just $40,000 saved. This was a situation where our team had to be straightforward with them about the need for selling one of their homes. That was the only way to generate enough income in retirement, which wasn’t what they wanted to hear. But it was necessary to properly plan.

Another common messy situation is when we meet with people that have dozens of accounts and assets spread out all over the place. It can be a lot of work just tracking down all of the statements and balances and then attempting to consolidate them into a more manageable amount. Not only does this makes things difficult for planning, but it can also get even messier for their family should something happen to them.

Biggest Mistake

What was the biggest mistake Joel made early in his career and had to learn from? Well, it’s a mistake that many people make: buying an expensive car. He bought a used Corvette and financed it for seven years! He’ll tell you he didn’t have any business buying that car and eventually got out of it after a couple of years.

Luckiest Thing You’ve Seen

When we think about luck, the first thing that comes to mind is seeing people that get out of the market before it crashes. Even though you might feel like the market is in a delicate position, there’s no way to actually know when to pull your money out. Oftentimes, these people that have gotten lucky attribute it to knowledge instead and that can make them overlook much of the risk they’ll take on in the future.

The other lucky thing we’ll see is someone picking a stock that explodes. Tesla is a great example of this over the past few years. Another example that Joel shares on the show is his dad bought $10,000 of Apple stock early on and ended up selling half when it reached $20,000. That purchase is now with more than a half-million dollars.

The Maddest You’ve Been

The last thing we asked about is getting mad on the job. Joel will tell you that our team doesn’t usually get too upset at work but the main time frustration that arises is when an investment doesn’t play out as you expected. After doing all the research and checking off all the boxes, sometimes things just don’t turn out like you plan. That’s always why you diversify within your portfolio.

MAILBAG

After hearing Joel’s stories, it’s time to move to answer your questions. First up is a truck driver who is deciding whether to stay on as an employee or move to independent contractor status. As an employee, you have certain protections under labor laws, benefits, retirement options, and other positives. On the flip side, moving to an independent contractor means you’ll have to replace all of this out of your own income. You’ll essentially become your own business and you have to manage expenses versus income. There’s definitely a lot to consider.

The next question comes in from a couple that keeps their finances separate. Joel personally feels better when couples share their finances and communicate that information. It’s very difficult to do any effective planning when you don’t have both parties on the same page, but this can also hurt your spouse because they might not know about any issues or mistakes being made financially. Your decisions impact each other.

The last thing we’ll cover on the show is taxes. Thinking ahead to taxes in retirement is crucial so it’s great that this listener is doing just that. Most people are paying more than they have to so proper planning can correct that. But there are many different factors that will help you with what’s best for tax planning and you’ll want to work with a professional to make sure you’re keeping as much money as possible.

[0:45] – What’s in store for the stock market this year?

[2:27] – Tell a story about the messiest financial situation you’ve helped navigate 

[5:50] – Biggest mistake Joel made early in his career

[7:24] – Luckiest thing you’ve seen happen to someone financially

[10:21] – The maddest Joel’s been in his job

[15:21] – Mailbag question on W-2 vs Independent Contractor

[18:54] – Mailbag question on couples with separate bank accounts 

[21:01] – Mailbag question about taxes on retirement accounts

Thanks for listening to this episode. We’ll be back again next week for another show.