Help Me Retire Podcast - Episode 24
- Mike Brown
- 7 days ago
- 7 min read

Three questions
Show notes:
If I could sit across from you right now... and ask just one question to cut through all the noise about money... markets... and retirement... it would be this:
“What would you be doing right now... if you knew you’d never have to work for money again?”
That’s the first of three simple questions we’ll be pondering together... in this episode of the Help Me Retire Podcast...
This is the Help Me Retire Podcast… with your host… Mike Brown… Senior Wealth Advisor with Raymond James Financial Services… and head of Brown Family Wealth Advisors…
Mike is the best-selling author of Your Way to True Wealth: How to Make It Happen, Make It Last, and Make It Matter…
He and his team have been helping clients pursue their dreams of financial independence for the past 30 years… and in the Help Me Retire Podcast… he’ll share his best ideas with you…
And now… here’s Mike…
What would you be doing right now... right this minute... if you knew you’d never have to work for money again?
That’s a loaded question, right? It makes you think about reaching a point in life where your income... the money you need to live the way you want... is coming from somewhere other than a job...
Some people call that retirement... others might think of it as financial freedom or independence...
I call it True Wealth... the point in life where you get to do exactly what you want to do... free from the burdens of having to go to work every day...
If you’re a client of ours... you might already be at that point...
If you’re not... but you want to be one day... and you feel like you’re making progress toward True Wealth... it’s time to ask yourself a few questions so you’ll be ready when the time comes... for example...
What will my chosen lifestyle cost? You need a realistic picture of what you’ll be spending each year once you stop working... not a guess... not some rule of thumb... but a clear number that reflects how you want to live...
Next question: How will I replace my income? Without a paycheck... where will the money come from... Social Security... pension checks... income from your investments? Will that income be enough? And will it increase over time... to keep you ahead of inflation?
And here’s one that has nothing to do with money: What am I doing to do when I’ve got all this time on my hands? Working gives you structure... and you need structure. That means you’ll have to replace that structure when you stop working. You’ll need a new purpose... maybe even a new identity. Might need to do some thinking on this one... it’s more important than you realize...
Again... maybe you’re already at the point where you can stop working for money... but that doesn't mean you don’t worry about it... or think about it all the time...
Let’s take the second step toward True Wealth... next...
I’m asking you three questions today...
The first was... “What would you be doing right now... if you knew you’d never have to work for money again?”
Now, here’s the second question: “What would you be doing right now... if you knew you didn’t have to worry about money again?”
You can be as rich as Midas... and still have trouble sleeping at night... until you get a plan in place to address these nagging questions that all retirees face at some point...
Am I spending too much? Too fast? Am I going to run out of money?
What is inflation going to do to my savings? How is my income going to keep up with the rising cost of living?
What’s going to happen to my investments the next time the market drops? Is there some way I can protect my portfolio from market volatility... and still earn a decent return over time?
What about taxes? They’re never going to go away... but what should I be doing so I don’t have to pay more in taxes than I’m required to?
Do I still need life insurance to protect my family now that I’m retired? Do I have enough? Too much?
How else should I be protecting myself? How am I going to afford health care now that I’m off the company plan?
Should I be worried that somebody’s going to steal my personal information... and then maybe steal my money?
How about debt? Should I pay off my mortgage before I retire? How about other debts... car payments... credit cards? And if debt has me worried... what should I be doing about it?
Should I help my kids or grandkids pay for college? And if I do... what’s that going to do to my retirement plans?
That’s a lot of questions... a lot of things you might be worrying about right now... especially as you approach retirement...
Not going to have all the answers today... but answers won’t do you much good if you don’t know the right questions... and that’s what today’s episode is all about... getting the questions right...
I’ve got one more question for you... and it’s about getting past working for money... and worrying about money...
It’s the highest level of True Wealth... and we’re going to talk about it in just a second...
Okay... I said I’ve got three big questions for you today... and we’ve tackled the first two...
“What would you be doing right now... if you knew you’d never have to work for money again?”
And... ““What would you be doing right now... if you knew you’d never have to worry about money again?”
Now, it’s time for the third question... and it’s a fun one... here it is:
“What would you be doing right now... if you knew you’d never have to think about money again?”
What would that feel like... once you’ve got the working and the worrying out of the way?
Here’s what that would feel like...
You’ve got all your finances... all your records in perfect order... either in a filing system you’ve designed... or stored in a secure online system...
You wouldn’t think about how to pay your bills anymore... you’ve got everything set up to be paid out of your bank account automatically each month... while you’re out having fun somewhere...
And you don’t have to think about whether there’s enough money to pay those bills... because there is... and there always will be...
You’ve got money flowing into that bank account every month... from Social Security... pensions... your investments...
You’ve structured your portfolio in such a way that they produce income that increases over time... faster than your cost of living...
All that income gets deposited automatically... without you having to think about it...
When you reach the age when the IRS says you need to take money out of your IRA every year... those calculations are done for you... and there’s a plan in place to make sure those required minimum distributions get done on time...
You don’t have to think about it...
You’re living in a place you love... and if and when you ever get to the point where you can’t live there anymore... there’s a plan in place for the next step...
You were smart enough to get your family involved early on...
They understand what’s important to you... what you value... and they want to help you...
If and when the time comes... a time when you need help making financial decisions... you’ve got people you love in place to act on your behalf...
They’ll know how to access your recordkeeping system once you give them permission to... they’ll know where everything is when they need it...
You’ve got beneficiaries in place on all of your financial accounts... updated on a regular schedule...
Maybe you have a trust in place... to make sure all of your assets go where you want them to go at the end of your life... outside of probate...
And you’ve got advisors you can trust... people you can count on to give you the answers and advice you need... the right answers... when it comes to your taxes... your investments... your estate plan...
Those advisors are all pulling in the same direction... toward the same end goals... to carry out your wishes...
You know those things are possible... you believe there are workable answers to all these questions... even if you don’t know where to start...
And you probably want those answers... that’s why you’re listening to me right now...
We didn’t talk about the answers to all these questions today... but there are answers...
Here’s what I’d do if I were you...
If you’re still working for money... regardless of your age... sit down with someone and make a plan...
A plan that will get you to the point where you only work because you choose to work... and not because you have to...
A plan that will allow you to replace your employment income with other sources...
Once you’ve got that plan in place... one that’s going to take you where you want to go if you’re not already there... then start working on the things that worry you financially...
Getting out of debt...
Paying less in taxes...
Protecting yourself... your wealth... your health... your privacy...
Generating investment income that increases over time faster than inflation... income that you can be reinvested to help you build wealth faster...
A rising stream of income you can live off when you stop working...
And finally... when you’re on track to stop working for money one day... and not worrying about money anymore...
Start getting your financial house in order... so that you don’t even have to think about money anymore...
So you can go out and see the world... and live the rest of your life... on your own terms...
We’ve developed a 7-step process... called the Brown Family Wealth Management system... that we use with our clients...
To guide them... step-by-step... through all the questions we talked about today... and more...
One question... one answer... at a time...
You can learn about it... right here on this website... HelpMeRetirePod.com... a podcast series on the process... blog posts you can read at your leisure...
I hope you’ll take advantage of it... and if you’d ever like me to walk you through it face-to-face... you know where to find me...
In the meantime... my family and I wish you the very best...
See you next time...
Securities offered through Raymond James Financial Services, Inc., member FINRA/SIPC.
Investment advisory services are offered through Raymond James Financial Services Advisors, Inc. Brown Family Wealth Advisors is not a registered broker/dealer and is independent of Raymond James Financial Services.
Any opinions are those of Mike Brown and Brown Family Wealth Advisors and not necessarily those of Raymond James. This material is being provided for informational purposes only and is not a recommendation. There is no guarantee that these statements or opinions will prove to be correct. Investing involves risk, and you may incur a profit or a loss regardless of the strategy selected. Past performance is not indicative of future results. Prior to making an investment decision, please consult with your financial advisor about your individual situation.
Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional.