Every so often, a “money question” shows up wearing a disguise.
It looks like a sports decision. Or a prideful decision. Or a family decision. And then — quietly — it becomes a tax decision, a contract decision, and a long-term planning decision.
I’m Tim Lux, CFP®, CFPA,® VP of Financial Planning at Kingsview. We help people make big decisions that can change the direction of their financial lives and future retirement — and we make sure those decisions don’t create problems they didn’t see coming.
Here are three situations we’ve been hearing versions of lately — all very different, all very real.
My son is a junior in high school. A talented running back. He’s getting scouted by some of the best schools — with some blue blood programs showing real interest.
He’s torn. We’re torn. And now NIL is in the mix, which feels like a whole new universe.
How much should NIL influence the decision? And what should we be thinking about that nobody thinks about?
— Excited, Overwhelmed, Trying Not to Fumble This
First — congratulations. That’s a great problem to have, and it’s also a high-pressure one. I’ve come across a few situations like this over the past year — NIL is still the wild wild west and literally as I write this, things could change.
That being said, here’s the clean truth: NIL matters, but it’s rarely the most important variable. It’s also the variable most likely to distract you from the decision that will matter 10 years from now.
If you want a framework that keeps everyone sane, I’d look at it in three layers:
If NIL becomes real, I’d encourage one boring move that saves a lot of grief: separate the money from the lifestyle. Open a dedicated account for NIL income, assume taxes, and decide in advance what portion is spendable vs. protected.
My team and I created a great piece on this that I highly recommend. Check it out - it’s free to download.
I’m 60. Net worth roughly $2 million invested. I still make about $300,000 a year. I’ve got kids and my goal is simple: I want to leave them everything I have.
A lot of friends and colleagues think this is a bad idea, but at the end of the day, if I can give them a leg up when it comes to their education and career aspirations — I personally think my kids should start a plumbing business and call it a day — so be it.
Here’s my other truth: I don’t want an advisor. I enjoy investing, I follow markets, and I want to manage it myself.
If I’m doing this without expert guidance, how should I be thinking about investing? What should I consider? And what pitfalls do people like me fall into?
— DIY Investor With a Legacy Goal
I respect the self-awareness here. Most DIY investors don’t ask this question until after they’ve taken a few avoidable hits.
If you’re going to run your own portfolio, I’d approach it like you’re running a small business — with rules, controls, and a plan for what happens when you’re not there.
Here’s what I’d want in place.
This is where the value of an advisor isn’t stock picking. It’s infrastructure:
Sometimes that’s also a trust conversation — not because you “need a trust to be wealthy,” but because you want control, clarity, and continuity.
If you stay DIY, at minimum I’d make sure there’s a written plan your family can follow:
Because your portfolio may run fine for 20 years. But legacy planning is about what happens on the one day you’re not here to explain it.
And, of course, if you ever changed your mind and think an advisor is necessary, take our five-minute quiz and get matched with an advisor in your area.
You’ll get all the resources you need to set you and your family up for success. Plus, you’ll be able to work with financial planning professionals like me.
“What’s a backdoor Roth? I only have a 401(k) with $800K. I’m 40, divorced, paying alimony, make $200K.”
I keep hearing people talk about a “backdoor Roth.” I’m not the sharpest tool in the shed, so please don’t mock… but don’t fully understand what it is.
I’m 40. Divorced. Paying alimony. I have one kid. I make about $200,000 a year. My retirement savings is mostly one 401(k) — around $800,000.
Am I supposed to be doing a backdoor Roth? How does it work? And does divorce/alimony change anything?
— Trying to Do the Right Thing Without Getting Cute
Trust me: very few people understand backdoors. You might not be rich with financial acumen, but at least you’re asking — and willing to ask — the right questions. Most people aren’t.
A backdoor Roth is one of those strategies that sounds sneaky, but it’s really just a workaround for income limits.
Here’s the simple version:
Now, you said something important: you only have a 401(k). That often makes this cleaner, because a 401(k) is not the same as a Traditional IRA for that pro-rata calculation. However, you still want to confirm whether you have any other IRAs floating around (old rollovers, SEP, SIMPLE, etc.).
As for divorce and alimony: it doesn’t prevent a backdoor Roth, but it does affect your broader planning priorities:
Here’s how I’d frame it:
If you’re consistently able to save and you don’t have outside IRAs complicating it, a backdoor Roth can be a very solid move at 40 — especially because tax diversification becomes more valuable later.
But don’t do it just because it’s trendy. Do it because it fits inside a plan:
The best strategies are boring, but the key is doing the boring things in the right order.
Questions may have been altered or edited from the actual submission for brevity, clarity, or anonymity Questions may not have been submitted by actual clients and may have been added by Kingsview for discussion purposes.