I'm a financial advisor for purpose-driven families.
Father of 8. Former pro baseball player. Formerly 100K+ in debt.
I've spent nearly 10 years sitting across from high performers who are running hard at their calling, but financial anxiety remains firmly planted in the passenger seat of their life.
Here's what I've learned about money that you don't read about in a personal finance textbook:
1. Your money mindset was caught, not taught. You're running software your parents installed, and most people never realize they need an update.
2. Rich and anxious is not winning. Emotionally detaching from money is true financial freedom.
3. The number you're chasing won't quiet the anxiety. The vision for what the number is for will. Your why is a who.
4. Twelve-hour days aren't provision. They're an escape route with a good excuse attached.
5. Your biggest opportunity isn't to cut the latte. It's to switch buses. You may need to change/supplement your income vehicle entirely.
6. The most dangerous financial advice isn't bad advice. It's good advice given to the wrong person at the wrong life stage.
7. Give first. Invest second. Live third. The order matters more than the amount.
8. Generational wealth isn't built by the person who earns the most. It's built by the first person in a family tree who decides to break unhealthy generational chains about money.
9. There's a difference between success and significance. Big profits make a successful business. Wealth is a chance to change someone's life.
10. People are happiest when they are growing and giving. We should financially plan accordingly.
If any of this resonates, follow along. I post regularly about faith, family, fitness, and finance.
And if you're a purpose-driven family who wants to build wealth that actually means something, my DMs are open.
Every family I work with eventually asks some version of the same question: is this enough?
Is this enough money? Have I saved enough? How am I compared to other people my age? What if there is a downturn, is there still enough?
My challenge is to ask a different question. Instead of, "is this enough," consider asking "how much money is required to impact the lives I feel called to impact?"
Boring is not the same as safe, and exciting is not the same as unsafe.
The market doesn't care about feelings. Discipline should happen outside of how you feel about things.
The disciplined investor beats the emotional investor over time.
High performers:
If you're struggling with burnout, and money stress keeps fueling that burnout-flame, working harder is a bandaid, not a remedy.
Clarity breeds confidence. Sit down with your numbers, understand your current state, where you're going, and what it takes to get there.
Then run the play. Worrying will only stress you out, not help you live out your mission.
If you've got money left over in a 529 because your kid got scholarships, went a cheaper route, or didn't need it all, you're not stuck choosing between a penalty and an unused account anymore.
Under current rules, you can roll a limited amount from a 529 into a Roth IRA for the same beneficiary over their lifetime, as long as the account has been open at least 15 years. There are annual limits and some fine print, but the money doesn't have to sit there doing nothing or get penalized on the way out.
If you're sitting on 529 leftovers wondering what happens to them, ask your advisor about the Roth rollover provision before assuming the only options are "use it" or "pay a penalty" or "give it away."
Ever heard the term "tax loss harvesting?" It's popular toward the end of the year, and just means that you sell, on purpose, any investments that are negative (at a loss) for the year to offset any gains you have.
Or, the losses can offset up to $3,000 against ordinary income if you don't have gains to offset.
The catch is the wash sale rule. Buy or sell the same, or a substantially identical, investment within 30 days before OR after the date of sale, and the loss gets disallowed.
If you're sitting on a position that's down and want the tax benefit without losing your market exposure, swapping into a similar but not identical investment for 30 days could be a solution.
You keep the exposure and still get to use the loss. Education, not advice.
A hitting coach once told me, "Stop trying to do everything. You can only work on one part of your swing at a time."
So simple, but so difficult to execute on. I was forever thinking about my hand placement, how relaxed I was, where my head was when I was loading my hands, was I transferring weight well, and on and on...
Our brains can't execute at the highest level on all things at once.
That's where a lot of smart people are right now with their money. Endless information, a podcast for every theory, a zillion tax and investment approaches, AI bubbles and AI revolutions at the same time, so much to execute on.
We don't need more information. With AI, information is commoditized.
We need the right next move, and it's helpful to have someone name that for you, because I know as a hitter I couldn't see it for myself.
If you're the type of person who gives to multiple charities and would value a single, clean tax deduction instead of tracking receipts from a bunch of places, a donor advised fund does that.
You contribute now, cash or appreciated stock, take the deduction this year, then decide which charities you give to, how much you give them, and when they get the money, even years later.
As a bonus, the money grows tax free while it sits in the fund waiting to be granted out.
If your giving feels scattered and you want it to streamline and simplify your giving life while taking advantage of some tax free growth, opening a donor advised fund before year end is the solution.
Long-term investing is like watching a horror movie.
Just when you think the danger has passed, another scare is lurking around the corner.
Market corrections, crashes, and crises are inevitable. You never know when the next one will strike.
But history tells us that those who stay in their seats through the scary parts are rewarded in the end.
Happy Halloween! Dressing up in costume is so fun for a night, but don't be that guy who plays dress up with his finances.
In other words, don't buy the brand new Escalade if you're on a 10 year old Tahoe budget. Buy the Tahoe, keep your financial house in order, and enjoy the journey!
Remember, comparison is the thief of joy.
@RetireEarly70 I never understand why plans make it so difficult to figure out that they offer after tax contributions 🤯. That should be front and center!
If you've maxed out your 401(k) (maybe it's a Roth 401k?) and your income is too high for a regular Roth, sometimes there's another option if you have more money to invest in company's retirement plan.
Some employer plans allow after-tax contributions beyond the regular 401(k) limit, then let you convert those dollars to Roth inside the plan. It's called a "Mega Backdoor Roth."
Not every plan allows it. Check your plan document or ask your HR team whether the after-tax and in-plan conversion features exist before assuming it doesn't apply to you.
The day the Royals released me I remember thinking, "How can I be so focused on one thing for 20 years only for it to end one day with a single conversation?"
I had zero plan for who I was without a uniform on. I was newly married, now jobless, now homeless, and now clueless.
Eventually I learned a lot about identity, that it represents who you are not what you do, and I did the deep introspective work to understand more of my big-picture calling.
And over the years I've learned to use money toward those callings on my life - and when you operate day-to-day in your true identity and use money to fund it, there's a real freedom and weight that is lifted...because you don't worry about the fear of "did I screw up, should I have bought that/taken that loan/did that deal/invested in that employee/taken that trip/etc"
Your money becomes a tool that you "use," not "spend" or "waste," to further the big-picture mission of your life.
Discipline beats motivation. True. I live by that mantra.
But with money and investing, I've learned that systems beat discipline.
Automate the transfer the day the paycheck hits, before you see the number in your checking account.
If you're struggling to save and invest consistently, automating the decision is the solution.
Ever heard of "soft saving?" I just heard the term, but apparently it's making waves.
It means giving up on the big, far off goal - the paid off house, the comfortable retirement, etc - because it feels too distant, and spending on your life now instead.
I get it - in a society with the average attention span shorter than that of a goldfish, why focus on anything long term?
Why can't we have both? I understand what it's like to not be able to afford a cup of coffee - I was there as a dad of 5, not as a new college grad. Nothing matters more than keeping the lights on and the family warm and fed.
But assuming you're not there, what about creating a framework where you both spend AND invest? We don't need to over complicate it.
1) Know how much you need per month to live
2) Invest a certain amount of your paycheck above that number (on autopilot, just like your mortgage payment)
3) Use the rest to enjoy today
I believe I’m an encourager. My family and I feel called to be lights on a hill and a glimpse of what’s possible when living a life of purpose. I also feel like joy and generosity and hospitality are parts of me wherever I go. I’m not clear on a single specific calling but know these are parts of my identity.
Here's what I believe about your finances in order to live a fulfilled life:
Money isn't the end goal. Fueling your calling is.
You don't need your entire life mapped out, but you need to know why you're on this earth. Then the money funds that purpose.