Hosted by Dan Pascone, CEO of Tailored Wealth (Learn more: yourtailoredwealth.com), Making Sense of Your Money helps high-income professionals optimize their financial strategies. Each episode features expert insights on investing, tax planning, and wealth building, turning complexity into clarity.Connect with Dan here: linktr.ee/danpascone.com
EP #70: The Hidden Cost of Winning at Work, Losing Life
You've built the career, the comp, the title. But have you ever stopped to ask if any of it is actually what you want?
In this episode of Making Sense of Your Money, I sit down with Trisha Maggio, a 25 year corporate leader turned executive coach and the CEO and Founder of TDM Coaching. Trisha spent over two decades building a reputation as the person who could solve any problem and overachieve on command, until a layoff in 2020 and the sudden loss of her father in 2022 forced her to ask a question she had never taken time to answer.
Who am I without my job and without my title?
We get into what it really means to separate your identity from your role, why Trisha chose to leave corporate without a perfect plan, and how she uses a simple tool called the wheel of life to design a version of success that goes beyond the paycheck. If you have ever felt like you are winning at work while everything else runs on empty, this conversation gives you a practical way to think about balance, not just balance sheets.
For executives weighing their own hybrid retirement timeline, Trisha's story is a reminder that the financial plan and the identity work have to move together.
Want to talk through your own hybrid retirement or equity strategy?
Book a Free Wealth Strategy Call: https://yourtailoredwealth.com/book-a-call (https://yourtailoredwealth.com/book-a-call)
More episodes and resources: https://www.makingsenseofyourmoney.com/ (https://www.makingsenseofyourmoney.com/)
#HybridRetirement #ExecutiveCoaching #WorkOptional #FinancialPlanning #RichLife
Disclaimer
Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.
7 Aug 2026
EP #69: The College Sticker Price Is Almost Never What You Pay
Most parents look at a six-figure college sticker price and either panic or say the words that quietly cost them a decade of retirement: "I'll just figure it out."
My guest this week is Shanna Due, CFP, CCFC, AFC, founder of Due Financial. Shanna spent years as a full financial planner before specializing entirely in one thing: helping families get the college experience they actually want for the least amount of investment. She works the numbers most parents never see, and she has two kids of her own heading through the system right now.
We get into why the published cost of attendance is almost never what you pay, how to decode a school's real business model, and the financing moves most parents miss. Shanna breaks down how to read a school's net price calculator, when to take the federal direct loan even if you do not need it, and how to turn a hundred-thousand-dollar decision into a monthly number a 17-year-old can actually understand.
We also get into where college is heading in the AI era, why some schools will get more valuable rather than less, and the cash flow most parents forget they free up the day their kid leaves home.
Topics Discussed:
The three-legged table for choosing a school
Why the sticker price is rarely the real price
How to decode a school's business model and net price calculator
529s, Roths, taxable brokerage, and cash flow as funding sources
When to take the federal direct loan as a safety net
Turning a six-figure loan into a monthly number kids understand
Where college is heading in the AI era
What You'll Learn:
How to figure out what your family will actually pay for a given school
Which financing levers to pull and in what order
How to set financial expectations with your student years in advance
Why timing income and distributions matters for aid eligibility
Learn more: makingsenseofyourmoney.com (http://makingsenseofyourmoney.com)
#CollegePlanning #FinancialPlanning #529Plan #CollegeTuition #WorkOptional
Disclaimer
Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.
31 Jul 2026
EP #68 The Fear You Cannot Analyze Your Way Out Of
A lot of high performers are sitting on two versions of the same tension. At work, they lead a team that has outgrown how it used to operate, where the real conversations now happen in the hallway instead of the room. Personally, they are circling a bigger leap of their own, waiting for a right time the data never quite delivers.
My guest this week is Rachel Wexler, a leadership development partner who spent 25 years running product and strategy in the corporate world before building her own practice. She helps leadership teams that have outgrown the way they work together reach the next level of performance their business now demands.
We get into how to spot a team that is quietly fracturing, the body language, the silence, the side conversations, and how to build real healthy conflict instead of just claiming you want it. Rachel makes the case that trust and vulnerability start with the leader, and that consensus is not the goal, being heard is.
Then we get personal. Rachel spent eight to ten years thinking about leaving corporate before a milestone birthday finally pushed her to move. We talk about facing the fear you cannot analyze your way out of, and what the transition to running your own practice actually looks like on the other side.
Want to talk through your own hybrid retirement or equity strategy?
Book a Free Wealth Strategy Call:
https://yourtailoredwealth.com/book-a-call (https://yourtailoredwealth.com/book-a-call)
More episodes and resources: https://www.makingsenseofyourmoney.com/ (https://www.makingsenseofyourmoney.com/)
This content is for educational purposes only and does not constitute investment, tax, or legal advice. Consult a qualified professional for guidance specific to your situation.
#Leadership #ExecutiveLeadership #WorkOptional #HealthyConflict #CareerTransition
Disclaimer
Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.
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