Designing a Rich Life Beyond Money and Title | Chris Giomblanco with Dan Pascone | Ep #62

Written by Dan PasconeJune 5, 2026

TL;DR

Chris Giomblanco built a CFO resume most executives spend careers chasing, then spent five years quietly falling apart while hitting every number. His case: performing at the top and thriving there are two different things, and the gap is an architecture problem, not a mindset problem.

You can scale a company 45% compounded for a decade, pass every audit, and make every shot, while your health, relationships, and sense of purpose fall apart underneath it.

Most high performers can't answer the simple question, "what do you want?" Chris uses an eight-dimension diagnostic to force that answer into focus.

The someday mindset, the plan to design the life you actually want once you hit the next milestone, is the most common thing standing between a high earner and the life they say they want.

Performing at the Top vs. Thriving There

Chris Giomblanco has the kind of finance career most executives spend decades building toward: CFO at Dell Alienware, founding CFO of Triad Retail Media, which he grew 45% compounded for a decade, and CFO of Playwire, which he helped grow from roughly $20 million to $150 million in revenue. He passed every audit. He hit every number.

For a sustained five-year stretch at Triad, everything outside the career was quietly falling apart at the same time. "I was performing. I did a great job passing audits and investing and scaling the business," he told Dan. "But my personal life, I was going through divorce, my health was falling apart. Every other element of my life was not doing well for a good five-year period of time." His distinction: you can make every shot and still leave the arena broke and battered. That's performing. Thriving is something else entirely, and it's the gap his advisory work now exists to close.

The Eight-Dimension Framework

Chris didn't arrive at this framework by accident. A mentor mapped out his entire career path on a piece of graph paper thirty years ago, and warned him at the same time: whatever you wish for has a price attached. Chris heard the warning and pursued the title and the money anyway, without looking at any of the other dimensions of his life: health, relationships, spirituality, legacy, connection to something bigger.

The framework he built from that experience is a 40-question diagnostic across eight life dimensions, used to identify where a client's life is out of alignment and to build what he calls a North Star, a concrete picture of what a fully architected life actually looks like for that specific person. It's the starting point for every engagement, because most of the high performers he works with, in his experience, cannot clearly answer the question "what do you want?"

From Someday to Now

The someday mindset, the plan to eventually design the life you actually want once you hit the next title, the next liquidity event, the next milestone, is one of the most common patterns Chris sees in high-performing clients. His approach is to force the view around the corner: concrete questions about the next five, ten, and twenty years, a specific North Star, and real accountability to it.

He applies the same BHAG thinking, big hairy audacious goal, that Jim Collins and Jerry Porras popularized for companies in Built to Last, but pointed at a person's life instead of a business plan. If there were no limits, what would it actually look like? At 61, running a global advisory practice from a farm in rural Zambia, Chris is candid that he's his own proof of concept.

What Most People Miss

Chris's framework is about mindset and life design, and it works. But there's a piece underneath it that his advisory practice doesn't cover and that we spend most of our time on at Tailored Wealth: none of it is actually available to you unless the money is architected to support it. "Someday" often isn't just a mindset problem. It's also a math problem: whether your portfolio, your liquidity, and your tax picture can actually fund the life you're designing on the timeline you want it. The clients who move fastest from someday to now are usually the ones who've done both halves of the work, the life architecture and the financial plan built backward from that same life, at the same time. One without the other tends to stall.

A Concrete Example: Two Companies, Two Very Different Five-Year Stretches

Chris's own career is the clearest illustration of his framework. At Triad Retail Media, he grew the company 45% compounded annually for a decade, adding roughly $100 million in revenue and 100 employees some years. By every external measure, that was a career-defining run. It also coincided with a divorce and a five-year stretch of declining health, which is exactly the "performing without thriving" pattern his framework is built to catch.

Between Triad and his next role at Playwire, he took six months off, deliberate, unstructured time, on the advice of a private equity mentor who told him to say no three times before saying yes to what came next. At Playwire, he helped grow revenue from roughly $20 million to $150 million, comparable in scale to the Triad years, but this time with intentional role design and boundaries built in from the start. Same caliber of business outcome. Fundamentally different personal experience underneath it.

Who This Is For

This is written for the high-earning executive who is hitting every number on paper, comp, title, trajectory, while privately wondering whether the life underneath it is actually the one they wanted or just the one they built by default. If you're performing at a high level but can't say you're thriving, this episode, and the financial planning work that has to run alongside it, is worth your time.

Frequently Ask Question

What is the eight-dimension framework for life architecture?

The eight-dimension framework is a diagnostic tool developed by Chris Giomblanco that evaluates a person's current state across eight core life dimensions: career, health, relationships, finances, spirituality, legacy, personal growth, and community. It's delivered through a 40-question journal that helps executives identify which dimensions are most in need of attention and build toward a North Star that reflects what a fully lived life looks like. It's a useful companion to the financial side of the same question; our own Life Driven Investing approach builds the portfolio backward from the same kind of life picture. Consult a qualified professional for guidance on the financial dimensions of your life plan.

What is the difference between performing at the top and thriving there?

Performing at the top means hitting the numbers, scaling the business, and making every shot in the professional arena. Thriving at the top means the other dimensions of life, health, relationships, purpose, and connection, are also intact when you walk off the field. Chris describes a five-year period at Triad Retail Media where he was growing the company 45% compounded annually while simultaneously going through divorce and watching his health decline. That's performing without thriving. His advisory work exists to help high performers close that gap before a sustained period of damage forces the reckoning.

How do high earners stop living in someday and start designing the life they want now?

The someday mindset, deferring the life you actually want until after the next milestone, is one of the most common patterns Chris sees in high-performing clients. His approach is to force the view around the corner by asking questions about the next five, ten, and twenty years in concrete terms, building a North Star, and holding the person accountable to that picture. For executives who have already done the financial planning work to make a transition possible, the clarity about what to do next is often the missing piece; see how we think about that transition window in When Can You Make Work Optional? Consult a qualified financial planner to assess the financial feasibility of your transition timeline.

What are the early signs that a high performer is not thriving?

The most common early sign, according to Chris, is the feeling that you cannot step even six inches away from the machine without things starting to break. There's no redundancy, no backstop, and no structure that operates independently of your personal presence. This is distinct from simple busyness. It reflects an architecture problem: the absence of intentional design in the systems, the org, and the life around the work. If that feeling persists across multiple roles or companies, it's typically a signal that the architecture of the whole life, including the financial plan underneath it, needs attention. Our take on why an all-or-nothing exit often isn't the answer is in Why Hybrid Living Beats Full Retirement.

How does meditation help high-performing executives?

Chris was introduced to meditation by a cardiologist at Boston University after a battery of tests during a period of extreme professional and personal stress. He'd previously dismissed the practice entirely. More than a decade later, he describes it as woven into the foundation of who he is and one of the single most transformative shifts in his adult life. Consult a physician before making significant changes to your health or wellness routine.

What is a BHAG and how does it apply to career and life design?

BHAG stands for big hairy audacious goal, a concept Jim Collins and Jerry Porras popularized for companies. Chris applies the same thinking in his advisory work to push clients past the internal voice that says I'm too old or I can't do that. Most high performers constrain their aspirations to what seems reasonable given their current situation; a BHAG forces the question of what's actually possible if the ceiling were removed. At 61, living on a farm in rural Zambia and running a global advisory practice, Chris is his own proof of concept. If you're weighing what your own version of a bigger goal could look like financially, Tired of Corporate, But Not Ready to Quit? is a good place to start. Consult a qualified financial and life planning professional for guidance on the practical feasibility of your goals.

If you're performing at a high level but not sure the life underneath it is actually the one you want, and want to build the financial plan that makes designing it possible, that's exactly what a Free Wealth Strategy Call with the Tailored Wealth team is for.

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