Dillon Cobb Dillon Cobb

Good Planning Requires Nuance

We like simple answers. Yes or no. Buy or sell. All stocks or all cash. But real life doesn’t work that way. Good financial planning isn’t about finding the perfect portfolio—it’s about finding your right mix, the one that helps you live your life and still sleep at night.

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Retirement Is Not a Finish Line. It’s a Big Transition.

Retirement isn’t the end of the road. It’s a major life transition. Your time, your routine, and even your purpose may shift. That can feel overwhelming—but you don’t have to figure it out alone. This post explains how thoughtful planning can turn savings into reliable income and peace of mind, so you can live well and give freely in this next chapter.

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Ask A Doctor If Credentials Matter

Anyone can call themselves a “financial advisor.”
But not everyone is a CFP® (Certified Financial Planner).
Not everyone is a CPA with deep training in taxes and strategy.
And not everyone is required to act in your best interest.

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Simply Focused!

This week, we made a trip to CookChildren’s Hospital near Fort Worth. We were referred to a heart specialist for our daughter. They’re treating her for POTS, a syndrome that can impact the heart.

Fortunately, it’s not affecting her heart. The cardiologist gave her a clean bill of heart health and a plan for how to manage her symptoms.

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Investing for the Long Run

Investing isn’t only about stocks. The same lessons of patience and consistency that grow portfolios also grow friendships, family bonds, faith, and even client relationships. From a 20-year friendship with Mark to my mastermind group over the last 3.5 years, the returns on these long-term investments have been richer than any chart can show.

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The Retirement Transition Series: Loss of Identity

Loss of identity is a major source of grief in retirement, but it rarely gets the attention it deserves. We talk about grief after a divorce or death, but what about when the job title fades? For many, work has shaped their days, purpose, and community. So when that ends, who are we now? This post explores why it feels so disorienting—and what it takes to rebuild purpose in retirement.

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A Grief Observed

How C.S. Lewis’s A Grief Observed helped me sit with grief, doubt, and faith after profound loss — and why embracing the full weight of sadness is part of healing.

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Man's Search For Meaning

When grief fills your life completely, how do you find meaning again? Reflections on Man’s Search for Meaning and A Grief Observed, and how they shaped my faith, priorities, and calling after deep loss.

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Antifragile

A reflection on grief, resilience, and embracing life after loss. How antifragility became a guiding principle for growth through hard seasons.

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What is Essential?

A reflection on Essentialism by Greg McKeown — and how applying its lessons can help you focus on what truly matters, both personally and financially. Why it's core to how Simply Human Advisors serves clients.

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Get To Know Me

A look at why financial planning should go beyond spreadsheets — and how building connection and trust creates a more meaningful and human financial planning experience.

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Eliminate Hurry

Launching my firm was about more than money. It was about slowing down, living with purpose, and serving clients with full presence — not hustle. This is why I limit my practice to those I can serve deeply, without sacrificing what matters most.

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