Hybrid Retirement: Work on Your Terms & Secure Your Future | Dan Pascone | Tailored Wealth

Answer Box: TL;DR

Hybrid retirement lets you make work optional—without walking away from income, purpose, or momentum. In this video, Dan explains how to design a “work-optional” life by shifting from a traditional full-stop retirement into a flexible model that blends part-time or consulting work with sound financial planning. He walks through four practical steps: redefining work on your terms, getting clear on your lifestyle and income needs, using lower income in hybrid retirement for strategic Roth conversions, and testing your new lifestyle with a “mini retirement” before fully stepping away.

Key Takeaways

Hybrid retirement = work on your terms, not your employer’s.
- Retirement doesn’t have to mean stopping work—it can mean choosing when, where, and how you work.
- Hybrid retirement makes work optional rather than necessary to cover your living expenses.
- For many professionals, this feels more natural than going straight from full-time work to a hard stop.
Step 1: Redefine what “work” looks like.
- Shift away from the traditional 9–5 grind into:
  - Freelancing or independent consulting
  - Fractional or part-time roles
  - Turning a hobby or passion into income
- The goal is to stay engaged, keep earning something, and regain control over your schedule.
Step 2: Get financial clarity on your lifestyle needs.
- Outline your real-world costs:
  - Travel and experiences
  - Health care
  - Everyday living expenses
- With hybrid retirement, part-time income means you may need far less portfolio withdrawals than you think.
- Supplement work income with passive income from dividends, rental properties, or other investments.
Step 3: Use hybrid retirement to optimize taxes.
- Working less can drop you into a lower tax bracket, creating planning opportunities.
- Dan suggests using those years to consider converting traditional retirement accounts to a Roth IRA, locking in today’s rates.
- The payoff: more tax-free withdrawals later in retirement if conversions are done thoughtfully.
Step 4: Test the waters with a mini retirement.
- Before fully exiting your career, try a mini retirement or sabbatical.
- This “trial run” helps you:
  - See how your spending and cash flow actually feel
  - Adjust your work mix and schedule
  - Confirm that your lifestyle aligns with your goals
- It’s a way to refine your plan while you still have flexibility to course-correct.
Hybrid retirement is about freedom and security, not just less work.
- The goal is to work on your terms while maintaining financial security.
- The earlier you plan, the more options you’ll have—around timing, type of work, and tax strategy.
- Done right, hybrid retirement can balance purpose, flexibility, and long-term security.

Key Moments

(00:00) – Rethinking retirement. Dan opens by challenging the idea that retirement has to mean stopping work and introduces the concept of hybrid retirement: work as optional, not required.
(00:00–00:39) – Dan’s role & the hybrid retirement frame. He introduces himself as founder and CEO of Tailored Wealth and explains that he helps people design financially secure retirement plans that truly fit their lifestyle goals, using a hybrid approach instead of a full-stop transition.
(00:39–01:22) – Step 1 & 2: Redefine work and get clarity. Dan walks through redefining work (freelancing, consulting, hobbies-as-income) and highlights how to map out lifestyle costs and use part-time work plus passive income to support them.
(01:22–02:02) – Step 3 & 4: Tax strategy and mini retirement. He explains how earning less can open up tax planning windows (like Roth conversions) and encourages viewers to test their plan with a mini retirement before fully stepping away.
(02:02–end) – Mindset & call to action. Dan reinforces that hybrid retirement is about working on your terms while staying financially secure and invites viewers to consider whether a hybrid or traditional path fits them, and to engage with more retirement strategy content.

Episode Summary

In this short but powerful video, Dan reframes what retirement can look like for modern professionals. Instead of viewing retirement as a binary switch—full-time work one day, zero work the next—he introduces the concept of hybrid retirement, where work becomes optional but still part of a purposeful, flexible life. The core idea is simple: you design a stage of life where you choose when, where, and how you work, without being financially dependent on a paycheck.

He outlines four practical steps. First, redefine work: move away from the traditional 9–5 schedule into consulting, freelancing, or monetizing a passion. This allows you to stay engaged and keep earning while gaining control over your calendar. Second, get financial clarity by mapping out your lifestyle costs—travel, health care, and daily expenses—and then layering in part-time work plus passive income (like dividends or rental income) so your portfolio doesn’t have to shoulder the full burden immediately.

The third step is to optimize your tax strategy. Earning less in hybrid retirement can drop you into a lower tax bracket, which creates a window for smart moves like converting traditional retirement accounts to a Roth IRA. That can help you lock in current tax rates and build more tax-free income down the road. Finally, test the waters with a mini retirement—a limited trial of your hybrid lifestyle to see what feels right, what needs adjustment, and whether your plan supports the way you actually want to live.

Throughout, Dan emphasizes that hybrid retirement isn’t about doing nothing; it’s about intentionally designing a life that balances freedom, purpose, and financial security. The earlier you start planning, the more options you’ll have, from how much you work to how you structure your income and taxes. He closes by inviting viewers to reflect on whether they prefer a hybrid path or a full-stop retirement—and to keep learning about smart retirement strategies that support a work-optional future.

Full Transcript

Dan: What if retirement didn’t mean stopping work, but just working on your terms? Imagine choosing when, where, and how you work without worrying about money. That’s the power of what I call hybrid retirement, where work is an option but not a necessity.

Dan: I’m Dan Pascone, founder and CEO of Tailored Wealth, and I help people design financially secure retirement plans that actually fit their lifestyle goals. Instead of going from full-time work into complete retirement, a hybrid approach allows you to transition with more freedom and flexibility.

Dan: Here’s how to make hybrid retirement work for you. Step one, redefine work. Shift from the 9-to-5 grind into freelancing, consulting, or turning a hobby into income. Stay engaged, keep earning, and gain complete control of your schedule.

Dan: Step two, get financial clarity. Outline your lifestyle costs like travel, health care, and day-to-day living expenses. With part-time work, you may need far less than you think. You can supplement your earnings with passive income from dividends, rental properties, or other investments.

Dan: Step three, optimize your tax strategy. Earning less in retirement could lower your overall tax bracket. Use this to your advantage by converting traditional retirement accounts to a Roth IRA. Lock in today’s tax rates and set yourself up for tax-free withdrawals in the future.

Dan: Step four, test the waters. Try a mini retirement before officially stepping away from work. This trial run helps to refine your plan and ensure that your new lifestyle aligns with your goals.

Dan: Hybrid retirement isn’t about stopping work. It’s about working on your terms while maintaining financial security. And the earlier that you plan, the more options that you’ll have.

Dan: Would you consider a hybrid retirement, or do you prefer a more traditional full stop? Let’s discuss in the comments below. And if you want more insights on smart retirement strategies, hit that like button and turn on notifications so you never miss an update.

Resources & Concepts Mentioned

Hybrid retirement: A phased model where you reduce or reshape work instead of stopping entirely, making work optional rather than required.
Consulting/freelancing: Common hybrid-retirement paths that allow flexible schedules and selective projects.
Passive income: Income from sources like dividends, rental properties, or other investments that can supplement part-time work.
Roth IRA conversions: Moving money from pre-tax retirement accounts into a Roth IRA, paying tax now to pursue tax-free withdrawals later (subject to rules and eligibility).
Mini retirement: A trial period where you temporarily live your intended retirement lifestyle to test finances, habits, and fit.

FAQs

What is hybrid retirement, and how is it different from traditional retirement?

Hybrid retirement blends part-time or flexible work with financial independence, so work becomes optional rather than mandatory. Instead of going from full-time work straight into a full stop, you scale back, consult, or pursue passion projects while your savings and investments support the rest. Traditional retirement usually assumes zero earned income and full reliance on your portfolio and benefits.

Who is hybrid retirement best suited for?

Hybrid retirement often resonates with business leaders, executives, and high-earning professionals who enjoy their work but want more flexibility and control. It’s also well-suited for people who worry about the emotional or social shock of stopping work entirely, or who prefer to keep some earned income flowing to reduce pressure on their portfolio.

How does hybrid retirement affect how much I need to save?

Because you may continue to earn income through consulting, freelancing, or part-time work, you may not need as large a nest egg on day one of retirement as a traditional “full stop” retiree. That said, you still need a plan that maps out expected earnings, spending, and portfolio withdrawals. Hybrid retirement can reduce the draw on your investments, but it doesn’t remove the need for a disciplined plan.

What are the tax planning opportunities in a hybrid retirement?

With lower earned income, you may be in a lower tax bracket, which can open up opportunities such as Roth conversions from traditional retirement accounts. Converting in lower-tax years can help you build more tax-free income later and manage required minimum distributions (RMDs) down the road. As always, specific moves should be coordinated with a tax professional.

Why should I try a mini retirement before fully stepping away from work?

A mini retirement gives you a real-world test of your spending, routines, and emotions before you fully transition. It can reveal whether your planned lifestyle is realistic, whether your budget feels comfortable, and how much structure or social connection you need from work. It’s easier to adjust course while you still have flexibility than after a full, irreversible exit.

Disclaimer

This video and written summary are for educational and informational purposes only and do not constitute financial, tax, or legal advice. They do not create a client relationship with Tailored Wealth or any related entity.

Retirement planning, hybrid retirement structures, Roth conversions, and tax strategies all involve risks and trade-offs that depend on your specific circumstances. Before making any decisions, you should consult with:

A licensed financial advisor or planner
A qualified tax professional (CPA or EA)
Legal counsel, where appropriate

Any examples mentioned are illustrative only and not guarantees of results. Actual outcomes will vary based on your personal situation, market conditions, and changes in laws or regulations.

Next Steps

Define your hybrid vision: Write down what “work on your terms” actually looks like—hours, type of work, and income goals.
Map your lifestyle costs: Estimate travel, health care, and everyday expenses to see how much your portfolio needs to cover vs. part-time income.
Explore tax opportunities: Talk with a professional about whether lower-income hybrid years could be a good time for Roth conversions or other tax strategies.
Design a mini retirement: Plan a 3–6 month trial of your hybrid lifestyle to test spending, routines, and overall fit.
Build a written plan: Integrate hybrid work, investments, and tax planning into a cohesive retirement roadmap you can adjust over time.

Hybrid retirement can give you the best of both worlds—purposeful work and real freedom—if you take the time to design it intentionally.