Working on Your Own Terms [On-Demand Webinar]

Working on Your Own Terms: A Guide to Semi-Retirement

Presented by Libby Muldowney, Financial Advisor, Savant Wealth

Hi everyone, and welcome to today’s Savant Live webinar. We’re going to talk about Working on Your Own Terms: A Guide to Semi-Retirement. My name is Libby Muldowney. I’m a financial advisor here in Rockford, Illinois. I’ve worked in financial services since 2002 and have been with Savant since 2008. For the past 11 years, I’ve worked closely with individual households and families to help them build their ideal financial futures. I’m excited to be your host today and thank you for joining us.

Before we begin, a quick but important disclosure: this presentation is for informational and educational purposes only. It should not be considered individualized financial advice. There will be an opportunity at the end to schedule a time with an advisor if you’d like to discuss your situation further.

Let’s Talk About Semi-Retirement

Today’s topic is about designing a new kind of retirement—one that doesn’t follow the traditional script. We’ll start by envisioning your future and defining what we mean by semi-retirement. Then we’ll walk through how to replace your paycheck, how healthcare fits into your plan, and how to minimize taxes along the way.

When I talk about semi-retirement, I’m not just talking about leaving your full-time job and working a couple days a week or starting a side hustle. It’s bigger than that. It’s about reimagining the whole concept of retirement and building a new life phase that blends work, purpose, and personal time.

Why Things Have Changed

Historically, retirement had a pretty linear timeline: you go to school, build your career, work full-time for 30 to 40 years, and then retire at 65. That made sense for previous generations, especially because many people had pensions. Pensions gave you a fixed income in retirement—you knew how much you’d get and when. It was a very structured, employer-driven retirement model.

But today, that model doesn’t fit anymore. Most people don’t have pensions. We’re living longer, we want more fulfillment, and we’re responsible for saving for our own retirements. The old idea of “all work until 65, then all play” doesn’t match our modern lives.

In fact, many people tell us that full-time leisure doesn’t feel fulfilling over the long term. When retirement lasts 30+ years, you need more than just rest and relaxation. You need purpose, structure, and flexibility.

A Two-Phase Retirement

That’s why I like thinking about retirement in two phases. In your primary career years, you maximize income and savings—even if the work isn’t your passion. Then, you transition to a second phase that blends work and lifestyle in a more meaningful way.

Thanks to remote work and more flexible job options, you might be able to live somewhere new, travel more, or take on part-time or consulting work that gives you purpose and freedom.

You might not need to earn what you did before. Big expenses like college tuition or retirement contributions may be behind you. Maybe you were earning $100,000 and saving 20%—you could earn $80,000 and be in the same financial spot, or even less, depending on your goals.

We’ve seen people use this second phase to move closer to aging parents or grandchildren, pursue work in the nonprofit space, or even take jobs that offer benefits without full-time hours.

Where Do You Start?

You begin with a vision. Ask yourself: What do I want this phase of life to look like? What matters most to me? From there, set goals. Maybe you want a remote job or work in a cause-driven organization. Once you define the lifestyle, we can build the budget—and then take action.

For example, you might say, “I want to have $X in savings so I can afford to reduce my hours and still draw $Y per year.” From there, we build the strategy.

Replacing Your Paycheck

If you cut back on hours or leave a full-time job, where will your income come from? It could be a combination of:

• Part-time work
• Social Security
• Pensions
• Retirement savings (401(k), IRA, Roth, etc.)
• Taxable investment accounts
• Health Savings Accounts

And it’s important to remember—you might not need to replace your full paycheck. Your lifestyle and budget will likely look different than during your peak earning years. Many expenses may drop off, and that changes how much you need to draw.

Social Security Timing

The earliest you can claim Social Security is 62, but that’s a reduced benefit. If you wait until your full retirement age—around 66 or 67—you’ll receive more, and if you wait until age 70, the monthly amount increases further.

So how do you decide when to claim? It depends. If you defer, you’ll receive more if you live a long life—but you need to support yourself in the meantime. If you claim early and live into your 90s, you may leave money on the table.

A financial advisor can help you run the numbers. We look at longevity, health, income needs, and other assets to help determine the best timing for your situation.

Healthcare Before Medicare

If you retire before 65, healthcare is a huge factor. Your options include:

• COBRA (temporary extension of your employer’s plan)
• Your spouse’s employer plan
• The ACA exchange (with potential subsidies based on income)
• Part-time jobs that offer benefits
• Health Savings Accounts (HSAs)

Sticker shock is real. Coverage could cost $5,000–$12,000 per person per year before Medicare kicks in. Planning for this is essential.

If you’re still working, consider contributing to an HSA if you’re eligible. It offers triple tax benefits—tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses.

Retirement Accounts & Draw Rates

Different accounts have different rules. For example, traditional retirement accounts have early withdrawal penalties before age 59½. So, if you plan to retire early, you’ll want to diversify your savings into both retirement and non-retirement buckets.

We also want to look at a sustainable draw rate. A 4% annual withdrawal from your portfolio is a good general guideline. If you’ve saved $1 million, that means you could draw $40,000 per year to supplement other income sources.

If that’s not enough, you can adjust by working a bit longer, saving more, or shifting expectations. It’s all about balance.

Investment Strategy and Risk

You don’t want to be too aggressive or too conservative. A balanced portfolio with both stocks and bonds helps manage market volatility. During downturns, you can draw from more stable assets like bonds, then rebalance when markets recover.

Planning tools like Monte Carlo simulations can help test your plan under many market scenarios. We aim for a 75–90% success rate—not perfection. Flexibility is key. We revisit the plan regularly and adjust as life unfolds.

Tax Planning in Retirement

This is a big one. Retirement is the time to think in terms of lifetime tax planning, not just year-to-year.

Different income sources are taxed differently. By pulling from the right accounts at the right time (traditional, Roth, taxable), we can keep you in lower tax brackets and reduce the total taxes you pay over your lifetime.

We also use strategies like:

• Asset location (placing different investments in the most tax-efficient accounts)
• Tax-loss harvesting
• Roth conversions (in low-income years)

Taxes get more complicated in retirement—especially with RMDs (required minimum distributions), stock options, or deferred compensation. This is where a financial planner can help integrate your investment and tax strategy.

Wrapping Up

We spend so much time planning for our kids, our careers, and our parents—but not always for ourselves. And studies show people spend more time planning a one-week vacation than planning for retirement.

But this isn’t just about retiring. It’s about designing your next chapter with intention. A traditional retirement model doesn’t work for many of us anymore—and that’s okay.

If you’re feeling overwhelmed, flip the perspective. Imagine yourself at age 85 looking back. What do you wish you had done? Let that guide you.

We’re here to help you build a flexible, personalized plan that works for your goals and lifestyle. We can help with the logistics—savings, budgeting, investments, healthcare, taxes—and help you uncover opportunities for greater balance and meaning.

Next Steps:

✅ If you’d like to meet with a Savant advisor, use the link in the chat to schedule a 15-minute complimentary call.

📚 For additional resources, visit savantwealth.com/guides to download free guidebooks and checklists.

Thank you so much for joining me today. I’m Libby Muldowney, and it’s been a pleasure to spend this time with you. Take care!