Capitalist Investor

Phased Retirement: Financial Planning Considerations for a Gradual Transition

The traditional retirement model of working until a predetermined age and then leaving the workforce entirely is evolving. For established professionals, phased retirement may provide greater flexibility, but it also introduces financial considerations that deserve careful evaluation.

In this episode of The Capitalist Investor, Tony Zabiegala, CRPC®, and Derek Gabrielsen, CRPC®, discuss how transitioning into part-time employment, consulting, or reduced professional responsibilities can affect retirement income, Social Security decisions, healthcare benefits, taxes, and long-term financial planning.

The conversation also addresses the practical limitations of employer-sponsored phased retirement arrangements and the importance of evaluating alternative income scenarios before changing an established retirement strategy.

For individuals who have spent decades accumulating wealth, a successful transition into retirement requires more than sufficient assets. It requires a plan that accounts for changing income, spending expectations, and personal priorities.

AI Investment Spending, Portfolio Concentration, and Retirement Risk

The growing financial commitments behind artificial intelligence are raising important questions about corporate profitability, market concentration, and portfolio diversification. For investors approaching or living in retirement, understanding these risks is an important part of preserving accumulated wealth.

In this episode of The Capitalist Investor, Tony Zabiegala, CRPC® and Derek Gabrielsen, CRPC® examine the capital expenditures of major technology companies, the pressure on free cash flow, and the implications of concentrated exposure to large-cap technology stocks.

They also discuss potential changes to Social Security, Medicare, and retirement-related tax provisions following the midterm elections, including the uncertainty surrounding future legislation.

The discussion emphasizes thoughtful diversification, awareness of policy changes, and maintaining a retirement strategy that accounts for both market and legislative uncertainty.

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Social Security benefits are set to receive a 3.6% cost of living adjustment in 2027, giving millions of Americans a larger monthly check. But rising Medicare premiums and other retirement expenses could reduce how much of that increase retirees actually feel.

In this episode, the team breaks down what the new COLA means for Social Security recipients, how Medicare and prescription drug costs factor into retirement income, and why inflation can affect retirees differently than younger workers.

They also discuss the long term funding challenges facing Social Security, possible changes to how future cost of living adjustments are calculated, and why retirees should make sure their financial plans account for rising healthcare costs and potential changes to future benefits.

Private equity, private credit and private real estate could soon become more common inside 401(k) plans, opening the door to investments that have traditionally been limited to institutions and wealthy investors.

In this episode, the team breaks down the potential benefits and risks of adding private assets to retirement accounts, including diversification, higher fees, limited liquidity and the difficulty of valuing investments that do not trade publicly.

They also discuss how these investments could eventually appear inside target date funds, why education and due diligence will be critical and what retirement savers should understand before allocating part of their 401(k) to more complicated private investments.

One of the most influential voices in retirement research has changed her thinking on three major planning topics, and those shifts could have real implications for retirees and do it yourself investors.

In this episode, the team breaks down why retirement planning involves much more than simply choosing investments, including taxes, Social Security, Medicare, income planning and withdrawal strategies. They also discuss the limitations of target date funds as investors move from saving for retirement to actually living on their portfolios.  

The conversation also examines TIPS and other fixed income strategies, why inflation protected securities may not work exactly the way many investors expect and why owning equities can play an important role in protecting purchasing power over the long term. 

With the end of 2026 approaching, there are several important retirement planning deadlines that could impact your taxes, savings and Medicare costs heading into the new year.

In this episode, the team breaks down three key areas to review before year end: maximizing 401(k) contributions and catch up provisions, completing Roth conversions before the December 31 deadline and preparing for Medicare open enrollment.

They also discuss the new Roth catch up rules for higher earners, how Roth conversions can affect future Medicare premiums and why waiting until the last minute could create unnecessary complications.

If you’re nearing retirement or already retired, now is the time to review your numbers and make sure you’re not missing an important year end planning opportunity.

The baby boomer retirement wave isn’t coming, it’s already here.

In this episode of The Capitalist Investor, the conversation focuses on what record numbers of Americans reaching retirement age could mean for Social Security, Medicare, the labor market, housing, and retirement planning. The discussion covers the growing strain on Social Security, rising healthcare costs, retirement readiness, the concentration of wealth among older Americans, and how a massive generational shift could affect markets and the economy in the years ahead.

They also discuss why near-retirees may want to prepare for the possibility of reduced Social Security benefits and the importance of building additional income sources into a retirement plan. 

For individuals approaching or already in retirement, retirement account structure can become just as important as investment performance. Decisions involving 401(k) plans, traditional IRAs, Roth IRAs, rollovers, and future required distributions can have meaningful tax and planning implications.

In this episode, the discussion explores why substantial retirement assets often migrate from employer-sponsored plans into IRAs and what investors should consider once that happens. Topics include traditional versus Roth contributions, backdoor Roth strategies, spousal contributions, income and deductibility limits, in-service distributions, investment flexibility, fees, and the importance of evaluating future tax brackets.

The larger point is that there is no universally correct retirement account strategy. Contributions, conversions, and rollovers should be considered within the context of an individual's broader financial and retirement plan.

Changes to the tax code can have meaningful consequences for retirement planning, particularly when provisions include income limits, expiration dates, and different rules depending on age or account type. 

In this episode, Tony Zabiegala and Derek Gabrielsen review several tax provisions affecting retirees and families. Topics include the temporary senior deduction, current tax brackets, estate tax exemptions, Roth conversion timing, new Trump Accounts for minors, and enhanced catch-up contribution limits for certain workers approaching retirement. 

The discussion emphasizes understanding how these rules may apply to an individual situation rather than treating broad tax changes as universally applicable.

As 2026 enters its final third, investors face an unusual combination of strong market fundamentals and several potential sources of volatility. 

In this episode, Tony Zabiegala and Derek Gabrielsen examine what has supported the market so far, including broader market participation, a rotation from growth toward value, and earnings and revenue growth. They also consider what could challenge that outlook, including Federal Reserve uncertainty, the midterm elections, geopolitical developments, energy prices, and the possibility that current earnings strength represents an unusually favorable environment. 

The conversation emphasizes diversification, appropriate risk tolerance, and maintaining a disciplined investment plan rather than reacting to momentum or attempting to move in and out of the market.