Customarily, retirement is framed as a reward for years of hard work.
What if hard work and achievement are central to who you are?
Walking away entirely can feel like giving up part of your identity. Many Type-A professionals aren’t willing to trade in their laptops and responsibilities for golf clubs and empty calendars — they want challenge, purpose, and an avenue to continue living the way they want to live, even if that means working in some capacity.
That’s why retirement planning for high-achievers needs a different playbook. Accumulating savings is still important, yes, but it’s equally important to create a flexible plan that funds both financial stability and your next vocational decision.
Why Traditional Retirement Doesn’t Fit Type Type-A Professionals
It’s almost cliché: a gold watch at 65, followed by decades of leisure, golf, and travel.
Except ambition doesn’t just turn off at a predetermined retirement age. Many high achievers derive energy, identity, and social connection from their work. Stepping away can create a void that leisure alone doesn’t fill.
Instead of viewing retirement as a hard stop, we encourage Type-A professionals to see it as a pivot point — a transition with open-ended, sand-box-like opportunities. Some transition into advisory roles, consulting, or part-time work that maintains engagement while still easing the pace of the corporate grind. Others launch new ventures, sit on boards, or channel their drive into philanthropy and community leadership.
No matter the avenue, traditional retirement assumes people want to stop. High achievers want to keep going, just differently. That requires a different kind of financial plan.
Building a Retirement Plan That Matches Your Wants and Needs
While your retirement plan should be personalized to your specific Life After Work path, it likely includes a combination of the following:
Retirement income planning. Retirement savings are only half the equation — the real challenge is converting them into sustainable retirement income. That means coordinating withdrawals across 401(k) plans, IRAs, Roth IRAs, and taxable brokerage accounts to create steady cash flow while minimizing your tax bill.
Flexible income streams. Beyond Social Security and retirement accounts, maintaining taxable brokerage assets or phased withdrawals from a Roth IRA can provide the liquidity to fund new ventures or passion projects without disrupting your long-term security. For some, layering in an annuity can provide guaranteed income that complements Social Security benefits.
Tax-efficient strategies. Every withdrawal decision has income tax consequences. Converting IRA assets to Roths during lower-income years, sequencing withdrawals deliberately, or leveraging charitable vehicles (like donor-advised funds) can minimize taxes while aligning with your financial goals.
Thoughtful asset allocation. A portfolio should balance growth and stability, accounting for the reality that you may stay active longer than average retirees. Diversification across equities, fixed income, and alternative assets helps protect against volatility, while still providing the upside needed to fund decades of retirement.
Healthcare planning. Medicare eligibility begins at 65, but gaps before (or even after) can create large expenses. Factoring in premiums, supplemental coverage, and long-term care and life insurance helps ensure health doesn’t become a financial wildcard. Knowing when and how to enroll in Medicare or supplemental plans is critical to avoiding costly penalties.
Estate and legacy considerations. From wills and trusts to philanthropic giving and admittedly heavy conversations with loved ones, estate planning is a complex subject that should never be ignored, no matter what retirement looks like for you. Yet, only about a third of Americans have even a basic estate plan.1
The common thread is flexibility. A plan that accounts for evolving income, health, and lifestyle goals helps keep your options open — whether that means scaling back, doubling down, or reinventing yourself altogether.
The Challenge of Retirement Planning: Balancing Financial Goals With Lifestyle Goals
Retirement decisions don’t exist in a vacuum. One choice sets off a chain reaction that affects both your finances and your lifestyle. Below are a few common decisions, along with the possible tradeoffs and impacts that could ensue.
Work Part-Time Into Your Late 60s
You trade 70-hour weeks for 20-hour consulting gigs and advisory services, still dipping a toe in the water without swimming laps every day. These days, it’s fairly common — almost 4 in 10 workers expect to retire in their 70s or never retire at all.2 And more than half plan to work part-time, typically to bolster income or simply stay active.
Financial Impact: Continued income delays the need to tap retirement accounts, giving investments more time to grow. Social Security benefits increase the longer you wait, and withdrawals can be postponed. That said, while no one’s complaining about larger accounts and higher lifetime retirement benefits, they do create a more complicated tax picture once you do start taking withdrawals.
Lifestyle Impact: Staying engaged preserves your sense of identity and maintains professional networks, though it may limit flexibility for long trips or extended family time.
Retire Early to Travel Extensively
Perhaps you’re used to round-the-world itineraries — but instead of client dinners, it’s wine tastings in Tuscany and hiking in Patagonia with the family.
Financial Impact: Higher withdrawals in your 60s can strain long-term sustainability, especially if market volatility hits early. You’ll also need to bridge the gap in healthcare coverage before Medicare at 65, which can mean tens of thousands in premiums.
Lifestyle Impact: Provides more active years for travel and adventure when health and energy are highest. Later in retirement, though, you may need to scale back spending to compensate.
Launch a Second Venture Post-Career
You’ve acquired invaluable knowledge in your field and cultivated a robust network, so you decide to build something of your own. This might sound farfetched, but it’s more common than you’d think — 22.8% of new businesses are launched by people aged 55 to 64.3
Financial Impact: New income can reduce the drawdown pressure on your retirement accounts and extend portfolio longevity. However, many ventures require upfront capital, carry risk, and can complicate your tax picture with business deductions, self-employment taxes, and liability exposure.
Lifestyle Impact: Sparks your ambition and creativity, opening the door to newfound purpose. But it may push leisure and family priorities further down the road.
Relocate or Downsize to Free Up Capital
Maybe you’ve spent decades in the Bay Area. Once work slows down, you decide to swap city living for a quieter town — or trade the five-bedroom house for something smaller and simpler.
Financial Impact: Downsizing or relocating can unlock substantial home equity, reduce liabilities like mortgages and credit cards, and lower ongoing expenses such as property taxes, utilities, and insurance. This freed-up capital can boost your retirement savings or fund lifestyle goals without leaning so heavily on 401(k) plans or other retirement accounts.
Lifestyle Impact: A simpler financial picture can mean less stress and more freedom to pursue what excites you — travel, hobbies, or new community involvement.
Of course, these are just examples with general assumptions. The key takeaway is every lifestyle choice has ripple effects in income, taxes, withdrawals, and long-term sustainability. A fiduciary financial planner can help weigh these tradeoffs objectively, since they’re obligated to put your best interests first.
How Financial Professionals Help Guide Your Retirement Path
Retirement planning is a full-time job — one that stacks on top of already long hours, family commitments, and other responsibilities. Like buying a house, starting a business, or raising kids, it takes careful preparation and ongoing attention.
A financial advisor can lighten the load and bring clarity and cohesion to the process through:
- Scenario modeling. An experienced investment advisor can also model different income planning strategies and variables to help answer the age-old question: “How much money is enough to retire comfortably and do what I actually want to do?”
- Stress testing. See how your plan holds up against a market downturn, rising healthcare costs, or other unexpected challenges.
- Tax strategy. Identify opportunities for Roth conversions, charitable giving, and smart withdrawal sequencing to minimize lifetime taxes.
- Portfolio alignment. Fiduciary advisors design an investment strategy that balances growth, income, and volatility management — tailored to your timeline, even if it changes.
- Sounding board support. Outside of spreadsheets and models, advisors help tackle the emotional side of retirement — the identity shift, the lifestyle transition, and the question of what comes next.
Perhaps you’ve run the numbers, outlined some retirement goals, and even talked out some scenarios. But if you still have questions, concerns, or lingering doubts, you’re not alone.
Download our free guide, Retirement Redefined: Your Guide to Life After Work to start exploring what your own unconventional retirement could look like.
Sources
- Caring.com, “2024 Wills Survey”
- Transamerica Center, “Retirement in the USA: The Outlook of the Workforce“
- Ewing Marion Kauffman Foundation, “Trends in Entrepreneurship Series”
