Rethinking Retirement: Planning Options for People Who Love to Work

“When will you retire?” As a high-achieving professional, it’s a question that might make you uncomfortable. The traditional retirement narrative may not resonate with your reality as you juggle a demanding career while planning for your family’s future.

If you find fulfillment in your work and can’t imagine giving it up entirely, it’s time to reframe what retirement means for you. Let’s consider retirement transition opportunities As an ambitious, career-driven professional, it can help to reframe retirement as a transition into the next phase of your life instead of the end-all be-all it’s often made out to be. This means you don’t have to forget the skills you’ve developed over the past several decades, and instead, think about a productive, meaningful way to continue your journey through your retirement years.

Depending on your skillset and work situation, together we can consider a retirement transition in one of the following ways:

● Owner to consultant - As a business owner, we can consider transitioning out of your primary operator role and into a consulting role to support your business without as much stress.

● Full-time to part-time - Full-time executives may want to continue their work without committing as many hours. Your employer may be happy for you to continue lending your expertise at a reduced workload.

● Leadership to mentorship – One option is to use your decades of experience to lead the next generation of talent within your organization, through industry groups, or through direct mentorship on your own.

● Specialist to advisory - Transition from deep specialization in one area to using your skills across various projects in an advisory role.

● Career to philanthropy - Consider using your professional skills to support causes that matter to you through volunteering or foundation work.

Map out your days

One concern we often hear from career-driven professionals is: How will I spend my days if I’m not working? The anxiety is real, especially if your identity is tied to your career achievements. To help answer this question, we’ve suggested creating a weekly schedule (like the one below) and fill each slot with how you plan to spend your retirement days.

If you can’t fill 16-18 of these 21 slots with fulfilling, meaningful activities, you may struggle with the transition to full retirement. And that’s ok. This exercise will help reveal whether you’re ready for a significant life change.

Trial run retirement with a “staycation”

What if there were a way to test out a full retirement without committing to this major life decision?

1-2 years before your planned retirement, consider taking an extended “staycation” to test-drive what retirement might feel like. During this trial run, eliminate all work-related distractions and try to fill your days at home with what you want to do most. A staycation can reveal whether you’re truly ready for a lifestyle change.

For some, this break from work can feel uncomfortable and reinforces their desire to continue working. For others, the freedom from work feels liberating and comes with the recognition of the benefits of scaling back professionally to enjoy other aspects of life.

This experiment provides valuable insights without the permanence of an actual retirement decision, allowing you to adjust your transition plan while there’s still time to prepare for your next chapter.

Don’t forget about tax efficiencies

Even if you plan to forgo a traditional retirement, tax optimization is still essential to preserving and growing wealth. Whether you transition to consulting, reduce your workload, or pursue philanthropic work, the right tax strategies can impact your long-term financial flexibility and help you achieve your goals more efficiently.

Here are some tax strategies we can help you consider:

● Exploring backdoor Roth IRA conversions if your income exceeds contribution limits.

● Using tax-loss harvesting to offset capital gains.

● Looking at qualified business income deductions if you’re a business owner.

● Building a tax-diversified portfolio with pre-tax, Roth, and taxable accounts.

● Exploring advanced tax strategies like a donor-advised fund or qualified charitable distributions.

Retirement isn’t all-or-nothing

Retirement isn’t a binary. This simple reframing can comfort ambitious professionals who find the prospect of stopping work unsettling. At Affinity Wealth Management, we work with ambitious professionals who are building extraordinary lives, not just retirement accounts. We understand that your relationship with work is complex, and traditional retirement advice doesn’t fit your reality. Our approach starts with understanding what experiences make up your best life, then we align your financial decisions with those dreams and goals.

Whether you’re concerned about the tax implications of scaling back, funding college while saving for your own future, or simply needing reassurance that you’re making the right choices, we’re here as your trusted partner.

Contact an Affinity financial advisor today to begin crafting a future as ambitious as you are. Learn about our Connect Meeting here!

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