Strategic Approaches Beyond Traditional Retirement
Many high achievers reach a turning point where they start thinking beyond their current success.
They start thinking differently about their future, asking sharper questions: Which of my expenses are fixed, and which might change dramatically? Do I want one home or two? Should I keep working, whether for pay or fulfillment? Is this the season to give back more intentionally?
If you’re beginning to ask questions like these, you’re not alone. You’re looking for a thoughtful transition, one that balances opportunity, flexibility, and long-term security.
What’s Really Driving Your Desire for Change?
When clients come to us expressing this sentiment about loving their work but thinking about what’s next, we’ve found that one of three underlying motivations is usually driving their thinking:
1. Financial Confidence.
You think you have enough money to retire and want validation to step away. You’ve hit your financial goals and are wondering if you’ve earned the right to pivot. The question isn’t whether you’re capable of continuing—it’s whether you need to.
2. Time Awareness.
Here, the concern isn’t money, it’s time. You’re worried you won’t have enough years left to do everything you want to accomplish outside of work. You’re asking whether continuing at your current pace is necessary for your goals or if you’re working beyond what’s required for your future security.
3. Passion Pull.
You’re either burned out or powerfully drawn to a new direction. You need to understand how quickly you could make a transition financially feasible. You’re ready to move toward something different, regardless of conventional timelines.
The beauty of recognizing which category you fall into is that it fundamentally shapes how to approach your planning. But before we dive into the numbers, we need to address the emotional landscape of this transition.
Moving Beyond the All-or-Nothing Mindset
If you love what you do and have the energy to continue, that’s great. You can keep working as long as you want to. But the conversation can’t stop there.
We can start with these questions: What specifically do you love about your work? What would you worry about losing if you walked away? What would you be excited to gain if you stepped back? And, critically, what options exist between your current situation and full retirement?
It can be very important for spouses to be on the same page as well. Especially if one spouse is ready to retire and the other wants to keep working.
What we consistently see among the most successful transitions is that people don’t just retire. They transition with purpose. They have plans for what comes next, whether that’s a passion project, strategic volunteering, part-time consulting, or starting something entirely new. They’ve thought creatively about where they want to live, how they want to spend their time, and what “giving back” looks like for them.
The Financial Reality Check
Here’s where most high achievers get tripped up. They make assumptions about their financial flexibility that are often unnecessarily conservative, and these assumptions can keep them trapped in situations longer than necessary.
Misconception #1: Healthcare Before 65
By far the biggest misconception we encounter is that you can’t retire before Medicare eligibility and still access reasonable healthcare. This simply isn’t true, but it requires strategic planning and an understanding of your options.
Misconception #2: Underestimating Portfolio Power
Most successful professionals underestimate how far their investments can carry them and for how long. They’re used to thinking about their wealth in terms of their business or salary, not as a sophisticated income-generating asset.
Misconception #3: The Pre-Tax Income Trap
This is a big one. If you’re accustomed to a $300,000 salary yielding $150,000-$180,000 in take-home pay ($12,500-$15,000 monthly), you might assume you need $300,000 in portfolio income to maintain your lifestyle. But $300,000 in portfolio income typically yields closer to $240,000-$280,000 take-home ($20,000-$23,000 monthly).
Why? Portfolio income isn’t subject to Social Security and Medicare taxes. Much of it may be taxed as capital gains rather than ordinary income. And you’re no longer contributing to retirement plans, which further increases your take-home amount.
The Unique Planning Considerations for Flexible Transitions
When you have flexibility in how you transition, whether that’s stepping back gradually, taking a sabbatical, or changing career directions entirely, several unique planning opportunities emerge:
Income Phases and Tax Strategy
If you’re retiring before 59½, you’ll likely have different income phases throughout your retirement years. This creates significant opportunities for tax optimization over your entire lifespan as opposed to the more narrow “year by year” approach.
Examples of strategies that may emerge from this process include intentional income realization via Roth conversions and capital gains harvesting. In some cases, investors may be able to divest from highly appreciated positions at 0% tax or pay an average tax rate of 15% on income they deferred into retirement plans when their marginal tax rate was more like 40%. All while still enjoying their pre-retirement standard of living.
Sequence of Returns Risk
This matters especially for younger retirees but isn’t widely understood. Think of it like this: you can drown in a pool that averages 3 feet deep if you hit the deep end at the wrong time.
Running out of money because of bad timing isn’t acceptable. You can’t control market timing, but you can build a plan that provides reliable income no matter what’s happening in the broader economy. The key is matching your needs with income sources that work regardless of market conditions.
Healthcare Strategy Integration
Planning for healthcare costs and access becomes more complex but also more strategic when you’re not following traditional timelines. This often presents significant planning opportunities across tax, cash flow, and investment considerations.
What “Enough” Really Means
One of the most liberating conversations we have with clients is helping them define “enough.” It’s not just about having a target number; it’s about understanding the difference between living on portfolio income and strategically spending down principal.
Many of our clients discover they have more flexibility than they initially thought. Once they understand their safety net for inflation, healthcare costs, or market downturns, they can make intentional decisions about their transition timeline.
The Integration Challenge
Perhaps the most frustrating aspect of traditional financial planning is the fragmentation. You’re coordinating between your CPA, investment advisor, and estate attorney while opportunities fall through the cracks. When you’re planning a major life transition, this coordination becomes even more critical.
Look for professionals who can coordinate across all areas or serve as the central point that ensures nothing gets missed.
Making the Transition Work
The most successful transitions share several characteristics:
1. They’re gradual.
Rather than flipping a switch, successful transitioners often reduce responsibilities gradually, delegate tasks they don’t enjoy, or shift to more strategic roles.
2. They’re purposeful.
Whether it’s spending more time with family, pursuing a passion project, or contributing to causes they care about, successful transitioners have a clear vision of what they’re moving toward, not just what they’re leaving behind.
3. They’re financially informed.
They understand exactly where their income will come from in each phase of their transition, and they’ve stress-tested their plan against various scenarios.
Your Next Step
If you’re our client and recognize yourself in what we’ve described, these conversations about life transitions are exactly the kind of strategic planning that can make all the difference. We would love to hear any new thoughts this article sparked about your own retirement plans as we continue to partner with you on your journey. To learn more about our approach, visit our homepage.
Josh Markowitz and Ryan Casperson are financial advisors with The Next Level Planning Group, where they specialize in helping high-achieving professionals and business owners navigate complex financial transitions. If you’re beginning to think about your next chapter, we’d welcome the opportunity to explore your options together.