The Hidden Advantages of ‘Work Optional’ Retirement Planning
Key Numbers*
Net Worth
$18M
Invested Assets
with TrueNorth Wealth
$12M
* Data as of October 2025.
Subject to change.
Developing Legacy Plans Around Charitable Giving
Rachel and Dan are passionate about supporting medical research and educational scholarships.
We helped them develop a giving strategy with two goals: maximize their impact now while they’re still earning, and ensure their charitable wishes carry forward when they pass.
To accomplish both, Rachel and Dan opened a Donor-Advised Fund (DAF), a charitable giving account that can handle their current donations and continue their legacy after they’re gone.
With their DAF in place, they can easily donate appreciated stock directly, avoiding capital gains taxes while maximizing their deductions.
This creates tens of thousands of dollars in annual tax savings, allowing them to give more generously.
We also developed end-of-life planning that structures how their assets will be distributed between family members and charitable causes after they pass away.
The result is a legacy plan that reflects their values, maximizes every dollar, and gives them the confidence that their impact will outlast them.
Rachel and Dan could retire tomorrow. At 60 and 75, with $9 million in invested assets and $1 million in annual income, they’re more than financially secure.
But they love practicing medicine. And continuing to work into their 70s creates strategic advantages traditional retirees can’t access, including significant tax savings, accelerated wealth growth, and planning flexibility that will result in a substantially impactful legacy.
The Vision
Rachel and Dan wanted to keep practicing medicine for as long as they physically could, not because they needed the income, but because they loved the work.
They needed advisors who could maximize the strategic advantages of their “work optional” lifestyle. This meant sophisticated tax planning, wealth optimization strategies, and legacy planning that traditional retirement advice simply doesn’t address.
Meet Rachel & Dan
- Rachel and Dan are both physicians earning approximately $1,000,000 combined annually. Dan is deeply involved in academic medical research, while Rachel maintains a busy clinical practice.
- When they became clients of TrueNorth in 2021, their financial life was scattered. They had accounts spread across multiple brokerages, old employer retirement plans, and assets in Europe from Dan’s earlier career, adding complexity.
- They had also lost trust in their previous advisors. The advisors had sold them expensive annuities and weren’t helping them capitalize on the unique advantages of continuing to work into their 70s.
- They needed advisors who understood that “work optional” isn’t the same as retired, and who could create strategies specifically designed for high earners who choose to keep working.
TrueNorth Wealth Process
Most retirement planning assumes you stop earning income, but Rachel and Dan’s situation required a completely different approach.
We developed strategies that leveraged their continued high income to create tax advantages, accelerate wealth growth, and build a legacy that would have been impossible if they’d followed traditional retirement advice.
Our Strategic Solutions
- We exited their inefficient annuities without surrender charges through careful timing and analysis. The money was repositioned into a transparent, diversified portfolio that better aligned with their goals.
- We consolidated Dan’s scattered pretax accounts from old employers and custodians, rolling them all into his current 401(k). Because he’s still working and participating in his employer’s 401(k), he doesn't have to take RMDs from that account.
- Dan loves his research and has no plans to stop working, so he now avoids RMDs on the entirety of the pre-tax money he’s saved over the course of his career.
- The tax savings are substantial. Their high annual income combined with RMDs would have resulted in a massive annual tax bill. Now, he doesn’t have to worry about paying taxes on money he doesn’t need yet.
- We also took over coordination with their estate planning attorney, CPA, and insurance agents. This means Rachel and Dan have a single point of contact for all financial questions, instead of managing multiple relationships.
Where They Are Now
Rachel and Dan are continuing to practice medicine because they want to, not because they have to. Dan pursues research projects based purely on intellectual interest, and Rachel maintains her clinical practice because she loves patient care.
Their finances have been simplified, and they have a clear path forward. They no longer worry about making difficult decisions alone. When questions arise about taxes, estate planning, charitable giving, insurance, or investments, they know exactly who to call first.
And their ‘work optional’ lifestyle has become a strategic advantage. While traditional retirees face mandatory distributions, Rachel and Dan continue building their legacy on their own timeline.
They are living proof that ‘work optional’ can be more powerful than retirement as long as that kind of lifestyle aligns with your goals. They have the freedom to practice medicine for as long as they want, knowing their finances are optimized for their situation.
This case study is based on a real client situation with names and certain details changed to protect privacy. Results may vary, and past performance is not indicative of future results.
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