Who We Work With

Financial planning for healthcare professionals who want greater clarity around taxes, benefits, debt, retirement, and the decisions that shape the life they are building.

At Outside The Box Financial Planning, most of our clients share similar professional paths and life stages. While every client’s situation is unique, we typically work with professionals who have demanding careers, growing families, and complex financial decisions ahead of them. Schedule an Introductory Fit Meeting

Below is a general portrait of the people we most often help.

Healthcare Professionals in the Chicago Area

Many of our clients work in healthcare around the Chicago area, however we do work remotely with clients in all 50 states. That includes people working at hospitals and healthcare systems like Advocate Health, Rush University Medical Center, Northwestern Medicine, and others throughout the region.

Healthcare careers are demanding and often come with unique financial challenges - from managing high income tax liability and student loans to planning around employee benefits, family planning, life and disability insurance.

We frequently work with professionals such as:

  • Nurse practitioners

  • Anesthesiologists

  • Resident Physicians

  • Dentists

  • Orthodontists

  • Physician assistants

  • Other healthcare specialists

These professionals spend years developing their expertise and building their careers. Our role is to help them build a financial strategy that supports the life they’re working so hard to create.

Healthcare professionals often face unique financial circumstances:

  • High tax exposure

  • Student loan debt

  • Growing family

  • High Stress, long hours, burnout

  • Disability risk

  • Lifestyle creep

Our planning approach is designed to simplify financial decisions so clients can focus on their careers, families, and personal lives while still making confident financial progress.

The Typical Client Profile

We most often work with healthcare professionals at two important stages of life: those building their careers and families, and those preparing to transition into retirement.

Career-building professionals are often in their mid-30s to early 40s, focused on balancing professional growth with family responsibilities and long-term financial goals.

Common situations we see include:

  • Organize cash flow

  • Student loan debt

  • Employee benefits

  • Tax strategy

  • Insurance

  • Investments

  • Family goals and income and responsibilities grow

For many healthcare professionals, income is strong but the financial path forward is still unclear. Our goal is to help bring clarity and structure to that process.

Pre-Retirees and Those Approaching Retirement

Another type are in their mid 60’s (2-5 years from target retirement), focused on positioning their assets to provide the level of retirement income they are accustomed to.

Many healthcare professionals spend decades focused on their careers and only begin thinking seriously about retirement in the last few years before leaving practice.

We help address key questions such as:

  • Evaluate retirement readiness

  • Build a tax-efficient income plan

  • Coordinate investments and benefits,

  • Social Security timing and claiming strategies

  • Make informed decisions before leaving practice

This stage often requires careful planning and coordination to ensure the transition into retirement is smooth and sustainable.

Our Service

Healthcare professionals frequently relocate or change employers as their careers evolve.

Because of this, many of our clients value the flexibility of working with a financial planner who can support them regardless of location.

While we work with many clients in the Chicago area, our planning process can also be conducted virtually, allowing clients to maintain continuity in their financial strategy even if their career takes them to a new city or state.

Next Step

At the end of the day, the people we work with are often looking for the same thing.

They want to feel confident about where they’re going financially.

Not because they love spreadsheets or investment charts, but because money touches so many parts of life - family, career choices, retirement, and long-term security.

Financial planning, when done well, is less about complicated strategies and more about helping people make thoughtful decisions about the life they’re building

If that sounds like the kind of support you're looking for, Schedule an Introductory Fit Meeting, a 30-minute conversation to determine whether our planning approach is a good fit for your needs. Available virtually for clients wherever they live, subject to applicable jurisdiction requirements.