Who We Work With

Financial planning works best when the advisor deeply understands the lives, careers, and financial realities of the people they serve.

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.

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

Medical Professionals in the Chicago Area

Many of our clients work in healthcare around the Chicago area. That includes people working at hospitals and medical 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 variable income and bonuses to planning around taxes, benefits, and retirement accounts.

We frequently work with professionals such as:

  • Nurse practitioners

  • Dentists

  • Orthodontists

  • Anesthesiologists

  • 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.

Medical professionals often face unique financial circumstances:

  • Irregular schedules

  • Changing compensation structures

  • Bonuses or partnership opportunities

  • High tax exposure

  • Limited time to manage investments or planning

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

Many of our clients come to us during a very similar stage of life.

They 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:

  • A growing household with children

  • Student loans or other professional education debt

  • Increasing income but limited time to manage finances

  • Questions about taxes, investments, and long-term planning

  • Desire for a structured financial plan rather than reactive decisions

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

We also work with many clients who are nearing retirement.

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

For those planning to retire within the next two to five years, we help address key questions such as:

  • When can I realistically retire?

  • How do I transition from income to withdrawals?

  • What tax strategies should I implement before retirement?

  • How should my investments change as retirement approaches?

  • How can I protect the wealth I’ve built?

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, an introductory “fit” meeting is a great place to start.