Financial coach · Chicago, IL

41.8781° N / 87.6298° W

You can’t navigate water you haven’t measured.

Money Clarity with Rob is a financial coaching practice in Chicago. Budgeting sessions, debt payoff plans, investment basics, workshops and one-on-one coaching — and every engagement starts the same way. Measure first, then move.

Band 01 · Shallows · 0 – 6 m

The shallows

Where the money comes in.

Every budget starts at the surface. A budgeting session maps what arrives each month and what leaves it — income, fixed costs, the small recurring charges nobody counts — until a normal month is something you can read rather than guess at.

  1. 01

    The full inventory

    Every account and every recurring charge in one list, with what actually moves through each one.

    1.2 m
  2. 02

    One page, one month

    Income and fixed costs side by side, so the shape of a typical month stops being a mystery.

    3.0 m
  3. 03

    Your working depth

    A single figure for what’s left after the essentials — the number every later decision steers by.

    5.4 m
A laptop open to a plain spreadsheet on a kitchen table beside a handwritten notebook and a mug
Fig. 02 — A surface reading, taken at the kitchen table.

Band 02 · The Drop · 6 – 20 m

The drop

What you owe.

Paper statements and a calculator on a dining table in the evening, one hand sorting pages
Fig. 03 — Statements, sorted by hand, before anything gets paid.

Below the surface the pressure changes. Debt has an order and a rate, and a payoff plan is simply the shortest honest line between the balance you have and the balance you don’t.

  1. 01

    Inventory

    Balances, rates, minimums and due dates, written down without rounding and without optimism.

    7.8 m
  2. 02

    Order

    We choose what gets paid first — the highest rate, or the smallest balance — and we choose it for a reason that fits you.

    12.5 m
  3. 03

    Rate of descent

    A monthly figure you can actually hold, and a date to aim at. Adjusted whenever life adjusts.

    18.9 m

Band 03 · Deeper Water · 20 – 45 m

Deeper water

Before we talk about investing, let’s find the bottom.

Investment basics come last for a reason. Once the shallows and the drop are charted, we cover what the accounts are, how they behave when the water moves, what they cost to hold, and what a long horizon actually asks of you. The point is not to pick anything. The point is to know the shape of the thing you’re standing on.

This is where most people start, and it’s usually the worst place to begin. Depth first. Decisions after.

Lake Michigan seen from the Chicago shore at dusk, with the skyline hazy and distant
Fig. 04 — Chicago’s water, read from the surface.

Band 04 · Guided Dives · 45 – 70 m

Guided dives

Workshops and one-on-one coaching — each with a line back to the surface.

Marker 01 · 52 m

Workshops

A group descent on a fixed line. Sessions run on a set date at a set depth — budgeting, debt, or investment basics — and everyone comes back up with the same written plan in hand.

  • Held in Chicago
  • Fixed date and depth
  • A written plan to take home
A small workshop session around a table in a Chicago meeting room
Fig. 05 — A guided dive, down together.

Marker 02 · 68 m

One-on-one coaching

A private dive, paced to your own depth. Ongoing sessions that pick up exactly where the last sounding left off, at an interval you can keep.

  • Private and paced to you
  • Ongoing, not one-off
  • Your own line to the surface
A one-on-one coaching session at a table by a bright window
Fig. 06 — One line down, one person.

Band 05 · Final Sounding · 70 m +

Take the last sounding.

A free consultation. Tell me where the water is, and we’ll find the bottom together.

Whether you need a budgeting session, a debt payoff plan, investment basics, a workshop or one-on-one coaching, the first step is the same: a conversation and a measurement. No script, no pressure — just an honest reading of where you are.

Bring the numbers you have. Rough is fine. Rough is usually where the real depth shows up.

Free · Chicago, IL
One conversation, then a plan.