Exercise XII – Planning to Engage

The past few months have demonstrated a competency in setting, adjusting, and achieving desirable goals in a month-to-month context, building to reach a longer term goal (getting a job). Now that a better job perhaps on the horizon, I’d like to repeat this process, with the next few months being oriented towards learning about, acquiring familiarity with, and eventually assuming responsibility for running the finances.

Step 1: Observation (Months 1-2)

Over the next two months, each time my partner interacts with one of the following, I’d like to be there to take notes and observe:

Checking and savings accounts
Credit cards and debt
Mortgage and property taxes
Insurance (health, auto, home, life)
Retirement and investments
Budgeting and recurring expenses
Taxes (filing, documentation, estimated payments)
Emergency fund or savings goals

I should record things like web addresses, passwords, and recurring task frequency. Its important to take note of how she organizes information and on what criteria she makes her decisions. Depending on frequency, perhaps a twice weekly check in would be appropriate.

Step 2: Partial Engagement / Assuming Responsibility (Months 2-4)

Following the information gathering phase, and starting with what seems to be the easiest task, I want to build confidence logging into and managing a single account. Initially with my partner being the observer, but with the goal of having a list of reminders and calendar events to avoid relying on feedback or memory alone.

By the end of this term (marked by the beginning of Fall), I want to be preparing to assume full responsibility for all financials, with the eventual goal of a complete month of all activity without needing to check in for feedback or ask for help.

Step 3: Assume Full Responsibility (Months 5-6)

Beginning sometime in the Fall, I want to take over fully, checking in monthly and eventually quarterly to confirm that things are going smoothly. After this has been established, I can begin to make changes to the existing system for managing accounts, passwords, receipts, etc.

How to do it
Visual dashboards (e.g., YNAB, Monarch Money, or spreadsheets)
Calendar reminders with labels for recurring tasks (e.g., bill due dates)
Simple password managers (e.g., Bitwarden, 1Password)
Automation (e.g., auto-payments, recurring transfers)
Establish a weekly financial check-in time (30 minutes max)
Use checklists for each financial task (monthly, quarterly, yearly)
Keep a shared “financial playbook” (a simple document listing what to do if something happens)
Talk openly about fears (e.g., fear of messing it up or being overwhelmed)
Agree on what success looks like (e.g., “bills paid on time”, “accounts reviewed monthly”, not “perfect investing”)
If burnout signs appear, slow the timeline
Ask for feedback from her, and be open about needing clarity or adjustments

What I should watch out for
Overwhelm or Shutdown
Cause: Too much information at once; unclear steps; fear of making a mistake.
Signs: Procrastination, withdrawal, irritability, freezing up when asked to take over something.
Solution: Break tasks into small steps, use checklists, and take breaks. Go at a sustainable pace and communicate clearly when something is confusing.

Black and White, All or Nothing Mindset
Cause: Dwelling on thoughts such as “I didn’t do this perfectly, therefore, I’ve failed”
Signs: Refusing to take over a task due to fear of doing it “wrong”
Solution: Frame tasks as learning experiences. Encourage experimentation and emphasize progress, not perfection.

Executive Dysfunction
Cause: Difficulty with task initiation or planning.
Signs: Forgetting due dates, not logging in, unintentionally skipping tasks.
Solution: Use external supports like alarms, visual calendars, and routines. Build a consistent time of day/week for finance tasks.

Things to set up and communicate clearly
Weekly Check-Ins
10-15 min check in to ask “What’s going well?” and “What’s stressful?”

Shared Reference Document
To keep track of responsibilities, information, and goals so both feel informed and respected.

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