87 | The RwM Checklist

This checklist is designed to help us keep tabs on our relationship with money.

It is a useful tool to create a baseline understanding of our relationship with money and to refresh every few years to keep tabs on inevitable changes that will happen over our lifetime.

Relationship with Money

• I am able to filter out the noise and identify the most important decision or next step as it relates to my finances.
• I find it easy to trust the simplest explanation or strategy for getting something done.
• I am able to tell the story or describe the "whys" behind my financial decisions beyond the objective dollar amount spent or received.
• I am able to orient within a financial conversation or decision that has many variables and emotions.
• I am able to minimize second-guessing or regretting many of the financial decisions that I make.
• It feels natural to have conversations with other people about money.
• I am able to identify the financial goalposts that I am aiming for.
• I am able to see alternatives beyond "more" - more income, more spending, more saving, or more investment return - as ways to experience financial well being.

Sustainable Income

• My income is generated by leveraging my most natural gifts and skill sets.
• My income streams have a long or indefinite horizon.
• I am able to manage the risk of burnout that accompanies my means of generating income.
• I am able to spend time doing things that matter to me.
• I am able to spend time with people that matter to me.
• I find significant pleasure in the ways I generate income.

Content Spending

• I spend money on the people, experiences, and things that are most important to me.
• I spend money on the people, experiences, and things that bring lasting contentment.
• I am aware of how my spending has changed over the past few years.
• I am comfortable with how my own level of spending compares to my perception of the level of spending of family, friends, neighbors and colleagues.
• I am confident that I could adjust my spending in the face of uncertainty without undermining the things that matter most to me.
• I am able to be generous to the magnitude that I have always hoped or envisioned.
• I experience freedom and fulfillment as a result of my generosity.
• I am comfortable with the role that debt plays in my relationship with money.
• I do not feel like debt gets a “seat at the table” when I am making financial decisions.
• I can see how dollars I spend directly enhance the relationships of people that mean the most to me.

Accessible Saving

• When my income increases, it is easy for me to increase my rate of savings to match the increase in income.
• I am comfortable with how I decide to set aside dollars into short term and longer term buckets.
• My level of cash on hand feels like it allows me to manage the stress and increase the flexibility I feel in the month to month.
• My level of cash feels like it allows my other assets to remain untouched except for the times I intentionally access them.
• I see saving as a way to manage lifestyle creep and keep my expectations in check.
• I feel like I have a good grasp on how much financial wealth is enough for the life I desire to live.

Patient Investing

• I have a high level understanding of how my dollars are invested.
• I have a high level of conviction in the philosophy that I use to invest dollars.
• In the face of uncertainty or new information, I do not question the investment philosophy that I am using.
• I am comfortable knowing that in a world of 7 billion people, many people will experience better investment returns than I do.
• I am aware of the fact that my ability to remain invested during the most unsettling times is more important and more attainable than any technical investment tactic.
• I appreciate the fact that "owners" of businesses bear more risk, but can also reap more reward than non-owners or lenders to businesses.
• I appreciate the fact that "spreading your eggs across many baskets" might limit cumulative return potential, but also limits cumulative loss potential.
• I am comfortable with the reality that my investments might not ever experience positive returns, but often do in periods that exceed 5 or 10 years.
• Many people who know me well would call me a patient person.