Questions to ask yourself when checking in on your finances

Financial planning is a Socratic process of discovery. Below is a non-exhaustive list of questions we ask our clients and suggest you ask of yourself:

Financial Planning

  • How have my cash flows changed?
  • If I’m drawing income from portfolio assets, what is the optimal withdrawal strategy in response to volatility?
  • If working, what is the likelihood of cashflow disruption and how long can core expenses be covered w/o income?
  • What are my core expenses?
  • Am I adequately insured?
  • As a business owner, am I aware of and optimizing leverage, retirement accounts, tax credits, loss carry backs…?
  • If I am compensated with employer stock, what is my liquidation and diversification strategy?
  • Am I properly diversified?
  • How do I know?
  • What level lifestyle do I want to finance in the future and when?
  • Do I actively rebalance in accordance with my pre-defined investment policy?
  • Am I taking advantage of volatility and actively tax-loss harvesting throughout the year to optimize my taxation?
  • If I had a loan secured against my portfolio, in the event of a market hiccup, what is my plan to avoid a margin call forcing me to sell assets at depressed prices? Does my advisor and banker have a plan for that?
  • Am I supporting another family member or friend?

Estate Planning

  • Is my estate plan in order?
  • Do I have a physician’s directive, medical power of attorney, a durable power of attorney, HIPAA Release, a Will, and any other documents necessary to carry out my wishes?
  • Where are these documents located and who needs to know their location?
  • Can they readily access these documents?
  • Who will have the legal authority to make decisions on my behalf if I am unable to make them?
  • Have I talked with my beneficiaries and fiduciaries so that everyone is on the same page?
  • Have I confirmed accuracy of my beneficiary designations on insurance policies and retirement accounts?
  • What does my bank and other financial services institutions require to ensure a loved one can access to my accounts?
  • Do I use a password protector, and have I shared username and password(s) w/a trusted person(s)?

Health Emergency Planning

  • What will I do if I have a sudden and serious health emergency?
  • What will I do if a family member has a sudden and serious health emergency?
  • Am I sufficiently insured in the event of disability? How do I know?
  • What are the terms of that coverage; how long will I have to be disabled and at what level before benefits begin?
  • What are my healthcare deductibles and do I have a sufficient cash reserve to cover them?
  • Am I funding a Health Savings Account in addition to other savings vehicles?
  • Which hospital would I want to go to?
  • Do I have a primary care physician who is affiliated with my preferred hospital system?

An advisor’s role is more than picking investments. We partner with you on everything in your financial life, from the 101 stuff to the 401 stuff: organization, budgeting and cash flow management, estate planning, debt service planning, retirement plan services for your firm, tax optimization, confirming beneficiary designations, confirming adequacy of all insurance policies and risk management strategies, ensuring employer offerings are maximized, funding education, ensuring that major purchases are made the right way and at the right time.

At Ackerman Capital Management, we take a holistic approach to wealth management. We operate as a partner with our clients and proactively organize their financial lives, plan for the future, and manage risks that may arise along the path.

For questions or comments reach out to me by email.

Keith A. Pillers, JD, CFP®, CIMA®, CPWA®
Director of Wealth Management



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