Tax Planning 2018 and Beyond

Important points and dates below for any year-end planning items. Please do email if you have any questions. Be sure to see both the Individual and Business sections.

Of course this is not comprehensive, nor tax advice, but rather educational and I highly recommend contacting Gillingham CPA. Also please use an attorney and financial planner to fill-in what can be your very own miniature family office, even if it is just you on the tax return. I refer to family office as a loose advisory team to assist in your ongoing tax, accounting, legal, investment, insurance, and other matters. We are grateful to be a part of this picture.

  1. Healthcare (tell a friend!)

Covered California / Medical / Other

  • Open Enrollment begins October 15, 2018and ends January 15, 2019.
  • To start coverage by January 1, 2019, apply by December 15, 2018
  • Generally “Covered-CA” is a good place to start and if in a very low income year can consider MediCal or alternative options may exist depending on your state

Individual Planning – Dec 31 time sensitive

  1. Any planned stock option exercises
  2. Healthcare, workplace enrollments, using 401K, dependent care benefits
  3. Stock sales for any gains or losses
  4. Moving away from our beautiful, yet, high-tax state (California)
  5. Donation of cash, non-cash, and appreciated stock
  6. Planned gifting and establishing educational accounts
  7. Income acceleration or reduction strategies for major outlier income years
  8. Use of any “use it or lose it funds” such as medical-type savings plans (flexible spending)
  9. Do Required Minimum Distributions if required as IRA owner or inherited IRA beneficiary

Individual Planning – April 15 time sensitive and setting up for success

  1. Ready for any Q 4 payment, Jan 15 or April 15 tax due
  2. Planning for IRA contributions or back-door IRA strategies
  3. S.A funding
  4. Planning to quit job or major life changes
  5. Ready to report any foreign accounts and trusts
  6. Any foreign taxation well-planned for
  7. Ready with any crypto-currency gains / loss reporting
  8. Ready for stock option vesting dates, especially year 1 cliff
  9. Generally working with financial planner to ensure household finances are in line, trusts and related household legal matters (power of attorney etc…) are in place, have adequate insurance and account titles are properly assigned (extreme caution with retirement accounts)
  10. Any tax credits well planned for in relationship to solar, electric cars, etc…
  11. Having well-titled PDF scanned tax documents ready, engagement letters signed
  12. Document and total out of state tax-free purchases… as California wants to tax this

Business Planning – Dec 31 time sensitive

  2. Solo 401K, retirement, defined benefit planning
  3. Getting books and records in shape for planning and the year-end close
  4. Accelerated any cash-basis deductions for higher income years
  5. Planning any income strategies
  6. Establishing automatic record keeping with Quickbooks online optimization and automatic PDF statement download from services such as Hubdoc
  7. Entity closing or entity establishing before or after year-end as is appropriate
  8. New bank accounts or closing old as needed
  9. Setting up
  10. Obtain W-9s (request for taxpayer ID) for contractors and make sure any other contractor related legal documents are signed

Business Planning – time sensitive and setting up for success

  1. Jan 31, issue those 1099s as needed! seems to work pretty fine
  2. Deadlines… file extensions ASAP, typically before March 15 and setup for success to get filed long before other due dates… as penalties are NASTY and pointless, especially with S-Corps and LLCs (multi-member)
  3. Pay your taxes
  4. Consult attorney if employing any equity comp plans
  5. Plan for any retirement funding
  6. Optimize accounting, reconcile books, get useful books, establish semi-automated accounting
  7. Automate receipt gathering
  8. Strongly consider business credits such as for Research and Development
  9. Make sure San Francisco and other city taxes and registrations are in order
  10. Ready for all and any ongoing city property, payroll, gross receipts and “other” taxes
  11. Ensure other state registration and tax in order (Delaware often)
  12. Sales tax monthly or other interval compliance

Questions? Please see the new client contact button.

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