My 2016 Calendar

  1. My 2016 calendar starts in November 2015
  2. The calendar is heavy at the beginning and then becomes really light

November 2015

  • Watch what I buy because next month I am going to perform tax loss harvesting – wash sales rules limit tax deduction if you buy substantially identical stock 30 days BEFORE or after the loss sale (See chapter 4 of IRS Publication 550)
  • Assemble a tax lots inventory to plan tax loss harvesting
    • If not enough losses, then buy 2 options that benefit from opposite market movements
  • Decide on benefits enrollment (currently using a high deductible plan with HSA)

December 2015

  • Perform tax loss harvesting (sell capital losses of $3,000)
  • Convert after-tax thrift portion of my 401k plan to my Roth IRA (in-service withdrawals)
    • Contributions transfer tax free, pay taxes on the gains portion today to enjoy tax-free withdrawal at retirement
  • Send a ‘Penalty Abatement Letter‘ to the State that incorrectly charged me a penalty

January 2016

  • Send after-tax thrift 401k contribution check to 401k plan administrator
    • Contribution amount = $53,000 IRS limit allowed by my employer plan – $18,000 contribution to the 401k – company match expected
    • If I do not have cash, I will borrow on margin
  • Check with mortgage bank if I can pay taxes directly to the county rather than via escrow
    • Idle cash problem, losing a few hundred dollars every year
  • Contribute $3,350 by check to the bank where I have my HSA Account and not wait for payroll deductions in 24 installments (If you try to replicate this strategy, then please remember to get the IRS form 5498-SA from the bank, these outside the payroll contributions will not be reported on the W-2

February 2016

  • Pre-tax 401k contribution of $18,000 should be completed
  • Issue 1099 to a contractor (for my small business) – last date Feb 28th
  • Back door entry to the Roth IRA
    Current traditional IRA balance is zero.

    • Contribute $5,500 to traditional IRA (non-deductible)
    • Do a Roth conversion of the entire traditional IRA

March 2016

  • Install geothermal pump to get 30% tax credit (and lower electricity bill every month)
  • Convert after-tax thrift portion of my 401k plan to my Roth IRA (in-service withdrawals)

April 2016

  • File taxes
  • Adjust W-4
    • If IRS owes me money, then decrease the W-4 withholding
    • If I owe more than $1,000 to the IRS, then increase the W-4 withholding

June 2016

  • Convert after-tax thrift portion of my 401k plan to my Roth IRA (in-service withdrawals)

September 2016

  • Convert after-tax thrift portion of my 401k plan to my Roth IRA (in-service withdrawals)

November 2016

  • Watch what I buy because next month I am going to perform tax loss harvesting – wash sales rules limit tax deduction if you buy substantially identical stock 30 days BEFORE or after the loss sale (See chapter 4 of IRS Publication 550)
  • Convert after-tax thrift portion of my 401k plan to my Roth IRA (in-service withdrawals)
  • Decide on benefits enrollment

December 2016

  • Tax loss harvesting (sell capital losses of $3,000)
  • Convert after-tax thrift portion of my 401k plan to my Roth IRA (in-service withdrawals)
    • Contributions transfer tax free, pay taxes on the gains portion today to enjoy tax-free withdrawal at retirement

General themes, timing dependent on external events:

  1. If the stock market crashes, do one or more of the following
    1. Convert Gold/ commodities holdings into Equities
    2. I will convert a little of my large cap holdings to small
    3. Buy more on margin
  2. Try to reduce the assets I hold internationally, getting tired of FBAR requirements
  3. Further analyze if foreign ETFs are really necessary in my portfolio? Isn’t S&P 500 companies business exposure to ‘rest of the world’ not enough? A quick Google search says 30 – 50% of the revenue comes from international divisions.
  4. I would also like to get rid of the EWL (ETF that covers 85% of the Switzerland stock market). I bought it after I visited Switzerland for a week but now I think:
    1. The fund does not really add anymore diversification than I already have (I hold DBEF – my favorite foreign large blend ETF)
    2. Although 85% of the country sounds like a lot, the fund actually holds less than 40 company stocks, so there is a high company-risk
    3. The expense ratio of 0.48% is high