Trading derivatives on the path to Financial Independence and Early Retirement

All parts of this series:

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Derivatives and FIRE (Financial Independence and Early Retirement) sound like two things that don’t mix. Like oil and water. Financial derivatives (options, futures, etc.) have the aura of opaque and highly risky investments. On the way to Financial Independence, most people are either oblivious to derivatives or avoid them like they carry communicable diseases. Probably derivatives are also traded in some smoke-filled backroom or an illegal gambling joint, right?

Let’s look at the myths vs. facts!

Myth: ordinary investors should never touch options

Truth: if you currently own stocks and/or corporate bonds you already own options, whether you realize it or not. Equity in a corporation is essentially a call option on the enterprise value (the sum of all the firm’s assets) with a strike price equal to the firm’s debt. The firm’s bonds are a risk-free bond with a short put option where the strike price again equals the debt face value. In other words, as a bondholder, you lose money if the value of the assets drops below the debt load and the firm declares bankruptcy.

Merton Model
The Merton Model: Equity and Debt are essentially options on the enterprise value

If you think that this is thought-provoking and brilliant, thanks, but unfortunately it’s not my invention. It’s called the Merton Model, named after Robert Merton, the famous finance researcher, professor and Economics Nobel Laureate.

Myth: Derivatives are too complicated for the average investor to understand

Truth: Some derivatives may be too complicated for the average retail investor to handle (e.g., Swaps, Swaptions). But options and futures are actually very easy to understand, trade and maintain. In fact, I would pose the following challenge:

If you liked playing with Legos and building blocks as a kid, you will enjoy trading futures and options in your portfolio!

In other words, if you liked constructing, taking apart and rebuilding things and then rebuilding them bigger and better, then futures and options are going to be very exciting in your portfolio. Here’s one example of how the Lego and building block analogy works:

Futures Investments like playing with Legos3
If you liked playing with legos and building blocks you’ll like trading futures!

Step 1: recognize that the equity index return, including price movements and dividend payments, has to yield the same return as an investment in futures contracts. Any difference in return prospects between them would be quickly arbitraged away.

Step 2: hence, the two building blocks that exactly replicate the equity index return are holding cash at the current prevailing overnight interest rate and a long equity index futures position. The expected return on that investment is the same as the equity index expected return.

Step 3: why would I want to hold a lot of money at currently 0.375% p.a.? Let’s replace the boring low-yield cash building block with something more exciting: higher-yielding bonds! This could be a government bond fund (e.g., iShares ticker IEF, 7-10Y Treasury bonds) with a slightly negative correlation to the equity exposure. Or corporate bonds with an even higher yield, though the diversification potential is also lower. We’re killing two birds with one stone; higher expected return and lower risk through diversification.

Side note: A great advantage of this method: You can mix in close to 100% bonds into the portfolio, without reducing the equity exposure. That’s much better than replacing a few % equity with bonds with hardly any diversification benefit, see our previous post The Great Bond Diversification Myth

Step 4: well, regular bonds are a bad idea in a taxable account. Let’s replace them with tax-efficient Municipal bonds, at a slightly lower pre-tax yield but higher post-tax yield. We also realize that the equity futures portion is taxed as 40% short-term gains and 60% long-term capital gains (regardless of holding period due to IRS Section 1256). To overcome this effect, let’s scale up the equity portion by a factor of about 1/(1-tax rate). Or maybe even a little bit more because our bond portfolio diversifies our equity risk.

Step 5: the after-tax return of the whole thing should now be higher than even the before-tax return of the regular equity investment. All the while, volatility is contained due to the negative stock-bond correlation and the whole construct has a correlation with our other equity holdings of less than 1.0.

If I can do this with my daughter’s Legos I can do this in a portfolio! So, dealing with derivatives is not all that complicated, conceptually. Trading futures in practice is just like trading equities and ETFs, with limit orders, market orders, etc. The one difference is that futures contracts have an expiration date and once that date approaches one would have to sell the current contract and replace it with a later-dated contract, a process known as “rolling the contract.”

Myth: derivatives are risky

Truth: they can be, but they don’t have to be. Quite the opposite, a very popular strategy implemented through options is the so-called “covered call” strategy. You own the underlying stock and sell a call option, thereby selling the upside potential of the stock you own. Thus, you will experience lower risk than holding the underlying stock only:

Covered Call Option
Covered Call Option Payoff: Less risky than holding equity only!

A lot of academic research has pointed out the superior risk-adjusted performance of strategies with this style, see a piece by Ibbotson. That paper was written in 2004, but results are updated to 2012 in this piece by CBOE, so this approach worked also during the Global Financial Crisis. The covered call writing and put writing indexes all had comparable average returns vis-a-vis the S&P500 but a significantly lower risk level (10%-12.5% vs. 15% in the SP&500).

By all subjective and objective criteria we can think of the covered-call strategy is less risky than the direct equity index investment!

Why is this strategy, selling the upside, uniquely suited for the Early Retirement crowd? If you have already achieved Financial Independence, you no longer need to throw financial “Hail Mary passes” or shoot the moon, or win the lottery, whatever you want to call it. You have already saved enough for a comfortable life and all you need in terms of upside potential is the inflation rate plus withdrawal rate plus maybe a few more percent cushion to make up for occasional losses.

Again, to use our Lego analogy, we can split the equity volatility into upside and downside risk and sell off, for a nice premium, of course, the portion that we don’t need very urgently right now. So, wouldn’t you be willing to give up some of the upside in exchange for a relatively stable cash flow of option premiums? A yield that can easily surpass the dividend yield in your average equity portfolio? I would! And I can do that very easily and cheaply with options. There are some companies that will do this for you (Wisdom Tree has an ETF, ticker PUTW) but they charge you 0.38% for something you can do yourself for a fraction of the fees.

A lot of personal finance bloggers, e.g. Amber Tree Leaves, Investment HuntingThe Retirement Manifesto, and many others, implement the covered call writing strategy on individual stocks. Yours truly, Mr. ERN, implements this with options on index futures (more details in our post on option writing). And, you guessed it, the advantage of implementing this with futures is that we can use the same building block methodology as above: Hold the margin cash in (tax-free) Muni bonds, implement the option strategy on margin, scale it up to a comfortable after-tax risk level and enjoy! More details here.

Myth: derivatives are expensive to trade

Truth: it’s partially true. I would never trade futures contracts at a regular brokerage firm, like Fidelity. The fees are too high. But some brokers specialize in derivatives trading, for example, Interactive Brokers, which is the firm we use. The trading and maintenance of a simple long equity futures contract is in the low single basis point range (~0.02-0.03% p.a.), which is even slightly cheaper than the lowest cost equity index ETFs.

Myth: derivatives are opaque and unregulated

Truth: most derivatives are trading on highly reputable exchanges and are regulated to ensure integrity and investor protection. In the U.S., options trade on the CBOE, and futures and options on futures trade on the various exchanges belonging to the CME group. The CFTC (Commodity Futures Trading Commission), the SEC (Securities Exchange Commission) and a few other authorities (public and industry) keep everybody honest.

Some options are indeed unregulated and there’s potential for fraud and abuse. The SEC has recently issued a fraud alert (as well this warning) on binary options. We personally stay away from binary options because they seem too much like a pure gamble.

More information

  • Option education podcasts (via The Options Industry Council). I checked out some of the option education videos and they are pretty good!
  • Whaley: Derivatives (paid link) – Book on everything derivatives. Includes an Excel add-in with option pricing formulas. Geez, that book is expensive now. I think I paid only ~$80 many years ago.
  • National Futures Association: Education on everything Futures related.


  • Everybody who owns stocks and corporate bonds already has option exposure of sorts.
  • Options and futures are a great way to fine-tune the FIRE portfolio and increase exposure where desired or sell off the upside potential for guaranteed extra yield (covered call strategy). After getting over my initial fear of derivatives, I’ve been very happy with my recent performance.
  • If you are trading with a reputable brokerage you should be safe from fraud, but still, educate yourself before investing. Even with perfectly legitimate brokers, you could still legitimately lose a lot of money. Never use excess leverage. A little bit of carefully measured leverage is OK, see our previous posts Lower risk through leverage and How to create a no-limit Synthetic Roth IRA in a taxable account.

Have you traded derivatives? If not, have we at least sparked your interest? Please share your thoughts below!

43 thoughts on “Trading derivatives on the path to Financial Independence and Early Retirement

  1. Nice!

    I’ve been trading futures since 2011. I love the ability to diversify; to get in and out at virtually any time of day; to take advantage of the 60/40 tax treatment and to offset previous years gains with current year losses (if any).

    For me, the biggest advantage of futures is the liquidity – the ability to get in and out without moving the markets and the ability to get out over night godforbid something crazy happens in the markets or in my personal life. I like the flexibility of not having to wait until the next morning to exit investments and take money out of the markets.

    1. Hi Mike!
      Thanks for stopping by again! Yeah, liquidity is king. Also for me the easy leverage, the 60/40 tax treatment and the ease of tax preparation (no need to itemize transactions) is a great advantage. I do about 1,000 trades per year and all I have to do is fill in one single number on IRS form 6781.

  2. A really nice job here as always, ERN. You really do some good work.

    I like your explanations here and think this piece adds something valuable in terms of tractability. Derivatives, options, etc. can seem overwhelming. I also like your admonitions against excess leveraging. Which is probably the area most people are likely to get into trouble with stuff like this.

    Good work, and many thanks for the interesting read!

    1. Thanks FL! Yes, absolutely, be careful with the leverage. It’s like a super hot habanero sauce: to be used in small doses to make everything taste much better, but deadly in big doses!

      1. Ha! That’s such a great analogy!

        Speaking of hot sauce, have you ever tried any of that ghost pepper stuff? It’s pretty much a certain ER visit, and maybe intensive care if you’re not careful. Woo!

        Have a good Labor Day, ERN.

        1. Thanks!
          Oh, my, I have to be really careful with the hot sauce. If it’s an ER visit for the hot sauce expert, it might be the morgue for me. I will make sure if I see a sauce called “ghost pepper” I will consume a mostly homeopathic dose. 🙂
          Have a great Labor Day weekend too!

  3. Nice post ERN. Count me in the list of folks too scared to trade derivatives, but your post has intrigued me to learn more. Is there a primer you recommend or any e-books you can email me so I can read to understand this area more? Thanks.

    1. I liked the podcasts here:

      For example on selling puts:

      Covered Call Writing:

      Basic option pricing:

      Interactive Brokers has some webinar recordings about how to actually trade options on their platform:
      (look for “TWS OptionTrader”)
      But that might not be so helpful if you’re using a different broker. But every broker should have their own material on how to trade options, what the different strategies are (for us FIRE crowd it would be mostly “Covered Call Writing” or “Put Writing” or “Income Strategies”).

      For example at Fidelity:

      Best of luck!

  4. Ah derivatives. I remember putting in $500 to play a stock’s earnings and the value jumped to $1200 in about a day. I stopped trading and playing earnings however because the upside compared to the risk really isn’t worth it. It’s almost like heads you increase the value in double digits (rarely triple digits) but tails I lose 100%, basically. I also don’t understand derivatives that well enough to play it, that will be for another time!

    1. That’s the curse of buying calls: You could lose 100% if the price stays below the strike. Hence, I like to do the opposite. Sell the upside and collect a premium.
      Selling options is a way to benefit from two types of traders who are destined to under-perform the market: The gamblers who look to make the +300% trades (they are buying calls) or the extreme risk averse investors who want to buy puts for protection. Both are paying very high premiums for those options and I’m on the other side making money off them. 🙂

  5. As someone who is thinking about getting into trading derivatives, this is a great post for me to read. Thank you!

    Gotta love the duplo graph. 😀

    1. Thanks! Yes, this might be interesting for the dividend experts like yourself. Lots of investors milk their dividend stocks for extra yield by selling covered calls!
      Glad you liked the Duplo/Lego picture! 🙂

  6. Hi Big Ern,

    Congrats on the ER yesterday! Will you be writing a detailed post on how you personally use covered calls like you did on selling puts? I would love to learn more about how you approach this. The CBOE call write indexes seem to under-perform PUT so I am wondering how much of your account you use for writing calls?


    1. Thanks!
      I like the put writing strategy more than call writing because out of the money puts have a richer premium. Covered calls with the SAME strike should – in theory – yield the same results (Put-call-parity), but deeply in the money calls have not much liquidity (wide bid-ask spread), so I don’t do those. Covered calls with strikes at-the-money or out of the money have too much delta (equity beta) for my taste (at least at inception), so I don’t do those. 🙂

  7. Karsten, My usual vanilla index ETF strategy is country agnostic in that I try to emulate a market cap weighted allocation to both US Total Markets and All-World Ex-US.

    Is there a way to replicate an “agnostic” version of this either through futures (lego technique), or short put strategy?

    The best I can see are these two futures which in a 9:1 ratio would effectively be all world:

    1) MXWO MSCI World Index

    2) MXEF MSCI Emerging Markets

    I’m not sure how liquid or cheaply traded these are. Perhaps that is what prevents this method from working?

    Also the account size would have to be too large so I would likely start off with no emerging markets is this method is even feasible.

    I also don’t think future options exist for these so it would have to just be rolling long futures.

    So far my agnostic approach is dragging on my portfolio because All-World Ex-Us is performing poorly compared to just US but I feel better knowing that I’m not making an “active” choice. Perhaps this is also wrong?

    Perhaps just the short put strategy on ES is easiest.

  8. Please ignore. I’m not sure how to subscribe to the comments besides making a comment so that’s what I’m doing.

  9. I’ve been re-reading this to educate myself more as I dip my toe into the water here. Fortunately Fidelity is now in line on cost and I can sell small contracts without the commissions killing the strategy.

      1. Those quantities are far above my approved option authority….but will look.

        I’m confident their margin cash requirements are much worse than IB

  10. Hello ERN,
    If you could please elaborate on “recognize that the equity index return, including price movements and dividend payments, has to yield the same return as an investment in futures contracts”, a statement that you made in this article above. I do enjoy playing with Legos, yet that statement of yours and the image above of the Legos left me in the dust. Everything else you discuss, I am understanding. I’m new at all of this, and your wonderful website and your generous information is now integral to my ongoing research. I would really like to understand what you mean by this quoted statement here of yours. Thank you.

    1. Haha, that’s a good question!
      It’s a no-arbitrage constraint that the investment in the physical asset has to yield the same as the futures investment. If not, large hedge funds and endowments could generate risk-free extra return.
      In fact, the no-arb constraint is so strong, some of the high-frequency trading hedge funds built their own fiber network to connect the NYSE (New York) and the CME (Chicago) platforms to arbitrage price movements just a millisecond faster than everybody else.

  11. Great post!

    I can invest my margin (collateral for futures) only in futures (no ETFs, mutual funds, etc), due to my employer’s compliance policies. Any idea how I could invest my margin for a low-risk, low yield return?

    I know my question is not exactly related to the selling-puts strategy, but it’s related regarding the margin aspect.

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