What are my risks of early assignment?
One reason this happens is due to dividends. If the dividend amount is greater than the time value left on a call, it can make sense to exercise early to collect the dividend.  Deep in the money puts also may get exercised early. There's usually little premium on a deep in the money put and the spread on the bid-ask might erase what little premium there is. If you have stock worth $5,000 but own puts on them that will give you $50,000 upon exercise (and no spread to worry about), the interest you can gain on the $50k might be more than the little to no time value left on the position... even at several weeks to expiration. The put vs call assignment risk, is actually the reverse: in-the-money calls are more likely to be exercised early than puts. Exercising a call locks in profit for the option holder because they can buy the shares at below market price, and immediately sell them at the higher market price. If there are dividends due, the risk is even higher. By contrast, exercising an in-the-money put locks in a loss for the holder, so it's less common.
Go the opposite approach.  Budget a certain amount of cash and keep it combined.  Don't exceed it (but next time budget more if you need to).   If you were in the USA (where card acceptance is near universal) what I do is simply use my visa check card for all purchases and download it to my personal finance software, where you can assign categories. Frequently people saving money for a down payment, or for their emergency fund, feel that they need to find a way to speedup the process via methods that will generate more interest than a bank account or a CD. Once they have reached their goal they also feel that having the money sitting around not generating income is a missed opportunity. All investments that aren't 100% safe introduce risk. To entice you to invest they offer the opportunity make more money than a bank account or CD. But the downside is that the extra money isn't guaranteed. In fact the introduced risk also opens up the investment to the possibility of losses, including a total loss. You have identified risks with bank accounts and CDs. With the bank account you will generally lose money vs. inflation. With a CD the investment is less liquid if you sell early, or you want/need to sell 1/2 a CD, you will give up some of that extra income. Also if rates on a CD rise next month you are stilled locked into your current rate til the CD ends. Putting some or all of the money you are saving for the house into a risky investment means that you may shorten or extend the time period. Nobody knows.  by investing in real estate we can offset the risk of real estate   going up in the next couple years: if real estate goes up we will   still be able to use our down payment for a comparable house as of   now. Inversely, if real estate goes down we will lose on the down   payment but be able to get a house cheaper. Unless the REIT matches the market of residential real estate in your city/metropolitan region there is no guarantee that home prices in your city will move the same way the REIT does.  A recent listing of the 10 largest holdings of the index is: none of these tell me what home prices in my neighborhood will do next year. "I did this 20 years ago. I wanted desperately to quit my job, but my wife wouldn't let me -- not because she thought it would fail, but just because she thought it would take longer than I thought. It took us 2 or 3 years to get to roughly half my previous salary as a software engineer. It's been my full time job for 15 years now. It's much better to not have enough time to finish X, Y, or Z on your startup than to have finished it and be waiting for someone to show up and pay. I agree with ""Don't quit your day job until you are very confident your startup can support you and is making money"". Validate your startup idea early. In the words of the Lean Startup movement, ""Fail Early"".  This is absolutely critical. Starting a company requires extreme confidence. Succeeding requires extreme humility and a willingness to face your mistakes (because how else can you improve?). You've clearly got the confidence. Now you need to to be realistic and look at ""What could go wrong?"" and ""How will I know that this is working?"" There are some parts of a startup that require what I call ""Calendar Time"". It's just elapsed time for things like: You tweaked your landing page and you're A/B testing whether that improves things.  And you wait for a week or two. You are waiting for a contractor to finish something on your website's Payment feature.  Read The Lean Startup (and similar books) to get an idea of all the things you'll need to do.  You'll need to:" This depends on a combination of factors: What are you charged (call it margin interest) to hold the position? How does this reduce your buying power and what are the opportunity costs? What are the transaction costs alternative ways to close the position? What are your risks (exposure while legging out) for alternative ways to close? Finally, where is the asset closing relative to the strike? Generally, If asset price is below the put strike then the call expires worthless and you need to exercise the put. If asset is above the call strike then put expires worthless and you'll likely get assigned.  Given this framework:  If margin interest is eating up your profit faster than you're earning theta (a convenient way to represent the time value) then you have some urgency and you need to exit that position before expiry. I would not exit the stock until the call is covered. Keep minimal risk at all times. If you are limited by the position's impact on your buying power and probable value of available opportunities is greater than the time decay you're earning then once again, you have some urgency about closing instead of unwinding at expiry. Same as above. Cover that call, before you ditch your hedge in the long stock. Playing the tradeoff game of expiration/exercise cost against open market transactions is tough. You need sub-penny commissions on stock (and I would say a lot of leverage) and most importantly you need options charges much lower than IB to make that kind of trading work. IB is the cheapest in the retail brokerage game, but those commissions aren't even close to what the traders are getting who are more than likely on the other side of your options trades. Well it depends what you are trying to do. You first job, almost by definition, will be entry level. Your coding is particularly valuable. The basics probability distributions should take you like a day or two tops with your background. So, no, I don't think some sort of job in risk management or a small role in a quantitative finance group (likely just coding) it out of the question. Only one way to find out. And you'll pick up the rest from there.  Edit: Just read you have a graduate degree in Physics/Math/Engineering. Of course you could get a job with your skill set. Likely a good one. One of the upsides to finance is they like to hire smart people and are okay with them developing skill sets as they go. "I once was reviewing one of those contracts with plenty of bad clauses in it, sitting across from the salesman whose commission depending on me signing it.  I started crossing out all the bad clauses, initialed them and said I would sign it if he'd initial the changes as well.  Oh, and there was one clause that said something like ""THIS CONTRACT MAY NOT BE MODIFIED WITHOUT THE EXPRESS WRITTEN CONSENT OF THE EXECUTIVE VICE PRESIDENT...""  Of course, I crossed it out as well.  I signed, he signed.  Everyone was happy.  Fortunately I never had to deal with any of the issues, but what's the worse they could do?" "Did a math undergrad, this is apparently super common in math/compsci departments , especially Adderal. I suspect the numbers are far lower than stated, however. They help you with mindless, repetitive tasks or cramming, but most of those kinds of drugs are just going to fry your brain, prevent you from thinking abstractly, and eventually turn you in to a zombie.  It's actually very frightening how non-chalant people are with (potentially dangerous) drug abuse. Taking care of your health; sleeping and eating well, will go a long way towards keeping you in peak condition without substance abuse. I get that in some fields (finance inclusive) the hours and workloads are almost fetishized amongst juniors, but personal health is just so much more important than trying to win the ""longest hours"" competition.  With all that said, I obviously don't take them, but do love coffee and probably drink a bit too much in a day." In addition to the other answers, consultants and contractors face a real risk (though admittedly small) of not getting paid. The more short-term the gigs are, the higher the risk of not getting paid for a particular job. As an employee, there are laws to ensure that you get your paycheck. As a contractor, you're just another creditor. I know a couple of contractors (software engineers) who have had difficulty collecting after a job. (I'm not even sure one ever got paid the full amount.) I also personally witnessed a contractor show up for a job who was then told by the company that they unilaterally decided that they would pay half of their pre-arranged rate.