Not too long ago, I was attending an investor mastermind meeting in Dallas, TX, where we broke up into roundtable groups of about six people. The moderator proceeded to ask us all a very thought-provoking question. He said, “What will you do if something drastic happens and you get hurt or became incapacitated, causing you not to be able to work at all (no internet or phone) for the next 60 days?” Want more articles like this? Create an account today to get BiggerPocket's best blog articles delivered to your inbox Sign up for free What Would You Do if You Couldn’t Work for Two Months? Right about now, you may be thinking that this is one of those scary financial planning questions or that it's something your life insurance agent (who's trying to make another sale) might ask you. You're probably right, but stay with me. This is actually a great question for any of us to think about. I remember the folks at my table all had completely different reactions. For me, I remembered back to when I was a painting contractor and my entire business revolved around me. Sure, I had my own business and felt like I was in control, but did I really have it all together? The answer was no. After a few years, at age 42, I severely hurt my back. I was fortunate that I had approximately 20 rentals at the time, which offset my earned income. Without that, things would have been devastating for me and my family (my wife and two kids). The other good news, besides the rentals, was that I already had a college degree and a real estate license. Or in other words, I had other marketable skills. But back to the question asked in Dallas. If I couldn’t work at all during that time, then what would have happened? Related: How to Use Real Estate to Retire MUCH More Comfortably Than Your 401K Would Allow I guess my wife could have potentially worked full time, and I know I had disability insurance, but it didn’t really kick in for another six months. I would’ve had to try and live off of my savings. In a perfect world, we would all have six months of liquid reserves to cover our expenses. But if that’s not possible, maybe the next best thing would be access to cash (for example, credit cards or lines of credit on properties). Today, things are very different. My note company was designed so that operations would not revolve around me. In fact, I travel quite a bit, and my team seems to run pretty well even when I’m away. The others at my table were all over the place. One couple was close to retirement and had been planning for a while, so they seemed pretty prepared. The other couple next to me wasn’t prepared at all. The husband was a dentist, and his practice revolved completely around him. Also, he didn’t have much of a plan B. Although he was a high income earner, he didn’t have any real passive income to speak of coming from his investments. What Would You Do if You Could Never Work Again? After the groups were done discussing what would happen if they couldn’t work for 60 days, the moderator proceeded to ask the follow-up question: “What would you do if you could never work again?” OK, now it was getting serious. For me, this question might even be scarier than if I was asked, “What would your heirs do if you were to check out?” Obviously, most of us don’t like to think of our own mortality, but often we don’t like to think of other scenarios, either — such as never being able to work again. If I had been in this situation back when I hurt my back, things could’ve gotten really dicey. Now I do have more safeguards in place. As for the folks at my table, the older couple was pretty much set, but the middle-age dentist and his wife were in trouble. He didn’t really have anything set up to replace his income, especially before retirement. So, what safeguards could you put in place if you don’t have any? Well, besides having reserves, it’s a good idea to have assets that throw off some cash flow or provide you with access to cash if you need it. Cash-flowing real estate and notes may be the best option. Although, depending on someone’s situation, they may need to be less active and invest more passively by hiring a property manager or a licensed mortgage servicer. Dividend paying stocks could throw off some revenue, and liquid bonds could provide access to some cash. Related: This Lesson From My Mastermind Group Completely Changed My Real Estate Business Obviously, disability insurance could help, with up to two-thirds of what you would normally gross. That being said, the longer you go before it kicks in, the cheaper the policy is. Another potential safety net is a permanent life insurance policy, as it may allow you to borrow out cash value tax-free anytime you need it. Of course, some retirement accounts will also allow you to take penalty-free withdrawals for certain medical expenses. The questions asked at my Investor Mastermind meeting, as well as some of the options mentioned above, may be helpful for any of us to consider as we look at our own financial situation and plan for the future. What Do You Have in Place? As my buddy Jeff Brown always says, “Everyone should only have one goal in life. Get as many cash flowing assets in place as soon as possible, and get as many of them tax-free or tax-deferred as possible (IRA accounts, insurance contracts, etc.), but especially before retirement.” So, what safeguards do you have in place? God forbid something life-changing were to happen to you, do you have a plan B or C? If so, what’s that look like? Let me know your thoughts with a comment!