Plans Which Can’t Fail

External events often have to be left to chance. You submit your book proposal, and maybe it gets accepted and maybe not. You go talk to the cute stranger, and maybe you’re compatible and maybe you’re not. You plan a camping trip a month ahead, and maybe it rains or maybe it doesn’t.

Often, though, people leave things to chance which don’t have to be. Will you finish your book? Will you learn how to code? Will you have a good group of friends? These are all things that are entirely within your own power, and yet you may not be sure if they’ll happen.

The value of ten half-finished projects is roughly zero. Not exactly zero, because hopefully you learned something, but close enough. The value of five fully finished projects is, well, a whole lot higher. Making plans is worth a little, working towards goals is worth a little, completing goals is worth a lot.

For that reason, I highly prioritize finishing.

I know that my natural approach to a project is to jump in without really thinking about it and to hope that it gets finished and does well. That’s why I have a huge folder from years ago that’s full of half finished books, coding projects, and who knows what else.

To combat that natural response, I now develop plans that can’t fail. By that I really mean plans that are extremely unlikely to fail, since a meteor strike can ruin just about any plan.

Maybe one of the most important things to me right now is my coaching program, because other people are counting on it. With only one hour per month per person, I need to make sure I’m always at my best.

The first thing I did was build an automated system to handle scheduling, reminders, and payment tracking. I realized that doing those things manually would cause errors and it would also demotivate me, so I eliminated them from the equation.

I also created a policy for myself that says that I can spend up to the amount the client is paying on getting a quiet and private space for the call. Usually that’s just my house, but I’ve also rented an Airbnb just to use for an hour, and have changed flights several times to make sure I won’t be late and will have time to prepare.

One of the reasons I built my own scheduling software was because no existing solutions had a lot of flexibility in making times available or unavailable. With mine I only open up hours where I know I can be at my best. I skip the first couple days of a big time zone change and avoid early or late hours of days where I’m not sure what my sleep schedule will be.

I also have certain procedures for taking notes during calls, reviewing those notes, and taking time to look for patterns between clients.

All of that doesn’t mean that I’m a perfect coach for everyone, or that everyone is in a financial position to get their money’s worth from it. But it does mean that I’m always able to deliver my best.

Contrast that to a more moderate approach where I handled scheduling by email, made calls from wherever I was, and didn’t analyze my schedule two months in advance. I’d probably get burnt out pretty quickly and would probably show up tired sometimes.

Instead I thought about everything that could go wrong and created a plan that couldn’t fail.

To take a totally different example, think about dating. Most people go through their dating lives totally haphazardly. I used to, but then realized that that was a plan that could fail.

So I signed up for three different dating sites, went on them every day, and went on dates with anyone I couldn’t “rule out”. Once I knew that they couldn’t be a long term match, I’d break up, even if I really liked them, because I knew that was taking time and attention away from people I could date. Most people won’t do that.

When I met my current girlfriend, I allowed myself to make her a top priority very early on. I spent all of my free time with her while she was in Vegas and then I flew to visit her in Texas ten days later. Since then I’ve made time any time she was available to travel to see me, and even went to China with her a couple weeks ago.

(Hopefully it goes without saying that you need to have a high level awareness to give someone that much attention and not have it be smothering or counter-productive)

While it’s possible things could fail with my current girlfriend (I hope not!), this approach virtually guarantees that I’ll end up in a happy relationship.

A final example is some of the real estate purchases I’ve made. So far I’ve bought an island, a flat in Budapest, and a chunk of a Vegas neighborhood with my good friends. Many people predicted that these things would be total disasters, but each has been literally completely conflict free.

Why is that? Because I designed each to be a plan that couldn’t fail. I specifically chose groups of people I knew would mesh well, despite the fact that it limited my pool and made it more likely I wouldn’t be able to buy a place. I kept the price low enough that I knew anyone could walk away from the money and not need it for something else. And last, I’ve dedicated huge amounts of personal time and priority to each of these things, to make sure that they are worth it for everyone.

People often see me as a risk-taker, but I like to say that I try to do the riskiest things in the safest way possible. I find things that people think are risky, and then I do the analysis to make them not so, or at least significantly less so.

How do you do this? Think about everything that could go wrong and brainstorm on each topic. Think outside the box. Dedicate way more time and focus to things than other people would, armed with the knowledge that a successful finish is much more valuable than a bunch of half-cocked attempts at different projects. Pare down your ambitions to projects for which you know you can develop a no-fail plan AND which you can build on later.


Check out that amazing ball pit I saw in China!! I really wanted to go and play in it. Oddly it was in the middle of “tea city”, which is a giant outdoor mall that has almost entirely tea stores. In other words, heaven for me.

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