If you have big dreams and big goals (and if you don’t, why not?) then you are going to need big magical projects to reach them. Now, the whole premise of this site is that combining Project Management (PM) with Practical Magic (PM) can improve your life in major ways. But it’s not always easy to do and sometimes we are our own worst enemies.

Long ago, when this blog first started, I wrote a post about the process groups. These are the critical phases of a large project — right out of classic project management. Whether or not you are running a classical project or an agile one (and most projects benefit from agility) these phases are still important. And if you are particularly stuck on one or more of them, you significantly lower your chance of being successful.

Initiating: this is where you figure out what you are doing to do. This is the point where you articulate your goal, set a time frame, and identify your success criteria. If you can’t ever get started on anything, you struggle with initiation.

If you can’t kick things off because you can’t decide which option to pursue, the trick is to just pick one (even randomly if you have to) and then promise yourself that you will revisit your choice in a period of time that’s approximately 1/6th of the total. So if it’s a year long project, check back in two months. If it’s a three year project, then it’s half a year. Why 1/6th? Well, first it divides neatly into months and years so you don’t have to think too much. Second, it’s a small enough amount of time to reassure you that you are still on track, but not so small that you can’t get anything done before you hit your checkpoint.

Remember this math is for longer projects. If the thing you can’t decide to get started is going to take under six months, then you should just go ahead and do it and decide afterward if it was the right choice. Because the alternative to not getting started is that you spend those six months just flailing about and end up exactly where you started with nothing accomplished. Life is short but six months is nothing in the grand scheme of things, so just do the thing and then get back to the bigger goals and longer projects.

If your problem is perfectionism (you can’t start because it won’t be good enough) the trick is to schedule a “first draft” into your project. Sure, your new album may not be the best thing ever, but you will spend the first half of the recording time working on a first draft and then spend the second half changing it if necessary. Why half? Because the idea is that by the time you get halfway in, you’ve got so much sunk cost, and you’ve gotten so much better, and you’ve had time to get comfortable with the things that you hated at the start — you will decide you don’t need a second draft after all and you can just finish it! Just don’t tell yourself that at the start. At the start, give yourself permission to suck because “it’s only a first draft” — repeat that mantra whenever you start to freeze up.

Planning: this is where you figure out how you are going to do the thing you want to do. The time you spend planning significantly shortens the time actually doing the thing and bulk of the project management work is planning — you can’t shortchange this step. If you find yourself rushing to get started without thinking about how you want to proceed, you struggle with planning.

If you never plan because you are just too anxious to get started, then make a short list of stuff you can do RIGHT NOW. There are always first steps on a project that don’t require a lot of thought. Maybe it’s basic research, maybe it’s “low hanging fruit.” The point is that you are giving your impatient self permission to do SOMETHING. In the mean time, you schedule yourself some quiet planning time. One chunk right off and shorter ongoing sessions over the coming weeks and months.

Or maybe the problem is that planning seems like a waste of time because everything ends up changing anyway. This isn’t a flaw of planning, its a flaw with how planning is often done. Remember, plan is a verb and not a noun. You don’t plan once and then ignore it, you plan ongoing, tweaking and changing as you go. You plan with the fact that change happens in mind. Here’s a whole post on this topic.

This is also the solve for the second issue people have with planning, which is “I do better when I fly by the seat of my pants — planning cramps my style!” A static plan flies in the face of everything we know about reality, especially magic. You have to be agile and flexible. That said, planning is still good and will make your project go more smoothly. It will help you avoid dead ends and wasted time. If you treat your plan like a flipbook of your project, instead of a static shot at the start, you’ll see how useful a plan can be. Promise yourself that whenever you are hit with a change or new opportunity or brainstorm in your project, that you will go back and revisit your plan. You can even laugh maniacally like an evil villain while changing it if that makes you feel better (you rebel). Usually what happens is that the change or new thing will change some things about your plan that you didn’t even realize, while other things will stay the same (which you also didn’t realize.

Finally, it could be that you just aren’t good at planning, like you have a hard time capturing dependencies and breaking down goals. The best thing here is to talk to a sympathetic person, preferably one who is good at those things. Have them ask pointed questions, poke at perceived weaknesses, and explore what-if scenarios. And record the session so you can go back and remember what you both said.

Executing: this is where you do the work — without it, all the planning in the world will get you nothing. If you have big goals and elaborate plans, but don’t ever make progress on anything, you struggle with execution.

Here’s the big one. In the middle of all this thought and planning and monitoring is the place where you have to GET. SHIT. DONE. There are all kinds of reasons you aren’t doing what you need or want to do. And I have a bunch of posts on this here already. I’m also going to start a mini course on habit formation, parts of which will be previewed in upcoming newsletters. I think that magic for habit formation is a powerful and yet under-explored area and we’re going to dig deep and experiment.

In the mean time, if you can’t get shit done because you are too busy endlessly tweaking your plans, then the solve is the same as the item above. START NOW and then plan as you go. It will work better anyway. And if you can’t get shit done because it won’t be good enough, please see the items above and below on perfectionism. And if you can’t get shit done because what if it all goes sideways, see the bit below on fear of failure under the monitoring section.

Monitoring/Controlling: this is where you watch over things. If you don’t keep an eye on a project, it can go all sideways on you — either finishing with the wrong results or not finishing successfully at all. If you are always doing things, but never taking a step back to look at what you are doing, you struggle with monitoring.

If you have issues with planning, you’re likely going to have issues here. That’s because this is where you update your plan. There are two parts to this. You have to keep track of what you’ve been doing and you have to schedule time to look at that information. This is also where you compare your your current stats with your project initiation information. Are you getting closer to goals? Are you on schedule? Are you successful? Having good data makes this a lot easier and less stressful to do. For example, Circle Thrice makes a certain amount of money and it costs me money too. I can also judge how the site is doing by tracking site and newsletter stats. But if I don’t track these things, it’s hard to know how things are going. By deciding how you will track up front, you make it easier to check in with yourself. You can do this with any project, even “squishy” ones:

Goal, more friends; success = more social engagements
Goal, happiness; success = more happy days based on self assessment
Goal, less stress; success = better blood pressure, more restful sleep, etc.

Sometime people don’t monitor because they are afraid of failure. You’re so worried that it isn’t going well that you can’t bare to look at it. This is the same as when you get behind in a class in school and don’t study and blow a test and you really don’t even want to deal with your grades. You just want the whole thing to go away. But remember, if you are reviewing regularly, things are a lot less likely to go sideways in the first place and if they do, you can fix and adjust quickly so they don’t get too bad. Having an accountability partner is great for this. Maybe it’s the person you told your plan to in the first place. Maybe it’s a friend or family member who wishes you well (important) and cares about you. If someone is waiting for your status update (like your parents waited for your report card), it’s a lot harder to blow this off. You also need to give yourself permission to try things that don’t work out. Because this isn’t school, it’s real life. The only grade is the one you give yourself at the end. Your failures along the way are just for information, so you can try something else. Watch Meet the Robinsons and cut yourself some slack.

Closing: this is where you wrap it up. Like initiating, there’s not a lot to do here, but what there is is very important. If you can never seem to finish anything (either the thing keeps growing and growing or it just lingers and lingers), you struggle with closing.

If you just run out of energy at the end, the trick is to motivate yourself with an exciting post-close activity. An old friend of mine wrote and self-published a book of poetry. A ton of work went into the book and the ending bits were the least fun (layout, proofing, etc.). So she rented a venue and invited all her friends and family to a reading and reception for the kick off. Now that’s a way to stay motivated!

On the other hand, if this is the way perfectionism works for you (it’s never done, it’s never good enough, you can make it just a little better) then what you do is release a beta. In the software world, companies release imperfect applications as betas. The idea is you get it out the door, get some feedback, and then follow up with fixes. Like your first draft, you can promise yourself that what you end your project with will just be a beta. The book you’ll submit, the marathon you’ll run, the new career path… all a beta. Not perfect, but good enough and you can always tweak it later.

If you are absolutely crippled by perfectionism, you could change your entire life by working on first drafts until you kick them out the doors as betas all the while completely tricking yourself into meeting your goals. Believe me, you will not be on your deathbed wishing you’d gone back to make all those project just a little better, but you will regret never allowing yourself to start or finish them.