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Scanning the Skyline: How Far In The Future Should You Plan Your Life?

Summary: In this post, I discuss my struggle with obsessive compulsive disorder, and explore the arguments pro and con a well planned out life.


I was recently diagnosed with OCD (that is, obsessive compulsive disorder). I’m hardly ashamed, or particularly shocked in fact. A little confused perhaps, but otherwise, the diagnosis has been a serious wake up call. The only way I can describe it is that a window into my nature has been cleaned that I didn’t even realize was dirty. Looking back, it certainly explains waking up in a cold sweat and making a calendar out of post-it notes. Background information: waking up in a cold sweat over unfinished tasks happens about 3 or 4 times a day, whether I’m sleeping or not. For example, I’ll be sitting down eating a meal, and I’ll be plagued by the idea that I need to drop everything and get back to work. I’ve always thought that all high achievers push themselves the way that I do. But I have lots of high achieving friends and I realize now that none of them ever beat themselves up as much as I’ve been doing all these years.

I’ve gone this far without anybody catching anything because, well, the fruits of my compulsions are visually appealing things like post-it calendars that I can blog about, and good grades, and other grand achievements. I’m right on track with learning to control my obsessions and the resulting compulsions, but this whole “increased self awareness” thing has got me wondering about where my OCD ends and where the planning methods of the average person begins. 

I can’t leave the house without a book in my purse, or checking and re-checking my purse a million times to make sure I have a book in there, lest I finish a task and am forced to sit around with idle hands. I must always have something to do, or else my head starts to feel funny. I’d describe it as though the walls of the room are closing in on me, and my head slowly fills up with pressurized air that becomes hotter and hotter until I find something for myself to do- usually rearranging my surroundings. And you can bet I can’t sleep unless I feel like I’ve done all that I can to do all that I can each day.

I began using David Allen’s GTD method a few years ago, because of the fact that it is based upon the principle of maintaining never-ending to-do lists, organized by context of when you can do any given task. And then I learned about Cal Newport’s GTD for college students method. I’m sure you can see how much of an enabler GTD has been for me in the past few years. It never even occured to me that my constant need for always accomplishing something was out of the ordinary, until I sat down with a therapist and explain out loud how stressed out not having anything to do gets me. Hearing myself describe my daily thought process was a real wake-up call as to how out of the ordinary and incredibly unhealthy, my daily thought process actually is.

Learning to change my thought processes and behaviors  has been emotionally trying. Mostly, it’s been a lot of facing my fears. It’s also been a lot of trying to figure out where to draw lines and boundaries.  Feeling stressed about work on occasion is normal, and probably a little healthy. Making to-do lists so you can get in control of your workload is also OK. Fleshing out goals for yourself on a regular basis so that you feel proud of your life, and like you’re contributing to the world is also OK. Showering or exercising excessively for hours on end so you feel like you’ve accomplished something that day is not OK, nor is it particularly healthy.  Making lofty goals for yourself so you never have to run out of things to do is not healthy either. Planning out each second of your day and getting salaciously upset when your plans get derailed is also neither OK nor healthy. My biggest question for the past 4 weeks has consistently been: what do I actually need to plan and what do I need to learn to release to the ‘randomosityness” of life? And yes, randomosityness is a word- it perfectly describes how ridiculous and unnecessary I think it is to leave things to chance. (But I’m working to change that view!)

I have daily goals, and weekly goals, and monthly goals and yearly goals. And then of course I have my 5, 10, and 15 year plans. And then I have my life list. But the thing is, a lot of people have these kinds of goals. If you reverse engineer, these goals make a lot of sense. You begin with a vision of the kind of life you aspire to (e.g. a life list, or a mission statement) and then break your lofty aspirations down into action steps. That’s OK.

My theory is that what separates healthy goal setting from obsessive life planning is how it all makes you feel at the end. I often feel like I’m a slave to my goals and plans. I make plans to liberate myself from temporary anxiety, but then feel trapped by said plans.

I think it’s the same with those people who are the exact opposite of me- the one who “live for the moment” and “go with the flow” all the time. I used to look down on those people for never having plans. And to be honest, I still don’t really regard people with no path in life with particularly high esteem. There is a difference between trusting the universe to get you where you need to be, and just straight up being lazy. And when it comes to the day-to-day planning of how you will go about your life, I think the benchmark is how much progress you are making towards your goals. People with no vision, or who are afraid of making plans are also just as trapped within their lack of direction as I am within my over-planning. A certain amount of kicking yourself in the ass is important, because it gets your ass moving. You then draw the line in ass kicking when it begins to dis-empower you.


What I see, and admire and aspire to, and wholeheartedly recommend it planning until you feel liberated. Perhaps you feel liberated by  a 5 year plan, and anything more feels like too much. So that’s where you stop. Or even better, what I really aspire to are those people with daily to-do lists that don’t feel like they’re trapped within their plans. They set realistic goals, and they accomplish them.

But you know what else? I think that everyone has to draw these lines in their lives, whether they have OCD or not. If you’re not living your ideal life right here, right now, then you either need to do a little bit more, or a little bit less ass kicking. We all have an ongoing process within ourselves of finding the right balance between slacking and not slacking that keeps us chugging away towards what we want. And ultimately, what I am learning more and more is that it’s not crossing things off your to-do list that makes you successful, but being able to sleep at the end of the day, having enjoyed your entire waking period, and feeling secure in yourself.

I have no actionable list for you all in this post- making less of those is part of my personal action plan. (Oh the irony and contradictions!) I just wanted to get you thinking about your own thought processes.

How is the way you think about your goals, both big and small, affecting your ability to get things done? Are you pushing yourself so hard that you’re tired and overworked? Or are you dragging your feet on a treadmill set to low? Or are you chugging along at a healthy pace and need to share your secrets and tips with the rest of us?

And regardless of where you stand on the workaholic spectrum, what can you begin to do, right here, right now to improve yourself?

Example: For me, it’s realizing that I just tossed an action list into this article, and that my point of improvement is not getting too upset with myself for doing so.

Hopefully, I’ve given you something to ruminate on for a while. At first, it’s a little difficult to face those inner monsters. But if there’s one thing I’ve learned over the years of working myself to exhaustion, it’s that work breeds more work. The more you think about how your mental habits are affecting your physical habits and actions, the more you keep thinking about it. The more you think about it, the closer you’ll get to that “Oh my gosh, I need to get up and do something about this right now!” stage of action. And trust me- you don’t need an anxiety disorder to get up and do something about your life. :) When you’re done ruminating, you should give me a shout on how you feel about this topic.

P.S. I’ve got twitter. You should follow me! I’m basically an endless stream of witty!

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10 Responses to “Scanning the Skyline: How Far In The Future Should You Plan Your Life?”

  1. Studies on happiness have shown that 10 years, 5 years — even 1 year in advance — people have a lot of trouble accurately determining what will actually make them happy.

    I think a lot of productivity stuff actually supports that, if you look for it. Tim Ferriss certainly doesn’t embrace the idea of planning for retirement.

    That’s why I love the lifestyle of a freelancer. It’s scary not knowing what’s next, but I can always do what makes me happy right now. Because that’s one thing I know for sure.

  2. Ayomide! says:

    Yeah, it’s the learning to be happy in the now while balancing responsible planning for the future that we all struggle with, isn’t it? That’s why it become so important to be able to change your plans accordingly.

  3. Hey, I won’t sweat it too much, as you’re at least getting your stuff done! Apart from regular blog updates, that is ;-)

    Whatever you do, do not take any medication for your “ailment” as the pills will just make things worse. DO you suffer from anxiety and/or panic attacks at all?

  4. Hey, I won’t sweat it too much, as you’re at least getting your stuff done! Apart from regular blog updates, that is ;-)

    Whatever you do, do not take any medication for your “ailment” as the pills will just make things worse. Do you suffer from anxiety and/or panic attacks at all?

    Anyways, keep your chin up and do what feels right for you, OK! Best of luck, and we all look forward to hearing more from you! God Bless.

  5. Suzannah says:


    I am happy for you that your found out about your OCD while still in school. It completely sucked for me to figure it out afterward!

    As you might experience yourself, OCD can come with a smidge of ADD as well. For me, a lot more of a smidge. A life of “i MUST organize it but where the hell did i put it?” and of “I MUST finish something but i will be damned if i remember what it was”


    all I can say is that GTD is a GODSEND. be picky. make as many contexts as you need. try to keep it within two flips of an organizer or two clicks of a mouse to get to your contexts though. But my best advice is this: use the check lists and the someday/maybe lists as permission. when the compulsion overwhelms you - and thus eats out large chunks of your day - use the someday may be to dump it out of your head. Use the 2 minute rule (can i do it in 2 minutes? No? write it down in a context and move on.) to give yourself permission. GTD gives you permission to let down the compulsion. use it!

    best of luck!

  6. Thats pretty cool. I have never been to Ireland, but im originally from the UK in its pretty miserable over there! Ireland is meant to be absolutely beautiful!Awww its so awesome to hear other peoples dreams. I guess it just shows how different everyone is.

  7. Its a nice write up i must confess

  8. OCD is new topic for me. Thanks for information about it.

  9. planning the business: yes but i don’t make plans if the matter is fun.

  10. Hey, I won’t sweat it too much, as you’re at least getting your stuff done! Apart from regular blog updates, that is