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Does Your Life Need An Outline?

If you’ve ever written a research paper or tried to write anything of “serious” length, you may have struggled to put together an outline.

For instance, in High School English, my paper on The Scarlet Letter might have looked something like this:


  • Hats with buckles – I don’t want one160x160_pilgrimhat
  • Pilgrim life sounds awful


  • Powdered wigs – no thank you
  • Those hats with buckles…seriously?


  • Hester Prynne sounds like a firecracker…yow!


  • Arthur Dimmesdale is a wiener.
  • I’d rather be reading something about zombies
  • My head’s too big for those hats anyway

And so on…

As I’ve struggled to write a book proposal in the last couple of months, I’ve had to take the concept of the outline much more seriously.  The problem has been, it’s not normally how I write.

It’s not how I write because it’s not really how I live.  I usually prefer not to know what’s coming, unless I’m talking about a goal that is easily mapped out – like pressing a heavier weight, for instance.

Aerosmith – You win this one

Life’s a journey, not a destination

I’m going to ignore that for a second and try to figure out what an outline of my life might look like.


  • Baby boy with enormous head born in Moab!  Nurse accurately prophesies that boy will not grown into his head until age 32.  By that time his head has swelled so badly from his ego that he can never wear a hat again
  • Boy gets really tall
  • Boy’s brain decides it’s on a kamikaze mission and he starts twitching like a jumping bean


  • Tall.  Stringy.  Like a big pale piece of constantly vibrating jerky

Notable events

  • Reads a lot
  • Starts a blog just to prove that he has nothing to say
  • This plan backfires in a big way

Themes, Motifs, Recurring Symbols

  • Scars
  • Injuries
  • Jokes
  • Bent glasses
  • Books
  • Crack pipe (whoops!  That was supposed to be for another post…hmm…can’t figure out how to delete it…)
  • The war with one’s body
  • Family
  • Friends


  • I don’t want to know

What do you think?  Do you plan your life out?  Which things do you leave to chance, and which things do you actually try to make an outline or plan for?

How do you know if you’re reaching your potential?  How do you know if you’ve made the most of your time?

If there are enough comments, maybe I’ll come clean about that crack pipe, yo.


PS: Did you get a guest post from me yet?

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  • Kira September 28, 2009, 4:22 am

    I do use goals and plans, but I’m much more interested in experiencing the PROCESS … I focus on framing ‘WHO I am’ and then let the unfolding ‘events’ of my life take care of themselves.

    • Josh Hanagarne September 28, 2009, 7:36 am

      Kira: your facebook update yesterday today said, “I’ll be hitting and throwing thing today.” That might be the best outline I’ve ever seen:)

      @Laura: Vanilla Ice said something similar in his movie, “Cool as Ice.” I believe it went, “You gots to be true to yoself, and true to nobahdy.” If you liked the guest post, read the Cheese Monkeys!

      @Greg: Kids certainly change things, don’t they? Nobody would laugh harder at my plans than my toddler.

      @Beth: Which section did you write? Maybe I’ll avoid that one…

      @Casey: You probably know, but that movie was called the Mosquito Coast. Bizarre film. It’s from a great book by Paul Theroux, who’s fantastic if you like travel writing. Thanks for reminding me. That was a movie my mom rented for me when I was sick in middle school once. I still remember him yelling, “Ice! I give you ice!”

  • Laura - The Journal of Cultural Conversation September 28, 2009, 5:12 am

    Can I hire you to write me a new life outline?

    I, like Kira, am always focusing on goals and plans – and often don’t consider the process. I don’t know if I actually know how to do that, except through practice and a bit more awareness. Goals and plans are important, but I sometimes feel like I fall short, only because .. well .. life happens and we all need to be a bit more flexible with our outlines. The most we can do, I guess, is just remain true to who we are.

    Thanks again for the great guest post Josh – truly loved it.

  • Greg September 28, 2009, 5:23 am

    I used to try to plan my life out. I usually ended up having to toss the roadmap out the window somewhere along the way though.

    Then I got married and had kids. Enough said… 🙂

  • Beth L. Gainer September 28, 2009, 7:19 am

    Hey Josh,

    Arthur Dimmesdale was a turd.

    Anyway, I used to try to plan out my life, but another great musician, John Lennon, said in his song “Beautiful Boy,” that “Life happens when you’re making other plans.”

    I have found this to be true. I could never have predicted where my life was heading, and I have to say, I’m happy with the way it’s turning out. I am disciplined, though, when it comes to making time for writing and oil painting. I get up at 5-ish to get stuff done before the baby awakens around 7-8 or so. I also use her nap times to get things done.

    BTW, book proposals are hellish. I wrote one section, and it just about killed me. Still have miles to go before I sleep….

  • Casey September 28, 2009, 7:26 am

    I think a lot of people toss out their goals and blame it on “life is unpredictable”. Personally I think that is a huge mistake. A life without goals, destinations, whatever, isn’t a life, its survival.

    There was this really weird movie with Harrison Ford where he is trying to bring a hunk of ice to a bunch of tribes deep in the Amazon. The movie sucked, but he says: “Dead things go down stream, living things go up” Living life means progress, not just floating along with the current waiting to see what bumps into you.

    Without goal or an outline, you are just drifting downstream with the current. It takes hard work and effort to reach our goals, even more so when you factor in our unpredictable lives… That’s what makes it so rewarding when we achieve those goals!

  • Mark Wolfinger September 28, 2009, 8:30 am


    “As I’ve struggled to write a book proposal in the last couple of months, I’ve had to take the concept of the outline much more seriously. The problem has been, it’s not normally how I write.”

    I find it too difficult to write outlines. Every time I write a magazine article that requires an outline, I finish the piece first – and go back to write the outline.

    But that method is not viable for books.

    • Josh Hanagarne September 28, 2009, 8:56 am

      @Mark: I should clarify. When I write fiction, I don’t use an outline and it makes it much more enjoyable for me, the now knowing. With non-fiction, it’s just not the way it’s done, which I didn’t know going into this. What do you find most difficult about writing an outline?

      @John Bardos: Normally I would have said “Amen” to all of that. Once I’ve actually started dealing with agents and publishers a bit, the last thing they want to hear is that you’re going to take your sweet time delivering something mediocre, but that it’s cathartic for you:) Money changes everything, yes it do…

      @Heather, crack pipe coming right up…

  • John Bardos - JetSetCitizen September 28, 2009, 8:47 am

    I think it is important to have a rough outline for life. Changing direction everyday will just lead you in circles. However, no outline should be written in stone.

    Spend some time soul searching to come up with the best “life outline” you can. Then execute the plan. Finish the current “book.” If it sucks and your mother won’t even read it, at least you have finished one “book” or chapter in your life. Give them away as door stops if you have to.

    Most certainly the second “book” will be much, much better. Life is not one outline or “book.” It is a whole series. Too many people continuously abandon dreams before they ever have a decent chance at success.

    It is much better to spend a couple of years delivering a mediocre “book” based on a flawed outline, then to spend a life always searching for the perfect outline.

  • Heather September 28, 2009, 8:50 am


    Dimmesdale was a tool. So as far as outlines go—-I only use them for papers, and only when I absolutely have to. If I can bulls*** my way through something, I will, simply because I can and I’ve been doing it for years. Plans, though, that’s something a bit different. I plan lessons and presentations, and I plan workouts. As a used-to-be wanna-be novelist, I used to outline those. I hate outlines. I also hate those hats with the buckles. Shoes with buckles I understand. But hats? Come on! Now about this crack pipe, yo.. . .

  • Joey September 28, 2009, 9:36 am

    That was brilliant. And I think that gives me a great idea for a guest post on my website! You could write about how your plan “to prove that [you have] nothing to say” backfired.

  • Shane September 28, 2009, 9:54 am

    Josh, the “process and procedure” are boring you. Do it anyway, just submit it in crayon…in your underwear…while bending steel…while smoking crack.

    In other words, follow procedure, but have a damn’d blast doing so in your own special way, with your own subset of “rules.”

    Think of a piece of paper…BORING.
    Creative people turn it into Oragami…EXCITING!

    It’s all in how your mind categorized “outlining” that makes all the difference, and allow your fun to come through regardless.

    • Josh Hanagarne September 28, 2009, 11:02 am

      Shane: will do. I’m going to fold up an origami crack pipe, smoke it, then wrap the burnt paper around a bent spike, then throw it into the river and hope it drifts down to NYC. Seriously, you make great points and I can tell you speak from experience.

      @Larissa: Maybe that’s my problem–I’ve never owned a pencil.

      @Pete: Is this typical for dyslexia, that you discover it at a later age (not a kid, meaning)? How has it affected you?

  • Larissa September 28, 2009, 10:16 am

    Maybe that’s my problem! I love writing outlines. . .for everything! The problem is that I think I know the outcome, and it is almost always ends up being opposite of what I thought. Just write in pencil and be prepared to erase. 😉

  • Casey September 28, 2009, 10:41 am

    When it comes to writing an out line I try to thnk of it a s skeleton. It’s simply some bare bones to get me from point A to B to C and then wrap it up without sounding like an idiot.

    All the stuff that goes in between those points are free to shift and slide depending how things flow the best. Maybe it’s not a true outline, but it works for me!

  • Panayiotis Pete Karabetis September 28, 2009, 10:52 am

    Here comes the seriousness…

    I recently discovered, coincidentally the same time I began writing, that I have a mild form of dyslexia. Throughout my school years, I was a whiz at outlining and list-making, but something changed this past June.

    Life is fine, in fact it’s good, but this literally flipped my world upside down.

    I kind of like not being so organized, though. Who would have thought?

  • Ayelet September 28, 2009, 1:01 pm

    Oh, I love outlines! I can’t start a project without them…I guess Project Life Fulfilled shouldn’t be any different. I’ve discovered recently that I’m constantly updating my Life Outline depending on likes and dislikes (no, I don’t want to watch twenty screaming children for a living, thank you very much). And I think a flexible Life Outline is a good thing (apparently I’m channeling Martha Stewart at the moment).

  • Panayiotis Pete Karabetis September 28, 2009, 1:15 pm


    I have a hell of a time reading books and lines of text that contain more than 9 – 11 words. My mind wanders and I have to start over.

    If I’m on a computer, forget comfortable reading! I’ve gone back to taking notes on scrap paper and ditching the digital craze.

    Seems to work great for me for some reason. In many ways, even though life has gotten a little more annoying, it’s simpler in a good way.

  • Shane September 28, 2009, 1:50 pm

    “Seriously, you make great points and I can tell you speak from experience.”

    …good points about crack? :).

    Seriously, whatever you do, start off your book with the 1st word being a power verb!!!!!!

    • Josh Hanagarne September 28, 2009, 2:39 pm

      Shane, the first word in the book is going to be “ninjas.” That I’m not budging on.

  • Lori September 28, 2009, 1:51 pm

    I usually use an outline to get going then dump it once I get going. I think it is kind of like a lubrication for getting the writing fingers up and running. Maybe that will change when I get more serious with my writing goals. (?)

    An outline for life? Well, my initial plan to become a ballerina tanked when I started powerlifting at age 15, then my plan to join the Secret Service or FBI failed after I finished my service in the US Army (reasons to be explained at a later date). My next step is to develop superhuman powers – at least to be able to read minds. I’ve always wanted to do that.
    Great Post!

  • Jon Owens September 28, 2009, 1:55 pm

    Interesting post today Josh and it has me thinking. My two cents? An outline of your life should be “bare bones” — have goals, dreams, aspirations, etc., but not to the exclusion of seeing what you are doing or have done that didn’t make the outline but are still pretty darn cool.

    My life’s a work in progress. While I have certain goals, etc., some of the best things I’ve done (in my view) would never had made an outline. Either because at the time they didn’t sound like a good idea or seemed insignificant in the grand scheme of things. Looking back though, they are defining moments which I wouldn’t trade for an outlined perfect life.

    • Josh Hanagarne September 28, 2009, 2:42 pm

      @Jon: I like the bare bones approach. How’s your bending coming? How’s the legal world? Are people still breaking the law?

      @Lori: What was your job in the Army? Were you an assassin?

      @Pete: Glad to know you’re able to get through it. I can’t imagine how much difficulty with focusing would change my life.

      @Ayelet: And how is the essence of Martha Stewart working out for you?

  • Lori September 28, 2009, 3:27 pm

    My career in the US Army was in the area of military intelligence. I could tell you more, but, I’d have to …

  • Julie Goodale September 28, 2009, 4:25 pm

    I’m a musician, personal trainer (specializing in cancer survivors), & in my spare time like to climb mountains & windsurf. When I’m climbing a big mountain, I’ve definitely got plans. I made serious training plans to get ready for the climb; I make plans on how I’ll pay for the trip; and we plan the route, our food, & timing. But with all that planning, I never know if I’ll actually make it. It’s not for lack of determination (I’ve summited many mountains, puking the whole way-I am determined!). But lot’s of things can happen in the mountains: weather, injury, illness, weather. To me, though, it doesn’t really matter. Climbing is what matters, not the summit – and sometimes not reaching the top is part of climbing.
    It’s a little like life – or at least my life.
    And I was sitting down to write a new post for my blog, and ended up here instead….

    • Josh Hanagarne September 28, 2009, 4:27 pm

      Julie, when and where is your next big climb?

  • Jessica Marie September 28, 2009, 4:34 pm

    When in doubt, go chronologically or by subject. If neither really appeals to you, do a combo. Have the first half of the book be birth to present then have the second half be dealing with various aspects of your life (ie marriage, work, medical stuff, having kids, etc.) I think you are thinking too much about this.
    As to my own life, I have an outline but it changes according to events. I love outlines for projects because it helps me plan what I need to do.

    • Josh Hanagarne September 28, 2009, 5:20 pm

      Jessica, I’ve made it sound worse than it is. I didn’t mean to imply that because I struggled to write the proposal, that the proposal didn’t do what it was intended to. It did exactly that. It was just a new experience. A very new way of writing for me. It felt like a high-stakes book report for a book that didn’t exist yet.

      And one of the comments from more than one editor was exactly the opposite of what you say be “have the first half of the book be birth to present.” Most of them resisted an obvious chronology.

      going by subject was exactly what worked.

  • Joel Friedlander September 28, 2009, 5:40 pm


    Outlining can be brain-deadening, or you can experience it as a kind of freedom because no matter what crazy idea you come up with, it can “find its place” somewhere in the outline. No logic or cause-effect relationship needed.

    I’ve often advised clients who were having trouble with their non fiction project to try outlining because if you make your outline sufficiently granular, you can write an entire book a few sentences at a time. How non-threatening is that?

    Good luck.

  • Tim September 28, 2009, 7:54 pm

    Hi Josh:

    Another enjoyable thought-provoking post. I have not used any sort of outline for my life, but I am realizing that I probably should (at least a little one). I don’t have any 5 or 10 year plans, either. However…based on a lot of books n blogs I’ve read…including our buddy David Cain at Raptitude, I am feeling the necessity to complete my life list…I can use it as a written “vision board.”

    • Josh Hanagarne September 28, 2009, 8:01 pm

      Tim, I read David’s life list as well. Great stuff. When you get yours done, let me know.

  • Shane September 29, 2009, 6:45 am

    ok. How about this compromise opening for your book:

    “Killing Ninjas is…”

    • Josh Hanagarne September 29, 2009, 7:32 am

      Shane, you win. That’s a power verb for sure.

  • Michele | Writer's Round-About September 29, 2009, 11:24 am


    I’m a planner, Josh. Yep, I could outline my entire life. I’m boring, huh?

    I wrestle with this weird habit, but I find myself planning everything down to my shopping list–with items listed according to which aisles they’re on.

    I’m not proud of this at all, by the way. I wish I were like so many other people, who wake up and step into life without planning a thing, just living for the experience…

    This is such a fun post, though. You’re so creative!!!!


    • Josh Hanagarne September 29, 2009, 12:00 pm

      Michele, I don’t think it’s anything that you shouldn’t be proud of. Sounds it’s just something that “is.” All those other people you want to be like have all sorts of problems of their own.

  • Michele | Writer's Round-About September 29, 2009, 12:19 pm

    I suppose that’s absolutely true, Josh. Thanks. 😉

  • Beth L. Gainer September 29, 2009, 2:17 pm

    Hey Josh,

    It was the “About the Book” section, which unfortunately, you can’t bypass (and I almost needed a bypass writing it). Started working on the “Concept Statement.”

    The good thing is that the “About the Book” section is finally done. Now only a zillion more sections, and I’m done!!

    • Josh Hanagarne September 29, 2009, 6:58 pm

      Beth, they won’t let you skip “about the book,” huh?

  • Warren Talbot September 29, 2009, 8:30 pm

    A few years ago I would have been able to tell you where my life was going and roughly what I would be doing in 5, 10, 20 years. I was on a rather typical path of life (job, wife, dog, friends) that would lead to new and more challenging job positions, bigger houses, and more expensive tastes in wine. Instead, we chose to step off the “normal” path and are in the process of selling everything we own and travel the world for a few years. The result since the decision….I have never been happier in my life! I hope I never have an outline for my life as I want to always be able to experience the new and enjoy the spontaneous.

    As for the past, I decided to create a “twitter-like” summary of life to answer those annoying questions on Facebook “what have you been up to” and to quickly remember why I am where I am today:

    1993 – took my dream job at Toys R Us
    1994 – moved to Dallas, learned retail sucks, joined Software Spectrum. Got engaged (Jamie)
    1995 – learned I was an idiot, broke off engagement
    1996 – enjoyed the single life, got promoted to Supervisor
    1997 – met a woman (Deanne, moved to Seattle, joined Microsoft (yes, the Evil Empire)
    1998 – got engaged (again). I forgot I am an idiot
    1999 – got married to wife #1, started a company (cMeRun), got my dog (Max)
    2000 – moved to Boston, took company public, found out it snows a lot here
    2001 – closed company, investors in jail, moved to Washington DC area
    2002 – joined company to be turn-around CEO, moved to East Philadelphia (aka NewJersey)
    2003 – got divorced, met amazing woman (Betsy), still living in NJ…
    2004 – got married (yes, again), honeymoon in Paris, moved to Boston (yes, again)
    2005 – loving New England, became rbpid Red Sox fan, went to Germany/UK
    2006 – moved to Seattle, joined F5, went to Barcelona
    2007 – really enjoying wine and living in the city, X-Mas in San Francisco
    2008 – joined Microsoft (again), vacation in Hawaii, decided to travel around the world, started learning Spanish, traveled to Asia
    2009 – went to Pro Bowl, got promotion, ???

    WHEW, seems you really struck a cord with me. Thank you that!

  • Andrew September 30, 2009, 8:13 am

    OK I am going to shamelessly steal your format and plug in my own info….

    Hello I’m Andrew, it’s nice to meet you.
    Short, round, thick, hairy, Imagine a Pygmy Sasquatch
    Notable Events:
    – Odd somewhat stress filled childhood including a landslide
    – Discovered an unusual talent for chasing a round white leather object on a big chunk of grass with two wooden rectangles at the end
    – because of above talent got to go to college despite beeing a lousy student, also got lots of free stuff and met hot library chick that had a thing for guys in shorts.
    – became a School Psychologist
    – somehow got talked into beeing a Special Education Administrator
    – Started picking up, carrying and throwing things in front of large crowds of drunks
    – Brain exploded
    – Returned to picking up, carrying and throwing things in front of large crowds of drunks
    – Assisted in creating two wonderful children that fortunately look more like hot library chick mom than Pygmy Sasquatch dad

    Themes, Motiffs, Recurring Symbols
    – Heavy Stuff
    – Kilts
    – Things with 2 wheels
    – Numbers, lots of numbers

    Women dig guys in kilts

    • Josh Hanagarne September 30, 2009, 8:32 am

      Andrew, you took the format but your outline is way more entertaining than mine. “Brain exploded.” “Hot library chick.” “Pygmy sasquatch.” You had me at “throwing thing in front of large crowds of drunks.” Oh man, this made my day.

  • James September 30, 2009, 9:58 am

    Andrew: “…picking up, carrying and throwing things in front of large crowds of drunks.”

    That can only be the caber toss…or were you a roadie?

  • Andrew September 30, 2009, 11:44 am

    Actually a little of both. for the past few years I have competed in Highland Games and soon will hopefully be doing my first sanctioned strongman contest. Several of my family members including my dad are/were IATSE members (the stagehands union) and during college I worked some shows during the summers. I actually was thinking of that during the “odd childhood” part rather than the throwing, but now I’m thinking you’re right… the throwing/carrying/drunks could apply to both.