The tough love guide to planning ahead (if you’re not naturally a planner).

I used to think I was a great planner.

Truly, I’m not. My Myers-Briggs type is INFP—a rather spontaneous sort, who’s not particularly good at planning ahead. I’m likely to realize I want—or need—to do something the same time minute I need to do it (or 5 minutes after I needed to do it), whether this is eating lunch, sending an email, having friends over for dinner, or making a Trader Joe’s run.

I’m particularly fond of the way the book Creative You describes the NP type: they are “an endless lightning storm of ideas, but the bolts don’t often strike the ground.”

That’s my natural type. But when I re-took the official MBTI test last year, I tested as an INTJ: the organized, methodical sort who likes to have things settled.

This result cracked me up, because I am emphatically not “neat, orderly, and established” by my nature.

I came out as INTJ because the amateur test administrator incorrectly told us to answer the questions based on what we usually do, instead of our natural preference. This skewed my result, but it also made me realize that when it comes to making and executing plans, I’ve come a long way. Organization and routine don’t come naturally to me, but I’ve worked hard—especially in these last few years—at cultivating those skills.

My fundamental type hasn’t changed: schedules still feel restrictive, and I prefer to play things by ear. But I’ve managed to improve my “J” skills to compensate for my lack of natural ability. (Do I still need to improve? Emphatically yes. But I’ve made real progress.)

post it notes office

How do you learn to organize and plan ahead when you’re not naturally a planner? This list isn’t comprehensive, but these are the things that have helped me the most:

1. Face the music. For most of us, life requires organization, deadline, and follow-through. It just does. Deal with it.

2. Don’t go all or nothing. You can’t wake up one day and decide that even though you’ve always been a Lorelai, you want to try being a Rory. If you’re spontaneous by nature, don’t try to plan every minute of the day. Prioritize where you put your planning energy.

3. Train yourself to think three steps ahead. Laura Vanderkam compares time management to chess. Master chess players don’t concentrate only on their next move; they think three moves ahead, anticipating outcomes and making contingency plans.

A few years ago, I started training myself to think three steps ahead when I schedule my time, considering possible outcomes and making contingency plans when necessary. (What if the babysitter is sick? What if the internet goes down? What if traffic is a nightmare?)

Logistics are my kryptonite, and I’m a terribly slow decision maker. Thinking through possible game plans ahead of time saves my bacon on a regular basis.

Vogue display board the september issue

4. Pretend you run a magazine. It blew my mind when I first realized (back in junior high, give me some credit) that the Christmas issues of my favorite magazines were shot in the summertime. Approaching my own schedule with the same long-term view gives me the perspective I need to prioritize the right things today.

If I were running Real Simple, my decisions would revolve around not only what needs to happen this week, but what needs to happen 4-6 months from now. When I’m making long term decisions, I mentally put myself in the editor’s chair. This little reframing trick helps me catch many tasks I would otherwise miss, before it’s too late.

5. Learn to break big tasks into chunks. Don’t drop a big project on your to-do list; break that project into granular steps. (Not “write term paper,” but “research chapter 1.”) This is a classic Getting Things Done move. People love GTD because it works.

6. Block scheduling is your friendFor the pantsers among us (as in fly-by-the-seat-of-your), this offers a nice blend of structure and spontaneity. Schedule the block, but don’t get too granular about what you plan to tackle during that time.

A little structure doesn’t kill creativity, it boosts it.

7. Hire (or borrow) some help. If you’re terrible at organizational stuff, hire someone to help you. This might not be convenient for a task like making dinner, but it’s extremely useful if you’re a spontaneous type who’s running her own business. Get yourself a project manager, a media manager, an accountant—whoever you need to compensate for your weaknesses. (As a homeschooling parent, this looks like buying lesson plans.)

My husband is a much better planner than I am, by nature and training. When I need help with the planning—whether it’s for a big writing deadline or an adventure with the kids—I’ll say “I need you to project manage this for me.” (I say this a lot.)


8. Give yourself a fake deadline. Years ago a friend who loved to cook at home told me she always decides what’s for dinner by 10:00. (Preferably 10:00 the night before, but often not till 10:00 the next morning.)

Can you still make dinner at home if you don’t decide what you’re having until 6:00 p.m.? Probably. But the early deadline builds in plenty of time to thaw the main dish, preheat the oven, or even run to the grocery for that item you’re missing, if necessary.

I use this trick for dinner, but I also lean on it professionally. If I have a busy month with several projects coming due at once, I’ll assign myself deadlines that might be weeks in advance of the actual deadlines, because I couldn’t possibly finish all the work if I didn’t begin until the deadlines were looming.

9. Pain is an excellent reinforcement. When it comes to the planning (and, importantly, the follow-through), I still screw up on a regular basis. Natural consequences are real, and they hurt. I’ve found that the pain of failure is an excellent motivation to do things differently next time.

If you’re not naturally a planner: how have you learned to compensate? If organization comes easy to you: tell us your secrets!

P.S. Planning for visual types, and 5 reasons it’s helpful to know your personality type. Image of Anna Wintour from The September Issue documentary, from which I learned all kinds of great information about how to plan my life.

P.P.S. I wrote a book about personality! In Reading People: How Seeing the World through the Lens of Personality Changes Everything, I walk you through 7 different frameworks, explaining the basics in a way you can actually understand, sharing personal stories about how what I learned made a difference in my life, and showing you how it could make a difference in yours, as well.

the tough love guide to planning ahead if you're not naturally a planner


  1. Charlene says:

    Fab tips Anne! I have to say I struggle with the all or nothing thing. I’m like if I can’t get it donw might as well settle down and eat ice cream. I’m working on feeling comfortable with steady progress. I use the fake deadline tip for my appointments. I always record the arrival time as earlier than it actually is. Even though I know it’s a fake time I seem to take it on subconsciously and work towards it.

  2. Jamie says:

    “For most of us, life requires organization, deadline, and follow-through. It just does. Deal with it.” Yes. Hard, but yes.

    Parenting helped me with the time block schedule thing. When someone else’s emotional stability relies on me making sure they’re rested, fed, etc. it’s a good motivation to learn some skills!

  3. Great tips! I’m an INFJ, so I do thrive on organization. However, I hadn’t heard Laura Vanderkam’s tip to think three steps ahead. That’s a game changer! I often find myself stuck if my first plan doesn’t work out. Then I lose momentum and don’t accomplish what I would like to. Thanks!

  4. Kara says:

    I find your experience with the MBTI test fascinating, and similar to my own experience – except exactly the opposite. I took the test in college (ISTJ) and have come to think, over the years since, that with maturity, learning from experiences, and just general sanctification, that our types should be shifting to the middle of the spectrum, rather than becoming more entrenched. Being married for fifteen years to a police officer with an unpredictable schedule has challenged my preferences every day and forced me (because I want to stay married) to be a better, more well-rounded version of myself.

    • Anne says:

      Ah, this is tricky. There’s some disagreement on this, but the consensus is your natural preferences don’t change, but your behaviors do, and should. That’s how you become that better, more well-rounded version of yourself.

  5. Marie says:

    Google Calendar is a huge help for me, a visual person. I can look at the day, the week, or the month as a whole and easily move appointments, color-code kids’ schedules, etc. Plus, I have access on multiple platforms, ending the days of always looking for and/or forgetting my paper planner.

  6. Kristen says:

    This side of things comes VERY naturally to me…what I need to work on is being more spontaneous/go-with-the-flow. I’m afraid I’ve made less progress in that arena than you have in the planning arena!

  7. Heather says:

    I always thought I was INFP but it’s been a while since I took the test and I’m now doubting INFP b/c I am a big planner and I prefer to plan. The very phrase “play it by ear” stresses me out… Ha! Maybe I should re-take the test…

  8. Courtney says:

    I am definitely a Lorelei, but I’m trying really hard to be more like Rory. With three kids, a job, and a super busy life (like everyone else!), planning ahead has become essential to my day!

    Now if you’ll excuse me, I’m off to research my personality type 🙂

  9. Katia says:

    I’m also an INFP and believe that for that reason, I couldn’t wrap my head around project deadlines until I was in high school. Once I understood the importance of planning ahead, I developed a strategy that has worked beautifully and to which I continue to turn now. I use a daily/weekly planner and backtrack from the deadline, looking at what needs to be done a few days before the deadline, a few weeks before, months before, etc. I write everything down and approach each deadline as it comes, keeping the big picture in mind but not allowing it to overwhelm me. This allows me to approach the big project through the lens of micro-projects and at the end, everything appears to have come together effortlessly when, in fact, plenty of work went into the planning and execution. My strategy is very similar to your guide, really. The key is to stay consistent and do the annoying ‘dirty work’ of sitting down and planning in advance. From there, it’s all about staying committed and meeting each micro-deadline.

  10. Hannah Beth Reid says:

    I am a natural planner and have my own separate struggle to flow when the plans go sideways! I think as a parents, we are forced to develop a little of both, the organization to help our children navigate life and a little flexibility because life happens. Thank you for sharing your experiences and suggestions.

    • Anne says:

      “I think as a parents, we are forced to develop a little of both, the organization to help our children navigate life and a little flexibility because life happens.”

      That’s true for me, I think largely because I have four kids of all different ages.

  11. Dawn says:

    Game Changer for me: Moving the repetitive, every day stuff to the morning. This doesn’t work for everything, but if I’m starting a new habit, I schedule it in the morning, before I go to work. I’m working on this with my daughter and her band practice.

  12. I am a natural J and my husband is a P, and it drives him nuts that I’m always doing #3. He thinks it makes me a pessimist, whereas I have tried to point out that he is perpetually caught off guard when things don’t go exactly according to plan. I don’t think he’s learned the lesson of #9 yet, though — he just uses the inevitable obstacles that crop up as excuses for why he doesn’t get things done, not as pain points to teach him for the future.

  13. Liz says:

    Anne, have you heard Gretchen Rubin’s recent work relating to how people respond to inner and outer expectations? I heard her first on The Good Life Podcast and then I discovered she has her own podcast where she talks about splitting people into four basic types based on the way they respond to expectations. She defines inner expectations as something a person expects of herself, like workout more or eat healthily, and outer expectations as something another person expects, like a work deadline assigned by a supervisor. Her premise is that people respond differently to outer and inner expectations, and understanding that about ourselves can help us set ourselves up to keep our resolutions. I’d love to see a blog post about it!

    • Anne says:

      Yes, I have. I think I grasp the concept, but I’m still finding it a little frustrating because I don’t feel like I slot neatly into any of her categories. It’s possible I just need to do some more reading.

      • Liz says:

        If you don’t feel like you fit into a category, you’re probably a questioner. I think the questioner category, of which I am part, is a somewhat strange category, because of course questioners respond to other people’s expectations, not just inner expectations. The way you gather tons of information before making lifestyle decisions, and once decided you go for it with gusto, makes me think you’re probably a questioner, too. If a questioner believes the deadline is true, or respects the boss, or thinks the data is correct, she’ll generally meet the expectation. Anyway, it’s been really fun to look at my coworkers through this lens, especially when one of them talks about being unable to get his high school senior to go to class (rebel!).

  14. I am naturally a planner, and one who tends to freak out if things don’t go according to my plan. Your tip about contingency planning is useful for me. One thing I always did in college was use a giant wall calendar to write due dates on. The bigger, the more visible, the better. I’ve also always taken the approach that I must complete a task as soon as it is assigned in order to make sure it gets done. I usually submitted my research final drafts in the middle of the semester with this tactic!

  15. Melanie says:

    I am a super strong J, so planning and organizing are a couple of my strong points. One thing that might help non-planners is to take notice of how long things actually take. I know quite a few “P” personality people who aren’t realistic about what they can fit in in an hour, which results in them being late, having to alter plans last-minute, etc. If you know that you have to make what is normally a 40-minute drive in rush hour traffic, don’t leave 39 minutes ahead of time, drop off the dry cleaning, and stop by the post office on the way.

  16. liz n. says:

    I think one of the things that comes naturally to us J’s is thinking of the “what ifs” and planning accordingly. We almost always have backup plans. One thing I find common to P’s is that they often try to pack too many things into a short period of time and end up overwhelmed, which leads to more stress. J’s tend to look at all of the parts that comprise the whole, and then break things down into manageable components. Our struggle is to not lose patience with P’s! (Side note: which is why I think we are good managers, but not necessarily good chiefs.)

  17. That’s so interesting that you took the official test and the proctor gave you bad instructions! I took the official twice–once in college and once when my husband and I were going through missionary training. I wish I could get my hands on those test results! To my recollection, I tested as an introvert the first time and at a 50/50 split for E/I the second time. I think I tested as a “J” type as well?! Now I always, always test ENFP on the free tests!

  18. Alice says:

    OMG this, Melanie!
    “I know quite a few “P” personality people who aren’t realistic about what they can fit in in an hour, which results in them being late, having to alter plans last-minute, etc. If you know that you have to make what is normally a 40-minute drive in rush hour traffic, don’t leave 39 minutes ahead of time, drop off the dry cleaning, and stop by the post office on the way.”
    I was once driving out of town with a friend and I was supposed to be at her house at 3. That morning I went to the bank, the liquor store, the grocery store, etc. and arrived at 3. We then got in her car and she proceeded to stop at the bank, the gas station, the liquor store, etc. MADDENING.
    As an ENTJ, I often end up waiting around for people who are always late. But I can’t be late on purpose to combat this because that stresses me out. It is one of the great struggles of my life. 🙂

    • Melanie says:

      I am EXACTLY the same way. If you want to bring out my most uptight, stressed-out, control freak side, cause me to be late for something. I always have a book with me, so when I’m waiting for those punctuality-challenged people in my life at least I get some reading time in!

  19. Block scheduling and breaking tasks into manageable chunks has been huge for me this year, especially since I began blogging. As an INFJ I love planning, but sometimes I spend too much time planning or don’t allow myself enough wiggle room for the unexpected.
    I also just finished Gretchen Rubin’s new book Better than Before, and really enjoyed it. I’m with you though, I don’t perfectly fall into one of her 4 categories, but I still learned a lot from what she wrote about expectations. Knowing that inner expectations are huge for me helps me asses the way I work and plan, and I think will help me stay on track better.

  20. I’m an INTJ for the most part, though when it comes to how I plan my workdays, I’m a bit more into the block scheduling aspect. I have my set of priorities for the day, but only a rough idea when I’ll tackle them. I don’t like to schedule things too tightly (10:00-10:08, do this).

    That said, I agree that running a family and combining work schedules with that too feels less stressful if you’re in the J bucket. The ability to think through things ahead of time (including back-up plans) makes it seem like puzzle pieces, rather than a crisis.

  21. christine says:

    This speaks to me on so many levels! (also an INFP) haha wonderful! I can’t wait to write about this in the future after I make some tweaks to my everyday lifestyle. I’ll be sure to link back to my inspiration 🙂

  22. Paula says:

    I don’t know if I’m naturally a planner or if 15 years in retail made me that way. lol But I plan everything! I know that I’m not always consistent at planning in advance though. I like your tip of the fake deadline. I’ll be using that I’m sure.

  23. Lovely post! I’m an INFP too and struggle most with making and sticking to plans. I so often change my mind, but there is also some part of me that is afraid to make future commitments. I doubt my ability to prepare and be ready to meet those commitments, but I’m learning that is what planning is for! Set a goal and then set clear a clear path to achieve it. One day and one to do list at a time. Thanks for all the tips!

  24. Anne McD says:

    As a fellow INFP, I love reading your blog! Not only are you a few (many!) steps ahead of me in getting order and control in your life, but you have given me a really great roadmap to follow for my personality type! I never realized how important it is in figuring out how to manage your day to day. Thank you so much for sharing–you really have helped me a lot!

  25. Shauna says:

    I’m also an INFP, but at work no one would ever guess my preference is P because I’m one of the most organized people on our team. I can’t think of many work environments where you *don’t* have to be organized and plan ahead in order to manage your time effectively and be a dependable team member.

    I’ve been using a bullet journal for almost two years, and I think that system works so well for me because it’s centered on tasks rather than on a time-based schedule. I never liked using traditional planners because I don’t like having my day scheduled to the minute or even to the hour (though of course, meetings and appointments are a necessary evil). I’d rather know what tasks I need to do that day or week and then do them in whatever order I prefer, not what my planner says I should be doing from 9 a.m. to 10 a.m.

    • Lisa Zahn says:

      Good way to put it! As per my comment below, I’m also loving the bullet journal because it’s not time-based so much as day or week-based. If I can just flow with a general idea of things, I manage to get done what I need to do. The lists in the bullet journal (especially with the “migration” signifier) work well for me because they’re not so restrictive.

  26. Lisa Zahn says:

    As an INFP, even just reading this list gives me hives! LOL. Just kidding (sort of).

    I think I work around my deficits here by keeping life as simple as possible, and not having that much to plan. I did just start bullet journaling and so far, I’m loving having one place for lists. It is making me feel more productive, without having “set in stone” plans for most days. I don’t mind lists as long as they’re not terribly restrictive!

    And for me, the best plans are the ones that get cancelled. 🙂

  27. Vanessa Fisk says:

    Great Article! I always considered myself an organized person (possibly because I am a neat nik), but once I had children I realized I was sadly mistaken. I have been a stay at home/homeschooling mom for most of the past 20 years and I really appreciate your observation that when it comes to hiring or borrowing help “As a homeschooling parent, this looks like buying lesson plans.” I have fought against having a “planned curriculum” for so many years, because I knew that I hated to be tied to one option, but I have realized this year that without an external structure to guide me I get nothing useful done – there are way too many possibilities. So this year I am using a pre-planned curriculum and hoping for positive progress, and knowing “why” I need to embrace this approach makes it much easier for this creative mind to accept the structure. Thank you for your insights!

  28. Tanner says:

    It’s so funny how many INFPs are posting on here. I am an INFP, and I never realized that we are all naturally planning-handicapped. I remember watching part of an interview with the late Joan Rivers. She said that her worst fear was an empty calendar: no one wanted to see you and your time is not important. I came to realize at that moment that some people have very different views from mine of an ideal lifestyle.
    In any case, I need to change. The lack of planning in my life makes me unprepared and constantly trying to catch up– also not good for me as an INFP. I loved your suggestions, and I would like to know of books that would reinforce your ideas. I noted “Getting Things Done”. Anything else?

  29. Tiffany says:

    I was just googling how to learn to plan ahead it seems like a simple concept but man do I struggle. When I read that you are an infp like mean I knew I found the right article ? nobody gets our thinking process like we do. I am striving to be more organized and thankful for this article it was really helpful.

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