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

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 coming out September 19, 2017: Reading People: How Seeing the World through the Lens of Personality Changes Everything. Click here to pre-order.

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

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  1. 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!

  2. 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.

  3. 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. 🙂

  4. 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!

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