Planning: The Not-So Secret Success Tool That Anyone Can Use

business_planSome people love to “fly by the seat of their pants.” If they take a trip, they take it one day at a time and decide each day what they will do. If they start a household project (like painting the fence), they get up each day and if they feel like it, they paint. If they go into a store, such people don’t along take a list. I could go on and on. . .

There are “seat of the pants” clients too. You’ve probably worked for some of them. They’re the ones that contact you at 4:00 p.m. on a business day and ask if you can have a project done by tomorrow. They’re also the ones who assign you a deadline and then go on vacation because they don’t really mean it.

For the most part, I don’t fault the “seat of the pants” folks (much). I know that planning is just not part of their nature. They can be wonderful, impulsive, and fun folk.

However, working by the seat of the pants can also set you back if you’re running a freelance business.

Planning: A Tool For Success

If you’ve been reading FreelanceFolder for a while, you’ve probably picked up on the fact that I tend to be a planner. You’ve probably noticed that I even have a template for when you can’t deliver a project and a list of questions to ask new clients.

I even use planning for my FreelanceFolder posts — outlining at the beginning of each month topics that I will cover during that month. I keep notes on my computer for each topic as ideas occur to me. When it comes time to actually write a post it’s often just a matter of polishing my original outline and elaborating on my thoughts. (I’ve tried the method of sitting down cold and trying to come up with post on the spot and find it to be much less efficient.)

I think that planning is a key tool to running a successful freelancing business. In fact, I like to think of planning as my secret super success tool — except for one thing. It’s not really a secret at all. Anyone can use planning to improve their freelancing business, but not everyone does.

Pitfalls for Planners

One reason that some freelancers may be hesitant to rely much on planning is that there are pitfalls for planners that can make planning frustrating. Some of the pitfalls include the following:

  • Life doesn’t cooperate — Everybody probably remembers a time when they thought they had everything all planned out, only to have that plan meet with obstacle after obstacle.
  • Becoming too inflexible — Another planning pitfall is relying so heavily on your plan that you refuse to budge from it even when circumstances have changed.
  • Stressing over disruptions to a plan that are not your fault — Sometimes having a plan can create stress, particularly when something does not go according to plan.
  • Not considering others in your plan — Nobody works in a vacuum. We all rely on clients (and often colleagues) to complete our projects. Often these people have plans of their own.

With the right approach, however, these pitfalls to planning can be overcome.

How to Overcome Planning Pitfalls

There are a few techniques to overcome some of the frustration that planning can cause for freelancers. Here are several:

  1. Have a Plan B — It’s a good idea to have a backup plan for even the best plan. You never know when something unforeseen might happen. A backup plan can reduce a lot of stress.
  2. Be open to others’ ideas — One of the best ways to learn and expand your business is to learn from others. When you present your plan to clients or colleagues, listen to their suggestions.
  3. Don’t sweat what you can’t control — Even with a backup plan sometimes things spiral beyond your control and there’s nothing you can do about it. Recognize when this occurs and relax. It happens to all of us.

What’s Your Planning M.O.?

Are you a planner, or do you “fly by the seat of your pants?”

What do you find to be most frustrating about developing plans for your freelancing projects (and how do you deal with it)?

Share your thoughts and stories in the comments.


  1. Jared Penner says

    Great article. I am a seat of the pants type of guy. But if I have a project in front of me I know everything need to be planed. What I try to do is make my plan more goal oriented. I don’t have one set task I want to do but something I want to get done. (that doesn’t sound quite right, not sure how else to put it.)
    And the biggest thing is to be flexible it never helps to stress out, in fact I find it makes thing worse.

  2. says

    Thanks Jared! I appreciate your perspective as a seat of the pants type guy.

    Even if things don’t go exactly as planned, I’ve found that it’s helpful to have a plan to use as a guide.

  3. Jorge García says

    Hola desde México, en lo personal si me gusta planificar mis actividades, por el trabajo de planta que tengo, es indispensable esta herramienta y uso tanto el calendario del Outlook, la agenda planificadora e incluso el teléfono celular para recordarme algunas citas o eventos cuando estoy en la calle.

    Desafortunadamente me he encontrado con que algunos de mis clientes no aplican la misma organización para sus actividades y rompen en la mayoría de los casos con la armónica organización que había proyectado el fin de semana (que es cuando me dedico a planificar).

    Planificar se convierte en una estrategia para que tanto tus clientes como tu propia persona encuentre la tan valorada armonía, que dicho sea de paso en estos tiempos en los que salir al cine es imposible sin fallarle a otro compromiso.

    Exelente artículo Laura y espero no te cueste trabajo leer en español.

    Jorge A.

  4. says

    What a fantastic and practical piece!

    Many people fail to plan. To me, the most important thing about planning is to prepare the mind on the what and how of achieving a goal. It sets the direction and motion.

    To plan, you have to really think about how to do something. Even if the reality differs from the plan, the thinking will serve to guide decisions on how to adjust and change. As you’ve mentioned, a plan will meet many challenges. But planning itself is the process to prepare yourself for challenges.

    My experience is, even under highly uncertain circumstances, putting some efforts in working out a plan (perhaps just a high level one) will greatly help you in deciding what to do when reality surprise you. Five minutes well spent on planning may save a lot of on-the-fly decision time and lost opportunities.

    Again, thanks for the article.

  5. says

    Another great post,

    I tend to be a planner, however like you were saying sometimes unforeseen issues come into play.

    Being new to freelancing this post has come along at the right time. Having a plan B, being open to others opinions and not stressing what I can’t control are good things to know in the early stages of my freelancing career/lifestyle.

    Thanks Again for the post

  6. says

    The plan’s purpose is not to outline the exact path that should be followed. When things don’t go as planned, I don’t see it as my plan has failed.
    The most important benefit of planning is that you are forced to find answers to questions that arise during the planning process, find “bottlenecks” that you may not have thought about, and just be more prepared to what is coming.
    If you fail to plan, you plan to fail!

  7. says

    I believe that I am a hybrid of the two.

    I like to work by the “seat of my pants” most days, crafting topic ideas as I go along. This means that if something is happening that is breaking news, then I can cover it on one of my automotive blogs right away.

    But I also plan. I keep a reporter’s pad with me and mark it up each week with what assignments I want to get done on a daily basis. Essentially, it is an X-Y chart where X represents the customer, website or blog I’m writing for and Y represents the day of the week. As I go through the week, I use tick marks to show my finished work, adding up my daily totals and weekly sum at the end of business on Friday (or Saturday morning).

    Disruptions are part of the game which means we all need to learn to adjust to them as they occur. By planning and by being flexible, the freelance writer should find that his or her work brings satisfaction and is more profitable too.

  8. says


    I’m also a planner (and a stressor). I like to give myself lots of extra time for “in case”, but, one thing that I have realized is that it is very important to plan for the breaks too. Without that downtime and enjoyment, planning and work is going to suffer.


  9. LisaT says

    Without a doubt, I am a planner. I previously worked at a place that operated on a “seat-of-your-pants” philosophy and one of the results was that they lost money hand over fist. I’m not saying that the lack of planning alone lead to poor business practices, but it certainly did not help.

    Curiously, I’ve found that it’s always easier to layer additional, spontaneous jobs/assignments/what-have-you into the mix when there is already some sort of plan or blueprint in place.


  10. says

    I like to plan ahead… and I like to have a working plan BUT I always need a back up plan. Although I would just love to dive in head first I have put the leash on my tendency to rush and create a calendar for the work ahead. Creating illustrations for picture books requires several levels of planning.

    That is Plan A.

    Because I am a digital artist I need a second back up plan. Plan B means that everything I create for an illustration is sketched beforehand, printed and saved. Finishes are printed and saved. Story boards are created and saved. So along with all the work in the computer I have hard copies in some form to use as a reference.

    (Before you criticize the use of paper, I do recycle, so there is little wasted paper. I even use the scraps that get cut from the edges of larger pieces.)

    Plan C is to get all sketches or finishes saved as small lo res jpegs and uploaded to a private website for the editor to view.


    If you rely on your computer for your freelance work you will know at once.

    Because we are subject to power outages and some of them are long term a computer can be useless. Last Dec we experienced 12 days with no power because of the New England Ice storm. Our area is mountainous and was very hard hit. When my editor called for progress reports I did have them at hand …. printed hard copies were ready for critique and discussion. Because plan C was in action… all the images had been uploaded to a website prior to the storm… my editor could view them online (she had power) and I could make notes on my hard copies.

  11. says

    I find that I like to change my plans so I’ve started to look at some mapping planning tools. I’ve been using Inspiration and MindManager which let you lay out projects in a free-form diagram, like you have at the top of your article. I also use them to plan out reports and other documents. I like them because they let me brainstorm ideas onto a screen and then rearrange them as I go. MindManager is overkill for me, so I am leaning towards Inspiration, but they are both worth a look if you like to see things visually or like to rearrange your plans on the fly.

  12. says

    I plan in different stages:

    1. Mindmapping on paper or with MindMeister to clarify what’s ahead
    2. Set up Projects broken down in ToDo’s in Things

    Things really helps me to not forget tasks, also personal ones like paying bills on time. The only thing missing is a calender view of those tasks to make planning along a time line is easier. I do that on paper.. I love the weekly planner from Moleskin and I have a big cork thingy where I pin my todos for the week.

  13. Gökhan Doğan says

    I’m using two tools for planning always. Outlook and freemind.
    Remember the milk can be considered as an alternative
    Plan B should be absolutely. I sometimes do not.
    That is when I’m having trouble

  14. says

    Of late, I fell off updating on my blog and stopped planning for my blog writing. Partly… I got busy working for clients on consulting and got my time eaten up coordinating with the folks.
    Frankly, I’m seat of the pant guy but inherently I would like things to be planned. But lack execution. However, I’m a stickler for deadlines with my clients. I do deliver before they actually ask it. The reason, I write quickly and get it done fast – the first draft. And it takes couple of editions to get the final bright one!

    thanks for the post and the reminder… I’ll try to be a planner form now!

  15. Anon says

    This post topic has potential but is really light on the content. Go more in depth on your suggestions, ie offer tools or methodologies to help freelancers get in line with planning strategies.

    What’s funny is that this post is little more than an outline that was never quite fleshed out; a fly-by-the-seat type of person may have contributed something worth reading.

  16. says

    according to this post,
    I’m a seat of the pants freelancer,

    I think it made me suffer for long time,

    I’ll do my best to be a planner,

    thanks Laura for the great article

  17. says

    I find that if I don’t plan something out then I don’t really have an idea of how long it will take to accomplish and its a bit like working in the dark. Its great to make plans as long as they’re realistic and as long as you keep to them too.

  18. says

    I work from home so I need to plan my time without a plan I would just easily get distracted. Sometimes it does remind me of being at school and when the bell rang you went to your next class, I suppose for me things haven’t really changed that much. I enjoy setting a schedule for my day. I do have a back up plan and a back back up plan just to be on the safe side.

  19. says

    I’m very much a fly by the seat of my pants individual, but trying to get the most of my day that way can be really hard. I’ve found a compromise where I make sure I’ve always got a to-do list with me or at least bullet points and refrences to on going projects. Sometimes it’s not the plan I need to the reminder that I have things to do, and project piling up if I don’t get through them.

    Thanks for the post

  20. says

    Another great article from Laura.

    I recently mentioned in a post on my site called “The Freelancers Secret” that “Fail to plan, plan to fail”.

    Yes, natasha got there first with that proverb in the comments above, however, it ought to be repeated!

    Thanks again for the awesome article.

  21. says

    I’m a planner and have a knack of predicting outcomes and forseeing pitfalls. I guess this comes with experience though.

    “Without a desination to a ship no wind is the right wind!”

    A plan, goal and structured approach will help to avoid the typical last minute rush where things are shabbily cobbled together and fall apart a few weeks later.

    Good planning will reduce the long term effort. Failing to take the time to plan will generally end up with you being frustrated and annoyed.


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