Always Have a Plan

This might be my favorite topic to cover. Not because it’s the most important but because it’s one of the things I feel most passionate about. It’s something that is ingrained deep in my being.

Growing up the one thing my dad said like a broken record was “always have a plan”. Whether it was housework, running errands, yard work – really anything at all – his advice always remained the same. Always have a plan. When something went wrong, he always made a point to ask “what was your plan” and “what did you think was going to happen”.

It makes perfect sense. You wouldn’t build a house without a blueprint. You wouldn’t teach a kindergarten class without a lesson plan. You wouldn’t travel across the country without a map (maybe you would but I’m not a big fan of getting lost).

Without a destination in mind, you really have no idea of gauging where you’re going and how far you’ve come. This makes getting there much more difficult. Quick and easy can turn into detours and shortcuts which take you in all the wrong directions.

Having a plan is more than just putting a bunch of words on paper. It’s figuring out how all your actions ladder up to your end goal. It’s understanding what you need to do step-by-step to get from point A to point B.

I want to first start by defining the word plan:

  • (noun) a detailed proposal for doing or achieving something
  • (noun) an intention or decision about what one is going to do
  • (verb) decide on and arrange in advance

The keywords here are detailed, achieving, intention and advance.

I am going to cover a few different areas of your life where you should always have a plan.

The first is your career:

Every successful business model is full of plans. Some examples include timelines, seating charts, blueprints, financial projects and that doesn’t even touch the surface of all the plans that are made in the business world. Without a plan you have no sense of direction – you are blind.

When it comes to your career it’s just as important to have a plan. I won’t sit here and tell you that you need to be incredibly specific and know what you want to be doing every minute of your day ten years from now, but you should have (or try to get) a good idea of what you would like your life to be like.

Having a plan allows you to jump on opportunities. For example, if a client you work with quits and had the job you want, you can quickly throw your name in the hat. If you didn’t set up your goals ahead of time you might have missed a major opportunity (see my post on exploring every opportunity here).

Your plan should be more than just an idea of “what you want to be when you grow up”. It should be a detailed outline of who you would like to use as a mentor, organizations you need to join, what education you need, what experience would lend itself well to your future role, what companies you might want to work for and what you feel your overall career trajectory is. Having an abundance of direction, resources and, contacts is never a bad thing.

When I sat down to figure out my career plan, the one thing that helped me was removing all limitations. If I could be… if I could do…ANYTHING I WANTED TO – where what would I do? As soon as I removed the “maybe you could do this” and “if I had better experience I could” and just let myself daydream the answer was clear. Not just clear but crystal clear. I want to be a creative director. I want to guide others to the big ideas that I love developing. I want to teach others how to come up with strategic, well thought out ideas that break through the clutter and energize the advertising world as we know it. I want to teach others how to make the impossible possible. How to have faith in their ideas. How to take a “what if” and dress it up into a presentation a client can’t say no to. You must let your mind wander to get there. You can’t restrict yourself. You must allow yourself to think big. You must allow yourself to dream. There are no restrictions on where your career is going to take you. The only restrictions are the ones you are putting on yourself.

If you sit down to think about where you want to go in your career, and you have a million different ideas – try narrowing it down to a more manageable number. Ten to fifteen is a good place to start. Then for each job you think you might want to try – find someone who is already doing that job and set up a time to meet with or shadow them.

Sometimes you think you might want to do something until you see what that job truly entails. Ask them to share how they got to their current position and think about how you would feel taking each of the same steps that they took.

Next is for individual projects:

Having an overall plan for your career is your big picture, but on a day-to-day basis you need to have plans that help you achieve your small goals.

When you start a project, it’s imperative that you sit down with your team and align on:

  • Timing
  • Expectations
  • Roles and responsibilities
  • Performance metrics
  • End goal

Having a firm plan for every project allows you to push back when you are off track and it helps hold the entire team accountable. It will make the entire process go so much smoother. Collaborating will be easier. You will have less disagreements which typically lead to stopping and starting and stopping and starting. All of this will make you and your team more efficient.

Last but not least, for your own life:

How do you figure it all out and make everything in your life live up to your plan? You must constantly be reviewing your plan and never let it out of your sight.

I know everyone’s situation is different but as a working mom, it’s so easy to get off track because I feel overwhelmed and don’t have a plan.

I live and die by my planner. I have since I was about 12. I feed off of to-do lists and chaos makes me anxious.

At the beginning of every year get out a calendar. This is one of my favorite things in the entire world – picking out the perfect planner, pens, sticky notes and such. I make sure I am enjoying the planning process and not making it a stressful activity that makes me feel pressure to get stuff done.

First, I block off all the important stuff that makes up your life. The stuff you are expected to do that you can’t really get out of. Most of it is stuff I wish I didn’t have to do but I do (doctor’s appointments, auto service, that kind of stuff).

Now, put those big dreams down on paper. Guess what… you are expected to do these items and you can’t get out of them. If you don’t get your car serviced it won’t work. If you don’t attend to your goals, they won’t happen.

Now at the beginning of each month – do it again. On a weekly basis – you guessed it – do it again. When you wake up in the morning – if you haven’t caught on by now – do it again.

It might be hard to find the time to make your schedule but I promise you that it will keep you on track.

Figure out what you need to do to ensure that you are meeting your goals and reward yourself when you do.

You must learn how to master time management if you want to be successful. The most successful, powerful and influential people all do it.

Here is an outline of some of the big things that I add to my calendar to keep my life in order and ensure that I don’t have to move appointments or give myself any excuse to opt-out of goal driving momentum:


Tip: When I do my calendar for the year, I use my calendar from the year before to pull over the dates so that I’m not searching for them every year.

  • Goals – Major Milestones I Need to Hit
  • Holidays
  • Birthdays
  • Anniversaries
  • Health appointments
  • Hair appointments
  • Vacations
  • Time to learn
  • Time to plan for next year


  • Childcare
  • Goals – Major Milestones I Need to Hit
  • Meetings (don’t take or make meetings that are unnecessary, and meetings don’t have to be set in 30-minute blocks – a meeting can be set for 15 minutes).
  • Project due dates
  • Time to plan for next month


  • Goals – Major Milestones I Need to Hit
  • Phone calls I need to make
  • Meetings
  • Key deliverables for the day
  • Meal plans
  • Exercise plans
  • Time to plan for tomorrow

Happy Planning!

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