I didn’t jump out of bed on January 1st 2019 excited to face a new year. It was mid afternoon when I decided I was putting off the new year for a few more days.

“My new year starts on the 3rd” I told my wife.

… it started on the 4th, and the stress hit the next day.

I was sitting at my computer trying to wade through a pile of emails and tasks that I had secretly promised myself I would finish over the holidays with ‘all my free time’. After an hour I reached that place where my brain just said … nope… and any idea of work stopped.

I needed to step back and get organized. I needed a plan.

First of all, let’s talk about what a plan is (and what it isn’t)

I am not a born planner. For many years I believed that any kind of plan would stop me from being spontaneous and living in the moment.

What’s made me a convert is that I learnt that a plan is not a strict schedule that I must adhere to, but an exercise in which I use my imagination to sketch a version of the future which helps me answer one question: what should I do next?

This is true whether you’re making a plan for the day, the week, or for 2019. The point isn’t to make all your decisions for the next 12 months, but to collect all the stuff you know for sure, you think might happen, and that you really want to happen in front of you so you can figure out your first step.

The exercise of planning is one of stretching the scope of your attention

After waking up with a tension headache I decided to do a gentle stretch session. Shit. It was intense. I was so tight, that every bendy direction given to me by the woman on the youtube was complete mockery.

“Just sit upright and walk your fingertips to your feet.”

… and I attempted to sit upright while my muscles trembled with the intensity of the stretch.

If you’re not a planner, trying to imagine the entire year or even the next month might feel a bit like that.

That’s cool. Planning is an exercise and slowly over time you’ll find that you’re able to stretch your attention further into the future.

Pick a time frame that doesn’t fill you with panic. Imagine a year, a month, a week, the next two days and wait until your brain doesn’t totally freak out.

That’s your time frame.

Sketching out your plan

There’s no wrong way to plan. Well… there probably are wrong ways to plan, but there are lots of ways to get the job done.

Just remember that the point is to help clear up whatever question you have in the moment.
One of the big questions that lots of folks (myself included) have is what can I afford? Can I afford to spend three hours a week working out? Can I afford to take two weeks off in May? Can I afford to go out for lunch today (both in time and money)? Can I afford to get a new place this year?

These questions are especially difficult for variable income earners who have a limited idea of how much time and money they’ll have over the next year.

So here’s how to start laying it down.

The important questions to look at are:

1. What do I know for sure?
2. What can I reasonably guess?
3. What do I really want to happen?

We’re going to take a look at a few examples of how to play around with this. Remember… it’s play, it’s imagination, it’s not going to happen this way… but it could… and it’ll help us with the actual problem that we’re facing in the moment.

Plan #1: Figuring out the week

Question: Do I have the time for ________________?

This was a big problem for me at the beginning of last year. I kept over-committing to stuff and then things would get backed up and I would be stressed. I needed a plan, but I had never really blocked my time out in a systematic way before.

I used Google Calendars because I love being able to colour code blocks of time and it’s really easy to move things around. I can set it one way on Monday, and then shift things as the week goes along. The thing that really helps is that even though I’m moving things around, I’m really connected to the fact that if I move something… it has to bump something else.

To make my week plan I follow the same routine.

First, I block what I know for sure: appointments made, time I want to make sure to take off (evenings or mornings… booking rest time first is another skill I’ve learned this year), you can even put in sleep and meal time to make sure you’re accounting for that.

Next, put in the stuff you’re pretty sure will happen. It might not be confirmed, but you want to make sure to hold time for it. This is a combination of stuff that you want to have happen and stuff that you know happens every week. You need to shop, do laundry, and maybe shower… when is that going to happen?

And lastly, what do you have left for the stuff you want to do. This might be work projects or social stuff.

The thing I love about laying it all out on a dashboard is that I see all the things that are bouncing around in my head, and I can figure out really quickly whether I’ve overcommitted or if what I have planned is realistic.

A note: this might seem really overwhelming to some of you. You don’t have to do this every week. Remember…. a plan is a response to a question or tension in your life. Use it when you need to use it, but the more thorough your process, the more it will help.

Plan #2 Figuring out the next few months

Question: Can I afford __________________?

The same kind of planning can be applied to your finances. Yes, it’s hard to do when you’re a variable income earner and especially for those of you who have multiple income streams, but it doesn’t mean that you can’t patch together some kind of plan.

The list of questions is the same, and you can use this handy dandy tool to play around with them. It’s a variable income spreadsheet that helps you look at the next few months of your life (up to a year) in order to figure out if you’re spending too much or earning enough.

You can snag your own copy to play around with here, and the video below will let you know how it works. 

Plan #3 Figuring the year

Question: Can I take a two week vacation in ____________?

I love this exercise (which I stole from a mentor of mine) especially for the self-employed. It involves looking at the whole year and blocking out your vacation FIRST. And I’m not talking about the kind of vacation where you bring your laptop to a new city and then never leave the hotel room because you’re working the whole time. I’m talking about real vacation.

Here’s mine so far. I’m still working on it, but since I’m doing a lot of travelling this year it was really valuable to plan out days to adjust to the jet lag and block off real planned vacation.

Once I had this information I could look at the days I had left and math out the amount that I needed to earn per month in those days. Once I found a balance that seemed realistic I could feel better about starting to make plans for these vacation weeks.

Now all I have to learn is how to actually relax while on vacation. Sigh.

Plan #4 Figuring out the next 5 years

Question: Should I be saving? What for?

Okay. This one for you planning pros who want to stretch yourselves a little bit. It’s a technique that is stolen from the book Designing your Life (which is awesome and totally worth a read).

You can use it to map out your month or your year, but it’s really effective when you’re looking at a larger block of time.

They encourage you to draw out the next five years. What do you know? What do you want? What milestones do you expect to achieve?

But don’t just do one version… do THREE. One for the life you’re living right now, one for a version of your life that you would turn to if you couldn’t do what you’re doing right now, and one for a life that you would love to try if you knew for sure that no one would laugh at you.

Here’s one of their examples.

I went through this exercise late in 2018 and found it a difficult and rewarding thing to do, especially the second two versions. I found myself drawing a future where I was a 100% stay at home dad and one in which I was a cartoonist.

Both of those potential futures have become a part of my 2019 planning… which is pretty cool.

Don’t get lost in the weeds. No one knows what’s going to happen.

If successful planning was perfectly predicting the future there wouldn’t be a successful plan anywhere in the universe.

Planning is a game, an exercise of the imagination and a tool to help you figure out what to do next.

This year don’t get too bogged down in the product. Get your hands dirty in the process. Draw a picture, colour out some time blocks, and spend the imaginary cash of your future self.

And then make your next step a little more confidently.

Want to start getting control of your money? How can I help?