Goal Setting & Project Planning Guide
Goal Setting & Project Planning Guide
You’ve got a big idea inside of you; a goal you want to achieve, a project you want to
see completed. Maybe you’ve tried to make it happen in the past and it didn’t work
out, or maybe you’ve been stuck in the same phase for so long and don’t know how
to get past that hurdle, or maybe you’ve stopped and started so many times that
you’re not really sure what the main objective even is anymore.
For whatever reason, that big goal is just not happening for you.
This workbook is a short, very to-the-point guide for how to achieve your goals. Any
goal. You want to be president? You want a billion dollars? You want a private jet?
Let’s sit down together and plan out how you’re going to achieve that.
This workbook will help you lay out everything – from your resources, to your
knowledge gaps, to your obstacles – so that you have concrete steps towards
success. Simply read the chapters and do the exercises in the worksheets at the end
of the booklet. This is a pdf, so you will be able to print multiples of the same page if
necessary.
In the spirit of brevity, we’re going to jump right in. Good luck!
Celebrating Success.................................................................................................................... 9
Obstacles ..................................................................................................................................10
Worksheets ..................................................................................................................... 21
There are dozens of ways to formulate a goal and there is simply no way to cover all
of them in this booklet. In my experience, the SMART strategy is the most useful for
clarifying the purpose of your goal and identifying potential problems from the outset,
so that’s what we’ll cover here.
• S = Specific:
The objective should be crystal clear. Statements like ‘I want to be rich’ or ‘I want a
family’ are extremely vague. If you are vague with your goal, then you will have no
way of knowing when you’ve succeeded. What does ‘rich’ mean to you? Does
‘family’ include cousins? Uncles? Friends who are very close to you?
Even statements like ‘I want to feel comfortable’ can be vague. Not only because of
things like lifestyle inflation, which can affect what a person considers ‘comfortable’
as they make more and more money, but also because ‘feel’ is such an imprecise
verb.
To make a goal specific, start by identifying your most basic objective. Then look at
each word and ask yourself: ‘What do I mean by this?’
Go through the statement until you’ve drilled down to the most specific meanings of
the words that you can think of. If possible, show your goal to an accountability
partner and ask them to read it. If they have any questions about the goal itself, then
you’re not being specific enough.
Also, it helps to express your goal as a positive statement; make it something you
want to do, rather than something you don’t want to do. ‘Complete this freelance
milestone’ is a better goal than ‘Don’t be late on this milestone!’
• M = Measurable:
If possible, make sure that there is some sort of deliverable. A project that you’re
going to complete. If your goal is to become an interior designer, then the
measurability could be in the number of finished rooms in your portfolio. If your goal
is to become a musician, then a measurable outcome could be a number of gigs per
month. Connecting your goal with a deliverable will give you a tangible goal to strive
towards.
One of the hardest things for some people to do is accept when a project is finished.
Maybe you’re prone to telling yourself, ‘Yes, technically this is finished, but if I just do
this to it, then it will be better!’ Especially in the creative field, people can find it
difficult to call a project finished because there are always areas where they can
improve. These small improvements can help to a point, but there will come a time
when the effort put in will not be reflected in the outcome.
If you formulate your initial goal with a clear, measurable success point, then you will
be able to recognise when you are finished and stop yourself from lingering once the
goal is demonstrably complete.
• A = Attainable
Your goal should be formulated to accommodate the amount of effort that you’re
willing to put into it.
Attainable doesn’t just mean ‘is it possible’? It means: is it possible for me?
It helps to make sure that the goal is dependent on your own actions. If your goal is
to make a million dollars in the stock market, then you are largely dependent on the
actions of other traders for your success. You, personally, cannot keep the stock
market on an upward trajectory; likewise, you cannot personally prevent the market
from crashing and taking of all your money with it. If your goal is to get perfect
grades, then you are putting a lot of power in the hands of instructors (who might
grade on a curve, have specific requirements in mind for a task, etc) and your peers
(who might be working with you on group projects, or even just sharing their notes
with you).
You should have as much control as possible over the outcome of this goal because
it can be absolutely soul-crushing to have a goal that fails for reasons beyond your
control.
• R = Relevant
Relevance ought to be the starting point of any goal-setting activity. Basically, why?
Why do you want this? What do you hope to gain from this? How is this goal going to
help you? Why should you put time, energy, and resources into achieving this thing?
You need to make sure that the goal aligns with your values and long-term plans.
Some people are driven by logic and reason, while others are more emotionally-
driven, so what compels you will largely depend on what you value.
When establishing your Why, try to dig down to the root of it. You might start with ‘I
want to be rich because I want to feel comfortable’.
Ask yourself ‘Why’ again: ‘Why do I want to feel comfortable?’, ‘Because I’m afraid
that if money is too tight, then I will be one bad day away from poverty’.
Once you know your Why, you need to make sure that your goal will satisfy that
Why. If your goal is to become an Olympic diver, and your Why is ‘because I want
my father to respect me’, then you might need to re-evaluate whether that goal is the
best way to satisfy your Why.
• T = Timely
Without a time frame, you could end up puttering on this goal for decades. Give
yourself a specific deadline to work towards, not just because it’s an easy way to
help measure your success (‘I will perform x task before y occurs’) but it also
ensures that you do not dawdle on your task.
A deadline should compel you and give you a small sense of urgency. Obviously, it
should be attainable and consider the difficulty of the goal. Please don’t formulate a
goal with such a tight deadline that you burn yourself out trying to get it done! In fact,
it can help a lot to build some wiggle-room into the goal formulation. Add a little extra
time to account for potential problems.
You will notice that a lot of these points bleed into each other; specificity comes up in
every segment, timeliness should coordinate with attainability and assists with
measurability, etc. That is why the SMART system is so effective in goal formulation
– because each step builds on the others, it ensures that you are not leaving gaps in
your plan.
Once you’ve considered each of the SMART segments, you should have a fairly
good idea of what your goal will look like in detail. Now, you should formulate one or
two sentences that you can write down and keep nearby. This will be your anchor
when you are formulating milestones, and it will help you avoid choosing actions and
tasks that don’t actually help you achieve your goal.
As you can see, some of these are quite detailed, while others are to-the-point.
Some include the how as well as the what. Once you’ve gone through the SMART
system, you can decide for yourself how long and complicated you want your gowl to
be.
Head to the [Worksheet 1] and fill in each of the segments. Do it in pencil, because
you’ll probably have to erase and adjust as you go.
Once you’ve filled in all of the segments, sleep on it. Then, come back and formulate
your one/two sentence SMART goal.
To begin, you need to break it down into milestones. Milestones are the little goals
that compound to help make up the big goal; the stairs you climb to reach the peak.
You need to formulate these milestones with the end goal in mind and make sure
that you’re not putting effort and time into something that is not going to help you.
The milestones are small-to-medium-sized goals. They usually take a couple of days
to a week to complete. We’ll split them into smaller tasks in the next chapter. For
now, we’ll begin with brainstorming.
You will need to find an example of what you think your goal will look like in its final
form. You are not the first person to want to do this – someone, somewhere has
either succeeded in achieving this goal before, or they’ve done something similar.
In some cases, you’ll get lucky and there will be books, articles, or short courses that
will explain what milestones usually go into a project similar to yours. If not, then
you’ll have to use your imagination.
In [Worksheet 2], write your SMART goal in the centre of the page. Put yourself in
the mind of whoever completed the example you found and write all of the
milestones you think they had to complete on their road to the finished project. The
milestones don’t need to be in order. If you think of anything that you will need to do
differently – like gather resources, identify potential obstacles, etc – then you should
add those as milestones as well. The example you found is a guide, not a gospel.
CELEBRATING SUCCESS
It’s important to celebrate your successes. It increases your motivation when you
take time away from the grind to enjoy something that makes you happy. A lot of
people will tell you to give yourself a very nice reward as you complete milestones. I
agree, but I will add: make sure that the reward will help you finish this project.
Often, when people say ‘Reward yourself’, it can be interpreted as ‘Treat yourself’. If
your goal is to become a vegetarian, a reward could be eating something that you’ve
been denying yourself – but that reward is actually a step backwards.
When you’re playing video games and you go up a level, you’re rewarded with
experience points or new equipment. The rewards are usually directly or indirectly
tied to the next stage of the game. You will need those points or those weapons to
accomplish the next tasks. You’re not sent back to the same point you were when
you started.
In [Worksheet 3], you’ll see a section where you can fill in what rewards system you
will be using for each milestone. Feel free to get creative. If you have an idea of the
order that the milestones should be in, make sure you take that into account and
plan rewards that could help you achieve the next milestone.
Take a look at your example project again. Ask yourself what could have stopped
them from finishing. Maybe there’s a way to research what has stopped people from
finishing project like this in the past. You’ll likely be able to find plenty of resources
about what not to do using a quick Google search.
Look at your personal life. If your project will require a lot of time, what could stop
you from putting the time in? Check your obligations. Imagine the worst possible
things that could happen and use [Worksheet 4] to make a plan for what to do if
those things occur. Be sure to have a list of potential resources that you can use to
offset obstacles, as well as a handful of plans ready to implement if one of your
predicted obstacles come up. You’d be surprised how many basic plans can be
adapted to different issues.
I would recommend that you consider a ‘task’ to be anything you can do in less than
two hours.
Just like earlier, you should imagine yourself actually completing each milestone
from start to finish. What does that look like? Imagine what specific tasks you would
have to do and write them down in the [Worksheet 5]. Write down everything you
can think of, no matter how small. You can always erase things later.
Imagine that you’re building a cabinet. You have a toolbox and equipment ready.
You take out the hammer and nail two pieces of wood together. Then, you put the
hammer back in your toolbox and use a wood plane to carve down the side of one of
the pieces. Then, you put the wood plane away and use a saw to cut another piece
of wood in half. Then, you put the saw away and use the hammer to nail another two
pieces together.
This will get exhausting and confusing very quickly. However, if you identify what
tasks will require similar tools, then you can do those together and avoid the fatigue
that comes with constantly switching between skill sets. This is task batching.
Regardless of your goal, categorising and batching tasks will help you move through
them quickly and easily.
There are many ways to categorise and batch tasks. In this guide, we’re going to
cover two.
The Spoon Theory is used to describe the amount of mental or physical energy a
person has available in one day. Christine Miserandino developed the theory to help
articulate how it feels to be chronically ill. She used spoons as visual representations
of units of energy. She explained that many people with chronic illness wake up in
the morning with a set number of spoons, with each spoon representing a task that
needs to be done. Things like brushing hair, making breakfast, and going for a walk
all take a spoon. If a chronically ill person runs out of spoons by the end of the day,
then they will be unable to finish any other tasks until their spoons are replenished.
Importantly, the number of spoons is not consistent. For the chronically ill, some
days are better than others.
This is a very useful metaphor. Even if you are not chronically ill and your energy
levels are generally fairly consistent, it is likely that you will recognise the feeling of
knowing that a particular task will cost you a lot of mental or physical energy. Spoons
are a useful way to categorise those tasks.
When you read through your tasks, how many spoons might you assign to them?
There may be some tasks that other people would consider quite simple, but for you
they represent a significant amount of mental energy. For example, talking on the
phone drains my spoons faster than anything else, and if possible I will always avoid
talking on the phone if I haven’t had the chance to prepare in advance. But I can
answer emails with barely a thought. If I have a lot of emails to answer, I would do
them all together, but if I have a lot of phone calls then I would need to space them
out over several days so that my spoons are reserved.
You should do some reflection to decide how many spoons each of the tasks in your
list will cost you. You can use that to batch your tasks and make your schedule.
When you fill in [Worksheet 6], you should try to guess how much time/spoons each
task would take, as well as identify the skills that you will need to complete them.
There is also a section in the worksheet for the priority level. If something is urgent or
necessary before any of the other tasks can be completed, then it would be Priority 1
and you should probably do that first regardless of batching. If the tasks are lower
priority, then you can schedule those later.
Outsourcing it involves finding someone else to help you – either by guiding you
through the process, or by taking over the task and completing it on your behalf. It is
very common for companies to outsource tasks that require very specific skills to
freelancers or contractors, but it is possible for a private citizen to hire a freelancer if
their skills are lacking. There are sites like Upwork and Fiverr where you can hire
freelancers. You will need to assign resources (money) to these tasks.
Fudging it involves just… doing your best. If the task is small or low priority then you
could probably get away with doing the bare minimum to get it completed, and then
moving onto something that is more in your wheelhouse. It might not be perfect, but
it will be done.
Filling it involves learning the skill that you’re lacking. We luckily live in an age where
learning new skills is quite accessible (with some obvious exceptions – brain
surgery, for example, isn’t something you should learn from YouTube). If you know
that this knowledge gap will come up frequently, or if this is a skill that is absolutely
No matter how you decide to fill the knowledge gaps, it helps to sit down at the
beginning of each milestone and plan out which tasks are likely to be problematic. If
a task is too difficult, it might even lead to you procrastinating certain things because
the effort it will take is untenable. Plan at the outset how you are going to address
these gaps and you will not freeze up later.
MAKE A SCHEDULE
As discussed previously, a deadline is incredibly useful. You had to come up with a
deadline for your SMART goal. Now, you need to make sure that you can actually do
the milestones in the time that you’ve given yourself.
When you filled in [Worksheet 6], you estimated the time that it would take to do
each task. Even if you didn’t use the timing to batch your tasks, you should still be
able to use it to figure out a potential timeline for the milestone. Use [Worksheet 7] to
figure this out. Is that timeline going to fit into the goal’s deadline? If not, that is an
obstacle to success and you will need to come up with a new plan.
Once you know how much time each task will take, you need to make time to get
those tasks done. At the end of this booklet, there’s a daily schedule, a weekly
schedule, and a monthly schedule. Feel free to use these and plan around your
other obligations so that you can complete each task in a timely manner. Remember
to schedule work thoughtfully – if you’re just getting back from the gym and you’re
exhausted, that may not be the best time to do something that requires a lot of
spoons.
You might have noticed that there is an emotion tracker among the worksheets at
the end of this booklet as well. You can choose to use as you work towards your
goal. If you’re not feeling good – if you’re burning out, or stressed, or just feeling
apathetic – then it’s a good idea to schedule yourself a nice long break from the
work. If you can’t schedule a full break from the work, then you might consider
focusing on the lower priority tasks or the tasks that require fewer spoons, at least to
Remember that this plan is adjustable. You’re not beholden to it. You may have to go
back and re-evaluate your milestones once you’re a little way into the project. You
might even have to add new milestones and tasks as you become more familiar with
the scope of the project. That’s ok. It’s important that if this comes up that you set
aside time in your schedule to re-plan and reframe.
Just make sure that you have your SMART goal nearby, and your Why at the top of
mind, so that you can make adjustments with both of those things in mind.
WORKING CONSISTENTLY
This is a big project. You’re going to need to work on it consistently for a while, and
that’s a skill that isn’t very common. Working consistently is a muscle that can be
developed with training and practice. Here are some ways that you can develop your
working muscle as you’re working towards your goals
1) Trust the systems. You’ve put a lot of time into understanding how much effort
each milestone will take, and you’ve made sure to arrange your schedule to
accommodate your estimates. Your past self may have been off on a few
calculations, but it is easy to adjust for that since they also built in extra time
to account for delays. Follow the plan they set out for you.
2) Try to enjoy the process. Like I said, this project will take time. You’re
probably going into this enamoured with the end-goal that you have in your
mind and you’re probably impatient to get there. But you will likely be much
more consistent in your work if you can enjoy the actual work and not just the
results that it will give you.
3) Figure out what motivates you. Earlier I talked about how rewards should be
tailored to the goal, if possible. That doesn’t mean that you can’t Pavlov’s Dog
yourself a little bit. If the thought of a pizza night will push you into finally
completing all those administrative tasks that you’ve been putting off, then it
AVOIDING BURNOUT
With big, long-term projects come the inevitable potential for burnout. Burnout, in
case you were unaware, is a special type of work-related stress that manifests as
physical or mental exhaustion, a sense of reduced accomplishment, and a loss of
personal identity. It’s a terrible thing to suffer from. Many of the strategies in this
guide – such as categorising tasks with spoons and the emotion tracker – are
designed to alleviate the stress that can lead to burnout. Here are some other
strategies:
1) Use the emotion tracker. If you see a consistent feeling of apathy or sadness
on the tracker, that is your sign to check in and slow down. If you can stop
burnout before it starts, you’ll be in a much better position than someone who
has to fight their way through already suffering from it.
2) Schedule regular breaks – and make sure that they are actual breaks. Earlier,
I mentioned how smaller, more manageable tasks can be helpful to fit in
around the bigger ones to give your mind a rest. But if you’re burning out, it
can help to just take a break from the project altogether. Try to be mindful and
avoid turning this into procrastination, because if there are bad feelings
associated with a project then it can be very hard to return to once you’ve
stopped.
3) Go back and see what tasks can be outsourced or discarded and still allow for
the project to be completed. Is there anything you don’t have to do? Then
don’t do those things. Cut those parts from the project or allocate resources to
getting them done elsewhere. You don’t need that stress.
There are whole books dedicated to burnout and how to avoid/treat it. I suggest that,
if you can’t avoid it, you take advantage of the many resources available to you.
Consider who the stakeholders are in the project you’re working on (if you have a
boss, supervisor, or partner, etc) and make sure that they are aware of the situation.
Maybe they have resources that can help you. Make sure that you visit your doctor
to take care of your physical health and, if you can, book a meeting with a therapist
to get your mental health on track.
Remember that achieving your goal is only useful if you can enjoy it. Burning out
makes it very difficult for a person to enjoy anything. Way up the costs and benefits
of the situation and reflect on what will be better for you in the long term. It’s ok to
decide that a project isn’t worth the cost.
WHEN TO LET IT GO
Sometimes, no matter how hard we work on something, it just doesn’t happen for us.
As Captain Picard once said, ‘It is possible to commit no mistakes and still lose. That
is not a weakness; that is life.’
There’s a common belief that there is nothing in the world that you can’t get if you
put your mind to it. That you can make any dream a reality. I think that there’s a
measure of truth to this – I wouldn’t have written this guide otherwise – but I also
think that pursuing a dream or goal beyond the limits of your own physical and
mental capacity is damaging. Being able to adjust your goal, or even just let it go,
can be a very difficult skill to learn.
If you’re wondering if you should pivot on the project you’ve been pursuing, ask
yourself these questions:
1) Has my Why has changed? Maybe this project is feeling stale because you’re
no longer satisfying a Compelling Why. Earlier in this guide, you worked
If you’ve decided to adjust the goal/project to accommodate your new feelings about
it, then I have good news! This guide will still be useful to you. Go back through your
notes on the process and try to find where the changes need to be made so that you
can still feel fulfilled with this project. If your why has changed, then you’ll need to
start back at the beginning, but sometimes it can be as simple as adjusting some of
your milestones or the scope of the deliverables.
If you’ve decided to let it go, then I have good news! You’re allowed to do that. Just
make sure that your stakeholders understand what has happened and why you can’t
continue. Offer to give your stakeholders the work that you have completed and the
plan you made so that they can continue without you. If you have no stakeholders,
all the better.
Also, you’re allowed to take the time to mourn. To have a goal or a dream is to have
a vision of a future version of yourself. Giving up on that means giving up on that
future vision. Be realistic about what you’re giving up – instead of focusing on the
romanticised version of the completed project, be honest about what that project
actually would have meant for you. This might help assuage some of the guilt.
Finally, once you’ve decided to move on, move on. Don’t linger in your feelings.
Don’t let yourself get bogged down in this. You’ve learned the skills of understanding
why this project didn’t work, and that will help you formulate stronger and more
successful projects in the future. If you stay bogged down in this project then you will
carry that feeling into the next one, poisoning it with a negative mindset before
you’ve even begun. Try to enter the next project with the same enthusiasm that you
had at the beginning of this one.