Clever Cactus Guide Goal Setting How To

Goal Setting: A Clever Cactus Guide

“It takes as much energy to wish as it does to plan.”

Eleanor Roosevelt

I feel like I’ve had goals my whole life. Only I used to call them “my dreams” or “what I’ll do when I’m older” or “this vague sense that I should do X because of Reasons”. I chased these elusive dreams down the best way I knew how – by bouncing between them like a pinball on a winning streak. Only I wasn’t winning. If anything, I was flailing about and starting projects I’d never finish, with very little to show for my efforts.

It was only once I started digging into goal-setting theory, productivity “hacks” and other organizational systems that I realized what I had were, actually and always, Big Goals. Simply naming that invisible force constantly propelling me forward made all the difference. Understanding why goals are so important in my life (which I detail in this post) inspired me to, well, do better. I tried out different goal-setting guides, day planners, agendas, apps, the works, to develop the system I use today.

Read on to find out how I set my goals up for success.

A Setting Goals Guide

Step 1 – Name your Goal

There’s power in a name. In fact, in that earlier post I mentioned above, I reference a study by Dr. Gail Matthews that showed writing down a goal makes you more likely to succeed. The more specific you can be about your goals, the better.

In her article “The importance, Benefits, and Value of Goal Setting”, Leslie Riopel MSc shares Edward Locke and Gary Latham’s five goal-setting principles and professor Fred Lunenburg’s goal criteria. The five Goal-Setting Principles are clarity, challenge, commitment, feedback and task complexity. Lunenburg’s goal criteria are specificity, attainability and acceptance.

I’ve read through a lot of goal-setting advice, including the criteria outlined by Locke, Latham and Lunenburg (the three Ls! Four if you include me!). Here are the four things you definitely need to know about naming your goal.


“Setting goals that are clear and specific eliminate the confusion that occurs when a goal is set in a more generic manner,” explains Riopel. Avoid vague statements like “write more”. What are you writing? How much is “more”? Instead, set a daily habit or a measurable “number”. For example: “write 500 words a day”, “write 2000 words a month”, “finish one chapter a month.”


I’ve mentioned this about new year’s resolutions, and it applies here, too – your goal should be something YOU want to do. “If we are continually given goals by other people, and we don’t truly accept them, we will most likely continue to fail,” Riopel writes. When you truly want to do something, you’re more likely to succeed than if you’re doing it just for appearance sake or out of obligation.


All goals should be a challenge. I personally don’t see the point in setting a goal if it ISN’T a challenge (but that could just be me). “Goals that are too simple may even cause us to give up,” Riopel explains. “Goals should be challenging enough to motivate us without causing us undue stress.”


Setting a goal that you can measure helps see your progress and gives you a confidence boost as you’re working on it. Measurable data includes daily habit tracking, counts (ex. words, exercise reps, weight lifted, time spent, etc), visual progress (appearance, painting completion, redecorated rooms, etc.) or any other form of measurable and trackable data.

Step 2 – Give it substance

Now that you’ve identified your goals and named them, it’s time to give them substance. There are two parts to this – first, a defining statement; and second, a vision board.

The Defining Statement

Write down WHY you’ve set these goals. How will achieving this goal change and improve your life? What aspect of your life are you working on with this goal? Personal? Professional? Physical? Emotional? You don’t HAVE to be specific here; this can be where you put statements like “be happier” (though I suggest adding “with X, Y, and Z”). All you need do is be honest with yourself.

The Vision Board

Find photos, quotes, memes, colours, song lyrics – anything that embodies the essence of your goal. If your goal is to plan a vacation, this might be pictures of where you’d like to go. Want to try restaurants every month? Print out menus or top 10 restaurant lists and add them in there. Anything that makes you want to achieve your goal that much more. (If you don’t want to make a physical collage, Pinterest is a great vision board tool.)

Post It

Put your statement and vision board someplace you’ll look at often. This could be the wall behind your computer, an image on your computer desktop, a page in your planner (like the goals pages in the Clever Cactus planner!) Make it huge! Make it small! Whatever will make it catch your eye and keep it in your mind all year long.

Here’s why you should give your goals some substance:
  1. You’ll hone in on the “what” and “why” of your goals before you start planning. Really get to the heart of why you want to do this. Explaining and visualizing it to yourself may even illuminate something about the goal you hadn’t consciously realized.
  2. There will be moments when your motivation wans as you work towards your goals. It’s inevitable. Anytime that happens, you’ll be able to look at what initially moved you to take this on and all the inspirational imagery you’ve collected will keep you going.

“The secret of getting ahead is getting started. The secret of getting started is breaking your complex, overwhelming tasks into small manageable tasks, then starting on the first one.”
– Mark Twain

Step 3 – Break it down

Now you’ve got this big, impressive goal (or goals). Are you excited? I usually am at this point! Thing is, I’m also usually pretty intimidated. Big Goals are daunting, like towering mountains whose peaks are hidden in the clouds. I won’t tell you “don’t be intimidated”, because it’s very much okay if you are. Be intimidated. Also, be excited. Imagine yourself up on the peak, taking in the breathtaking view of success!

Great mountain climbers know that you don’t climb the whole mountain all at once; you climb it part by part. You break the climb into sections, those sections into steps, and those steps into footholds and handholds. So that’s what we’re doing in step three – break those mountainous goals into manageable chunks.

Here’s how I break my goals down into the steps:
  1. Grab scrap paper, a page in your My Notes section, or open a new document on your computer.
  2. Write down everything you’ll need to do to accomplish your goal. Don’t worry about the order, we’ll sort things out later.
  3. Make note of what you don’t know. What you need to research – perhaps you’ve decided to start a business but don’t know what, exactly, you need to do!
    If you have time right at that moment, do some preliminary research.
  4. Add steps from your research to your list.
  5. Review the list and group things together by priority, urgency, task relationships, themes – any other patterns you might find. (As you’re building the list, you’ll see the patterns emerge).
  6. Rewrite (or reorganize, if you’re doing it digitally) the list grouped by priority/urgency first, followed by whatever other patterns you’ve made.
Clever Cactus Goal Guide Step 3
Example list for a vacation goal.

This list will be necessary in the next step and will be your road map for goal completion.

Step 4 – Add some dates

As you group your tasks in step 3, you might have already considered when you’d like to have the goal completed. Now it’s time to add that date to your goal! Most goals, especially those set during an Annual Review, are year-long objectives. That means the due date is December 31st. However, some goals, like the “go on vacation this year” goal have a mid-year due date. For this example, we’ll use August 4th.

This “due date” is what we’ll use to generate/create all the other dates in our plan. Hillary Kerr and Katherine Power, authors of The Career Code, say that the best way to achieve a goal is to figure out the end result and work backwards. Milestones are the building blocks to getting there. There are two ways to add milestone dates to your goal plan.

Method 1: All Dates, All the Time
  1. Put your due date at the top of your list from step 3.
  2. For each task, decide how long it will take. I like to give most tasks a week, just to allow myself some freedom.
  3. Work backwards, adding dates up your list until everything has a due date.

Note: Any dates you add during this step are dates you’re aiming for, but if you miss them, it’s okay. These are guidelines more than anything.

Method 2: Only Milestones get Dates
  1. Put a due date at the top of your list from step 3.
  2. For each group of tasks, decide how long it will take. I like to give task groups a month, three-months or six-month intervals.
  3. Work backwards, adding dates to each task group until every group has a date. These will be your milestones.
  4. I highly suggest you add a “check in” date at the following intervals: One month, three months, six months, nine months and 12 months.

The final step here is to add all these dates to whichever calendar you use the most. Maybe it’s your digital calendar, or the My Year section of your Clever Cactus (pages 14 – 18) or maybe a wall calendar. Whatever you look at the most, put your milestone dates in it.

Step 5 – Work on it

To really set yourself up for success, make a list of daily, weekly and monthly tasks. Add them to your agenda so that you don’t forget to do them. “Identify your specific, day-to-day actions”, Olympian Mark Richardson advises in his article “How to set big goals: lessons from an Olympic athlete”. “Process goals are the mini, day-by-day interventions you put into place in a relevant time-frame which is the foundation for success.”


Richardson sets up measurable activities for his training schedule, like drills and skills, repetitions, conscious diet monitoring, a good sleep schedule and pre-rehabilitation work. In the Clever Cactus system, I call these the “daily habits”, and track them on the Tracking page of each monthly section (first one appears on page 26).


Not every task needs to be done on a daily basis, but may benefit from a weekly frequency. The “Monday review” is one weekly task I highly recommend incorporating into your habitual life. During this review you’ll check your “Monthly” task list, review all your projects and make note of that week’s deadlines (maybe even checking ahead to ensure your time is scheduled well.) I also take this time to review my habit tracking progress.


If your daily tasks can’t really be tracked via a “done” or “not done” system, try keeping a career journal. In it, you would write – either every day or once a week – little updates on your goals progress, your accomplishments, what you need to work on, and anything else you want to track but is more cerebral than done/not done.

The one-sentence journal is one style I really like. Every day or week, write one sentence to describe what you accomplished for your goal. In the Clever Cactus planner, you could do this in the “Smiles & Thoughts” section of the “My Month In Review” pages (first one appears on page 28).

Work it

Now that you have a plan of attack, milestones to work towards, a list of daily and weekly tasks to keep you moving forward, and a way to track your accomplishments, it’s time for the fun part – working on your goal! Do your best to stick to the plan each and every day. Use your agenda or Clever Cactus planner to keep notes and check off tasks as you complete them.

Remember, weekly and daily activities should focus on that week and that day. Don’t worry too much about the big picture or where you are in your progress until Step 6. Time spent trying to analyze the big picture each and every day could be better spent chipping away at your goals!

Clever Cactus Guide Goal Setting - Monthly review
A (bad) visual representation of tasks moving from Monthly To Do list to Weekly Agenda.

Step 6 – Check your progress

This step is vital, in my opinion. Okay, I believe all the steps are vital… but often this step is the key to transforming a half-completed goal into a success story. So, even if you skip all the other steps in this guide, don’t skip this one. So what, exactly, do you do during this step?

Check in with your goals on every milestone date scheduled in Step 4! That being said, I prefer to check in on my progress once a month, rather than wait for the milestone intervals. I call it my “Monthly Review”. But if that’s too often for you, then the milestone dates are good too!

Here’s how I do my milestone checks (aka Monthly Reviews):
  1. Open up the notes you made in steps 1 through 3. For me, these are in my Clever Cactus planner, pages 4 through 22.
  2. Read over everything (and I do mean everything). Have any of your goals changed? Write that down!! (Plus the date it changed).
  3. Cross off everything that’s done on the goal task list you created in step 3.
  4. Adjust your task list based on your experiences so far (add to, remove, change tasks).
  5. Make note of all the tasks you need to do in the coming month; write them on the appropriate “To Do” list (month or week). I write these on the Monthly To Do list during the monthly review. Then, during my “Monday Review”, I decide if I have time that week to do said task.
  6. Repeat steps 5 and 6 for 12 months.

Monthly and Milestone check ins remind you that you’ve made progress. They boost your confidence, give you the big picture and let you assess your own strengths and weaknesses. They also give you a chance to look at the big picture, see what’s working and what’s not, and identify those troublesome areas in the following month.

Goal Change Examples

Goal: write 500 words a day.
Issue: you haven’t been able to meet that goal. Instead, you’ve been averaging 150 words a day.
Change: make your daily word count goal 200 – slightly higher than your average but more attainable.

Goal: Renovate the living room
Issue: Leak in bathroom, it needs to be repaired; can only afford one renovation.
Change: Renovate the bathroom (follow same schedule)

(Which is why all monthly spreads in the Clever Cactus planner have the Month in Review section with those exact section titles).

It’s so very easy to convince ourselves that we’ve made no progress, that we’re swimming against the current, or running in place. The truth is, we’re always making progress! Tiny steps are still steps! Step 6 lets you see that progress on the grander scale.

Step 7 – Celebrate success!

If you follow this guide, stick to the plan you set for yourself and keep working hard, you’ll have achieved your goal! At the end of the year, to really help you see all that you’ve accomplished, little and big, conduct an Annual Review (here’s the guide I wrote about those).

And you know what, even if you haven’t completed your goals or stuck to your plan – even if there are some steps left undone, or you gave up mid-year, or the goal didn’t turn out quite the way you’d hoped – you’ve done MORE than you did before! You’ve accomplished something! You’ve also learned something about yourself and made an effort to improve your life.

And that’s no small feat.

Every goal is a big goal

I created Clever Cactus on the theory that every goal is important. It feels a bit like the world puts pressure on us to have these ginormous dreams – to be entrepreneurs, to write the next best-selling novel, to make six-figures at our job … You get the picture.

Thing is, bigger isn’t always better. And not everyone wants to focus on creative or career stuff. A lot of people want to experiences. They want to live their life with a smile on their face and happiness in their hearts.

So-called smaller goals – regular chats with friends or family, treating yourself to something nice once a month, vowing to go to the spa for a massage more often, trying to eat less of the food that makes your stomach go “blarg” – these might sound less… I dunno, impressive? But they have a huge impact on our quality of life.

I hope you’ll use this guide to set yourself up for success when it comes to career, creative and convoluted goals. And I also hope you’ll use this guide to set yourself up for success when it comes to enriching your life with smaller, equally-as-rewarding lifestyle changes. Reach out in the comments below or via our contact page if you have any questions about setting goals and staying on track to achieve your dreams.

This one step – choosing a goal and sticking to it – changes everything.

Scott Reed
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