How to do an Annual Review

How to do an Annual Review: A Clever Cactus Guide

Since I started doing annual reviews, I’m happier, more confident, and better able to manage whatever life throws at me.

On Tuesday, I looked at why an annual review is important for everyone, not just employers and employees. I’ve been doing annual reviews for a few years now and I can say that they work really well for both my career-improving goals (like launching Clever Cactus) and my personal happiness goals (like keeping in touch with my friends).

While I’d like to say I’ve perfected the annual review, that’d be a lie. Every year, my annual review is just me, sitting at my desk, reviewing and planning with no real structure to the activity. Instead of trying to sort out what exactly I do during an annual review, I’ve consulted articles from other annual reviewers (see sources list at the bottom) to craft… The Clever Cactus Guide for an Annual Review.

Step 1: The Past

An annual review is a bit like the visitations Scrooge receives in A Christmas Carol. When the bell tolls one… ghost of Christmas past, etc. etc. Unfortunately, there’s no actual ghost to take you on a fun spirit-like journey. Instead, you have your agenda, journal, photos, calendar, emails, project management apps… all that fun stuff that’ll make you feel a bit like a ghostly presence sifting through your memories.

Read everything

The first step to any annual review is to read through all your stuff from the past year. Everything you have.

Here’s where keeping your Clever Cactus planner up to date each month comes in handy. The completed Month in Review sections will already have all the happy highlights listed.

Plus, the “what worked” and “what didn’t” sections are a great way to:

  • See how you progressed throughout the year; and
  • Create a shortlist of everything you might want to work on in the coming year.

Question everything

Once you’re done going through everything, you can then sit down to ask yourself a few probing questions. The answers to these questions will create a clear picture of your successes, failures, strengths and weaknesses.

I’ve compiled all the questions mentioned in Shen, Keiffenheim, MacKay and Mim’s articles, and put them in a single list to the right. These are starting points really.

You may find that the answers to these questions lead to more questions – that’s a good thing! It means you’re really narrowing down your focus to figure out what you need to do to improve your life and grow as a person. Follow those questions. Dive into the rabbit hole. Be Alice for a day.

(Right… we’re supposed to be Scrooge…)

Reflect on it

Take a look at your year as a big picture. Go through all those notes, answers, details and a whole whack of data to find all the patterns your life makes. Identify what motivates you and what holds you back.


Let’s say last year you were trying to foster a new habit, like doing yoga every day. When you go over your habit tracking data, you may find that you maintained your daily yoga schedule for the first week of every month and then it would become sporadic (yes, personal experience here). Take some time to think about why this might be.

Celebrate your progress and identify when, and why, your priorities shifted (if they did). Make a note of which tasks and projects fell by the wayside and explain why this happened.


In 2020 my three main goals for the year were as follows:

  • Launching Clever Cactus was my business goal.
  • Finishing 12 short stories was my creative goal.
  • Planning an overseas vacation was my personal goal.

Here’s the thing though – I’d also had a fourth goal, which was to finish writing the novel I’d started in November 2019. I abandoned that goal in March, 2020, because the novel was about a woman who survived a pandemic and well… It just wasn’t really the type of content I wanted to write about at the start of a pandemic. My personal goal to vacation overseas was also abandoned, for pretty much the same reason.

Projects and goals change as the year progresses. Sometimes, it’s outside forces that nudge us on a different path. Sometimes, we realize that the goal we’d set isn’t *quite* what we want anymore. Either way, that’s totally okay! No judgement is allowed during this step.

Tip! If you have a Clever Cactus planner, you can write your answers on page 19, “Thoughts on the Year”.

Annual Review Questions

I’ve compiled a list of questions from both what I ask myself during an annual review and from my research.

Must Ask
  • What went well?
  • What were the great, amazing, wonderful things that happened last year?
  • Of all the things you did last year, personal and professional, which are your three* biggest accomplishments? Why?
  • What didn’t go well?
  • What were the crappy, terrible, unfortunate things that happened last year?
  • Of all the things that you did last year, personal and professional, what are your three* biggest failures? Why?
  • What did you learn?
  • What have you learned about yourself? Your career? Your family? Your friends? The world?
  • If you could change one thing about what you did last year, what would it be?
Should Ask
  • How did you spend your time?
  • When at the office/work, how do you spend your time? Tasks/projects, meetings, sifting through calendars/spreadsheets?
  • What was the best investment of your time? The worst?
  • Is there any aspect of your day where your time management could be improved?
  • Did you challenge yourself?
  • What are two things you learned that you don’t want to forget?
  • Did you learn a new skill? If so, what helped you learn it? If not, why not?
  • What was the most challenging task/skill/part of last year? Why?
  • How have you grown and developed?
  • Are you happy?
  • Were you happy with what you were doing, personally and professionally?
  • Is there anything part of your life where, if you did less of it, you would be happier?
  • Is there any part of your life where, if you did more of it, you would be happier?
Could Ask
  • What are you feeling?
  • Describe your feelings for the past year.
  • When did you feel the most alive last year? The most loved?
  • How have you experienced crisis, loss and pain in the last year?
  • How are your habits, decisions and risks?
  • Have you developed any healthy habits you want to keep?
  • What was the best decision you made all year? What did you learn from it?
  • What risks did you take, and what were the rewards?
  • For which people in your life are you most grateful?
  • Which person has inspired you the most? How?
  • Which person had the biggest negative impact on your life? Why?
  • Are there any toxic friends in your life? How have you signaled your boundaries in the past year?
  • What new relationships enhanced your life? Who? How?
  • How has your relationship with yourself changed over the year?

Step 2: The Present

Now it’s time for my favourite A Christmas Carol spirit – the ghost of Christmas present (he’s so jolly!) This step is all about assessing where you’re at right now. What, at this very moment, do you feel is your priority for personal growth? Professional growth? If there are any incomplete goals or projects from last year, write down how far you are from completing them.

Life Audit

Both Shen and MacKay say you should also do a life audit. This is something I haven’t done myself – not in this exact format anyway, though I have done a modified version of it without realizing it.

“Life audit is a technique used by many,” explains Shen. “Take a broad look at the different parts of your life and see what’s going well and what might need some attention.” Open a notebook – or if you have a Clever Cactus planner, flip to your My Notes section (page 205) – and get auditing!

1. First, rate the following from 1 (totally unfulfilled) to 5 (completely fulfilled):

  • Health/Fitness
  • Friends/Family
  • Work/Career
  • Money/Finances
  • Travel/Adventure
  • Personal Growth/Learning
  • Personal Happiness

2. Then, reflect on why you gave each area the rating you did. Is there anything you can do to bring a low rating up for the coming year? What can you do to keep a high rating high?

3. Next, write three to five goals, targets or “wants” for each category. Try to make these as actionable and measurable.


For personal happiness, “be happier” is not an actionable goal. Sure, it’s the end goal, but it’s not something you can really measure. Instead, look at all those notes from the previous year. What made you happiest? If it was an activity, like chatting with a specific person, your goal here could be “do that activity one a week/month/whatever frequency is feasible”. This list will then become your habits, tasks and goals for the coming year (I’m getting ahead of myself. That’s part of the next step!)

Step 3: The Future

Luckily, there’s no dark-cloaked spirit to take us to a fog-filled graveyard during our annual review. Instead, this step is more like the bright sunny morning when Scrooge wakes up, all cheerful and ready to be a better person. You’ve seen where you were, you’ve established where you are, you’ve identified what you need to work on. Now it’s time to pick your goals and direction for the next 12 months.

Lessons from last year

Take a moment to really assess your previous year (again) by answering the following questions*. Use the answers you crafted in Step 1 and your life audit as references.

  • What do you want to learn in the coming year?
  • What tasks, projects, or other work do you want to spend more time on?
  • How will you let go of the tasks that you want to do less of?
  • Where is it time for you to grow? What skills do you need to sharpen to do that? How will you grow those skills?
  • What kind of help do you need to move forward? Where will you get that help?
  • What is your mantra moving forward for when you get stuck?

*These questions all come from Christie Mims’ article.

Define your coming year

This is where you decide what is best for you, and what you will devote your time, energy and focus on for the next 12 months. This decision makes it a lot easier to stay on track throughout the year, because anything outside of what you’ve defined is, not to be harsh, simply not important.

Keep that life audit open and, on the next page, do the following:

1. What are all the things you want to do in the coming year?

Write. Everything. Down. This list and your Life Audit goals list will be your main reference for the next two points.

2. Pick three Big Goals you want to do no matter what.

  • These Big Goals should span months, like home improvement projects or developing new skills or launching a new business.
  • Whatever it is, it must be something that will make the year a complete success when you’re done.

3. Pick five Small Goals you want to do… but if you don’t, it won’t be the end of the world.

  • These Small Goals are more along the lines of fostering a new habit (daily yoga! Less social media time! Weekly chats with friends! etc).
  • They can also be smaller projects – ones that take a few weeks rather than months. (Paint the office! Go camping!)

4. Beside each goal, big or small, write down your definitions of “success”. What does success look like to you for that goal? The “to you” part is very important… this isn’t success in other people’s eyes. This is all about you.

  • This helps you define your goals, taking them from vague “Be Bendier” to specific “Do Yoga X Number of Times”
  • Remember that goals are the IDEAL. Success can be different.
  • Defining success for each goal, big or small, also helps you determine if you did, in fact succeed. There will be no room for doubt at the end of the year!

Daily yoga is the ideal, but success could be doing yoga three times a week on a regular basis for at least three months. Sure, it’s not the ideal, but it’s loads better than not doing yoga at all.

5. Beside each goal, big or small, write down WHY this goal is important to you.

  • Acknowledging and writing down why you want to achieve something (or change a habit) will help you stay motivated and inspired throughout the year.
  • Try to name at least one underlying need or desire that the goal meets/fills.

Back to the daily yoga… in my case anyway, it’s to help alleviate constant, persistent muscle pain caused by old soccer injuries.

6. Beside each goal, write down:

  • How happy you’d be if you accomplished 60 to 80 percent of your target.
  • How disappointed would you be if you didn’t?
  • If any of the goals make you go “meh”, they don’t deserve to be on your list. Scratch those right out.

Seriously, don’t put anything half-hearted on your goals list. It’s much better to have just one big, life-changing thing than to try to force three full big goals you don’t really care about.

Set it in stone

When you’ve got your three Big Goals, it’s time to write them down somewhere permanent and obvious. Someplace you’ll always be able to find them. Somewhere you can look at them throughout the year.

Like in your Clever Cactus “Goals” section (page 8)!!

Give each goal a number (you can make the numbers the “priority” of the goal, or just a way to reference it on the following pages… up to you!) In the appropriate section write down:

  • The goal name/title/phrase
  • Your “success” definition
  • Your motivation

Once you’ve set your Big Goals in stone, it’s time for the final (and my favourite) step – planning!

Keep it front & centre

If you don’t have a Clever Cactus planner, here are some ways you can keep your goals front and centre in your life:

  • Write each goal on a piece of paper & tape it to the wall in your office
  • Keep your goals as a screensaver on your computer
  • Put your goals in your project management system as a starred item or what-have-you
  • Draw pictures that represent your goals, frame them, and hang them someplace in your house where you’ll always see them.
  • Add your goals to your Notes pages.

Step 4: The Plan

RIGHT! Now that you’ve defined success and set the focus of your year, it’s time to map out your route. Plan how you’ll accomplish all these goals, Big and Small. I’ll go into this deeper in a future article about “goal setting”, especially since this article has gotten very long, so here’s a quick overview of what to do.

If you have a Clever Cactus planner, use pages 9, 10 and 11 for this step.

Big Goals

For each, write down the following:

  1. Milestones – give each Big Goal a few milestones.
  2. Steps – write down what you need to do to accomplish each milestone.
  3. Due dates – give yourself deadlines to accomplish each milestone. Write those down in your calendar/Clever Cactus planner.
  4. Habits & regular tasks – if your Big Goals include fostering/developing new habits or tasks that need to be done every day, week or month, write them down in this section.

Small Goals

For each, write:

  1. The habits and regular tasks that will get you to your goals.
  2. Plan how to make them an ingrained, integral part of your life.
  3. Small Goals can get a due date, too, especially if they’re week-spanning projects (like painting your office).
  4. Add them to your calendar right away.

To stay on the path you’ve charted for yourself, set a reminder to check in on your progress periodically throughout the year. Clever Cactus planners come with a note to check in each month – you’ll find it on each month’s To Do List. You can check in once a month, as I do, or once every three months. Or every quarter. Or halfway through the year. Your choice!

Remember, it’s about the journey

And now you’re done with your annual review! You now have an idea of your personal growth for the previous year and a growth plan for the coming year. The only thing left to do is to, well, get started!

The ultimate aim with this whole process is to focus on what you’re doing, rather than where you’re going. It’s important to “have clear goals but focus on your process and systems,” writes Keiffenheim. “It’s easier to focus on the outcome but the goal is not in your control. Obsessing over the outcome prevents you from immersing in the process.”

I’ve designed the Clever Cactus planner to help me focus on what I’m doing to achieve my goals, rather than the goal itself. Every week I’m looking at the next milestone, the habits, the little steps I need to take. Every month, I’m taking stock of where I’m at and what I need to do moving forward. At the end of the year, the whole thing has become a process ingrained in my daily life rather than an overwhelming and seemingly unattainable need to succeed. And that’s what annual reviews are all about. Fostering personal growth as a whole, and mapping out your journey towards happiness, health and your best life.

Clever Cactus Parodia Ottonis doig an Annual Review

“Goals are good for setting a direction, but systems are best for making progress.”

James Clear


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