The Step-by-Step Annual Planning Guide for Overachievers

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I exploit to be a horrible annual planner. Then I learn every part I may discover on planning, spent 1000’s on workshops, and iterated my course of over ten years. Now, I’m badass at this.

I’m going to show you every part I learn about annual planning. This gained’t be straightforward. This is designed for overachievers. I’ve held nothing again.

So, why undergo this course of? It’s a significant time dedication. I’m investing 4 days into mine.

First, it lets me zoom out and see the larger image.  It’s laborious for you to see the larger image if you’re caught in an infinite loop of emails and zoom conferences.

I reached a crossroads final yr. I used to be now not enthusiastic about working affiliate marketing online campaigns or creating programs. The feeling was lingering for years. So final yr, I spent a major period of time confronting this sense.

And then I spotted I wanted to maneuver on from this trade. I needed to maneuver on to initiatives that I might be obsessed about.

Second, it helps you join the dots. There was plenty of ache this yr. None of our years went in line with plan. What classes are you able to study so that you don’t repeat the identical errors once more?

Finally, you’re infinitely extra prone to obtain your required outcomes. I imagine that a profitable life comes from doing laborious issues.

Talking about teamwork is simple. Firing your worker since you notice they’re not an incredible tradition match anymore is tough.

Declaring your targets on Facebook is simple. It’s laborious to suppose, analyze, and reverse engineer the way you’re going to attain your targets.

That’s my mantra for 2021 – “Do laborious issues.” Everyone desires to take the trail of least resistance. You gained’t have a lot competitors if you select the more durable path.

Many individuals gained’t hassle with annual planning as a result of life’s too unpredictable. Look at how 2020 went for everybody. I get it.

But right here’s the factor: the self-discipline of planning means you’ll react higher. 

“You know the business plan won’t survive its first encounters with reality,” he says. “But the discipline of writing the plan forces you to think through some of the issues and to get sort of mentally comfortable in the space. Then you start to understand, if you push on this knob, this will move over here and so on. So, that’s the first step.” – Jeff Bezos

Life is like jazz. There’s a rating you may observe precisely, however you’ve gotten permission to riff and make the music bolder.

I don’t know what 2021 has in retailer for us. But I promise you that your yr might be higher when you make investments the time into annual planning.

You convey the vitality – I’ll provide you with my actual blueprint.

Some Notes Before You Start

There are some things you need to do earlier than you get began.

zero.1 Be within the Right Environment

Don’t do that in your house workplace. You’re too near the trenches. You want an atmosphere that evokes you.

Look at how Muhammad Ali educated for his fights. His unique coaching camps had been in Miami. He needed to go away Miami. Too distracting. He constructed a brand new coaching facility in Deer Lake, Pennsylvania. It was known as “Fighter’s Heaven.”

It gave him full focus to coach for his large fights.
You want to search out your “Fighter’s Heaven.”

Here’s my formulation:

Rent an Airbnb that’s inside driving distance. Around one or two hours away is nice. Don’t take care of the stress of airports.Be near nature.  I need you to have the ability to open your door and see a forest, a mountain, or a lake. This makes a distinction.Don’t be too removed from civilization. I wish to nonetheless be 30 minutes from a city. Going out for dinner every evening is my reward.No outdoors work. You’re right here for the annual planning. No conferences. No checking electronic mail. Be disciplined.

 An instance of the vibes I need. Just be sure that it has WIFI. Photo credit score: Pixabay.

Here’s my schedule this yr.

Sunday: Leave at 4pm. Settle into city.
Monday: Day 1 Reflections. Go into city for dinner.
Tuesday: Day 2 Planning. Go into city for dinner.
Wednesday: Drive house at 11am.

I do know it’s tempting to try to shorten your journey to economize. But you don’t need the check-in, and check-out processes to interrupt you.

zero.2. Adapting This to a Team

This guideline is for people doing their private planning, however you may simply adapt this to a crew.

If you’ve gotten a crew, then I like to recommend doing two separate annual plans.

For the corporate model,  I like to recommend doing this in individual together with your workers. It additionally doubles as facetime when you’re distant.

(Note: This article is supposed to be evergreen. If you’re studying this in the midst of the pandemic, you are able to do this by way of Zoom)

Do your private annual planning the weekend after. Don’t do it again to again.

I attempted it as soon as. It sucked. I had no vitality after the corporate one.

zero.Three. Sweep Your Digital Dust

It’s necessary for Chinese individuals to clear their homes for the New Year. It symbolizes a want to put the previous behind, say goodbye to the previous yr, and welcome within the New Year.

We’re going to do a digital model of this. I need you to inbox zero every part.

Answer all excellent emails.Go by means of your Task Manager and filter out duties.Clear your laptop computer. I really like doing a reformat of my laptop computer!

zero.four. Do Your Homework

Annual planning could be mentally and emotionally draining. Take a while to undergo this text.

Is there something that you just’re lacking? You won’t have an inventory of core values but, or a life’s mission assertion written. That’s OK. You can work on it now.

Create a guidelines. Gather all of your financials and paperwork in a single place. Make every part frictionless for your self.

You need most of your vitality in the course of the retreat to be spent on considering.

This framework might be intimidating if it’s your first time doing it. Give it your greatest shot. Don’t skip any sections. It’ll get simpler with observe.

And don’t really feel the strain to do all this in a couple of days. It’s high quality when you’re nonetheless engaged on this after January. Focus on progress, not perfection.

Day 1: Looking Back

Ray Dalio is probably the most profitable hedge fund supervisor on this planet. His favourite precept is “Pain + Reflection = Progress.

He believes that each ache we undergo in life incorporates a “gem.” But we now have to spend time reflecting to uncover these gems.

We’re going to spend all the day reflecting. I’ll provide you with some frameworks and inquiries to information you.

1.1 What Happened This Year?

It’s been an extended yr. Take a stroll down reminiscence lane. Go by means of this yr month by month.

Write down all the main occasions that occurred every month. It could be laborious to recollect. Go by means of your calendar, emails, and job managers to assist refresh your reminiscence.


This is simple in case you have a system of doing a month-to-month assessment.

1.2 Deep Dive into the Different Departments

Life and work could be organized into departments. This helps us see intimately how we’re performing in numerous areas.

Your firm is producing report income. If you take a look at your organization as an entire, you’d suppose that nothing’s improper. But analyze every division. You may discover that the customer support division is missing.

It’s taking 5 days on common for clients to get a response. They’re beginning to go away unhealthy critiques all over the place. Influencers are beginning to trash your merchandise. These are main indicators. If you don’t enhance this division, then it’ll have an effect on the way forward for your complete firm.

This applies to life, too. I’ve seen many individuals go “all in” on their companies for years. Their wealth and profession is perhaps a 10/10. But what occurs if their well being or relationships go all the way down to a Three?

I don’t imagine somebody’s life can really be “balanced.” We’re looking for “danger zones.” We’re ensuring no areas of our lives are weak sufficient to carry us again.

Let’s look into the departments.

I categorize my private life into these buckets:


You can get extra granular with every space.

Health -> Mental Health, Exercise, Diet

Relationships -> Family, Significant Other, Friends, Children

Financials -> Budget, Retirement, Investing, Taxes, Robustness

Adjust accordingly for your life.

A number of issues that I’m wanting for:

Am I balanced in the way in which that I need? I spent an excessive amount of time enjoying video video games this yr. I spent too little time finding out Spanish. Seeing this lets me take into consideration how I can modify my techniques and atmosphere subsequent yr.Are there any areas of my life which are underperforming? I’m not doing as effectively within the friendship subcategory this yr. Quarantine made it robust, however I may’ve known as extra individuals. I’m going to make an effort to enhance subsequent yr.Did I obtain what I needed in these areas this yr? Why or why not? Identify the obstacles in your means.
Give your self a rating in every space. Rank your self out of 10. If you’re scoring excessive in an space, that’s a sign to maintain doing no matter you’re doing. Scored low? That’s a sign you have to make some adjustments.What techniques can I construct? I didn’t perceive the significance of psychological well being in my 20’s. So my answer is to create totally different techniques to take care of this space. Some of those embrace day by day meditation, journaling, searching for remedy each time I wanted it.

Let’s take a look at the departments in a enterprise.


If you’re an even bigger firm, then you may add in departments like customer support, challenge administration, and many others.

I like to recommend protecting it easy. Too many departments imply you’ll begin shedding deal with what issues.

If you’re doing an annual assessment with a crew, then each division head ought to put together a report. Let them personal it.

Here’s an instance for Finance:

Show the numbers. Income assertion, stability sheets, money circulate forecasting. Make charts and graphs the place needed.Explain the numbers. Not everybody understands funds. Their job is to make it straightforward for the remainder of us.What occurred this yr? “I don’t think Charles spending $3,000 at Spearmint Rhino in Las Vegas was the best use of our funds.”Recommendations for subsequent yr. “Our monthly software and subscriptions expenses are at $6,000 a month on average. Here’s how we can bring it down to $4,000 a month.”

Analyzing a division is easy when you’re already utilizing a framework comparable to Objective and Key Results.

Compare this yr’s outcomes to what was deliberate. How did the Key Performance Indicators line up?

1.Three Reflect on the Year

Now you’ve gotten a clearer image of what 2020 was like. Now it’s time to make sense of what occurred.

Here are a sequence of questions that can assist you replicate.

What Were My Big Wins This Year?What Were My Losses This Year?What Happened This Year That Surprised Me?What Were the Biggest Lessons I Learned?If I had a time machine and will return to 1 yr in the past, what would I’ve achieved in another way?


I am going into considering time mode on this part. You’ll see that the primary few solutions you’ve gotten will come simply. Then you’ll be “stuck” for a couple of minutes. The subsequent solutions? That’s the place the gold is.

You must be trustworthy with your self. Let’s say you set a objective to lose 15lbs this yr, and also you gained 15lbs as a substitute.

It’s straightforward responsible quarantine. The gyms had been closed, and it was straightforward to emphasize eat. It’s bullshit and we each understand it.

If somebody had a gun to your head, you’ll’ve discovered a solution to train. You may’ve run outdoors. But you didn’t. This is the place it’s important to go deeper to know what occurred.

You can’t make enhancements when you’re not conscious. If you’ve gotten bother with self-awareness, then it may be useful to ask for constructive suggestions from others.

1.four Evaluate Your Mission and Core Values

We want goal in our lives to really feel fulfilled. We want a cause to get up within the morning moreover amassing a paycheck.

This is the half the place I ask myself, am I dwelling as much as my mission? Am I dwelling in line with my values?

One of my core values is to “push my consolation zone.” Everything that I need in life comes from pushing it. It’s what inspired me to maneuver to Asia, begin talking publicly, and even begin this weblog.

I didn’t do an incredible job this yr of pushing my consolation zone. Some of my unique plans weren’t doable attributable to quarantine.

I maintain myself accountable, although. I may’ve made changes on a quarterly or a month-to-month foundation. There are loads of methods to reside up this worth even when I’m caught at house.

That’s it for Day 1. It’s time to get well. I’ll go for a jog within the space. Go into city to seize some dinner. And then I’ll watch one thing on Netflix.

Go to mattress early. Make certain to get loads of relaxation for the following day.

Day 2: Planning Next Year

We did a radical evaluation of 2020. You perceive what occurred this yr.

Now it’s time to look ahead.

2.1 Review Your Long Term Goals

Before I begin planning the yr, I need to do a fast refresher on the larger image of my life. You must know the place you’re going earlier than you begin planning your journey.


Review Your Life MissionReview Your Core ValuesReview Any Three- or 10-year Goals You’ve Set

You additionally want to guage if these long run targets are nonetheless related to you.

At one level, I needed to put in writing a e book. Now? I’ve zero curiosity in it. The want continues to be there to show and assist individuals. But perhaps a e book’s not the most effective methodology for me.

Starting a podcast sounds extra enjoyable and attention-grabbing to me than writing a e book.

Don’t be afraid to alter your targets in the event that they’re now not related to you. My vacation spot is similar, I’m simply taking a unique street to get there.

2.2 Write Out Your One Year Vision

Most individuals begin itemizing out their targets. There’s a priceless step earlier than that known as the Vision Story.

You write out what you need your life to be like a yr from now.

I’ll write an imaginary instance:

“I’ll stop my job. My affiliate marketing online aspect hustle will develop to a revenue of over six figures a yr. This freedom will permit me to journey the world. I’ll discover dwelling in Asia, Eastern Europe, and South America.

I’ll take my health extra critically. I’ll drop all the way down to 185lbs and 10% physique fats. I’ll do that by means of a mixture of CrossFit and weight-reduction plan. In order to carry out at my greatest, I might be utterly sober. I gained’t drink any alcohol, smoke any weed, or do any medicine.

I’m single now and am high quality being single subsequent yr. However, I’ll positively date a bit after I’m in numerous nations.

I don’t have an incredible social circle the place I’m at proper now. I need to community with extra associates and entrepreneurs subsequent yr. I’ll go to a number of conferences.”

Do you see how a lot simpler it’s to plan your future when you simply write it in story format? If studying your story doesn’t excite you, then you have to suppose greater.

I recommend writing out a whole web page’s value. The extra element you give, the higher. The particulars and emotion you place within the story is what will get you excited.

2.Three Prioritizing Your Outcomes

The story was a brainstorming device.

Chances are that you’ve loads of belongings you need to obtain for this yr. Unfortunately, your time, vitality, and a spotlight are restricted.

I solely set three outcomes for all the yr. Three is simple sufficient to recollect and retains you centered.

Your common individual is simply too bold and units a ton of outcomes. Here’s what occurs after a yr.

Earn six figures in revenue from affiliate marketing online  – NOT ACHIEVEDSpend a minimum of a month in three totally different continents – NOT ACHIEVEDReach 185lbs and 10% physique fats – NOT ACHIEVEDRead 20 books ACHIEVEDJournal on daily basis – NOT ACHIEVEDGet scuba diving license ACHIEVED

Note: Notice how particular and measurable every final result is. It holds you accountable.

Your assets are too unfold out. Our mind tends to deal with doing what’s best. You’ve achieved two of your outcomes however they’re the least impactful ones.

You learn 20 books this yr and bought a scuba diving license. How a lot of a distinction does that make to your life? Not a lot.

Instead, constrain your self to probably the most impactful outcomes.

Earn six figures in revenue from affiliate marketing online – ACHIEVEDSpend a minimum of a month in three totally different continents – NOT ACHIEVEDReach 185lbs and 10% physique fats – ACHIEVED

Now think about how a lot totally different your life could be if you obtain these.

You know who else units their outcomes in Three’s? Lululemon. Here is Lululemon’s strategic progress plan.

The Company’s three priorities to drive income progress over the following 5 years are:

Product innovation– The Company expects to greater than double the scale of its males’s revenues by 2023. In addition, its plans name for continued growth within the girls’s and equipment companies. Both current and new product classes are deliberate to develop, with strains supporting yoga, working and coaching. The Company additionally plans to proceed its product collaborations, increase its fashionable Office/Travel/Commute class, and pursue new alternatives, comparable to self-care. Omni visitor experiences – The Company expects to greater than double its digital revenues by 2023. The Company will deal with providing an built-in visitor expertise throughout channels that are supposed to encourage, provoke and have fun visitors who reside a wholesome and conscious life-style throughout a number of experiences – comparable to occasions, dynamic new retailer codecs, and its progressive membership program that fosters connections amongst visitors. Market growth– The Company plans to quadruple its worldwide revenues by 2023. The Company’s current success in its worldwide markets demonstrates that the sweat life interprets throughout cultures and geographies and presents appreciable progress potential for the model. Expanding throughout China, in addition to the APAC and EMEA areas, might be continued areas of focus for the Company. The Company additionally believes that appreciable progress potential stays in each the U.S. and Canada and it plans to leverage its agile retailer codecs, digital expertise, and group connection.

What in regards to the different targets?

Forget about them. You need to keep laser-focused. But I do know not everybody thinks this fashion, so I’ll provide you with an answer.

Break them out into initiatives.

One of my targets was to learn to salsa dance whereas dwelling in New York City. I needed it, however it wasn’t necessary sufficient to be considered one of my three most important outcomes.

So I turned salsa dancing right into a quarterly challenge. You can flip a few of your targets into quarterly, month-to-month, or weekend initiatives.

2.four Do a Strategic Gap Analysis

Anyone can set targets. The hardest half is to show them into actuality. Now is the time to suppose. How do you bridge the hole between now and your want?

The simplest way to do that is to do a Gap Analysis.

Here’s my model of it.

Be clear on the top consequence.Understand the place you’re at now.Figure out the obstacles in your means.Brainstorm options to the issue.See if anybody who has achieved what you’re attempting to do.Design the machine and techniques.Take motion.Measure outcomes.Reflect and revise.

I wrote an in depth article on how to do that.

Read: How to do a Gap Analysis

Here are another instruments that I exploit:

Thinking Time:

Getting the correct solutions to your issues requires the correct questions.

COVID-19 is affecting every part proper now. As of me writing this text, a vaccine has been authorized and everybody’s excited. What if there’s a COVID-20 and it’s worse than COVID-19? What can I do now to arrange my enterprise for that risk?

How a few gross sales query?

My clients aren’t shopping for my product due to perceived danger or uncertainty. What are these dangers and the way can I mitigate them?

You can’t give you good solutions in a couple of minutes. But having the self-discipline to reply these questions means you’ll know your enterprise higher.

Here’s an article I wrote on Thinking Time. If you need a ton of considering time questions, learn The Road Less Stupid.

SWOT evaluation: This stands for energy, weaknesses, alternatives, and threats. This provides a excessive degree overview of your enterprise.

I.C.E. evaluation: You’ve brainstormed a number of challenge concepts by now. You can use the I.C.E. framework to see which of them are the most effective alternatives.

You rating every challenge in line with Impact, Confidence, and Ease.

Impact: How a lot of an impression can this challenge have on your enterprise?
Confidence: How assured are you which you can pull it off?
Ease: How straightforward is it to implement?

Charles writes a e book:

Impact: 6
Confidence: four
Ease: Three

Average = four.33

Charles begins a podcast:

Impact: 9
Confidence: 9
Ease: eight

Average = eight.67

This scoring system lets me know that beginning a podcast could be a greater challenge for me, than writing a e book. It’s a good way to determine WHAT to prioritize.

2.5 Critical Drivers and KPIs

Finished together with your evaluation? Now it’s time to know what actions result in the specified outcomes. These are known as vital drivers.

Desired Outcome: Lose 15lbs

Everyone tracks weight. The downside? It’s a lagging indicator.

We need to observe the actions that result in dropping pounds. Samantha desires to deal with exercising and weight-reduction plan.

Critical Driver #1: Go to OrangeTheory class 3 times every week.
Critical Driver #2: Eat 1500 energy a day.

She can create a easy spreadsheet to trace. Is she performing the actions constantly? And if she is, are they making her reduce weight? If not, then she wants to regulate.

Look at your three outcomes for the yr.

What are the vital drivers, and the way are you planning to trace them? 

2.6 Map Out Your Year

image1 1

Next, we’re going to map out your yr in a spreadsheet. I did a fast instance.

You’re not going to fill it out utterly. You’re going to fill issues out the most effective you may. You’re going to revisit this sheet on a quarterly, and a month-to-month foundation.

Let’s take a look at my December 2021. One yr from now.

I don’t know what my work initiatives or private initiatives might be. I do know a number of the anchor occasions.

It’ll be my birthday and Christmas, we’re planning a visit to Peru, and I’ll want to dam out a couple of days to do my 2022 annual plan.

This map helps you reverse engineer your initiatives. Let’s say you’re manufacturing a bodily product. You need it to be prepared for Black Friday.

Draw out a fast challenge timeline.

Quarter 1: Conduct buyer analysis. Make a call.
Quarter 2: Work with the producers to finalize the design.
Quarter Three: Buffer interval. One million issues can go improper.
Quarter four: Prepare advertising and marketing.

People are inclined to underestimate how a lot effort a significant challenge takes. Think about how many individuals are late to an occasion. They can’t even get that proper!

Creating a challenge map for the yr could make your predictions extra correct.

Keeping the Momentum Going

We’re not placing in all this work to be ok with ourselves. We’re right here to attain outcomes. We must implement and create totally different techniques.

I don’t do that part throughout my journey. I reasonably dedicate extra vitality to considering. This subsequent part could be achieved over the following few weeks when you’ve gotten extra vitality.

Three.1 Set Reminders

You must remind your self of your outcomes on daily basis.

Some methods I’ve achieved it:

1. Create a desktop or cellular wallpaper. Hire a designer on Fiverr to make it visually interesting.

2. Sticky notes. Write your outcomes down on sticky notes. Put one on the underside of your monitor, and one other in your rest room mirror.

Three. Accountability accomplice. I had a objective a couple of years in the past to enter a BJJ match. Me and my pal made a $1,000 USD wager. If we didn’t compete, then the opposite individual would get $1,000 USD. I’d not have competed if I didn’t have that strain.

This works amazingly for the gymnasium.

“We’re going to the gym Monday, Wednesday, and Friday. Whoever misses a workout owes the other person $20.”

Three.2 Quarterly, Monthly, and Weekly Reviews

Your annual assessment is a blueprint. You want to ascertain a daily rhythm to ensure you’re on observe.

Quarterly Review – It’s just like my annual assessment, however on a smaller scale. I do the identical factor the place I take two days off and spend it in nature.Monthly Review – Last Friday of the month. Takes me round 4 hours.Weekly Review – Every Sunday. It takes round an hour.

Think of it like a waterfall.

Take your annual plan and break it right into a Three-month plan.

Three.Three Building Systems to Achieve Your Outcomes

It’s laborious to maintain observe of every part. The simplest way for me is to ascertain habits, routines, and techniques in my life.

Let’s take a look at relationships. Most individuals simply say they need to have higher relationships of their lives, after which they go away it to probability.

When I need one thing, I set up a system for enchancment.

Here are a number of the techniques in my relationship division:

Me and my fiancé go on a date each Friday evening.I be sure that to see my mother a minimum of as soon as each two weeks.On Sundays, I put aside an hour to do a catch-up name with a pal.Before COVID-19 hit, I hosted a board sport evening at my house each month for my associates.

I do know this may appear too robotic for some individuals. I get it. But I’ve means an excessive amount of shit in my head.

Creating techniques eases the cognitive load on my thoughts.

Sometimes I get too hardcore into work and Brazilian Jiujitsu. Having calendar occasion to see my mother is my insurance coverage to verify I do it.

Let’s take a look at financials:

My fiancé reconciles our funds each Sunday utilizing a program known as YNAB.

Every month, I spend an hour updating our monetary spreadsheet. I even have a journal the place I checklist what occurred and replicate.

We have a one-hour name each month with a private finance coach. He retains me accountable and helps me from making dumb choices.

Everything in your life could be systemized.

The Plan is Useless, however Planning is Essential

I’m fairly certain that my love of planning and technique got here from enjoying Starcraft as a child.

I discovered the worth of prioritization. I couldn’t have a robust navy and a booming financial system inside the first couple of minutes. I used to be constrained by my minerals and fuel. I had to decide on which one was extra necessary. Most individuals plan targets as if they’d limitless assets. Too many wishes imply nothing’s going to get obtain.

I discovered easy methods to analyze and replicate alone video games. Most individuals simply play video games over and over. It’s enjoyable. But you’re simply turning your unhealthy habits into muscle reminiscence. We don’t have limitless lives within the sport of life. So reflecting lets us get extra juice from the lemons.

And lastly, considering forward made me extra ready. I used to be a Terran most important. I liked investing in my financial system early on, so I may assault in the course of the mid-game. But I knew I’d all the time be susceptible to be attacked early. So I made certain to scout the enemy effectively. I’d create a bunker if I knew they had been getting ready for a “rush.”

So now I feel typically by way of what if’s?

What if I die? I’ve already ready a belief and can. My household might be taken care of, and so they gained’t must endure by means of probate court docket.What if somebody hacks into my computer systems and servers? I’ve 2FA on every part. Everything’s mechanically backed up.What if one other Pandemic occurs? We purchased a deep freezer within the storage. The freezer’s full, and our pantry’s full. We have additional masks.

All these make me extra sturdy.

I don’t know what’s in retailer for 2021, however investing this time into planning will make you extra sturdy.

Please fee this text – it helps me know what to put in writing!