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 find out about annual planning. This gained’t be simple. 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 onerous for you to see the larger image if you’re caught in an limitless loop of emails and zoom conferences.

I reached a crossroads final yr. I used to be not enthusiastic about operating internet online affiliate marketing 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 noticed I wanted to maneuver on from this business. I wished to maneuver on to initiatives that I could possibly be obsessed about.

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

Finally, you’re infinitely extra more likely to obtain your required outcomes. I consider that a profitable life comes from doing onerous issues.

Talking about teamwork is simple. Firing your worker since you notice they’re not a terrific tradition match anymore is difficult.

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

That’s my mantra for 2021 – “Do onerous issues.” Everyone needs to take the trail of least resistance. You gained’t have a lot competitors if you select the tougher 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 would comply with precisely, however you will have 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 if you happen to make investments the time into annual planning.

You convey the power – I’ll offer you my precise blueprint.

Some Notes Before You Start

There are some things it is best 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 surroundings that conjures up you.

Look at how Muhammad Ali skilled for his fights. His authentic 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 referred to as “Fighter’s Heaven.”

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

Here’s my method:

Rent an Airbnb that’s inside driving distance. Around one or two hours away is sweet. 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 prefer 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 make certain 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 dwelling at 11am.

I do know it’s tempting to try to shorten your journey to save cash. 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’ll be able to simply adapt this to a staff.

If you will have a staff, then I like to recommend doing two separate annual plans.

For the corporate model,  I like to recommend doing this in particular person along with your workers. It additionally doubles as facetime if you happen to’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 power after the corporate one.

zero.Three. Sweep Your Digital Dust

It’s vital 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 way of your Task Manager and filter duties.Clear your laptop computer. I like doing a reformat of my laptop computer!

zero.four. Do Your Homework

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

Is there something that you simply’re lacking? You won’t have a listing 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 power through the retreat to be spent on considering.

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

And don’t really feel the stress to do all this in a couple of days. It’s wonderful if you happen to’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 now we have to spend time reflecting to uncover these gems.

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

1.1 What Happened This Year?

It’s been a protracted yr. Take a stroll down reminiscence lane. Go by way of this yr month by month.

Write down all the foremost occasions that occurred every month. It might be onerous to recollect. Go by way of your calendar, emails, and process managers to assist refresh your reminiscence.


This is simple when you’ve got a system of doing a month-to-month evaluation.

1.2 Deep Dive into the Different Departments

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

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

It’s taking 5 days on common for prospects to get a response. They’re beginning to go away dangerous critiques in every single 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 likely to be a 10/10. But what occurs if their well being or relationships go all the way down to a Three?

I don’t consider somebody’s life can actually 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 trying for:

Am I balanced in the best way that I need? I spent an excessive amount of time taking part in video video games this yr. I spent too little time finding out Spanish. Seeing this lets me take into consideration how I can alter my programs and surroundings subsequent yr.Are there any areas of my life which might be underperforming? I’m not doing as effectively within the friendship subcategory this yr. Quarantine made it powerful, however I may’ve referred to as extra individuals. I’m going to make an effort to enhance subsequent yr.Did I obtain what I wished in these areas this yr? Why or why not? Identify the obstacles in your manner.
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 might want to make some adjustments.What programs can I construct? I didn’t perceive the significance of psychological well being in my 20’s. So my resolution is to create completely different programs to keep up this space. Some of those embody every day meditation, journaling, searching for remedy every time I wanted it.

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


If you’re a much bigger firm, then you’ll be able to add in departments like customer support, venture administration, and many others.

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

If you’re doing an annual evaluation with a staff, 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 circulation forecasting. Make charts and graphs the place vital.Explain the numbers. Not everybody understands funds. Their job is to make it simple 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 if you happen to’re already utilizing a framework resembling 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 will have a clearer image of what 2020 was like. Now it’s time to make sense of what occurred.

Here are a collection of questions that can assist you mirror.

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 accomplished otherwise?


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

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

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

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

You can’t make enhancements if you happen to’re not conscious. If you will have 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 purpose to get up within the morning apart from gathering 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 a terrific job this yr of pushing my consolation zone. Some of my authentic plans weren’t doable resulting from 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 dwell up this worth even when I’m caught at dwelling.

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 wish 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 judge if these long run targets are nonetheless related to you.

At one level, I wished to jot down a guide. Now? I’ve zero curiosity in it. The want remains to be there to show and assist individuals. But perhaps a guide’s not the very best technique for me.

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

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

2.2 Write Out Your One Year Vision

Most individuals begin itemizing out their targets. There’s a worthwhile step earlier than that referred to 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 give up my job. My internet online affiliate marketing 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 severely. I’ll drop all the way down to 185lbs and 10% physique fats. I’ll do that by way of a mix of CrossFit and weight-reduction plan. In order to carry out at my finest, I might be fully sober. I gained’t drink any alcohol, smoke any weed, or do any medication.

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

I don’t have a terrific social circle the place I’m at proper now. I wish 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 if you happen to simply write it in story format? If studying your story doesn’t excite you, then you might want to suppose larger.

I recommend writing out a whole web page’s value. The extra element you give, the higher. The particulars and emotion you set 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 got loads of stuff you wish to obtain for this yr. Unfortunately, your time, power, and a focus are restricted.

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

Your common particular person is simply too formidable and units a ton of outcomes. Here’s what occurs after a yr.

Earn six figures in revenue from internet online affiliate marketing  – NOT ACHIEVEDSpend at the very least a month in three completely 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 sources are too unfold out. Our mind tends to concentrate on 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 internet online affiliate marketing – ACHIEVEDSpend at the very least a month in three completely different continents – NOT ACHIEVEDReach 185lbs and 10% physique fats – ACHIEVED

Now think about how a lot completely 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 dimensions of its males’s revenues by 2023. In addition, its plans name for continued growth within the ladies’s and equipment companies. Both present and new product classes are deliberate to develop, with traces supporting yoga, operating and coaching. The Company additionally plans to proceed its product collaborations, increase its in style Office/Travel/Commute class, and pursue new alternatives, resembling self-care.Omni visitor experiences – The Company expects to greater than double its digital revenues by 2023. The Company will concentrate on providing an built-in visitor expertise throughout channels that are meant to encourage, provoke and have fun company who dwell a wholesome and aware way of life throughout a number of experiences – resembling occasions, dynamic new retailer codecs, and its progressive membership program that fosters connections amongst company.Market growth– The Company plans to quadruple its worldwide revenues by 2023. The Company’s latest 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 concerning the different targets?

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

Break them out into initiatives.

One of my targets was to discover ways to salsa dance whereas dwelling in New York City. I wished it, however it wasn’t vital sufficient to be certainly one of my three important outcomes.

So I turned salsa dancing right into a quarterly venture. 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 easiest method to do that is to do a Gap Analysis.

Here’s my model of it.

Be clear on the top end result.Understand the place you’re at now.Figure out the obstacles in your manner.Brainstorm options to the issue.See if anybody who has achieved what you’re making an attempt to do.Design the machine and programs.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 precise solutions to your issues requires the precise questions.

COVID-19 is affecting every part proper now. As of me writing this text, a vaccine has been permitted 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 couple of gross sales query?

My prospects 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 provide you with good solutions in a couple of minutes. But having the self-discipline to reply these questions means you’ll know your corporation higher.

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

SWOT evaluation: This stands for power, weaknesses, alternatives, and threats. This provides a excessive stage overview of your corporation.

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

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

Impact: How a lot of an influence can this venture have on your corporation?
Confidence: How assured are you which you could pull it off?
Ease: How simple is it to implement?

Charles writes a guide:

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 venture for me, than writing a guide. It’s a good way to determine WHAT to prioritize.

2.5 Critical Drivers and KPIs

Finished along with your evaluation? Now it’s time to grasp what actions result in the specified outcomes. These are referred to as important drivers.

Desired Outcome: Lose 15lbs

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

We wish to monitor the actions that result in shedding pounds. Samantha needs to concentrate on exercising and weight-reduction plan.

Critical Driver #1: Go to OrangeTheory class thrice per week.
Critical Driver #2: Eat 1500 energy a day.

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

Look at your three outcomes for the yr.

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

2.6 Map Out Your Year

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 fully. You’re going to fill issues out the very best you’ll be able to. 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 among 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 venture timeline.

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

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

Creating a venture 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 realize outcomes. We must implement and create completely different programs.

I don’t do that part throughout my journey. I quite dedicate extra power to considering. This subsequent part might be accomplished over the following few weeks when you will have extra power.

Three.1 Set Reminders

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

Some methods I’ve accomplished 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 toilet mirror.

Three. Accountability accomplice. I had a purpose a couple of years in the past to enter a BJJ event. Me and my buddy made a $1,000 USD wager. If we didn’t compete, then the opposite particular person would get $1,000 USD. I’d not have competed if I didn’t have that stress.

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 evaluation is a blueprint. You want to determine an everyday rhythm to be sure you’re on monitor.

Quarterly Review – It’s much like my annual evaluation, 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 onerous to maintain monitor of every part. The easiest method for me is to determine habits, routines, and programs in my life.

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

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

Here are among the programs in my relationship division:

Me and my fiancé go on a date each Friday evening.I make certain to see my mother at the very least as soon as each two weeks.On Sundays, I put aside an hour to do a catch-up name with a buddy.Before COVID-19 hit, I hosted a board sport evening at my dwelling each month for my mates.

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

Creating programs 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 referred to as YNAB.

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

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

Everything in your life might be systemized.

The Plan is Useless, however Planning is Essential

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

I realized the worth of prioritization. I couldn’t have a powerful navy and a booming economic system inside the first couple of minutes. I used to be constrained by my minerals and gasoline. I had to decide on which one was extra vital. Most individuals plan targets as if that they had limitless sources. Too many wishes imply nothing’s going to get obtain.

I realized find out how to analyze and mirror alone video games. Most individuals simply play video games over and over. It’s enjoyable. But you’re simply turning your dangerous 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 important. I liked investing in my economic system early on, so I may assault through 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 usually 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 should undergo by way of probate court docket.What if somebody hacks into my computer systems and servers? I’ve 2FA on every part. Everything’s routinely 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 further 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 charge this text – it helps me know what to jot down!