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 little thing I might 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 little thing I learn 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 serious time dedication. I’m investing 4 days into mine.

First, it lets me zoom out and see the larger image.  It’s exhausting for you to see the larger image while 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 working affiliate internet marketing campaigns or creating programs. The feeling was lingering for years. So final yr, I spent a big period of time confronting this sense.

And then I noticed 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 numerous ache this yr. None of our years went in keeping 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 more likely to obtain your required outcomes. I consider that a profitable life comes from doing exhausting issues.

Talking about teamwork is straightforward. Firing your worker since you understand they’re not an amazing tradition match anymore is difficult.

Declaring your objectives on Facebook is straightforward. It’s exhausting to suppose, analyze, and reverse engineer the way you’re going to attain your objectives.

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

Many folks 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 can observe precisely, however you’ve 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 shall be higher should you make investments the time into annual planning.

You convey the power – I’ll provide you with 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 evokes you.

Look at how Muhammad Ali educated for his fights. His unique coaching camps had been in Miami. He needed to depart 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 massive fights.
You want to search out your “Fighter’s Heaven.”

Here’s my components:

Rent an Airbnb that’s inside driving distance. Around one or two hours away is sweet. Don’t cope with the stress of airports.Be near nature.  I would like 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 night time is my reward.No outdoors work. You’re right here for the annual planning. No conferences. No checking e mail. Be disciplined.

 An instance of the vibes I would like. Just make 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 dwelling 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’ll be able to simply adapt this to a staff.

If you’ve 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 staff. It additionally doubles as facetime should 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 power after the corporate one.

zero.Three. Sweep Your Digital Dust

It’s vital for Chinese folks 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 would like you to inbox zero every little thing.

Answer all excellent emails.Go by 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 might be mentally and emotionally draining. Take a while to undergo this text.

Is there something that you just’re lacking? You may not 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 little thing frictionless for your self.

You need most of your power through the retreat to be spent on pondering.

This framework shall 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 follow.

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

Day 1: Looking Back

Ray Dalio is essentially 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 accommodates a “gem.” But we now have to spend time reflecting to uncover these gems.

We’re going to spend the complete day reflecting. I’ll provide you with 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 this yr month by month.

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


This is straightforward you probably have a system of doing a month-to-month evaluate.

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 numerous 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 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 depart unhealthy opinions 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 could 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 searching 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.

Just a few issues that I’m trying for:

Am I balanced in the way in which that I would like? I spent an excessive amount of time enjoying video video games this yr. I spent too little time learning Spanish. Seeing this lets me take into consideration how I can alter my methods 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 robust, however I might’ve known as extra folks. 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 it’s worthwhile to make some adjustments.What methods 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 methods to take care of this space. Some of those embody each 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 retaining it easy. Too many departments imply you’ll begin shedding concentrate on what issues.

If you’re doing an annual evaluate 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, steadiness sheets, money movement forecasting. Make charts and graphs the place essential.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 straightforward should 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 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 will help 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 finished otherwise?


I’m going into pondering time mode on this part. You’ll see that the primary few solutions you’ve 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 objective 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 comprehend it.

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

You can’t make enhancements should you’re not conscious. If you’ve hassle 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 in addition to amassing a paycheck.

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

One of my core values is to “push my consolation zone.” Everything that I would like 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 amazing 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 might’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 better. 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 an intensive 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 objectives are nonetheless related to you.

At one level, I needed to jot down a e-book. Now? I’ve zero curiosity in it. The need remains to be there to show and assist folks. But possibly a e-book’s not the most effective technique for me.

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

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

2.2 Write Out Your One Year Vision

Most folks begin itemizing out their objectives. There’s a helpful 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 internet marketing facet 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 a mixture of CrossFit and weight-reduction plan. In order to carry out at my finest, I shall be utterly sober. I gained’t drink any alcohol, smoke any weed, or do any medicine.

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

I don’t have an amazing 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 should you simply write it in story format? If studying your story doesn’t excite you, then it’s worthwhile to suppose larger.

I counsel writing out a whole web page’s price. 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 software.

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

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

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

Earn six figures in revenue from affiliate internet marketing  – NOT ACHIEVEDSpend at the least a month in three totally different continents – NOT ACHIEVEDReach 185lbs and 10% physique fats – NOT ACHIEVEDRead 20 books – ACHIEVEDJournal day-after-day – 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 received a scuba diving license. How a lot of a distinction does that make to your life? Not a lot.

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

Earn six figures in revenue from affiliate internet marketing – ACHIEVEDSpend at the least 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 can be while you obtain these.

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

The Company’s three priorities to drive income development 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 enlargement within the girls’s and equipment companies. Both present 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 common 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 concentrate on providing an built-in visitor expertise throughout channels that are supposed to encourage, provoke and have fun friends who dwell a wholesome and conscious life-style throughout a number of experiences – comparable to occasions, dynamic new retailer codecs, and its modern membership program that fosters connections amongst friends.Market enlargement– 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 development potential for the model. Expanding throughout China, in addition to the APAC and EMEA areas, shall be continued areas of focus for the Company. The Company additionally believes that appreciable development potential stays in each the U.S. and Canada and it plans to leverage its agile retailer codecs, digital expertise, and neighborhood connection.

What in regards to the different objectives?

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 objectives was to discover ways to salsa dance whereas dwelling in New York City. I needed it, but it surely wasn’t vital sufficient to be considered one of my three important outcomes.

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

2.four Do a Strategic Gap Analysis

Anyone can set objectives. 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 need?

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

Here’s my model of it.

Be clear on the tip consequence.Understand the place you’re at now.Figure out the obstacles in your means.Brainstorm options to the issue.See if you recognize anybody who has achieved what you’re making an attempt to do.Design the machine and methods.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 best solutions to your issues requires the best questions.

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

How a couple of 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 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 pondering time questions, learn The Road Less Stupid.

SWOT evaluation: This stands for energy, weaknesses, alternatives, and threats. This offers 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 most effective alternatives.

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

Impact: How a lot of an affect can this venture have on your corporation?
Confidence: How assured are you that you would be able to pull it off?
Ease: How simple 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 can be a greater venture for me, than writing a e-book. It’s an effective 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 known as important drivers.

Desired Outcome: Lose 15lbs

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

We need to monitor the actions that result in shedding weight. Samantha desires to concentrate on 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 persistently? And if she is, are they making her drop 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 utterly. You’re going to fill issues out the most effective 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 shall be. I do know a few 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 number 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 call.
Quarter 2: Work with the producers to finalize the design.
Quarter Three: Buffer interval. One million issues can go unsuitable.
Quarter four: Prepare advertising.

People are inclined to underestimate how a lot effort a serious 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 attain outcomes. We must implement and create totally different methods.

I don’t do that part throughout my journey. I somewhat commit extra power to pondering. This subsequent part might be finished over the following few weeks when you’ve extra power.

Three.1 Set Reminders

You should remind your self of your outcomes day-after-day.

Some methods I’ve finished it:

1. Create a desktop or cell 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 lavatory mirror.

Three. Accountability companion. I had a objective a number 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 strain.

This works amazingly for the health club.

“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 evaluate is a blueprint. You want to ascertain a daily rhythm to be sure you’re on monitor.

Quarterly Review – It’s just like my annual evaluate, 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 exhausting to maintain monitor of every little thing. The simplest way for me is to ascertain habits, routines, and methods in my life.

Let’s take a look at relationships. Most folks simply say they need to have higher relationships of their lives, after which they depart it to likelihood.

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

Here are a few of the methods in my relationship division:

Me and my fiancé go on a date each Friday night time.I make sure that to see my mother at the 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 recreation night time at my dwelling each month for my associates.

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

Creating methods 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 record 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 enjoying Starcraft as a child.

I discovered the worth of prioritization. I couldn’t have a powerful navy and a booming economic system throughout the first jiffy. I used to be constrained by my minerals and fuel. I had to decide on which one was extra vital. Most folks plan objectives as if they’d limitless sources. Too many wishes imply nothing’s going to get obtain.

I discovered find out how to analyze and mirror by myself video games. Most folks 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 recreation of life. So reflecting lets us get extra juice from the lemons.

And lastly, pondering forward made me extra ready. I used to be a Terran important. I cherished investing in my economic system early on, so I might assault through the mid-game. But I knew I’d all the time be weak 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 believe typically when it comes to what if’s?

What if I die? I’ve already ready a belief and can. My household shall be taken care of, and so they gained’t should undergo by probate courtroom.What if somebody hacks into my computer systems and servers? I’ve 2FA on every little thing. 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 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!