How To Plan Your Year

Read Time: 8 mins

I’m so excited! We are rapidly approaching my favorite day of the entire year: January 2nd. I love this day more than my birthday or Christmas.

January 2nd is the launch of a brand new year. January 1st doesn’t really count because that’s a national holiday in most countries so most people are just sitting around hungover from New Year’s.

Not only is January 2nd the start of a new year, but it’s also the start of Go Time, the timeframe between January 2nd and May 31st, the best time in the entire year to accomplish your goals. This is because, in the Northern Hemisphere at least, January through May is when you combine relatively bad weather is the fact there are no major holidays. This means everyone is available for business or any other objective you may have.

There are lots of ways in which you can plan a year and you may have already heard about some of them. In this article I’m going to tell you exactly what I’m doing to plan out all of 2024. I plan every year in December but this time around is special. For various personal reasons, some of which I’ve discussed at my YouTube channel and podcasts, I plan on making 2024 literally the best year of my entire life.

This is going to be difficult, since almost all of the last 17 years of my life have been amazing beyond belief, setting the bar for the Best Year Ever™ quite high.

This means I’m going to have to be 100% on my game in 2024, including planning it out in ways I never have before.

Here’s exactly how I’m doing that.

1. Start the year in September instead of January

This is a little cheat code I discovered recently. It’s one of those things that are so stupidly obvious that you feel like a dumbass for never having done it before.

Instead of working on your amazing year in January, why not start working on it in or around September of the prior year? This gives you an extra four months to ensure your year will be a great one.

I have been working my ass off since September of this year (2023) to make next year (2024) fucking amazing. It doesn’t make sense to me to start planning 2024 in December and start working on it in January. By starting the year around September, most of the heavy lifting for the year is already done once I hit January 2nd.

This January is going to be shockingly smooth as compared to my other Januarys in the past because I’ve already put in four months of hard transition work (and it has been hard) before January even started.

As I write this it’s mid-December and I’m not even done yet, but I’ve got a huge amount of groundwork laid for next year in ways I have never done in the past.

2. Set goals for the year

This is the obvious and easy one. Historically I used to set 10-15 annual goals. In the past few years, I realized this was hurting me because I would always feel bad at the end of the year by not hitting all ten goals even though I hit four or five big ones.

So I switched my model from setting 10-15 annual goals to 2-5 goals that were super-duper important and very clear.

Clarity is important. Instead of having a goal like:

“Make $100,000 in 2024.”

You would instead have:

“Make a total of $100,000 in net profit extracted from my 100% location-independent business before taxes.”

Also, I think it’s better to set more realistic and achievable goals when talking about annual goals than very aggressive ones. The goal is to improve every year, to move forward every year. It’s not to set a giant goal and then beat yourself up about it at the end of the year when you don’t quite hit it.

3. Plan all travel for the entire year in advance, down to specific dates and locations

This is important for five flags / international guys like me. Historically I’d plan my specific travel dates and locales about three months in advance and then just have a general idea of the next 6-12 months after that of where I would go.

About last year, mostly at the urging of my team, I forced myself to plan 100% of my international travel an entire 12 months in advance. That means I have it down to specific dates instead of “I will go to Paraguay sometime in June.”

This was a lot of up-front work but it was worth it; 2023 has been the smoothest travel year for me probably ever. 2024 needs to be even smoother.

As of the writing of this article, I have one of the final “drafts” of the entire year of 2024 planned. I’m going to 100% solidify it by the end of next week (well before New Year’s).

Once you know exactly where you’re going and when now you can plan the year in much more detail than you could if you weren’t 100% sure.

If you don’t live an international lifestyle like I do this isn’t as important to you, but many of you are looking at getting new residencies and flags next year, so the time to plan out when you’re going to go is NOW, not next year.

4. Set weekly and quarterly standards that you adhere to all year

Standards are things like…

  • How many hours per week you will spend on Improvement Work (work that increases your income instead of maintains it)
  • How many hours per week you will exercise, meditate, stretch (for us older folks), read, or do other self-improvement tasks.
  • Specific weekly, monthly, or quarterly benchmarks will you ensure your business will hit or maintain
  • Maximums on things that may take you away from your goals, like video games, cheat meals, watching TV shows, wasting time on social media, and so on
  • Anything else you should be doing regularly to ensure success and progress

I have come up with a set of weekly standards for myself and for my companies that I am going to force myself to adhere to every damn week, even if I don’t feel like it, find it boring, or delude myself by thinking I’m “too busy this week” to address them.

5. Focus on quarters, not years

This was a game changer for me a few years ago when I learned this from one of my mentors, Dan Sullivan. Since learning this, I have heard this same technique from no less than four other people who make way more money than I do, so I have 100% confirmation this works, and works well.

The technique is a mindset shift away from years and towards quarters.

The problem with focusing on an entire year is that a year is just too long. Way too many things could happen in eight or ten months from now that you have no control over or aren’t planning on. Also, as I’ve said many times, the closer a goal is to today the more motivation it has on your actions today. Something that isn’t going to happen for 12 months isn’t going to have a lot of motivational power behind it.

On the other hand, one quarter, or 90 days, is short enough that you can more easily control outcomes and it has strong motivational power over you. It’s also long enough to get some big shit done.

How much can you do in a week? Not that much, if we’re being honest, even if you’re a very focused and hard worker. But how much can you get done in three months of focused work? I can tell you from personal experience, a lot. You can damn near change your entire life in three months. And you don’t have to wait 12 months to do it.

“But Caleb, this entire article is about how to plan your YEAR…”

Right, it is. The concept of the calendar year is still important and embedded in your mind from decades of Societal Programming. You can and should do things like set (a few) annual goals and plan out logistics like travel out for one year. But in terms of actually making specific plans and setting very specific goals and to-do items, you should focus on the quarter, not the year.

Therefore, step five is to plan the first quarter of the next year, January 2nd to March 31st. Unlike the year where you just set a few goals, you’re going to plan out QTR 1 in great detail. Set as many goals as you want for the quarter (within reason of course) based on your annual goals. Then, make a to-do list of every single little thing you need to do to accomplish those goals. These can be individual to-do items or clusters of items (called projects). Be as complete as you can. Lastly, put a specific date deadline for every to-do item.

My quarterly plan is usually about three pages long, with goals, standards, projects, and to-do items. However, my life is probably more complicated than yours so when you do your quarterly plan it may be shorter than mine, and that’s okay.

Once a week I start with my quarterly plan as a baseline for action for that week. It’s very powerful.

You might be wondering if you do any planning for the second, third, or fourth quarters of the year since we are planning the year after all.

You can, and it’s a perfectly fine thing to do, but I don’t. Other than things like travel logistics, I don’t worry too much about specific to-do items and plans for quarters well past the quarter I’m currently planning (in this case, first quarter of the next year). I instead put all of my energy into the current quarter.

And that’s how I’m going to, hopefully, make 2024 the best year of my life.

Feel free to copy that goal and make 2024 the best year or your life too.


To have your question featured here where I will write an entire article addressing it, click here. You will always remain anonymous.

J.R. Writes:

My question is about outsourcing. Could you please provide a breakdown of the tasks that a location-independent business owner should delegate to others? I’m particularly interested in knowing the sequence of outsourcing – which task should be handed off first, followed by the next one, and so on.

My Answer:

Here are the functions you need to outsource and in the approximate order you should outsource them. The more money you make and the busier you get, the more you go down this list as you continue to outsource more items.

1. Accounting (taxes). You need an accountant to prepare your tax returns every year to make sure your collapsing Western government financially rapes you with its highest-in-history tax rates. Failure to do this, or do this correctly, means very serious trouble for you, including getting your bank accounts garnished or going to prison, so this should be the first thing you outsource.

2. Bookkeeping. Next, you need to have someone else manage your books (I recommend QuickBooks for most small business owners) so you don’t have to. It’s a very low ROI action that is cheaply outsourced.

3. Technical – Setting up websites, managing web services, etc. This is not shit you should be doing yourself once you start making a little money, regardless of how tech-savvy you are.

4. Graphic design – Logos, memes, thumbnails, website graphics, etc. Cheaply outsourced, is your friend here.

5. Repetitive grunt work – Any recurring administrative tasks you do that need to be done but don’t require a lot of skill.

6. Administrative – Proofreading, order processing, paperwork handling, etc.

7. Customer Service – Have someone else do things like answer customer questions, process refunds and discounts, etc.

8. Your entire email – That’s right. Have someone else check your email and route the 10% or so that they can’t handle to a second email account for you that no one knows about.

9. Social Media – Easily outsourced.

10. Staff Management – A key person who manages your other team members and takes over all or most of your operations.

11. Client deliverables – Tasks done directly for clients you can outsource so you can focus on the higher-value deliverables.

12. Marketing – Copywriters, ad buyers, media buyers, telemarketers, SEO, email writing, etc. Whatever marketing you’re doing that doesn’t literally require your face, outsource it.

13. CFO – Upper-level strategic financial decisions need to be made by a financial expert, not by you.

13. Innovation Scaling – This is when you have people actually do your key deliverables for you, at least to some degree. This would mean things like hiring coaches to do your coaching for you, ghostwriters to write your books for you, and so on.

14. Salespeople – This includes closers  (BDRs) and/or appointment setters (SDRs).

15. Innovation Management – Someone who implements all innovation systems you create. You tell them the new thing you want, and they do it all for you.

Generally speaking, you want to outsource functions in the above order. For example, you would not want to outsource your email when you haven’t yet hired a technical person or graphic designer. However, there often can be exceptions to the order listed above. For example, once you outsource administrative you may want to immediately hire a salesperson. This is acceptable under certain conditions as long as you’re organized.

Leave your comment below, but be sure to follow the Five Simple Rules.

  • Hunter Uprising
    Posted at 05:26 am, 25th December 2023

    Great value and update to your previous advice on planning your year. Thanks Caleb!

  • bluegreenguitar
    Posted at 12:48 am, 2nd January 2024

    Best wishes for everyone in 2024! Excited for Go Time. Also, great to see the blogs back in action!

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