Victory at all costs…
“You ask what is our aim? I can answer in one word: Victory. Victory at all costs. Victory in spite of all terror. Victory however long and hard the road may be. For without victory there is no survival.” – Winston Churchill
That quote is from a speech that Winston Churchill gave way back in 1940.
He was a freshly appointed to Prime MInister by King George VI, after his predecessor suffered a great defeat in Norway against the Germans.
It was World War 2. And the allies were losing a war to Hitler and tyranny.
That speech was his first as the new Prime Minister. What was it meant to do?
One simple thing.
Set the tone.
Churchill believed that victory against the Germans was the only option.
And yet he saw the road ahead as a great challenge that would require much sacrifice, as he lays out in that very same speech:
“I would say to the House, as I said to those who have joined this Government, I have nothing to offer but blood, toil, tears and sweat. We have before us an ordeal of the most grievous kind. We have before us many long months of toil and struggle.
“You ask what is our policy. I will say, it is to wage war with all our might, with all the strength that God can give us, to wage war against a monstrous tyranny never surpassed in the dark, lamentable catalogue of human crime.” – Winston Churchill
Churchill knew that what was required to WIN, was going to have to be something DIFFERENT than what has gone before. That means CHANGE.
And change is ALWAYS painful. No matter what.
Overcoming obstacles?
Learning new skills?
Breaking financial barriers?
All of these things require change.
And perhaps you aren’t trying to do anything as serious as win a world war against a tyrant hell-bent on conquering the world…
…but anything in your life that will require change?
Do not doubt that the universe will fight against you. It will be challenging. It will be hard. It will be painful.
There WILL in fact be “blood, toil, tears and sweat” but…
…it WILL be worth it.
And that brings us to what I want to talk with you about.
A way forward.
A framework, if you will. Something tried and true that millions of people have used over the years to be a catalyst for change in their lives and businesses.
What am I talking about?
What is this framework I speak of?
I’ll tell you.
Challenges.
Simple challenges.
And I bet you don’t know as much about them as you think you do. I’m going to go deep with you on this subject. The ins, the outs, the whys and the hows…
…we are getting into it.
So strap in, flip the on switches, and fire up the systems, because we are about to do some good ol’ fashioned EDUCATION!
3 BIG styles of Challenges…
This is really about building a foundation for that discussion.
And the best place to start with a foundation for Challenges is the 3 main types. They are as follows:
Skills/Education-based:
These kinds of challenges teach something new through regular lessons (like email list building or photography challenges.)
Now many times these are DAILY lessons. But they could be weekly, or even MONTHLY if that is how it makes sense for you.
The result desired is to acquire new knowledge and skill.
Action/Accountability-based:
These style of challenges are about doing a specific activity daily with others for motivation. Think of challenges like Inktober or “10k Steps a Day.”
They take advantage of more than one person trying to finish the same kind of goal, thereby allowing you to capitalize on the collective momentum of the group.
But with this style of challenge, the result is not “finishing a book” or “losing 20 pounds” it is instead the streak created by the process of doing the thing regularly.
Completion/Project-based:
These challenges are working toward finishing something specific by the end (like Novel November or “Build Your Offer in 5 Days.”)
The goal here is to FINISH a project. To walk away with something tangible.
Now keep in mind, these challenge styles can be mixed and matched and ARE very often.
Type One with a hint of Type Two…
Type Three with a bit of Type One thrown in…
We’ll get into that later on, but for now I just want you to get an understanding of the foundation of challenges.
These are the building blocks upon which all challenges are built. Master them? And you can take it anywhere.
We are going to get into each of them a little deeper, starting with Type One…Skill and Education based.
Got the skills?
The first type of challenge I want to talk with you about are Skills and Education Based Challenges.
That is to say, the kinds of challenges that teach something new through regular lessons.
In every niche, in every market…
…there are skills people seek to acquire. There is education that people desire.
Take the ever popular internet marketing space, for example. On any given month of the year there are always people in this niche who desire to become better at email marketing…
List building…
Affiliate marketing…
Traffic driving…
Analytics/metrics analysis…
Networking…
And so on and so forth. The list goes on and on.
That could be said for most niches that you might enter. People are looking to solve problems and most of those problems get solved by acquiring skills, or gaining education.
And I know what you might be thinking. What about A.I.? What about software?
Those things solve problems and I don’t have to learn skills in that case.
Don’t you?
Well what about learning how to USE that A.I.? Or learning how to USE that software?
Skill and education are almost always required. And when you can put a “Challenge” framework around this tangible result of acquiring a skill or getting BETTER at something?
That is very powerful, and it gets people to sign-up.
And it could be anything. For example, Substack is a platform that uniquely utilizes two forms of content on it’s platform.
Notes and Posts.
Posts are essentially emails that go out to your subscribers and then also exist on the platform as these sort of pseudo blog posts.
Notes are like Tweets on X. They are seen by your followers. That’s a big difference.
Subscribers vs. Followers.
And that simple dichotomy that exists on Substack provides the foundation for MULTIPLE challenges. Things like:
“The Substack Better Notes in 5 Days Challenge”
“Substack Subscriber BOOST 10-Day Challenge”
“The Substack Easy Content Framework Challenge”
“The Substack 30 Day Money-Getting Challenge”
And it goes on and on. But all of these challenges are based on one simple concept.
Acquiring a NEW skill. A specific skill that is going to help you move your business forward.
You can do the same thing with practically anything related to or surrounding your niche.
About that action…
Earlier, I talked a lot about acquiring skills and the desire to get new education. And that’s a very true…very real thing. However, that’s not the only kind of effective challenge.
Now, I want to talk to you about ANOTHER kind of challenge that is equally as powerful as the education based challenges.
What am I talking about? Type 2 in that original overview.
Type 2 is Action/Accountability-based challenges.
This style of challenge is about doing a specific activity daily with others for motivation. They take advantage of more than one person trying to finish the same kind of goal…
…thereby allowing you to capitalize on the collective momentum of the group.
But with this style of challenge, remember, as I said previously…
…the result is not “finishing a book” or “losing 20 pounds” , it is instead the streak created by the process of doing the thing regularly.
What does that mean?
It means that your goal would be to write an email a day for 30 days. Not to finish some kind of product, or to make $5k doing so.
The result is created by the mere process of doing the thing daily.
You are creating a habit. You are getting better through repetition. You are building momentum with the streak.
And you are generally using all the other people doing it with you as accountability and motivation.
There is a collective momentum that you can capitalize on to propel yourself forward.
Oftentimes these challenges are run in a setting that allows and encourages interaction between challenge goers.
A Facebook group or a Skool community for example.
A 30 Day Push-Up Challenge is a good example of a challenge like this. Everyday you have a goal to do as many pushups as you can.
The goal isn’t necessarily to do MORE pushups…
…but instead to develop the consistency of doing daily pushups period.
Another example of this would be a Daily Meditation Challenge. You could Meditate daily for 2 weeks. The streak itself is the result.
Oftentimes Challenge Goers can share what they got out of it at the end or along the way.
This kind of challenge is a little different than the education based challenges we were discussing earlier.
That was about acquiring education and skill…
This is about growth through goal setting, consistency, and habit forming.
Both incredibly effective. And great tools for the toolbox of challenges in your business.
Get’er done…
Perhaps one of my favorite styles of challenges is the Completion/Project-based challenge. Basically this is a challenge where you have a goal to get a certain thing done.
Whether that be writing a WHOLE novel, like they do in Novel November…
…where the goal is to get a complete novel (50,000 words) done in one month…
…or it’s to BUILD an email list, like a friend of mine put on in his 14-Day List Building Challenge.
These are very powerful because they are all about walking away with a tangible result. And that is an easy thing to sell to ANYBODY.
“Double Your Money in 30 Days Challenge”
“100 Subscribers a Day Challenge”
“Build an Offer in 5 Days Challenge”
All are examples of this Project-Based Challenge style. And there is no reason why you cannot put challenges like this together for your business.
Just keep in mind that the point of this one is a tangible result by the end of your challenge. That is the goal.
So when you design the thing, make sure you design it around that particular ambition.
Another thing to keep in mind is that these 3 challenge styles I have detailed out for you over the last few emails are interchangeable.
“Double Your Money in 30 Days Email Challenge” (Project-Based type 3)
Can become…
“Writing More Profitable Emails 30 Day Challenge” (Skill Based type 1)
Or could become…
“The Email-A-Day 30 Day Profit Challenge” (Action/Accountability based type 2)
All three of those challenges are largely going to be very similar in nature…but the focus will be different.
They all focus on DIFFERENT results. So the actions might be similar, but the intention is different.
And how do you choose which to do? It’s all based on your reason for doing the challenge.
Are you looking to build consistency?
Learn a skill?
Or finish a project?
The answer to that question will tell you what kind of challenge to put on.
Why does any of this work?
Over the last sections I’ve laid out for you 3 very specific ways of doing challenges.
But moving forward now…why does any of this work?
Well, the bottom line is that Challenges work really well because they tap into several powerful psychological and social motivators at once.
It’s not just “fun…”
…there’s real science behind why people participate and follow through.
They have clear and achievable goals.
Whether those goals are project based, skill based, or streak based…the goals of challenges are always very clear and easy to understand. Success is obvious.
People like that simplified narrative and structure.
You might say, we as humans are drawn to it.
“Write 500 words per day for 30 days” is far easier to follow than “just write more.”
They have a TIME-BOUND structure.
Deadlines create urgency and promote structure when it comes to work habits. Short, fixed time frames (30 days, 5 days, a month) make a goal feel doable, not overwhelming.
A month-long challenge feels manageable compared to “I’m going to write a book someday.”
Small, Incremental Wins.
Breaking a goal into daily or weekly actions triggers dopamine from accomplishment regularly. Each step feels rewarding, and that’s going to keep participants engaged.
Writing 500 words today, finishing a daily jog, or posting a daily drawing gives a small win each day.
Skill-Building and Results.
Even when the challenge is short-term, it can teach a skill, create a habit, or produce a tangible result. The visible progress gives participants confidence and a sense of achievement.
If you finished writing a WHOLE book in “Novel November,” you are going to feel like a writer. By doing a fitness challenge, you are going to feel healthier and more disciplined.
Psychological Commitment.
Challenges tap into commitment and consistency. That’s a core principle in behavioral psychology.
Once people publicly commit to something, or even start tracking progress privately, they’re more likely to follow through.
You might say we are just hardwired for it.
Anyways, there are other reasons as well, but these are just a few.
The bottom line here is that Challenges work because they combine clarity, structure, social proof, incremental progress, and tangible outcomes.
They make taking action easier, fun, and rewarding…
…all while giving the brain the little hits of motivation it craves.
Now does that mean this is the ONLY kind of product or asset that you should be creating going forward? Of course not.
However, to not take advantage of such a powerful tool, would be foolish.
Challenges have been working for years, are proven to work, and there is no reason you cannot use them immediately to build your lists, grow your business, and succeed online.
A Little of this and a little of that…
If I wanted to teach you the skill of list building, a skill that I know people in my market are interested in… (so type 1)
…but also wanted my challenge to be immediately more appealing to my audience, so I add a tangible result, like “1,000 leads in 30 days…” (type 3)
But also I want there to be this element of success where people are going to succeed just by completing the task each day. (type 2)
Well, I could make a challenge that appeals to ALL of those elements if I chose to do so.
Think of the following example:
“A Thousand Leads in 30-Days Challenge”
And then in my subtitle I’ll go on to say:
“I’m going to teach you the POWERFUL SKILL of list building. Through simple actions that you’ll be completing each day, you will begin to not only build momentum but ALSO build your email list!”
So this kind of challenge here?
It’s a Type 3. Project-Based. However, I am mixing elements of Type 1 and Type 2 as well.
So we have primary and secondary types here. I’ve mixed elements of all 3 in this particular challenge.
Why would I do that?
It is 100% based on what you are trying to do with your challenge and what makes the most sense for you. This isn’t a one size fits all scenario and it’s not exactly “paint by numbers.”
I did it here, because it stacked value, made my challenge look easier and more appealing. And also because it would apply and is honest.
That’s not always going to be the case for you though. You have to do what makes sense and what fits your specific needs.
Another example:
“30-Day Jog a Mile Challenge”
In this challenge we are going to be jogging a mile a day. So this is a type 2 style challenge. It’s streak based. Meant to help us build a habit.
But I could combine it with type 1 a bit by adding the following subtitle:
“I’m going to show you EXACTLY how to jog the RIGHT way every day to prevent injury and improve your health in 30 DAYS!”
And you might wonder…could I add type 3 to make this even more appealing? And the answer is in this case you probably could.
If you are jogging a mile a day you are going to be jogging 30 miles in 30 days. That’s over a marathon in length, which is, I believe 26 miles.
You could call that “The 1 Month Marathon Challenge!” And it starts to become a bit more tangible of a result now.
You could make it even more so by adding an overall time to shoot for.
Or a weight loss goal to achieve.
But the point of all this is that you can make your Challenges more appealing and even more helpful just by playing with the type of challenge and the result you are going for.
…mixing and matching isn’t just about the title of the challenge. It’s everything. The subtitle. The copy. The challenge itself.
Less is more…
Another aspect to challenges that can add an interesting dynamic is when you start taking things away. Resources. Time. Money.
Oftentimes taking these things away, not only makes the challenge more challenging…but that actually make it more appealing to the market you are trying to attract.
Think about it.
If I’m going to show you how to build a list and I run a challenge…
I’ll attract MORE people if I say I’m going to do it by spending NO MONEY whatsoever and only using free resources!
Or if I tell you we are going to do a Lose 30 Pounds in 30 Days Challenge, but the ONLY thing I’m allowed to eat is FAST FOOD!
That’s crazy. The contrast alone is going to attract people to the challenge just for the sake of curiosity.
But that is the POWER of taking things away.
Another example is if I say we are going to do a “Build a Business in 30 Days Challenge”
But I’m only allowing myself 15 minutes a day to work on my business!
Imagine that! 15 Minutes a DAY!
People are going to look at that and think, “WOW, if he can do that in 15 minutes a day, surely I can do it too!”
So by placing that constraint on time, I have made the Challenge MORE attractive.
You can do the exact same thing with your challenges. Anytime you start taking resources away. Things that would make the challenge easier…
…you instantly start building captivation, curiosity, and momentum for the challenge.
Toy around with this idea and see what you can come up with.
If you build it…
How do you put together a challenge? I mean, how do you build such a thing?
That’s exactly what I want to get into now. The art of putting together a challenge. Piece by precious piece.
The way I see these challenges is that you start with the overall goal you want to achieve.
Then you divide that up into smaller “benchmark” goals, evenly spaced throughout your challenge. Think of these as “Best practices” or “You should be here” indicators.
And then you break that down into small daily actions.
So for example:
Step 1) Challenge Goal: To Launch Your Email List in 30 Days
Step 2) Weekly Benchmark Goals: At least 10 new subscribers a week, utilizing free traffic from Facebook groups.
Step 3) Daily Goals: 1 piece of valuable free content on social media daily, 10 minutes a day networking in each facebook group.
It is a very simple example. Just to get the basic idea. Essentially you work backwards.
Another example:
Step One) Challenge Goal: Lose 30 Pounds in 30 Days
Step Two) Benchmark Goals: Weigh yourself once a week with a goal of losing 7.5 pounds a week.
Step Three) Daily Goals: Daily meal plans and 30 minutes of activity.
It’s the idea that big challenges contain smaller challenges within them, and you can use the same challenge concept at different magnitudes.
A “create something” challenge works whether it’s creating one thing per day, or creating an entire system by the end.
I won’t go into the minutia of WHERE you should house these challenges. They are beyond that and besides, places are always changing.
What I have been teaching you thus far, is 100% principle based.
These ideas will be just as valid 30 years from now as they are today. A challenge can be delivered in a special report…
…it can be done live on a private membership site or weekly call…
…it can be delivered via email or even blog posts or social media groups. There is no limit to how you can deliver a Challenge.
But just remember…
…when you are building a Challenge. Start with your end goal. The thing that you wish for people to accomplish, and just work backwards, breaking it down into smaller goals and accomplishments…
…until you finally arrive at simple daily tasks that people can perform to achieve the goal.
Free vs. Paid…
Now I want to get into some of the differences between…
…free challenges vs. paid challenges.
First…Free Challenges. Why the heck would you spend all your time and energy doing FREE challenges?
Well, it’s simple. You do them for lead acquisition. This is a fantastic way to build a list of warm and engaged leads.
See, the beauty of this is that you actually build trust and rapport with your leads throughout the challenge, thereby creating REALLY strong leads. So for this reason…
…challenges are extremely effective lead magnets.
Now Paid Challenges? This is about revenue generation, of course…
…but much like the free challenges, this kind of product builds a lot of trust and rapport with your customers. When it comes to the spectrum of expectation that your customers are on…
…with some tips and insights being on one end of the spectrum but an expectation of results being on the other end?
Challenges lean towards the results end of the spectrum, which means you can charge more. You don’t have to, but the justification is there.
These are products that are all about results. Not insights.
Now FREE AND PAID Challenges lend themselves to the upsell very well. When you consider the “ascension ladder” or “ascension pyramid” however you want to call it…
Challenges solve problems. That is their clear cut goal. And you know what happens when one problem is solved?
There is always another problem. That’s just the nature of life and business.
Think about it. You want to lose weight because you’re fat. Okay you do a challenge.
Great, you’ve lost the weight you want to lose. Now what?
Well, now you have the problem of maintaining that weight POST challenge. That’s another problem.
And that’s just one simple example. Sometimes I think that we, as humans, are designed to always seek the next answer to the next problem.
It’s like it’s hard for us to be satisfied.
But regardless, because of the “results’ based nature of Challenges, it makes it very easy to transition your customers to the NEXT solution FOR the next problem.
That solution could easily be another challenge. A more expensive challenge. It could be a simple free 5-day challenge to a paid 30-day challenge.
Or a paid 30-Day Challenge to a Higher Ticket 60-Day Challenge. Just some examples of options you might explore. But I hope this has your wheels turning.
These challenges are extremely powerful, and you can use them to grow your business incredibly well! Now get after it and stop procrastinating!
Case Study: A Successful Free Challenge
In 1999, NaNoWriMo wasn’t an organization, didn’t have branding, and had no website.
It was literally this guy, Chris Baty and a handful of friends. They had a goofy idea to self-impose a one-month deadline for writing a book.
That’s it.
There was no official “delivery”, no formal promotion, and no infrastructure.
So what did they actually do that first year?
They basically said to each other:
“Hey, let’s try to write a novel in a month. Let’s pick July and do 50,000 words.”
And they just… did it.
Promotion?
None.
It was strictly among friends, and the “group” was 21 people total.
How did they “run” it?
Very informally: They met in cafés.
They talked about what they were writing. They kept track of word counts.
They encouraged each other.
Nothing was tracked online.
It was grassroots and completely analog.
In the second year, Chris Baty created the first NaNoWriMo website. It was extremely basic. I’m talking HTML early 2000’s style.
But he added structured rules:
Write 50,000 words. Do it in November. Start from scratch. Count only new words.
It was opened to the public and that was the first time strangers joined.
They had a simple registration system. Just a web form and a very basic “community” feature.
They started a Yahoo! Group which became the first “forum” for discussing the challenge online.
Promotion was still very minimal. Message boards. Hobby writing communities. Friends telling friends.
So this free challenge is very TYPE 3. It’s Project Based. And it had the most humble of beginnings.
The idea was invented. A group did it together. The rules were born. The concept of a shared month-long writing sprint was established.
And it just kind of grew organically from there.
But you don’t have to re-invent the WHEEL to start a free challenge. You can just take ANY problem in your niche and build a challenge around it.
That’s exactly what Baty and his friends did. Chris Baty has said multiple times that NaNoWriMo started because they wanted a “fun, goofy, creative adventure.”
It was more about the experience than the result.
Now…sure you could argue that NaNoWriMo which was rebranded to Novel November…
…actually announced it was shutting down in 2025…and some would say…”well that’s a fail!”
But honestly? That’s like 26 years of Novel November. I’m not sure if that’s a fail.
It was a great idea and it continues to live on, even though the actual non-profit might be folding.
Another great example of a successful free challenge in the online business world is Russell Brunson’s “5-Day Lead Challenge.” Unlike organic community challenges like NaNoWriMo…
…Brunson designed this one specifically as a marketing engine: a short, structured experience that teaches participants how to create a lead magnet while simultaneously building his own audience, warming them up, and introducing them to the ClickFunnels ecosystem.
It offered real value up front, grew his email list quickly, and led participants into his paid programs and software in a natural way…
…making it an extremely effective challenge-funnel. But regardless…these are just a couple of examples of how people have used the idea of a FREE challenge to grow their businesses.
One Funnel Away?
Russel Brunson, who I mentioned earlier is no stranger to Challenges. In fact, he ran a PAID challenge back in 2018 that actually went on for years and made him millions of dollars.
It was called One Funnel Away Challenge and it cost a hundred bucks back then. It ran by my estimate until around 2022-2023 and then closed for about a year.
Now it’s back as a FREE CHALLENGE. Well, sort of free. This Challenge is positioned as a PREMIUM now. What do I mean by that?
I mean you get the Challenge for FREE when you sign up for a ClickFunnels 14-Day Trial.
ClickFunnels is a $97 a month Funnel Building software…
…so I would say that this CHALLENGE is walking a line. Technically, it’s free, but in reality it is being used as leverage to push a very expensive piece of software.
But this is an excellent example of the power of challenges. They are truly assets that live on past their initial use case.
In this example, we have a Challenge that has simply been repositioned from a paid challenge to a premium for a membership club.
So it’s a classic example of leveraging assets that you have already created to continue to provide value for you, even years after their creation…
…years after they have made TONS of money for you…
…they can continue to work for your business, like automatic machines BUILT for growth and action!
