Why Some Entrepreneurs Almost Always Move Towards Their Goals (And Others Fail Miserably)

Photo by Lindsay Henwood on Unsplash

You’re just one tweak away from gaining massive leverage.

Do you struggle with building momentum and moving towards your goals?

Does it feel like you’re always taking two steps forward and one step back?

This is extremely frustrating. You set ambitious goals that’ll change your life. Maybe the goal also changes the lives of others…

Arriving at your destination would mark this achievement and provide you with all the benefits that accompany it.

But as you start setting out on your journey, it gets more challenging. Obstacles left and right…

Then self-doubt kicks in, “Am I moving in the right direction? Am I good enough? Should I try something else?”

And then maybe we find reasons to give up and move to the next project or campaign.

Initially, we’ll rationalize why this is a good decision. But eventually… we regret not following through and figuring it out (if it truly was a goal worth achieving).

Because what if you accomplished it??

I mean… imagine how life would’ve been different if you followed through and achieved your goal!

Fortunately, there’s a simple tweak that you can use that’ll ensure that you WIN NO MATTER WHAT… yes, even if you don’t “achieve” your goal.

I’m talking about creating an environment so that no matter what the outcome is… you can always grow and improve.

And if you start implementing this tweak as a habit, you’ll notice quick improvement.

In this article, I’m going to share how successful entrepreneurs approach achieving goals (here are some that I’ll mention: Scott Adams, Tim Ferriss, Jason Harris, Cal Newport & Ryan Holiday).

Are You Setting Yourself Up For Success (Or Failure)?

If you’re not making much progress towards your goals, the issue may be in the approach.

Many successful individuals have an intentional way of planning their goals and moving towards them (I’ll mention a few in this article).

They look beyond the immediate outcome and play the long game.

Let me ask you: What if you could create goals and move towards them in a way that didn’t stress you out?

I’m suggesting that a little tweak in your goal-setting approach will allow you to:

  1. Enjoy the process more.
  2. Maintain your interest in the pursuit of your goal (instead of getting bored and quitting).
  3. And get better results!

In goal-design theory, there are a couple of ways to create goals.

In this article, I want to talk about performance goals and mastery goals.

The type of goal you choose will improve your ability to grow and achieve it.

Let’s Start With Performance Goals

These are the goals that are usually contingent on an outcome: “I want to make a million dollars. I want to improve conversion rates by 50%. I want to capture 1,000 leads this month.”

The key characteristic of this goal is that you’re trying to DEMONSTRATE that you’re competent in a certain domain. This could mean demonstrating that you’re competent to others, or yourself.

This doesn’t mean those performance goals are less effective.

But the science suggests that people who ONLY have performance goals usually lack the motivation and discipline to achieve them.

This is because what’s motivating them is external (for example: status, money, and validation).

This may sound negative… but I think having these types of goals can be effective, as long as you pair it with the next goal type.

Mastery Goals

And then there are mastery goals.

These are goals that you pursue to build different skill-sets and competencies.

For example: This is what a mastery goal looks like for me:

My external goal is to generate more revenue and grow my business. More specifically, this means teaching & coaching entrepreneurs on how to get more leads and grow online.

However, if I shift my focus to mastering the skill-set of being a better coach and teacher, I’m much more likely to take consistent action that’s congruent with that intention.

So my focus becomes less about the short-term outcome and shifts to long-term benefits.

For this type of goal to be effective, you’ll want to align it with your business’ mission, your core values & overall purpose. For instance, I believe coaching can change people’s lives & facilitates growth. And one of my core values is to create a positive impact in the world.

This falls in alignment with mastering the skill-set of being a better coach and teacher.

And once they’re in alignment, you shift the focus towards mastery (I’ll explain a few practical tips on how to do this further in the article).

If your intention was solely based on getting more revenue, you’d put less emphasis on building out your skill-set. And ironically, focusing on building out your skills would result in more revenue anyways!

Instead of judging your performance based on short-term outcomes and results (which you may or may not achieve)… you’re basing your performance on the actions themselves & your progress towards mastering those skills.

In essence, we’re talking about finding intrinsic motivators instead of only relying on external motivators.

Why is this important? A couple of reasons:

  1. We tend to have stronger motivation when we’re driven by intrinsic factors.
  2. When we focus on growing our skills in a meaningful way, we tend to take action that has a greater impact (compare the impact between sending out a few emails VERSUS taking the time to write a powerful piece of content for your business)

This isn’t to say you shouldn’t focus on achieving a short-term goal or engage in lower impact activities.

That’d be ridiculous, especially for busy entrepreneurs and marketers.

However, I’m proposing that shifting the intention towards mastery will encourage long-term results over time. And it’s important to schedule time to engage in tasks that nurture moving towards mastery.

And utilizing both performance and mastery goals will help you move towards your goals quicker.

How To Create Wins (Even If You Fail)

Photo by Japheth Mast on Unsplash

“Losers have goals. Winners have systems.” — Scott Adams

In a Tim Ferriss interview with Scott Adams (creator of the Dilbert Comic strip), they spoke about this idea of having goals versus systems.

When I first heard this concept, it felt like my brain was installing some powerful software!

And it’s Scott Adams’ approach for moving towards mastery.

His approach to achieving his “goals” is to actually develop a system that guarantees success.

He proposes to engage in habits and projects that’ll give you transferable skills and/or relationships (even if you fail).

To help illustrate this idea, let’s use a focusing question to help us develop a “systems-oriented” goal.

Ask yourself…

“What goal can I create for myself that’ll allow me develop my skill-sets or build relationships… even if the endeavor is a complete failure?”

Notice how powerful this question is.

This forces you to stop fixating on the short-term results since most projects you start won’t give you immediate returns anyway.

So instead of feeling discouraged that you’re not getting all the immediate results you want (and quitting), you embrace the process of moving towards mastery because you created a system.

This system ensures that you improve and grow over-time.

Personally, this is my approach for being an entrepreneur, coach & online marketer.

I DO NOT focus on the following… “I’m going to make x amount of $$ this month” OR “I’m going to capture x amount of leads”…

Don’t get me wrong, I’m definitely trying to generate more revenue & leads. I’m aiming to move in that direction. However…

I try to focus on the following question, “How can I develop my skills as an entrepreneur, coach & marketer WHILE ALSO moving towards my goals?”

This shifts my focus to take action on HIGH-IMPACT activities that’ll help me grow over time.

Similarly to Scott Adams & Tim Ferriss, I still have revenue and lead generation goals… but I shift my focus to systems-oriented thinking.

Jason Harris on “Skill-Hunting” And Why It’s Crucial

In his book “The Soulful Art Of Persuasion”, Jason Harris talks about a concept he calls “skill-hunting.”

This is his version of moving towards mastery.

Though the purpose of his book is about how to be more “soulfully” persuasive, I believe it compliments this article.

In his book, he suggests that if you change your work from “tasks” to “skill-based processes”, you not only move towards your goals quicker… but you also become more trustworthy.

This is huge if you’re an entrepreneur and a marketer trying to achieve your goals.


Because if you’re looking to achieve something, you’ll also need to become a trustworthy person in your industry. If you don’t earn trust, you’ll have a hard time persuading people to become leads, customers, or become apart of your company in any way.

Really let this following sentence sink in:

We’re all drawn to people who have exceptional influence, even if we don’t know much about their character.

If you think that’s nonsense, then consider this…

In his book, Jason Harris notes how a recent study asked Americans to name the most trusted person in the country. And guess who was at the top of the list?

Tom Hanks! I thought this was super interesting.

Though he seems like a genuine guy, I don’t really know much about his character. Do you?

But what we do know is that he’s an amazing actor!

We tend to trust very skillful individuals because they’ve demonstrated that they have the will and tenacity to move towards mastery.

This is because we’re drawn to the pursuit of excellence, as it’s a window into the human soul.

People who are skillful put in the work to do things well and properly. And they avoid cheap workarounds.

Corporations acknowledge this phenomenon, which is why celebrity endorsements and influencer marketing is so popular.

And if you’re skillful enough… then you’ll reap the rewards. Consider how Michael Jordan is still helping sell sneakers in 2019 and made roughly $145 Million through all his endorsements.

It pays to be skillful.

Start Moving Towards Mastery

Photo by Ravi Roshan on Unsplash

So now that you understand this idea of “mastery” and “systems-oriented” thinking, how can we start applying these concepts in our day-to-day lives?

Align Your “Mastery” Goals With Your “Performance” Goals

Look at all your current goals.

Are they all performance-related? Are they all based on external outcomes?

If so, try to find ways to restructure the goal so that you’re also moving towards mastery.

If you’re an entrepreneur, maybe your goal is to improve your marketing skills. Or maybe you want to improve your ability to coach and teach. Perhaps you want to improve your sales skills.

Engage in Deep Work

In Cal Newport’s book “Deep Work”, he notes that there are two core abilities that someone needs to thrive in our economy:

  1. Quickly mastering hard things.
  2. Being able to produce at an elite level.

And the best way to achieve both of these is by engaging in “deep work”.

Since we’re so distracted and “busy” nowadays, many people don’t work deeply on creative output.

And over time, this is a weakness (especially since our current economy rewards mental labor over physical labor).

His formula for achieving this is: high-quality work produced = (time spent) x (intensity of focus).

Don’t let the simplicity of this formula take away from its power.

And from personal experience, engaging in deep work activities usually means you’re engaging in mastery and systems-oriented goals.

So here’s a quick tip: Schedule time in your day to focus on creating lots of value.

Here are some examples:

  1. Maybe that’s focusing an hour every morning to write your book.
  2. Maybe you want to focus on developing content for your new online course.
  3. Or perhaps it’s coaching one person every day for an hour.

Over time, your skills will improve and your results will follow.

Alive Time Or Dead Time

Ryan Holiday talks about this concept of alive time versus dead time.

We tend to think that we’re too busy or lack the resources to move towards mastery and engage in deep work.

We all have different commitments and busy schedules (some busier than others). But if you truly want to achieve your goals and move towards mastery, there are creative ways to squeeze in more time.

And this is alive time.

Maybe this means waking up an hour earlier to create content for your business or writing that sales letter.

Maybe it’s sitting down to produce high-quality work in between meetings or obligations.

Or maybe you spend one less hour watching Netflix.

Once you’ve identified when you can engage in deep work, it’s time to double-down! ;)

Next Steps: Join The Optimized Way Journey

Feeling stuck as an entrepreneur or marketer?

Today’s information overload doesn’t help.

Which content will help you achieve your goals? And which ones won’t?

Maybe you’re able to sift through a sea of useless information to find a few gold nuggets… but you’ve wasted so much time. And the results were minimal!

You have a business to grow… and your time is very valuable.

I created my newsletter as a solution to this. It aims to help you avoid wasting your time on online marketing information that doesn’t work (or has a very small impact).

Join my free newsletter HERE where I share tips and actionable advice on how to improve your business through online marketing.




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Colton Hicks

Colton Hicks

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