Stop Stopping Yourself : 5 Reasons You are Your Dream's Biggest Obstacle


After years of creating things myself, and meeting lots of other people who love to create, want to create better, or want to start creating, I’ve found one commonality between everyone:

We all face an invisible gap that stands between us and the ideas we want to accomplish.

It’s almost as if we find ourselves standing on one side of a huge canyon, and on the other side is our future self, being awesome, inspiring, and creative. The only problem being that we can’t see the bridge to get there.

It’s ironic how exciting it is to get an idea, tell others about it, imagine how amazing it will be and how incredible it will feel to be there- only to be overwhelmed by this immense, crushing intimidation once we decide to actually start.

I find it weird that the tiny mindset-click going from, “I want to do this.” to, “I’m GOING to do this.” suddenly causes many of us to freeze up.

Why is that? One reason may be that it’s easy to have a dream, but it COSTS us something to pursue it. And once we start, we’re not sure if we have enough in us to pay that cost. [Spoiler: Most of us DON’T have enough in us to do it when we start, but it’s something that we earn as we grow. Our ability/knowledge/skill/wisdom expands with experience. It’s not free – you have to earn it through action.]


A year ago I decided to do something I’ve never done before: Teach a creative workshop.

So I took the leap: I made the event on Eventbrite, came up with a name, designed graphics for it, wrote the vision, came up with pricing for it, prepared to share it for the first time on Facebook… and hesitated.

Even though I have done public speaking for years, and had many creative conversations and love to encourage others, I wasn’t sure if anybody would want to pay to come and hear me speak at something I facilitated myself. I doubted my own ability to draw a crowd. I doubted whether anybody would see me as credible. All my other times speaking it was for someone else’s event, to a crowd who came for the event that I was merely a guest speaker for, sharing on a topic that was in line with the direction they were already going. This would be the first time I would put myself on the line completely, sharing my ideas, hosting my own event, marketing myself, and asking others to not only come, but to pay money for admission to the event. It was a gamble to have people put some serious value on the workshop… and by reflection, myself. I was making myself completely vulnerable.

I spoke with my wife, Shannon, about how I was feeling and she reminded me why I was doing this in the first place: to help others do what I’m trying to do, sharing from my experience rather than mastery. The whole purpose was to treat it like an experiment, to create a class, then spend the month before pursuing a goal (writing the first draft of a book in my case), and finally share about the process for the workshop. – So I took a deep breath, and clicked “Share” to make the event official.

Now it was “On”! Now I was accountable. Now the process starts.

There was a long list of fears rushing through my head that I had to face. Thoughts like:

  • Who do I think I am trying to teach others?

  • I’m not a good speaker.

  • People won’t want to pay money to hear me speak.

  • People will think that it was a ripoff.

  • People won’t come.

  • I won’t know what to talk about.

  • I won’t have enough stuff to make it worth their time.

  • I can’t compare to the other design classes and workshops.

These were all obstacles standing in between me and completion, so I had to take them on one-by-one, journaling and thinking, and dismantling the fear with the truth of what I knew about myself and what I was doing.

What came out of this process of “Fear-Setting”, as it’s called in The Four-Hour Workweek (more below), was an understanding of and tools to dismantle some of the biggest obstacles that I was facing. These obstacles are common to a lot of other folks who set out to chase a dream.

It’s said that you can’t take anyone where you haven’t personally been, so I went out and got the experience. This post is a tried-and-tested product of my personal dream-chasing, fear-fighting, action-taking, self-overcoming process.




5 Reasons You Are Your Dream's Biggest Obstacle

I don’t want to share about “How to accomplish your dreams.”, but rather “How to stop NOT accomplishing your dreams”.

There is enough knowledge out there to point out that learning the steps and getting the direction to move forward isn’t the problem. And when it comes to ability, we often have the skills to make the first steps because it is something we are already passionate about. However, with all the know-how at our fingertips and the ability to take at least baby steps forward, for some reason we STILL don’t take action. This can be very frustrating and discouraging.

The problem isn’t so much that you are currently doing things you don’t want to do, but that you’re NOT doing what you MOST want to do.

You’re trading lesser wants that are more comfortable for things that you truly, deeply, desire to accomplish in life. (Ex: binge-watching movies on Netflix, memorizing trivia about movies and video games [Just me?], filling all your free time with hanging out, scrolling through social media, etc., instead of writing, teaching, speaking, traveling, creating, becoming financially free, improving your health, getting fit, etc.)

The answer is simple: "Take action!" – Right?

Well, yes, but it’s not always that easy.

In order for you to take action, you’ve got to be aware of the obstacles that you are facing.

And these obstacles are present whether you’re aware of them or not- like an invisible wall that you'll keep banging your head against. Knowing your personal obstacles can be the difference maker between you getting frustrated and quitting, and you making consistent and significant progress toward something you greatly desire.

So what are these obstacles?

There’s a lot of different kinds of obstacles we face, but I’ve come up with some of the biggest ones out there, especially for those pursuing creative goals. My hope is that I can help you identify some of the things that are in your way, so you can start getting started.


1. Fear

The oldest and strongest emotion of mankind is fear, and the oldest and strongest kind of fear is fear of the unknown.
— H. P. Lovecraft

The first, and biggest obstacle any and every one of us faces when pursuing our dreams is fear. 

It manifests itself in so many different ways, but it lies at the heart of most of our biggest obstacles. Fear keeps us from taking risks, makes us think we aren’t good enough, worries us that no one will show up or read what we’ve written or listen to what we have to say.

Fear’s primary aim is to stop us before we get started.

Fear is the bird that snatches up the seed of vision before it has a chance to settle into the soil and grow. Fear comes from a lot of different places: our own insecurities, other people’s influence on us, past experiences that we don’t want to relive, inexperience, etc.

Most people will choose unhappiness over uncertainty.
— Tim Ferriss

In order to overcome Fear, the important thing you need to do is understand Fear's nature. – Fear thrives on vagueness and uncertainty. If we don’t know how to combat it, we can give Fear permission to hijack our imagination and crush us with a mountain of “What-ifs”.

Have you ever felt overwhelmed with a million things swirling around in your head, but if you tried to be specific, it would be hard to pinpoint what exactly you’re so worried about? That’s the “fear cloud”, my friend, and it’s big and messy. But if you choose to have the courage to walk through it, you’ll find it doesn’t have much substance.

Fear’s greatest strength is in it’s perception.

We need to bring ourselves to make the distinction between the perception of our fears and the reality of our fears. We need to challenge it. And yes, we’ve heard the “Face Your Fear” proverb before, but there’s a difference between knowledge and application. There’s a huge difference between knowing you should face your fear and actually FACING your fear.

Defining your fear removes it’s power.

To get where you want, you need to develop the practice of calling out your fear and telling it to make good on it’s threats. And what happens is that under challenge, 99% of our greatest fears wither. And the other 1% that may happen, are almost never as bad as we thought they were going to be. Fear is a lot like the Wizard of Oz: A lot of smoke and mirrors and loud shouting, but behind the curtain it's actually much smaller than it appears to be. This brings me back to the practice of Fear Setting I mentioned before.

[PRACTICE] Fear Setting: 

Sit down and define what you are most afraid of. Write out the absolute worst case scenario. Then hold that up against a realistic perspective of more likely outcomes. 

Click link on right to download PDF

Click link on right to download PDF

(Download Fear Setting PDF)

I’ve borrowed this from The Four Hour Workweek by Tim Ferriss, because this process of deconstructing fear is what helped me to get past myself and actually write the first draft of my book this year as well as put on the creative workshop, despite being totally scared to do it. This process will help you DO what you want and stop NOT doing what you want.

"Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember our rule of thumb: The more scared we are of a work or calling, the more sure we can be that we have to do it." – Steven Pressfield

The speed with which you decide to overcome your fears and insecurities dictates how quickly you can advance to the next level.  

You could spend a day, a year, or a lifetime overcoming a single fear.


2. Zero Account-ability

Accountability breeds response-ability.
— Stephen Covey

One of the reasons we don’t take the steps to challenge our fears is that we have no accountability. And I’m talking about real accountability: telling someone or committing to someone whose opinion of you really matters.

Being accountable to yourself is good, but most of the time it’s not enough.

Why? Because you are too used to letting yourself down.

Many of us compromise on an almost daily basis.

Solution: Get some EXTERNAL accountability.


A.) Be accountable to a leader/mentor.

Mentors can speed up our growth process because they can steer us around the mistakes and obstacles they had to face so that our journey is more streamlined. They can distill knowledge and lessons for us that took them years to acquire and earn, and they can give us advice and direction that helps us to refine our abilities and skills at an advanced pace.

How to get the Dream Mentor:

Think of someone who you respect and admire. Someone who you would love to learn from. If you could only have this person pour out their wisdom on you, then you could bask in the sweet waters of success...

Chances are that person has written a book. (Or blog, etc.)

Get the book. Read the book.

These people write books to share knowledge that took them decades to acquire. They also write books because it’s impossible for them to have 10,000 conversations with 10,000 different people to teach them all that stuff.

If you don’t have a mentor when starting, let books be your mentors. Plus, you wouldn’t want to meet that person, ask them a question and have them say, “Have you read my book?"


B.) Be accountable to your peers.

it's okay to learn from peers. 

It's easy to learn from mentors because we already know that we don't know as much as them. So it's easy to be humble. But with our peers, we really want to be respected by them and we really want to look like we know what the heck we are doing.

But it’s crucial that you have people you feel safe enough with to admit that you have no idea what you're doing and can ask them how they think you could grow. These kind of relationships are something that you have to seek out and build personally. You probably already have some of these people in your life, you may have just never utilized them in this way. They are people who love you, who you know to be loyal and honest, and who you are willing to get challenging input from without being offended. Transparency between both of you is key.

It's easier to receive critiques you ask for personally rather than get unsolicited advice.

The reality is, you are going to get feedback either way. But the only way you will know what voices to listen to and which to write off is to have a close community of trusted people who you’ve given permission (either verbally or not) to give you constructive feedback. Otherwise it will be too easy to focus only on the hurtful criticism, or even your own self doubts. And it is self doubt that steals your momentum more than anything else.

The dreams you have are so delicate that you have to steward them.

You have to position trusted people around you on each side to help you protect your dream. Otherwise the winds of reality and circumstance will knock you over. Bringing in peer accountability is something that protects, never threatens, your dream.

It doesn't mean you're weak to ask for help. It means you are wise.

Only those who are weak think they can do it on their own. They try to build on their own and they fail on their own.

In the case of accountability:

"We" is greater than "I".


C.) Raise The Stakes

Another additional form of accountability you can stack on top of these first two is setting stakes. Essentially, this means putting consequences in place for you if you DON'T accomplish your goal. This works best when you involve other people in carrying out the consequences for you.

A couple examples:

  • Healthy Peer Pressure - Share your idea and the actions you need to take with a few close friends and tell them that you're sharing it with them because you want to be accountable. Pick people who you know well enough that you will see them often and who aren't afraid to tell you what they think. Not only can they help you stay on track by checking in to see how it's going, but they can often be some of your biggest supporters.

  • Social Pressure - Social media can be a great source of public accountability. Making an announcement to do something in front of an audience of hundreds, or maybe thousands of people activates one of our strongest desires: to be approved of and respected by our peers. We set social expectations for ourselves, which are very powerful.

  • Put money on it - One of the most powerful motivators out there is the desire to not lose money. Studies have shown that the pain of losing money is much greater than the satisfaction of winning money. If you really need a kick in the butt, put a painful amount of money down on the bet with a friend. $50-100 is normally enough sting to motivate you to finish strong.

Accountability is crucial for follow-through.


3. Zero Deadlines

A goal is a dream with a deadline.
— Napoleon Hill

You can do a month's worth of work in a month or you can do a month's worth of work in a year.

Last year, I made up my mind that I didn’t want to spend a year TALKING about writing a book, I wanted to spend the year WRITING a book. So I sought a deadline and talked with my wife for accountability and clarity, and decided upon March 1st - FIRST DRAFT of book and first Workshop.

Deadlines should feel like they’re a little too short for you to finish.

The pressure is good. If a deadline gives you more than enough time to finish, it’s not a deadline. It’s just a line. And you will use up all your time doing other things, then cross the line and have to set a new one again.

Deadlines are a form of accountability that we create with ourself, and they work even better when we let someone else know about them. 

One of the biggest excuses for not pursuing our dream is that we’re “not ready yet”, or “It’s not the right time”, or “If i had THIS, then I could do it.", but the paradox is that we only get to that point of readiness and preparedness AFTER taking action toward the goal. It's the pursuit of the deadline that provides what we need.


If you're not familiar with the term, it means thinking that reaching a certain level or place is the only thing you need to become a success. – "If I only had a better camera then I could start my Youtube channel."  or "If I only had the amount of followers THAT guy has, then it would be easy to write my book." or "If we made money like that couple then we could go travel to Europe." – And what happens is that the gap between where you are and where you think you need to be becomes one of the biggest excuses why you shouldn't even bother starting at all.

You can have a vision without the resources, but you can't expect the resources to produce vision.

That’s not how vision is designed to work. Having more doesn't make you more passionate. Sometimes excess breeds laziness. Sometimes having less can make you more passionate because it forces you to work with what you have!

Vision is “a mental image of what the future will or could be like. The ability to think about or plan the future with imagination or wisdom."

Vision always comes BEFORE preparation. You see what you want to do, THEN you prepare for it. “I will climb that mountain”, leads to preparing through training, tools, and knowledge. Setting the deadline for your goal puts an urgency in you to do what is necessary to achieve it.

Waiting is not the same as preparing. It makes the accomplishment of our dreams conditional on our circumstances rather than our personal actions, which is a very risky gamble because it might never come if you just wait.

Preparation - [ACTIVE] - the action or process of making ready or being made ready for use or consideration. 

Waiting - [PASSIVE] - the action of staying where one is or delaying action until a particular time or until something else happens.


Some people spend their entire life getting to Step One. Some people spend one year. Others spend one day.

There are a lot of factors that we don’t have control over in our journey, but the one we have the greatest control over is our personal pace of action. The quicker pace we can take action, the quicker we grow, learn, and progress toward the dream.

Setting deadlines MAKES you ready.

Setting deadlines MAKES it the right time.

Setting deadlines MAKES you GO and GET the things you need.


4. Distractions

Looking at art is not the same as making art.
— Frank Chimero

Talking about making art is not the same as making art either.

There are the obvious distractions, like social media, keeping yourself busy, the responsibilities of life... and then there are distractions that are much more sneaky.

One thing I particularly struggle with is telling people about what I want to do versus actually doing it. – I get really excited about an idea for a project and then I share it with some friends, and then they tell me how great of an idea it is and say, "You should totally do that, you'd be great!" And something weird happens: the affirmation of my idea from others feels good enough that I stop there and have trouble following up on the actual idea. Then I reach a point later where I'm like, "What am I doing with my life!? I need to create! I need to follow through!", and I get a new idea, or I tell someone else about the original idea again, and they tell me it's great again and all feels well until the next round of creative self-crisis strikes. Maybe you can relate?

A few months ago I was telling my wife, Shannon, again about how I want to start a blog and she stopped me and asked,

"How many more people do you need to tell you that this is a good idea before you actually DO it?"

Ouch. She called me out, and I'm grateful she did because it helped break me out of my loop of "Get Idea- Tell Others- Receive Validation- Don't Follow Through- Feel Guilty- Tell Others- Receive Validation- Don't Follow Through- Feel Guilty- REPEAT."

Often times we do things that give us the feeling of productivity without actually being productive.

I was settling for a feeling of satisfaction that was lesser than the satisfaction of actual accomplishment. Ask yourself, “Am I doing this thing right now to avoid doing the thing I really should be doing?"

I am now very discerning about who and when I tell people about a project I am doing because I want to be known as a man of action rather than someone who talks but doesn't follow through. I share new ideas with Shannon and then with close friends for the purpose of accountability toward the goal, rather than a pat on the back. I want to tell people about what I'm doing and about what I've done rather than what I am going to do.

Action fuels productivity.

There are two ways to motivate change:

  1. Change your standard, or

  2. Wait till life forces you to change.

Productivity means you produce.

You are being productive when what you do is:

  • Fruitful- Produces Fruit (metaphorically speaking)

  • Constructive- Builds something/someone

  • Profitable- Creates profit

  • Effective- Has an effect. Particularly a Positive one. If it has a negative effect, then you should re-evaluate what you’re doing.

  • Worthwhile- It is worth your while, and hopefully someone else’s too. Meaning that the TIME you spend doing what you’re doing should create VALUE. Time is our MOST valuable resource, so learn to discern the balance between focus time, relaxation time and WASTING time.

  • Helpful - Supportive. Cooperative. Charitable. What you are doing helps people in some way, shape, or form.

TIP: Make a regular practice of asking yourself, Will this make me stronger?"



The reason we struggle with insecurity is because we compare our behind-the-scenes with everyone else’s highlight reel.
— Steven Furtick

It’s so easy to be intimidated and overwhelmed by all the great work out there.

I can’t count the amount of times that I’ve gone online seeking to gather inspiration for a project or idea I want to make, only to be completely blown away by the complexity, scale, and skill of all the beautiful projects out there. I hear my own voice in my head saying, “There’s no way I can make something as good as this…” or thinking, “I’m in way over my head. I might as well not even try." 

And a lot of the time, these thoughts of comparison, in addition to completely distracting me from my mission, take the wind out of my sails and make me feel like a tiny little speck on the global design plate.

These thoughts are common to pretty much every person who is trying to accomplish something new. We think that there is no way we could possibly be the best, or even make a ripple at the very least.

It feels so big out there and we feel so small.

Because we can access all of these beautiful projects done by other people so easily and in such mass quantity (on Pinterest, Behance, Tumblr, etc.), it’s so easy to overlook the fact that these were not created as instantly as we can access them. These were made (mostly) by TEAMS of people, with months, sometimes years of work put into them.

We get intimidated when we only look at the end product and not the process it took to get there.

These people all reached moments of being overwhelmed, intimidated, insecure. They are also in the process of growing and developing. We have to realize that it’s ok to be where we are in our process.

If we expect ourselves to be where someone else is, but don’t understand the process they went through to get there, then we place a burden on ourselves that is no longer inspiring and driving, but rather crushes us. If we keep viewing our journey through someone else’s story, it will never align and we will always be dissatisfied, discouraged, or prideful as a result. At the heart of it is insecurity. It results in us thinking that if someone else does well, that we are somehow lesser as a result.


What is your primary goal?

Is it to make a good book/project/film/business to communicate something important and impact people? Or is it to make something that other people will give you props for and nurse your ego?

80/20 - We spend 80 percent of our time trying to create our project for 20 percent of the people. It’s probably actually closer to 90/10, or even 95/5. We spend 95% of our time trying to impress 5 percent of the people. And most of the time, those people aren’t the ones who need our idea. It’ the other 95% of people who need our book/idea/product/etc. but we get discouraged because we can’t make it good enough for the 5%

Accept that your idea is not for everyone, but it IS for someone. – Make it for them.

This is so freeing to remember when I lose sight of my goal.

Answer this question for yourself honestly: "Where do I find my fulfillment?" Is it other people's opinion about what you create, or in the process of creating itself?

If our fulfillment is conditional on other people’s opinions, then we will never be satisfied in what we do.

We should never be more motivated by our insecurities than by our passion. Do you want success to nurse your insecurities, or to create value in other people’s lives?

Don't compare. Remember the heart of your vision and stand on it.


Trust The Process

Let your process be your process. But through that process, work to become aware of your inner obstacles and let them get worked out as you pursue your passion.

  • Challenge and conquer your fears (this is an ongoing process that happens in layers).

  • Gather a community of accountability around you and take leaps that force you to be accountable to your goals.

  • Put a deadline on your goal and make use of healthy time pressure.

  • Remember that having vision for where you want to be comes before you ever feel prepared, and feeling prepared is a concept that always grows as your goals grow.

  • Identify ways that you are allowing distractions to suck your motivation, and don't take the bait of sounding impressive over actually producing results.

  • Lastly, regularly adjust your perspective when looking at others' journeys. Don't compare your story with anyone's but your own.

It can be easy to lose sight of your goal. The reason you wanted to do something in the first place gets lost in the mishmash of things that have yet to be accomplished. But if you remember this, you can keep your head on straight and give yourself enough grace to take each step one at a time.


The outcome isn't the goal. The process is the goal.