8 Fears Every Creative Entrepreneur Experiences on the Path to Success


When starting a new project, you deal with a lot of obstacles.

The web design you outsourced might not function how you wanted, or the first shipment of products come in completely the wrong color or size, or your plans for a successful launch don’t pan out the way you hoped they would…

All of these are difficult to deal with.

They hurt, they're painful, and they disappoint us.

But they won’t break you.

What Can Break You

Negative self-talk propaganda, on the other hand, just might.

Negative self-talk propaganda will use these events to make you question yourself, your project, and your resolve.  Negative self-talk propaganda will try to break you were you are weakest: from the inside.

The following are 8 fears we all experience on the road to creating something worthwhile...

1. Fear of Failure

We’re all scared of not living up to our own expectations; we’re even more terrified by not living up to the expectations of others.

So, we rationalize: If we don’t start, we can’t fail.

The simple solution is to not begin your project and to avoid doing the difficult, creative work of building a business, brand or organization…of course, if that’s your choice, nothing happens.

The possibility of failure is a good thing – it means you’re doing something that matters, something original, something rebellious to the robot factory.

If you’re scared it might not work, good – you’re on the right track.

2. Fear of Shame

Worse than the idea of not succeeding is the idea of friends and strangers belittling us for what we’re trying; that because we don’t live up to expectations, we embarrass those with whom we associate (and bring shame on ourselves).

Shame is the greatest weapon of the Enemy and will break you faster than anything else.

Shame is entirely fabricated in our minds.  It has no power but what we give it, no legitimacy but what we allow it.

Keep doing the work.

3. Fear of Being a Phony

Let’s be honest – anyone trying something new feels like a phony.  If you don’t, you’re probably doing something you already know how to do, which means you’re not creating anything new.

Feeling like a phony is a good thing; when you have these thoughts, recognize them as the compass they are – pointing you in the right direction (toward something new).

Keep going.

4. Fear of Pain

Creating something from scratch is painful.

It’s never easy.

Sure, there will be moments when we’re in flow and things just click – and, often, the process of creating is a lot of fun – but those are the highlights.

The pain begins when the flow ends and you’re left without inspiration or motivation, and no guarantee it will work.  That’s when commitment comes in – if you’re committed, you understand this is part of the process, and you keep creating, no matter how hard it becomes.

Before you start, commit – and recommit every day to doing the important work.

5. Fear of Being Hated

This ties into the threat of shame – every person wants some form of validation and the idea of being hated unanimously terrifies us.

Of course, no one is hated unanimously; there will always be someone who loves what you do and appreciates how you do it.

The fear of being hated is entirely irrational; laugh at it when you start your work today.

6. Fear of Being Ignored

Let’s face it, being ignored is more likely what will happen with your project.  There are too many choices, too many options, and a limited amount of time for people to make these choices.  You’re stuff, whatever it is, competes with the noise of the world.

Attention and trust takes time.  So if your stuff is good, stay gritty.  If it’s not good, make it great…and then get gritty.

Note: being ignored is one of the greatest assets of the “newbie.”

If you start with peoples trust and attention, you’ll be compelled to keep that trust and attention.  Usually, this involves doing whatever created the trust and attention in the first place.

The result?  Sameness.

But the “newbie” – he has no fear of doing what’s worked, because nothings worked yet.  The “newbie” is really another name for the underdog - the insurgent.  The actions of the underdog challenge the status quo; the actions of the insurgent create revolutions.

Don’t worry about being ignored – it’s more likely you'll create a revolution (if your stuff is good enough).

7. Fear of Loneliness

Creating involves some level of introversion.  If what we’re doing is brilliant and personal, we need to wrestle with ideas internally.  And dealing with things alone is no joke.

It’s difficult to fight a battle by yourself.

Don’t cut yourself off from external help.  Don’t let the lonely abyss of creation overwhelm you.  The solution is usually just a friendly talk away, or knowing others are in the trenches with you, willing to help you through your difficult times.

Talking out a problem with someone you trust is one of the surest ways to get unstuck.  Use this technique freely; use it often.

8. Fear of Rejection

And after all the pain you’ve gone through, “they” might reject you.

If you expect your next project to be the breakthrough moment – the thing that changes everything so you no longer have to face rejection - I have bad news: this never happens.

The most popular, famous, successful businesses still face rejection.  Sure, once you’ve hit a tipping point of fans and support, rejection is less likely because the majority will always mimic the majority (a self-perpetuating cycle), but even great brands, bands, and people fade away if all they do is perpetuate the current cycle.

Continue to challenge everything; continue to create new things; continue to be rejected for your unique work – it means you’re doing something right (and the few who understand your work – the important people – will continue to support you).


Every tactic and tool used by the Enemy is conquerable.

When you know these 8 fears are just part of the price you pay for attempting something new, different and bold, you can overcome them.

Now that we know what we’re in for, you have two choices:

1)    Stop.

There’s no reason to start in the first place if you have no intention of finishing (and shipping).  And if you don’t think you can deal with the fears above, better to be realistic in the beginning instead of wasting months (years) of time.

2)    Go.

Anyone can do it.

Few people choose to.

And that’s entirely on you.

My suggestion?

Never fight alone:

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2 comments on “8 Fears Every Creative Entrepreneur Experiences on the Path to Success”

  1. Tom,

    Great post. Valuable content, Unique perspective, Timely Advice.

    This is why you are a leader and why you will continue to be successful.
    Keep up the awesome work. Can't wait to see what you SHIP this month.

  2. Alan, thank you so much! Comments like that are so humbling - I hope what I ship meets expectations!

    Look out for the Gunslingers Guide and Workbook tomorrow 🙂