You Won’t Know, Until You Try

You won't know, until you try

Updated: July 21, 2023

Have you been thinking about starting something lately?

Perhaps you have been thinking about starting a blog?

Or maybe you have been thinking about trying your hand at an Etsy shop?

Or rather than writing or entrepreneurship, you simply want to try yoga, tennis, golf, pickleball, meditation, or some other hobby?

Well, what is stopping you?

Why haven’t you done it yet?

I probably don’t need to tell you this, but fear is stopping you.

We are all afraid of failure, embarrassment, and mostly we are afraid of looking stupid to ourselves and others.

And that is what is stopping you.

Fear of failure.

There is only one thing that makes a dream impossible to achieve: the fear of failure.

Paulo Coelho, The Alchemist

I know that for a long time, I was hesitant to start a blog, because here I was thinking to myself “why would anyone want to listen to you?” and “what value to you have to add to the FIRE conversation?”

And I was hesitant for a very long time. For many years while I was building a $15M a year business, I had dreamed of blogging, podcasting, and eventually writing a book.

In the end, though, I didn’t pursue any of it due to time…and if I admit it to myself…fear of failure.

Yet, after my 6 month mini-retirement, I finally worked up the courage to do it.

And a short 10 months later, I’d written a guest post for JL Collins, been featured in interviews by several other blogs, and was a Plutus Awards Finalist for Best FIRE Content and Best New Personal Finance Blog.

And that is all within the first year. What the heck was I afraid of?

Since then, in the second and now third year, the blog has been featured in more and more places, my email list is fast approaching 1,000 subscribers, and my Twitter account has taken off!

Moving past fear of failure

We are all afraid of failure.

It is a gift given to us by natural selection. In life-or-death situations of early humans, having a lot of fear was not only really healthy, but it literally kept you alive.

The fact that we are not living in a “natural” environment makes our feelings even less reliable guides to reality.[…] the modern environment can take various kinds of feelings that served our ancestors in this Darwinian sense and render them counterproductive in the same sense.

– Robert Wright, Why Buddhism Is True

So being afraid of failure, avoiding uncomfortable situations, and/or putting yourself out there, it is 100% natural.

In fact, we wouldn’t be innately human if we didn’t have this particular quality.

But we are not living in a “natural” environment any longer. You don’t need to be fearful of trying something new. Your life is not in the balance by trying something new (unless you are skydiving or engaging in some other high-risk behavior).

But how do we overcome our very own human nature?

Accepting that you will fail

Awhile back, I wrote about and listed out my failure resume, both professional and personal.

The sure number amount of times that I failed at something is almost laughable.

But ultimately, failing is the way.

When you fail, you are truly living life the way that it should be lived.

If you aren’t failing, or at a bare minimum, willing to fail, then you are hiding in fear.

We cannot escape fear. We can only transform it into a companion that accompanies us on all our exciting adventures….Take a risk a day–one small or bold stroke that will make you feel great once you have done it.

Susan Jeffers

Failure is a part of life. But by embracing your failures, looking them in the eye, and ensuring that you learn from your mistakes, you will do better next time.

A good quote I like to remind me why I should face my failures is from Steve Jobs’ Stanford Commencement Speech in 2005:

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything—all external expectations, all pride, all fear of embarrassment or failure—these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”

Steve Jobs – Stanford Commencement Speech 2005

Life is short. We’ll all be dead soon. A little failure isn’t going to change that fact. Neither will success for that matter. So what are we all waiting for?

Accepting that you will fail, is the first step.

Then you have to actually start.

Just start – no one knows what they are doing in the beginning

For a long time, I have been willing to accept failure of some sort.

Without that acceptance, I wouldn’t have started and sold companies or attempted to do things that I had literally no idea how to do when I started them (learning to code for example).

And it is not just me. None of us know what the heck we are doing.

The best thing you can do is just start.

You’ll figure it out along the way.

Inaction breeds doubt and fear. Action breeds confidence and courage. If you want to conquer the negative elements in your life, don’t sit at home and think about it. Go out and get busy!”

— Dale Carnegie

As Dale Carnegie says, “action breeds confidence and courage.”

Once you leap into action by starting, you’ll figure things out.

Learning from failure

In the end, you’ll learn more from trying and failing, than never having tried at all.

Try -> Fail -> Learn -> Repeat.

Then one day you’ll eventually harness all the power of your failures into confidence, persistence, and eventually success.

You won’t know, until you try

You won’t know if you’ll be a good golfer.

You won’t know if you’ll be a good blogger.

You won’t know if you’ll be a good writer.

You won’t know if you’ll be a good entrepreneur.

You won’t know if you’ll be a good investor.

But hell if I will go down without giving it a try.

You’ll never regret giving it a try.

So get out there, and keep on failing!

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  1. Ah, you’re in the sweet spot of growth and it’s only of the best feelings. Congrats on your success!

    I’ve decided to write and publish a book with Penguin Random House, because I figure why not try. If the experience is terrible, and or the book is a failure, it’s OK because at least I know I tried!


    1. 100%. I’ve never regretted trying anything, even if it “failed” – I’m not even sure that it truly is possible to “fail,” because like you said you are just in the sweet spot of growth as a human when you are really, truly, trying.

      Side note – I am excited to see what direction you are taking the book. LMK if you want me to check out an advance copy at any point.

  2. I needed to hear this advice 2-3 years ago when was putting off starting my blog for these reasons, LOL.

    Well said, and I 100% agree with the sentiment. Fear of failure is such a huge hurdle to get over. I’ve put off so many things because I was afraid of failing. Thought that I could protect myself from the rejection or disappointment that would come with failure if I just didn’t try for something at all. Clearly, a limiting mindset.

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