What to do with fear of failure

Safety Cushion
Safety Cushion
Safety Cushion

I am a terrible employee.

I come in late, leave early, use company time to work on personal projects, and watch the clock. I quit before I get fired because I know it’s coming anyway.

In employee-land, I don’t fit very well. But, that didn’t stop me from trying to make myself fit.
I told myself I just needed to find the right JOB.

A job with the right amount of mental stimulation, pay, and flexibility. I had all of those things with my last employer. Still, I did all of that same bad acting and quit short of two years.

You know. Before I got fired. 

I was looking in the entirely wrong direction for happiness and fulfillment in my work-life. I’ve never thought that was too much to ask. After all, so many hours are spent working.


The prospect of a life without meaningful and fulfilling work on my own terms terrified me. I was more afraid of never finding meaningful work than of being without work.

So, I became a Tupperware lady.
Being a Tupperware lady was my first introduction to the concept of entrepreneurship. Work on your own terms and your own schedule. You’re in charge!


As the 22-year-old mom of a breastfeeding infant, I was all in.

I gave the Tupperware thing a shot for a few months—until I lost a bunch of orders and checks customers had given to me. I found them eventually. I had stuck them in a drawer that nobody ever opened.

Some people might take this experience as a sign. A big sign that reads, “Go no further. You are not cut out to be a business owner!”

But, not me. I totally missed that sign. Instead, I was hooked on the prospect of being my own boss.

My entrepreneurial resume is filled with painful failure and experimentation. I was desperate to succeed on my own terms.

At the beginning of each new venture, should I have been afraid of failure?

Yes. Without a doubt.

How did I stop being afraid?

I didn’t. I stayed afraid.

I didn’t spend time trying to eliminate my fears. I never “waited to save up enough money to have a safety cushion” or “waited until the kids were in high school” or looked for someone else’s approval of my ideas.

Instead, I failed big.

Here’s what I did:

  • Wendy’s Hamburgers
    This is where I learned the true meaning of customer service and keeping a clean salad bar. This work was very hard and I didn’t like taking out fast food trash. I still have a check in Ohio’s unclaimed funds repository because I couldn’t bring myself to face my boss to pick up my $19.00.
  • Tupperware Lady
    I told you about the lost checks. I was hooked.
  • Social Worker
    I finished my Bachelor’s degree and got my Master’s degree in Social Work. After just a couple of years of part-time work, I discovered that I really like instant results. I quit social work.
  • Ebay Seller
    Back to being my own boss! I lost more than I made. I went to local auctions and bought stuff to resell on eBay.
  • Specialty Toy Store owner
    I opened a brick and mortar retail store in my neighborhood. I had absolutely no idea what I was doing and made lots of mistakes. This was at a time that it was easy to get an SBA loan. After three years of scraping by, we closed and filed for bankruptcy. It was awful.
  • “Computer Consultant”
    This was a job I made up because I didn’t know what to tell people when they asked me about my work.
  • Politician
    I ran for Ohio Senate. It was a competitive race with full-on television and print smear campaigns. It was so hard on my family. I came in second (which is also last.) My work as a “computer consultant” didn’t help.
  • College textbook sales representative
    This is where a coworker introduced me to my sales hero Jeffrey Gitomer and I fell in love with being a salesperson. I held onto this job for 20 months. But, I didn’t have a job waiting for me after needing a year off of work for two back surgeries.
  • Custom Art Seller
    I feel quite proud of this one. It never made much money but this is a skilled craft that took me a long time to learn and refine. I became the best and most expensive source of this type of art. I recently sold this business for a little bit of money. And, I would not have sold it if I hadn’t found the perfect person to apprentice and take it over.
  • Blogger
    At the same time I started my custom art business, I started a local review blog at bestofcolumbus.org. I thought this would be the real source of my millions. Writing and building on that website is where I learned WordPress and SEO. It also turns out that I’m not all that interested in Columbus, Ohio so I couldn’t keep up the fake interest by writing about it on a regular basis.

That’s my resume up until the business I began in 2012. The same business I own and love today. Getting here has been a path filled with repeated failure, pain, and fear.

The fear of failure never went away. I just moved it to a different place—into the background instead of the foreground.

I diminished its importance. I was able to make failure less of a demon by accepting it as a normal feature of my journey. Scaring the wits out of myself often enough made me realize fear isn’t something that just disappears. I have also practiced a number of different techniques in courage. None of them is especially great so I’ll share just one.

Erica Reitman recently reminded me of a technique I’ve used for as long as I can remember. It’s called the “worst case scenario” method of putting fear in its place. This is where I write or voice all of the worst possible things that could happen as a result of my actions. Getting my fears out has this way of right-sizing them. Making them less powerful.
Then, I ask myself, “Can I live with the worst case scenario?” Sometimes, the answer is no. But, more often the answer is “Yes, I can live with the worst case scenario.”

Sometimes fear pushes its way back into the foreground in my life. And when it does, that’s when it seems like all of the good things happening in my life come to a halt.

Being afraid wasn’t something I could fix. So I stopped trying.

When I was able to stop fighting with it, then I could let it hang out in the background. I could get on with the meaningful and fulfilling work of making mistakes and learning from them.

Comment or ask a question below.

Welcome to WebDev Success. I’m Emily Journey and this podcast is where I take a hard look at the challenges facing the website development industry. Learn how to attract loyal customers, how to raise your prices with confidence, and take steps to craft the work life you’ve always wanted. Subscribe, listen in and develop brilliantly.

Join the discussion

  • I wouldn’t call your try at politics a failure. You were able to learn from that experience and obtain skills for the future. You changed a lot of people’s thinking about the world around them. It was fun too.

    • Roger! Yes, you are right. There were a lot of fun parts. We knocked on so many doors. Many of those doorstep moments and conversations are seared into my memory. And, I did gain important skills that I use to this day. I’m glad you were right there in the middle of the fray with me.

Further reading

Web developer working at table

Hi, I’m Emily Journey. I founded and lead a website consulting agency with six coworkers. This blog is where I write about the things I’ve learned at my real job.
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