Don’t be a Scaredy-Solopreneur: 4 Ways to Overcome Failure

Growing up in Michigan, Halloween was a BIG deal.  My sister, Jodi, and I spent months dreaming up our costumes, usually brought to life with full parental participation from fabric remnants, mom’s sewing machine and dad’s tool bench scraps. My favorite was the year we went as packages of plain and peanut M&Ms. You can guess which one of us was nutty!

When the magical night arrived, inevitably, we were faced with some degree of weather related snafu. The most common – frosty temperatures, but there were years of freezing rain and even SNOW.  What this meant is, if we wanted to go trick-or-treating we had to bundle up, completely destroying our long awaited costume debut.

As a solopreneur, I find myself with similar rush and falter feelings as I meet clients, have a wonderful conversation, get placed on hold for their event, and sometimes am NOT the one selected for the gig.  This is part of our business, and a natural process of the sales cycle.

Jodi and I did not let Mother Nature ruin our Halloween. Instead, we quickly strategized a redesign and got down to the serious task of filling our candy baskets.

Similarly, inclement moments in our business cannot dampen our entrepreneurial sprit.  We must find the sweet ways to weather the set-backs and move forward to the next inevitable success cycle.

Here are 4 lessons I learned that transformed those early yearly disappointments from scary to success

Look for a loophole
Ok, so we were required to wear our winter coats… but no one said we had to wear them outside our costumes!  We started to design our costumes to fit a full-on snowmobile suit underneath and could totally rock a tutu on top of layers of down!

So you are not the one chosen for a gig.  No one ever said that was the end of your relationship with that event and that client!  Think about “missed gigs” as part of your pipeline, and set up a special thing you do just for clients that choose another speaker.  For instance, two days before the scheduled event send a note to the planner congratulating them on a well planned event that you are SURE will be a huge success, and let them know you will be looking forward to the tweets and pictures of the happy attendees.  This often gets a sincere note of thanks for remembering them, and also lets them know you are connected and committed even when you were NOT the one chosen.

Be grateful
Jodi and I were sure to always say an extremely polite “thank you” to each homeowner and discovered it often led to an extra piece being plunked into our open sacks.

Even when things look stormy, find a way to feel gratitude.  In fact ESPECIALLY when things get rough… reach out to the people who have helped you along the way. Research has shown that expressing gratitude directly elevates your happiness level – and the study proved the more down-in-the-dumps you feel the greater the benefit of showing gratitude toward others.  No successful entrepreneur gets that way alone.  There is ALWAYS someone to thank for something.

Remember the goal
One year, as Raggedy Ann, I created the most perfect giant lolly-pop out of Styrofoam and colored paper… which completely disintegrated in the icy rain that year.  Quickly, I reminded myself that I was out on the streets to GET candy, not worry about my misshapen attempt at created candy.  Once I let go of wanting the prop to pop, I was able to focus on the important thing… finding the houses with FULL SIZE Milky Way and Reece’s Peanut Butter Cups!

When you set your sights on achieving something, allow yourself to take the long view.  Running a business is a learning process and no single style works for everyone. You will have moments where something you worked hard on falls apart. Sure, feel bummed for a moment, then toss is aside and look down the road to the next brightly lit door to knock on.

Celebrate the sweet success
After a night spiriting up and down the neighborhood streets, the most delicious part was coming home to sort the candy into piles.  For my sister it was like-kinds, chocolate with chocolate, hard candies with suckers.  For me it was more of a color exploration – wrappers of red in one group, yellow in another, until I had all the rainbow represented in six piles plus brown. Then to choose the three pieces that were allowed that evening and to just sit and see how long we could make them last.

If you spend every second of every day with you head down working toward the next goal of your business, you are sure to miss the delightful happy treats that happen along the way.  Perhaps someone reaches out to tell you what a positive impact you had on their life, or you receive payment from a happy client for a job well done, or you book a gig that is larger and more exciting than ever before.  Those are the delectable treasures that you must stop and celebrate, otherwise you will end up hunched over slogging from task to task forgetting to smile and say thank you.

And everyone knows that that the best candy always goes to the happiest trick or treat!


Tami is an energetic and thought-provoking communicator, speaker, and performer, with extensive background in both corporate and independent environments. She holds a Master of Fine Arts degree and Bachelors degrees in Broadcasting Communications, and Theatre. She has CTI coaching training, and firmly believes laughter is a vital part of learning and living. Learn more at


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