Fail Brilliantly

the power of failure.jpg

I really hate failing.

Throughout my childhood, I was the perfect student. I’m talking 4.0 GPA all day because anything less would make my stomach feel like it was rolling around on a ship during a storm.

If I was given a task that I didn’t understand I would get incredibly frustrated. Math especially was known to put the beginnings of tears in my eyes because it was a logic that just didn’t quite click with me.

I still remember chemistry in high school and how those damn formulas would look like abstract paintings. I would sit down with my mom (luckily a forensic chemist) for hours while she would help me figure them out. It wasn’t until I got to college that I started to learn how to embrace failure.

I was recently interviewed for The Powerful Mind Podcast.

isten to me talk about failing, travel, and forgiveness.

My first big paper got turned back to me with a C. C! I’d never gotten a C IN MY LIFE. I still feel stressed when I think about it. But that paper taught me a huge lesson: failing is good.

From that failure, I started to relax.

I was totally fine getting a B overall in my astronomy class because heck, that wasn’t what I was focusing on anyway and a B in something math and science-related seemed pretty darn good to me. I started taking more risks and pushed myself into situations that I wasn’t sure I would succeed in.

Now from all this so far you might be thinking “Wow, Anna is such a Type A personality.”


And no.

Sure, I like it when things work and are organized, but I only like it because it came from utter chaos. The art hanging in my office makes no sense when put next to each other. They clash, the styles are disparate, but yet that diversity keeps my brain moving in a myriad of ways.


From chaos comes creativity. From risks comes growth.

I traveled, worked, and studied abroad. Those experiences made me fully embrace the art of failure. I would wander streets without a map or a plan. Sometimes I would get horribly and utterly lost but I wasn’t afraid to ask for directions. I went in looking for an experience and the only control I put on it was where I was sleeping that night. I let go.

From that letting go I have memories and moments that never would have happened if I had planned my excursions down to the last minute. Sure, I went to all the important museums and allowed the full history nerd side of myself to flourish, but after the museums, I made sure I explored.

Failure can have unexpected and hilarious side effects

Failure can have unexpected and hilarious side effects

In my professional life, the trend of taking risks continued.

I said yes on a whim to be a Spanish startup’s social media manager even though I didn’t even know what Twitter was at the time and still owned a flip phone. All I knew was that I didn’t want to work in grocery store bakery for the rest of my life.

That ridiculous crazy decision to say yes to a job I had no skill or experience in brought me here to where I am today. I own my own business now!

Along the way, I messed up so many times. I made a million strange decisions that sometimes worked. I quit the job at the Spanish startup and worked at an agency, in a corporate office, and in a small wine distributors’ marketing office. I bounced around, learning, growing, and failing.

This is what we’re talking about today: failure.


Failure is an essential component of growth.

If you got everything right all the time, how would you learn? It took me a few times failing in the classroom to learn how to develop a better work ethic. It took me failing to find my path.

In the words of Will Smith, Fresh Prince:

“Failure is a massive part of being able to be successful. You have to get comfortable with failure. You have to actually seek failure. Failure is where all of the lessons are...Successful people fail a lot but they extract the lesson from that failure...practice is controlled failure.”

If failure is so important to growing, why are we so afraid of it?
We are taught from a young age that failure is a very bad thing.

  • Kids in little league softball are benched because they aren’t quite as good as others players...but then how will they develop their skills?
  • The educational system is highly focused on testing to determine a student’s ability and punish the kids who don’t do well...but what about the kids that aren’t good at testing?
  • Making a total hot mess in the kitchen while attempting to bake your very first pie is frowned upon by your mom...who follows you around with a washcloth...but then you wouldn’t be able to make an awesome pie now.
  • Trying to jump out of a tall tree to see if you can fly as a kid might be seen as idiotic to us adults, but we all tried a similar experiment when we were young.
Well, at least you tried.

Well, at least you tried.

Being afraid of failure makes us walk through life like we’re on a tightrope, hoping we don’t fall. It makes us complacent in those jobs that make us feel like total zombies. It makes us ok with having a job that we hate just for the fact alone that it pays our bills.

But you know, what would happen if you tried something different?

In the business world, and especially as a solopreneur, failure is, and probably should be, terrifying. Your livelihood is tied up in the success of a particular venture. You have bills to pay, your life to support, your home, your relationships, your pets, your kids.

But no product was ever perfect the first time.

And no product is perfect the second, third, or 1 millionth time. I still get annoyed with my shoes and shoes have been around for who knows how long. People are still making innovations with shoes.

If you want to listen to me talk about failure more, I was interviewed for The Powerful Mind Podcast. Listen here.


how does someone who is afraid of failure navigate the scary waters of solopreneurship?

When I decided to make the great leap and quit my cushy full-time job, I made myself a promise.

I promised that each time I turned my computer on for work I would fall flat on my face. I quit my full-time job to fail, to go mess up.

Sure, I had 3 years of experience in my field at this point, but I didn’t know anything about running my own business. The proposal process, contracts, invoicing, budgeting, processes, services- all of that was a great wide unknown to me. I did a TON of research, but research doesn’t equal practice.

As a full-time freelancer just starting out, I needed to figure how this whole thing worked. No matter how much research I did doesn’t mean that someone else’s system is going to work for me.

Having the mindset of going out to fail brilliantly made me take the risks I needed to take in order to grow. If I was so stuck on being perfect all the time there is no way I’d be where I am today.

In the first two months, I said yes to almost everything. Some projects I had an inkling that it wasn’t really a good fit for me, but the goal wasn’t to find perfect projects or clients.

The goal was to learn what those perfect projects and clients look like.

The goal was to learn management, the intricacies of project management, and to honestly have a few really bad experiences.

From those mess ups and bad experiences I now feel empowered to say ‘no’ to other projects that come my way that is more than just a gut feeling. I know who I want to work with and I’m getting better at hearing red flags from a potential client in the discovery call.

Three months into this entrepreneurial venture I said no to what could have been a major opportunity. I’m talking mad dollar signs in your eyes with a company whose logo would be AMAZING to have on my website.

But, in the discovery call, red flags were going up all over the place. They said the scope would probably change 3 times. They pushed back on my process, which is now tried and true.

It was clear they didn’t value me as a business partner. I agonized over it a few days, because damn it’d be nice to have that big of a project.

I kept putting the project on my calendar to see how it would line up, and all I felt was stress.

That project felt like a closing of a door, not an opening.

In the end, I told them no.

If I had said yes to that project, guaranteed I wouldn’t have time to write this messy blog post right now, and I wouldn’t have been able to say yes to two new clients that I totally love.

Not everyone can do those cool tricks. Know your strengths.

Not everyone can do those cool tricks. Know your strengths.

Processing failure

Now, I’m not saying go out and fail purposefully. I’m saying put yourself in situations you’re a bit uncomfortable with and that you’re not sure how they are going to turn out. When you do fail, this next bit is the most important step.

Be intentional about understanding and feeling that failure.

However you process your feelings, whether it be journaling, talking to yourself while cooking dinner, going on a run- do it with intention. If you talk to yourself, record it. Make it intentional. Talk about that failure and why it was a failure.

Turn that failure into a lesson.

Without the intentional processing of the failure, it’s just a mess up.

It will always be something that you look back on and go “Well shit that sucked.” Put that failure into your processes at work or in your checklist so it doesn’t happen it. Let that failure build you up rather than tear you down.

I’ve messed up so many times since I started my company. But hey, I’m doing pretty alright now. From that perfect A+ student who cried a little bit any time she got a math problem wrong to who I am now, I've grown so much. I love who I am now. I love that I thrive in the chaos of failure.

Be ok with taking risks most especially when you’re just starting out on your solopreneur project.

That is the time to do it.

You have to take risks and be ok with potentially falling on your face in order to grow your business to the level you dream of.

Go out and fail brilliantly.