Blog: A Career Built On Failure

Crowdfunding promo SQIn the lead up to the Be Awesome Festival pilot on the 23rd of May 2015, we’ve invited US-based entrepreneur and social innovator Allie Armitage to share her powerful first-hand experiences with failure. Allie has been a critical friend and mentor during the creation of the Be Awesome Festival pilot.

Be Awesome is made up of a team of passionate volunteers. If you share our vision, please support our crowdfunding campaign for the Be Awesome Festival; a transformational event empowering the next generation. Visit the campaign here.


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I have to confess, I’ve built my entire career on the back of a failure.

I started a company right out of college, which I worked on for 5 years called weBike and felt deeply passionate for. I learned so very much in this experience and for so long I believed this idea had to work because we were taking such a big risk and we were giving the work our ‘all.’

And after five years of pouring our souls into weBike, we realized that we couldn’t get the business itself going fast enough to support our own livings (there were four of us). We came to a very hard conclusion that we needed to fold the company.

There were a lot of difficult and seemingly impossible tasks that I had to take on in this process, the hardest of which was giving back our crowdfunding money. We had recently raised some funds for a project in a last ditch effort to jumpstart our sales; and now that we were folding, I had to share with all my family, friends and supporters that we would be giving their money back because we were closing the company. It was the most public admission of failure I had ever experienced in my life.

After experiencing intense anxiety writing the message, and thinking of how disappointing it would be to share this with everyone who had believed in me, I was surprised to see that pressing send on the email actually felt like a huge weight off my shoulders. And then even more incredibly, how loving and encouraging everyone was in their response – “we’re so proud that you tried,” “you guys worked really hard and you should feel great about it,” and “we’re here for you!”

That was not what I was expecting in any way, shape or form. I had been bracing myself for utter disappointment and shame.

What I realized was that the intense fear of failing is at its fiercest when we hold it inside ourselves. After we let it out, it actually has very little power over us. Like Brene Brown says, shame cannot survive being shared. It only has it’s power when we keep it a secret.

In the year or so after the event, I started to share my experience more openly with others. I often fumbled for words, and felt a trail of shame as I spoke them …but I continued to practice saying out loud that “we folded weBike”; that I had tried a startup and it failed. With time, I started to own up to the reality of the situation with more depth and clarity – I saw the insights and lessons glimmer crisply as I gathered distance, time, and emotional space from all of it.

As I re-discovered myself and started making moves to pick up and find a new path, I continued to find the ways that weBike was a fundamental building block to where I’d go next. In fact, it was going to be the entire foundation of how I built the next phase of my career. The amazing, community of entrepreneurs whom I had gotten to know in DC became a web of ideas, hope and inspiration to me; and the essential truths I picked out of my five years at weBike proved to be the first pieces to my puzzle in moving forward.

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My story continued like this – I found my next role through my new community, and then I was offered an opportunity to teach part-time at the University of Maryland by a mentor of mine. In all of those experiences, I uncovered my passion for empowering others to understand and pursue their own motivation and drive, and now I do that work as my full time job.

What I find most ironic in making a living with work that I love, is that the most significant thing I’ve had on my resume up to this point is a failed startup.

But it just doesn’t seem matter to anyone. I keep waiting for someone to call me out and say, “all you’ve done is create a company that never made it .. what do you think you’re doing?” No one does.

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What does seem to make a difference is that I’ve decided to embrace failure as part of my background and I now share it and use those lessons all the time.

So here is what I gleaned in the process that I offer up to you in case it’s helpful:

  1. As cliche as it sounds, there is really a reason we say “A for Effort.” The process of opening yourself up to pursuing ambitious goals is exactly how you grow and learn, irrespective of the outcome. I have been able to recreate my career upon the goldmine of learnings that I gained in the process.
  2. When you share something hairy and frightening like the experience of failure, it doesn’t feel shameful. As counterintuitive as it may be, sharing these things openly often creates more connection between you and whomever you’re talking to … and it may even inspire them.
  3. The experience of letting go, and of actually failing can be quite liberating. As a raging perfectionist, I was more scared of failure than of anything else in life. Yet “doing” failure – conquering my biggest fear – was far less terrifying than I thought it would be. Allowing its release over me felt freeing. I now know I won’t die in the experience failure, and that I might actually come out much stronger from it all.

Follow me, or check out my blog. Let me know how I can help you find and pursue the things that are worth risking and learning from failure 🙂


Be AwesomeAbout Allie Armitage

Allie Armitage empowers people to see themselves clearly so they can create a life that motivates them. She is founder of Mind Into Matter and an adjunct Professor at the University of Maryland’s Academy for Innovation & Entrepreneurship. Through her work she leads interactive workshops and coaches clients one-on-one to apply entrepreneurial attitudes and self discovery tools to build a meaningful, aligned life.

In 2007 Allie co-founded a station-less bike sharing company, weBike, where she gained her appetite for entrepreneurship and learned how to use the tools of design in a tangible business. Afterward worked at the Entrepreneur’s Organization and Netcito to gain deeper insight into the inner leadership journey for entrepreneurs. Now she teaches, coaches, and facilitates to inspire others to create their own path, and enjoy the journey.

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