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Sometimes we must experience failure to realize we were meant for something even greater - Stephanie Be | TravelBreak QuoteWith a glass of Chardonnay, I sat across from a college friend at the local university bar. It was the nicer bar… we’re grown ups now. I hadn’t seen him much since he’d been recruited into the MLB, only to be spit back out like most college and professional athletes.

I: the creative, traveling entrepreneur. He: the professional athlete.

We are the American Dream.

“It’s just really cool that at least you went after it. You tried.”

He vocalized his thoughts on my business pursuit… but I wondered if it was a message he’d often repeated to himself too.

For a moment, we understood each other much better than we ever had. It’s that feeling you can only understand when you really really really really wanted something and were so close, but didn’t get it. Or worse, you got it and it was taken from you.

It’s that same moment I experienced when I later hopped on the phone with a fellow, older UCLA “sorority girl” who worked for every major entertainment brand only to fail the GMAT before applying to the UCLA Anderson School of Business. She passed it round two. She eventually got in. It’s easy to write, but I bet it sure as hell wasn’t easy to experience.

Trading med school for pharmacology sales? Swapping architecture to be insta-famous?

Changing careers? Overcoming failure and uncertainty? It’s a conversation I’m becoming very familiar with.

Individuals dedicate their entire lives on making their dreams into goals. Who are these individuals? The person in tech, the athlete, the actress, the model, the musician, the photographer, the comedian, the writer, the director — every person who has pursued and perspired for a less-than traditional career in talent, as a free-lancer or to start their own business. Every person that went after the white-picket fence, only to fail their LSAT goals; alternatively, the ones finally getting what they wanted, only to realize it’s short-lived.

I know how you feel.

Overcoming failure is a feeling one just doesn’t forget.

So what happens when you dedicate years of your life or — your whole life — to something and then it doesn’t work out? When you’ve only known basketball for twenty-five years? What happens when you spend four years in college learning engineering and still can’t get a job ten months after graduation? What happens when you pump $15,000 into a business and you lose it all?

What happens when being “the best” becomes “not good enough?”Click To Tweet

Failure can destroy you. I know because I have failed, and then I pivot. Actually, I failed twice and succeeded in my third attempt to start a business.

I started going to tech conventions when I was nineteen. I always wanted to start my own business and there was something so sexy about virtual reality. Technology is smart, practical — and location independent (I love to travel and that’s what I do now for a living). Technology is about creating and selling something more than the things we make with our hands. It’s brilliant and I love it.

So I went after it. I tried to develop an app. I worked until four am, six days a week and half days on Saturdays, doing research and development. I swallowed my pride and moved in with my parents without a car or single shopping spree on the horizon. I learned how to pitch investors and partners. I learned how to generate press, how to create an online community. I even learned how to code. I taught myself everything through the internet.

I invested time, energy and money and it didn’t work out the way I’d envisioned. I don’t have some super cool app to show for working myself into the ground — to the point where my parents sat me down to tell me that they were concerned for me.

I was not in a great place. I didn’t want to give up, but eventually, I moved forward.

I’m pretty convinced that failure is worse than heart-break. It’s like breaking your own heart and then hating yourself for doing it.

Eventually, I let go of my failure, and instead focused my new skills on a less “esteemed” pursuit. A blog. Yes, I literally started a travel blog and started to travel the world again. Travel makes me happy. No more tech conventions. I didn’t want to go to law school and quite frankly, I didn’t know if there was anything left to learn from a business degree. At this point, I had nothing left to lose and all of my skills pointed to digital media. So again, I worked too much for too little. This time it worked!

At twenty-four and half years old, I started my third business. At twenty-six, I finally feel comfortable saying that “I’ve made it.” I don’t know what “it” is, other than that I forgave myself for failure and comfortably monetize on a career I am passionate about. I am the proud owner and founder of a popular blog. It’s a very small-business, but it works.

So how do we move past failure?


Celebrate the skills you’ve learned and channel them into something different.Click To Tweet

Did sports teach you discipline and to be a part of a team? Did photography give you a unique understanding of colors and patterns? Coaching is a lot like consulting. Photographers have much in common with web designers.

Feel my vibe?

Just because you want to switch careers doesn’t mean that your new path won’t benefit from the wealth of knowledge and experience you’ve acquired.Click To Tweet

Focus on what you got out of all of those years, not what you lost.

2. Let go of “what if…” — It could have been something you wouldn’t have loved anyways.

So what if we had made it to be the next Beyonce, Zuckerberg, or Bryant? We could have been hit by a car the first year. We could have been perfectly happy or dreadfully unhappy. The problem with pursuing our dreams is just that — dreams aren’t confirmed to be a reality. We have an idea of what it’s like to be singing around the world, playing ball and selling the next Snapchat Inc.

The press, media, and our own minds create this idea of success, but these ideas of “success” when translated into a reality don’t actually equate to happiness.

When my app wasn’t working out, I realized that I didn’t want to develop a career for myself where I had to work until 4 am every day anyways — but that’s what many CEOs do: work a lot. I can also tell you, that as a blogger and social media “personality,” I’m one of the few that really monetizes on my lifestyle — a lot of those “instafamous” people you’re aspiring to be don’t have an income or much agency.

Things aren’t always what you perceive, so maybe it was for the best that you didn’t achieve this misconception.

3. Love the people that still love you, they’re the ones who always will.

It’s easier to make friends when you’re in the spotlight. But failure affects our esteem, our time — even our finances. You can really tell who loves you when they’re still around after all those trips to Vegas you had to turn down to focus on your career or when that million dollar contract didn’t work out. It’s the friends and family that love us when it’s most inconvenient that make it easier to forgive ourselves. They love us, so we can love ourselves too :)

4. Embrace the alternatives. Switching careers isn’t failing, it’s pivoting.

For me, failure in one space proved for a happy, successful career in another space. Had I not tested my passion for websites and connecting people, I would have never thought to pursue a career in blogging.

Failure taught me that I thought I knew what I wanted, but I had no idea what I actually wanted.Click To Tweet

Failing? You'll be fine. There aren’t enough conversations about all of the successful people who pivot. Bill Gates: started no-name Traf-O-Data before he started Microsoft. Vera Wang failed at making the U.S. Figure Skating Olympic Team before joining Vogue and starting her own fashion line. Morgan Freeman? He didn’t get his first breakout role until he was 52!

5. Know that you are “enough” without whatever you are trying to achieve.

There are so many complex factors that play into achieving our goals. Just because you didn’t make it to the big screen doesn’t mean that you aren’t pretty or funny. Just because you didn’t get past college football, doesn’t mean you aren’t an admirable athlete. Just because I couldn’t run a successful tech company at twenty-three doesn’t mean that I’m not equipped to be a leader in business.

We are defined by who we choose to be, not just what we do. Failing doesn’t make you a failure.Click To Tweet

It just means you were strong enough to try. And that strength? It’s a lot like fear — it’s something you don’t forget. Run with it.



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