Daring Greatly

How sometimes when you lose, you win.

Alejandro Estrella
7 min readMar 12, 2018
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“Believe that you can, and you’re half way there” — Theodore Roosevelt

What many people don’t know about this monumental figure is that he was not always so. Not only was he a sickly boy with debilitating asthma but also suffered bouts of depression; probably due to the limits his frail body put on his insatiably active mind.

But his father always insisted on one thing; move.

As Americans, we first learn about Theodore Roosevelt in fourth year of primary school and then you never forget him. The man is simply uncontainable. For all his flaws, he remained in my mind, the ultimate embodiment of American values, not least of which was adventure.

But this is a piece is about one of my most recent adventures and I share it in the hopes that it will inspire you to go on your own.

Three weeks ago, I made the conscious decision to stop expecting my life to go smoothly. I don’t mean I’m giving up on pursuing my goals; quite the opposite, I’m doubling down.

Back in October, I moved to Germany with a very clear goal: to continue my education.

Though significantly more student friendly than in the U.S., I would be lying if I said I wasn’t met with some challenges along the way.

In short, as a foreigner, you need to prove a legitimate purpose for your stay. This is perfectly reasonable and I figured I’d find a job, make my intentions to study later clear, and eventually be able to balance the two. This is not altogether ridiculous here as Leipzig is primarily a student city and many have moved here specifically for this reason.

After weeks of hustling like a true New Yorker, I managed to find a sales position at a respected local company and was offered an opportunity on their team. Though I wasn’t exactly sure what their sales process would look like, I was excited at the prospect of learning about online marketplaces and building off my existing sales experience. For the first days, it really seemed that I had landed safely. Not only was the team friendly and supportive but there were several other employees pursuing studies while working. A new sense of possibility came over me and I worked hard to try and quickly adapt myself to the company’s way of running things.

Confident in the security of a new job, I signed a lease, moved from my friend’s where I was graciously being hosted, and began creating an environment of optimal productivity but characteristic comfort.

Then the storm blew in.

Though I won’t belabor you with the details, 6 weeks into this new job, my managing directors and myself mutually agreed that it would be best for us to end the relationship.

This experience was one which followed with several life lessons. For year’s not, I’ve known of these in theory but now I was living them.

Lesson №1: Ask and listen closely

Though at the 6 week meeting with my managers, the pain points of our relationship were made clear, I couldn’t help but feel that something was being held back. Perhaps there was something left unsaid regarding expectations or other but rattling my brain over it won’t fix it now. However, being true to my pensive nature and wanting to try an figure out what went wrong to learn from the experience, I did what I know best, I asked.

Maintaining and nourishing my interpersonal networks has always been important to me which is why I’m still on very good terms with past employers and colleagues. So to try and get some answers, I got on the phone with some of them to explain the situation and ask where they thought I may have come up short. I explained to them that I felt a bit blind sided. They were more than willing to listen and help.

This is of course (for both parties) easier said than done. You need to put your ego in your pocket, have pen and paper ready, and listen intently. But if your relationship is true, they will share their observations with you and you will have acquired something invaluable; your behavior from an outside perspective.

Lesson №2: Never Burn Bridges

Though having this job opportunity fall through places me in a less than desirable situation, I made sure to openly receive criticism, take full responsibility for any shortcomings (said or done), and clearly express gratitude.

At this point, most people would be freaking out. With only one month’s rent left and a dwindling savings account, most people would be outraged much less have the patience to sit there and smile as the rug gets pulled out from under you!

So how did I do it? Three words, The Long Game.

For better or worse, working at this company provided me with something valuable that I didn’t have before; a reference from a respected German company. Now that may not seem like much but in a city of only half a million, that says a bit and here, that little bit helps.

So try to never burn your bridges and as a dear friend and mentor once said, “always leave the place better than you found it.” When writing I’ve noticed that I rarely come across constant beliefs or perspectives I’ve had in life but playing the long game, has been one of those few constants. My family has always made me the butt of jokes saying I think too much, and maybe they are right in some respects. It’s well known now that too much rumination can be stunting. But in this particular case, keeping in mind my end goal to stay here and placing the value on keeping alliances in the face of uncertainty; my long term perspective came to my aid.

When in doubt, “to thine own self be true.”

Lesson №3: Be open minded, not open ended

Ok. But now what?!

I’m in a foreign country, back on the job market with a time stamp on my head of about 60–90 before I’m politely asked to leave (because Germany will seriously deport my ass).

So I get back to my apartment after my final day at work and it takes a few hours before the panic kicks in. Only this time, things appear to be different. For reasons I am still discovering every day, I experience what I can only describe as a cognitive jolt of resistance to the panic. It would appear that lying somewhere in my deep-mind is the assurance that somehow everything will be alright. I’ve always been prone to an uneasy stomach and bouts of anxiety, but it’s as if I’ve somehow been inoculated to this most recent blow to my emotional and financial stability.

But how? Why? Naturally, as a student of behavior I was intrigued and wanted to know. Science all too often presents case studies of things when they go wrong and like to point out why. But in this case things went right. After some weeks of inquiry, I arrived at several factors but one resounded above all the rest; Gratitude.

When I first arrived to Germany, I was truly moved by the help I received from my small but close tribe of friends that I’d kept in touch with over the years. From letting me stay in their guest rooms to helping me find used furniture for my apartment and sharing their meals with me; I was truly humbled by their kindness.

It was then that I realized that this gratitude had somehow worked as an internal mechanism for fending off whatever negative thoughts and limiting beliefs that would normally resurface under such circumstances. Seeing my friends come together to aid me, validated not only their love but my self worth at a very critical point. To have this is to be truly rich.

Here I learned that it is alright to have plans but to more important is the flexibility to adapt those plans to achieve your end goal. As I write this, I am conducting a skills audit and exploring every employment opportunity where I can bring value, no longer hindered by the shackles of self defeatism. This is a very clear lesson from life. Your business is to choose your end point, not to know how you’re going to get there. Choose your goal and move toward it. To stubbornly plan is to invite inevitable and debilitating frustration. Set your eyes and move.

Lesson №4: Get back in the ring

Coming to this final lesson was surprisingly satisfying. I couldn’t help but smile and laugh out load to myself. It’s been a while since I’ve been in the arena but like good old Teddy Roosevelt, calling to mind my own martial arts background brought back this excellent excerpt which I will let speak for itself and close my entry far better than I could. What is life if not a series of battles? Some are fought within and others without. You can prepare for them, yes, but the outcome is ultimately left to the fates who often favor the unyielding heart.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

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