The Point Is to Keep Trying (Substack Writings)

Ready?

One of my first excitements early on as I was growing up was learning how to drive! I was normally the kid my parents never had to worry about, but as an enthusiastic (and naturally reckless) beginner, I was a terror. The screams from my unfortunate first passenger (aka Mom), I still remember to this day. I don’t blame her! I would accidentally cross over lanes without warning, randomly (and too aggressively stop), forget turn signals, stop signs, drive way too fast, etc. Good times.

Eventually I got the hang of driving and loved it! I loved it so much that even while I only had my permit, every opportunity I got, I would be driving our family car all over Puerto Rico. After school, I would volunteer to drive my younger siblings to the library or to their after-school activities. After my parent’s finished work, I would drive the whole family home. And wherever we needed to go I was driving, getting that practice in. Many of my school friends were already bragging about their licenses and I was ready for mine. So when it was time — I was ready.

Test day arrives and I’m nervous but confident. I sit with the examiner and drive cautiously but self-assuredly. Proper turn signals — check. Changing lanes slowly, mirror checks included — check. Within the speed limit — check. Parallel parking — beautifully done! So far so good. Then driving back to the start point, I make a right turn around a big, white van, back to where we started and park the car, awaiting my results.

Confident with my performance and giddy with excitement, I look expectantly at the examiner for his assessment. And he says nothing, just quietly hands me my test document with a red “Desaprobada”. In english: “Failed”. My heart instantly drops. I’m confused and ask, did I just fail this test? And he tells me yes, I didn’t make a complete stop at the stop sign, by the big white van. What stop sign I think to myself? I didn’t see it….

Crushed, I walk slowly to the waiting room, where my Mom takes one look at me and immediately goes from excitement to sadness as I tell her the bad news. Then I cry on her shoulder for a little bit. I felt so sure I was ready and here I was, a failure.

To sixteen year old me, of course, this ‘failure’ felt understandably big and burdensome. That license represented adventure, independence, freedom, and adulthood to me. And I had prepared for it, felt ready and excited for it, and then couldn’t quite get there. While the rest of my peers, everyone around me, had already crossed that line — driving to school, picking each other up and moving forward, I had to go back and try again. Quietly try again.

It sounds small now, but it was the first time that I had failed at something I thought I was so ready for. And it was also the first time that I had to decide for myself, what this meant for me while the world kept moving forward.

Try, Fail, Try again

I would eventually take the driver’s test two more times. The second time, I failed again. This time because the parallel parking spot was on a hilly, busy street, and I unfortunately took too many turns to get my car parked. Never mind I was on a difficult incline and had a line of traffic behind me! And then the third time, I was expecting a battle again, but it was …. extraordinarily easy. I took the test in a new location, away from hills and heavy traffic and was able to pass with zero issues. That was also the best parallel parking job I’ve ever done — even for today’s standards!

And yet this would not be the last time that I’d have to try, fail and try again. In my career and in life, I found myself in many instances of “failure” that would require me to start again every single time. In my military career alone, I failed at critical moments, especially in training events that I couldn’t actually afford to fail. Each time, I had to buckle up. Face my embarrassment and shame and try again anyway.

New Skills Unlocked

And while I was devastated each time the outcome wasn’t what I wanted, in the midst of the challenge, I was gaining something far more precious. Because while my peers were moving forward, I was going back, building skills they didn’t need yet, ones I still carry with me to today that help me through moments not everyone has the foundation for:

Resoluteness — Stick-to-itiveness. I grew a kind of unshakeable commitment to seeing things through, whatever the outcome. I found myself not brought down by past failures but buoyed by the possibility of success, as long as I kept trying. That commitment was tested early in my career when I found myself alone, at night, in a vast forest, one of the few retaking a test while the rest of my peer group slept. If I could find the spark even then, I could find it anywhere. And I did, on far darker nights than that one.

Changing the Conditions. I learned that sometimes you have to change the conditions if you want to succeed. I had been trying to pass a test on a hill, in heavy traffic, with cars lined up behind me. How does that help? Instead, I changed the circumstances and chose a new location. We don’t have to keep attacking the same problem, the same way. Sometimes changing the conditions is the smarter path to where we want to go.

Deep Focus — Ignoring the Noise. I found my ability to deeply focus and ignore the noise increased. I wasn’t as swayed by what others were doing or where they were. I was only focused on trying to get to where I wanted to go to the best of my ability.

Finding the Humor (and Humanity). I found that I was able to loosen up. I stopped taking “failure” or “mistakes” personally and started to see them as stepping stones to a greater version of myself. Humor helped me lighten the mood and see the humanity in the circumstance. Like the fact that I was trying to parallel park a car on an impossible incline with a massive line of traffic behind me!

Comfortable in the Uncomfortable. I learned quickly that if I wanted to push ahead in the challenging times, I needed to get comfortable moving forward even when things felt hard and I didn’t feel my best. Tired, doubtful, embarrassed, ashamed, confused, sad: I could feel all of it and still move toward my goal anyway. I discovered I could shift, adjust, and pivot in whatever uncomfortable circumstance I found myself in and keep going. And I learned to show myself grace and compassion along the way. I was doing my best, and it was ok if my best in that moment, didn’t meet the intention or the mark. I could always try again.

You Can Always Try Again — It’s Your Timeline

And ultimately, that’s what I always take with me: I can always try again. And that’s a surprisingly freeing feeling. I’m not locked into the circumstances because I can try again, change the story, try something new or learn something new about myself.

And that’s something important I recognized, as I experienced failures and mistakes. I found myself each time, becoming even more acquainted with myself. I learned I can handle difficult moments. I learned I can re-inspire myself even when I was alone, with no support nearby. I learned to see myself compassionately and even the circumstance with humor. We are human after all and life is one series of interesting challenges isn’t it.

So today, even when I fall off my own alignment, or I find myself lost, uninspired, or losing focus and momentum, I always know I can try again tomorrow. And the next day. And the day after that. Even if it’s hard, even if it’s easy. And I can change the conditions if I need to and always begin again.

Because sometimes it truly is the challenging stuff, the stuff that stretches us, that embarrasses us, that touches our wounds, that helps us expand ourselves in ways comfort never can. And that’s not something we need to fear or a timeline we need to judge. If we’re asked to give it a shot, again, more than once, that’s ok. Everyone is on their own timeline of becoming who they’re meant to be.

So rather than run from challenge or from supposed mistakes or failures, embrace the growth, opportunity and even potential they offer. And see what they bring out in you. And how you can help others keep going too.

True we don’t always get to choose what we’re given. But we do absolutely get to choose what it means, and how we use it.

To us. Doing the best we can. ~ C🤍