You gotta bet on yourself, kid.

How to navigate the balance of confidence and humility.

My newsletter has grown to over 400 subscribers. I’m incredibly humbled and excited to see this growth, so I decided to begin a Patreon where people can support my writing by making a monthly donation/tip. This newsletter is about my growth as a writer, my dedication to writing, how I’ve learned to deal with insecurity, and why we have to learn to bet on ourselves. I hope you gain something from this essay (well, all my essays!) and consider supporting me in this endeavor. I hope I can support others, too. Thanks in advance, and thanks so much for reading as always.

Shortly after my Nanna died in late 2016, I found out she had been printing my essays so she could read and save them in a binder. I wasn’t writing much, just posting the occasional essay online which would be sent to her via email by my Aunt Sherri. I didn’t even think I could be a writer at the time. The essays I had been writing were saccharine; I was trying to make sense of the world in the aftermath of heartbreak. Those writings were certainly not that profound. They more resembled journal entries, padded with optimistic language about how I was going to appreciate even the small joys of life (to be fair, I still write about this stuff today…). I wouldn’t have called myself a writer. If they hadn’t been published on a blogging website, they would’ve been fine as Facebook statuses. 

My Nanna was the first person outside Lyss and my parents to bet on me. She called me a writer and loved my writing. She would tell me all the time that she believed that I’d be involved in finding a cure to CF one day. We would talk politics and social issues, we’d chat about her life growing up, we’d argue and tease and make fun of each other. My sweet, sassy, witty Nanna believed in me long before I ever believed in myself.

It has taken me a long time to get where I’m at today. Anybody who knows me I’ve always been an opinionated person. I can remember when I was a kid, my parents taught me to never begin a fight…but also to never back down from somebody trying to bully me. I don’t remember if they taught me that just because they thought they should, or if they were preparing me for a cold world, full well knowing cystic fibrosis would pose more problems for me than other boys. I took their lesson in stride. My parents taught me to be strong even when I felt like being weak. It also probably doesn’t help that both my parents are pretty stubborn, but in a way that complements one another.

And for all my opinions, my insecurities are two-fold. When I’m convinced of something, it’s rarely rooted in mere opinion or emotion. I like to research and question and think through my beliefs, then I like to think about how those beliefs can be challenged. Today, my opinions are about social issues and politics, but the skill-set is one founded in my love for the Steelers. Growing up in Cincinnati, I would constantly argue with other kids about sports. My dad, a Steelers fan who watched the seventies Super Bowls in the sweltering steel mill, raised me on Pittsburgh football but also told me not to engage in these arguments. I took immense pride in my love for a team that won so much. I had a hard time understanding why so many kids loved teasing me about liking them, but it taught me how to comprehend my beliefs. I’d research the Steelers, their depth chart, statistics, their opponents, and the previews every week so I could better defend them. When I’d get caught flat-footed in an argument, I’d feel a chill come over my body. The humiliation would always be palpable. Nothing irritated me more than being wrong. 

Over the years, I’ve had to work on that skill. Today I recognize admitting when you’re wrong, taking responsibility when you mess up, and showing vulnerability are some of the most critical skills to being a good leader and building a team. I’ve also had to learn how to remain confident and opinionated while also staying humble. This can be a tightrope: Confidence without humility can become reckless arrogance; humility without confidence can lead to feckless indecision. 

Striking a balance of confidence and humility is one of the most important tasks we can do for ourselves. Our conception of ourselves is like a block of marble. It begins as an unidentifiable cube, but we chip away at it until it begins to take shape. At first, we try strategies that we have no idea if they’ll work. We may try faking it till we make it or we may try to stop voicing our opinions just to see what feels right. As we grow older, we become more nimble and precise with the chisel — our strategies — until we have a more complete idea of who we are. We chisel away the insecurities, both externally and internally, until we become less and less affected by others’ conceptions of ourselves, until all that matters is our conception of ourselves. Nobody else’s conception of us matter than our own conception of ourselves; we are merely ideas to everybody else. To ourselves, we are our universe. We have to be. If our conception of ourselves is a perception of a block of marble in our head, we are also blocks of marble in other peoples’ heads; the important part is that these blocks will never be identical. They can’t be identical. We are with ourselves all the time; everybody else is only with us a fraction of our lives. Why should their chisel have more say than yours in your block of marble?

It’s important we thoroughly develop our conception of ourselves to combat insecurity. I’ve found this strategy is what works to balance confidence with humility. When we have a good idea of who we are, mistakes and disappointments don’t infringe upon our self-conception nearly as much. When our self-conception is dictated by others and poorly defined, disappointments can limit, hurt, and set us down a different path. But when it’s better defined, disappointments are an opportunity to grow and learn, while not limiting us and making us feel inferior.

When I look back at both versions of Young Tré — the one so terrified to call himself a writer and the one who always felt defensive about meaningless football — I feel sad. Hindsight is 20/20 clear of course, but both versions of Young Tré are heavily struggling with insecurity. Throughout my entire life, I’ve always been terrified of others judging me. I’ve worried others had their finger on the pulse of what a good person is or how we should live life and that if I didn’t live up to those expectations that others would think less of me. But none of us really have an idea of the best way to live life, so why not do right by yourself? 

It’s a waste of time worrying what others think about you and your decisions. We should try to do right by others — treat them with respect, be kind and compassionate, apologize when you’ve harmed them — but we also have to do right by ourselves. We have to be able to bet on ourselves.

So in an effort to live what I’m preaching, I’m taking a leap of faith and betting on myself. I’ve decided to make the decision to try to make a bit of money from my writing. I’ve created a Patreon for my writing: Patreon.com/TreLaRosa Patreon is a platform that allows creators to cut out the middleman for compensation of their work, thus allowing supporters to directly compensate creators. I don’t want there to be a barrier between my readers and my writing, so my writing — this newsletter and trelarosa.com — will remain free. 

My plan is to continue to write this newsletter once a week. Sometimes, it may be twice a week. All I’m asking is that if you’ve enjoyed my writing, learned from it, felt like it resonated, or whatever else, you consider contributing a monthly $3 donation. You can also choose to contribute $3 then immediately cancel your recurring donation if you so choose. For a long time, I thought my readers were solely doing me a favor by reading my writing. Then I considered how I would respond if one of my friends or family members were creating some type of art that requires talent for free. I’d encourage them to find a compensation model that works for them. I’m not trying to make thousands of dollars through my writing. I consider this more of a tip to say you appreciate what I’m doing and the work I’m putting into this. We’ve nearly tripled subscribers since November to over 400. Insane. Each newsletter takes anywhere from one to four or more hours to plan, write, research, and edit.

I would encourage each and every one of you to grind and put work into your craft. If you appreciate the work I’m doing, I really hope you consider supporting me. Once we get to $20/month, I’ll consider upping this newsletter to two times a week if people think that’s a good idea. As the Patreon grows, I hope to put more work into my creative endeavors: Other types of writing, YouTube videos, skits, a podcast maybe, and other ways of building a community.

Thanks to all of my readers. Whether you decide to tip or not, I understand and deeply appreciate you either way. 

I’m betting on myself. I hope you’ll bet on yourself, too.

If you can’t make a financial contribution, I totally understand! Commenting or replying to the email with your thoughts or feedback or sharing my pieces is the best free way to support me. Any type of support sincerely means a lot to me.

tl