Confessions of an aspiring man

Hey Friend,

I’m struggling. Struggling to be all things. It’s a pressure I put on myself, but regardless of it’s source, it’s there.

I want to be and have it all. I want to have an adventurous, unconventional, exciting life full of travel and new experiences. But I also want to provide a stable, reliable foundation for my future family.

I still have years to do both, but I feel the pressure already. The pressure to prioritize stability and things like health insurance. I didn’t even get my own health insurance until 3 months ago, now I’m starting to think about it for a kid 5 years from now.

I know that I’ll figure it out. Even now, as I write this, I’m thinking of ways to feel I am financially preparing for the future while still taking strategic risks, such as ensuring I always save X amount every month for a “future fund.” I’ve had enough of these, “how am I going to do this?” moments to realize that I always manage to figure it out in the end.

But it’s going to be an adventure. Maybe life’s greatest adventure? Perhaps I could do for a personal redefining of the term.

I’ve always defined things like travel, adrenaline sports, and parties as more “adventurous” activities, but maybe raising a family while navigating career, relationships, and personal passions is the true adventure?

Man, I sound old.

All I know is I’m afraid of the tragic stereotype. The stereotype of the guy who had a dream but had to give it up for stability. And I’ve realized that it’s on me to make sure that doesn’t happen. That if something is important to me, I can’t put it off, because before I know it, it may be too late.

That’s the flip side of this pressure. While it’s possible to see it as a burden, it’s also possible to see it as an opportunity. It’s easy to feel like you have all the time in the world to make your dreams a reality when you’re young and single with no prospects of caring for anyone else anytime soon.

But when you have a deadline, a date by which it becomes less about you and more about the people you’re bringing into this world, it forces you to get your act together. To decide how important something is to you and, if it is truly important, to act on it. Now.

That’s where I am. What’s this important thing, you ask? I’m still discovering that, but I do know it’s aligned with all of the personal development and men’s work that I’ve been drawn to for over 6 years now.

What exactly that means, I’m not sure, but I do know that I want my career to feel aligned with creating a positive impact in the lives of individuals. In the truly meaningful facets of the human experience, such as relationships, health, and self-transcendence, to name a few.

Despite the majority of big things going well in my life, it’s easy for me to feel like it’s not enough. Like if I’m not excelling to the fullest extent, in every way, all of the time, it’s not enough.

Someone made an observation of me recently that is in-line with this. They said, “It seems like, because you have so much going right, you’re worried that any piece appearing to be imperfect will shatter the rest.”

True. Very true. Internally, it doesn’t feel like a show I’m putting on for others as much as for myself and my own inner critic. But it’s a show nonetheless.

Well, I hope that this letter makes it clear that my life is certainly not perfect. There is struggle. Good struggle. Purposeful struggle. But struggle nonetheless. And there are some moments where I feel everything is okay, and others where I panic at the insufficiency of EVERYTHING.

But hey, that’s life, right?

Selfishly, I’m hoping this letter acts as a documentation of my challenges so that I can look at it later and use the fact that I overcame them as personal fuel for future mountains.

Less selfishly, I hope that it does something for you. What that is, exactly, you’ll have to tell me!

I’ll catch you next week.

Take care,
Ryan