I get why we fear dreaming. It’s hard for us to get our hopes up that things will go the way we want them to. Yet and still, we need to put this worry as far away from our psyches as possible. You might call it madness, but I call it necessary.

When we are afraid of having too much hope, we’re actually afraid of being disappointed. We are anxious about expecting the world to gift us and show us grace, because what if we end up on our asses?

So we dream small or not at all. Because if we expect nothing or expect something small, we cannot be disappointed when the big things don’t happen. We think it’s a great defense mechanism, but what it really is is a liability on our lives, because we are constantly bracing for impact.

I haven’t really felt like I’ve had a dream or vision for years now.

The last month with no job has really blessed me with an opportunity to start dreaming again.

And guess what? It’s actually kinda fun to do it, even if it comes with some occasional failure and disappointment.

Because for me, the feelings that come with complacency are significantly worse than the risks that come from dreaming.

(Side topic for future Tim to explore: how are dreams and anxiety correlated?)

I’m used to the next right thing feeling certain and obvious. That’s probably because I’m used to being young. When you’re young, there are a lot of people out there whose examples you can imitate, and relatively low risk in trying things you’re not sure will work out. You also have an unearned confidence that comes from not having failed much yet.

But even the most conventionally successful of us, young or not, may reach a place in our careers where THERE IS NO OBVIOUS NEXT STEP. The things you’ve discovered you’re good at may not exactly line up with a standard corporate career path. There may no longer be an existing, ready-made challenge that’s the right size for you to step into.

There will just be a you-shaped hole in the world—its boundaries defined by your unique connections, the extreme limit of your skills, the scope of your ambitions—and trial and error is the only way you can figure out how to fill it.

As I’m oft to quote, Lisa Simpson’s “a challenge I can do” bit comes to mind here.

To be honest, this has been the toughest part of being on the job hunt.

I never wanted to follow a conventional career path. I’ve enjoyed the flexibility of my professional life so far, but I do yearn for the perceived stability of a full time thing. Many full time things don’t often give you much flexibility.

I suppose all I can do is just putting myself out into the world and explore until I find a “me-shaped” hole that looks close enough for me.

I sometimes hear the phrase “unapologetically you” tossed around, and I guess there comes a time where you either need to fully embrace that ethos or jump into premade boxes which only can represent a portion of your self.

I think I’m trying to pursue the former.

There is one person I can say objectively that I am smarter than, and it is me four years ago.

He knew all of the things I currently know except less.

He had all the life experiences that I currently have except fewer.

So why do I have an obligation to a guy who is not only dumber than me, but literally does not exist?

This talk is nearly ten years old, and it slaps in all the right ways.

I feel a tremendous debt to myself and my goals and aspirations, but some of those goals and aspirations are just... not me anymore.

I can't run like I used to, lest I want to have a knee replacement in five years.

I don't think I'll ever end up getting to all the breweries in the state, even though I run an app devoted to that purpose.

It's okay to let the dreams of your past self go in favor of newer, more relevant dreams.

By the way: I saw a follow up to this talk yesterday where he ended up concluding:

I do not have no obligation to my former self.

I have the obligation to my former self that I want to have.

And I want to have some.

Which means I should save my knees for a marathon with my kids.

(If that's what their dream is, of course.)

To hear him tell it, he doesn’t usually have much control over what he decides to focus on in those three hours. For a few months in the spring of 2019, all he did was read.

“Which means I didn’t do any work,” Huh said. “So that’s kind of a problem.” (He’s since made peace with this constraint, though. “I used to try to resist … but I finally learned to give up to those temptations.” As a consequence, “I became better and better at ignoring deadlines.”)

He finds that forcing himself to do something or defining a specific goal — even for something he enjoys — never works. It’s particularly difficult for him to move his attention from one thing to another. “I think intention and willpower … are highly overrated,” he said. “You rarely achieve anything with those things.”

This was a great biography about one person’s path towards discovering what they are passionate about.

I find a lot of parallels in my work. Agency life can be a grind, and it’s tough to say “deliver this work by this date” and feel motivated to deliver on it, especially when that work is not particularly novel or challenging.

I much prefer being still for a little bit, finding something to be curious about, and working towards discovering everything I can about that thing.

On a related note: I recently had a great talk with a coworker about the game I want to build. Our talk transformed that idea into one that now is making me motivated to learn more about AIs that generate visual components and how one could incorporate them into a dynamically-built world.

Kinda cool stuff, no?

I wanted to recapture the excitement I used to feel over finding out something that not very many people knew — the satisfaction I used to get from wrestling with things, spinning them around and trying to see the different angles. Before it all got buried beneath analytics and followers and “impact” and gimmicks and waiting for the next round of layoffs.

Not knowing how to say any of this out loud, I didn’t tell anyone. I just slowed down — backed off of pitching editors, stopped picking up late night phone calls from sources. I shifted my focus to editing other people’s work, which is less stressful and also pays better. I wrote some personal essays and took some college classes and sat on my kitchen floor trying to imagine what my Twitter bio would say if it didn’t start with “Freelance journalist.”

When I left JMG in March, this exact sort of identity crisis was a huge marble that wouldn’t stop rattling around my brain.

In the past nine months, I’ve become more comfortable letting go of my identities. Besides, what good are identities anyway?

My interests, my career path, my marital and paternal status, being a “runner”, being “the guy who always gets his steps in”, being “the guy who runs an app development company”… those are all tiny parts that add up to the whole.

My third grade teacher used to make us listen to a song every day that had a chorus which said “I can be the best I can be.”

And I think at this point in my life, that’s all I need to be.

(Thanks, Ms. Salute. ❤️)

The ultimate lesson, then, is to remind yourself that no, your current life is not normal.

It’s super weird and super specific, and you can completely change the damned thing in as many ways as you like and you absolutely will adapt and be able to handle it.

At some point you have to accept that other people’s perceptions of you are as valid as (and probably a lot more objective than) your own.

This may mean letting go of a false or outdated self-image, including some cherished illusions of unique unlovability.

I recently had a talk with Shannon that was eerily similar to the central conceit of this article.

We don’t get to pick how we show up in other people’s interpretation of ourselves. The author’s story about his dad sleeping at the movie theater next to him is a great example.