That One Big Break

I just had a famous billionaire fly me, first class, to his mansion to talk about writing his life story.

Yup, that actually happened.

And I can’t think of a better opening line for an article than that because that one amazing sentence not only grabs you, but elevates me at the same time: Who is this writer who’s being flown to billionaires’ homes? Now you’re curious. Now you want to learn more.

This first sentence could also work on a visual level as the opening for a film, where the wealthy tycoon reaches out to the broke writer—usually it’s a broke private detective, but we’ll substitute writer here—to offer the deal of a lifetime: a huge paycheck, a glance behind the curtain, and by doing so, taking this author from unknown to center stage. From one of many, to one of a few.

Now, I’ll skip ahead and tell you that I didn’t get this life-changing, bank account–booming, career-altering gig. I did well at the interviews and the actual meeting—well, I think I did—and I didn’t embarrass myself or the literary agency that sent me. I didn’t show up drunk, I didn’t try to sneak photos of the exotic cars in the garage, and I didn’t mention as an ice breaker any of the interesting articles I had read about this billionaire’s current legal trouble.

Yeah, looking back, I did okay. But I still didn’t get the job.

And I’m now feeling the impact of not getting it. I’m dealing with the emotional hangover and looking at the cost of not being given this award, this prize, this bonus card that would have moved me five spaces on the game board. Because there was a cost.

From a mental perspective, I know most people would say I should be honored and flattered that I even made it to the final bonus round of a handful of writers being considered for such a high-profile and lucrative deal. Yes, absolutely; my mind agrees with that assessment.

And my heart is telling me that it’s probably for the best that I didn’t get the job. The billionaire subject of the book has had something of a questionable history, and I suspect there would have been some dark aspects to navigate that would have had an emotional cost for me as the narrator. Absolutely, this is also true.

But it’s this other area, this yet unidentified set of data points, that keeps gnawing at me.

See, this opportunity, this project, would have changed my life, and would have done so very quickly. In one move, one decision, my world would have been different in so many areas: financial, career, position, title, access, clout. Boom.

And that’s where I think the gnawing comes from. It’s not that my life would have changed as fast as a lottery winner’s does, but that I needed a lottery win to make it happen. Not only could I not get to that place as quickly without this opportunity, but, I worry, it’s possible that I can never get to that same place without it.

I needed this powerful lottery win to swoop down from the heavens and pick me, this lowly shepherd, and speak: Verily, you shall be the one I have chosen. I would cast away my rags and join the billionaire in the clouds, with my name being mentioned on daily news feed coverage.

Without being chosen, without that golden ticket, I worry that I will be . . . well, just me.

When you buy a lottery ticket, the bonus feature attached is that there are three minutes of wondering: What if I actually won this thing? It’s the quick high that is the true lure of buying the ticket. It lasts for a few minutes, or maybe hours, and we mourn the fantasy a little when it’s gone, but it hasn’t been around long enough for us to really miss it.

But from the time I got on the plane for this meeting, with every limo ride, and even for the three days after I came home, my center mental focus was: Wow, this is going to change everything.

Then I started believing and planning. It became real. And then it was gone.

When a big “could have” happens, it builds. The mind begins to see the potential changes as if they’ve already happened. You think: I’ll be able to pay off this, I’ll have access to that, this person will be proud, that one will be jealous. You begin to believe it, to see it. It’s yours.

Then, when the bubble pops, it doesn’t leave you back where you were before. No, it pushes you back three steps behind, emotionally. You’re in a lower place. A sadder one.

I’ve always hated that “one big break” concept because it’s not about that one pivotal moment: that meeting, that small success, that venture that started us on a different path. The one big break myth is the Cinderella moment. It takes the guy washing dishes to the corner office, the lady cleaning hotel rooms to the Hollywood walk of fame, the homeless guy to the red carpet at the Emmys.

There are so, so many of us who are banking on that one big break. So much so that we just lean into our brooms, we bus those tables, we sleep under those bridges, without a plan, only the hope that the next person we meet will discover us, make us, give us that break that we deserve and are entitled to. That one big break. Because maybe today . . .

And this kind of pisses me off. Not that the futile concept of “one big break” exists, but that I was banking on it . Counting on it. Believing in it.

I’m glad I didn’t get this—well, sort of. Because now I can get to work and start working on creating my own break, not one big one but several small ones, if that’s what it takes. Whatever their size, they’ll be breaks that I create. Not one big one that is given to me.