Striking Out

We typically use the term “striking out” to convey that someone has used up their last shot and is out of the game. Three strikes and yer out. As American as apple pie.
There is also the sense in which someone is striking out on their own – casting their net and trying something new. Not failure. Not success. But attempting. The end is not yet written. In this sense, one doesn’t know where they will end up, which rules apply or how; there isn’t a map. Think exploration. Discovery, Learning. Finding a path forward. Getting turned around.

I contemplate striking out in both senses all the time. What if I finally strike out in my career and fail? What if I strike out on my own and succeed? Or fail. It quickly comes back to failure. I think that this reveals a deep pathology within me. Within all of us.

We are winners or losers, especially when it comes to careers. The frame is set and however it is that you think about it, it essentially, or at least eventually, comes back to failure. Or, really, the deep-seated fear of failure.

Failure is a lurking criminal, always threatening to pounce when you walk out of the house, when you go somewhere new, when you step off the well-trod path. New idea? It could fail. Anything other than what is in front of you, what has been prepared for you, what has been conceived already on your behalf, is the bad part of town. Respectable people don’t go to the bad part of town. Who knows what could happen? It will likely be terrible.

Except, based on what?

When I first moved to DC nearly twenty years ago, I was told that I lived in a bad area. People were regularly beaten and mugged, and worse, right on my block. I regularly received gape-mouthed stares and hushed tones of concern. And, wow, the evidence was everywhere. I mean, there was a parking lot across the street from my apartment. Hell, you know what happens in parking lots. And, my place was cheap. No one respectable would pay so little for an apartment, not in Washington, DC. And, there were corner stores. Corner stores where single bottles of liquor and cigarettes were sold. What kind of urban hell was I subjecting myself to? My poor mother.


Well, I lived three blocks from my office. In the U.S. Senate. There was a police station next door. The parking lot was gated, guarded, and well-lit. A new gourmet restaurant opened on the corner, 30 feet from my front door. My landlord was a former US Senator. I was twos of blocks from Union Station, think tanks, lobbyists, and the Supreme Court. I could walk everywhere, at any hour, pretty safely, because there were about 15 overlapping police jurisdictions that patrolled my street. Yeah, I had a lot of personal safety issues.

The point is that if I had followed the warnings I heard, I would have avoided that neighborhood like the plague. Lock your doors, you’re on Second Street. But, it was ridiculous. I loved and afforded where I lived. In the years since, I’ve lived in much more respectable neighborhoods in which I’ve coincidentally experienced far more personal safety issues, including a fairly violent mugging. Now, I don’t connect these facts causally. But, I do think of them when I recall how wrong all those people were and how stupid (bless their hearts) their advice was.

The fear that keeps people in line, and in many cases, unhappy and unhealthy, is driven by the same sensibility that told all those people to warn me against where I lived. There was a trigger – some selective information – that made it appear unacceptable. I lived there long enough, enjoyed it for specific reasons, and regularly verified that these people were full of shit. I had a fact-based opinion, and they had fear-based opinions.

I think the same applies to striking out on your own. People fear – they just know – that this is setting you up to strike out and get pulled out of the game. But, they don’t know.They don’t know that you will fail. They don’t know that failure is even bad. You may very well fail. Fail at becoming partner, getting raises, landing big accounts, knowing exactly how big your next paycheck will be, etc. etc. But are those metrics of success? And how sure are those bets anyway? How much will they cost you, and will it be worth it? Who’s done the ROI on that?

You may even find that your business idea doesn’t work. But, why is that failure? Isn’t that data collection? Refine, test, refine, test, refine, test.

There is another hidden assumption in the feared failure narrative, which is that you will always be safe as a cog. Machines need cogs, yes? Sure, but the point is that they are replaceable. How smart a machine is it that needs only just the right, irreplaceable part? Not very. And, people clearly don’t have a lot of faith in this assumption, either. They worry (rightly) about downsizing, restructuring, not advancing, not being relevant. They do things they hate or dread because that’s what you do to survive. They defer things they love and hope for so that they can have more security.

And, it’s not even just about independently being successful or secure just so that you don’t have to have a boss. There is the sense that everything can be arranged differently. Keeping up with the Joneses feeds keeping up with your career – they feed each other in a sometimes perverse cycle of one-upmanship. But, if you remove yourself from the workplace grind, why can’t you remove yourself from the social grind, too?

It’s time to consider whether striking out is really about failure or beginning a new adventure.

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