The Dark Side of a Side Business

I heard from an old college buddy that one of our mutual friends has hooked up with an old flame.

Trouble is, he’s already married.

He hasn’t done anything irretrievable yet—just some phone calls and a clandestine lunch date—but he’s definitely sidling up to infidelity. Just another sad country song, really, but I was totally surprised.

I’ve always admired—and good-naturedly envied—his picture-perfect life: a Pottery Barn house, two kids, a wife with a profitable home business, and a stable job he actually likes.

It appears I think better of his life than he does, yeh?

And in worrying over his marital side hustle, I realized that side businesses can have a similar taint…

…because some employers don’t mind if their employees have other jobs, but others have contract clauses against moonlighting and tacit dissuaders to keep employees monogamous.

And for folks cheating on their partners or their employers, the same rules apply—

1. You will get caught
   Your inner conflict is going to seek resolution with a mind of its own and sabotage your secrecy. You’ll forget to remember a lie that you told, you’ll leave something on the kitchen table (or desk) that you meant to hide, or you’ll say what should be left unsaid.
2. Living two lives requires four times the effort of living one
   If you’re going to keep this up, you can’t grow complacent and you can’t relax because you can’t afford to misstep. You’ll need strategy and tactics for outwitting your partner/employer…every single day. Are you up for that?
3. Are you sure they’re worth it?
   Don’t ask yourself if your secret attraction is worth cheating for. Ask if it’s worth getting caught for.
4. Because you will get caught
   Your partner/employer knows and sees more than you imagine. You might not even notice that you’ve changed in some small, semi-invisible way, but someone intimate with you is sure to pick it up.
5. Be careful who you ask for help
   Conspirators and corroborators abound. It will be easy to find people who think what you’re doing is great, particularly if they’re doing the same thing. For a side business especially, it’s key to find someone who talks the nitty-gritty not-so-pretty stuff, like Pam and Dave and Mark.
6. Be *really* careful who you ask for help
   Today’s eager collaborator can be tomorrow’s embittered Benedict Arnold.
7. Why are you doing this…really?
   Like my old college buddy wisely said: “If you’re thinking about cheating, you’d best stop thinking about how to cheat and start thinking about why you’d want to.”
   If you’re thinking about having something on the side, it’s because there’s a gap between what you have and what you want. You need to be clear on what exactly that is to make effective decisions.
8. You can’t run from yourself
   You play a part in whatever drama there is in your home or office that you’re trying to escape. Like the Have/Want Gap, you need to be clear on what your role is, or you may, in time, recreate it in your side hustle.
9. The grass may not be all that greener
   What you’ve got happening on the side may be better than your main gig. But ask yourself what it would be like without the excitement that comes with its secrecy and novelty. What would it be like to be 100% in this, without that stable main gig to fall back on?
10. Because you will get caught
    Someone you know—or who only knows you—will see you where you’re not supposed to be, doing what you’re not supposed to do. And they’ll tattle out of loyalty to your partner/employer, loyalty to principle, or because they never really liked you all that much.

.

I’m just saying…

Photo credit: afroboof