I’ve always hated the thought of sales as a skill. It always felt like: well is the product good or not? Don’t woo me.
And yet, wooing is an art, and one I’ve used often when selling consulting engagements. I suppose I used it when selling myself as a life partner to my husband Brad. In a total coup I even managed to sell braces to Arden.
I wasn’t selling snake oil in any of these situations, but I’d like to think my selling contributed to a lack of buyer’s remorse. We want to feel good about our choices; for them to sit within stories we like telling about ourselves. Good selling helps with that.
And yet, not all stories are helpful. Sometimes we tell ourselves we’re in a rut, forgetting just last year we dreamt of predictability!
When I find myself telling unhelpful stories, I look to Stoicism. I appreciate its insistence that most of our problems are self-conceived: sprouted from stories we layer on top of facts. Did someone show up to the meeting with wet hair? They don’t respect you! (Or maybe, they have some liquid H2O molecules adhered to the protein fiber growing out of their head. AND??)
All of this means not that the stories we tell ourselves are dumb, but that they’re mutable. We can literally just make them up! And you know who tells really great stories?
The Sales Bro1.
(If you don’t have a good archetype in your head for this character, here’s some inspiration.)
The Sales Bro is completely overconfident but charismatic enough to make you think he’s just regular confident. He’s done this “a million times” and “knows what you’re gonna want.” He can describe a ridiculous upsell as obviously the thing anyone in your position would choose.
He’s kind of skeezy until you wonder if his powers can be used for good… What if you set him loose on selling your life… back to you?
Let’s say you normally think of your life this way:
You have a stable job that pays the bills. You’ve been there longer than you probably should… not so much growth, and sometimes long hours. And yet, you don’t know what else to do and figure you should probably be grateful for the job at all. On the side you spend time on your art—a passion you’ve had since middle school. But that’s not taking off either. You’re not making a ton of money and you wonder if there’s something else you should be doing… some other move you should make.
Now, let the sales bro sell your life:
Okay, you’re going to want to have what we call an “anchor job”. There are five job types and I can walk you through them sometime, but the TLDR is that the anchor job is the one you want. Make sure there’s not too much growth. I know that sounds wild, but trust me. Too much growth and you start mistaking your job for your identity. Also, there needs to be occasional stress. One of the defining characteristics of the anchor job is that hours can be long. I know, I’m blowing your mind, but hear me out. When’s the last time you had a really great story to tell about work? It wasn’t when you were heading out at 5pm was it? I bet it was a big push to meet a deadline and it was nuts. You’re gonna want stories to tell about your career or your anchor job falls flat. An anchor job’s defining characteristics are 1. stable, 2. little growth, 3. occasional long hours. You have that? Amazing.
Now here’s the second piece: You need a “buoy hobby” that you do on the side but is NOT—and I repeat is NOT—taking off. The worst thing is having two jobs at once. You don’t want that. You want this to be your passion, preferably something you’ve loved since childhood, and you want it to stay a hobby. That way you’re not stuck in an in-between place of “trying to make it”. It’s a buoy hobby because it keeps you creatively afloat, not financially afloat. Your art’s not taking off? Perfect.
And finally, the kicker: You absolutely don’t want to be making too much money. You know what happens when people start making a lot of money? They start spending a lot of money. And then they’re so locked into the “golden handcuffs” of the big jobs that they can never leave. Gotta make that second house payment, amirite? Rich people always feel the poorest, and you don’t want that. I’ve seen this movie a hundred times and I know who gets the happy ending. It’s the person with the anchor job, the buoy hobby, and not too much money.
Trust me, buddy: You’re living the dream.
Sometimes a Sales Bro can come in real handy! None of this is to say you should lie to yourself, and if it’s time to make a change then no amount of sales speak should talk you out of it. It is to say that sometimes, we can improve our lives simply by telling ourselves different stories.
One way to get yourself to this place is to ask who might be jealous of you and for what. Not as an exercise in self-aggrandizement, but as an exercise in seeing through other eyes that what you already have, what you’ve already built, is pretty cool!
And it’s not all “well my poor unemployed friend would be jealous of me.” We’re so used to admiring wealth, power, and fame that we forget a lot of those wealthy, powerful, famous people aren’t that happy! Maybe a friend with a big fancy career would see your relatively simple life as romantic. Maybe your powerful cousin would envy how easily you sleep at night. Maybe the kid from your high school who blew up as an influencer wishes they didn’t have to keep up appearances every day, forever.
And let’s not forget that you probably have a lot of things today that Past You only dreamt of.
If you ever need help remembering it, just look to your inner Sales Bro. Dude’s got your back.
P.S. Feel free to put a life situation in the comments (yours or a friend's or an imaginary one) and maybe we can “Sales Bro” them together?
Yes, this can totally be Sales Gal or Sales Person, but we’re trying to conjure a caricature here.

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