Here’s a question that’s been nagging us: What is your hustle’s Original?
Every hustle begins with hope.
Maybe yours started with the thrill of landing that first client, selling that first product, or finally saying Yes to yourself after too long saying No.
You spotted the opportunity. Did the mental math. Determined how, if A, B, and C came together, that would equal cash in your pocket.
You started to hustle. You laid out the idea, the hook, the pitch.
And it worked! And worked again! And things started rolling from there.
But almost as soon as a hustle is born, a shadow forms alongside it: the Original Sin.
The Original Sin of any hustle is simply the one thing you didn’t do when you started, that you should have done.
The skipped step, the overlooked foundation, the critical seed that—if left unacknowledged—can sprout into thorny problems years later.
Pretty much every hustle/business/venture does it.
Our Original Sins?
We’re guilty of:
Numerous charges of Marketing Too Inconsistently…when the marketing should have been working for us 24/7 to propel success perpetually.
Our rap sheet had one of us trying to “be the nice guy,” where we blasted away the boundaries of our work/life balance to go the extra mile for a client who, frankly, didn’t give a shit.
(How do we feel about swearing in this NL?) Write to let us know.
We know one group that propelled itself to massive success on just one client, only to have that client say, Whoops, Gotta Go. Yeah, it hurt.
You get the point.
It’s so easy to commit the Original Sin. Hard as hell to get out of it.
Afew examples that may sound familiar:
The Contractor’s Sin: You launched without setting clear contracts or scopes of work. At first, it was fine, clients were friendly, and money came in. But then someone pushed back on payment, or added “just one more thing,” and suddenly you were losing sleep because the guardrails weren’t there.
The Freelancer’s Sin: You priced yourself low to get traction, promising you’d raise rates later. But momentum took over, referrals came in at the same low price, and now you’re afraid that raising rates will chase everyone away.
The Creative’s Sin: You didn’t claim ownership of your work in writing. The client who seemed chill suddenly sold your designs to someone else, or reused your content without credit.
The Startup’s Sin: You put off bookkeeping because you focused on growth. Fast forward, and now you’re staring at a year of receipts, IRS deadlines, and panic.
The Digital Creator’s Sin: You built everything on rented land: one social platform. It grew fast, followers loved you. Until the algorithm changed, your reach tanked, and you realized you never built an email list or owned your audience.
The Small Business Sin: You didn’t hire or delegate soon enough. You told yourself, “I’ll save money by doing it all myself.” But eventually, doing everything turned into doing way too much, and doing little of it well.
What’s your hustle’s Original Sin?
We’re probably all guilty of not asking for help when we need it.
The good news? You’re not alone.
Left unchecked, Original Sins grow.
Weak contracts turn into unpaid invoices. Messy bookkeeping turns into late payments and tax penalties. Neglected marketing leads to working for someone else, and not yourself.
What begins as a minor oversight metastasizes into a business-threatening problem.
So what can you do about it, like now, today?
1. Name It
The first step is honesty. Ask yourself: What’s my hustle’s Original Sin? It won’t feel good. You may even want to look away. But naming it pulls it from the shadows into the light, where it loses its power.
2. Circle Back
Most “too late” problems are not actually too late. If you’ve been underpricing, you can start raising rates with new clients (here’s how to do that.) and then work your way back to old ones.
TIP: Refer to your real, full rates as List Prices. Give those to new clients. If they balk, you can negotiate from your secret discount menu. But remember, everything is negotiable. What are they giving up to get a lower rate? Fewer drafts? Capped hours? Work at your leisure? There’s plenty of wiggle room here. So much so, we should write about it in an upcoming letter.
If you never made contracts, you could introduce them now under the banner of professionalism. If you’ve ignored marketing, you can block one hour a week to start. It’s rarely about fixing everything at once. One small, consistent redemptive action can absolve startup haste.
3. Contain It
If the problem has grown, create boundaries around it so it doesn’t spread. That might mean cutting off a client who refuses to sign agreements, putting hard limits on “friends and family discounts,” or switching platforms before you’re trapped. Containment keeps the sin from becoming systemic.
4. Forgive Yourself, Then Fortify
No one starts perfectly. Not you, not the brands you admire, not even Fortune 500 companies. The difference is, they eventually circled back. You can too. The act of fortifying, where you fix the weakness and build the foundation you skipped, allows you to continue growing, only now with peace of mind.
Sounds dreamy, right? But the goal remains to build something that outlasts you, including those nasty little startup screw ups.
If you can ask, What was my Original Sin? then you can take action to redeem it.
-EA
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