The (real) golden rule of entrepreneurship — from someone who keeps breaking it


Reminder: NEVER NEVER EVER put the success of your business/career in someone else’s hands.

In my six years as an entrepreneur, I’ve had a ton of ups and downs. Things have pulled through and fallen through, blown up and tanked.

But every single time, without fail, my most stressful moments followed the same pattern:

Part 1: I receive an invitation for a project or collab that feels like an easy (and lucrative) “Yes!”

Part 2: Such an invitation leans on the success of someone else — whether it was an agency taking off, an affiliate launch, a product or mastermind I wasn’t involved with selling well, a big contract pulling through, or a promise of “more work after suchandsuch happens”.

Part 3: If it seems like a sure-enough thing, I let myself get a little lazy. I feel confident, and plan the next few months of my business around it before the contract is signed or the numbers are confirmed and in place.

Then — BOOM. Something changes.

Life happens.

Sales aren’t what they should be.

Businesses shift directions.

Clients get slow-burn sticker shock.

Some of these promises are small, others were change-my-business HUGE. But they all have one thing in common:

Without follow-through, a contract, and a deposit, they meant exactly 0 — even if the person is high-integrity and successful in all respects.

There’s just no way to predict an outcome, no matter how shiny and solid looking it seems from a distance, until all is sealed and signed.

The next month, 3 months, 6 months, or year of your business can NEVER hinge on someone else pulling through for you, no matter how much money they make, or how much they genuinely like and care about you.

Similarly — you should always be able to pull through for yourself.

That’s why the golden rule of entrepreneurship must be: Count on yourself — and no one else.

It sounds dramatic, but this degree of constant cynicism goes a long, long way.

And hey: No matter how seasoned you are, it’s still easy to get seduced.

It happens.

I would know. Golden promises fall onto my plate a few times a year, and every time my eyes light up with the glow like Scrooge McDuck.

“Omg, maybe this is it! This is the opportunity that’s about to change everything.”

Immediately I begin to picture my life after the perfect outcome materializes. Doing work I’m obsessed with. Speaking on international stages. Bathing in cash and Lush bath bombs I don’t even check the price tags on. A designer handbag collection. Tropical vacations. Sabbaticals.

Time and experience have taught me: Reality is rarely as sexy as we anticipate, and fancy promises rarely transmute from gas into a solid state.

Think about it. Just getting out of bed in the morning exposes you to a million different outcomes. But it’s up to you to get dressed, and be on your way, and create the day you want to have.

Business works the same way — and even the most predictable track record of success can suffer an upset at any moment.

I’ve been fortunate in that each time shiny promises make me complacent and suddenly get broken, I manage to fill the holes (while sweating and swearing a lot) — but it’s always scary as hell.

As a rule, I always keep a few irons in the fire; clients I know always have work, projects I can move up, a wait list etc. But it’s never fun to go from “I’m set! Soandso told me so.” to “Ohfuckohfuckohfuck, what now?!”

So how do you prepare? How do you stay solid in an uncertain world, and an even more uncertain way of working?

You stay centered. You never stop thinking long-term.

People will offer you fancy, shiny things along the path of your career (they probably already have. And if they haven’t yet? They will.), but treat absolutely nothing as set-in-stone until it’s officially underway, no matter what you’re promised.

After all: At the end of the day, the only person you can count on 100% is yourself; as your best advocate, advisor, and money-maker.

Being a good business owner doesn’t just mean having a good product or service, and a solid brand. It also means having a plan B and C in your back pocket.

So: Continue to nurture past client relationships. Burn no bridges that don’t deserve burning. Have a waitlist if you’re booked out. Never be too shy to pitch yourself, no matter how experienced or internet-famous you think you are. Diversify your gawddamn revenue streams. Practice your footwork.

Promises come and go, but a strong foundation is forever.

Stay as hopeful as you can, but as cynical as you must.

Always have a clear vision in mind that’s reliant on YOUR work, and no one else’s.

And don’t let the shiny stuff distract you.

Hillary Weiss is a copywriter, ghostwriter, writerwriter, and creator ofThe Wordshops: Copywriting Courses for Unconventional Entrepreneurs. Since 2011, she’s been the pen, voice, and verve for 200+ brands and counting, and specializes in brand voice development and big-money messaging for profoundly rad brands with something real to say. For more stuff like this, and to jump on her mailing list, hop over to To get your hands on her course, stop by

Photo by veeterzy on Unsplash

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